# Patent

## Title
Herbicidal substituted pyrimidinyloxy benzene compounds

## Abstract

Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof,




wherein each Y1, Y2, Y3, Y4, Z, R2, m and R3 are as defined in the disclosure.

Also disclosed are compositions containing a compound of Formula 1 and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of a compound or a composition of the invention.

## Background
FIELD OF THE INVENTION
This invention relates to certain substituted pyrimidinyloxy benzene compounds, their N-oxides, salts and compositions, and methods of their use for controlling undesirable vegetation.
BACKGROUND OF THE INVENTION
The control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, maize, potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safer or have different sites of action.
JP 61236766 A discloses certain carbon-linked pyrimidinyloxy benzene derivatives as herbicides. The substituted pyrimidinyloxy benzene compounds of the present invention are not disclosed in this publication.
SUMMARY OF THE INVENTION
This invention is directed to compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides




    
    
        wherein
        each Y1, Y2, Y3 and Y4 is independently N or CR1, provided no more than 3 of Y1, Y2, Y3 and Y4 are N;
        Z is O or S;
        each R1 is independently hydrogen, halogen, cyano, nitro, SF5, CHO, C(═O)NH2, C(═S)NH2, SO2NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C8 alkylcycloalkyl, C4-C8 cycloalkylalkyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C3-C7 cycloalkylcarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C4-C8 cycloalkylalkoxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkoxyhaloalkyl, C2-C6 alkoxyalkoxy, C2-C4 alkylcarbonyloxy, C2-C6 cyanoalkyl, C2-C6 cyanoalkoxy, C2-C4 alkylthioalkyl, SOnR1A, Si(CH3)3 or B(—OC(R1B)2C(R1B)2O—); or a phenyl ring optionally substituted with up to 5 substituents independently selected from R1C; or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R1C on carbon atom ring members and R1D on nitrogen atom ring members;
        R2 is halogen, cyano, nitro, C1-C4 alkoxy, C1-C4 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, SOnR2A, C1-C4 haloalkyl or C3-C6 cycloalkyl;
        m is 0, 1, 2 or 3;
        each R3 is independently halogen, cyano, hydroxy, nitro, amino, CHO, C(═O)NH2, C(═S)NH2, SO2NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C8 alkylcycloalkyl, C4-C8 cycloalkylalkyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C3-C7 cycloalkylcarbonyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C4-C8 cycloalkylalkoxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkoxyhaloalkyl, C2-C6 alkoxyalkoxy, C2-C4 alkylcarbonyloxy, C2-C6 cyanoalkyl, C2-C6 cyanoalkoxy, C2-C4 alkylthioalkyl, Si(CH3)3, C≡CSi(CH3)3, C(═O)N(R3A)(R3B), C(═NOR3C)H, C(═NR3D)H, SOnR3E; or a phenyl ring optionally substituted with up to 5 substituents independently selected from R3F; or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R3F on carbon atom ring members and R3G on nitrogen atom ring members; or pyrimidinyloxy;
        each n is independently 0, 1 or 2;
        each R1A, R2A and R3E is independently C1-C4 alkyl, C1-C4 haloalkyl, C1-C4alkylamino or C2-C6 dialkylamino;
        each R1B is independently H or C1-C4 alkyl;
        each R1C is independently hydroxy, halogen, cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy;
        each R1D is independently cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C2-C6 alkylcarbonyl;
        each R3A is independently C1-C4 alkyl or C1-C4 haloalkyl;
        each R3B is independently H, C1-C4 alkyl or C1-C4 haloalkyl;
        each R3C is independently H or C1-C4 alkyl;
        each R3D is independently H, amino, C1-C4 alkyl or C1-C4 alkylamino;
        each R3F is independently hydroxy, halogen, cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; and
        each R3G is independently cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C2-C6 alkylcarbonyl;
    
    


provided when i) Y1 is N; Y2 is CH; Y3 is CBr; Y4 is CH; and R2 is Cl, then R3 is other than 5-CF3, 5-CN or 5-NO2; ii) Y1 is N; Y2 is CH; Y3 is CBr; Y4 is CH; and R2 is Br, then R3 is other than 5-CF3; and iii) Y1 is N; Y2 is CCH3; Y3 is CCl; Y4 is CCl; and R2 is Cl, then m is other than 0.
More particularly, this invention pertains to a compound of Formula 1 (including all stereoisomers), an N-oxide or a salt thereof. This invention also relates to a herbicidal composition comprising a compound of the invention (i.e. in a herbicidally effective amount) and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents. This invention further relates to a method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of the invention (e.g., as a composition described herein).
This invention also includes a herbicidal mixture comprising (a) a compound selected from Formula 1, N-oxides, and salts thereof, and (b) at least one additional active ingredient selected from (b1) through (b16); and salts of compounds of (b1) through (b16).


DETAILS OF THE INVENTION
As used herein, the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having,” “contains”, “containing,” “characterized by” or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated. For example, a composition, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method.
The transitional phrase “consisting of” excludes any element, step, or ingredient not specified. If in the claim, such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase “consisting of” appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.
The transitional phrase “consisting essentially of” is used to define a composition or method that includes materials, steps, features, components, or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components, or elements do not materially affect the basic and novel characteristic(s) of the claimed invention. The term “consisting essentially of” occupies a middle ground between “comprising” and “consisting of”.
Where applicants have defined an invention or a portion thereof with an open-ended term such as “comprising,” it should be readily understood that (unless otherwise stated) the description should be interpreted to also describe such an invention using the terms “consisting essentially of” or “consisting of.”
Further, unless expressly stated to the contrary, “or” refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).
Also, the indefinite articles “a” and “an” preceding an element or component of the invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore “a” or “an” should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular. As referred to herein, the term “seedling”, used either alone or in a combination of words means a young plant developing from the embryo of a seed. As referred to herein, the term “broadleaf” used either alone or in words such as “broadleaf weed” means dicot or dicotyledon, a term used to describe a group of angiosperms characterized by embryos having two cotyledons.
As used herein, the term “alkylating agent” refers to a chemical compound in which a carbon-containing radical is bound through a carbon atom to a leaving group such as halide or sulfonate, which is displaceable by bonding of a nucleophile to said carbon atom. Unless otherwise indicated, the term “alkylating” does not limit the carbon-containing radical to alkyl; the carbon-containing radicals in alkylating agents include the variety of carbon-bound substituent radicals specified for R1 and R3.
In the above recitations, the term “alkyl”, used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers. “Alkenyl” includes straight-chain or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. “Alkenyl” also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. “Alkynyl” includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. “Alkynyl” can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. “Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. “Alkoxyalkyl” denotes alkoxy substitution on alkyl. Examples of “alkoxyalkyl” include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2. “Alkylthio” includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. “Alkylthioalkoxy” denotes alkylthio substitution on alkoxy. “Cyanoalkyl” denotes an alkyl group substituted with one cyano group. “Examples of” “cyanoalkyl” include NCCH2, NCCH2CH2 and CH3CH(CN)CH2. “Cyanoalkoxy” denotes an alkoxy group substituted with one cyano group.
“Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The term “halogen”, either alone or in compound words such as “haloalkyl”, or when used in descriptions such as “alkyl substituted with halogen” includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, or when used in descriptions such as “alkyl substituted with halogen” said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” or “alkyl substituted with halogen” include F3C, ClCH2, CF3CH2 and CF3CCl2. The term “haloalkoxy” is defined analogously to the term “haloalkyl”. Examples of “haloalkoxy” include CF3O—, CCl3CH2O—, HCF2CH2CH2O— and CF3CH2O—. “Alkylcarbonyl” denotes a straight-chain or branched alkyl moieties bonded to a C(═O) moiety. Examples of “alkylcarbonyl” include CH3C(═O)—, CH3CH2CH2C(═O)— and (CH3)2CHC(═O)—. Examples of “alkoxycarbonyl” include CH3OC(═O)—, CH3CH2OC(═O)—, CH3CH2CH2OC(═O)—, (CH3)2CHOC(═O)— and the different butoxy- or pentoxycarbonyl isomers.
The total number of carbon atoms in a substituent group is indicated by the “Ci-Cj” prefix where i and j are numbers from 1 to 6. For example, C1-C4 alkylsulfonyl designates methylsulfonyl through butylsulfonyl; C2 alkoxyalkyl designates CH3OCH2—; C3 alkoxyalkyl designates, for example, CH3CH(OCH3)—, CH3OCH2CH2— or CH3CH2OCH2—; and C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH3CH2CH2OCH2— and CH3CH2OCH2CH2—.
When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1, said substituents (when they exceed 1) are independently selected from the group of defined substituents, e.g., (R3)m, m is 0, 1, 2, 3 or 4. Further, when the subscript indicates a range, e.g. (R)i-j, then the number of substituents may be selected from the integers between i and j inclusive. When a group contains a substituent which can be hydrogen, for example R3B, R3C or R3D then when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted. When a variable group is shown to be optionally attached to a position, for example (R3)m wherein m may be 0, then hydrogen may be at the position even if not recited in the variable group definition. When one or more positions on a group are said to be “not substituted” or “unsubstituted”, then hydrogen atoms are attached to take up any free valency.
Unless otherwise indicated, a “ring” or “ring system” as a component of Formula 1 (e.g., —Y1═Y2—Y3═Y4—) is heterocyclic. The term “ring member” refers to an atom or other moiety (e.g., C(R1), N) forming the backbone of a ring or ring system.
The term “optionally substituted” in connection with the heterocyclic rings refers to groups which are unsubstituted or have at least one non-hydrogen substituent that does not extinguish the biological activity possessed by the unsubstituted analog. As used herein, the following definitions shall apply unless otherwise indicated. The term “optionally substituted” is used interchangeably with the phrase “substituted or unsubstituted” or with the term “(un)substituted.” Unless otherwise indicated, an optionally substituted group may have a substituent at each substitutable position of the group, and each substitution is independent of the other.
When —Y1═Y2—Y3═Y4— taken together with the nitrogen atom to which both ends are attached, it is a 5-membered nitrogen-containing heterocyclic ring, it is attached to the remainder of Formula 1 only though the indicated nitrogen ring atom.
A wide variety of synthetic methods are known in the art to enable preparation of aromatic and nonaromatic heterocyclic rings and ring systems; for extensive reviews see the eight volume set of Comprehensive Heterocyclic Chemistry, A. R. Katritzky and C. W. Rees editors-in-chief, Pergamon Press, Oxford, 1984 and the twelve volume set of Comprehensive Heterocyclic Chemistry II, A. R. Katritzky, C. W. Rees and E. F. V. Scriven editors-in-chief, Pergamon Press, Oxford, 1996.
Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. Stereoisomers are isomers of identical constitution but differing in the arrangement of their atoms in space and include enantiomers, diastereomers, cis-trans isomers (also known as geometric isomers) and atropisomers. Atropisomers result from restricted rotation about single bonds where the rotational barrier is high enough to permit isolation of the isomeric species. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. The compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers or as an optically active form.
Preferably the compositions of this invention have at least a 50% enantiomeric excess; more preferably at least a 75% enantiomeric excess; still more preferably at least a 90% enantiomeric excess; and the most preferably at least a 94% enantiomeric excess of the more active isomer. Of particular note are enantiomerically pure embodiments of the more active isomer.
Compounds of Formula 1 can comprise additional chiral centers. For example, substituents and other molecular constituents such as R2 and R3 may themselves contain chiral centers. This invention comprises racemic mixtures as well as enriched and essentially pure stereoconfigurations at these additional chiral centers.
Compounds of Formula 1 typically exist in more than one form, and Formula 1 thus include all crystalline and non-crystalline forms of the compounds they represent. Non-crystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts. Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline types). The term “polymorph” refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and/or conformations of the molecules in the crystal lattice. Although polymorphs can have the same chemical composition, they can also differ in composition due the presence or absence of co-crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability. One skilled in the art will appreciate that a polymorph of a compound of Formula 1 can exhibit beneficial effects (e.g., suitability for preparation of useful formulations, improved biological performance) relative to another polymorph or a mixture of polymorphs of the same compound of Formula 1. Preparation and isolation of a particular polymorph of a compound of Formula 1 can be achieved by methods known to those skilled in the art including, for example, crystallization using selected solvents and temperatures. For a comprehensive discussion of polymorphism see R. Hilfiker, Ed., Polymorphism in the Pharmaceutical Industry, Wiley-VCH, Weinheim, 2006.
One skilled in the art will appreciate that not all nitrogen-containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen-containing heterocycles which can form N-oxides. One skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for the preparation of N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane. These methods for the preparation of N-oxides have been extensively described and reviewed in the literature, see for example: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp 748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boulton and A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keene in Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J. Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G. Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., Academic Press.
One skilled in the art recognizes that because in the environment and under physiological conditions salts of chemical compounds are in equilibrium with their corresponding nonsalt forms, salts share the biological utility of the nonsalt forms. Thus a wide variety of salts of a compound of Formula 1 are useful for control of undesired vegetation (i.e. are agriculturally suitable). The salts of a compound of Formula 1 include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids. When a compound of Formula 1 contains an acidic moiety such as a carboxylic acid or phenol, salts also include those formed with organic or inorganic bases such as pyridine, triethylamine or ammonia, or amides, hydrides, hydroxides or carbonates of sodium, potassium, lithium, calcium, magnesium or barium. Accordingly, the present invention comprises compounds selected from Formula 1, N-oxides and agriculturally suitable salts thereof.
Embodiments of the present invention as described in the Summary of the Invention include the following (where Formula 1 as used in the following Embodiments includes N-oxides and salts thereof) and reference to “a compound of Formula 1” includes the definitions of substituents specified in the Summary of the Invention unless further defined in the Embodiments:
Embodiment 1
A compound of Formula 1 wherein —Y1═Y2—Y3═Y4— including the nitrogen to which Y1 and Y4 are both attached is selected from




Embodiment 2
A compound of Embodiment 1 wherein —Y1═Y2—Y3═Y4— including the nitrogen to which Y1 and Y4 are both attached is selected from Q-2, Q-3, Q-4 and Q-5.
Embodiment 3
A compound of Embodiment 2 wherein —Y1═Y2—Y3═Y4— including the nitrogen to which Y1 and Y4 are both attached is selected from Q-2 and Q-5.
Embodiment 4
A compound of Embodiment 3 wherein —Y1═Y2—Y3═Y4— including the nitrogen to which Y1 and Y4 are both attached is Q-2.
Embodiment 4a
A compound of Embodiment 4 wherein R1 is hydrogen in the 3 and 5 positions and R1 is other than hydrogen in the 4 position.
Embodiment 5
A compound of Embodiment 3 wherein —Y1═Y2—Y3═Y4— including the nitrogen to which Y1 and Y4 are both attached is Q-5.
Embodiment 5a
A compound of Embodiment 5 wherein R1 is hydrogen in the 5 position and R1 is other than hydrogen in the 4 position.
Embodiment 6
A compound of Formula 1 or any one of Embodiments 1 through 5a either alone or in combination, wherein Z is O.
Embodiment 7
A compound of Formula 1 or any one of Embodiments 1 through 6 either alone or in combination, wherein each R1 is independently hydrogen, halogen, cyano, SF5, CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 cyanoalkyl, C2-C4 alkylthioalkyl, SOnR1A, Si(CH3)3 or B(—OC(R1B)2C(R1B)2O—).
Embodiment 8
A compound of Embodiment 7 wherein each R1 is independently hydrogen, halogen, cyano, CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C4 alkylthioalkyl or SOnR1A.
Embodiment 9
A compound of Embodiment 8 wherein each R1 is independently hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy or SOnR1A.
Embodiment 10
A compound of Embodiment 9 wherein each R1 is independently hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl or C1-C4 haloalkoxy.
Embodiment 11
A compound of Embodiment 10 wherein each R1 is independently hydrogen, halogen, C1-C4 haloalkyl or C1-C4 haloalkoxy.
Embodiment 11a
A compound of Embodiment 11 wherein each R1 is independently hydrogen, halogen or C1-C4 haloalkyl.
Embodiment 12
A compound of Formula 1 or any one of Embodiments 1 through 11a either alone or in combination, wherein R2 is halogen, C1-C4 alkyl or C1-C4 haloalkyl.
Embodiment 13
A compound of Embodiment 12 wherein R2 is halogen or C1-C4 alkyl.
Embodiment 14
A compound of Embodiment 13 wherein R2 is halogen or CH3.
Embodiment 15
A compound of Embodiment 14 wherein R2 is halogen.
Embodiment 16
A compound of Embodiment 15 wherein R2 is F, Cl or Br.
Embodiment 17
A compound of Formula 1 or any one of Embodiments 1 through 16 either alone or in combination, wherein m is 0, 1 or 2.
Embodiment 18
A compound of Embodiment 17 wherein m is 0 or 1.
Embodiment 19
A compound of Embodiment 18 wherein m is 1.
Embodiment 20
A compound of Embodiment 18 wherein m is 0 (i.e. the 3-, 4-, 5- and 6-positions are unsubstituted by R3).
Embodiment 21
A compound of Formula 1 or any one of Embodiments 1 through 20 either alone or in combination, wherein each R3 is independently halogen, cyano, CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C8 alkylcycloalkyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C4 alkylcarbonyloxy, C2-C6 cyanoalkyl, C(═O)N(R3A)(R3B), C(═NOR3C)H, SOnR3E; or a phenyl ring optionally substituted with up to 5 substituents independently selected from R3F; or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R3F on carbon atom ring members and R3G on nitrogen atom ring members.
Embodiment 22
A compound of Embodiment 21 wherein each R3 is independently halogen, cyano, CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 cyanoalkyl, SOnR3E; or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R3F on carbon atom ring members and R3G on nitrogen atom ring members.
Embodiment 23
A compound of Embodiment 22 wherein each R3 is independently halogen, cyano, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C6 alkoxyalkyl or C2-C6 haloalkoxyalkyl.
Embodiment 24
A compound of Embodiment 23 wherein each R3 is independently halogen, cyano, C1-C4 alkyl or C1-C4 haloalkyl.
Embodiment 25
A compound of Embodiment 24 wherein each R3 is independently halogen or cyano.
Embodiment 26
A compound of Formula 1 or any one of Embodiments 1 through 25 either alone or in combination, wherein each R3 is attached to the remainder of Formula 1 at the 3-, 4- or 6-position.
Embodiment 27
A compound of Embodiment 26 wherein each R3 is attached to the remainder of Formula 1 at the 3- or 4-position.
Embodiment 28
A compound of Embodiment 27 wherein R3 is attached to the remainder of Formula 1 at the 3-position.
Embodiment 29
A compound of Formula 1 or any one of Embodiments 1 through 28 either alone or in combination, wherein each R1A is independently C1-C4 alkyl or C1-C4 haloalkyl.
Embodiment 30
A compound of Embodiment 29 wherein each R1A is independently C1-C4 haloalkyl.
Embodiment 31
A compound of Formula 1 or any one of Embodiments 1 through 30 either alone or in combination, wherein each R3E is independently C1-C4 alkyl.
Embodiment 32
A compound of Formula 1 or any one of Embodiments 1 through 31 either alone or in combination, wherein each R3A is independently C1-C4 alkyl.
Embodiment 33
A compound of Formula 1 or any one of Embodiments 1 through 32 either alone or in combination, wherein each R3B is independently H or C1-C4 alkyl.
Embodiment 34
A compound of Formula 1 or any one of Embodiments 1 through 33 either alone or in combination, wherein each R3C is independently H or C1-C4 alkyl.
Embodiment 35
A compound of Formula 1 or any one of Embodiments 1 through 34 either alone or in combination, wherein each R3D is independently H or C1-C4 alkyl.
Embodiment 36
A compound of Formula 1 or any one of Embodiments 1 through 35 either alone or in combination, wherein each n is independently 0 or 2.
Embodiment 37
A compound of Embodiment 36 wherein n is 2.
Embodiment 38
A compound of Embodiment 36 wherein n is 0.
Embodiments of the present invention as described in the Summary of the Invention also include the following:
Embodiment 1P
A compound of Formula 1 (including all stereoisomers), N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides as described in the Summary of the Invention.
Embodiment 2P
A compound of Embodiment 1 wherein each Y1 and Y4 is independently N or CR1; and each Y2 and Y3 is CR1; or

    
    
        each Y1 and Y3 is independently N or CR1; and each Y2 and Y4 is CR1.
    
    


Embodiment 3P
A compound of Embodiment 2 wherein Y1 is N or CR1; and each Y2, Y3 and Y4 is CR1.
Embodiment 4P
A compound of Embodiment 2 wherein Y3 is N; and each Y1, Y2 and Y4 is CR1.
Embodiment 5P
A compound of Embodiment 3 wherein Y1 is N; and each Y2, Y3 and Y4 is CR1.
Embodiment 6P
A compound of Embodiment 5 wherein Y1 is N; and each Y2 and Y4 is CH; and Y3 is CR1.
Embodiment 7P
A compound of Embodiment 1 wherein —Y1═Y2—Y3═Y4— (including the nitrogen to which Y1 and Y4 are both attached) is selected from




    
    
        p is 0, 1, 2, 3 or 4;
        q is 0, 1, 2 or 3;
        r is 0, 1 or 2; and
        s is 0 or 1.
    
    


Embodiment 8P
A compound of Embodiment 7 wherein —Y1═Y2—Y3═Y4— (including the nitrogen to which Y1 and Y4 are both attached) is selected from Q-2, Q-3 and Q-4; q is 0, 1 or 2; and r is 0 or 1.
Embodiment 9P
A compound of Embodiment 8 wherein —Y1═Y2—Y3═Y4— (including the nitrogen to which Y1 and Y4 are both attached) is selected from Q-2 and Q-3; and q is 1 or 2.
Embodiment 10P
A compound of Embodiment 9 wherein —Y1═Y2—Y3═Y4— (including the nitrogen to which Y1 and Y4 are both attached) is Q-2.
Embodiment 11P
A compound of Embodiment 10 wherein —Y1═Y2—Y3═Y4— (including the nitrogen to which Y1 and Y4 are both attached) is Q-2; and q is 1.
Embodiment 12P
A compound of any one of Embodiments 7 through 11 wherein each n is independently 0 or 2.
Embodiment 13P
A compound of Embodiment 12 wherein n is 2.
Embodiment 14P
A compound of Embodiment 12 wherein n is 0.
Embodiment 15P
A compound of any one of Embodiments 1 through 14 wherein Z is O.
Embodiment 16P
A compound of any one of Embodiments 1 through 15 wherein R1 is halogen, cyano, CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkyl, C1-C4 haloalkoxy C2-C4 alkoxyalkyl, C2-C4 alkylthioalkyl or SOnR1A.
Embodiment 17P
A compound of Embodiment 16 wherein R1 is halogen, cyano, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl or SCF3.
Embodiment 18P
A compound of Embodiment 17 wherein R1 is halogen, C1-C4 alkyl or C1-C4 haloalkyl.
Embodiment 19P
A compound of Embodiment 18 wherein R1 is halogen or C1-C4 haloalkyl.
Embodiment 20P
A compound of any one of Embodiments 1 through 19 wherein R2 is halogen, C1-C4 alkyl or C1-C4 haloalkyl.
Embodiment 21P
A compound of Embodiment 20 wherein R2 is halogen or C1-C4 alkyl.
Embodiment 22P
A compound of Embodiment 21 wherein R2 is halogen or CH3.
Embodiment 23P
A compound of Embodiment 22 wherein R2 is halogen.
Embodiment 24P
A compound of Embodiment 23 wherein R2 is F, Cl or Br.
Embodiment 25P
A compound of any one of Embodiments 1 through 24 wherein m is 0, 1 or 2.
Embodiment 26P
A compound of Embodiment 25 wherein m is 0 or 1.
Embodiment 27P
A compound of Embodiment 26 wherein m is 1.
Embodiment 28P
A compound of any one of Embodiments 1 through 24 wherein m is 0 (i.e. the 3-, 4-, 5- and 6-positions are unsubstituted by R3).
Embodiment 29P
A compound of any one of Embodiments 1 through 27 wherein each R3 is independently halogen, cyano, hydroxy, nitro, amino, CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C(═O)N(R3A)(R3B), C(═NOR3C)H, C(═N)(R3D)H, C1-C4 alkoxy, C2-C4 cyanoalkoxy, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl, C2-C4 alkylcarbonyloxy, C2-C4 alkoxyalkyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, SOnR3E or C3-C6 cycloalkyl.
Embodiment 30P
A compound of Embodiment 29 wherein each R3 is independently halogen, cyano, amino, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C2-C4 alkoxycarbonyl, C2-C4 alkylcarbonyloxy, C2-C4 alkoxyalkyl or C1-C4 haloalkyl.
Embodiment 31P
A compound of Embodiment 30 wherein each R3 is independently halogen, cyano, amino or C1-C4 alkyl.
Embodiment 32P
A compound of Embodiment 31 wherein each R3 is independently cyano.
Embodiment 33P
A compound of any one of Embodiments 1 through 27 or 29 through 32 wherein each R3 is attached to the remainder of Formula 1 at the 3-, 4- or 6-position.
Embodiment 34P
A compound of Embodiments 33 wherein each R3 is attached to the remainder of Formula 1 at the 3- or 4-position.
Embodiment 35P
A compound of Embodiment 34 wherein R3 is attached to the remainder of Formula 1 at the 3-position.
Embodiment 36P
A compound of any one of Embodiments 1 through 16 or 20 through 25 wherein R1A is C1-C4 alkyl or C1-C4 haloalkyl.
Embodiment 37P
A compound of Embodiment 36 wherein R1A is C1-C4 haloalkyl.
Embodiment 38P
A compound of any one of Embodiments 1 through 29 or 33 through 37 wherein R3E is C1-C4 alkyl.
Embodiment 39P
A compound of any one of Embodiments 1 through 38 wherein R3A is C1-C4 alkyl.
Embodiment 40P
A compound of any one of Embodiments 1 through 39 wherein R3B is H or C1-C4 alkyl.
Embodiment 41P
A compound of any one of Embodiments 1 through 40 wherein R3C is H or C1-C4 alkyl.
Embodiment 42P
A compound of any one of Embodiments 1 through 41 wherein R3D is H or C1-C4 alkyl.
Embodiments of this invention, including Embodiments 1-38 and 1P-42P above as well as any other embodiments described herein, can be combined in any manner, and the descriptions of variables in the embodiments pertain not only to the a compound of Formula 1 but also to the starting compounds and intermediate compounds useful for preparing the compounds of Formula 1. In addition, embodiments of this invention, including Embodiments 1-38 and 1P-42P above as well as any other embodiments described herein, and any combination thereof, pertain to the compositions and methods of the present invention.
Embodiment AAA
A compound of Formula 1 wherein

    
    
        each Y1, Y2, Y3 and Y4 is independently N or CR1, provided no more than 3 of Y1, Y2, Y3 and Y4 are N;
        Z is O or S;
        R1 is halogen, cyano, CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C2-C4 alkylthioalkyl, SOnR1A, C3-C6 cycloalkyl, phenyl or pyridyl;
        R2 is halogen, cyano, nitro, C1-C4 alkoxy, C1-C4 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, SOnR2A or C1-C4 haloalkyl;
        m is 0, 1, 2 or 3;
        each R3 is independently halogen, cyano, hydroxy, nitro, amino, CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C(═O)N(R3A)(R3B), C(═NOR3C)H, C(═N)(R3D)H, C1-C4 alkoxy, C2-C4 cyanoalkoxy, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl, C2-C4 alkylcarbonyloxy, C2-C4 alkoxyalkyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, SOnR3E or C3-C6 cycloalkyl; or phenyl optionally substituted with cyano, halogen or C1-C4 alkyl;
        each n is independently 0, 1 or 2;
        each R1A, R2A and R3E is independently C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkylamino or C2-C6 dialkylamino;
        R3A is C1-C4 alkyl or C1-C4 haloalkyl;
        R3B is H, C1-C4 alkyl or C1-C4 haloalkyl;
        R3C is H or C1-C4 alkyl; and
        R3D is H or C1-C4 alkyl
        provided when i) Y1 is N; Y2 is CH; Y3 is CBr; Y4 is CH; and R2 is Cl, then R3 is other than 5-CF3, 5-CN and 5-NO2; ii) Y1 is N; Y2 is CH; Y3 is CBr; Y4 is CH; and R2 is Br, then R3 is other than 5-CF3; and iii) Y1 is N; Y2 is CCH3; Y3 is CCl; Y4 is CCl; and R2 is Cl, then m is other than 0.
    
    


Embodiment AA
A compound of Embodiment A or a compound of Formula 1 as described in the Summary of the Invention wherein

    
    
        each Y1, Y2, Y3 and Y4 is independently N or CR1, provided no more than 3 of Y1, Y2, Y3 and Y4 are N;
        Z is O or S;
        each R1 is independently hydrogen, halogen, cyano, nitro, SF5, CHO, C(═O)NH2, C(═S)NH2, SO2NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C8 alkylcycloalkyl, C4-C8 cycloalkylalkyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C3-C7 cycloalkylcarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C4-C8 cycloalkylalkoxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkoxyhaloalkyl, C2-C6 alkoxyalkoxy, C2-C4 alkylcarbonyloxy, C2-C6 cyanoalkyl, C2-C6 cyanoalkoxy, C2-C4 alkylthioalkyl, SOnR1A, Si(CH3)3 or B(—OC(R1B)2C(R1B)2O—); or a phenyl ring optionally substituted with up to 5 substituents independently selected from R1C; or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R1C on carbon atom ring members and R1D on nitrogen atom ring members;
        R2 is halogen, cyano, nitro, C1-C4 alkoxy, C1-C4 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, SOnR2A, C1-C4 haloalkyl or C3-C6 cycloalkyl;
        m is 0, 1, 2 or 3;
        each R3 is independently halogen, cyano, hydroxy, nitro, amino, CHO, C(═O)NH2, C(═S)NH2, SO2NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C8 alkylcycloalkyl, C4-C8 cycloalkylalkyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C3-C7 cycloalkylcarbonyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C4-C8 cycloalkylalkoxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkoxyhaloalkyl, C2-C6 alkoxyalkoxy, C2-C4 alkylcarbonyloxy, C2-C6 cyanoalkyl, C2-C6 cyanoalkoxy, C2-C4 alkylthioalkyl, Si(CH3)3, C≡CSi(CH3)3, C(═O)N(R3A)(R3B), C(═NOR3C)H, C(═NR3D)H, SOnR3E; or a phenyl ring optionally substituted with up to 5 substituents independently selected from R3F; or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R3F on carbon atom ring members and R3G on nitrogen atom ring members; or pyrimidinyloxy;
        each n is independently 0, 1 or 2;
        each R1A, R2A and R3E is independently C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkylamino or C2-C6 dialkylamino;
        each R1B is independently H or C1-C4 alkyl;
        each R1C is independently hydroxy, halogen, cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy;
        each R1D is independently cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C2-C6 alkylcarbonyl;
        each R3A is independently C1-C4 alkyl or C1-C4 haloalkyl;
        each R3B is independently H, C1-C4 alkyl or C1-C4 haloalkyl;
        each R3C is independently H or C1-C4 alkyl;
        each R3D is independently H, amino, C1-C4 alkyl or C1-C4 alkylamino;
        each R3F is independently hydroxy, halogen, cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; and
        each R3G is independently cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C2-C6 alkylcarbonyl;
        provided when i) Y1 is N; Y2 is CH; Y3 is CBr; Y4 is CH; and R2 is Cl, then R3 is other than 5-CF3, 5-CN or 5-NO2; ii) Y1 is N; Y2 is CH; Y3 is CBr; Y4 is CH; and R2 is Br, then R3 is other than 5-CF3; and iii) Y1 is N; Y2 is CCH3; Y3 is CCl; Y4 is CCl; and R2 is Cl, then m is other than 0.
    
    


Embodiment A
A compound of Embodiment AA wherein

    
    
        —Y1═Y2—Y3═Y4— including the nitrogen to which Y1 and Y4 are both attached is selected from
    
    






    
    
        Z is O;
        each R1 is independently hydrogen, halogen, cyano, SF5, CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 cyanoalkyl, C2-C4 alkylthioalkyl, SOnR1A, Si(CH3)3 or B(—OC(R1B)2C(R1B)2O—);
        R2 is halogen, C1-C4 alkyl or C1-C4 haloalkyl;
        each R3 is independently halogen, cyano, CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C8 alkylcycloalkyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C4 alkylcarbonyloxy, C2-C6 cyanoalkyl, C(═O)N(R3A)(R3B), C(═NOR3C)H, SOnR3E; or a phenyl ring optionally substituted with up to 5 substituents independently selected from R3F; or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R3F on carbon atom ring members and R3G on nitrogen atom ring members; and
        m is 0, 1 or 2.
    
    


Embodiment B
A compound of Embodiment A wherein

    
    
        —Y1═Y2—Y3═Y4— including the nitrogen to which Y1 and Y4 are both attached is selected from Q-2 and Q-5.
        each R1 is independently hydrogen, halogen, cyano, CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C4 alkylthioalkyl or SOnR1A;
        R2 is halogen or C1-C4 alkyl;
        each R3 is independently halogen, cyano, CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 cyanoalkyl, SOnR3E; or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R3F on carbon atom ring members and R3G on nitrogen atom ring members; and
        m is 0 or 1.
    
    


Embodiment C
A compound of Embodiment B wherein

    
    
        each R1 is independently hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy or SOnR1A;
        R2 is halogen or CH3;
        each R3 is independently halogen, cyano, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C6 alkoxyalkyl or C2-C6 haloalkoxyalkyl; and
        each R1A is independently C1-C4 alkyl or C1-C4 haloalkyl.
    
    


Embodiment D
A compound of Embodiment C wherein

    
    
        —Y1═Y2—Y3═Y4— including the nitrogen to which Y1 and Y4 are both attached is Q-2;
        each R1 is independently hydrogen, halogen, C1-C4 haloalkyl or C1-C4 haloalkoxy; and
        each R3 is independently halogen, cyano, C1-C4 alkyl or C1-C4 haloalkyl.
    
    


Embodiment E
A compound of Embodiment C wherein

    
    
        —Y1═Y2—Y3═Y4— including the nitrogen to which Y1 and Y4 are both attached is Q-5;
        each R1 is independently hydrogen, halogen, C1-C4 haloalkyl or C1-C4 haloalkoxy; and
        each R3 is independently halogen, cyano, C1-C4 alkyl or C1-C4 haloalkyl.
    
    


Specific embodiments include compounds of Formula 1 selected from the group consisting of:

    5-chloro-2-[2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]phenoxy]pyrimidine (Compound 2),
    5-bromo-2-[2-(4-chloro-1H-pyrazol-1-yl)phenoxy]pyrimidine (Compound 5),
    2-[2-(4-bromo-1H-pyrazol-1-yl)phenoxy]-5-chloropyrimidine (Compound 7),
    2-[2-(4-bromo-1H-pyrazol-1-yl)phenoxy]-5-fluoropyrimidine (Compound 10),
    5-bromo-2-[2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]phenoxy]pyrimidine (Compound 18),
    2-(4-bromo-1H-pyrazol-1-yl)-3-[(5-chloro-2-pyrimidinyl)oxy]benzonitrile (Compound 52),
    2-[2-(4-bromo-2H-1,2,3-triazol-2-yl)phenoxy]-5-chloropyrimidine (Compound 54),
    3[(5-chloro-2-pyrimidinyl)oxy]-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]benzonitrile (Compound 58),
    3-[(5-bromo-2-pyrimidinyl)oxy]-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]benzonitrile (Compound 59),
    5-chloro-2-[2-[4-(difluoromethyl)-1H-1,2,3-triazol-1-yl]-3-fluorophenoxy]pyrimidine (Compound 141),
    5-chloro-2-[2-[4-(trifluoromethyl)-1H-1,2,3-triazol-1-yl]phenoxy]pyrimidine (Compound 166),
    5-chloro-2-[2-[4-(difluoromethyl)-1H-1,2,3-triazol-1-yl]phenoxy]pyrimidine (Compound 147),
    3-[(5-fluoro-2-pyrimidinyl)oxy]-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]benzonitrile (Compound 79),
    2-[2-(4-bromo-1H-pyrazol-1-yl)-3-fluorophenoxy]-5-chloropyrimidine (Compound 178),
    3-[(5-chloro-2-pyrimidinyl)oxy]-2-[4-(2,2,2-trifluoroethoxy)-1H-pyrazol-1-yl]benzonitrile (Compound 274),
    5-chloro-2-[2-[4-(2,2,2-trifluoroethoxy)-1H-pyrazol-1-yl]phenoxy]pyrimidine (Compound 138),
    2-[2-(4-bromo-1H-pyrazol-1-yl)-3-(difluoromethyl)phenoxy]-5-chloropyrimidine (Compound 194),
    3-[(5-chloro-2-pyrimidinyl)oxy]-2-[4-(difluoromethyl)-1H-pyrazol-1-yl]benzonitrile (Compound 253),
    3-[(5-chloro-2-pyrimidinyl)oxy]-2-[4-(trifluoromethyl)-1H-imidazol-1-yl]benzonitrile (Compound 252),
    5-bromo-2-[2-[4-(difluoromethyl)-1H-1,2,3-triazol-1-yl]-3-fluorophenoxy]pyrimidine (Compound 305) and
    5-chloro-2-[3-fluoro-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]phenoxy]pyrimidine.


Embodiments of the present invention as described in the Summary of the Invention also include the following:
Embodiment Ap
A compound of the Summary of the Invention wherein

    
    
        each Y1 and Y4 is independently N or CR1; and each Y2 and Y3 is CR1; or
        each Y1 and Y3 is independently N or CR1; and each Y2 and Y4 is CR1;
        R1 is halogen, cyano, CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkyl, C1-C4 haloalkoxy C2-C4 alkoxyalkyl, C2-C4 alkylthioalkyl or SOnR1A;
        R2 is halogen, C1-C4 alkyl or C1-C4 haloalkyl;
        m is 0, 1 or 2;
        each R3 is independently halogen, cyano, hydroxy, nitro, amino, CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C(═O)N(R3A)(R3B), C(═NOR3C)H, C(═N)(R3D)H, C1-C4 alkoxy, C2-C4 cyanoalkoxy, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl, C2-C4 alkylcarbonyloxy, C2-C4 alkoxyalkyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, SOnR3E or C3-C6 cycloalkyl;
        each R3 is attached to the remainder of Formula 1 at the 3-, 4- or 6-position;
        each n is independently 0 or 2;
        R1A is C1-C4 alkyl or C1-C4 haloalkyl;
        R3E is C1-C4 alkyl;
        R3A is C1-C4 alkyl;
        R3B is H or C1-C4 alkyl;
        R3C is H or C1-C4 alkyl; and
        R3D is H or C1-C4 alkyl.
    
    


Embodiment Bp
A compound of Embodiment A wherein

    
    
        Y1 is N or CR1; and each Y2, Y3 and Y4 is CR1;
        Z is O;
        R1 is halogen, cyano, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl or SCF3;
        R2 is halogen or C1-C4 alkyl;
        m is 0 or 1;
        each R3 is independently halogen, cyano, amino, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C2-C4 alkoxycarbonyl, C2-C4 alkylcarbonyloxy, C2-C4 alkoxyalkyl or C1-C4 haloalkyl; and
        each R3 is attached to the remainder of Formula 1 at the 3- or 4-position.
    
    


Embodiment Cp
A compound of Embodiment B wherein

    
    
        Y1 is N; and each Y2, Y3 and Y4 is CR1;
        R1 is halogen, C1-C4 alkyl or C1-C4 haloalkyl;
        R2 is halogen or CH3;
        m is 1;
        R3 is independently halogen, cyano, amino or C1-C4 alkyl; and
        R3 is attached to the remainder of Formula 1 at the 3-position.
    
    


Embodiment Dp
A compound of Embodiment B wherein

    
    
        Y1 is N; and each Y2 and Y4 is CH; and Y3 is CR1;
        R1 is halogen or C1-C4 haloalkyl;
        R2 is halogen; and
        m is 0.
    
    


Specific embodiments include compounds of Formula 1 selected from the group consisting of:

    5-chloro-2-[2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]phenoxy]pyrimidine Compound 2);
    5-bromo-2-[2-(4-chloro-1H-pyrazol-1-yl)phenoxy]pyrimidine (Compound 5);
    2-[2-(4-bromo-1H-pyrazol-1-yl)phenoxy]-5-chloropyrimidine Compound 7);
    2-[2-(4-bromo-1H-pyrazol-1-yl)phenoxy]-5-fluoropyrimidine (Compound 10);
    5-bromo-2-[2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]phenoxy]pyrimidine (Compound 18);
    2-(4-bromo-1H-pyrazol-1-yl)-3-[(5-chloro-2-pyrimidinyl)oxy]benzonitrile (Compound 52);
    2-[2-(4-bromo-2H-1,2,3-triazol-2-yl)phenoxy]-5-chloropyrimidine (Compound 54);
    3[(5-chloro-2-pyrimidinyl)oxy]-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]benzonitrile (Compound 58); and
    3-[(5-bromo-2-pyrimidinyl)oxy]-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]benzonitrile (Compound 59).


This invention also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation herbicidally effective amounts of the compounds of the invention (e.g., as a composition described herein). Of note as embodiments relating to methods of use are those involving the compounds of embodiments described above. Compounds of the invention are particularly useful for selective control of grass and broadleaf weeds in crops such as wheat, barley, maize, soybean, sunflower, cotton, oilseed rape and rice, and specialty crops such as sugarcane, citrus, fruit and nut crops.
Also noteworthy as embodiments are herbicidal compositions of the present invention comprising the compounds of embodiments described above.
This invention also includes a herbicidal mixture comprising (a) a compound selected from Formula 1, N-oxides, and salts thereof, and (b) at least one additional active ingredient selected from (b1) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3) acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics and (b5) 5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b6) photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitors, (b10) auxin transport inhibitors, (b11) phytoene desaturase (PDS) inhibitors, (b12) 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, (b13) homogentisate solenesyltransererase (HST) inhibitors, (b14) cellulose biosynthesis inhibitors, (b15) other herbicides including mitotic disruptors, organic arsenicals, asulam, bromobutide, cinmethylin, cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol, fosamine, fosamine-ammonium, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and pyributicarb, and (b16) herbicide safeners; and salts of compounds of (b1) through (b16).
“Photosystem II inhibitors” (b1) are chemical compounds that bind to the D-1 protein at the QB-binding niche and thus block electron transport from QA to QB in the chloroplast thylakoid membranes. The electrons blocked from passing through photosystem II are transferred through a series of reactions to form toxic compounds that disrupt cell membranes and cause chloroplast swelling, membrane leakage, and ultimately cellular destruction. The QB-binding niche has three different binding sites: binding site A binds the triazines such as atrazine, triazinones such as hexazinone, and uracils such as bromacil, binding site B binds the phenylureas such as diuron, and binding site C binds benzothiadiazoles such as bentazon, nitriles such as bromoxynil and phenyl-pyridazines such as pyridate. Examples of photosystem II inhibitors include ametryn, amicarbazone, atrazine, bentazon, bromacil, bromofenoxim, bromoxynil, chlorbromuron, chloridazon, chlorotoluron, chloroxuron, cumyluron, cyanazine, daimuron, desmedipham, desmetryn, dimefuron, dimethametryn, diuron, ethidimuron, fenuron, fluometuron, hexazinone, ioxynil, isoproturon, isouron, lenacil, linuron, metamitron, methabenzthiazuron, metobromuron, metoxuron, metribuzin, monolinuron, neburon, pentanochlor, phenmedipham, prometon, prometryn, propanil, propazine, pyridafol, pyridate, siduron, simazine, simetryn, tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn and trietazine.
“AHAS inhibitors” (b2) are chemical compounds that inhibit acetohydroxy acid synthase (AHAS), also known as acetolactate synthase (ALS), and thus kill plants by inhibiting the production of the branched-chain aliphatic amino acids such as valine, leucine and isoleucine, which are required for DNA synthesis and cell growth. Examples of AHAS inhibitors include amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac-sodium, cloransulam-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone-sodium, flumetsulam, flupyrsulfuron-methyl, flupyrsulfuron-sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron-methyl (including sodium salt), iofensulfuron (2-iodo-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide), mesosulfuron-methyl, metazosulfuron (3-chloro-4-(5,6-dihydro-5-methyl-1,4,2-dioxazin-3-yl)-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-1-methyl-1H-pyrazole-5-sulfonamide), metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone-sodium, propyrisulfuron (2-chloro-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-6-propylimidazo[1,2-b]pyridazine-3-sulfonamide), prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone, thifensulfuron-methyl, triafamone (N-[2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1,1-difluoro-N-methylmethanesulfonamide), triasulfuron, tribenuron-methyl, trifloxysulfuron (including sodium salt), triflusulfuron-methyl and tritosulfuron.
“ACCase inhibitors” (b3) are chemical compounds that inhibit the acetyl-CoA carboxylase enzyme, which is responsible for catalyzing an early step in lipid and fatty acid synthesis in plants. Lipids are essential components of cell membranes, and without them, new cells cannot be produced. The inhibition of acetyl CoA carboxylase and the subsequent lack of lipid production leads to losses in cell membrane integrity, especially in regions of active growth such as meristems. Eventually shoot and rhizome growth ceases, and shoot meristems and rhizome buds begin to die back. Examples of ACCase inhibitors include alloxydim, butroxydim, clethodim, clodinafop, cycloxydim, cyhalofop, diclofop, fenoxaprop, fluazifop, haloxyfop, pinoxaden, profoxydim, propaquizafop, quizalofop, sethoxydim, tepraloxydim and tralkoxydim, including resolved forms such as fenoxaprop-P, fluazifop-P, haloxyfop-P and quizalofop-P and ester forms such as clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl and fenoxaprop-P-ethyl.
Auxin is a plant hormone that regulates growth in many plant tissues. “Auxin mimics” (b4) are chemical compounds mimicking the plant growth hormone auxin, thus causing uncontrolled and disorganized growth leading to plant death in susceptible species. Examples of auxin mimics include aminocyclopyrachlor (6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid) and its methyl and ethyl esters and its sodium and potassium salts, aminopyralid, benazolin-ethyl, chloramben, clacyfos, clomeprop, clopyralid, dicamba, 2,4-D, 2,4-DB, dichlorprop, fluroxypyr, halauxifen (4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylic acid), halauxifen-methyl (methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylate), MCPA, MCPB, mecoprop, picloram, quinclorac, quinmerac, 2,3,6-TBA, triclopyr, and methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate.
“EPSP (5-enol-pyruvylshikimate-3-phosphate) synthase inhibitors” (b5) are chemical compounds that inhibit the enzyme, 5-enol-pyruvylshikimate-3-phosphate synthase, which is involved in the synthesis of aromatic amino acids such as tyrosine, tryptophan and phenylalanine. EPSP inhibitor herbicides are readily absorbed through plant foliage and translocated in the phloem to the growing points. Glyphosate is a relatively nonselective postemergence herbicide that belongs to this group. Glyphosate includes esters and salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate).
“Photosystem I electron diverters” (b6) are chemical compounds that accept electrons from Photosystem I, and after several cycles, generate hydroxyl radicals. These radicals are extremely reactive and readily destroy unsaturated lipids, including membrane fatty acids and chlorophyll. This destroys cell membrane integrity, so that cells and organelles “leak”, leading to rapid leaf wilting and desiccation, and eventually to plant death. Examples of this second type of photosynthesis inhibitor include diquat and paraquat.
“PPO inhibitors” (b7) are chemical compounds that inhibit the enzyme protoporphyrinogen oxidase, quickly resulting in formation of highly reactive compounds in plants that rupture cell membranes, causing cell fluids to leak out. Examples of PPO inhibitors include acifluorfen-sodium, azafenidin, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil (methyl N-[2-[[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]thio]-1-oxopropyl]-β-alaninate) and 3-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propyn-1-yl)-2H-1,4-benzoxazin-6-yl]dihydro-1,5-dimethyl-6-thioxo-1,3,5-triazine-2,4(1H,3H)-dione.
“GS (glutamine synthase) inhibitors” (b8) are chemical compounds that inhibit the activity of the glutamine synthetase enzyme, which plants use to convert ammonia into glutamine. Consequently, ammonia accumulates and glutamine levels decrease. Plant damage probably occurs due to the combined effects of ammonia toxicity and deficiency of amino acids required for other metabolic processes. The GS inhibitors include glufosinate and its esters and salts such as glufosinate-ammonium and other phosphinothricin derivatives, glufosinate-P ((2S)-2-amino-4-(hydroxymethylphosphinyl)butanoic acid) and bilanaphos.
“VLCFA (very long chain fatty acid) elongase inhibitors” (b9) are herbicides having a wide variety of chemical structures, which inhibit the elongase. Elongase is one of the enzymes located in or near chloroplasts which are involved in biosynthesis of VLCFAs. In plants, very-long-chain fatty acids are the main constituents of hydrophobic polymers that prevent desiccation at the leaf surface and provide stability to pollen grains. Such herbicides include acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor, dimethenamid, diphenamid, fenoxasulfone (3-[[(2,5-dichloro-4-ethoxyphenyl)methyl]sulfonyl]-4,5-dihydro-5,5-dimethylisoxazole), fentrazamide, flufenacet, indanofan, mefenacet, metazachlor, metolachlor, naproanilide, napropamide, napropamide-M ((2R)—N,N-diethyl-2-(1-naphthalenyloxy)propanamide), pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone, and thenylchlor, including resolved forms such as S-metolachlor and chloroacetamides and oxyacetamides.
“Auxin transport inhibitors” (b10) are chemical substances that inhibit auxin transport in plants, such as by binding with an auxin-carrier protein. Examples of auxin transport inhibitors include diflufenzopyr, naptalam (also known as N-(1-naphthyl)phthalamic acid and 2-[(1-naphthalenylamino)carbonyl]benzoic acid).
“PDS (phytoene desaturase inhibitors) (b11) are chemical compounds that inhibit carotenoid biosynthesis pathway at the phytoene desaturase step. Examples of PDS inhibitors include beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone norflurzon and picolinafen.
“HPPD (4-hydroxyphenyl-pyruvate dioxygenase) inhibitors” (b12) are chemical substances that inhibit the biosynthesis of synthesis of 4-hydroxyphenyl-pyruvate dioxygenase. Examples of HPPD inhibitors include benzobicyclon, benzofenap, bicyclopyrone (4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridinyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one), fenquinotrione (2-[[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxo-2-quinoxalinyl]carbonyl]-1,3-cyclohexanedione), isoxachlortole, isoxaflutole, mesotrione, pyrasulfotol, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, topramezone, 5-chloro-3-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone, 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione, 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-(3-methoxyphenyl)-3-(3-methoxypropyl)-4(3H)-pyrimidinone, 2-methyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide and 2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide.
HST (homogentisate solenesyltransererase) inhibitors (b13) disrupt a plant's ability to convert homogentisate to 2-methyl-6-solanyl-1,4-benzoquinone, thereby disrupting carotenoid biosynthesis. Examples of HST inhibitors include haloxydine, pyriclor, 3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthyridin-2(1H)-one, dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-b]pyrazin-6(5H)-one and 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone.
HST inhibitors also include compounds of Formulae A and B.




    wherein Rd1 is H, Cl or CF3; Rd2 is H, Cl or Br; Rd3 is H or Cl; Rd4 is H, Cl or CF3; Rd5 is CH3, CH2CH3 or CH2CHF2; and Rd6 is OH, or —OC(═O)-i-Pr; and Re1 is H, F, Cl, CH3 or CH2CH3; Re2 is H or CF3; Re3 is H, CH3 or CH2CH3; Re4 is H, F or Br; Re5 is Cl, CH3, CF3, OCF3 or CH2CH3; Re6 is H, CH3, CH2CHF2 or C≡CH; Re7 is OH, —OC(═O)Et, —OC(═O)-i-Pr or —OC(═O)-t-Bu; and Ae8 is N or CH.


Cellulose biosynthesis inhibitors (b14) inhibit the biosynthesis of cellulose in certain plants. They are most effective when using a pre-application or early post-application on young or rapidly growing plants. Examples of cellulose biosynthesis inhibitors include chlorthiamid, dichlobenil, flupoxam, indaziflam (N2-[(1R,2S)-2,3-dihydro-2,6-dimethyl-1H-inden-1-yl]-6-(1-fluoroethyl)-1,3,5-triazine-2,4-diamine), isoxaben and triaziflam.
Other herbicides (b15) include herbicides that act through a variety of different modes of action such as mitotic disruptors (e.g., flamprop-M-methyl and flamprop-M-isopropyl) organic arsenicals (e.g., DSMA, and MSMA), 7,8-dihydropteroate synthase inhibitors, chloroplast isoprenoid synthesis inhibitors and cell-wall biosynthesis inhibitors. Other herbicides include those herbicides having unknown modes of action or do not fall into a specific category listed in (b1) through (b14) or act through a combination of modes of action listed above. Examples of other herbicides include aclonifen, asulam, amitrole, bromobutide, cinmethylin, clomazone, cumyluron, cyclopyrimorate (6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 4-morpholinecarboxylate), daimuron, difenzoquat, etobenzanid, fluometuron, flurenol, fosamine, fosamine-ammonium, dazomet, dymron, ipfencarbazone (1-(2,4-dichlorophenyl)-N-(2,4-difluorophenyl)-1,5-dihydro-N-(1-methylethyl)-5-oxo-4H-1,2,4-triazole-4-carboxamide), metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb and 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole.
“Herbicide safeners” (b16) are substances added to a herbicide formulation to eliminate or reduce phytotoxic effects of the herbicide to certain crops. These compounds protect crops from injury by herbicides but typically do not prevent the herbicide from controlling undesired vegetation. Examples of herbicide safeners include but are not limited to benoxacor, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone, naphthalic anhydride, oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide and N-(aminocarbonyl)-2-fluorobenzenesulfonamide, 1-bromo-4-[(chloromethyl)sulfonyl]benzene, 2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), 4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660).
One or more of the following methods and variations as described in Schemes 1-14 can be used to prepare a compound of Formula 1. The definitions of Y1, Y2, Y3 Y4, R1, R2 and R3 in the compounds of Formulae 1-14 below are as defined above in the Summary of the Invention unless otherwise noted. Compounds of Formulae 1A through 1H, 2A through 2L, 4A and 6A are various subsets of a compound of Formulae 1, 2, 4 and 6, and all substituents for Formulae 1, 2, 4 and 6 are as defined above for Formula 1 unless otherwise noted.
As shown in Scheme 1 a compound of Formula 1 can be prepared by nucleophilic substitution by heating a compound of Formula 2 in a suitable solvent, such as acetonitrile, tetrahydrofuran or N,N-dimethylformamide in the presence of a base such as potassium or cesium carbonate, with a compound of Formula 3, (where LG is halogen or SO2Me). The reaction is typically conducted at temperatures ranging from 50 to 110° C.




As shown in Scheme 2, a compound of Formula 2A (i.e. a compound of Formula 2 wherein Z is O; and RA is H or lower alkyl) can be prepared using a Buchwald copper(I) catalyzed carbon-nitrogen bond forming reaction in the presence of a ligand such as ethylene diamine or cyclohexane diamine by heating a compound of Formula 4 (wherein X is I or Br) in a suitable solvent, such as toluene, 1,4-dioxanes or N,N-dimethylformamide in the presence of a base such as potassium carbonate, cesium carbonate or tribasic potassium phosphate, with a compound of Formula 5. The reaction is typically conducted at about 110° C. as described for copper-catalyzed carbon-nitrogen bond formation methods using diamine ligands found in Surry and Buchwald, Chemical Science 2010, 1, 13-31. One skilled in the art can prepare a compound of Formula 5 by means found in Comprehensive Heterocyclic Chemistry, Part II, 1996, parts 2, 3 & 4, Pergamon Press, publisher, edited by Alan. R. Katritzky & Charles W. Reese and CHC, Part I, 1984 and series of The Chemistry of Heterocyclic Compounds, 1981, publisher John Wiley & sons and Interscience Publishers Inc, 1953.




Phosphine ligands can also be employed for palladium-catalyzed amination reactions to prepare a compound of Formula 2A. A review of suitable ligands, bases, solvents, catalysts and substrates for use with NH-containing heterocycles (i.e. a compound of Formula 5) can be found in Surry and Buchwald, Chemical Science 2011, 2, 27-50 and references cited therein. In particular, conditions for pyrazoles and imidazoles with aryl or heteroaryl halides using a palladium catalyst such as Pd2(dba)3, with ligands such as 2-di-t-butylphophino-2′,4′,6′-triisopropylbiphenyl (i.e. t-Bu-X-Phos) or 2-di-t-butylphophino-3,4,5,6-tetramethyl-2′,4′,6′-triisopropylbiphenyl (i.e. Me4-t-Bu-X-Phos) with bases such as Na+−O-t-Bu or K3PO4 in solvents such as toluene or 1,4-dioxane at temperatures ranging from 60 to 105° C. are described. Alternative synthetic strategies can also be found in Sorokin, Mini-Reviews in Organic Chemistry 2008, 5, 323-330; Bellina and Rossi, Advanced Synthesis & Catalysis 2010, 352, 1223-1276, and Beletskaya and Cheprakov, Organometallics 2012, 31, 7753-7808.

As shown in Scheme 3, a compound of Formula 2B (i.e. a compound of Formula 2 wherein Z is O; and RA is H or lower alkyl) can also be prepared by direct nucleophilic displacement by heating a compound of Formula 4A, (i.e. a compound of Formula 4 wherein X is F or Cl; and R3 is an electron withdrawing group) in a suitable solvent such as N,N-dimethylformamide, N,N-dimethylacetamide or N-methylpyrrolidinone and in the presence of a base such as potassium or cesium carbonate with a compound of Formula 5. The reaction is typically conducted at temperatures ranging from 120 to 160° C. but the transformation can be accomplished at higher or lower temperatures depending on the nature of the R3 substituents.




As shown in Scheme 4, a compound of Formula 2C (i.e. a compound of Formula 2 where Z is O) can be prepared by deprotection of a compound of Formula 2D (i.e. a compound of Formula 2A wherein Z is O; and RA is CH3 or —C(═O)CH3) with a suitable deprotecting agent. Suitable methoxy (i.e. when RA is CH3) deprotecting reagents such as BBr3, AlCl3 and HBr in acetic acid can be used in the presence of solvents such as toluene, dichloromethane and dichloroethane at a temperature of from −80 to 120° C. Suitable acetoxy (i.e. when RA is —C(═O)CH3) deprotecting agents include potassium carbonate in methanol or ammonium acetate in aqueous methanol at room temperature can be used as discussed in Biswanath Das, Tetrahedron 2003, 59, 1049-1054 and methods cited therein. Alternatively, a compound of Formula 2D can be combined with Amberlyst 15© in methanol (as discussed in Biswanath Das, Tet. Lett. 2003, 44, 5465-5468) or combined with sodium acetate in ethanol (as discussed in T. Narender, et al. Synthetic Communications 2009, 39(11), 1949-1956. Other useful phenolic protecting groups suitable for use in preparing a compound of Formula 2C can be found in Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 4th ed.; Wiley: Hoboken, N.J., 1991).




As shown in Scheme 5, a compound of Formula 1B, (i.e. a compound of Formula 1 where Z is O; and m is 1 at the 3-position) can be prepared by “C—H activation” of a compound of Formula 1A (a compound of Formula 1 wherein Z is O; and m is 0). For example, palladium(II) acetate along with either an N-halosuccinimide, PhI(OAc)2, N-fluoropyridinium tetrafluoroborate, or a lower alkyl boronic acid can be used to introduce the R3 variable as I, Br, Cl, —OAc, F, and lower alkyl substituents respectively. These methods are detailed in reviews of selective activation of C—H bonds in Chemical Reviews 2010, 110, 575-1211 and references cited therein. Methods for “C—H activation” can also be found in Wencel-Delord et al., Nature Chemistry 2013, 5, 369-375 and a series of reviews of “C—H activiation” in Accounts of Chemical Research 2012, 45, 777-958 and references cited therein.




Chemistry based on “C—H activation” can also be used to prepare a compound of Formulae 2E (i.e. a compound of Formula 2 wherein Z is O; RA is —C(O)CH3; and m is 1 at the 3-position) as shown in Scheme 6 utilizing palladium(II) acetate and (diacetoxyiodo)benzene as described above for Scheme 5. A compound of Formula 2E can subsequently be converted via methods disclosed in Schemes 1 and 4 to provide a compound of Formula 1.




Similarly, chemistry based on “C—H activation” can be used to prepare a compound of Formulae 2F (i.e. a compound of Formula 2A wherein Z is S) as shown in Scheme 7. A compound of Formula 6 can first be converted to a compound of Formula 6A (i.e. a compound of Formula 6 wherein the ortho “H” is X; and X is Br or I) by utilizing a stepwise introduction of substituents using “C—H activation”. Iodides and bromides of Formula 6A can then be further functionalized by copper mediated cross-coupling with thiourea as described in Qi, Junsheng, Chin. J. Chem. 2010, 28, 1441-1443 to provide the aryl thiol after acidic deprotection. Palladium catalyzed cross-coupling reactions of aryl halides can give protected thiols that can, in turn, be deprotected under either acidic conditions or basic conditions (e.g. cesium fluoride) to provide a compound of Formula 2F. These conditions are discussed in Organ, Michael G., Angew. Chem. Int. Ed. 2012, 51, 3314-3322 and the references cited therein. Also, relevant conditions can be found in Takashiro Itoh, J. Org. Chem. 2006, 71, 2203-2206. A compound of Formula 2F can then be converted via methods disclosed in Schemes 1 and 4 to provide a compound of Formula 1. Compounds of Formula 6 are commercially available or can be synthesized by methods described in Heterocycles 2007, 71, 1467-1502 and the references within. See also Lamberth, Org. Prep. Proced. Internat. 2002, 34, 98-102.




As shown in Scheme 8, functionalization of the —Y1═Y2—Y3═Y4— moiety (i.e the 5-membered heterocycle connected to the remainder of Formula 1 through a nitrogen atom) may also be accomplished by means of electrophilic substitution when any one (or all) of Y1, Y2, Y3 and Y4 is CH, to prepare a compound of Formula 1D (i.e. a compound of Formula 1 wherein Z is O; and any one (or all) of R1 is other than H). Similarly, a compound of Formula 2H (a compound of Formula 2A wherein Z is O; and RA is CH3 or —(C═O)CH3). Reagents capable of electrophilic substitution such as N-halosuccinimides, sulfuryl halides and elemental halogens can be used in compatible solvents such as N,N-dimethylformamide or acetonitrile at temperatures from 20 to 120° C. to introduce substituents at reactive positions of the —Y1═Y2—Y3═Y4— moiety.




As shown in Scheme 9, functionalization of the —Y1═Y2—Y3═Y4— moiety (i.e the 5-membered heterocycle connected to the remainder of Formula 1 through nitrogen) may also be accomplished by means of suitable cross-coupling methods as described in V. Snieckus et al., Angew. Chem. Int. Ed. 2012, 51, 5062-5086 or Accounts of Chemical Research 2008, 41, 11, 1439-1564 and references cited therein. These methods involve selection of an appropriate catalyst and reagent system for converting the R1 substituent (i.e. when any one of Y1, Y2, Y3 and Y4 is CR1; and R1 is halogen) utilizing cross-coupling methods to prepare compounds of Formula 1F (i.e. a compound of Formula 1 wherein Z is O; and R1 is other then halogen) or 2J (wherein Z is O; and RA is a suitable protecting group such as CH3 or —C(═O)CH3). Reagents capable of electrophilic substitution such as N-halosuccinimides, sulfuryl halides and halogens can be used in compatible solvents such as N,N-dimethylformamide or acetonitrile at a temperature from 20 to 120° C. to introduce substituents in reactive positions of the —Y1═Y2—Y3═Y4— moiety. The CR1 substituents on the —Y1═Y2—Y3═Y4— moiety may be introduced either before or after the coupling reaction used to form the N-heterocyclic bond discussed in Schemes 2 and 3. For palladium-catalyzed cross coupling reactions suitable for use with these types of heterocycles see Gribble and Li Eds., Palladium in Heterocyclic Chemistry Volume 1, Pergamon Press, 2000, Gribble and Li, Eds., Palladium in Heterocyclic Chemistry Volume 2, Pergamon Press, 2007 and deMeijere and Diederich Eds., Metal-Catalyzed Cross-Coupling Reactions, Second Edition, John Wiley and Sons, 2004.




Products of Formula 2K (a compound of Formula 2 wherein Y1 is N, Y2 is CR1, Y3 is CR1 and Y4 is N) can be prepared by the methods shown in Scheme 10. Phenyl hydrazines of Formula 7 can be reacted with glyoxal in acetic acid followed by hydroxyl amine in ethanol to form arylhydrazone oxime intermediates of Formula 8. Reaction of a compound of Formula 8 in pyridine with a copper salt such as copper sulphate provides the 2-aryltriazole-1-oxide intermediates of Formula 9. Treatment of a compound of Formula 9 with trimethyloxonium tetrafluoroborate yields a 1-methoxy-2-phenyltriazolium salts that can react with R1 nucleophiles (for example halides, cyanides or alkoxides) to produce a compound of Formula 2K, (i.e. a compound of Formula 2 wherein Z is O and RA is a suitable protecting group such as benzyl or CH3). This route can also be used for substituted dicarbonyl compounds or their monooximes in place of glyoxal which result in compounds of Formula 9 where R1 can be various alkyls after reduction of the N-oxide. For specific examples of this sequence with a variety of dicarbonyl compounds and nucleophiles, see M. Begtrup in J. Chem. Society, Perkin Trans. 1 1981, 503-513 and Bull. Soc. Chim. Belg. 1997, 106, 717-727.




In Scheme 11, the phenol, 2L is reacted with N,N-dimethyl thiocarbamoyl chloride in N,N-dimethylformamide in the presence of a strong tertiary amine base such as 1,4-diazabicyclo[2.2.2]octane or N-methylmorpholine for acidic phenols (for less-acidic phenols, prior deprotonation with sodium hydride may be advantageous) to form the O-aryl N,N-dimethylthiocarbamate of Formula 10. Newman-Kwart rearrangement of a compound of Formula 10 at temperatures ranging from 200 to −300° C. provides the intermediate S-aryl dimethylthiocarbamate of Formula 11. A one-pot deprotection of a compound of Formula 11 is readily achieved using 10% aqueous sodium hydroxide or methanolic potassium hydroxide to afford the corresponding aryl thiol. Subsequent reaction with a compound of Formula 3 at or slightly above room temperature provides the product 1G (i.e. a compound of Formula 1 wherein Z is S. Methods for the Newman-Kwart rearrangements are found in Lloyd-Jones, Guy C., Synthesis 2008, 661-689.




As shown in Scheme 12 compounds of Formula 1H (compound of Formula 1 wherein Y1 is N, Y2 is N, Y3 is CR1 and Y4 is CR1) can be prepared by the coupling of an alkyne with an azide of Formula 12. This type of reaction is commonly referred to as ‘click chemistry’ and well known to those skilled in the art. A review of suitable conditions and catalysts for the coupling of alkynes with azides (i.e. a compound of Formula 12) can be found in Meldal and Tornoe in Chemical Reviews 2008, 108, 2952-3015 and references cited therein. Suitable conditions generally include a copper catalyst with ligands such as halides and ascorbate in a variety of organic solvents such as tert-butanol, methanol, dimethylsulfoxide, dimethyl formamide in addition to water. The regioselectivitiy of this coupling can be dependent upon the nature of R1 however this can be controlled with the choice of reaction conditions such as metalating a terminal alkyne. Also note that the two R1 groups on the alkyne need not be identical. For an example see Krasinski, Fokin, and Sharpless in Organic Letters, 2004, 6, 1237-1240.




As shown in Scheme 13, a compound of Formula 12 can be prepared using the same methods as described in Scheme 1.




As shown in Scheme 14 compounds of Formula 13 can be prepared by diazotisation of an amine of Formula 14 followed by substitution with azide using methods well known to those skilled in the art. Descriptions of how this transformation can be achieve are described in Wu, Zhao, Lan, Cao, Liu, Jinag, and Li in The Journal of Organic Chemistry 2012, 77, 4261-4270 or in Barral, Moorhouse, and Moses in Organic Letters 2007, 9, 1809-1811. Examples of suitable reagents for diazotization include sodium nitrite and tert-butyl nitrite, and suitable examples of azide sources include sodium azide and trimethylsilyl azide.




It is recognized by one skilled in the art that various functional groups can be converted into others to provide different a compound of Formula 1. For a valuable resource that illustrates the interconversion of functional groups in a simple and straightforward fashion, see Larock, R. C., Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd Ed., Wiley-VCH, New York, 1999. For example, intermediates for the preparation of a compound of Formula 1 may contain aromatic nitro groups, which can be reduced to amino groups, and then be converted via reactions well known in the art such as the Sandmeyer reaction, to various halides, providing a compound of Formula 1. The above reactions can also in many cases be performed in alternate order
It is recognized that some reagents and reaction conditions described above for preparing a compound of Formula 1 may not be compatible with certain functionalities present in the intermediates. In these instances, the incorporation of protection/deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products. The use and choice of the protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 4th ed.; Wiley: Hoboken, N.J., 1991). One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as it is depicted in any individual scheme, it may be necessary to perform additional routine synthetic steps not described in detail to complete the synthesis of a compound of Formula 1. One skilled in the art will also recognize that it may be necessary to perform a combination of the steps illustrated in the above schemes in an order other than that implied by the particular presented to prepare a compound of Formula 1.
One skilled in the art will also recognize that a compound of Formula 1 and the intermediates described herein can be subjected to various electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.
Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Steps in the following Examples illustrate a procedure for each step in an overall synthetic transformation, and the starting material for each step may not have necessarily been prepared by a particular preparative run whose procedure is described in other Examples or Steps. Percentages are by weight except for chromatographic solvent mixtures or where otherwise indicated. Parts and percentages for chromatographic solvent mixtures are by volume unless otherwise indicated. 1H NMR spectra are reported in ppm downfield from tetramethylsilane in CDCl3; “s” means singlet, “d” means doublet, “t” means triplet, “q” means quartet, “m” means multiplet, “dd” means doublet of doublets, “dt” means doublet of triplets, and “bs” means broad singlet.
Synthesis Example 1
Preparation of 5-chloro-2-[2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]phenoxy]pyrimidine (Compound 2)
Step A: Preparation of 1-(2-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazole
2-Iodoanisole (1.43 g, 6.12 mmol) and 3-(trifluoromethyl)-1H-pyrazole (1.0 g, 7.4 mmol) were combined in 3 mL of p-dioxane under a nitrogen atmosphere. Powdered potassium carbonate (1.78 g, 12.9 mmol), copper(I) iodide (12 mg, 0.0612 mmol) and trans 1,2-diaminocyclohexane (70 mg, 0.61 mmol) were added and the resulting mixture was heated at reflux for 18 h. The reaction mixture was cooled and then diluted with de-ionized water and ethyl acetate and the layers separated. The aqueous layer was extracted with ethyl acetate (2×). The combined organic layers were washed with a saturated aqueous solution of EDTA, brine, then dried over MgSO4, filtered and concentrated to give 2.2 g of oil. Column chromatography through 40 g silica gel using a gradient of hexanes to 11% ethyl acetate in hexanes provided 0.25 g of the title compound as an oil.
1H NMR δ 8.05 (s, 1H), 7.72 (d, 1H), 7.38 (t, 1H), 7.05-7.12 (m, 2H), 6.67 (s, 1H), 3.89 (s, 3H).
Step B: Preparation of 2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]phenol
1-(2-Methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazole (i.e. the product of Step A) (0.21 g, 0.87 mmol) was dissolved in 4.4 mL of dichloromethane under a nitrogen atmosphere. A solution of 1 M solution of boron tribromide in dichloromethane (0.96 mL, 0.96 mmol) was then added dropwise a room temperature. The resulting brown solution was stirred at room temperature for three hours. The solution was then poured into an ice and de-ionized water mixture. The mixture was diluted with dichloromethane and the aqueous layer separated. The aqueous layer was extracted with dichloromethane. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to give 150 mg of the title compound as a solid.
1H NMR δ 10.12 (bs, 1H), 8.04 (d, 1H), 7.40 (d, 1H), 7.28 (t, 1H), 7.15 (d, 1H), 6.97 (t, 1H), 6.78 (d, 1H).
Step C: Preparation of 5-chloro-2-[2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]phenoxy]pyrimidine
2-[3-(Trifluoromethyl)-1H-pyrazol-1-yl]phenol (i.e. the product of Step B), (70 mg, 0.31 mmol) and 2,5-dichloro-pyrimidine (50 mg, 0.337 mmol) were combined in 2 mL of acetonitrile under a nitrogen atmosphere. Powdered potassium carbonate (128 mg, 0.920 mmol) was added and the resulting mixture was heated at reflux for 18 h. The reaction was cooled and diluted with de-ionized water and ethyl acetate. The aqueous layer was separated and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to give 100 mg of a solid. The solid was filtered from hexanes to give 23 mg of the title compound, a compound of the invention.
1H NMR δ 8.39 (s, 2H), 7.93 (s, 1H), 7.81 (d, 1H), 7.48 (t, 1H), 7.42 (t, 1H), 7.35 (d, 1H), 6.58 (s, 1H).
Synthesis Example 2
Preparation of 5-chloro-2-[2-(1H-pyrazol-1-yl)phenoxy]pyrimidine (Compound 12)
Step A: Preparation of 2-(1H-pyrazol-1-yl)-phenol
2-Iodophenol (13.4 g, 60.9 mmol) and 1H-pyrazole (5.0 g, 74 mmol) were dissolved in 30 mL of p-dioxane and 30 mL of toluene under a nitrogen atmosphere. Powdered potassium carbonate (21.0 g, 152 mmol) was added and the reaction mixture was sparged with nitrogen for ten minutes. Copper(I) iodide (2.9 g, 15.22 mmol) and trans 1,2-diaminocyclohexane (3.66 mL, 30.4 mmol) were added sequentially, then the reaction mixture was heated at reflux for 18 h. The cooled reaction mixture was diluted with de-ionized water and ethyl acetate and saturated aqueous EDTA. The aqueous layer separated and extracted twice with ethyl acetate. The combined organic layers were washed twice with saturated aqueous EDTA solution, brine, then dried over MgSO4, filtered and concentrated to give 13 g of a brown solid. Chromatography through 120 gram of silica eluting with 10% ethyl acetate in hexanes provided 5.08 g of the title compound as a liquid.
1H NMR δ 10.12 (s, 1H), 8.04 (d, 1H), 7.39 (d, 1H), 7.26 (t, 1H), 7.15 (d, 1H), 6.97 (t, 1H), 6.79 (d, 1H).
Step B: Preparation of 5-chloro-2-[2-(1H-pyrazol-1-yl)phenoxy]pyrimidine
The title compound was prepared in the same fashion as described in Example 1, Step C, using 2-(1H-pyrazol-1-yl)-phenol (5.08 g, 31.7 mmol) in place of 2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-phenol to give 7.88 g of the title compound, a compound of the invention, as a solid.
1H NMR δ 8.37 (s, 2H), 7.90 (d, 1H), 7.82 (d, 1H), 7.58 (d, 1H), 7.43 (t, 2H), 7.32 (d, 1H), 6.31 (s, 1H).
Synthesis Example 3
Preparation of 2-[2-(4-bromo-1H-pyrazol-1-yl)phenoxy]-5-chloropyrimidine (Compound 7)
Step A: Preparation of 2-[2-(4-bromo-1H-pyrazol-1-yl)phenoxy]-5-chloropyrimidine
To 5-chloro-2-[2-(1H-pyrazol-1-yl)phenoxy]pyrimidine (i.e. the product of Example 2, Step B) (7.88 g, 28.9 mmol) dissolved in 40 mL of N,N-dimethylformamide under a nitrogen atmosphere was added N-bromosuccinimide (5.66 g, 31.8 mmol). The resulting mixture was heated at 80° C. for 18 h. The cooled reaction mixture was diluted with de-ionized water and diethyl ether and the layers separated. The aqueous layer was extracted twice with diethyl ether. The combined organic layers were washed (3×) with de-ionized water, brine then concentrated to give 10.98 g of a solid. The solid was filtered from hexanes to give 8.92 g of the title compound, a compound of the invention.
1H NMR δ 8.41 (s, 2H), 7.94 (s, 1H), 7.77 (d, 1H), 7.55 (s, 1H), 7.42 (m, 2H), 7.32 (d, 1H).
Synthesis Example 4
Preparation of 3-[(5-chloro-2-pyrimidinyl-oxy)]-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]-benzonitrile (Compound 58)
Step A: Preparation of 3-hydroxy-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]benzonitrile
To a solution of 2-fluoro-3-hydroxybenzonitrile (0.92 g, 6.7 mmol) and 4-(trifluoromethyl)-1H-pyrazole (1.0 g, 7.3 mmol) dissolved in 14 mL of N,N-dimethylacetamide under a nitrogen atmosphere was added powdered potassium carbonate (2.78 g, 20.1 mmol). The resulting mixture was then heated at 153° C. for 18 h. The cooled reaction mixture was diluted with de-ionized water and ethyl acetate and the layers separated. The aqueous layer was extracted (4×) with ethyl acetate, and the combined organic layers were washed (3×) with de-ionized water followed by brine. The combined organic layers were dried over MgSO4, filtered and concentrated to give 1.58 g of an oil. Chromatography through 40 g of silica gel eluting with a gradient of 20 to 40% ethyl acetate in hexanes to give 1.37 g of a solid. The solid was filtered from hexanes to give 680 mg of the title compound.
1H NMR δ 9.86 (bs, 1H), 8.64 (s, 1H), 8.07 (s, 1H), 7.40 (m, 2H), 7.37 (m, 1H).
Step B: Preparation of 3-[(5-chloro-2-pyrimidinyl)oxy]-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]benzonitrile
To a stirred mixture of 3-hydroxy-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]benzonitrile (i.e. the product of Example 4, Step A) (0.15 g, 0.592 mmol) and 2,5-dichloropyrimidine (0.10 g, 0.65 mmol) in 1.5 mL of N,N-dimethylformamide under a nitrogen atmosphere was added powdered potassium carbonate (0.25 g, 1.77 mmol). The resulting mixture was heated to 100° C. for approximately 1 h. The cooled reaction mixture was diluted with de-ionized water and diethyl ether and the layers were separated. The aqueous layer was extracted twice with diethyl ether, combined and washed (3×) with de-ionized water followed by brine, then dried over sodium sulfate, filtered and concentrated to provide 0.23 g of oil which solidified on standing. The solid was filtered from hexanes and diethyl ether to yield 154 mg of the title compound, a compound of the invention.
1H NMR δ 8.40 (s, 2H), 8.05 (s, 1H), 7.85 (s, 1H), 7.77 (d, 1H), 7.62-7.65 (m, 2H).
Synthesis Example 5
Preparation of 2-[2-(4-bromo-2H-1,2,3-triazol-2-yl)phenoxy]-5-chloropyrimidine (Compound 54)
Step A: Preparation of 1,2-ethanedione 1-[2-(2-methoxyphenyl)hydrazone]2-oxime
To a stirred solution of 40% glyoxal (8.06 mL, 70.2 mmol, 1.7 eq.) in water (275 mL) was added a solution of 2-methoxyphenylhydrazine hydrochloride (7.22 g, 41.3 mmol, 1.0 eq.) in 50% acetic acid (18 mL). The reaction was stirred at 23° C. for 2 h. A brown precipitate formed and was collected by filtration. The precipitate was dissolved in ethanol (82 mL) and 50% aq. hydroxylamine (5.06 mL, 82.6 mmol, 2.0 eq.) was added to the solution. The reaction mixture was stirred at 23° C. for 2 h, then concentrated in vaccuo to a volume of about 5 mL and then diluted with water. The mixture was extracted with ethyl acetate (3×50 mL) and the combined organic layers dried and concentrated in vaccuo to afford the crude title compound (4.40 g) which was used directly in the next step without further purification.
Step B: Preparation of 2-(2-methoxyphenyl)-2H-1,2,3-triazole 1-oxide
To a stirred solution of 1,2-ethanedione 1-[2-(2-methoxyphenyl)hydrazone]2-oxime (4.40 g, 22.8 mmol, 1.0 eq.) in pyridine (100 mL) was added a solution of CuSO4 5H2O (11.4 g, 45.5 mmol, 2.0 eq.) in water (55 mL). The reaction mixture was heated to reflux at 100° C. for 18 h. The reaction mixture was cooled to ambient temperature and acidified with concentrated hydrochloric acid until a green precipitate formed. The mixture was filtered through a plug of Celite® diatomaceaous filter aid. The aqueous layer was separated and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with aqueous 1 N hydrochloric acid and then with brine. The organic layer was dried and concentrated in vaccuo to afford the crude title compound (2.80 g) which required no further purification.
1H NMR δ 7.74 (d, 1H), 7.55 (t, 1H), 7.46 (s, 1H), 7.43 (d, 1H), 7.15-7.06 (m, 2H), 3.85 (s, 3H).
Step C: Preparation of 4-bromo-2-(2-methoxyphenyl)-2H-1,2,3-triazole 3-oxide
2-(2-Methoxyphenyl)-2H-1,2,3-triazole 1-oxide (i.e. the product from Example 5, Step B) (0.500 g, 2.61 mmol, 1.0 eq.) dissolved in a 1:1 mixture of chloroform (5 mL) and water (5 mL) was cooled to 0° C. Sodium carbonate (0.387 g, 3.65 mmol, 1.4 eq.) was added, followed by the addition of bromine (0.336 mL, 6.52 mmol, 2.5 eq.). The reaction mixture was stirred at 23° C. for 48 h, then quenched with saturated aqueous sodium thiosulfate and extracted with dichloromethane (3×10 mL). The organic layers were combined, dried and concentrated in vaccuo. The crude residue was purified by chromatography on silica gel, eluting with ethyl acetate in hexanes, to afford the title compound (0.250 g).
1H NMR δ 7.79 (s, 1H), 7.66-7.50 (m, 1H), 7.40 (dd, 1H), 7.14-7.05 (m, 2H), 3.84 (s, 3H).
Step D: Preparation of 4-bromo-2-(2-methoxyphenyl)-2H-1,2,3-triazole
A stirred mixture of 4-bromo-2-(2-methoxyphenyl)-2H-1,2,3-triazole 3-oxide (i.e. the product from Example 5, Step C) (0.250 g, 0.926 mmol, 1.0 eq.) and phosphorus trichloride (0.242 mL, 2.78 mmol, 3.0 eq.) was heated to reflux at 80° C. for 2 h, then cooled to 0° C. and diluted with dichloromethane (10 mL). Methanol (5 mL) was added dropwise, followed by the addition of water (15 mL). The aqueous layer was separated and extracted with dichloromethane (2×10 mL). The combined organic layers were dried and concentrated. The crude residue was purified by chromatography on silica gel, eluting with 0 to 30% ethyl acetate in hexanes, to afford the title compound (0.170 g) as a white solid.
1H NMR δ 7.79 (s, 1H), 7.49 (d, 1H), 7.44 (t, 1H), 7.10-6.95 (m, 2H), 3.87 (s, 3H).
Step E: Preparation of 2-(4-bromo-2H-1,2,3-triazol-2-yl)phenol
To a solution of 4-bromo-2-(2-methoxyphenyl)-2H-1,2,3-triazole (i.e. the product of Example 5, Step D) (0.150 g, 0.590 mmol, 1.0 eq.) in dichloromethane at 0° C. was added a 1.0 M solution of boron tribromide in dichloromethane (2.95 mL, 2.95 mmol, 5.0 equiv). The reaction mixture was warmed to ambient temperature and stirred for 2 h. The reaction as cooled to 0° C. and slowly quenched with a saturated aqueous solution of sodium bicarbonate (5 mL). The biphasic mixture was stirred at room temperature for 1 h. The phases were separated and the aqueous layer was extracted with dichloromethane (2×10 mL). The combined organic layers were dried and concentrated in vacuo. The crude residue was purified by chromatography on silica gel, eluting with 0 to 30% ethyl acetate in hexanes, to afford the title compound (0.135 g) as a white solid.
1H NMR δ 9.98 (s, 1H), 8.05 (dd, 1H), 7.81 (s, 1H), 7.30-7.23 (m, 1H), 7.14 (dd, 1H), 7.01-6.98 (m, 1H).
Step F: Preparation of 2-[2-(4-bromo-2H-1,2,3-triazol-2-yl)phenoxy]-5-chloropyrimidine
To a solution of 2-(4-bromo-2H-1,2,3-triazol-2-yl)phenol (i.e. the product from Example 5, Step E) (0.115 g, 0.479 mmol, 1.0 eq.) in acetonitrile was added 2,5-dichloropyrimidine (71.4 mg, 0.479 mmol, 1.0 eq.) and potassium carbonate (79.4 mg, 5.75 mmol, 1.2 eq.). The reaction mixture was heated at 80° C. overnight. After cooling to room temperature, the reaction mixture was filtered through a plug of Celite® diatomaceaous filter aid and rinsed with ethyl acetate. The filtrate was concentrated onto Celite® diatomaceaous filter aid and purified by chromatography on silica gel, eluting with 0 to 25% ethyl acetate in hexanes, to afford the title compound (135 mg).
1H NMR δ 8.43 (s, 2H), 7.93 (dd, 1H), 7.61 (s, 1H), 7.56-7.48 (m, 1H), 7.47-7.41 (m, 1H), 7.38 (dd, 1H).
Synthesis Example 6
Preparation of 5-chloro-2-[2-[4-(difluoromethyl)-1H-pyrazol-1-yl]phenoxy]pyrimidine (Compound 80)
Step A: Preparation of 1-phenyl-1H-pyrazole-4-carboxaldehyde
A solution of 1-phenylpyrazole (2.0 g, 13.87 mmoles) in TFA (17 mL) was stirred under a nitrogen atmosphere and treated with. hexamethylene tetramine (2.92 g, 20.81 mmoles). The reaction was refluxed overnight, and then cooled and poured into saturated sodium bicarbonate aqueous solution to adjust the pH to 7. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated to 2.78 g of crude oil. Flash column chromatography on silica gel with a 40 gram Isco MPLC column using 10-20% EtOAc-Hexanes gradient provided 0.72 g of the title compound.
1H NMR δ 9.98 (s, 1H), 8.44 (s, 1H), 8.17 (s, 1H), 7.70 (m, 2H), 7.5 (m, 2H), 7.4 (m, 1H).
Step B: Preparation of 1-phenyl-4-(difluoromethyl)-1H-pyrazole
1-Phenyl-1H-pyrazole-4-carboxaldehyde (i.e. the product from Example 6, Step A), (529 mg, 3.07 mmoles) was heated neat in DeoxyFluor® (1.0 mL, 5.22 mmoles) at 80° C. under a nitrogen atmosphere overnight. The reaction mixture was cooled and then diluted with saturated sodium bicarbonate aqueous solution. The aqueous phase was extracted three times with dichloromethane. The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated to 0.86 g of crude oil. Flash column chromatography on silica gel with a 12 gram Isco MPLC column using 10-20% EtOAc-Hexanes gradient provided 0.49 g of the title compound.
1H NMR δ 8.09 (s, 1H), 7.85 (s, 1H), 7.68 (d, 2H), 7.49 (t, 2H), 7.35 (t, 1H), 6.79 (t, 1H).
Step C: Preparation of 2-[4-(difluoromethyl)-1H-pyrazol-1-yl]phenol 1-acetate
1-Phenyl-4-(difluoromethyl)-1H-pyrazole (i.e. the product from Example 6, Step B), (0.49 g, 2.52 mmoles) was stirred in 19 mL of acetic acid. The mixture was treated with iodobenzene diacetate (0.89 g, 2.78 mmoles) and palladium acetate (28 mg, 0.126 mmoles) and heated to 100° C. for three hours. The mixture was cooled and concentrated from toluene to give 0.68 grams of crude oil. Flash column chromatography on silica gel with a 12 gram Isco MPLC column using 20% EtOAc-Hexanes provided 0.41 g of the title compound.
1H NMR δ 7.93 (s, 1H), 7.85 (s, 1H), 7.61 (d, 1H), 7.44 (t, 1H), 7.38 (t, 1H), 7.25 (d, 1H), 6.78 (t, 1H), 2.218 (s, 3H).
Step D: Preparation of 2-[4-(difluoromethyl)-1H-pyrazol-1-yl]phenol
2-[4-(Difluoromethyl)-1H-pyrazol-1-yl]phenol 1-acetate (i.e. the product from Example 6, Step C), (0.41 g, 1.626 mmoles) was dissolved in 13 mL of methanol under a nitrogen atmosphere. The mixture was treated with 3 mL of de-ionized water and then ammonium acetate (1.0 g, 13.0 mmoles). The mixture was stirred at room temperature overnight. The mixture was concentrated under vacuum and then partitioned between water and EtOAc. The phases were separated and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated to give 0.3 g solid. The crude product was treated with hexanes and filtered to yield 166 mg of the title compound.
1H NMR δ 8.18 (s, 1H), 7.87 (s, 1H), 7.36 (d, 1H), 7.23 (t, 1H), 7.13 (d, 1H), 6.96 (t, 1H), 6.82 (t, 1H).
Step E: Preparation of 5-chloro-2-[2-[4-(difluoromethyl)-1H-pyrazol-1-yl]phenoxy]-pyrimidine
The title compound was prepared in the same fashion as described in Example 1, Step C, using 2-[4-(difluoromethyl)-1H-pyrazol-1-yl]phenol (i.e. the product from Example 6, Step D), (161 mg, 0.766 mmoles) in place of 2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-phenol to give 170 mg of the title compound, a compound of the present invention, as a solid.
1H NMR δ 8.40 (s, 2H), 8.08 (s, 1H), 7.80 (d, 1H), 7.72 (s, 1H), 7.41-7.50 (m, 2H), 7.33 (d, 1H), 6.67 (t, 1H).
Synthesis Example 7
Preparation of 3-(5-chloropyrimidin-2-yl)oxy-2-[4-(difluoromethyl)-1H-pyrazol-1-yl]benzonitrile (Compound 253)
Step A: Preparation of 5-chloro-2-[2-[4-(difluoromethyl)-1H-pyrazol-1-yl]-3-iodophenoxy]pyrimidine
5-Chloro-2-[2-[4-(difluoromethyl)-1H-pyrazol-1-yl]phenoxy]-pyrimidine (i.e. the product from Example 6, Step E), (285 mg, 0.883 mmoles) was dissolved in 6.3 mL of acetic acid. The mixture was treated with palladium acetate (10 mg, 0.044 mmoles) and N-iodosuccinimide (220 mg, 0.971 mmoles) and then heated at 100° C. for four hours. The mixture was cooled and then concentrated under vacuum from toluene. The resultant mixture was partitioned in saturated NaHCO3 aqueous solution and EtOAc. The phases were separated and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with saturated aqueous NaHCO3, brine, dried over MgSO4, filtered and concentrated to a crude oil. Flash column chromatography on silica gel with a 12 gram Isco MPLC column using 10 to 20% EtOAc-Hexanes gradient provided 0.46 g of the title compound.
1H NMR δ 8.39 (s, 2H), 7.89 (d, 1H), 7.71 (s, 1H), 7.64 (s, 1H), 7.27-7.33 (m, 2H), 7.69 (t, 1H).
Step B: Preparation of 3-(5-chloropyrimidin-2-yl)oxy-2-[4-(difluoromethyl)-1H-pyrazol-1-yl]benzonitrile
5-Chloro-2-[2-[4-(difluoromethyl)-1H-pyrazol-1-yl]-3-iodophenoxy]pyrimidine (i.e. the product from Example 7, Step A), (0.23 g, 0.513 mmoles) was dissolved in 2.85 mL of N,N-dimethylacetamide. The mixture was treated with copper(I)cyanide (0.07 g, 0.770 mmoles) and heated at 130° C. overnight. The mixture was cooled and then diluted with EtOAc. The mixture was filtered thru a celite pad and rinsed with EtOAc. The filtrate was washed twice with saturated EDTA aqueous solution, once with brine, dried over MgSO4, filtered and concentrated to 0.29 g crude oil. Flash column chromatography on silica gel with a 12 gram Isco MPLC column using Hexanes to 40% EtOAc-Hexanes gradient provided 0.13 g. The solid was triturated with hexanes and some Et2O to give 56 mg of the title compound, a compound of the present invention, as a solid.
1H NMR δ 8.39 (s, 2H), 7.94 (s, 1H), 7.78 (s, 1H), 7.76 (d, 1H), 7.61 (m, 2H), 6.68 (t, 1H).
Synthesis Example 8
Preparation of 3-[(5-chloro-2-pyrimidinyl)oxy]-2-[4-(trifluoromethylthio)-1-pyrazolyl]benzonitrile (Compound 134)
Step A: Preparation of 1-phenyl-4-(trifluoromethylthio)-1H-pyrazol-5-amine
1-pheny-1H-pyrazol-5-amine (5.0 g, 31.41 mmoles) was dissolved in 25 mL of dichloromethane under a nitrogen atmosphere. The mixture was cooled to 0° C. and treated with 2 mL of pyridine. Trifluoromethylsulfenyl chloride (3 mL) was condensed into a gas addition funnel before adding over 40 minutes at a temperature ≦5° C. An additional 1 mL of trifluoromethylsulfenyl chloride was added. The reaction mixture was allowed to warm to ambient temperature, diluted with dichloromethane, and washed twice with saturated NaHCO3 aqueous solution., brine, dried over MgSO4 and concentrated to give 8 grams of solid. The crude solid was treated with hexanes and filtered to give 6.98 g of the title solid.
1H NMR δ 7.50-7.58 (m, 5H), 7.41 (t, 1H), 4.40 (bs, 2H).
Step B: Preparation of 1-phenyl-4-(trifluoromethylthio)-1H-pyrazole
1-Phenyl-4-(trifluoromethylthio)-1H-pyrazol-5-amine (i.e. the product from Example 8, Step A), (1.0 g, 3.86 mmoles) was dissolved in 19 mL of THF under a nitrogen atmosphere. The mixture was treated with isopentyl nitrite (1.036 mL, 7.71 mmoles) and then heated at 68° C. overnight. The reaction mixture was cooled and concentrated to 1.7 g of liquid. The mixture was taken up in hexanes and concentrated to 1.2 g of solid. The solid was taken up in hexanes and filtered off to give 218 mg of the title compound as a solid. The filtrate was concentrated for Flash column chromatography on silica gel with a 12 gram Isco MPLC column using Hexanes to give 0.8 g of the title compound as a solid.
1H NMR δ 8.16 (s, 1H), 7.85 (s, 1H), 7.70 (d, 2H), 7.49 (t, 2H), 7.36 (t, 1H).
Step C: Preparation of 2-[4-(trifluoromethylthio)-1H-pyrazol-1-yl]phenol 1-acetate
The title compound was prepared in the same fashion as described in Example 6, Step C, using 1-phenyl-4-(trifluoromethylthio)-1H-pyrazole (i.e. the product from Example 8, Step B) (0.21 g, 0.819 mmoles) in place of 1-phenyl-4-(difluoromethyl)-1H-pyrazole to give 0.43 g of the title compound.
1H NMR δ 8.00 (s, 1H), 7.85 (s, 1H), 7.63 (d, 1H), 7.46 (t, 1H), 7.39 (t, 1H), 7.27 (d, 1H), 2.20 (s, 3H).
Step D: Preparation of 2-[4-(trifluoromethylthio)-1H-pyrazol-1-yl]phenol
The title compound was prepared in the same fashion as described in Example 6, Step D, using 2-[4-(trifluoromethylthio)-1H-pyrazol-1-yl]phenol 1-acetate (i.e. the product from Example 8, Step C) (0.21 g, 0.819 mmoles) in place of 2-[4-(Difluoromethyl)-1H-pyrazol-1-yl]phenol 1-acetate to give 0.10 g of the title compound,
1H NMR δ 8.22 (s, 1H), 7.89 (s, 1H), 7.37 (d, 1H), 7.25 (t, 1H), 7.14 (d, 1H), 6.96 (t, 1H).
Step E: Preparation of 5-chloro-2-[2-[4-(trifluoromethylthio)-1H-pyrazol-1-yl]phenoxy]pyrimidine
The title compound was prepared in the same fashion as described in Example 1, Step C, using 2-[4-(trifluoromethylthio)-1H-pyrazol-1-yl]phenol (i.e. the product from Example 8, Step D) (0.4 g, 1.537 mmoles) in place of (2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-phenol), to give 114 mg of the title compound,
1H NMR δ 8.37 (s, 2H), 8.14 (s, 1H), 7.80 (d, 1H), 7.71 (s, 1H), 7.41-7.50 (2×t, 1H each), 7.35 (d, 1H).
Step F: Preparation of 5-chloro-2-[3-iodo-2-[4-(trifluoromethylthio)-1H-pyrazol-1-yl]phenoxy]pyrimidine
The title compound was prepared in the same fashion as described in Example 7, Step A, using 5-chloro-2-[2-[4-(trifluoromethylthio)-1H-pyrazol-1-yl]phenoxy]-pyrimidine (i.e. the product from Example 8, Step E) (0.29 g, 0.778 mmoles) in place of 5-Chloro-2-[2-[4-(difluoromethyl)-1H-pyrazol-1-yl]phenoxy]-pyrimidine, to give 270 mg of the title compound.
1H NMR δ 8.38 (s, 2H), 7.91 (d, 1H), 7.72 (d, 2H),) 7.28-7.37 (m, 2H).
Step G: Preparation of 3-[(5-chloro-2-pyrimidinyl)oxy]-2-[4-(trifluoromethylthio)-1H-pyrazol-1-yl]benzonitrile
The title compound was prepared in the same fashion as described in Example 7, Step B, using 5-chloro-2-[3-iodo-2-[4-(trifluoromethylthio)-1H-pyrazol-1-yl]phenoxy]-pyrimidine (i.e. the product from Example 8, Step F) (0.26 g, 0.521 mmoles) in place of 5-Chloro-2-[2-[4-(difluoromethyl)-1H-pyrazol-1-yl]-3-iodophenoxy]pyrimidine, to give 103 mg of the title compound, a compound of the present invention.
1H NMR δ 8.36 (s, 2H), 8.01 (s, 1H), 7.78 (s&d, 2H), 7.63 (2×t, 2H).
Synthesis Example 9
Preparation of 3-[(5-chloro-2-pyrimidinyl)oxy]-2-[4-(trifluoromethylthio)-1H-pyrazol-1-yl]-benzonitrile (Compound 143)
5-Chloro-2-[2-[4-(trifluoromethylthio)-1H-pyrazol-1-yl]phenoxy]pyrimidine (i.e. the product from Example 8, Step E) (80 mg, 0.214 mmoles) was dissolved in acetone under a nitrogen atmosphere. The mixture was treated with water and Oxone® (0.20 g, 0.322 mmoles) and then stirred at room temperature overnight. The mixture was concentrated under vacuum and diluted with water and dichloromethane. The phases were separated and the aqueous phase was extracted twice with dichloromethane. The combined organic phases were washed 1× brine, dried over MgSO4, and concentrated to 0.13 g crude oil. Flash column chromatography on silica gel with a 12 gram Isco MPLC column using Hexanes to 40% EtOAc-Hexanes gradient to give 50 mg of the title compound as a solid.
1H NMR δ 8.43 (s, 1H), 8.40 (s, 2H), 8.01 (s, 1H), 7.82 (d, 1H), 7.53 (t, 1H), 7.46 (t, 1H), 7.37 (d, 1H).
Synthesis Example 10
Preparation of 5-chloro-2-[2-(4-cyclopropyl-1H-1,2,3-triazol-1-yl)phenoxy]pyrimidine (Compound 160)
Step A: Preparation of 2-azidophenol
To a solution of tert-butyl nitrite (4.91 ml, 41.2 mmol, 1.5 equiv) and 2-aminophenol (3.00 g, 27.5 mmol, 1.0 equiv) in acetonitrile (92 mL) at 0° C. was added azidotrimethylsilane (4.38 mL, 33.0 mmol, 1.2 equiv), dropwise. The reaction was removed from the ice bath and stirred at ambient temperature for 2 h. The reaction mixture was concentrated under vacuum onto Celite® and purified by column chromatography, eluting with 0 to 10% ethyl acetate in hexanes to afford the title product (3.55 g).
1H NMR δ 7.11-7.03 (m, 2H), 6.97-6.90 (m, 2H), 5.35 (s, 1H).
Step B: Preparation of 5-chloro-2-(2-azidophenoxy)pyrimidine
To a solution of 2-azidophenol (i.e. the product from Example 10, Step A) (3.55 g, 26.2 mmol, 1.0 equiv) and 2,5-dichloropyrimidine (3.91 g, 26.2 mmol, 1.0 equiv) in acetonitrile (87 mL) was added powdered potassium carbonate (4.35 g, 31.4 mmol, 1.2 equiv). The reaction mixture was heated to 70° C. for 4 h. The mixture was cooled to ambient temperature and filtered through a small pad of Celite®. The filtrate was concentrated under vacuum and purified by column chromatography on silica gel, eluting with 0 to 30% ethyl acetate in hexanes to afford the title product (4.44 g).
1H NMR δ 8.48 (s, 2H), 7.37-7.29 (m, 1H), 7.25-7.17 (m, 3H).
Step C: Preparation of 5-chloro-2-[2-(4-cyclopropyl-1H-1,2,3-triazol-1-yl)phenoxy]pyrimidine
To a solution of 5-chloro-2-(2-azidophenoxy)pyrimidine (i.e. the product from Example 10, Step B) (0.437 g, 1.76 mmol, 1.0 equiv) and cyclopropylacetylene (0.179 mL, 2.12 mmol, 1.2 equiv) in tert-butanol (3 mL) and water (3 mL) was added CuSO4.5H2O (43.9 mg, 0.176 mmol, 0.1 equiv) and sodium L-ascorbate (34.9 mg, 0.176 mmol, 0.1 equiv). The reaction was stirred at ambient temperature for 18 h. The reaction mixture was filtered through a small pad of Celite®. The filtrate was concentrated under vacuum and purified by column chromatography on silica gel, eluting with 0 to 30% ethyl acetate in hexanes to afford the title compound, a compound of the present invention, as a solid (0.461 g).
1H NMR δ 8.39 (s, 2H), 7.83 (dd, J=8.0, 1.7 Hz, 1H), 7.71 (s, 1H), 7.53-7.49 (m, 1H), 7.47-7.41 (m, 1H), 7.35 (dd, J=8.2, 1.4 Hz, 1H) 1.95-1.87 (m, 1H), 0.95-0.90 (m, 2H), 0.85-0.78 (m, 2H).
Synthesis Example 11
Preparation of 2-[3-[(5-chloro-2-pyrimidinyl)oxy]-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl]-1,3,4-oxadiazole (Compound 298)
Step A: Preparation of 3-hydroxy-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]benzoic acid
A solution of 3-hydroxy-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]benzonitrile (i.e. the product from Example 4, Step A) (1.25 g, 4.94 mmol) in mixture of acetic acid (6 mL) and concentrated sulfuric acid (6 mL) was heated at 105° C. for 35 minutes. The reaction mixture was poured into 200 g of ice and water. The slurry was saturated with sodium chloride. After stirring at room temperature for 3 hr, the solid was collected by filtration, washed with water and dried under a stream of nitrogen under vacuum to give 0.9 g of the title compound as a tan solid.
1H NMR (DMSO-d6) δ 8.5 (s, 1H), 8.02 (s, 1H), 7.41 (t, 1H), 7.26 (d, 1H), 7.22 (d, 1H).
Step B: Preparation of 3-hydroxy-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]benzoic acid methyl ester
To a solution of 3-hydroxy-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]benzoic acid (i.e. the product from Example 11, Step A) (670 mg, 2.45 mmol) in mixture of methanol (3 mL) and dichloromethane (3 mL) was slowly added a solution of trimethylsilyldiazomethane (2.4 mL of 2M solution in hexane). After stirring for a few minutes at room temperature, the solvent was evaporated off under a stream of nitrogen and the reaction mixture was purified by medium pressure liquid chromatography on 40 g of silica gel eluted with a gradient of 0-60% ethyl acetate in hexane to give 530 mg of the title compound as a solid.
1H NMR δ 8.20 (bs, 1H), 8.00 (s, 1H), 7.88 (s, 1H), 7.45 (d, 1H), 7.37 (t, 1H), 7.25 (d, 1H).
Step C: Preparation of 3-hydroxy-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]benzo-hydrazide
A solution of 3-hydroxy-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]benzoic acid methyl ester (i.e. the product from Example 11, Step B) (376 mg, 1.31 mmol) and hydrazine hydrate (1.5 ml) in ethanol (4 ml) was heated at 78° C. for 2.5 days. The reaction was diluted with 80 mL of ethyl acetate and washed with 40 mL of water. The ethyl acetate phase was filtered through a Varian Chem Elut celite tube and concentrated to a crude solid. This was triturated with dichloromethane, filtered, and collected to yield 240 mg of the title compound as a solid.
1H NMR (DMSO-d6) δ 10.4 (bs, 1H), 9.35 (s, 1H), 8.42 (s, 1H), 7.96 (s, 1H), 7.35 (t, 1H), 7.12 (d, 1H), 6.92 (d, 1H), 4.21 (bs, 2H).
Step D: Preparation of 2-[3-[(5-chloro-2-pyrimidinyl)oxy]-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl]-1,3,4-oxadiazole
A solution of 3-hydroxy-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]benzo-hydrazide (i.e. the product from Example 11, Step C) (189 mg, 0.66 mmol), toluenesulfonic acid hydrate (22 mg) in triethylorthoformate (6 mL) was heated at 120° C. for 27 hr. The solvent was evaporated off under a stream of nitrogen and the crude reaction was purified by MPLC on 12 g of silica gel eluted with a gradient of 0-80% ethyl acetate in hexane to give 104 mg of the intermediate phenol, which treated with dichloropyrimidine (166 mg) and cesium carbonate (617 mg) in acetonitrile (5 ml) at 48 C for 18 hr. After evaporation, the crude reaction mixture was combined with an earlier batch (55 mg phenol intermediate, 80 mg dichloropyrimidine, 260 mg cesium carbonate) and purified by medium pressure liquid chromatography on 24 g silica gel eluted with 0-80% ethyl acetate in hexane to give 120 mg of the title compound, a compound of the present invention, as a solid.
1H NMR δ 8.41 (s, 2H), 8.32 (s, 1H), 8.12 (s, 1H), 7.90 (s, 1H), 7.72 (m, 3H), 7.55 (d, 1H).
By the procedures described herein together with methods known in the art, the following compounds of Tables 1 to 1584 can be prepared. The following abbreviations are used in the Tables which follow: i means iso, c means cyclo, Me means methyl, Et means ethyl, Pr means propyl, Bu means butyl, i-Pr means isopropyl, c-Pr cyclopropyl, c-Bu means cyclobutyl, Ph means phenyl, OCH3 means methoxy, OEt means ethoxy, —CN means cyano, —NO2 means nitro, S(O)Me means methylsulfinyl, and S(O)2CH3 means methylsulfonyl.







TABLE 1







1








 


R2 = Cl; Z = O; and R3 = H (m = 0)








Y1, Y2, Y3 and Y4
Y1, Y2, Y3 and Y4





Y1 = CH, Y2 = CCF3, Y3 = CH and Y4 = CH
Y1 = N, Y2 = CBr, Y3 = CBr and Y4 = CH


Y1 = CCH3, Y2 = CH, Y3 = CCH3  and Y4 = CH
Y1 = N, Y2 = CH, Y3 = CCHO and Y4 = CH


Y1 = CH, Y2 = CBr, Y3 = CBr and Y4 = CH
Y1 = N, Y2 = CH, Y3 = CCH2CF3  and Y4 = CH


Y1 = CH, Y2 = CCHF2, Y3 = CH and Y4 = CH
Y1 = N, Y2 = CH, Y3 = C(i-Pr) and Y4 = CH


Y1 = CH, Y2 = CCF3, Y3 = CCF3  and Y4 = CH
Y1 = N, Y2 = CH, Y3 = C(CHC═CH) and Y4 = CH


Y1 = CH, Y2 = CCl, Y3 = CCl and Y4 = CH
Y1 = N, Y2 = CH, Y3 = CSCHF2 and Y4 = CH


Y1 = CH, Y2 = CCH3, Y3 = CH and Y4 = CH
Y1 = N, Y2 = CH, Y3 = CSO2CF3 and Y4 = CH


Y1 = CH, Y2 = CCH3, Y3 = CCH3  and Y4 = CH
Y1 = N, Y2 = CH, Y3 = CCH2SCH3  and Y4 = CH


Y1 = CCF3, Y2 = CH, Y3 = CCF3  and Y4 = CH
Y1 = N, Y2 = CF, Y3 = CH and Y4 = CH


Y1 = N, Y2 = CH, Y3 = CH and Y4 = CH
Y1 = N, Y2 = CH, Y3 = CCH3  and Y4 = CH


Y1 = N, Y2 = CCF3, Y3 = CH and Y4 = CH
Y1 = N, Y2 = CH, Y3 = CH and Y4 = CCF3


Y1 = N, Y2 = CBr, Y3 = CH and Y4 = CH
Y1 = N, Y2 = CH, Y3 = CH and Y4 = CBr


Y1 = N, Y2 = CH, Y3 = CF and Y4 = CH
Y1 = N, Y2 = CCl, Y3 = CH and Y4 = CH


Y1 = N, Y2 = CH, Y3 = CH and Y4 = CCH3
Y1 = N, Y2 = CH, Y3 = CCH2CH3  and Y4 = CH


Y1 = N, Y2 = CHF2, Y3 = CH and Y4 = CH
Y1 = N, Y2 = CH, Y3 = CH and Y4 = CCHF2


Y1 = N, Y2 = CCl, Y3 = CH and Y4 = CH
Y1 = N, Y2 = COCF3, Y3 = CH and Y4 = CH


Y1 = N, Y2 = CH, Y3 = CCl and Y4 = CH
Y1 = N, Y2 = CH, Y3 = CCN and Y4 = CH


Y1 = N, Y2 = CH, Y3 = CH and Y4 = CCH2CH3
Y1 = N, Y2 = CH, Y3 = CH and Y4 = COCF3


Y1 = N, Y2 = COCH3, Y3 = CH and Y4 = CH
Y1 = N, Y2 = CH, Y3 = CH and Y4 = COCHF2


Y1 = N, Y2 = COCHF2, Y3 = CH and Y4 = CH
Y1 = N, Y2 = CCH3, Y3 = CH and Y4 = CCH3


Y1 = N, Y2 = CH, Y3 = COCF3  and Y4 = CH
Y1 = N, Y2 = CH, Y3 = CPh and Y4 = CH


Y1 = N, Y2 = CH, Y3 = CH and Y4 = CCN
Y1 = N, Y2 = CH, Y3 = CH and Y4 = CC(═O)OCH3


Y1 = N, Y2 = CC(═O)OCH3, Y3 = CH and Y4 = CH
Y1 = N, Y2 = CBr, Y3 = CH and Y4 = CBr


Y1 = N, Y2 = CF, Y3 = CH and Y4 = CF
Y1 = N, Y2 = CCF3, Y3 = CCF3  and Y4 = CH


Y1 = N, Y2 = CCF3, Y3 = CH and Y4 = CCF3
Y1 = N, Y2 = CH, Y3 = COCF2CF2H and Y4 = CH


Y1 = N, Y2 = CH, Y3 = CH and Y4 = CPh
Y1 = N, Y2 = CH, Y3 = C(n-Pr) and Y4 = CH


Y1 = N, Y2 = CCF3, Y3 = CH and Y4 = CCH3
Y1 = N, Y2 = CH, Y3 = CCCH and Y4 = CH


Y1 = N, Y2 = CH, Y3 = CCHF2 and Y4 = CH
Y1 = CH, Y2 = N, Y3 = CCH3  and Y4 = CH


Y1 = N, Y2 = CH, Y3 = CSCF3  and Y4 = CH
Y1 = CH, Y2 = N, Y3 = CCHO and Y4 = CH


Y1 = N, Y2 = CH, Y3 = CSO2CH3  and Y4 = CH
Y1 = CH, Y2 = N, Y3 = COCH3  and Y4 = CH


Y1 = N, Y2 = CH, Y3 = COCH2CHCH2  and Y4 = CH
Y1 = N, Y2 = CH, Y3 = N and Y4 = CH


Y1 = N, Y2 = CH, Y3 = CCHF2 and Y4 = CH
Y1 = N, Y2 = CF3, Y3 = N and Y4 = CH


Y1 = N, Y2 = CH, Y3 = CI and Y4 = CH
Y1 = N, Y2 = CCl, Y3 = N and Y4 = CH


Y1 = N, Y2 = CH, Y3 = CH and Y4 = CCl
Y1 = N, Y2 = CBr, Y3 = N and Y4 = CBr


Y1 = N, Y2 = CCN, Y3 = CH and Y4 = CH
Y1 = N, Y2 = CCH3, Y3 = N and Y4 = CH


Y1 = N, Y2 = CH, Y3 = COCH3  and Y4 = CH
Y1 = N, Y2 = CF, Y3 = N and Y4 = CH


Y1 = N, Y2 = CH, Y3 = COCHF2 and Y4 = CH
Y1 = N, Y2 = CCl, Y3 = N and Y4 = CCl


Y1 = N, Y2 = CH, Y3 = CH and Y4 = COCF3
Y1 = N, Y2 = CHF2, Y3 = N and Y4 = CH


Y1 = N, Y2 = CPh, Y3 = CH and Y4 = CH
Y1 = N, Y2 = CBr, Y3 = N and Y4 = CH


Y1 = N, Y2 = CH, Y3 = CC(═O)OCH3  and Y4 = CH
Y1 = N, Y2 = CPh, Y3 = N and Y4 = CH


Y1 = N, Y2 = CCl, Y3 = CH and Y4 = CCl
Y1 = N, Y2 = N, Y3 = CH and Y4 = CH


Y1 = N, Y2 = CCHF2, Y3 = CH and Y4 = CCHF2
Y1 = N, Y2 = N, Y3 = CCF3  and Y4 = CH


Y1 = N, Y2 = CCH3, Y3 = CCH3  and Y4 = CH
Y1 = N, Y2 = N, Y3 = CI and Y4 = CH


Y1 = N, Y2 = CCl, Y3 = CCl and Y4 = CH
Y1 = N, Y2 = N, Y3 = CCH3F and Y4 = CH


Y1 = N, Y2 = CCH3, Y3 = CH and Y4 = CH
Y1 = N, Y2 = N, Y3 = CCl and Y4 = CH


Y1 = N, Y2 = CH, Y3 = CCF3  and Y4 = CH
Y1 = N, Y2 = N, Y3 = CCHF2 and Y4 = CH


Y1 = N, Y2 = CH, Y3 = CBr and Y4 = CH
Y1 = N, Y2 = N, Y3 = CBr and Y4 = CH


Y1 = N, Y2 = CH, Y3 = CH and Y4 = CF
Y1 = N, Y2 = N, Y3 = CCH3  and Y4 = CH


Y1 = N, Y2 = CCH2CH3, Y3 = CH and Y4 = CH
Y1 = N, Y2 = N, Y3 = CF and Y4 = CH


Y1 = N, Y2 = CH, Y3 = CCF2CF3  and Y4 = CH
Y1 = N, Y2 = N, Y3 = CPh and Y4 = CH


Y1 = N, Y2 = CH, Y3 = COCH2CF3  and Y4 = CH
Y1 = N, Y2 = N, Y3 = COCF3  and Y4 = CH


Y1 = N, Y2 = CH, Y3 = C(c-Pr) and Y4 = CH
Y1 = N, Y2 = N, Y3 = COCHF2 and Y4 = CH


Y1 = N, Y2 = CH, Y3 = CCHCH2  and Y 4 = CH
Y1 = N, Y2 = N, Y3 = COCH2F and Y4 = CH


Y1 = N, Y2 = CH, Y3 = COCH2CCH and Y4 = CH
Y1 = N, Y2 = N, Y3 = CCH2CF3  and Y4 = CH


Y1 = N, Y2 = CH, Y3 = CSOCH3  and Y4 = CH
Y1 = N, Y2 = N, Y3 = C(i-Pr) and Y4 = CH


Y1 = N, Y2 = CH, Y3 = CCH2OCH3  and Y4 = CH
Y1 = N, Y2 = N, Y3 = CCH2C≡CH and Y4 = CH


Y1 = CH, Y2 = N, Y3 = CF and Y4 = CH
Y1 = N, Y2 = N, Y3 = CSCHF2 and Y4 = CH


Y1 = CH, Y2 = N, Y3 = CI and Y4 = CH
Y1 = N, Y2 = N, Y3 = CSO2CF3  and Y4 = CH


Y1 = CH, Y2 = N, Y3 = CCHF2 and Y4 = CH
Y1 = N, Y2 = N, Y3 = CCH2SCH3  and Y4 = CH


Y1 = CH, Y2 = N, Y3 = CCF3  and Y4 = CH
Y1 = N, Y2 = N, Y3 = CCH2CH3  and Y4 = CH


Y1 = CH, Y2 = N, Y3 = CBr and Y4 = CH
Y1 = N, Y2 = N, Y3 = CCN and Y4 = CH


Y1 = CH, Y2 = N, Y3 = CCH2CH3  and Y4 = CH
Y1 = N, Y2 = N, Y3 = COCH2CN and Y4 = CH


Y1 = CH, Y2 = N, Y3 = CCH2CF3  and Y4 = CH
Y1 = N, Y2 = N, Y3 = CCH2CN and Y4 = CH


Y1 = CH, Y2 = N, Y3 = CCl and Y4 = CH
Y1 = N, Y2 = N, Y3 = C(n-Pr) and Y4 = CH


Y1 = N, Y2 = N, Y3 = CC≡CH and Y4 = CH
Y1 = N, Y2 = N, Y3 = C(3-CF3—Ph) and Y4 = CH


Y1 = N, Y2 = N, Y3 = CCH═CH2 and Y4 = CH
Y1 = N, Y2 = N, Y3 = C(3,5-di-F—Ph) and Y4 = CH


Y1 = N, Y2 = N, Y3 = CC≡CCH3  and Y4 = CH
Y1 = N, Y2 = N, Y3 = C(3,5-di-Cl—Ph) and Y4 = CH


Y1 = N, Y2 = N, Y3 = CSCF3  and Y4 = CH
Y1 = N, Y2 = N, Y3 = C(3,5-di-Br—Ph) and Y4 = CH


Y1 = N, Y2 = N, Y3 = CSO2CH3 and Y4 = CH
Y1 = N, Y2 = N, Y3 = C(C═O)CH3 and Y4 = CH


Y1 = N, Y2 = N, Y3 = COCH2CHCH2  and Y4 = CH
Y1 = N, Y2 = N, Y3 = C(C═CH2)CH3 and Y4 = CH


Y1 = N, Y2 = N, Y3 = COCH2CH2CF3 and Y4 = CH
Y1 = N, Y2 = N, Y3 = C(C═NOH)CH3 and Y4 = CH


Y1 = N, Y2 = N, Y3 = COCH3 and Y4 = CH
Y1 = N, Y2 = N, Y3 = CSi(CH3)3 and Y4 = CH


Y1 = N, Y2 = N, Y3 = CCF2CF3 and Y4 = CH
Y1 = N, Y2 = CH, Y3 = CH and Y4 = N


Y1 = N, Y2 = N, Y3 = COCH2CF3 and Y4 = CH
Y1 = N, Y2 = CCH3, Y3 = CH, and and Y4 = N


Y1 = N, Y2 = N, Y3 = COCH2C≡CH and Y4 = CH
Y1 = N, Y2 = CF, Y3 = CH, and and Y4 = N


Y1 = N, Y2 = N, Y3 = CSOCH3 and Y4 = CH
Y1 = N, Y2 = CPh, Y3 = C, and and Y4 = N


Y1 = N, Y2 = N, Y3 = CCH2OCH3 and Y4 = CH
Y1 = N, Y2 = CCl, Y3 = CCl, and and Y4 = N


Y1 = N, Y2 = N, Y3 = C(Cyclohexyl) and Y4 = CH
Y1 = N, Y2 = CCHF2, Y3 = CH and Y4 = N


Y1 = N, Y2 = N, Y3 = C(Cyclopentyl) and Y4 = CH
Y1 = N, Y2 = CBr, Y3 = CH and Y4 = N


Y1 = N, Y2 = N, Y3 = C(Cyclopropyl) and Y4 = CH
Y1 = N, Y2 = CCF3, Y3 = CCF3 and Y4 = N


Y1 = N, Y2 = N, Y3 = C(3-thiophenyl) and Y4 = CH
Y1 = N, Y2 = CCF3, Y3 = CH, and and Y4 = N


Y1 = N, Y2 = N, Y3 = C(2-thiophenyl) and Y4 = CH
Y1 = N, Y2 = CCl, Y3 = CH, and and Y4 = N


Y1 = N, Y2 = N, Y3 = C(3-pyridyl) and Y4 = CH
Y1 = N, Y2 = CCH3, Y3 = CCH3, and and Y4 = N


Y1 = N, Y2 = N, Y3 = C(2-pyridyl) and Y4 = CH
Y1 = N, Y2 = CBr, Y3 = CBr, and and Y4 = N


Y1 = N, Y2 = N, Y3 = C(4-pyridyl) and Y4 = CH









The present disclosure also includes Tables 2 through 1584. Each Table is constructed in the the same manner as Table 1 above, except that the row heading in Table 1 (i.e. “R2═Cl; Z═O; and R3═H (m=0).”) is replaced with the respective row heading shown below.











Table
Header Row
















2
R2 = F, Z = O, R3 = H (m = 0)


3
R2 = F, Z = O, R3 = 3-F


4
R2 = F, Z = O, R3 = 3-Cl


5
R2 = F, Z = O, R3 = 3-Br


6
R2 = F, Z = O, R3 = 3-I


7
R2 = F, Z = O, R3 = 3-CN


8
R2 = F, Z = O, R3 = 3-NO2


9
R2 = F, Z = O, R3 = 3-OMe


10
R2 = F, Z = O, R3 = 3-OCF3


11
R2 = F, Z = O, R3 = 3-CF3


12
R2 = F, Z = O, R3 = 3-CHF2


13
R2 = F, Z = O, R3 = 3-CH2F


14
R2 = F, Z = O, R3 = 3-CHO


15
R2 = F, Z = O, R3 = 3-Me


16
R2 = F, Z = O, R3 = 3-Et


17
R2 = F, Z = O, R3 = 3-Ethynyl


18
R2 = F, Z = O, R3 = 3-Ethenyl


19
R2 = F, Z = O, R3 = 3-SO2Me


20
R2 = F, Z = O, R3 = 3-OAc


21
R2 = F, Z = O, R3 = 3-c-Pr


22
R2 = F, Z = O, R3 = 3-i-Pr


23
R2 = F, Z = O, R3 = 3-Ph


24
R2 = F, Z = S, R3 = 3-F


25
R2 = F, Z = S, R3 = 3-Cl


26
R2 = F, Z = S, R3 = 3-Br


27
R2 = F, Z = S, R3 = 3-I


28
R2 = F, Z = S, R3 = 3-CN


29
R2 = F, Z = S, R3 = 3-NO2


30
R2 = F, Z = S, R3 = 3-OMe


31
R2 = F, Z = S, R3 = 3-OCF3


32
R2 = F, Z = S, R3 = 3-CF3


33
R2 = F, Z = S, R3 = 3-CHF2


34
R2 = F, Z = S, R3 = 3-CH2F


35
R2 = F, Z = S, R3 = 3-CHO


36
R2 = F, Z = S, R3 = 3-Me


37
R2 = F, Z = S, R3 = 3-Et


38
R2 = F, Z = S, R3 = 3-Ethynyl


39
R2 = F, Z = S, R3 = 3-Ethenyl


40
R2 = F, Z = S, R3 = 3-SO2Me


41
R2 = F, Z = S, R3 = 3-OAc


42
R2 = F, Z = S, R3 = 3-c-Pr


43
R2 = F, Z = S, R3 = 3-i-Pr


44
R2 = F, Z = S, R3 = 3-Ph


45
R2 = F, Z = O, R3 = 4-F


46
R2 = F, Z = O, R3 = 4-Cl


47
R2 = F, Z = O, R3 = 4-Br


48
R2 = F, Z = O, R3 = 4-I


49
R2 = F, Z = O, R3 = 4-CN


50
R2 = F, Z = O, R3 = 4-NO2


51
R2 = F, Z = O, R3 = 4-OMe


52
R2 = F, Z = O, R3 = 4-OCF3


53
R2 = F, Z = O, R3 = 4-CF3


54
R2 = F, Z = O, R3 = 4-CHF2


55
R2 = F, Z = O, R3 = 4-CH2F


56
R2 = F, Z = O, R3 = 4-CHO


57
R2 = F, Z = O, R3 = 4-Me


58
R2 = F, Z = O, R3 = 4-Et


59
R2 = F, Z = O, R3 = 4-Ethynyl


60
R2 = F, Z = O, R3 = 4-Ethenyl


61
R2 = F, Z = O, R3 = 4-SO2Me


62
R2 = F, Z = O, R3 = 4-OAc


63
R2 = F, Z = O, R3 = 4-c-Pr


64
R2 = F, Z = O, R3 = 4-i-Pr


65
R2 = F, Z = O, R3 = 4-Ph


66
R2 = F, Z = O, R3 = 5-F


67
R2 = F, Z = O, R3 = 5-Cl


68
R2 = F, Z = O, R3 = 5-Br


69
R2 = F, Z = O, R3 = 5-I


70
R2 = F, Z = O, R3 = 5-CN


71
R2 = F, Z = O, R3 = 5-NO2


72
R2 = F, Z = O, R3 = 5-OMe


73
R2 = F, Z = O, R3 = 5-OCF3


74
R2 = F, Z = O, R3 = 5-CF3


75
R2 = F, Z = O, R3 = 5-CHF2


76
R2 = F, Z = O, R3 = 5-CH2F


77
R2 = F, Z = O, R3 = 5-CHO


78
R2 = F, Z = O, R3 = 5-Me


79
R2 = F, Z = O, R3 = 5-Et


80
R2 = F, Z = O, R3 = 5-Ethynyl


81
R2 = F, Z = O, R3 = 5-Ethenyl


82
R2 = F, Z = O, R3 = 5-SO2Me


83
R2 = F, Z = O, R3 = 5-OAc


84
R2 = F, Z = O, R3 = 5-c-Pr


85
R2 = F, Z = O, R3 = 5-i-Pr


86
R2 = F, Z = O, R3 = 5-Ph


87
R2 = F, Z = O, R3 = 6-F


88
R2 = F, Z = O, R3 = 6-Cl


89
R2 = F, Z = O, R3 = 6-Br


90
R2 = F, Z = O, R3 = 6-I


91
R2 = F, Z = O, R3 = 6-CN


92
R2 = F, Z = O, R3 = 6-NO2


93
R2 = F, Z = O, R3 = 6-OMe


94
R2 = F, Z = O, R3 = 6-OCF3


95
R2 = F, Z = O, R3 = 6-CF3


96
R2 = F, Z = O, R3 = 6-CHF2


97
R2 = F, Z = O, R3 = 6-CH2F


98
R2 = F, Z = O, R3 = 6-CHO


99
R2 = F, Z = O, R3 = 6-Me


100
R2 = F, Z = O, R3 = 6-Et


101
R2 = F, Z = O, R3 = 6-Ethynyl


102
R2 = F, Z = O, R3 = 6-Ethenyl


103
R2 = F, Z = O, R3 = 6-SO2Me


104
R2 = F, Z = O, R3 = 6-OAc


105
R2 = F, Z = O, R3 = 6-c-Pr


106
R2 = F, Z = O, R3 = 6-i-Pr


107
R2 = F, Z = O, R3 = 6-Ph


108
R2 = F, Z = O, R3 = 3,4-di-F


109
R2 = F, Z = O, R3 = 3,5-di-F


110
R2 = F, Z = O, R3 = 3,6-di-F


111
R2 = F, Z = O, R3 = 4,5-di-F


112
R2 = F, Z = O, R3 = 3,4-di-Cl


113
R2 = F, Z = O, R3 = 3,5-di-Cl


114
R2 = F, Z = O, R3 = 3,6-di-Cl


115
R2 = F, Z = O, R3 = 4,5-di-Cl


116
R2 = F, Z = O, R3 = 3,4-di-Br


117
R2 = F, Z = O, R3 = 3,5-di-Br


118
R2 = F, Z = O, R3 = 3,6-di-Br


119
R2 = F, Z = O, R3 = 4,5-di-Br


120
R2 = F, Z = O, R3 = 3,4-di-CN


121
R2 = F, Z = O, R3 = 3,5-di-CN


122
R2 = F, Z = O, R3 = 3,6-di-CN


123
R2 = F, Z = O, R3 = 4,5-di-CN


124
R2 = F, Z = O, R3 = 3,4-di-Me


125
R2 = F, Z = O, R3 = 3,5-di-Me


126
R2 = F, Z = O, R3 = 3,6-di-Me


127
R2 = F, Z = O, R3 = 4,5-di-Me


128
R2 = F, Z = O, R3 = 3,4-di-OMe


129
R2 = F, Z = O, R3 = 3,5-di-OMe


130
R2 = F, Z = O, R3 = 3,6-di-OMe


131
R2 = F, Z = O, R3 = 4,5-di-OMe


132
R2 = F, Z = O, R3 = 3,4-di-CF3


133
R2 = F, Z = O, R3 = 3,5-di-CF3


134
R2 = F, Z = O, R3 = 3,6-di-CF3


135
R2 = F, Z = O, R3 = 4,5-di-CF3


136
R2 = F, Z = O, R3 = 3-CN, 4-Me


137
R2 = F, Z = O, R3 = 3-CN, 4-F


138
R2 = F, Z = O, R3 = 3-CN, 4-Br


139
R2 = F, Z = O, R3 = 3-CN, 4-OMe


140
R2 = F, Z = O, R3 = 3-CN, 4-CF3


141
R2 = F, Z = O, R3 = 3-CN, 6-Me


142
R2 = F, Z = O, R3 = 3-CN, 6-F


143
R2 = F, Z = O, R3 = 3-CN, 6-Br


144
R2 = F, Z = O, R3 = 3-CN, 6-OMe


145
R2 = F, Z = O, R3 = 3-CN, 6-CF3


146
R2 = Br, Z = O, R3 = H (m = 0)


147
R2 = Br, Z = O, R3 = 3-F


148
R2 = Br, Z = O, R3 = 3-Cl


149
R2 = Br, Z = O, R3 = 3-Br


150
R2 = Br, Z = O, R3 = 3-I


151
R2 = Br, Z = O, R3 = 3-CN


152
R2 = Br, Z = O, R3 = 3-NO2


153
R2 = Br, Z = O, R3 = 3-OMe


154
R2 = Br, Z = O, R3 = 3-OCF3


155
R2 = Br, Z = O, R3 = 3-CF3


156
R2 = Br, Z = O, R3 = 3-CHF2


157
R2 = Br, Z = O, R3 = 3-CH2F


158
R2 = Br, Z = O, R3 = 3-CHO


159
R2 = Br, Z = O, R3 = 3-Me


160
R2 = Br, Z = O, R3 = 3-Et


161
R2 = Br, Z = O, R3 = 3-Ethynyl


162
R2 = Br, Z = O, R3 = 3-Ethenyl


163
R2 = Br, Z = O, R3 = 3-SO2Me


164
R2 = Br, Z = O, R3 = 3-OAc


165
R2 = Br, Z = O, R3 = 3-c-Pr


166
R2 = Br, Z = O, R3 = 3-i-Pr


167
R2 = Br, Z = O, R3 = 3-Ph


168
R2 = Br, Z = S, R3 = 3-F


169
R2 = Br, Z = S, R3 = 3-Cl


170
R2 = Br, Z = S, R3 = 3-Br


171
R2 = Br, Z = S, R3 = 3-I


172
R2 = Br, Z = S, R3 = 3-CN


173
R2 = Br, Z = S, R3 = 3-NO2


174
R2 = Br, Z = S, R3 = 3-OMe


175
R2 = Br, Z = S, R3 = 3-OCF3


176
R2 = Br, Z = S, R3 = 3-CF3


177
R2 = Br, Z = S, R3 = 3-CHF2


178
R2 = Br, Z = S, R3 = 3-CH2F


179
R2 = Br, Z = S, R3 = 3-CHO


180
R2 = Br, Z = S, R3 = 3-Me


181
R2 = Br, Z = S, R3 = 3-Et


182
R2 = Br, Z = S, R3 = 3-Ethynyl


183
R2 = Br, Z = S, R3 = 3-Ethenyl


184
R2 = Br, Z = S, R3 = 3-SO2Me


185
R2 = Br, Z = S, R3 = 3-OAc


186
R2 = Br, Z = S, R3 = 3-c-Pr


187
R2 = Br, Z = S, R3 = 3-i-Pr


188
R2 = Br, Z = S, R3 = 3-Ph


189
R2 = Br, Z = O, R3 = 4-F


190
R2 = Br, Z = O, R3 = 4-Cl


191
R2 = Br, Z = O, R3 = 4-Br


192
R2 = Br, Z = O, R3 = 4-I


193
R2 = Br, Z = O, R3 = 4-CN


194
R2 = Br, Z = O, R3 = 4-NO2


195
R2 = Br, Z = O, R3 = 4-OMe


196
R2 = Br, Z = O, R3 = 4-OCF3


197
R2 = Br, Z = O, R3 = 4-CF3


198
R2 = Br, Z = O, R3 = 4-CHF2


199
R2 = Br, Z = O, R3 = 4-CH2F


200
R2 = Br, Z = O, R3 = 4-CHO


201
R2 = Br, Z = O, R3 = 4-Me


202
R2 = Br, Z = O, R3 = 4-Et


203
R2 = Br, Z = O, R3 = 4-Ethynyl


204
R2 = Br, Z = O, R3 = 4-Ethenyl


205
R2 = Br, Z = O, R3 = 4-SO2Me


206
R2 = Br, Z = O, R3 = 4-OAc


207
R2 = Br, Z = O, R3 = 4-c-Pr


208
R2 = Br, Z = O, R3 = 4-i-Pr


209
R2 = Br, Z = O, R3 = 4-Ph


210
R2 = Br, Z = O, R3 = 5-F


211
R2 = Br, Z = O, R3 = 5-Cl


212
R2 = Br, Z = O, R3 = 5-Br


213
R2 = Br, Z = O, R3 = 5-I


214
R2 = Br, Z = O, R3 = 5-CN


215
R2 = Br, Z = O, R3 = 5-NO2


216
R2 = Br, Z = O, R3 = 5-OMe


217
R2 = Br, Z = O, R3 = 5-OCF3


218
R2 = Br, Z = O, R3 = 5-CF3


219
R2 = Br, Z = O, R3 = 5-CHF2


220
R2 = Br, Z = O, R3 = 5-CH2F


221
R2 = Br, Z = O, R3 = 5-CHO


222
R2 = Br, Z = O, R3 = 5-Me


223
R2 = Br, Z = O, R3 = 5-Et


224
R2 = Br, Z = O, R3 = 5-Ethynyl


225
R2 = Br, Z = O, R3 = 5-Ethenyl


226
R2 = Br, Z = O, R3 = 5-SO2Me


227
R2 = Br, Z = O, R3 = 5-OAc


228
R2 = Br, Z = O, R3 = 5-c-Pr


229
R2 = Br, Z = O, R3 = 5-i-Pr


230
R2 = Br, Z = O, R3 = 5-Ph


231
R2 = Br, Z = O, R3 = 6-F


232
R2 = Br, Z = O, R3 = 6-Cl


233
R2 = Br, Z = O, R3 = 6-Br


234
R2 = Br, Z = O, R3 = 6-I


235
R2 = Br, Z = O, R3 = 6-CN


236
R2 = Br, Z = O, R3 = 6-NO2


237
R2 = Br, Z = O, R3 = 6-OMe


238
R2 = Br, Z = O, R3 = 6-OCF3


239
R2 = Br, Z = O, R3 = 6-CF3


240
R2 = Br, Z = O, R3 = 6-CHF2


241
R2 = Br, Z = O, R3 = 6-CH2F


242
R2 = Br, Z = O, R3 = 6-CHO


243
R2 = Br, Z = O, R3 = 6-Me


244
R2 = Br, Z = O, R3 = 6-Et


245
R2 = Br, Z = O, R3 = 6-Ethynyl


246
R2 = Br, Z = O, R3 = 6-Ethenyl


247
R2 = Br, Z = O, R3 = 6-SO2Me


248
R2 = Br, Z = O, R3 = 6-OAc


249
R2 = Br, Z = O, R3 = 6-c-Pr


250
R2 = Br, Z = O, R3 = 6-i-Pr


251
R2 = Br, Z = O, R3 = 6-Ph


252
R2 = Br, Z = O, R3 = 3,4-di-F


253
R2 = Br, Z = O, R3 = 3,5-di-F


254
R2 = Br, Z = O, R3 = 3,6-di-F


255
R2 = Br, Z = O, R3 = 4,5-di-F


256
R2 = Br, Z = O, R3 = 3,4-di-Cl


257
R2 = Br, Z = O, R3 = 3,5-di-Cl


258
R2 = Br, Z = O, R3 = 3,6-di-Cl


259
R2 = Br, Z = O, R3 = 4,5-di-Cl


260
R2 = Br, Z = O, R3 = 3,4-di-Br


261
R2 = Br, Z = O, R3 = 3,5-di-Br


262
R2 = Br, Z = O, R3 = 3,6-di-Br


263
R2 = Br, Z = O, R3 = 4,5-di-Br


264
R2 = Br, Z = O, R3 = 3,4-di-CN


265
R2 = Br, Z = O, R3 = 3,5-di-CN


266
R2 = Br, Z = O, R3 = 3,6-di-CN


267
R2 = Br, Z = O, R3 = 4,5-di-CN


268
R2 = Br, Z = O, R3 = 3,4-di-Me


269
R2 = Br, Z = O, R3 = 3,5-di-Me


270
R2 = Br, Z = O, R3 = 3,6-di-Me


271
R2 = Br, Z = O, R3 = 4,5-di-Me


272
R2 = Br, Z = O, R3 = 3,4-di-OMe


273
R2 = Br, Z = O, R3 = 3,5-di-OMe


274
R2 = Br, Z = O, R3 = 3,6-di-OMe


275
R2 = Br, Z = O, R3 = 4,5-di-OMe


276
R2 = Br, Z = O, R3 = 3,4-di-CF3


277
R2 = Br, Z = O, R3 = 3,5-di-CF3


278
R2 = Br, Z = O, R3 = 3,6-di-CF3


279
R2 = Br, Z = O, R3 = 4,5-di-CF3


280
R2 = Br, Z = O, R3 = 3-CN, 4-Me


281
R2 = Br, Z = O, R3 = 3-CN, 4-F


282
R2 = Br, Z = O, R3 = 3-CN, 4-Br


283
R2 = Br, Z = O, R3 = 3-CN, 4-OMe


284
R2 = Br, Z = O, R3 = 3-CN, 4-CF3


285
R2 = Br, Z = O, R3 = 3-CN, 6-Me


286
R2 = Br, Z = O, R3 = 3-CN, 6-F


287
R2 = Br, Z = O, R3 = 3-CN, 6-Br


288
R2 = Br, Z = O, R3 = 3-CN, 6-OMe


289
R2 = Br, Z = O, R3 = 3-CN, 6-CF3


290
R2 = Cl, Z = O, R3 = H (m = 0)


291
R2 = Cl, Z = O, R3 = 3-F


292
R2 = Cl, Z = O, R3 = 3-Cl


293
R2 = Cl, Z = O, R3 = 3-Br


294
R2 = Cl, Z = O, R3 = 3-I


295
R2 = Cl, Z = O, R3 = 3-CN


296
R2 = Cl, Z = O, R3 = 3-NO2


297
R2 = Cl, Z = O, R3 = 3-OMe


298
R2 = Cl, Z = O, R3 = 3-OCF3


299
R2 = Cl, Z = O, R3 = 3-CF3


300
R2 = Cl, Z = O, R3 = 3-CHF2


301
R2 = Cl, Z = O, R3 = 3-CH2F


302
R2 = Cl, Z = O, R3 = 3-CHO


303
R2 = Cl, Z = O, R3 = 3-Me


304
R2 = Cl, Z = O, R3 = 3-Et


305
R2 = Cl, Z = O, R3 = 3-Ethynyl


306
R2 = Cl, Z = O, R3 = 3-Ethenyl


307
R2 = Cl, Z = O, R3 = 3-SO2Me


308
R2 = Cl, Z = O, R3 = 3-OAc


309
R2 = Cl, Z = O, R3 = 3-c-Pr


310
R2 = Cl, Z = O, R3 = 3-i-Pr


311
R2 = Cl, Z = O, R3 = 3-Ph


312
R2 = Cl, Z = S, R3 = 3-F


313
R2 = Cl, Z = S, R3 = 3-Cl


314
R2 = Cl, Z = S, R3 = 3-Br


315
R2 = Cl, Z = S, R3 = 3-I


316
R2 = Cl, Z = S, R3 = 3-CN


317
R2 = Cl, Z = S, R3 = 3-NO2


318
R2 = Cl, Z = S, R3 = 3-OMe


319
R2 = Cl, Z = S, R3 = 3-OCF3


320
R2 = Cl, Z = S, R3 = 3-CF3


321
R2 = Cl, Z = S, R3 = 3-CHF2


322
R2 = Cl, Z = S, R3 = 3-CH2F


323
R2 = Cl, Z = S, R3 = 3-CHO


324
R2 = Cl, Z = S, R3 = 3-Me


325
R2 = Cl, Z = S, R3 = 3-Et


326
R2 = Cl, Z = S, R3 = 3-Ethynyl


327
R2 = Cl, Z = S, R3 = 3-Ethenyl


328
R2 = Cl, Z = S, R3 = 3-SO2Me


329
R2 = Cl, Z = S, R3 = 3-OAc


330
R2 = Cl, Z = S, R3 = 3-c-Pr


331
R2 = Cl, Z = S, R3 = 3-i-Pr


332
R2 = Cl, Z = S, R3 = 3-Ph


333
R2 = Cl, Z = O, R3 = 4-F


334
R2 = Cl, Z = O, R3 = 4-Cl


335
R2 = Cl, Z = O, R3 = 4-Br


336
R2 = Cl, Z = O, R3 = 4-I


337
R2 = Cl, Z = O, R3 = 4-CN


338
R2 = Cl, Z = O, R3 = 4-NO2


339
R2 = Cl, Z = O, R3 = 4-OMe


340
R2 = Cl, Z = O, R3 = 4-OCF3


341
R2 = Cl, Z = O, R3 = 4-CF3


342
R2 = Cl, Z = O, R3 = 4-CHF2


343
R2 = Cl, Z = O, R3 = 4-CH2F


344
R2 = Cl, Z = O, R3 = 4-CHO


345
R2 = Cl, Z = O, R3 = 4-Me


346
R2 = Cl, Z = O, R3 = 4-Et


347
R2 = Cl, Z = O, R3 = 4-Ethynyl


348
R2 = Cl, Z = O, R3 = 4-Ethenyl


349
R2 = Cl, Z = O, R3 = 4-SO2Me


350
R2 = Cl, Z = O, R3 = 4-OAc


351
R2 = Cl, Z = O, R3 = 4-c-Pr


352
R2 = Cl, Z = O, R3 = 4-i-Pr


353
R2 = Cl, Z = O, R3 = 4-Ph


354
R2 = Cl, Z = O, R3 = 5-F


355
R2 = Cl, Z = O, R3 = 5-Cl


356
R2 = Cl, Z = O, R3 = 5-Br


357
R2 = Cl, Z = O, R3 = 5-I


358
R2 = Cl, Z = O, R3 = 5-CN


359
R2 = Cl, Z = O, R3 = 5-NO2


360
R2 = Cl, Z = O, R3 = 5-OMe


361
R2 = Cl, Z = O, R3 = 5-OCF3


362
R2 = Cl, Z = O, R3 = 5-CF3


363
R2 = Cl, Z = O, R3 = 5-CHF2


364
R2 = Cl, Z = O, R3 = 5-CH2F


365
R2 = Cl, Z = O, R3 = 5-CHO


366
R2 = Cl, Z = O, R3 = 5-Me


367
R2 = Cl, Z = O, R3 = 5-Et


368
R2 = Cl, Z = O, R3 = 5-Ethynyl


369
R2 = Cl, Z = O, R3 = 5-Ethenyl


370
R2 = Cl, Z = O, R3 = 5-SO2Me


371
R2 = Cl, Z = O, R3 = 5-OAc


372
R2 = Cl, Z = O, R3 = 5-c-Pr


373
R2 = Cl, Z = O, R3 = 5-i-Pr


374
R2 = Cl, Z = O, R3 = 5-Ph


375
R2 = Cl, Z = O, R3 = 6-F


376
R2 = Cl, Z = O, R3 = 6-Cl


377
R2 = Cl, Z = O, R3 = 6-Br


378
R2 = Cl, Z = O, R3 = 6-I


379
R2 = Cl, Z = O, R3 = 6-CN


380
R2 = Cl, Z = O, R3 = 6-NO2


381
R2 = Cl, Z = O, R3 = 6-OMe


382
R2 = Cl, Z = O, R3 = 6-OCF3


383
R2 = Cl, Z = O, R3 = 6-CF3


384
R2 = Cl, Z = O, R3 = 6-CHF2


385
R2 = Cl, Z = O, R3 = 6-CH2F


386
R2 = Cl, Z = O, R3 = 6-CHO


387
R2 = Cl, Z = O, R3 = 6-Me


388
R2 = Cl, Z = O, R3 = 6-Et


389
R2 = Cl, Z = O, R3 = 6-Ethynyl


390
R2 = Cl, Z = O, R3 = 6-Ethenyl


391
R2 = Cl, Z = O, R3 = 6-SO2Me


392
R2 = Cl, Z = O, R3 = 6-OAc


393
R2 = Cl, Z = O, R3 = 6-c-Pr


394
R2 = Cl, Z = O, R3 = 6-i-Pr


395
R2 = Cl, Z = O, R3 = 6-Ph


396
R2 = Cl, Z = O, R3 = 3,4-di-F


397
R2 = Cl, Z = O, R3 = 3,5-di-F


398
R2 = Cl, Z = O, R3 = 3,6-di-F


399
R2 = Cl, Z = O, R3 = 4,5-di-F


400
R2 = Cl, Z = O, R3 = 3,4-di-Cl


401
R2 = Cl, Z = O, R3 = 3,5-di-Cl


402
R2 = Cl, Z = O, R3 = 3,6-di-Cl


403
R2 = Cl, Z = O, R3 = 4,5-di-Cl


404
R2 = Cl, Z = O, R3 = 3,4-di-Br


405
R2 = Cl, Z = O, R3 = 3,5-di-Br


406
R2 = Cl, Z = O, R3 = 3,6-di-Br


407
R2 = Cl, Z = O, R3 = 4,5-di-Br


408
R2 = Cl, Z = O, R3 = 3,4-di-CN


409
R2 = Cl, Z = O, R3 = 3,5-di-CN


410
R2 = Cl, Z = O, R3 = 3,6-di-CN


411
R2 = Cl, Z = O, R3 = 4,5-di-CN


412
R2 = Cl, Z = O, R3 = 3,4-di-Me


413
R2 = Cl, Z = O, R3 = 3,5-di-Me


414
R2 = Cl, Z = O, R3 = 3,6-di-Me


415
R2 = Cl, Z = O, R3 = 4,5-di-Me


416
R2 = Cl, Z = O, R3 = 3,4-di-OMe


417
R2 = Cl, Z = O, R3 = 3,5-di-OMe


418
R2 = Cl, Z = O, R3 = 3,6-di-OMe


419
R2 = Cl, Z = O, R3 = 4,5-di-OMe


420
R2 = Cl, Z = O, R3 = 3,4-di-CF3


421
R2 = Cl, Z = O, R3 = 3,5-di-CF3


422
R2 = Cl, Z = O, R3 = 3,6-di-CF3


423
R2 = Cl, Z = O, R3 = 4,5-di-CF3


424
R2 = Cl, Z = O, R3 = 3-CN, 4-Me


425
R2 = Cl, Z = O, R3 = 3-CN, 4-F


426
R2 = Cl, Z = O, R3 = 3-CN, 4-Br


427
R2 = Cl, Z = O, R3 = 3-CN, 4-OMe


428
R2 = Cl, Z = O, R3 = 3-CN, 4-CF3


429
R2 = Cl, Z = O, R3 = 3-CN, 6-Me


430
R2 = Cl, Z = O, R3 = 3-CN, 6-F


431
R2 = Cl, Z = O, R3 = 3-CN, 6-Br


432
R2 = Cl, Z = O, R3 = 3-CN, 6-OMe


433
R2 = Cl, Z = O, R3 = 3-CN, 6-CF3


434
R2 = I, Z = O, R3 = H (m = 0)


435
R2 = I, Z = O, R3 = 3-F


436
R2 = I, Z = O, R3 = 3-Cl


437
R2 = I, Z = O, R3 = 3-Br


438
R2 = I, Z = O, R3 = 3-I


439
R2 = I, Z = O, R3 = 3-CN


440
R2 = I, Z = O, R3 = 3-NO2


441
R2 = I, Z = O, R3 = 3-OMe


442
R2 = I, Z = O, R3 = 3-OCF3


443
R2 = I, Z = O, R3 = 3-CF3


444
R2 = I, Z = O, R3 = 3-CHF2


445
R2 = I, Z = O, R3 = 3-CH2F


446
R2 = I, Z = O, R3 = 3-CHO


447
R2 = I, Z = O, R3 = 3-Me


448
R2 = I, Z = O, R3 = 3-Et


449
R2 = I, Z = O, R3 = 3-Ethynyl


450
R2 = I, Z = O, R3 = 3-Ethenyl


451
R2 = I, Z = O, R3 = 3-SO2Me


452
R2 = I, Z = O, R3 = 3-OAc


453
R2 = I, Z = O, R3 = 3-c-Pr


454
R2 = I, Z = O, R3 = 3-i-Pr


455
R2 = I, Z = O, R3 = 3-Ph


456
R2 = I, Z = S, R3 = 3-F


457
R2 = I, Z = S, R3 = 3-Cl


458
R2 = I, Z = S, R3 = 3-Br


459
R2 = I, Z = S, R3 = 3-I


460
R2 = I, Z = S, R3 = 3-CN


461
R2 = I, Z = S, R3 = 3-NO2


462
R2 = I, Z = S, R3 = 3-OMe


463
R2 = I, Z = S, R3 = 3-OCF3


464
R2 = I, Z = S, R3 = 3-CF3


465
R2 = I, Z = S, R3 = 3-CHF2


466
R2 = I, Z = S, R3 = 3-CH2F


467
R2 = I, Z = S, R3 = 3-CHO


468
R2 = I, Z = S, R3 = 3-Me


469
R2 = I, Z = S, R3 = 3-Et


470
R2 = I, Z = S, R3 = 3-Ethynyl


471
R2 = I, Z = S, R3 = 3-Ethenyl


472
R2 = I, Z = S, R3 = 3-SO2Me


473
R2 = I, Z = S, R3 = 3-OAc


474
R2 = I, Z = S, R3 = 3-c-Pr


475
R2 = I, Z = S, R3 = 3-i-Pr


476
R2 = I, Z = S, R3 = 3-Ph


477
R2 = I, Z = O, R3 = 4-F


478
R2 = I, Z = O, R3 = 4-Cl


479
R2 = I, Z = O, R3 = 4-Br


480
R2 = I, Z = O, R3 = 4-I


481
R2 = I, Z = O, R3 = 4-CN


482
R2 = I, Z = O, R3 = 4-NO2


483
R2 = I, Z = O, R3 = 4-OMe


484
R2 = I, Z = O, R3 = 4-OCF3


485
R2 = I, Z = O, R3 = 4-CF3


486
R2 = I, Z = O, R3 = 4-CHF2


487
R2 = I, Z = O, R3 = 4-CH2F


488
R2 = I, Z = O, R3 = 4-CHO


489
R2 = I, Z = O, R3 = 4-Me


490
R2 = I, Z = O, R3 = 4-Et


491
R2 = I, Z = O, R3 = 4-Ethynyl


492
R2 = I, Z = O, R3 = 4-Ethenyl


493
R2 = I, Z = O, R3 = 4-SO2Me


494
R2 = I, Z = O, R3 = 4-OAc


495
R2 = I, Z = O, R3 = 4-c-Pr


496
R2 = I, Z = O, R3 = 4-i-Pr


497
R2 = I, Z = O, R3 = 4-Ph


498
R2 = I, Z = O, R3 = 5-F


499
R2 = I, Z = O, R3 = 5-Cl


500
R2 = I, Z = O, R3 = 5-Br


501
R2 = I, Z = O, R3 = 5-I


502
R2 = I, Z = O, R3 = 5-CN


503
R2 = I, Z = O, R3 = 5-NO2


504
R2 = I, Z = O, R3 = 5-OMe


505
R2 = I, Z = O, R3 = 5-OCF3


506
R2 = I, Z = O, R3 = 5-CF3


507
R2 = I, Z = O, R3 = 5-CHF2


508
R2 = I, Z = O, R3 = 5-CH2F


509
R2 = I, Z = O, R3 = 5-CHO


510
R2 = I, Z = O, R3 = 5-Me


511
R2 = I, Z = O, R3 = 5-Et


512
R2 = I, Z = O, R3 = 5-Ethynyl


513
R2 = I, Z = O, R3 = 5-Ethenyl


514
R2 = I, Z = O, R3 = 5-SO2Me


515
R2 = I, Z = O, R3 = 5-OAc


516
R2 = I, Z = O, R3 = 5-c-Pr


517
R2 = I, Z = O, R3 = 5-i-Pr


518
R2 = I, Z = O, R3 = 5-Ph


519
R2 = I, Z = O, R3 = 6-F


520
R2 = I, Z = O, R3 = 6-Cl


521
R2 = I, Z = O, R3 = 6-Br


522
R2 = I, Z = O, R3 = 6-I


523
R2 = I, Z = O, R3 = 6-CN


524
R2 = I, Z = O, R3 = 6-NO2


525
R2 = I, Z = O, R3 = 6-OMe


526
R2 = I, Z = O, R3 = 6-OCF3


527
R2 = I, Z = O, R3 = 6-CF3


528
R2 = I, Z = O, R3 = 6-CHF2


529
R2 = I, Z = O, R3 = 6-CH2F


530
R2 = I, Z = O, R3 = 6-CHO


531
R2 = I, Z = O, R3 = 6-Me


532
R2 = I, Z = O, R3 = 6-Et


533
R2 = I, Z = O, R3 = 6-Ethynyl


534
R2 = I, Z = O, R3 = 6-Ethenyl


535
R2 = I, Z = O, R3 = 6-SO2Me


536
R2 = I, Z = O, R3 = 6-OAc


537
R2 = I, Z = O, R3 = 6-c-Pr


538
R2 = I, Z = O, R3 = 6-i-Pr


539
R2 = I, Z = O, R3 = 6-Ph


540
R2 = I, Z = O, R3 = 3,4-di-F


541
R2 = I, Z = O, R3 = 3,5-di-F


542
R2 = I, Z = O, R3 = 3,6-di-F


543
R2 = I, Z = O, R3 = 4,5-di-F


544
R2 = I, Z = O, R3 = 3,4-di-Cl


545
R2 = I, Z = O, R3 = 3,5-di-Cl


546
R2 = I, Z = O, R3 = 3,6-di-Cl


547
R2 = I, Z = O, R3 = 4,5-di-Cl


548
R2 = I, Z = O, R3 = 3,4-di-Br


549
R2 = I, Z = O, R3 = 3,5-di-Br


550
R2 = I, Z = O, R3 = 3,6-di-Br


551
R2 = I, Z = O, R3 = 4,5-di-Br


552
R2 = I, Z = O, R3 = 3,4-di-CN


553
R2 = I, Z = O, R3 = 3,5-di-CN


554
R2 = I, Z = O, R3 = 3,6-di-CN


555
R2 = I, Z = O, R3 = 4,5-di-CN


556
R2 = I, Z = O, R3 = 3,4-di-Me


557
R2 = I, Z = O, R3 = 3,5-di-Me


558
R2 = I, Z = O, R3 = 3,6-di-Me


559
R2 = I, Z = O, R3 = 4,5-di-Me


560
R2 = I, Z = O, R3 = 3,4-di-OMe


561
R2 = I, Z = O, R3 = 3,5-di-OMe


562
R2 = I, Z = O, R3 = 3,6-di-OMe


563
R2 = I, Z = O, R3 = 4,5-di-OMe


564
R2 = I, Z = O, R3 = 3,4-di-CF3


565
R2 = I, Z = O, R3 = 3,5-di-CF3


566
R2 = I, Z = O, R3 = 3,6-di-CF3


567
R2 = I, Z = O, R3 = 4,5-di-CF3


568
R2 = I, Z = O, R3 = 3-CN, 4-Me


569
R2 = I, Z = O, R3 = 3-CN, 4-F


570
R2 = I, Z = O, R3 = 3-CN, 4-Br


571
R2 = I, Z = O, R3 = 3-CN, 4-OMe


572
R2 = I, Z = O, R3 = 3-CN, 4-CF3


573
R2 = I, Z = O, R3 = 3-CN, 6-Me


574
R2 = I, Z = O, R3 = 3-CN, 6-F


575
R2 = I, Z = O, R3 = 3-CN, 6-Br


576
R2 = I, Z = O, R3 = 3-CN, 6-OMe


577
R2 = I, Z = O, R3 = 3-CN, 6-CF3


578
R2 = Me, Z = O, R3 = H (m = 0)


579
R2 = Me, Z = O, R3 = 3-F


580
R2 = Me, Z = O, R3 = 3-Cl


581
R2 = Me, Z = O, R3 = 3-Br


582
R2 = Me, Z = O, R3 = 3-I


583
R2 = Me, Z = O, R3 = 3-CN


584
R2 = Me, Z = O, R3 = 3-NO2


585
R2 = Me, Z = O, R3 = 3-OMe


586
R2 = Me, Z = O, R3 = 3-OCF3


587
R2 = Me, Z = O, R3 = 3-CF3


588
R2 = Me, Z = O, R3 = 3-CHF2


589
R2 = Me, Z = O, R3 = 3-CH2F


590
R2 = Me, Z = O, R3 = 3-CHO


591
R2 = Me, Z = O, R3 = 3-Me


592
R2 = Me, Z = O, R3 = 3-Et


593
R2 = Me, Z = O, R3 = 3-Ethynyl


594
R2 = Me, Z = O, R3 = 3-Ethenyl


595
R2 = Me, Z = O, R3 = 3-SO2Me


596
R2 = Me, Z = O, R3 = 3-OAc


597
R2 = Me, Z = O, R3 = 3-c-Pr


598
R2 = Me, Z = O, R3 = 3-i-Pr


599
R2 = Me, Z = O, R3 = 3-Ph


600
R2 = Me, Z = S, R3 = 3-F


601
R2 = Me, Z = S, R3 = 3-Cl


602
R2 = Me, Z = S, R3 = 3-Br


603
R2 = Me, Z = S, R3 = 3-I


604
R2 = Me, Z = S, R3 = 3-CN


605
R2 = Me, Z = S, R3 = 3-NO2


606
R2 = Me, Z = S, R3 = 3-OMe


607
R2 = Me, Z = S, R3 = 3-OCF3


608
R2 = Me, Z = S, R3 = 3-CF3


609
R2 = Me, Z = S, R3 = 3-CHF2


610
R2 = Me, Z = S, R3 = 3-CH2F


611
R2 = Me, Z = S, R3 = 3-CHO


612
R2 = Me, Z = S, R3 = 3-Me


613
R2 = Me, Z = S, R3 = 3-Et


614
R2 = Me, Z = S, R3 = 3-Ethynyl


615
R2 = Me, Z = S, R3 = 3-Ethenyl


616
R2 = Me, Z = S, R3 = 3-SO2Me


617
R2 = Me, Z = S, R3 = 3-OAc


618
R2 = Me, Z = S, R3 = 3-c-Pr


619
R2 = Me, Z = S, R3 = 3-i-Pr


620
R2 = Me, Z = S, R3 = 3-Ph


621
R2 = Me, Z = O, R3 = 4-F


622
R2 = Me, Z = O, R3 = 4-Cl


623
R2 = Me, Z = O, R3 = 4-Br


624
R2 = Me, Z = O, R3 = 4-I


625
R2 = Me, Z = O, R3 = 4-CN


626
R2 = Me, Z = O, R3 = 4-NO2


627
R2 = Me, Z = O, R3 = 4-OMe


628
R2 = Me, Z = O, R3 = 4-OCF3


629
R2 = Me, Z = O, R3 = 4-CF3


630
R2 = Me, Z = O, R3 = 4-CHF2


631
R2 = Me, Z = O, R3 = 4-CH2F


632
R2 = Me, Z = O, R3 = 4-CHO


633
R2 = Me, Z = O, R3 = 4-Me


634
R2 = Me, Z = O, R3 = 4-Et


635
R2 = Me, Z = O, R3 = 4-Ethynyl


636
R2 = Me, Z = O, R3 = 4-Ethenyl


637
R2 = Me, Z = O, R3 = 4-SO2Me


638
R2 = Me, Z = O, R3 = 4-OAc


639
R2 = Me, Z = O, R3 = 4-c-Pr


640
R2 = Me, Z = O, R3 = 4-i-Pr


641
R2 = Me, Z = O, R3 = 4-Ph


642
R2 = Me, Z = O, R3 = 5-F


643
R2 = Me, Z = O, R3 = 5-Cl


644
R2 = Me, Z = O, R3 = 5-Br


645
R2 = Me, Z = O, R3 = 5-I


646
R2 = Me, Z = O, R3 = 5-CN


647
R2 = Me, Z = O, R3 = 5-NO2


648
R2 = Me, Z = O, R3 = 5-OMe


649
R2 = Me, Z = O, R3 = 5-OCF3


650
R2 = Me, Z = O, R3 = 5-CF3


651
R2 = Me, Z = O, R3 = 5-CHF2


652
R2 = Me, Z = O, R3 = 5-CH2F


653
R2 = Me, Z = O, R3 = 5-CHO


654
R2 = Me, Z = O, R3 = 5-Me


655
R2 = Me, Z = O, R3 = 5-Et


656
R2 = Me, Z = O, R3 = 5-Ethynyl


657
R2 = Me, Z = O, R3 = 5-Ethenyl


658
R2 = Me, Z = O, R3 = 5-SO2Me


659
R2 = Me, Z = O, R3 = 5-OAc


660
R2 = Me, Z = O, R3 = 5-c-Pr


661
R2 = Me, Z = O, R3 = 5-i-Pr


662
R2 = Me, Z = O, R3 = 5-Ph


663
R2 = Me, Z = O, R3 = 6-F


664
R2 = Me, Z = O, R3 = 6-Cl


665
R2 = Me, Z = O, R3 = 6-Br


666
R2 = Me, Z = O, R3 = 6-I


667
R2 = Me, Z = O, R3 = 6-CN


668
R2 = Me, Z = O, R3 = 6-NO2


669
R2 = Me, Z = O, R3 = 6-OMe


670
R2 = Me, Z = O, R3 = 6-OCF3


671
R2 = Me, Z = O, R3 = 6-CF3


672
R2 = Me, Z = O, R3 = 6-CHF2


673
R2 = Me, Z = O, R3 = 6-CH2F


674
R2 = Me, Z = O, R3 = 6-CHO


675
R2 = Me, Z = O, R3 = 6-Me


676
R2 = Me, Z = O, R3 = 6-Et


677
R2 = Me, Z = O, R3 = 6-Ethynyl


678
R2 = Me, Z = O, R3 = 6-Ethenyl


679
R2 = Me, Z = O, R3 = 6-SO2Me


680
R2 = Me, Z = O, R3 = 6-OAc


681
R2 = Me, Z = O, R3 = 6-c-Pr


682
R2 = Me, Z = O, R3 = 6-i-Pr


683
R2 = Me, Z = O, R3 = 6-Ph


684
R2 = Me, Z = O, R3 = 3,4-di-F


685
R2 = Me, Z = O, R3 = 3,5-di-F


686
R2 = Me, Z = O, R3 = 3,6-di-F


687
R2 = Me, Z = O, R3 = 4,5-di-F


688
R2 = Me, Z = O, R3 = 3,4-di-Cl


689
R2 = Me, Z = O, R3 = 3,5-di-Cl


690
R2 = Me, Z = O, R3 = 3,6-di-Cl


691
R2 = Me, Z = O, R3 = 4,5-di-Cl


692
R2 = Me, Z = O, R3 = 3,4-di-Br


693
R2 = Me, Z = O, R3 = 3,5-di-Br


694
R2 = Me, Z = O, R3 = 3,6-di-Br


695
R2 = Me, Z = O, R3 = 4,5-di-Br


696
R2 = Me, Z = O, R3 = 3,4-di-CN


697
R2 = Me, Z = O, R3 = 3,5-di-CN


698
R2 = Me, Z = O, R3 = 3,6-di-CN


699
R2 = Me, Z = O, R3 = 4,5-di-CN


700
R2 = Me, Z = O, R3 = 3,4-di-Me


701
R2 = Me, Z = O, R3 = 3,5-di-Me


702
R2 = Me, Z = O, R3 = 3,6-di-Me


703
R2 = Me, Z = O, R3 = 4,5-di-Me


704
R2 = Me, Z = O, R3 = 3,4-di-OMe


705
R2 = Me, Z = O, R3 = 3,5-di-OMe


706
R2 = Me, Z = O, R3 = 3,6-di-OMe


707
R2 = Me, Z = O, R3 = 4,5-di-OMe


708
R2 = Me, Z = O, R3 = 3,4-di-CF3


709
R2 = Me, Z = O, R3 = 3,5-di-CF3


710
R2 = Me, Z = O, R3 = 3,6-di-CF3


711
R2 = Me, Z = O, R3 = 4,5-di-CF3


712
R2 = Me, Z = O, R3 = 3-CN, 4-Me


713
R2 = Me, Z = O, R3 = 3-CN, 4-F


714
R2 = Me, Z = O, R3 = 3-CN, 4-Br


715
R2 = Me, Z = O, R3 = 3-CN, 4-OMe


716
R2 = Me, Z = O, R3 = 3-CN, 4-CF3


717
R2 = Me, Z = O, R3 = 3-CN, 6-Me


718
R2 = Me, Z = O, R3 = 3-CN, 6-F


719
R2 = Me, Z = O, R3 = 3-CN, 6-Br


720
R2 = Me, Z = O, R3 = 3-CN, 6-OMe


721
R2 = Me, Z = O, R3 = 3-CN, 6-CF3


722
R2 = CN, Z = O, R3 = H (m = 0)


723
R2 = CN, Z = O, R3 = 3-F


724
R2 = CN, Z = O, R3 = 3-Cl


725
R2 = CN, Z = O, R3 = 3-Br


726
R2 = CN, Z = O, R3 = 3-I


727
R2 = CN, Z = O, R3 = 3-CN


728
R2 = CN, Z = O, R3 = 3-NO2


729
R2 = CN, Z = O, R3 = 3-OMe


730
R2 = CN, Z = O, R3 = 3-OCF3


731
R2 = CN, Z = O, R3 = 3-CF3


732
R2 = CN, Z = O, R3 = 3-CHF2


733
R2 = CN, Z = O, R3 = 3-CH2F


734
R2 = CN, Z = O, R3 = 3-CHO


735
R2 = CN, Z = O, R3 = 3-Me


736
R2 = CN, Z = O, R3 = 3-Et


737
R2 = CN, Z = O, R3 = 3-Ethynyl


738
R2 = CN, Z = O, R3 = 3-Ethenyl


739
R2 = CN, Z = O, R3 = 3-SO2Me


740
R2 = CN, Z = O, R3 = 3-OAc


741
R2 = CN, Z = O, R3 = 3-c-Pr


742
R2 = CN, Z = O, R3 = 3-i-Pr


743
R2 = CN, Z = O, R3 = 3-Ph


744
R2 = CN, Z = S, R3 = 3-F


745
R2 = CN, Z = S, R3 = 3-Cl


746
R2 = CN, Z = S, R3 = 3-Br


747
R2 = CN, Z = S, R3 = 3-I


748
R2 = CN, Z = S, R3 = 3-CN


749
R2 = CN, Z = S, R3 = 3-NO2


750
R2 = CN, Z = S, R3 = 3-OMe


751
R2 = CN, Z = S, R3 = 3-OCF3


752
R2 = CN, Z = S, R3 = 3-CF3


753
R2 = CN, Z = S, R3 = 3-CHF2


754
R2 = CN, Z = S, R3 = 3-CH2F


755
R2 = CN, Z = S, R3 = 3-CHO


756
R2 = CN, Z = S, R3 = 3-Me


757
R2 = CN, Z = S, R3 = 3-Et


758
R2 = CN, Z = S, R3 = 3-Ethynyl


759
R2 = CN, Z = S, R3 = 3-Ethenyl


760
R2 = CN, Z = S, R3 = 3-SO2Me


761
R2 = CN, Z = S, R3 = 3-OAc


762
R2 = CN, Z = S, R3 = 3-c-Pr


763
R2 = CN, Z = S, R3 = 3-i-Pr


764
R2 = CN, Z = S, R3 = 3-Ph


765
R2 = CN, Z = O, R3 = 4-F


766
R2 = CN, Z = O, R3 = 4-Cl


767
R2 = CN, Z = O, R3 = 4-Br


768
R2 = CN, Z = O, R3 = 4-I


769
R2 = CN, Z = O, R3 = 4-CN


770
R2 = CN, Z = O, R3 = 4-NO2


771
R2 = CN, Z = O, R3 = 4-OMe


772
R2 = CN, Z = O, R3 = 4-OCF3


773
R2 = CN, Z = O, R3 = 4-CF3


774
R2 = CN, Z = O, R3 = 4-CHF2


775
R2 = CN, Z = O, R3 = 4-CH2F


776
R2 = CN, Z = O, R3 = 4-CHO


777
R2 = CN, Z = O, R3 = 4-Me


778
R2 = CN, Z = O, R3 = 4-Et


779
R2 = CN, Z = O, R3 = 4-Ethynyl


780
R2 = CN, Z = O, R3 = 4-Ethenyl


781
R2 = CN, Z = O, R3 = 4-SO2Me


782
R2 = CN, Z = O, R3 = 4-OAc


783
R2 = CN, Z = O, R3 = 4-c-Pr


784
R2 = CN, Z = O, R3 = 4-i-Pr


785
R2 = CN, Z = O, R3 = 4-Ph


786
R2 = CN, Z = O, R3 = 5-F


787
R2 = CN, Z = O, R3 = 5-Cl


788
R2 = CN, Z = O, R3 = 5-Br


789
R2 = CN, Z = O, R3 = 5-I


790
R2 = CN, Z = O, R3 = 5-CN


791
R2 = CN, Z = O, R3 = 5-NO2


792
R2 = CN, Z = O, R3 = 5-OMe


793
R2 = CN, Z = O, R3 = 5-OCF3


794
R2 = CN, Z = O, R3 = 5-CF3


795
R2 = CN, Z = O, R3 = 5-CHF2


796
R2 = CN, Z = O, R3 = 5-CH2F


797
R2 = CN, Z = O, R3 = 5-CHO


798
R2 = CN, Z = O, R3 = 5-Me


799
R2 = CN, Z = O, R3 = 5-Et


800
R2 = CN, Z = O, R3 = 5-Ethynyl


801
R2 = CN, Z = O, R3 = 5-Ethenyl


802
R2 = CN, Z = O, R3 = 5-SO2Me


803
R2 = CN, Z = O, R3 = 5-OAc


804
R2 = CN, Z = O, R3 = 5-c-Pr


805
R2 = CN, Z = O, R3 = 5-i-Pr


806
R2 = CN, Z = O, R3 = 5-Ph


807
R2 = CN, Z = O, R3 = 6-F


808
R2 = CN, Z = O, R3 = 6-Cl


809
R2 = CN, Z = O, R3 = 6-Br


810
R2 = CN, Z = O, R3 = 6-I


811
R2 = CN, Z = O, R3 = 6-CN


812
R2 = CN, Z = O, R3 = 6-NO2


813
R2 = CN, Z = O, R3 = 6-OMe


814
R2 = CN, Z = O, R3 = 6-OCF3


815
R2 = CN, Z = O, R3 = 6-CF3


816
R2 = CN, Z = O, R3 = 6-CHF2


817
R2 = CN, Z = O, R3 = 6-CH2F


818
R2 = CN, Z = O, R3 = 6-CHO


819
R2 = CN, Z = O, R3 = 6-Me


820
R2 = CN, Z = O, R3 = 6-Et


821
R2 = CN, Z = O, R3 = 6-Ethynyl


822
R2 = CN, Z = O, R3 = 6-Ethenyl


823
R2 = CN, Z = O, R3 = 6-SO2Me


824
R2 = CN, Z = O, R3 = 6-OAc


825
R2 = CN, Z = O, R3 = 6-c-Pr


826
R2 = CN, Z = O, R3 = 6-i-Pr


827
R2 = CN, Z = O, R3 = 6-Ph


828
R2 = CN, Z = O, R3 = 3,4-di-F


829
R2 = CN, Z = O, R3 = 3,5-di-F


830
R2 = CN, Z = O, R3 = 3,6-di-F


831
R2 = CN, Z = O, R3 = 4,5-di-F


832
R2 = CN, Z = O, R3 = 3,4-di-Cl


833
R2 = CN, Z = O, R3 = 3,5-di-Cl


834
R2 = CN, Z = O, R3 = 3,6-di-Cl


835
R2 = CN, Z = O, R3 = 4,5-di-Cl


836
R2 = CN, Z = O, R3 = 3,4-di-Br


837
R2 = CN, Z = O, R3 = 3,5-di-Br


838
R2 = CN, Z = O, R3 = 3,6-di-Br


839
R2 = CN, Z = O, R3 = 4,5-di-Br


840
R2 = CN, Z = O, R3 = 3,4-di-CN


841
R2 = CN, Z = O, R3 = 3,5-di-CN


842
R2 = CN, Z = O, R3 = 3,6-di-CN


843
R2 = CN, Z = O, R3 = 4,5-di-CN


844
R2 = CN, Z = O, R3 = 3,4-di-Me


845
R2 = CN, Z = O, R3 = 3,5-di-Me


846
R2 = CN, Z = O, R3 = 3,6-di-Me


847
R2 = CN, Z = O, R3 = 4,5-di-Me


848
R2 = CN, Z = O, R3 = 3,4-di-OMe


849
R2 = CN, Z = O, R3 = 3,5-di-OMe


850
R2 = CN, Z = O, R3 = 3,6-di-OMe


851
R2 = CN, Z = O, R3 = 4,5-di-OMe


852
R2 = CN, Z = O, R3 = 3,4-di-CF3


853
R2 = CN, Z = O, R3 = 3,5-di-CF3


854
R2 = CN, Z = O, R3 = 3,6-di-CF3


855
R2 = CN, Z = O, R3 = 4,5-di-CF3


856
R2 = CN, Z = O, R3 = 3-CN, 4-Me


857
R2 = CN, Z = O, R3 = 3-CN, 4-F


858
R2 = CN, Z = O, R3 = 3-CN, 4-Br


859
R2 = CN, Z = O, R3 = 3-CN, 4-OMe


860
R2 = CN, Z = O, R3 = 3-CN, 4-CF3


861
R2 = CN, Z = O, R3 = 3-CN, 6-Me


862
R2 = CN, Z = O, R3 = 3-CN, 6-F


863
R2 = CN, Z = O, R3 = 3-CN, 6-Br


864
R2 = CN, Z = O, R3 = 3-CN, 6-OMe


865
R2 = CN, Z = O, R3 = 3-CN, 6-CF3


866
R2 = NO2, Z = O, R3 = H (m = 0)


867
R2 = NO2, Z = O, R3 = 3-F


868
R2 = NO2, Z = O, R3 = 3-Cl


869
R2 = NO2, Z = O, R3 = 3-Br


870
R2 = NO2, Z = O, R3 = 3-I


871
R2 = NO2, Z = O, R3 = 3-CN


872
R2 = NO2, Z = O, R3 = 3-NO2


873
R2 = NO2, Z = O, R3 = 3-OMe


874
R2 = NO2, Z = O, R3 = 3-OCF3


875
R2 = NO2, Z = O, R3 = 3-CF3


876
R2 = NO2, Z = O, R3 = 3-CHF2


877
R2 = NO2, Z = O, R3 = 3-CH2F


878
R2 = NO2, Z = O, R3 = 3-CHO


879
R2 = NO2, Z = O, R3 = 3-Me


880
R2 = NO2, Z = O, R3 = 3-Et


881
R2 = NO2, Z = O, R3 = 3-Ethynyl


882
R2 = NO2, Z = O, R3 = 3-Ethenyl


883
R2 = NO2, Z = O, R3 = 3-SO2Me


884
R2 = NO2, Z = O, R3 = 3-OAc


885
R2 = NO2, Z = O, R3 = 3-c-Pr


886
R2 = NO2, Z = O, R3 = 3-i-Pr


887
R2 = NO2, Z = O, R3 = 3-Ph


888
R2 = NO2, Z = S, R3 = 3-F


889
R2 = NO2, Z = S, R3 = 3-Cl


890
R2 = NO2, Z = S, R3 = 3-Br


891
R2 = NO2, Z = S, R3 = 3-I


892
R2 = NO2, Z = S, R3 = 3-CN


893
R2 = NO2, Z = S, R3 = 3-NO2


894
R2 = NO2, Z = S, R3 = 3-OMe


895
R2 = NO2, Z = S, R3 = 3-OCF3


896
R2 = NO2, Z = S, R3 = 3-CF3


897
R2 = NO2, Z = S, R3 = 3-CHF2


898
R2 = NO2, Z = S, R3 = 3-CH2F


899
R2 = NO2, Z = S, R3 = 3-CHO


900
R2 = NO2, Z = S, R3 = 3-Me


901
R2 = NO2, Z = S, R3 = 3-Et


902
R2 = NO2, Z = S, R3 = 3-Ethynyl


903
R2 = NO2, Z = S, R3 = 3-Ethenyl


904
R2 = NO2, Z = S, R3 = 3-SO2Me


905
R2 = NO2, Z = S, R3 = 3-OAc


906
R2 = NO2, Z = S, R3 = 3-c-Pr


907
R2 = NO2, Z = S, R3 = 3-i-Pr


908
R2 = NO2, Z = S, R3 = 3-Ph


909
R2 = NO2, Z = O, R3 = 4-F


910
R2 = NO2, Z = O, R3 = 4-Cl


911
R2 = NO2, Z = O, R3 = 4-Br


912
R2 = NO2, Z = O, R3 = 4-I


913
R2 = NO2, Z = O, R3 = 4-CN


914
R2 = NO2, Z = O, R3 = 4-NO2


915
R2 = NO2, Z = O, R3 = 4-OMe


916
R2 = NO2, Z = O, R3 = 4-OCF3


917
R2 = NO2, Z = O, R3 = 4-CF3


918
R2 = NO2, Z = O, R3 = 4-CHF2


919
R2 = NO2, Z = O, R3 = 4-CH2F


920
R2 = NO2, Z = O, R3 = 4-CHO


921
R2 = NO2, Z = O, R3 = 4-Me


922
R2 = NO2, Z = O, R3 = 4-Et


923
R2 = NO2, Z = O, R3 = 4-Ethynyl


924
R2 = NO2, Z = O, R3 = 4-Ethenyl


925
R2 = NO2, Z = O, R3 = 4-SO2Me


926
R2 = NO2, Z = O, R3 = 4-OAc


927
R2 = NO2, Z = O, R3 = 4-c-Pr


928
R2 = NO2, Z = O, R3 = 4-i-Pr


929
R2 = NO2, Z = O, R3 = 4-Ph


930
R2 = NO2, Z = O, R3 = 5-F


931
R2 = NO2, Z = O, R3 = 5-Cl


932
R2 = NO2, Z = O, R3 = 5-Br


933
R2 = NO2, Z = O, R3 = 5-I


934
R2 = NO2, Z = O, R3 = 5-CN


935
R2 = NO2, Z = O, R3 = 5-NO2


936
R2 = NO2, Z = O, R3 = 5-OMe


937
R2 = NO2, Z = O, R3 = 5-OCF3


938
R2 = NO2, Z = O, R3 = 5-CF3


939
R2 = NO2, Z = O, R3 = 5-CHF2


940
R2 = NO2, Z = O, R3 = 5-CH2F


941
R2 = NO2, Z = O, R3 = 5-CHO


942
R2 = NO2, Z = O, R3 = 5-Me


943
R2 = NO2, Z = O, R3 = 5-Et


944
R2 = NO2, Z = O, R3 = 5-Ethynyl


945
R2 = NO2, Z = O, R3 = 5-Ethenyl


946
R2 = NO2, Z = O, R3 = 5-SO2Me


947
R2 = NO2, Z = O, R3 = 5-OAc


948
R2 = NO2, Z = O, R3 = 5-c-Pr


949
R2 = NO2, Z = O, R3 = 5-i-Pr


950
R2 = NO2, Z = O, R3 = 5-Ph


951
R2 = NO2, Z = O, R3 = 6-F


952
R2 = NO2, Z = O, R3 = 6-Cl


953
R2 = NO2, Z = O, R3 = 6-Br


954
R2 = NO2, Z = O, R3 = 6-I


955
R2 = NO2, Z = O, R3 = 6-CN


956
R2 = NO2, Z = O, R3 = 6-NO2


957
R2 = NO2, Z = O, R3 = 6-OMe


958
R2 = NO2, Z = O, R3 = 6-OCF3


959
R2 = NO2, Z = O, R3 = 6-CF3


960
R2 = NO2, Z = O, R3 = 6-CHF2


961
R2 = NO2, Z = O, R3 = 6-CH2F


962
R2 = NO2, Z = O, R3 = 6-CHO


963
R2 = NO2, Z = O, R3 = 6-Me


964
R2 = NO2, Z = O, R3 = 6-Et


965
R2 = NO2, Z = O, R3 = 6-Ethynyl


966
R2 = NO2, Z = O, R3 = 6-Ethenyl


967
R2 = NO2, Z = O, R3 = 6-SO2Me


968
R2 = NO2, Z = O, R3 = 6-OAc


969
R2 = NO2, Z = O, R3 = 6-c-Pr


970
R2 = NO2, Z = O, R3 = 6-i-Pr


971
R2 = NO2, Z = O, R3 = 6-Ph


972
R2 = NO2, Z = O, R3 = 3,4-di-F


973
R2 = NO2, Z = O, R3 = 3,5-di-F


974
R2 = NO2, Z = O, R3 = 3,6-di-F


975
R2 = NO2, Z = O, R3 = 4,5-di-F


976
R2 = NO2, Z = O, R3 = 3,4-di-Cl


977
R2 = NO2, Z = O, R3 = 3,5-di-Cl


978
R2 = NO2, Z = O, R3 = 3,6-di-Cl


979
R2 = NO2, Z = O, R3 = 4,5-di-Cl


980
R2 = NO2, Z = O, R3 = 3,4-di-Br


981
R2 = NO2, Z = O, R3 = 3,5-di-Br


982
R2 = NO2, Z = O, R3 = 3,6-di-Br


983
R2 = NO2, Z = O, R3 = 4,5-di-Br


984
R2 = NO2, Z = O, R3 = 3,4-di-CN


985
R2 = NO2, Z = O, R3 = 3,5-di-CN


986
R2 = NO2, Z = O, R3 = 3,6-di-CN


987
R2 = NO2, Z = O, R3 = 4,5-di-CN


988
R2 = NO2, Z = O, R3 = 3,4-di-Me


989
R2 = NO2, Z = O, R3 = 3,5-di-Me


990
R2 = NO2, Z = O, R3 = 3,6-di-Me


991
R2 = NO2, Z = O, R3 = 4,5-di-Me


992
R2 = NO2, Z = O, R3 = 3,4-di-OMe


993
R2 = NO2, Z = O, R3 = 3,5-di-OMe


994
R2 = NO2, Z = O, R3 = 3,6-di-OMe


995
R2 = NO2, Z = O, R3 = 4,5-di-OMe


996
R2 = NO2, Z = O, R3 = 3,4-di-CF3


997
R2 = NO2, Z = O, R3 = 3,5-di-CF3


998
R2 = NO2, Z = O, R3 = 3,6-di-CF3


999
R2 = NO2, Z = O, R3 = 4,5-di-CF3


1000
R2 = NO2, Z = O, R3 = 3-CN, 4-Me


1001
R2 = NO2, Z = O, R3 = 3-CN, 4-F


1002
R2 = NO2, Z = O, R3 = 3-CN, 4-Br


1003
R2 = NO2, Z = O, R3 = 3-CN, 4-OMe


1004
R2 = NO2, Z = O, R3 = 3-CN, 4-CF3


1005
R2 = NO2, Z = O, R3 = 3-CN, 6-Me


1006
R2 = NO2, Z = O, R3 = 3-CN, 6-F


1007
R2 = NO2, Z = O, R3 = 3-CN, 6-Br


1008
R2 = NO2, Z = O, R3 = 3-CN, 6-OMe


1009
R2 = NO2, Z = O, R3 = 3-CN, 6-CF3


1010
R2 = OMe, Z = O, R3 = H (m = 0)


1011
R2 = OMe, Z = O, R3 = 3-F


1012
R2 = OMe, Z = O, R3 = 3-Cl


1013
R2 = OMe, Z = O, R3 = 3-Br


1014
R2 = OMe, Z = O, R3 = 3-I


1015
R2 = OMe, Z = O, R3 = 3-CN


1016
R2 = OMe, Z = O, R3 = 3-NO2


1017
R2 = OMe, Z = O, R3 = 3-OMe


1018
R2 = OMe, Z = O, R3 = 3-OCF3


1019
R2 = OMe, Z = O, R3 = 3-CF3


1020
R2 = OMe, Z = O, R3 = 3-CHF2


1021
R2 = OMe, Z = O, R3 = 3-CH2F


1022
R2 = OMe, Z = O, R3 = 3-CHO


1023
R2 = OMe, Z = O, R3 = 3-Me


1024
R2 = OMe, Z = O, R3 = 3-Et


1025
R2 = OMe, Z = O, R3 = 3-Ethynyl


1026
R2 = OMe, Z = O, R3 = 3-Ethenyl


1027
R2 = OMe, Z = O, R3 = 3-SO2Me


1028
R2 = OMe, Z = O, R3 = 3-OAc


1029
R2 = OMe, Z = O, R3 = 3-c-Pr


1030
R2 = OMe, Z = O, R3 = 3-i-Pr


1031
R2 = OMe, Z = O, R3 = 3-Ph


1032
R2 = OMe, Z = S, R3 = 3-F


1033
R2 = OMe, Z = S, R3 = 3-Cl


1034
R2 = OMe, Z = S, R3 = 3-Br


1035
R2 = OMe, Z = S, R3 = 3-I


1036
R2 = OMe, Z = S, R3 = 3-CN


1037
R2 = OMe, Z = S, R3 = 3-NO2


1038
R2 = OMe, Z = S, R3 = 3-OMe


1039
R2 = OMe, Z = S, R3 = 3-OCF3


1040
R2 = OMe, Z = S, R3 = 3-CF3


1041
R2 = OMe, Z = S, R3 = 3-CHF2


1042
R2 = OMe, Z = S, R3 = 3-CH2F


1043
R2 = OMe, Z = S, R3 = 3-CHO


1044
R2 = OMe, Z = S, R3 = 3-Me


1045
R2 = OMe, Z = S, R3 = 3-Et


1046
R2 = OMe, Z = S, R3 = 3-Ethynyl


1047
R2 = OMe, Z = S, R3 = 3-Ethenyl


1048
R2 = OMe, Z = S, R3 = 3-SO2Me


1049
R2 = OMe, Z = S, R3 = 3-OAc


1050
R2 = OMe, Z = S, R3 = 3-c-Pr


1051
R2 = OMe, Z = S, R3 = 3-i-Pr


1052
R2 = OMe, Z = S, R3 = 3-Ph


1053
R2 = OMe, Z = O, R3 = 4-F


1054
R2 = OMe, Z = O, R3 = 4-Cl


1055
R2 = OMe, Z = O, R3 = 4-Br


1056
R2 = OMe, Z = O, R3 = 4-I


1057
R2 = OMe, Z = O, R3 = 4-CN


1058
R2 = OMe, Z = O, R3 = 4-NO2


1059
R2 = OMe, Z = O, R3 = 4-OMe


1060
R2 = OMe, Z = O, R3 = 4-OCF3


1061
R2 = OMe, Z = O, R3 = 4-CF3


1062
R2 = OMe, Z = O, R3 = 4-CHF2


1063
R2 = OMe, Z = O, R3 = 4-CH2F


1064
R2 = OMe, Z = O, R3 = 4-CHO


1065
R2 = OMe, Z = O, R3 = 4-Me


1066
R2 = OMe, Z = O, R3 = 4-Et


1067
R2 = OMe, Z = O, R3 = 4-Ethynyl


1068
R2 = OMe, Z = O, R3 = 4-Ethenyl


1069
R2 = OMe, Z = O, R3 = 4-SO2Me


1070
R2 = OMe, Z = O, R3 = 4-OAc


1071
R2 = OMe, Z = O, R3 = 4-c-Pr


1072
R2 = OMe, Z = O, R3 = 4-i-Pr


1073
R2 = OMe, Z = O, R3 = 4-Ph


1074
R2 = OMe, Z = O, R3 = 5-F


1075
R2 = OMe, Z = O, R3 = 5-Cl


1076
R2 = OMe, Z = O, R3 = 5-Br


1077
R2 = OMe, Z = O, R3 = 5-I


1078
R2 = OMe, Z = O, R3 = 5-CN


1079
R2 = OMe, Z = O, R3 = 5-NO2


1080
R2 = OMe, Z = O, R3 = 5-OMe


1081
R2 = OMe, Z = O, R3 = 5-OCF3


1082
R2 = OMe, Z = O, R3 = 5-CF3


1083
R2 = OMe, Z = O, R3 = 5-CHF2


1084
R2 = OMe, Z = O, R3 = 5-CH2F


1085
R2 = OMe, Z = O, R3 = 5-CHO


1086
R2 = OMe, Z = O, R3 = 5-Me


1087
R2 = OMe, Z = O, R3 = 5-Et


1088
R2 = OMe, Z = O, R3 = 5-Ethynyl


1089
R2 = OMe, Z = O, R3 = 5-Ethenyl


1090
R2 = OMe, Z = O, R3 = 5-SO2Me


1091
R2 = OMe, Z = O, R3 = 5-OAc


1092
R2 = OMe, Z = O, R3 = 5-c-Pr


1093
R2 = OMe, Z = O, R3 = 5-i-Pr


1094
R2 = OMe, Z = O, R3 = 5-Ph


1095
R2 = OMe, Z = O, R3 = 6-F


1096
R2 = OMe, Z = O, R3 = 6-Cl


1097
R2 = OMe, Z = O, R3 = 6-Br


1098
R2 = OMe, Z = O, R3 = 6-I


1099
R2 = OMe, Z = O, R3 = 6-CN


1100
R2 = OMe, Z = O, R3 = 6-NO2


1101
R2 = OMe, Z = O, R3 = 6-OMe


1102
R2 = OMe, Z = O, R3 = 6-OCF3


1103
R2 = OMe, Z = O, R3 = 6-CF3


1104
R2 = OMe, Z = O, R3 = 6-CHF2


1105
R2 = OMe, Z = O, R3 = 6-CH2F


1106
R2 = OMe, Z = O, R3 = 6-CHO


1107
R2 = OMe, Z = O, R3 = 6-Me


1108
R2 = OMe, Z = O, R3 = 6-Et


1109
R2 = OMe, Z = O, R3 = 6-Ethynyl


1110
R2 = OMe, Z = O, R3 = 6-Ethenyl


1111
R2 = OMe, Z = O, R3 = 6-SO2Me


1112
R2 = OMe, Z = O, R3 = 6-OAc


1113
R2 = OMe, Z = O, R3 = 6-c-Pr


1114
R2 = OMe, Z = O, R3 = 6-i-Pr


1115
R2 = OMe, Z = O, R3 = 6-Ph


1116
R2 = OMe, Z = O, R3 = 3,4-di-F


1117
R2 = OMe, Z = O, R3 = 3,5-di-F


1118
R2 = OMe, Z = O, R3 = 3,6-di-F


1119
R2 = OMe, Z = O, R3 = 4,5-di-F


1120
R2 = OMe, Z = O, R3 = 3,4-di-Cl


1121
R2 = OMe, Z = O, R3 = 3,5-di-Cl


1122
R2 = OMe, Z = O, R3 = 3,6-di-Cl


1123
R2 = OMe, Z = O, R3 = 4,5-di-Cl


1124
R2 = OMe, Z = O, R3 = 3,4-di-Br


1125
R2 = OMe, Z = O, R3 = 3,5-di-Br


1126
R2 = OMe, Z = O, R3 = 3,6-di-Br


1127
R2 = OMe, Z = O, R3 = 4,5-di-Br


1128
R2 = OMe, Z = O, R3 = 3,4-di-CN


1129
R2 = OMe, Z = O, R3 = 3,5-di-CN


1130
R2 = OMe, Z = O, R3 = 3,6-di-CN


1131
R2 = OMe, Z = O, R3 = 4,5-di-CN


1132
R2 = OMe, Z = O, R3 = 3,4-di-Me


1133
R2 = OMe, Z = O, R3 = 3,5-di-Me


1134
R2 = OMe, Z = O, R3 = 3,6-di-Me


1135
R2 = OMe, Z = O, R3 = 4,5-di-Me


1136
R2 = OMe, Z = O, R3 = 3,4-di-OMe


1137
R2 = OMe, Z = O, R3 = 3,5-di-OMe


1138
R2 = OMe, Z = O, R3 = 3,6-di-OMe


1139
R2 = OMe, Z = O, R3 = 4,5-di-OMe


1140
R2 = OMe, Z = O, R3 = 3,4-di-CF3


1141
R2 = OMe, Z = O, R3 = 3,5-di-CF3


1142
R2 = OMe, Z = O, R3 = 3,6-di-CF3


1143
R2 = OMe, Z = O, R3 = 4,5-di-CF3


1144
R2 = OMe, Z = O, R3 = 3-CN, 4-Me


1145
R2 = OMe, Z = O, R3 = 3-CN, 4-F


1146
R2 = OMe, Z = O, R3 = 3-CN, 4-Br


1147
R2 = OMe, Z = O, R3 = 3-CN, 4-OMe


1148
R2 = OMe, Z = O, R3 = 3-CN, 4-CF3


1149
R2 = OMe, Z = O, R3 = 3-CN, 6-Me


1150
R2 = OMe, Z = O, R3 = 3-CN, 6-F


1151
R2 = OMe, Z = O, R3 = 3-CN, 6-Br


1152
R2 = OMe, Z = O, R3 = 3-CN, 6-OMe


1153
R2 = OMe, Z = O, R3 = 3-CN, 6-CF3


1154
R2 = CF3, Z = O, R3 = H (m = O)


1155
R2 = CF3, Z = O, R3 = 3-F


1156
R2 = CF3, Z = O, R3 = 3-Cl


1157
R2 = CF3, Z = O, R3 = 3-Br


1158
R2 = CF3, Z = O, R3 = 3-I


1159
R2 = CF3, Z = O, R3 = 3-CN


1160
R2 = CF3, Z = O, R3 = 3-NO2


1161
R2 = CF3, Z = O, R3 = 3-OMe


1162
R2 = CF3, Z = O, R3 = 3-OCF3


1163
R2 = CF3, Z = O, R3 = 3-CF3


1164
R2 = CF3, Z = O, R3 = 3-CHF2


1165
R2 = CF3, Z = O, R3 = 3-CH2F


1166
R2 = CF3, Z = O, R3 = 3-CHO


1167
R2 = CF3, Z = O, R3 = 3-Me


1168
R2 = CF3, Z = O, R3 = 3-Et


1169
R2 = CF3, Z = O, R3 = 3-Ethynyl


1170
R2 = CF3, Z = O, R3 = 3-Ethenyl


1171
R2 = CF3, Z = O, R3 = 3-SO2Me


1172
R2 = CF3, Z = O, R3 = 3-OAc


1173
R2 = CF3, Z = O, R3 = 3-c-Pr


1174
R2 = CF3, Z = O, R3 = 3-i-Pr


1175
R2 = CF3, Z = O, R3 = 3-Ph


1176
R2 = CF3, Z = S, R3 = 3-F


1177
R2 = CF3, Z = S, R3 = 3-Cl


1178
R2 = CF3, Z = S, R3 = 3-Br


1179
R2 = CF3, Z = S, R3 = 3-I


1180
R2 = CF3, Z = S, R3 = 3-CN


1181
R2 = CF3, Z = S, R3 = 3-NO2


1182
R2 = CF3, Z = S, R3 = 3-OMe


1183
R2 = CF3, Z = S, R3 = 3-OCF3


1184
R2 = CF3, Z = S, R3 = 3-CF3


1185
R2 = CF3, Z = S, R3 = 3-CHF2


1186
R2 = CF3, Z = S, R3 = 3-CH2F


1187
R2 = CF3, Z = S, R3 = 3-CHO


1188
R2 = CF3, Z = S, R3 = 3-Me


1189
R2 = CF3, Z = S, R3 = 3-Et


1190
R2 = CF3, Z = S, R3 = 3-Ethynyl


1191
R2 = CF3, Z = S, R3 = 3-Ethenyl


1192
R2 = CF3, Z = S, R3 = 3-SO2Me


1193
R2 = CF3, Z = S, R3 = 3-OAc


1194
R2 = CF3, Z = S, R3 = 3-c-Pr


1195
R2 = CF3, Z = S, R3 = 3-i-Pr


1196
R2 = CF3, Z = S, R3 = 3-Ph


1197
R2 = CF3, Z = O, R3 = 4-F


1198
R2 = CF3, Z = O, R3 = 4-Cl


1199
R2 = CF3, Z = O, R3 = 4-Br


1200
R2 = CF3, Z = O, R3 = 4-I


1201
R2 = CF3, Z = O, R3 = 4-CN


1202
R2 = CF3, Z = O, R3 = 4-NO2


1203
R2 = CF3, Z = O, R3 = 4-OMe


1204
R2 = CF3, Z = O, R3 = 4-OCF3


1205
R2 = CF3, Z = O, R3 = 4-CF3


1206
R2 = CF3, Z = O, R3 = 4-CHF2


1207
R2 = CF3, Z = O, R3 = 4-CH2F


1208
R2 = CF3, Z = O, R3 = 4-CHO


1209
R2 = CF3, Z = O, R3 = 4-Me


1210
R2 = CF3, Z = O, R3 = 4-Et


1211
R2 = CF3, Z = O, R3 = 4-Ethynyl


1212
R2 = CF3, Z = O, R3 = 4-Ethenyl


1213
R2 = CF3, Z = O, R3 = 4-SO2Me


1214
R2 = CF3, Z = O, R3 = 4-OAc


1215
R2 = CF3, Z = O, R3 = 4-c-Pr


1216
R2 = CF3, Z = O, R3 = 4-i-Pr


1217
R2 = CF3, Z = O, R3 = 4-Ph


1218
R2 = CF3, Z = O, R3 = 5-F


1219
R2 = CF3, Z = O, R3 = 5-Cl


1220
R2 = CF3, Z = O, R3 = 5-Br


1221
R2 = CF3, Z = O, R3 = 5-I


1222
R2 = CF3, Z = O, R3 = 5-CN


1223
R2 = CF3, Z = O, R3 = 5-NO2


1224
R2 = CF3, Z = O, R3 = 5-OMe


1225
R2 = CF3, Z = O, R3 = 5-OCF3


1226
R2 = CF3, Z = O, R3 = 5-CF3


1227
R2 = CF3, Z = O, R3 = 5-CHF2


1228
R2 = CF3, Z = O, R3 = 5-CH2F


1229
R2 = CF3, Z = O, R3 = 5-CHO


1230
R2 = CF3, Z = O, R3 = 5-Me


1231
R2 = CF3, Z = O, R3 = 5-Et


1232
R2 = CF3, Z = O, R3 = 5-Ethynyl


1233
R2 = CF3, Z = O, R3 = 5-Ethenyl


1234
R2 = CF3, Z = O, R3 = 5-SO2Me


1235
R2 = CF3, Z = O, R3 = 5-OAc


1236
R2 = CF3, Z = O, R3 = 5-c-Pr


1237
R2 = CF3, Z = O, R3 = 5-i-Pr


1238
R2 = CF3, Z = O, R3 = 5-Ph


1239
R2 = CF3, Z = O, R3 = 6-F


1240
R2 = CF3, Z = O, R3 = 6-Cl


1241
R2 = CF3, Z = O, R3 = 6-Br


1242
R2 = CF3, Z = O, R3 = 6-I


1243
R2 = CF3, Z = O, R3 = 6-CN


1244
R2 = CF3, Z = O, R3 = 6-NO2


1245
R2 = CF3, Z = O, R3 = 6-OMe


1246
R2 = CF3, Z = O, R3 = 6-OCF3


1247
R2 = CF3, Z = O, R3 = 6-CF3


1248
R2 = CF3, Z = O, R3 = 6-CHF2


1249
R2 = CF3, Z = O, R3 = 6-CH2F


1250
R2 = CF3, Z = O, R3 = 6-CHO


1251
R2 = CF3, Z = O, R3 = 6-Me


1252
R2 = CF3, Z = O, R3 = 6-Et


1253
R2 = CF3, Z = O, R3 = 6-Ethynyl


1254
R2 = CF3, Z = O, R3 = 6-Ethenyl


1255
R2 = CF3, Z = O, R3 = 6-SO2Me


1256
R2 = CF3, Z = O, R3 = 6-OAc


1257
R2 = CF3, Z = O, R3 = 6-c-Pr


1258
R2 = CF3, Z = O, R3 = 6-i-Pr


1259
R2 = CF3, Z = O, R3 = 6-Ph


1260
R2 = CF3, Z = O, R3 = 3,4-di-F


1261
R2 = CF3, Z = O, R3 = 3,5-di-F


1262
R2 = CF3, Z = O, R3 = 3,6-di-F


1263
R2 = CF3, Z = O, R3 = 4,5-di-F


1264
R2 = CF3, Z = O, R3 = 3,4-di-Cl


1265
R2 = CF3, Z = O, R3 = 3,5-di-Cl


1266
R2 = CF3, Z = O, R3 = 3,6-di-Cl


1267
R2 = CF3, Z = O, R3 = 4,5-di-Cl


1268
R2 = CF3, Z = O, R3 = 3,4-di-Br


1269
R2 = CF3, Z = O, R3 = 3,5-di-Br


1270
R2 = CF3, Z = O, R3 = 3,6-di-Br


1271
R2 = CF3, Z = O, R3 = 4,5-di-Br


1272
R2 = CF3, Z = O, R3 = 3,4-di-CN


1273
R2 = CF3, Z = O, R3 = 3,5-di-CN


1274
R2 = CF3, Z = O, R3 = 3,6-di-CN


1275
R2 = CF3, Z = O, R3 = 4,5-di-CN


1276
R2 = CF3, Z = O, R3 = 3,4-di-Me


1277
R2 = CF3, Z = O, R3 = 3,5-di-Me


1278
R2 = CF3, Z = O, R3 = 3,6-di-Me


1279
R2 = CF3, Z = O, R3 = 4,5-di-Me


1280
R2 = CF3, Z = O, R3 = 3,4-di-OMe


1281
R2 = CF3, Z = O, R3 = 3,5-di-OMe


1282
R2 = CF3, Z = O, R3 = 3,6-di-OMe


1283
R2 = CF3, Z = O, R3 = 4,5-di-OMe


1284
R2 = CF3, Z = O, R3 = 3,4-di-CF3


1285
R2 = CF3, Z = O, R3 = 3,5-di-CF3


1286
R2 = CF3, Z = O, R3 = 3,6-di-CF3


1287
R2 = CF3, Z = O, R3 = 4,5-di-CF3


1288
R2 = CF3, Z = O, R3 = 3-CN, 4-Me


1289
R2 = CF3, Z = O, R3 = 3-CN, 4-F


1290
R2 = CF3, Z = O, R3 = 3-CN, 4-Br


1291
R2 = CF3, Z = O, R3 = 3-CN, 4-OMe


1292
R2 = CF3, Z = O, R3 = 3-CN, 4-CF3


1293
R2 = CF3, Z = O, R3 = 3-CN, 6-Me


1294
R2 = CF3, Z = O, R3 = 3-CN, 6-F


1295
R2 = CF3, Z = O, R3 = 3-CN, 6-Br


1296
R2 = CF3, Z = O, R3 = 3-CN, 6-OMe


1297
R2 = CF3, Z = O, R3 = 3-CN, 6-CF3


1298
R2 = CHF2, Z = O, R3 = H (m = O)


1299
R2 = CHF2, Z = O, R3 = 3-F


1300
R2 = CHF2, Z = O, R3 = 3-Cl


1301
R2 = CHF2, Z = O, R3 = 3-Br


1302
R2 = CHF2, Z = O, R3 = 3-I


1303
R2 = CHF2, Z = O, R3 = 3-CN


1304
R2 = CHF2, Z = O, R3 = 3-NO2


1305
R2 = CHF2, Z = O, R3 = 3-OMe


1306
R2 = CHF2, Z = O, R3 = 3-OCF3


1307
R2 = CHF2, Z = O, R3 = 3-CF3


1308
R2 = CHF2, Z = O, R3 = 3-CHF2


1309
R2 = CHF2, Z = O, R3 = 3-CH2F


1310
R2 = CHF2, Z = O, R3 = 3-CHO


1311
R2 = CHF2, Z = O, R3 = 3-Me


1312
R2 = CHF2, Z = O, R3 = 3-Et


1313
R2 = CHF2, Z = O, R3 = 3-Ethynyl


1314
R2 = CHF2, Z = O, R3 = 3-Ethenyl


1315
R2 = CHF2, Z = O, R3 = 3-SO2Me


1316
R2 = CHF2, Z = O, R3 = 3-OAc


1317
R2 = CHF2, Z = O, R3 = 3-c-Pr


1318
R2 = CHF2, Z = O, R3 = 3-i-Pr


1319
R2 = CHF2, Z = O, R3 = 3-Ph


1320
R2 = CHF2, Z = S, R3 = 3-F


1321
R2 = CHF2, Z = S, R3 = 3-Cl


1322
R2 = CHF2, Z = S, R3 = 3-Br


1323
R2 = CHF2, Z = S, R3 = 3-I


1324
R2 = CHF2, Z = S, R3 = 3-CN


1325
R2 = CHF2, Z = S, R3 = 3-NO2


1326
R2 = CHF2, Z = S, R3 = 3-OMe


1327
R2 = CHF2, Z = S, R3 = 3-OCF3


1328
R2 = CHF2, Z = S, R3 = 3-CHF2


1329
R2 = CHF2, Z = S, R3 = 3-CH2F


1330
R2 = CHF2, Z = S, R3 = 3-CHO


1331
R2 = CHF2, Z = S, R3 = 3-Me


1332
R2 = CHF2, Z = S, R3 = 3-Et


1333
R2 = CHF2, Z = S, R3 = 3-Ethynyl


1334
R2 = CHF2, Z = S, R3 = 3-Ethenyl


1335
R2 = CHF2, Z = S, R3 = 3-SO2Me


1336
R2 = CHF2, Z = S, R3 = 3-OAc


1337
R2 = CHF2, Z = S, R3 = 3-c-Pr


1338
R2 = CHF2, Z = S, R3 = 3-i-Pr


1339
R2 = CHF2, Z = S, R3 = 3-Ph


1340
R2 = CHF2, Z = O, R3 = 4-F


1341
R2 = CHF2, Z = O, R3 = 4-Cl


1342
R2 = CHF2, Z = O, R3 = 4-Br


1343
R2 = CHF2, Z = O, R3 = 4-I


1344
R2 = CHF2, Z = O, R3 = 4-CN


1345
R2 = CHF2, Z = O, R3 = 4-NO2


1346
R2 = CHF2, Z = O, R3 = 4-OMe


1347
R2 = CHF2, Z = O, R3 = 4-OCF3


1348
R2 = CHF2, Z = O, R3 = 4-CF3


1349
R2 = CHF2, Z = O, R3 = 4-CHF2


1350
R2 = CHF2, Z = O, R3 = 4-CH2F


1351
R2 = CHF2, Z = O, R3 = 4-CHO


1352
R2 = CHF2, Z = O, R3 = 4-Me


1353
R2 = CHF2, Z = O, R3 = 4-Et


1354
R2 = CHF2, Z = O, R3 = 4-Ethynyl


1355
R2 = CHF2, Z = O, R3 = 4-Ethenyl


1356
R2 = CHF2, Z = O, R3 = 4-SO2Me


1357
R2 = CHF2, Z = O, R3 = 4-OAc


1358
R2 = CHF2, Z = O, R3 = 4-c-Pr


1359
R2 = CHF2, Z = O, R3 = 4-i-Pr


1360
R2 = CHF2, Z = O, R3 = 4-Ph


1361
R2 = CHF2, Z = O, R3 = 5-F


1362
R2 = CHF2, Z = O, R3 = 5-Cl


1363
R2 = CHF2, Z = O, R3 = 5-Br


1364
R2 = CHF2, Z = O, R3 = 5-I


1365
R2 = CHF2, Z = O, R3 = 5-CN


1366
R2 = CHF2, Z = O, R3 = 5-NO2


1367
R2 = CHF2, Z = O, R3 = 5-OMe


1368
R2 = CHF2, Z = O, R3 = 5-OCF3


1369
R2 = CHF2, Z = O, R3 = 5-CF3


1370
R2 = CHF2, Z = O, R3 = 5-CHF2


1371
R2 = CHF2, Z = O, R3 = 5-CH2F


1372
R2 = CHF2, Z = O, R3 = 5-CHO


1373
R2 = CHF2, Z = O, R3 = 5-Me


1374
R2 = CHF2, Z = O, R3 = 5-Et


1375
R2 = CHF2, Z = O, R3 = 5-Ethynyl


1376
R2 = CHF2, Z = O, R3 = 5-Ethenyl


1377
R2 = CHF2, Z = O, R3 = 5-SO2Me


1378
R2 = CHF2, Z = O, R3 = 5-OAc


1379
R2 = CHF2, Z = O, R3 = 5-c-Pr


1380
R2 = CHF2, Z = O, R3 = 5-i-Pr


1381
R2 = CHF2, Z = O, R3 = 5-Ph


1382
R2 = CHF2, Z = O, R3 = 6-F


1383
R2 = CHF2, Z = O, R3 = 6-Cl


1384
R2 = CHF2, Z = O, R3 = 6-Br


1385
R2 = CHF2, Z = O, R3 = 6-I


1386
R2 = CHF2, Z = O, R3 = 6-CN


1387
R2 = CHF2, Z = O, R3 = 6-NO2


1388
R2 = CHF2, Z = O, R3 = 6-OMe


1389
R2 = CHF2, Z = O, R3 = 6-OCF3


1390
R2 = CHF2, Z = O, R3 = 6-CF3


1391
R2 = CHF2, Z = O, R3 = 6-CHF2


1392
R2 = CHF2, Z = O, R3 = 6-CH2F


1393
R2 = CHF2, Z = O, R3 = 6-CHO


1394
R2 = CHF2, Z = O, R3 = 6-Me


1395
R2 = CHF2, Z = O, R3 = 6-Et


1396
R2 = CHF2, Z = O, R3 = 6-Ethynyl


1397
R2 = CHF2, Z = O, R3 = 6-Ethenyl


1398
R2 = CHF2, Z = O, R3 = 6-SO2Me


1399
R2 = CHF2, Z = O, R3 = 6-OAc


1400
R2 = CHF2, Z = O, R3 = 6-c-Pr


1401
R2 = CHF2, Z = O, R3 = 6-i-Pr


1402
R2 = CHF2, Z = O, R3 = 6-Ph


1403
R2 = CHF2, Z = O, R3 = 3,4-di-F


1404
R2 = CHF2, Z = O, R3 = 3,5-di-F


1405
R2 = CHF2, Z = O, R3 = 3,6-di-F


1406
R2 = CHF2, Z = O, R3 = 4,5-di-F


1407
R2 = CHF2, Z = O, R3 = 3,4-di-Cl


1408
R2 = CHF2, Z = O, R3 = 3,5-di-Cl


1409
R2 = CHF2, Z = O, R3 = 3,6-di-Cl


1410
R2 = CHF2, Z = O, R3 = 4,5-di-Cl


1411
R2 = CHF2, Z = O, R3 = 3,4-di-Br


1412
R2 = CHF2, Z = O, R3 = 3,5-di-Br


1413
R2 = CHF2, Z = O, R3 = 3,6-di-Br


1414
R2 = CHF2, Z = O, R3 = 4,5-di-Br


1415
R2 = CHF2, Z = O, R3 = 3,4-di-CN


1416
R2 = CHF2, Z = O, R3 = 3,5-di-CN


1417
R2 = CHF2, Z = O, R3 = 3,6-di-CN


1418
R2 = CHF2, Z = O, R3 = 4,5-di-CN


1419
R2 = CHF2, Z = O, R3 = 3,4-di-Me


1420
R2 = CHF2, Z = O, R3 = 3,5-di-Me


1421
R2 = CHF2, Z = O, R3 = 3,6-di-Me


1422
R2 = CHF2, Z = O, R3 = 4,5-di-Me


1423
R2 = CHF2, Z = O, R3 = 3,4-di-OMe


1424
R2 = CHF2, Z = O, R3 = 3,5-di-OMe


1425
R2 = CHF2, Z = O, R3 = 3,6-di-OMe


1426
R2 = CHF2, Z = O, R3 = 4,5-di-OMe


1427
R2 = CHF2, Z = O, R3 = 3,4-di-CF3


1428
R2 = CHF2, Z = O, R3 = 3,5-di-CF3


1429
R2 = CHF2, Z = O, R3 = 3,6-di-CF3


1430
R2 = CHF2, Z = O, R3 = 4,5-di-CF3


1431
R2 = CHF2, Z = O, R3 = 3-CN, 4-Me


1432
R2 = CHF2, Z = O, R3 = 3-CN, 4-F


1433
R2 = CHF2, Z = O, R3 = 3-CN, 4-Br


1434
R2 = CHF2, Z = O, R3 = 3-CN, 4-OMe


1435
R2 = CHF2, Z = O, R3 = 3-CN, 4-CF3


1436
R2 = CHF2, Z = O, R3 = 3-CN, 6-Me


1437
R2 = CHF2, Z = O, R3 = 3-CN, 6-F


1438
R2 = CHF2, Z = O, R3 = 3-CN, 6-Br


1439
R2 = CHF2, Z = O, R3 = 3-CN, 6-OMe


1440
R2 = CHF2, Z = O, R3 = 3-CN, 6-CF3


1441
R2 = SO2Me, Z = O, R3 = H (m = 0)


1442
R2 = SO2Me, Z = O, R3 = 3-F


1443
R2 = SO2Me, Z = O, R3 = 3-Cl


1444
R2 = SO2Me, Z = O, R3 = 3-Br


1445
R2 = SO2Me, Z = O, R3 = 3-I


1446
R2 = SO2Me, Z = O, R3 = 3-CN


1447
R2 = SO2Me, Z = O, R3 = 3-NO2


1448
R2 = SO2Me, Z = O, R3 = 3-OMe


1449
R2 = SO2Me, Z = O, R3 = 3-OCF3


1450
R2 = SO2Me, Z = O, R3 = 3-CF3


1451
R2 = SO2Me, Z = O, R3 = 3-CHF2


1452
R2 = SO2Me, Z = O, R3 = 3-CH2F


1453
R2 = SO2Me, Z = O, R3 = 3-CHO


1454
R2 = SO2Me, Z = O, R3 = 3-Me


1455
R2 = SO2Me, Z = O, R3 = 3-Et


1456
R2 = SO2Me, Z = O, R3 = 3-Ethynyl


1457
R2 = SO2Me, Z = O, R3 = 3-Ethenyl


1458
R2 = SO2Me, Z = O, R3 = 3-SO2Me


1459
R2 = SO2Me, Z = O, R3 = 3-OAc


1460
R2 = SO2Me, Z = O, R3 = 3-c-Pr


1461
R2 = SO2Me, Z = O, R3 = 3-i-Pr


1462
R2 = SO2Me, Z = O, R3 = 3-Ph


1463
R2 = SO2Me, Z = S, R3 = 3-F


1464
R2 = SO2Me, Z = S, R3 = 3-Cl


1465
R2 = SO2Me, Z = S, R3 = 3-Br


1466
R2 = SO2Me, Z = S, R3 = 3-I


1467
R2 = SO2Me, Z = S, R3 = 3-CN


1468
R2 = SO2Me, Z = S, R3 = 3-NO2


1469
R2 = SO2Me, Z = S, R3 = 3-OMe


1470
R2 = SO2Me, Z = S, R3 = 3-OCF3


1471
R2 = SO2Me, Z = S, R3 = 3-CF3


1472
R2 = SO2Me, Z = S, R3 = 3-CHF2


1473
R2 = SO2Me, Z = S, R3 = 3-CH2F


1474
R2 = SO2Me, Z = S, R3 = 3-CHO


1475
R2 = SO2Me, Z = S, R3 = 3-Me


1476
R2 = SO2Me, Z = S, R3 = 3-Et


1477
R2 = SO2Me, Z = S, R3 = 3-Ethynyl


1478
R2 = SO2Me, Z = S, R3 = 3-Ethenyl


1479
R2 = SO2Me, Z = S, R3 = 3-SO2Me


1480
R2 = SO2Me, Z = S, R3 = 3-OAc


1481
R2 = SO2Me, Z = S, R3 = 3-c-Pr


1482
R2 = SO2Me, Z = S, R3 = 3-i-Pr


1483
R2 = SO2Me, Z = S, R3 = 3-Ph


1484
R2 = SO2Me, Z = O, R3 = 4-F


1485
R2 = SO2Me, Z = O, R3 = 4-Cl


1486
R2 = SO2Me, Z = O, R3 = 4-Br


1487
R2 = SO2Me, Z = O, R3 = 4-I


1488
R2 = SO2Me, Z = O, R3 = 4-CN


1489
R2 = SO2Me, Z = O, R3 = 4-NO2


1490
R2 = SO2Me, Z = O, R3 = 4-OMe


1491
R2 = SO2Me, Z = O, R3 = 4-OCF3


1492
R2 = SO2Me, Z = O, R3 = 4-CF3


1493
R2 = SO2Me, Z = O, R3 = 4-CHF2


1494
R2 = SO2Me, Z = O, R3 = 4-CH2F


1495
R2 = SO2Me, Z = O, R3 = 4-CHO


1496
R2 = SO2Me, Z = O, R3 = 4-Me


1497
R2 = SO2Me, Z = O, R3 = 4-Et


1498
R2 = SO2Me, Z = O, R3 = 4-Ethynyl


1499
R2 = SO2Me, Z = O, R3 = 4-Ethenyl


1500
R2 = SO2Me, Z = O, R3 = 4-SO2Me


1501
R2 = SO2Me, Z = O, R3 = 4-OAc


1502
R2 = SO2Me, Z = O, R3 = 4-c-Pr


1503
R2 = SO2Me, Z = O, R3 = 4-i-Pr


1504
R2 = SO2Me, Z = O, R3 = 4-Ph


1505
R2 = SO2Me, Z = O, R3 = 5-F


1506
R2 = SO2Me, Z = O, R3 = 5-Cl


1507
R2 = SO2Me, Z = O, R3 = 5-Br


1508
R2 = SO2Me, Z = O, R3 = 5-I


1509
R2 = SO2Me, Z = O, R3 = 5-CN


1510
R2 = SO2Me, Z = O, R3 = 5-NO2


1511
R2 = SO2Me, Z = O, R3 = 5-OMe


1512
R2 = SO2Me, Z = O, R3 = 5-OCF3


1513
R2 = SO2Me, Z = O, R3 = 5-CF3


1514
R2 = SO2Me, Z = O, R3 = 5-CHF2


1515
R2 = SO2Me, Z = O, R3 = 5-CH2F


1516
R2 = SO2Me, Z = O, R3 = 5-CHO


1517
R2 = SO2Me, Z = O, R3 = 5-Me


1518
R2 = SO2Me, Z = O, R3 = 5-Et


1519
R2 = SO2Me, Z = O, R3 = 5-Ethynyl


1520
R2 = SO2Me, Z = O, R3 = 5-Ethenyl


1521
R2 = SO2Me, Z = O, R3 = 5-SO2Me


1522
R2 = SO2Me, Z = O, R3 = 5-OAc


1523
R2 = SO2Me, Z = O, R3 = 5-c-Pr


1524
R2 = SO2Me, Z = O, R3 = 5-i-Pr


1525
R2 = SO2Me, Z = O, R3 = 5-Ph


1526
R2 = SO2Me, Z = O, R3 = 6-F


1527
R2 = SO2Me, Z = O, R3 = 6-Cl


1528
R2 = SO2Me, Z = O, R3 = 6-Br


1529
R2 = SO2Me, Z = O, R3 = 6-I


1530
R2 = SO2Me, Z = O, R3 = 6-CN


1531
R2 = SO2Me, Z = O, R3 = 6-NO2


1532
R2 = SO2Me, Z = O, R3 = 6-OMe


1533
R2 = SO2Me, Z = O, R3 = 6-OCF3


1534
R2 = SO2Me, Z = O, R3 = 6-CF3


1535
R2 = SO2Me, Z = O, R3 = 6-CHF2


1536
R2 = SO2Me, Z = O, R3 = 6-CH2F


1537
R2 = SO2Me, Z = O, R3 = 6-CHO


1538
R2 = SO2Me, Z = O, R3 = 6-Me


1539
R2 = SO2Me, Z = O, R3 = 6-Et


1540
R2 = SO2Me, Z = O, R3 = 6-Ethynyl


1541
R2 = SO2Me, Z = O, R3 = 6-Ethenyl


1542
R2 = SO2Me, Z = O, R3 = 6-SO2Me


1543
R2 = SO2Me, Z = O, R3 = 6-OAc


1544
R2 = SO2Me, Z = O, R3 = 6-c-Pr


1545
R2 = SO2Me, Z = O, R3 = 6-i-Pr


1546
R2 = SO2Me, Z = O, R3 = 6-Ph


1547
R2 = SO2Me, Z = O, R3 = 3,4-di-F


1548
R2 = SO2Me, Z = O, R3 = 3,5-di-F


1549
R2 = SO2Me, Z = O, R3 = 3,6-di-F


1550
R2 = SO2Me, Z = O, R3 = 4,5-di-F


1551
R2 = SO2Me, Z = O, R3 = 3,4-di-Cl


1552
R2 = SO2Me, Z = O, R3 = 3,5-di-Cl


1553
R2 = SO2Me, Z = O, R3 = 3,6-di-Cl


1554
R2 = SO2Me, Z = O, R3 = 4,5-di-Cl


1555
R2 = SO2Me, Z = O, R3 = 3,4-di-Br


1556
R2 = SO2Me, Z = O, R3 = 3,5-di-Br


1557
R2 = SO2Me, Z = O, R3 = 3,6-di-Br


1558
R2 = SO2Me, Z = O, R3 = 4,5-di-Br


1559
R2 = SO2Me, Z = O, R3 = 3,4-di-CN


1560
R2 = SO2Me, Z = O, R3 = 3,5-di-CN


1561
R2 = SO2Me, Z = O, R3 = 3,6-di-CN


1562
R2 = SO2Me, Z = O, R3 = 4,5-di-CN


1563
R2 = SO2Me, Z = O, R3 = 3,4-di-Me


1564
R2 = SO2Me, Z = O, R3 = 3,5-di-Me


1565
R2 = SO2Me, Z = O, R3 = 3,6-di-Me


1566
R2 = SO2Me, Z = O, R3 = 4,5-di-Me


1567
R2 = SO2Me, Z = O, R3 = 3,4-di-OMe


1568
R2 = SO2Me, Z = O, R3 = 3,5-di-OMe


1569
R2 = SO2Me, Z = O, R3 = 3,6-di-OMe


1570
R2 = SO2Me, Z = O, R3 = 4,5-di-OMe


1571
R2 = SO2Me, Z = O, R3 = 3,4-di-CF3


1572
R2 = SO2Me, Z = O, R3 = 3,5-di-CF3


1573
R2 = SO2Me, Z = O, R3 = 3,6-di-CF3


1574
R2 = SO2Me, Z = O, R3 = 4,5-di-CF3


1575
R2 = SO2Me, Z = O, R3 = 3-CN, 4-Me


1576
R2 = SO2Me, Z = O, R3 = 3-CN, 4-F


1577
R2 = SO2Me, Z = O, R3 = 3-CN, 4-Br


1578
R2 = SO2Me, Z = O, R3 = 3-CN, 4-OMe


1579
R2 = SO2Me, Z = O, R3 = 3-CN, 4-CF3


1580
R2 = SO2Me, Z = O, R3 = 3-CN, 6-Me


1581
R2 = SO2Me, Z = O, R3 = 3-CN, 6-F


1582
R2 = SO2Me, Z = O, R3 = 3-CN, 6-Br


1583
R2 = SO2Me, Z = O, R3 = 3-CN, 6-OMe


1584
R2 = SO2Me, Z = O, R3 = 3-CN, 6-CF3









A compound of this invention will generally be used as a herbicidal active ingredient in a composition, i.e. formulation, with at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, which serves as a carrier. The formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.
Useful formulations include both liquid and solid compositions. Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions, oil-in-water emulsions, flowable concentrates and/or suspoemulsions) and the like, which optionally can be thickened into gels. The general types of aqueous liquid compositions are soluble concentrate, suspension concentrate, capsule suspension, concentrated emulsion, microemulsion, oil-in-water emulsion, flowable concentrate and suspo-emulsion. The general types of nonaqueous liquid compositions are emulsifiable concentrate, microemulsifiable concentrate, dispersible concentrate and oil dispersion.
The general types of solid compositions are dusts, powders, granules, pellets, prills, pastilles, tablets, filled films (including seed coatings) and the like, which can be water-dispersible (“wettable”) or water-soluble. Films and coatings formed from film-forming solutions or flowable suspensions are particularly useful for seed treatment. Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or “overcoated”). Encapsulation can control or delay release of the active ingredient. An emulsifiable granule combines the advantages of both an emulsifiable concentrate formulation and a dry granular formulation. High-strength compositions are primarily used as intermediates for further formulation.
Sprayable formulations are typically extended in a suitable medium before spraying. Such liquid and solid formulations are formulated to be readily diluted in the spray medium, usually water, but occasionally another suitable medium like an aromatic or paraffinic hydrocarbon or vegetable oil. Spray volumes can range from about from about one to several thousand liters per hectare, but more typically are in the range from about ten to several hundred liters per hectare. Sprayable formulations can be tank mixed with water or another suitable medium for foliar treatment by aerial or ground application, or for application to the growing medium of the plant. Liquid and dry formulations can be metered directly into drip irrigation systems or metered into the furrow during planting.
The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.













Weight Percent











Active





Ingredient
Diluent
Surfactant














Water-Dispersible and
0.001-90
   0-99.999
0-15


Water-soluble Granules,


Tablets and Powders


Oil Dispersions, Suspensions,
   1-50
40-99
0-50


Emulsions, Solutions


(including Emulsifiable


Concentrates)


Dusts
   1-25
70-99
0-5 


Granules and Pellets
0.001-99
   5-99.999
0-15


High Strength
  90-99
 0-10
0-2 


Compositions









Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, N.J.
Liquid diluents include, for example, water, N,N-dimethylalkanamides (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), alkyl phosphates (e.g., triethyl phosphate), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffins (e.g., white mineral oils, normal paraffins, isoparaffins), alkylbenzenes, alkylnaphthalenes, glycerine, glycerol triacetate, sorbitol, aromatic hydrocarbons, dearomatized aliphatics, alkylbenzenes, alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, acetates such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetate and isobornyl acetate, other esters such as alkylated lactate esters, dibasic esters, alkyl and aryl benzoates and y-butyrolactone, and alcohols, which can be linear, branched, saturated or unsaturated, such as methanol, ethanol, n-propanol, isopropyl alcohol, n-butanol, isobutyl alcohol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecyl alcohol, isooctadecanol, cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol, cresol and benzyl alcohol. Liquid diluents also include glycerol esters of saturated and unsaturated fatty acids (typically C6-C22), such as plant seed and fruit oils (e.g., oils of olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel), animal-sourced fats (e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil), and mixtures thereof. Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated) wherein the fatty acids may be obtained by hydrolysis of glycerol esters from plant and animal sources, and can be purified by distillation. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.
The solid and liquid compositions of the present invention often include one or more surfactants. When added to a liquid, surfactants (also known as “surface-active agents”) generally modify, most often reduce, the surface tension of the liquid. Depending on the nature of the hydrophilic and lipophilic groups in a surfactant molecule, surfactants can be useful as wetting agents, dispersants, emulsifiers or defoaming agents.
Surfactants can be classified as nonionic, anionic or cationic. Nonionic surfactants useful for the present compositions include, but are not limited to: alcohol alkoxylates such as alcohol alkoxylates based on natural and synthetic alcohols (which may be branched or linear) and prepared from the alcohols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof amine ethoxylates, alkanolamides and ethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylated soybean, castor and rapeseed oils; alkylphenol alkoxylates such as octylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenol ethoxylates and dodecyl phenol ethoxylates (prepared from the phenols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); block polymers prepared from ethylene oxide or propylene oxide and reverse block polymers where the terminal blocks are prepared from propylene oxide; ethoxylated fatty acids; ethoxylated fatty esters and oils; ethoxylated methyl esters; ethoxylated tristyrylphenol (including those prepared from ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); fatty acid esters, glycerol esters, lanolin-based derivatives, polyethoxylate esters such as polyethoxylated sorbitan fatty acid esters, polyethoxylated sorbitol fatty acid esters and polyethoxylated glycerol fatty acid esters; other sorbitan derivatives such as sorbitan esters; polymeric surfactants such as random copolymers, block copolymers, alkyd peg (polyethylene glycol) resins, graft or comb polymers and star polymers; polyethylene glycols (pegs); polyethylene glycol fatty acid esters; silicone-based surfactants; and sugar-derivatives such as sucrose esters, alkyl polyglycosides and alkyl polysaccharides.
Useful anionic surfactants include, but are not limited to: alkylaryl sulfonic acids and their salts; carboxylated alcohol or alkylphenol ethoxylates; diphenyl sulfonate derivatives; lignin and lignin derivatives such as lignosulfonates; maleic or succinic acids or their anhydrides; olefin sulfonates; phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates and phosphate esters of styryl phenol ethoxylates; protein-based surfactants; sarcosine derivatives; styryl phenol ether sulfate; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of ethoxylated alcohols; sulfonates of amines and amides such as N,N-alkyltaurates; sulfonates of benzene, cumene, toluene, xylene, and dodecyl and tridecylbenzenes; sulfonates of condensed naphthalenes; sulfonates of naphthalene and alkyl naphthalene; sulfonates of fractionated petroleum; sulfosuccinamates; and sulfosuccinates and their derivatives such as dialkyl sulfosuccinate salts.
Useful cationic surfactants include, but are not limited to: amides and ethoxylated amides; amines such as N-alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from the amines and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); amine salts such as amine acetates and diamine salts; quaternary ammonium salts such as quaternary salts, ethoxylated quaternary salts and diquaternary salts; and amine oxides such as alkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.
Also useful for the present compositions are mixtures of nonionic and anionic surfactants or mixtures of nonionic and cationic surfactants. Nonionic, anionic and cationic surfactants and their recommended uses are disclosed in a variety of published references including McCutcheon's Emulsifiers and Detergents, annual American and International Editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; and A. S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987.
Compositions of this invention may also contain formulation auxiliaries and additives, known to those skilled in the art as formulation aids (some of which may be considered to also function as solid diluents, liquid diluents or surfactants). Such formulation auxiliaries and additives may control: pH (buffers), foaming during processing (antifoams such polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), in-container microbial growth (antimicrobials), product freezing (antifreezes), color (dyes/pigment dispersions), wash-off (film formers or stickers), evaporation (evaporation retardants), and other formulation attributes. Film formers include, for example, polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes. Examples of formulation auxiliaries and additives include those listed in McCutcheon's Volume 2: Functional Materials, annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03/024222.
The compound of Formula 1 and any other active ingredients are typically incorporated into the present compositions by dissolving the active ingredient in a solvent or by grinding in a liquid or dry diluent. Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is water-immiscible, an emulsifier is typically added to emulsify the active-containing solvent upon dilution with water. Active ingredient slurries, with particle diameters of up to 2,000 μm can be wet milled using media mills to obtain particles with average diameters below 3 μm. Aqueous slurries can be made into finished suspension concentrates (see, for example, U.S. Pat. No. 3,060,084) or further processed by spray drying to form water-dispersible granules. Dry formulations usually require dry milling processes, which produce average particle diameters in the 2 to 10 μm range. Dusts and powders can be prepared by blending and usually grinding (such as with a hammer mill or fluid-energy mill). Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, “Agglomeration”, Chemical Engineering, Dec. 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. Pat. No. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. Pat. No. 4,144,050, U.S. Pat. No. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. Pat. No. 5,180,587, U.S. Pat. No. 5,232,701 and U.S. Pat. No. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. Pat. No. 3,299,566.
For further information regarding the art of formulation, see T. S. Woods, “The Formulator's Toolbox—Product Forms for Modern Agriculture” in Pesticide Chemistry and Bioscience, The Food—Environment Challenge, T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. See also U.S. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989; and Developments in formulation technology, PJB Publications, Richmond, UK, 2000.
In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Table A. Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Percentages are by weight except where otherwise indicated.
Example A










High Strength Concentrate


















Compound 2
98.5%



silica aerogel
0.5%



synthetic amorphous fine silica
1.0%









Example B










Wettable Powder


















Compound 5
65.0%



dodecylphenol polyethylene glycol ether
2.0%



sodium ligninsulfonate
4.0%



sodium silicoaluminate
6.0%



montmorillonite (calcined)
23.0%









Example C










Granule
















Compound 7
10.0%


attapulgite granules (low volatile matter, 0.71/0.30 mm;
90.0%


U.S.S. No. 25-50 sieves)









Example D










Extruded Pellet


















Compound 10
25.0%



anhydrous sodium sulfate
10.0%



crude calcium ligninsulfonate
5.0%



sodium alkylnaphthalenesulfonate
1.0%



calcium/magnesium bentonite
59.0%









Example E










Emulsifiable Concentrate


















Compound 18
10.0%



polyoxyethylene sorbitol hexoleate
20.0%



C6-C10 fatty acid methyl ester
70.0%









Example F










Microemulsion


















Compound 52
5.0%



polyvinylpyrrolidone-vinyl acetate copolymer
30.0%



alkylpolyglycoside
30.0%



glyceryl monooleate
15.0%



water
20.0%









Example G










Suspension Concentrate


















Compound 54
 35%



butyl polyoxyethylene/polypropylene block copolymer
4.0%



stearic acid/polyethylene glycol copolymer
1.0%



styrene acrylic polymer
1.0%



xanthan gum
0.1%



propylene glycol
5.0%



silicone based defoamer
0.1%



1,2-benzisothiazolin-3-one
0.1%



water
53.7% 









Example H










Emulsion in Water


















Compound 58
10.0%



butyl polyoxyethylene/polypropylene block copolymer
4.0%



stearic acid/polyethylene glycol copolymer
1.0%



styrene acrylic polymer
1.0%



xanthan gum
0.1%



propylene glycol
5.0%



silicone based defoamer
0.1%



1,2-benzisothiazolin-3-one
0.1%



aromatic petroleum based hydrocarbon
20.0



water
58.7%









Example I










Oil Dispersion


















Compound 59
25%



polyoxyethylene sorbitol hexaoleate
15% 



organically modified bentonite clay
2.5%



fatty acid methyl ester
57.5%  









Example J










Suspoemulsion


















Compound 2
10.0%



imidacloprid
5.0%



butyl polyoxyethylene/polypropylene block copolymer
4.0%



stearic acid/polyethylene glycol copolymer
1.0%



styrene acrylic polymer
1.0%



xanthan gum
0.1%



propylene glycol
5.0%



silicone based defoamer
0.1%



1,2-benzisothiazolin-3-one
0.1%



aromatic petroleum based hydrocarbon
20.0%



water
53.7%









Test results indicate that the compounds of the present invention are highly active preemergent and/or postemergent herbicides and/or plant growth regulants. The compounds of the invention generally show highest activity for postemergence weed control (i.e. applied after weed seedlings emerge from the soil) and preemergence weed control (i.e. applied before weed seedlings emerge from the soil). Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, air fields, river banks, irrigation and other waterways, around billboards and highway and railroad structures. Many of the compounds of this invention, by virtue of selective metabolism in crops versus weeds, or by selective activity at the locus of physiological inhibition in crops and weeds, or by selective placement on or within the environment of a mixture of crops and weeds, are useful for the selective control of grass and broadleaf weeds within a crop/weed mixture. One skilled in the art will recognize that the preferred combination of these selectivity factors within a compound or group of compounds can readily be determined by performing routine biological and/or biochemical assays. Compounds of this invention may show tolerance to important agronomic crops including, but is not limited to, alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass). Compounds of this invention can be used in crops genetically transformed or bred to incorporate resistance to herbicides, express proteins toxic to invertebrate pests (such as Bacillus thuringiensis toxin), and/or express other useful traits. Those skilled in the art will appreciate that not all compounds are equally effective against all weeds. Alternatively, the subject compounds are useful to modify plant growth.
As the compounds of the invention have both preemergent and postemergent herbicidal activity, to control undesired vegetation by killing or injuring the vegetation or reducing its growth, the compounds can be usefully applied by a variety of methods involving contacting a herbicidally effective amount of a compound of the invention, or a composition comprising said compound and at least one of a surfactant, a solid diluent or a liquid diluent, to the foliage or other part of the undesired vegetation or to the environment of the undesired vegetation such as the soil or water in which the undesired vegetation is growing or which surrounds the seed or other propagule of the undesired vegetation.
A herbicidally effective amount of the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of compounds of this invention is about 0.001 to 20 kg/ha with a preferred range of about 0.004 to 1 kg/ha. One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control.
Compounds of the invention are useful in treating all plants and plant parts. Plant varieties and cultivars can be obtained by conventional propagation and breeding methods or by genetic engineering methods. Genetically modified plants (transgenic plants) are those in which a heterologous gene (transgene) has been stably integrated into the plant's genome. A transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.
Genetically modified plant cultivars which can be treated according to the invention include those that are resistant against one or more biotic stresses (pests such as nematodes, insects, mites, fungi, etc.) or abiotic stresses (drought, cold temperature, soil salinity, etc.), or that contain other desirable characteristics. Plants can be genetically modified to exhibit traits of, for example, herbicide tolerance, insect-resistance, modified oil profiles or drought tolerance. Useful genetically modified plants containing single gene transformation events or combinations of transformation events are listed in Exhibit A. Additional information for the genetic modifications listed in Exhibit A can be obtained from publicly available databases maintained, for example, by the U.S. Department of Agriculture.
The following abbreviations, T1 through T37, are used in Exhibit A for traits. A “-” means the entry is not available.













Trait
Description








T1
Glyphosate tolerance



T2
High lauric acid oil



T3
Glufosinate tolerance



T4
Phytate breakdown



T5
Oxynil tolerance



T6
Disease resistance



T7
Insect resistance



T9
Modified flower color



T11
ALS Herbicide Tol.



T12
Dicamba Tolerance



T13
Anti-allergy



T14
Salt tolerance



T15
Cold tolerance



T16
Imidazolinone herb. tol.



T17
Modified alpha-amylase



T18
Pollination control



T19
2,4-D tolerance



T20
Increased lysine



T21
Drought tolerance



T22
Delayed ripening/senescence



T23
Modified product quality



T24
High cellulose



T25
Modified starch/carbohydrate



T26
Insect & disease resist.



T27
High tryptophan



T28
Erect leaves semidwarf



T29
Semidwarf



T30
Low iron tolerance



T31
Modified oil/fatty acid



T32
HPPD tolerance



T33
High oil



T34
Aryloxyalkanoate tol.



T35
Mesotrione tolerance



T36
Reduced nicotine



T37
Modified product









Exhibit A














Crop
Event Name
Event Code
Trait(s)
Gene(s)







Alfalfa
J101
MON-00101-8
T1
cp4 epsps (aroA:CP4)


Alfalfa
J163
MON-ØØ163-7
T1
cp4 epsps (aroA:CP4)


Canola*
23-18-17 (Event 18)
CGN-89465-2
T2
te


Canola*
23-198 (Event 23)
CGN-89465-2
T2
te


Canola*
61061
DP-Ø61Ø61-7
T1
gat4621


Canola*
73496
DP-Ø73496-4
T1
gat4621


Canola*
GT200 (RT200)
MON-89249-2
T1
cp4 epsps (aroA:CP4); goxv247


Canola*
GT73 (RT73)
MON-ØØØ73-7
T1
cp4 epsps (aroA:CP4); goxv247


Canola*
HCN10 (Topas 19/2)
—
T3
bar


Canola*
HCN28 (T45)
ACS-BNØØ8-2
T3
pat (syn)


Canola*
HCN92 (Topas 19/2)
ACS-BNØØ7-1
T3
bar


Canola*
MON88302
MON-883Ø2-9
T1
cp4 epsps (aroA:CP4)


Canola*
MPS961
—
T4
phyA


Canola*
MPS962
—
T4
phyA


Canola*
MPS963
—
T4
phyA


Canola*
MPS964
—
T4
phyA


Canola*
MPS965
—
T4
phyA


Canola*
MS1 (B91-4)
ACS-BNØØ4-7
T3
bar


Canola*
MS8
ACS-BNØØ5-8
T3
bar


Canola*
OXY-235
ACS-BNØ11-5
T5
bxn


Canola*
PHY14
—
T3
bar


Canola*
PHY23
—
T3
bar


Canola*
PHY35
—
T3
bar


Canola*
PHY36
—
T3
bar


Canola*
RF1 (B93-101)
ACS-BNØØ1-4
T3
bar


Canola*
RF2 (B94-2)
ACS-BNØØ2-5
T3
bar


Canola*
RF3
ACS-BNØØ3-6
T3
bar


Bean
EMBRAPA 5.1
EMB-PV051-1
T6
ac1 (sense and antisense)


Brinjal #
EE-1
—
T7
cry1Ac


Cotton
19-51a
DD-Ø1951A-7
T11
S4-HrA


Cotton
281-24-236
DAS-24236-5
T3, T7
pat (syn); cry1F


Cotton
3006-210-23
DAS-21Ø23-5
T3, T7
pat (syn); cry1Ac


Cotton
31707
—
T5, T7
bxn; cry1Ac


Cotton
31803
—
T5, T7
bxn; cry1Ac


Cotton
31807
—
T5, T7
bxn; cry1Ac


Cotton
31808
—
T5, T7
bxn; cry1Ac


Cotton
42317
—
T5, T7
bxn; cry1Ac


Cotton
BNLA-601
—
T7
cry1Ac


Cotton
BXN10211
BXN10211-9
T5
bxn; cry1Ac


Cotton
BXN10215
BXN10215-4
T5
bxn; cry1Ac


Cotton
BXN10222
BXN10222-2
T5
bxn; cry1Ac


Cotton
BXN10224
BXN10224-4
T5
bxn; cry1Ac


Cotton
COT102
SYN-IR102-7
T7
vip3A(a)


Cotton
COT67B
SYN-IR67B-1
T7
cry1Ab


Cotton
COT202
—
T7
vip3A


Cotton
Event 1
—
T7
cry1Ac


Cotton
GMF Cry1A
GTL-GMF311-7
T7
cry1Ab-Ac


Cotton
GHB119
BCS-GH005-8
T7
cry2Ac


Cotton
GHB614
BCS-GH002-5
T1
2mepsps


Cotton
GK12
—
T7
cry1Ab-Ac


Cotton
LLCotton25
ACS-GH001-3
T3
bar


Cotton
MLS 9124
—
T7
cry1C


Cotton
MON1076
MON-89924-2
T7
cry1Ac


Cotton
MON1445
MON-01445-2
T1
cp4 epsps (aroA:CP4)


Cotton
MON15985
MON-15985-7
T7
cry1Ac; cry2Ab2


Cotton
MON1698
MON-89383-1
T7
cp4 epsps (aroA:CP4)


Cotton
MON531
MON-00531-6
T7
cry1Ac


Cotton
MON757
MON-00757-7
T7
cry1Ac


Cotton
MON88913
MON-88913-8
T1
cp4 epsps (aroA:CP4)


Cotton
Nqwe Chi 6 Bt
—
T7
—


Cotton
SKG321
—
T7
cry1A; CpTI


Cotton
T303-3
BCS-GH003-6
T3, T7
cry1Ab; bar


Cotton
T304-40
BCS-GH004-7
T3, T7
cry1Ab; bar


Cotton
CE43-67B
—
T7
cry1Ab


Cotton
CE46-02A
—
T7
cry1Ab


Cotton
CE44-69D
—
T7
cry1Ab


Cotton
1143-14A
—
T7
cry1Ab


Cotton
1143-51B
—
T7
cry1Ab


Cotton
T342-142
—
T7
cry1Ab


Cotton
PV-GHGT07 (1445)
—
T1
cp4 epsps (aroA:CP4)


Cotton
EE-GH3
—
T1
mepsps


Cotton
EE-GH5
—
T7
cry1Ab


Cotton
MON88701
MON-88701-3
T3, T12
Modified dmo; bar


Cotton
OsCr11
—
T13
Modified Cry j


Flax
FP967
CDC-FL001-2
T11
als


Lentil
RH44
—
T16
als


Maize
3272
SYN-E3272-5
T17
amy797E


Maize
5307
SYN-05307-1
T7
ecry3.1Ab


Maize
59122
DAS-59122-7
T3, T7
cry34Ab1; cry35Ab1; pat


Maize
676
PH-000676-7
T3, T18
pat; dam


Maize
678
PH-000678-9
T3, T18
pat; dam


Maize
680
PH-000680-2
T3, T18
pat; dam


Maize
98140
DP-098140-6
T1, T11
gat4621; zm-hra


Maize
Bt10
—
T3, T7
cry1Ab; pat


Maize
Bt176 (176)
SYN-EV176-9
T3, T7
cry1Ab; bar


Maize
BVLA430101
—
T4
phyA2


Maize
CBH-351
ACS-ZM004-3
T3, T7
cry9C; bar


Maize
DAS40278-9
DAS40278-9
T19
aad-1


Maize
DBT418
DKB-89614-9
T3, T7
cry1Ac; pinII; bar


Maize
DLL25 (B16)
DKB-89790-5
T3
bar


Maize
GA21
MON-00021-9
T1
mepsps


Maize
GG25
—
T1
mepsps


Maize
GJ11
—
T1
mepsps


Maize
Fl117
—
T1
mepsps


Maize
GAT-ZM1
—
T3
pat


Maize
LY038
REN-00038-3
T20
cordapA


Maize
MIR162
SYN-IR162-4
T7
vip3Aa20


Maize
MIR604
SYN-IR604-5
T7
mcry3A


Maize
MON801
MON801
T1, T7
cry1Ab; cp4 epsps (aroA:CP4);



(MON80100)


goxv247


Maize
MON802
MON-80200-7
T1, T7
cry1Ab; cp4 epsps (aroA:CP4);






goxv247


Maize
MON809
PH-MON-809-2
T1, T7
cry1Ab; cp4 epsps (aroA:CP4);






goxv247


Maize
MON810
MON-00810-6
T1, T7
cry1Ab; cp4 epsps (aroA:CP4);






goxv247


Maize
MON832
—
T1
cp4 epsps (aroA:CP4); goxv247


Maize
MON863
MON-00863-5
T7
cry3Bb1


Maize
MON87427
MON-87427-7
T1
cp4 epsps (aroA:CP4)


Maize
MON87460
MON-87460-4
T21
cspB


Maize
MON88017
MON-88017-3
T1, T7
cry3Bb1; cp4 epsps (aroA:CP4)


Maize
MON89034
MON-89034-3
T7
cry2Ab2; cry1A.105


Maize
MS3
ACS-ZM001-9
T3, T18
bar; barnase


Maize
MS6
ACS-ZM005-4
T3, T18
bar; barnase


Maize
NK603
MON-00603-6
T1
cp4 epsps (aroA:CP4)


Maize
T14
ACS-ZM002-1
T3
pat (syn)


Maize
T25
ACS-ZM003-2
T3
pat (syn)


Maize
TC1507
DAS-01507-1
T3, T7
cry1Fa2; pat


Maize
TC6275
DAS-06275-8
T3, T7
mocry1F; bar


Maize
VIP1034
—
T3, T7
vip3A; pat


Maize
43A47
DP-043A47-3
T3, T7
cry1F; cry34Ab1; cry35Ab1; pat


Maize
40416
DP-040416-8
T3, T7
cry1F; cry34Ab1; cry35Ab1; pat


Maize
32316
DP-032316-8
T3, T7
cry1F; cry34Ab1; cry35Ab1; pat


Maize
4114
DP-004114-3
T3, T7
cry1F; cry34Ab1; cry35Ab1; pat


Melon
Melon A
—
T22
sam-k


Melon
Melon B
—
T22
sam-k


Papaya
55-1
CUH-CP551-8
T6
prsv cp


Papaya
63-1
CUH-CP631-7
T6
prsv cp


Papaya
Huanong No. 1
—
T6
prsv rep


Papaya
X17-2
UFL-X17CP-6
T6
prsv cp


Plum
C-5
ARS-PLMC5-6
T6
ppv cp


Canola**
ZSR500
—
T1
cp4 epsps (aroA:CP4); goxv247


Canola**
ZSR502
—
T1
cp4 epsps (aroA:CP4); goxv247


Canola**
ZSR503
—
T1
cp4 epsps (aroA:CP4); goxv247


Rice
7Crp#242-95-7
—
T13
7crp


Rice
7Crp#10
—
T13
7crp


Rice
GM Shanyou 63
—
T7
cry1Ab; cry1Ac


Rice
Huahui-1/TT51-1
—
T7
cry1Ab; cry1Ac


Rice
LLRICE06
ACS-OS001-4
T3
bar


Rice
LLRICE601
BCS-OS003-7
T3
bar


Rice
LLRICE62
ACS-OS002-5
T3
bar


Rice
Tarom molaii +
—
T7
cry1Ab (truncated)



cry1Ab





Rice
GAT-OS2
—
T3
bar


Rice
GAT-OS3
—
T3
bar


Rice
PE-7
—
T7
Cry1Ac


Rice
7Crp#10
—
T13
7crp


Rice
KPD627-8
—
T27
OASA1D


Rice
KPD722-4
—
T27
OASA1D


Rice
KA317
—
T27
OASA1D


Rice
HW5
—
T27
OASA1D


Rice
HW1
—
T27
OASA1D


Rice
B-4-1-18
—
T28
Δ OsBRI1


Rice
G-3-3-22
—
T29
OSGA2ox1


Rice
AD77
—
T6
DEF


Rice
AD51
—
T6
DEF


Rice
AD48
—
T6
DEF


Rice
AD41
—
T6
DEF


Rice
13pNasNaatAprt1
—
T30
HvNAS1; HvNAAT-A; APRT


Rice
13pAprt1
—
T30
APRT


Rice
gHvNAS1-gHvNAAT-1
—
T30
HvNAS1; HvNAAT-A; HvNAAT-B


Rice
gHvIDS3-1
—
T30
HvIDS3


Rice
gHvNAAT1
—
T30
HvNAAT-A; HvNAAT-B


Rice
gHvNAS1-1
—
T30
HvNAS1


Rice
NIA-OS006-4
—
T6
WRKY45


Rice
NIA-OS005-3
—
T6
WRKY45


Rice
NIA-OS004-2
—
T6
WRKY45


Rice
NIA-OS003-1
—
T6
WRKY45


Rice
NIA-OS002-9
—
T6
WRKY45


Rice
NIA-OS001-8
—
T6
WRKY45


Rice
OsCrl1
—
T13
Modified Cry j


Rice
17053
—
T1
cp4 epsps (aroA:CP4)


Rice
17314
—
T1
cp4 epsps (aroA:CP4)


Rose
WKS82/130-4-1
IFD-52401-4
T9
5AT; bp40 (f3′5′h)


Rose
WKS92/130-9-1
IFD-52901-9
T9
5AT; bp40 (f3′5′h)


Soybean
260-05 (G94-1, G94-
—
T9
gm-fad2-1 (silencing locus)



19, G168)





Soybean
A2704-12
ACS-GM005-3
T3
pat


Soybean
A2704-21
ACS-GM004-2
T3
pat


Soybean
A5547-127
ACS-GM006-4
T3
pat


Soybean
A5547-35
ACS-GM008-6
T3
pat


Soybean
CV127
BPS-CV127-9
T16
csr1-2


Soybean
DAS68416-4
DAS68416-4
T3
pat


Soybean
DP305423
DP-305423-1
T11, T31
gm-fad2-1 (silencing locus); gm-hra


Soybean
DP356043
DP-356043-5
T1, T31
gm-fad2-1 (silencing locus); gat4601


Soybean
FG72
MST-FG072-3
T32, T1
2mepsps; hppdPF W336


Soybean
GTS 40-3-2 (40-3-2)
MON-04032-6
T1
cp4 epsps (aroA:CP4)


Soybean
GU262
ACS-GM003-1
T3
pat


Soybean
MON87701
MON-87701-2
T7
cry1Ac


Soybean
MON87705
MON-87705-6
T1, T31
fatb1-A (sense & antisense); fad2-1A






(sense & antisense); cp4 epsps






(aroA:CP4)


Soybean
MON87708
MON-87708-9
T1, T12
dmo; cp4 epsps (aroA:CP4)


Soybean
MON87769
MON-87769-7
T1, T31
Pj.D6D; Nc.Fad3; cp4 epsps






(aroA:CP4)


Soybean
MON89788
MON-89788-1
T1
cp4 epsps (aroA:CP4)


Soybean
W62
ACS-GM002-9
T3
bar


Soybean
W98
ACS-GM001-8
T3
bar


Soybean
MON87754
MON-87754-1
T33
dgat2A


Soybean
DAS21606
DAS-21606
T34, T3
Modified aad-12; pat


Soybean
DAS44406
DAS-44406-6
T1, T3, T34
Modified aad-12; 2mepsps; pat


Soybean
SYHT04R
SYN-0004R-8
T35
Modified avhppd


Soybean
9582.814.19.1
—
T3, T7
cry1Ac, cry1F, PAT


Squash
CZW3
SEM-ØCZW3-2
T6
cmv cp, zymv cp, wmv cp


Squash
ZW20
SEM-0ZW20-7
T6
zymv cp, wmv cp


Sugar Beet
GTSB77 (T9100152)
SY-GTSB77-8
T1
cp4 epsps (aroA:CP4); goxv247


Sugar Beet
H7-1
KM-000H71-4
T1
cp4 epsps (aroA:CP4)


Sugar Beet
T120-7
ACS-BV001-3
T3
pat


Sugar Beet
T227-1
—
T1
cp4 epsps (aroA:CP4)


Sugarcane
NXI-1T
—
T21
EcbetA


Sunflower
X81359
—
T16
als


Pepper
PK-SP01
—
T6
cmv cp


Tobacco
C/F/93/08-02
—
T5
bxn


Tobacco
Vector 21-41
—
T36
NtQPT1 (antisense)


Sunflower
X81359
—
T16
als


Wheat
MON71800
MON-718ØØ-3
T1
cp4 epsps (aroA:CP4)





*Argentine (Brassica napus),


**Polish (B. rapa),


#Eggplant






Treatment of genetically modified plants with compounds of the invention may result in super-additive or synergistic effects. For example, reduction in application rates, broadening of the activity spectrum, increased tolerance to biotic/abiotic stresses or enhanced storage stability may be greater than expected from just simple additive effects of the application of compounds of the invention on genetically modified plants.
Compounds of this invention can also be mixed with one or more other biologically active compounds or agents including herbicides, herbicide safeners, fungicides, insecticides, nematocides, bactericides, acaricides, growth regulators such as insect molting inhibitors and rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other biologically active compounds or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of agricultural protection. Mixtures of the compounds of the invention with other herbicides can broaden the spectrum of activity against additional weed species, and suppress the proliferation of any resistant biotypes. Thus the present invention also pertains to a composition comprising a compound of Formula 1 (in a herbicidally effective amount) and at least one additional biologically active compound or agent (in a biologically effective amount) and can further comprise at least one of a surfactant, a solid diluent or a liquid diluent. The other biologically active compounds or agents can be formulated in compositions comprising at least one of a surfactant, solid or liquid diluent. For mixtures of the present invention, one or more other biologically active compounds or agents can be formulated together with a compound of Formula 1, to form a premix, or one or more other biologically active compounds or agents can be formulated separately from the compound of Formula 1, and the formulations combined together before application (e.g., in a spray tank) or, alternatively, applied in succession.
A mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for weed control: acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron, aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts (e.g., sodium, potassium), aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyrone, bifenox, bilanafos, bispyribac and its sodium salt, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil octanoate, butachlor, butafenacil, butamifos, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone-ethyl, catechin, chlomethoxyfen, chloramben, chlorbromuron, chlorflurenol-methyl, chloridazon, chlorimuron-ethyl, chlorotoluron, chlorpropham, chlorsulfuron, chlorthal-dimethyl, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clefoxydim, clethodim, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-olamine, cloransulam-methyl, cumyluron, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop-butyl, 2,4-D and its butotyl, butyl, isoctyl and isopropyl esters and its dimethylammonium, diolamine and trolamine salts, daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DB and its dimethylammonium, potassium and sodium salts, desmedipham, desmetryn, dicamba and its diglycolammonium, dimethylammonium, potassium and sodium salts, dichlobenil, dichlorprop, diclofop-methyl, diclosulam, difenzoquat metilsulfate, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimethylarsinic acid and its sodium salt, dinitramine, dinoterb, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodium salt, flurenol, flurenol-butyl, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine-ammonium, glufosinate, glufosinate-ammonium, glufosinate-P, glyphosate and its salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate), halauxifen, halauxifen-methyl, halosulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, indaziflam, iofensulfuron, iodosulfuron-methyl, ioxynil, ioxynil octanoate, ioxynil-sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, isoxachlortole, lactofen, lenacil, linuron, maleic hydrazide, MCPA and its salts (e.g., MCPA-dimethylammonium, MCPA-potassium and MCPA-sodium, esters (e.g., MCPA-2-ethylhexyl, MCPA-butotyl) and thioesters (e.g., MCPA-thioethyl), MCPB and its salts (e.g., MCPB-sodium) and esters (e.g., MCPB-ethyl), mecoprop, mecoprop-P, mefenacet, mefluidide, mesosulfuron-methyl, mesotrione, metam-sodium, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methylarsonic acid and its calcium, monoammonium, monosodium and disodium salts, methyldymron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl, molinate, monolinuron, naproanilide, napropamide, napropamide-M, naptalam, neburon, nicosulfuron, norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat dichloride, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, pethoxyamid, phenmedipham, picloram, picloram-potassium, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazoxyfen, pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyridate, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron-methyl, sulfosulfuron, 2,3,6-TBA, TCA, TCA-sodium, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thifensulfuron-methyl, thiobencarb, tiafenacil, tiocarbazil, topramezone, tralkoxydim, tri-allate, triafamone, triasulfuron, triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tridiphane, trietazine, trifloxysulfuron, trifluralin, triflusulfuron-methyl, tritosulfuron, vernolate, 3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthyridin-2(1H)-one, 5-chloro-3-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone, 2-chloro-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)-3-pyridinecarboxamide, 7-(3,5-dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-b]pyrazin-6(5H)-one), 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone), 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole (previously methioxolin), 3-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propyn-1-yl)-2H-1,4-benzoxazin-6-yl]dihydro-1,5-dimethyl-6-thioxo-1,3,5-triazine-2,4(1H,3H)-dione, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione, methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate, 2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide, and 2-methyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide. Other herbicides also include bioherbicides such as Alternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc., Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. and Puccinia thlaspeos Schub.
Compounds of this invention can also be used in combination with plant growth regulators such as aviglycine, N-(phenylmethyl)-1H-purin-6-amine, epocholeone, gibberellic acid, gibberellin A4 and A7, harpin protein, mepiquat chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl, and plant growth modifying organisms such as Bacillus cereus strain BP01.
General references for agricultural protectants (i.e. herbicides, herbicide safeners, insecticides, fungicides, nematocides, acaricides and biological agents) include The Pesticide Manual, 13th Edition, C. D. S. Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, U. K., 2003 and The BioPesticide Manual, 2nd Edition, L. G. Copping, Ed., British Crop Protection Council, Farnham, Surrey, U. K., 2001.
For embodiments where one or more of these various mixing partners are used, the weight ratio of these various mixing partners (in total) to the compound of Formula 1 is typically between about 1:3000 and about 3000:1. Of note are weight ratios between about 1:300 and about 300:1 (for example ratios between about 1:30 and about 30:1). One skilled in the art can easily determine through simple experimentation the biologically effective amounts of active ingredients necessary for the desired spectrum of biological activity. It will be evident that including these additional components may expand the spectrum of weeds controlled beyond the spectrum controlled by the compound of Formula 1 alone.
In certain instances, combinations of a compound of this invention with other biologically active (particularly herbicidal) compounds or agents (i.e. active ingredients) can result in a greater-than-additive (i.e. synergistic) effect on weeds and/or a less-than-additive effect (i.e. safening) on crops or other desirable plants. Reducing the quantity of active ingredients released in the environment while ensuring effective pest control is always desirable. Ability to use greater amounts of active ingredients to provide more effective weed control without excessive crop injury is also desirable. When synergism of herbicidal active ingredients occurs on weeds at application rates giving agronomically satisfactory levels of weed control, such combinations can be advantageous for reducing crop production cost and decreasing environmental load. When safening of herbicidal active ingredients occurs on crops, such combinations can be advantageous for increasing crop protection by reducing weed competition.
Of note is a combination of a compound of the invention with at least one other herbicidal active ingredient. Of particular note is such a combination where the other herbicidal active ingredient has different site of action from the compound of the invention. In certain instances, a combination with at least one other herbicidal active ingredient having a similar spectrum of control but a different site of action will be particularly advantageous for resistance management. Thus, a composition of the present invention can further comprise (in a herbicidally effective amount) at least one additional herbicidal active ingredient having a similar spectrum of control but a different site of action.
Compounds of this invention can also be used in combination with herbicide safeners such as allidochlor, benoxacor, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfonamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone naphthalic anhydride (1,8-naphthalic anhydride), oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide, N-(aminocarbonyl)-2-fluorobenzenesulfonamide, 1-bromo-4-[(chloromethyl)sulfonyl]benzene (BCS), 4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660), 2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), ethyl 1,6-dihydro-1-(2-methoxyphenyl)-6-oxo-2-phenyl-5-pyrimidinecarboxylate, 2-hydroxy-N,N-dimethyl-6-(trifluoromethyl)pyridine-3-carboxamide, and 3-oxo-1-cyclohexen-1-yl 1-(3,4-dimethylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylate to increase safety to certain crops. Antidotally effective amounts of the herbicide safeners can be applied at the same time as the compounds of this invention, or applied as seed treatments. Therefore an aspect of the present invention relates to a herbicidal mixture comprising a compound of this invention and an antidotally effective amount of a herbicide safener. Seed treatment is particularly useful for selective weed control, because it physically restricts antidoting to the crop plants. Therefore a particularly useful embodiment of the present invention is a method for selectively controlling the growth of undesired vegetation in a crop comprising contacting the locus of the crop with a herbicidally effective amount of a compound of this invention wherein seed from which the crop is grown is treated with an antidotally effective amount of safener. Antidotally effective amounts of safeners can be easily determined by one skilled in the art through simple experimentation.
Of note is a composition comprising a compound of the invention (in a herbicidally effective amount), at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners (in an effective amount), and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.
Table A1 lists specific combinations of a Component (a) with Component (b) illustrative of the mixtures, compositions and methods of the present invention. Compound 2 in the Component (a) column is identified in Index Table A. The second column of Table A1 lists the specific Component (b) compound (e.g., “2,4-D” in the first line). The third, fourth and fifth columns of Table A1 lists ranges of weight ratios for rates at which the Component (a) compound is typically applied to a field-grown crop relative to Component (b) (i.e. (a):(b)). Thus, for example, the first line of Table A1 specifically discloses the combination of Component (a) (i.e. Compound 2 in Index Table A) with 2,4-D is typically applied in a weight ratio between 1:192-6:1. The remaining lines of Table A1 are to be construed similarly.











TABLE A1





Component (a)

Typical
More Typical
Most Typical


(Compound #)
Component (b)
Weight Ratio
Weight Ratio
Weight Ratio







2
2,4-D
1:192-6:1
1:64-2:1
1:24-1:3


2
Acetochlor
1:768-2:1
1:256-1:2
1:96-1:11


2
Acifluorfen
1:96-12:1
1:32-4:1
1:12-1:2


2
Aclonifen
1:857-2:1
1:285-1:3
1:107-1:12


2
Alachlor
1:768-2:1
1:256-1:2
1:96-1:11


2
Ametryn
1:384-3:1
1:128-1:1
1:48-1:6


2
Amicarbazone
1:192-6:1
1:64-2:1
1:24-1:3


2
Amidosulfuron
1:6-168:1
1:2-56:1
1:1-11:1


2
Aminocyclopyrachlor
1:48-24:1
1:16-8:1
1:6-2:1


2
Aminopyralid
1:20-56:1
1:6-19:1
1:2-4:1


2
Amitrole
1:768-2:1
1:256-1:2
1:96-1:11


2
Anilofos
1:96-12:1
1:32-4:1
1:12-1:2


2
Asulam
1:960-2:1
1:320-1:3
1:120-1:14


2
Atrazine
1:192-6:1
1:64-2:1
1:24-1:3


2
Azimsulfuron
1:6-168:1
1:2-56:1
1:1-11:1


2
Beflubutamid
1:342-4:1
1:114-2:1
1:42-1:5


2
Benfuresate
1:617-2:1
1:205-1:2
1:77-1:9


2
Bensulfuron-methyl
1:25-45:1
1:8-15:1
1:3-3:1


2
Bentazone
1:192-6:1
1:64-2:1
1:24-1:3


2
Benzobicyclon
1:85-14:1
1:28-5:1
1:10-1:2


2
Benzofenap
1:257-5:1
1:85-2:1
1:32-1:4


2
Bicyclopyrone
1:42-27:1
1:14-9:1
1:5-2:1


2
Bifenox
1:257-5:1
1:85-2:1
1:32-1:4


2
Bispyribac-sodium
1:10-112:1
1:3-38:1
1:1-7:1


2
Bromacil
1:384-3:1
1:128-1:1
1:48-1:6


2
Bromobutide
1:384-3:1
1:128-1:1
1:48-1:6


2
Bromoxynil
1:96-12:1
1:32-4:1
1:12-1:2


2
Butachlor
1:768-2:1
1:256-1:2
1:96-1:11


2
Butafenacil
1:42-27:1
1:14-9:1
1:5-2:1


2
Butylate
1:1542-1:2
1:514-1:5
1:192-1:22


2
Carfenstrole
1:192-6:1
1:64-2:1
1:24-1:3


2
Carfentrazone-ethyl
1:128-9:1
1:42-3:1
1:16-1:2


2
Chlorimuron-ethyl
1:8-135:1
1:2-45:1
1:1-9:1


2
Chlorotoluron
1:768-2:1
1:256-1:2
1:96-1:11


2
Chlorsulfuron
1:6-168:1
1:2-56:1
1:1-11:1


2
Cincosulfuron
1:17-68:1
1:5-23:1
1:2-5:1


2
Cinidon-ethyl
1:384-3:1
1:128-1:1
1:48-1:6


2
Cinmethylin
1:34-34:1
1:11-12:1
1:4-3:1


2
Clacyfos
1:34-34:1
1:11-12:1
1:4-3:1


2
Clethodim
1:48-24:1
1:16-8:1
1:6-2:1


2
Clodinafop-propargyl
1:20-56:1
1:6-19:1
1:2-4:1


2
Clomazone
1:384-3:1
1:128-1:1
1:48-1:6


2
Clomeprop
1:171-7:1
1:57-3:1
1:21-1:3


2
Clopyralid
1:192-6:1
1:64-2:1
1:24-1:3


2
Cloransulam-methyl
1:12-96:1
1:4-32:1
1:1-6:1


2
Cumyluron
1:384-3:1
1:128-1:1
1:48-1:6


2
Cyanazine
1:384-3:1
1:128-1:1
1:48-1:6


2
Cyclopyrimorate
1:17-68:1
1:5-23:1
1:2-5:1


2
Cyclosulfamuron
1:17-68:1
1:5-23:1
1:2-5:1


2
Cycloxydim
1:96-12:1
1:32-4:1
1:12-1:2


2
Cyhalofop
1:25-45:1
1:8-15:1
1:3-3:1


2
Daimuron
1:192-6:1
1:64-2:1
1:24-1:3


2
Desmedipham
1:322-4:1
1:107-2:1
1:40-1:5


2
Dicamba
1:192-6:1
1:64-2:1
1:24-1:3


2
Dichlobenil
1:1371-1:2
1:457-1:4
1:171-1:20


2
Dichlorprop
1:925-2:1
1:308-1:3
1:115-1:13


2
Diclofop-methyl
1:384-3:1
1:128-1:1
1:48-1:6


2
Diclosulam
1:10-112:1
1:3-38:1
1:1-7:1


2
Difenzoquat
1:288-4:1
1:96-2:1
1:36-1:4


2
Diflufenican
1:857-2:1
1:285-1:3
1:107-1:12


2
Diflufenzopyr
1:12-96:1
1:4-32:1
1:1-6:1


2
Dimethachlor
1:768-2:1
1:256-1:2
1:96-1:11


2
Dimethametryn
1:192-6:1
1:64-2:1
1:24-1:3


2
Dimethenamid-P
1:384-3:1
1:128-1:1
1:48-1:6


2
Dithiopyr
1:192-6:1
1:64-2:1
1:24-1:3


2
Diuron
1:384-3:1
1:128-1:1
1:48-1:6


2
EPTC
1:768-2:1
1:256-1:2
1:96-1:11


2
Esprocarb
1:1371-1:2
1:457-1:4
1:171-1:20


2
Ethalfluralin
1:384-3:1
1:128-1:1
1:48-1:6


2
Ethametsulfuron-methyl
1:17-68:1
1:5-23:1
1:2-5:1


2
Ethoxyfen
1:8-135:1
1:2-45:1
1:1-9:1


2
Ethoxysulfuron
1:20-56:1
1:6-19:1
1:2-4:1


2
Etobenzanid
1:257-5:1
1:85-2:1
1:32-1:4


2
Fenoxaprop-ethyl
1:120-10:1
1:40-4:1
1:15-1:2


2
Fenoxasulfone
1:85-14:1
1:28-5:1
1:10-1:2


2
Fenquinotrione
1:17-68:1
1:5-23:1
1:2-5:1


2
Fentrazamide
1:17-68:1
1:5-23:1
1:2-5:1


2
Flazasulfuron
1:17-68:1
1:5-23:1
1:2-5:1


2
Florasulam
1:2-420:1
1:1-140:1
2:1-27:1


2
Fluazifop-butyl
1:192-6:1
1:64-2:1
1:24-1:3


2
Flucarbazone
1:8-135:1
1:2-45:1
1:1-9:1


2
Flucetosulfuron
1:8-135:1
1:2-45:1
1:1-9:1


2
Flufenacet
1:257-5:1
1:85-2:1
1:32-1:4


2
Flumetsulam
1:24-48:1
1:8-16:1
1:3-3:1


2
Flumiclorac-pentyl
1:10-112:1
1:3-38:1
1:1-7:1


2
Flumioxazin
1:25-45:1
1:8-15:1
1:3-3:1


2
Fluometuron
1:384-3:1
1:128-1:1
1:48-1:6


2
Flupyrsulfuron-methyl
1:3-336:1
1:1-112:1
2:1-21:1


2
Fluridone
1:384-3:1
1:128-1:1
1:48-1:6


2
Fluroxypyr
1:96-12:1
1:32-4:1
1:12-1:2


2
Flurtamone
1:857-2:1
1:285-1:3
1:107-1:12


2
Fluthiacet-methyl
1:48-42:1
1:16-14:1
1:3-3:1


2
Fomesafen
1:96-12:1
1:32-4:1
1:12-1:2


2
Foramsulfuron
1:13-84:1
1:4-28:1
1:1-6:1


2
Glufosinate
1:288-4:1
1:96-2:1
1:36-1:4


2
Glyphosate
1:288-4:1
1:96-2:1
1:36-1:4


2
Halauxifen
1:20-56:1
1:6-19:1
1:2-4:1


2
Halauxifen-methyl
1:20-56:1
1:6-19:1
1:2-4:1


2
Halosulfuron-methyl
1:17-68:1
1:5-23:1
1:2-5:1


2
Haloxyfop-methyl
1:34-34:1
1:11-12:1
1:4-3:1


2
Hexazinone
1:192-6:1
1:64-2:1
1:24-1:3


2
Imazamox
1:13-84:1
1:4-28:1
1:1-6:1


2
Imazapic
1:20-56:1
1:6-19:1
1:2-4:1


2
Imazapyr
1:85-14:1
1:28-5:1
1:10-1:2


2
Imazaquin
1:34-34:1
1:11-12:1
1:4-3:1


2
Imazethabenz-methyl
1:171-7:1
1:57-3:1
1:21-1:3


2
Imazethapyr
1:24-48:1
1:8-16:1
1:3-3:1


2
Imazosulfuron
1:27-42:1
1:9-14:1
1:3-3:1


2
Indanofan
1:342-4:1
1:114-2:1
1:42-1:5


2
Indaziflam
1:25-45:1
1:8-15:1
1:3-3:1


2
Iodosulfuron-methyl
1:3-336:1
1:1-112:1
2:1-21:1


2
Ioxynil
1:192-6:1
1:64-2:1
1:24-1:3


2
Ipfencarbazone
1:85-14:1
1:28-5:1
1:10-1:2


2
Isoproturon
1:384-3:1
1:128-1:1
1:48-1:6


2
Isoxaben
1:288-4:1
1:96-2:1
1:36-1:4


2
Isoxaflutole
1:60-20:1
1:20-7:1
1:7-2:1


2
Lactofen
1:42-27:1
1:14-9:1
1:5-2:1


2
Lenacil
1:384-3:1
1:128-1:1
1:48-1:6


2
Linuron
1:384-3:1
1:128-1:1
1:48-1:6


2
MCPA
1:192-6:1
1:64-2:1
1:24-1:3


2
MCPB
1:288-4:1
1:96-2:1
1:36-1:4


2
Mecoprop
1:768-2:1
1:256-1:2
1:96-1:11


2
Mefenacet
1:384-3:1
1:128-1:1
1:48-1:6


2
Mefluidide
1:192-6:1
1:64-2:1
1:24-1:3


2
Mesosulfuron-methyl
1:5-224:1
1:1-75:1
1:1-14:1


2
Mesotrione
1:42-27:1
1:14-9:1
1:5-2:1


2
Metamifop
1:42-27:1
1:14-9:1
1:5-2:1


2
Metazachlor
1:384-3:1
1:128-1:1
1:48-1:6


2
Metazosulfuron
1:25-45:1
1:8-15:1
1:3-3:1


2
Methabenzthiazuron
1:768-2:1
1:256-1:2
1:96-1:11


2
Metolachlor
1:768-2:1
1:256-1:2
1:96-1:11


2
Metosulam
1:8-135:1
1:2-45:1
1:1-9:1


2
Metribuzin
1:192-6:1
1:64-2:1
1:24-1:3


2
Metsulfuron-methyl
1:2-560:1
1:1-187:1
3:1-35:1


2
Molinate
1:1028-2:1
1:342-1:3
1:128-1:15


2
Napropamide
1:384-3:1
1:128-1:1
1:48-1:6


2
Napropamide-M
1:192-6:1
1:64-2:1
1:24-1:3


2
Naptalam
1:192-6:1
1:64-2:1
1:24-1:3


2
Nicosulfuron
1:12-96:1
1:4-32:1
1:1-6:1


2
Norflurazon
1:1152-1:1
1:384-1:3
1:144-1:16


2
Orbencarb
1:1371-1:2
1:457-1:4
1:171-1:20


2
Orthosulfamuron
1:20-56:1
1:6-19:1
1:2-4:1


2
Oryzalin
1:514-3:1
1:171-1:2
1:64-1:8


2
Oxadiargyl
1:384-3:1
1:128-1:1
1:48-1:6


2
Oxadiazon
1:548-3:1
1:182-1:2
1:68-1:8


2
Oxasulfuron
1:27-42:1
1:9-14:1
1:3-3:1


2
Oxaziclomefone
1:42-27:1
1:14-9:1
1:5-2:1


2
Oxyfluorfen
1:384-3:1
1:128-1:1
1:48-1:6


2
Paraquat
1:192-6:1
1:64-2:1
1:24-1:3


2
Pendimethalin
1:384-3:1
1:128-1:1
1:48-1:6


2
Penoxsulam
1:10-112:1
1:3-38:1
1:1-7:1


2
Penthoxamid
1:384-3:1
1:128-1:1
1:48-1:6


2
Pentoxazone
1:102-12:1
1:34-4:1
1:12-1:2


2
Phenmedipham
1:102-12:1
1:34-4:1
1:12-1:2


2
Picloram
1:96-12:1
1:32-4:1
1:12-1:2


2
Picolinafen
1:34-34:1
1:11-12:1
1:4-3:1


2
Pinoxaden
1:25-45:1
1:8-15:1
1:3-3:1


2
Pretilachlor
1:192-6:1
1:64-2:1
1:24-1:3


2
Primisulfuron-methyl
1:8-135:1
1:2-45:1
1:1-9:1


2
Prodiamine
1:384-3:1
1:128-1:1
1:48-1:6


2
Profoxydim
1:42-27:1
1:14-9:1
1:5-2:1


2
Prometryn
1:384-3:1
1:128-1:1
1:48-1:6


2
Propachlor
1:1152-1:1
1:384-1:3
1:144-1:16


2
Propanil
1:384-3:1
1:128-1:1
1:48-1:6


2
Propaquizafop
1:48-24:1
1:16-8:1
1:6-2:1


2
Propoxycarbazone
1:17-68:1
1:5-23:1
1:2-5:1


2
Propyrisulfuron
1:17-68:1
1:5-23:1
1:2-5:1


2
Propyzamide
1:384-3:1
1:128-1:1
1:48-1:6


2
Prosulfocarb
1:1200-1:2
1:400-1:4
1:150-1:17


2
Prosulfuron
1:6-168:1
1:2-56:1
1:1-11:1


2
Pyraclonil
1:42-27:1
1:14-9:1
1:5-2:1


2
Pyraflufen-ethyl
1:5-224:1
1:1-75:1
1:1-14:1


2
Pyrasulfotole
1:13-84:1
1:4-28:1
1:1-6:1


2
Pyrazolynate
1:857-2:1
1:285-1:3
1:107-1:12


2
Pyrazosulfuron-ethyl
1:10-112:1
1:3-38:1
1:1-7:1


2
Pyrazoxyfen
1:5-224:1
1:1-75:1
1:1-14:1


2
Pyribenzoxim
1:10-112:1
1:3-38:1
1:1-7:1


2
Pyributicarb
1:384-3:1
1:128-1:1
1:48-1:6


2
Pyridate
1:288-4:1
1:96-2:1
1:36-1:4


2
Pyriftalid
1:10-112:1
1:3-38:1
1:1-7:1


2
Pyriminobac-methyl
1:20-56:1
1:6-19:1
1:2-4:1


2
Pyrimisulfan
1:17-68:1
1:5-23:1
1:2-5:1


2
Pyrithiobac
1:24-48:1
1:8-16:1
1:3-3:1


2
Pyroxasulfone
1:85-14:1
1:28-5:1
1:10-1:2


2
Pyroxsulam
1:5-224:1
1:1-75:1
1:1-14:1


2
Quinclorac
1:192-6:1
1:64-2:1
1:24-1:3


2
Quizalofop-ethyl
1:42-27:1
1:14-9:1
1:5-2:1


2
Rimsulfuron
1:13-84:1
1:4-28:1
1:1-6:1


2
Saflufenacil
1:25-45:1
1:8-15:1
1:3-3:1


2
Sethoxydim
1:96-12:1
1:32-4:1
1:12-1:2


2
Simazine
1:384-3:1
1:128-1:1
1:48-1:6


2
Sulcotrione
1:120-10:1
1:40-4:1
1:15-1:2


2
Sulfentrazone
1:147-8:1
1:49-3:1
1:18-1:3


2
Sulfometuron-methyl
1:34-34:1
1:11-12:1
1:4-3:1


2
Sulfosulfuron
1:8-135:1
1:2-45:1
1:1-9:1


2
Tebuthiuron
1:384-3:1
1:128-1:1
1:48-1:6


2
Tefuryltrione
1:42-27:1
1:14-9:1
1:5-2:1


2
Tembotrione
1:31-37:1
1:10-13:1
1:3-3:1


2
Tepraloxydim
1:25-45:1
1:8-15:1
1:3-3:1


2
Terbacil
1:288-4:1
1:96-2:1
1:36-1:4


2
Terbuthylazine
1:857-2:1
1:285-1:3
1:107-1:12


2
Terbutryn
1:192-6:1
1:64-2:1
1:24-1:3


2
Thenylchlor
1:85-14:1
1:28-5:1
1:10-1:2


2
Thiazopyr
1:384-3:1
1:128-1:1
1:48-1:6


2
Thiencarbazone
1:3-336:1
1:1-112:1
2:1-21:1


2
Thifensulfuron-methyl
1:5-224:1
1:1-75:1
1:1-14:1


2
Tiafenacil
1:17-68:1
1:5-23:1
1:2-5:1


2
Thiobencarb
1:768-2:1
1:256-1:2
1:96-1:11


2
Topramezone
1:6-168:1
1:2-56:1
1:1-11:1


2
Tralkoxydim
1:68-17:1
1:22-6:1
1:8-2:1


2
Triallate
1:768-2:1
1:256-1:2
1:96-1:11


2
Triasulfuron
1:5-224:1
1:1-75:1
1:1-14:1


2
Triaziflam
1:171-7:1
1:57-3:1
1:21-1:3


2
Tribenuron-methyl
1:3-336:1
1:1-112:1
2:1-21:1


2
Triclopyr
1:192-6:1
1:64-2:1
1:24-1:3


2
Trifloxysulfuron
1:2-420:1
1:1-140:1
2:1-27:1


2
Trifluralin
1:288-4:1
1:96-2:1
1:36-1:4


2
Triflusulfuron-methyl
1:17-68:1
1:5-23:1
1:2-5:1


2
Tritosulfuron
1:13-84:1
1:4-28:1
1:1-6:1









Table A2 is constructed the same as Table A1 above except that entries below the “Component (a)” column heading are replaced with the respective Component (a) Column Entry shown below. Compound 2 in the Component (a) column is identified in Index Table A. Thus, for example, in Table A2 the entries below the “Component (a)” column heading all recite “Compound 7” (i.e. Compound 5 identified in Index Table A), and the first line below the column headings in Table A2 specifically discloses a mixture of Compound 5 with 2,4-D. Tables A3 through A20 are constructed similarly.













Table Number
Component (a) Column Entries








A2
Compound 5



A3
Compound 7



A4
Compound 10



A5
Compound 18



A6
Compound 52



A7
Compound 54



A8
Compound 58



A9
Compound 59



A10
Compound 141



A11
Compound 166



A12
Compound 147



A13
Compound 79



A14
Compound 178



A15
Compound 274



A16
Compound 138



A17
Compound 194



A18
Compound 253



A19
Compound 252



A20
Compound 305









Preferred for better control of undesired vegetation (e.g., lower use rate such as from synergism, broader spectrum of weeds controlled, or enhanced crop safety) or for preventing the development of resistant weeds are mixtures of a compound of this invention with a herbicide selected from the group consisting of aminocyclopyrachlor, diuron, hexazinone, nicosulfuron, chlorimuron-ethyl, metsulfuron-methyl, thifensulfuron-methyl and tribenuron.
The following Tests demonstrate the control efficacy of the compounds of this invention against specific weeds. The weed control afforded by the compounds is not limited, however, to these species. See Index Tables A for compound descriptions. The following abbreviations are used in the Index Table A which follow: c is cyclo, Me is methyl, Et is ethyl, Pr is propyl, i-Pr is isopropyl, t-Bu is tert-butyl, —CN is cyano, —NO2 is nitro. The abbreviation “Ex.” stands for “Example” and is followed by a number indicating in which example the compound is prepared.
Representative compounds of this invention prepared by the methods described herein are shown in Index Table A. See Index Table B for 1H NMR data. For mass spectral data (AP+(M+1)), the numerical value reported is the molecular weight of the parent molecular ion (M) formed by addition of H+(molecular weight of 1) to the molecule to give a M+1 peak observed by mass spectrometry using atmospheric pressure chemical ionization (AP+). The alternate molecular ion peaks (e.g., M+2 or M+4) that occur with compounds containing multiple halogens are not reported. The reported M+1 peaks were observed by mass spectrometry using atmospheric pressure chemical ionization (AP+) or electrospray ionization (ESI).







INDEX TABLE A







1








 















Cmpd







mp or


No.
Y1 
Y2
Y3 
Y4
Z
R2
(R3)m
MS


















1
N
CCF3
CH
CH
O
Br
H (m is 0)
*


2
N
CCF3
CH
CH
O
Cl
H (m is 0)
*


3
N
CH
CCl
CH
O
Cl
H (m is 0)
*


4
N
CCF3
CH
CH
O
CF3
H (m is 0)
*


5
N
CH
CCl
CH
O
Br
H (m is 0)
*


6
N
CH
CCl
CH
O
CF3
H (m is 0)
*


7
N
CH
CBr
CH
O
Cl
H (m is 0)
*


8
N
CH
CBr
CH
O
Br
H (m is 0)
*


9
N
CH
CBr
CH
O
CH3
H (m is 0)
*


10
N
CH
CBr
CH
O
F
H (m is 0)
*


11
N
CH
CCl
CH
O
F
H (m is 0)
*


12
N
CH
CH
CH
O
Cl
H (m is 0)
*


13
N
CH
CH
CH
O
Br
H (m is 0)
*


14
N
CH
CH
CH
O
F
H (m is 0)
*


15
N
CH
CCl
CH
O
CH3
H (m is 0)
*


16
N
CH
CCF3
CH
O
Cl
H (m is 0)
*


17
N
CH
CCF3
CH
O
CF3
H (m is 0)
*


18
N
CH
CCF3
CH
O
Br
H (m is 0)
*


19
N
CBr
CBr
CH
O
Cl
H (m is 0)
*


20
N
CBr
CH
CH
O
Br
H (m is 0)
*


21
N
CBr
CH
CH
O
Cl
H (m is 0)
*


22
N
CH
CPh
CH
O
Cl
H (m is 0)
*


23
N
CH
CCH3
CH
O
Cl
H (m is 0)
*


24
N
CBr
CBr
CH
O
Br
H (m is 0)
*


25
N
CH
Cl
CH
O
Cl
H (m is 0)
*


26
N
CH
Cl
CH
O
C
H (m is 0)
*


27
N
CH
CCH═CHCH3
CH
O
Cl
H (m is 0)
*


28
N
CCF3
CH
CH
S
Cl
H (m is 0)
357


29
N
C(t-Bu)
CH
CH
O
Cl
H (m is 0)
*


30
N
C(t-Bu)
CH
CH
O
Br
H (m is 0)
*


31
N
CH
CCH═CH2
CH
O
Cl
H (m is 0)
*


32
N
CH
C(CH3)═CH2
CH
O
Cl
H (m is 0)
*


33
N
CH
CCN
CH
O
Cl
H (m is 0)
*


34
CH
N
CBr
CH
O
Cl
H (m is 0)
*


35
N
CH
CBr
CH
O
Cl
5-OCH3
323


36
N
CCH3
CH
CH
O
Cl
H (m is 0)
*


37
N
CCH3
CBr
CH
O
Cl
H (m is 0)
*


38
N
CCH3
Cl
CH
O
Cl
H (m is 0)
*


39
N
CCH3
CCl
CH
O
Cl
H (m is 0)
*


40
N
CH
CBr
CH
O
Cl
4-CH3
366


41
N
CH
CBr
CH
O
Cl
6-OCH3
382


42
N
CH
CBr
CH
O
Cl
4-OCH3
382


43
N
CH
CBr
CH
O
Br
4-OCH3
425


44
N
CH
CBr
CH
O
Cl
3-CH3
366


45
N
CH
CBr
CH
O
Br
3-CH3
411


46
N
CBr
N
CH
O
Cl
H (m is 0)
*


47
N
CH
CCF3
CH
O
F
H (m is 0)
*


48
N
CH
CBr
CH
O
Cl
4-CF3
420


49
N
CH
CH
CH
O
Cl
5-Cl
*


50
N
CH
CH
CH
O
Br
5-Cl
*


51
N
CH
CBr
CH
O
Cl
5-Cl
*


52
N
CH
CBr
CH
O
Cl
3-CN
376


53
N
CH
CBr
CH
O
Cl
4-F
124-127


54
N
CBr
CH
N
O
Cl
H (m is 0)
352


55
N
CCN
CH
N
O
Cl
H (m is 0)
299


56
N
CCN
CH
N
O
Br
H (m is 0)
*


57
N
CH
CBr
CH
O
Br
3-CN
422


58
N
CH
CCF3
CH
O
Cl
3-CN
*


59
N
CH
CCF3
CH
O
Br
3-CN
*


60
N
CH
CBr
CH
O
I
3-CN
470


61
N
CH
CBr
CH
O
Cl
3-CHO
379


62
N
CH
CBr
CH
O
F
3-CN
362


63
N
CH
CBr
CH
O
Cl
3-NO2
398


64
N
CH
CBr
CH
O
Cl
3-CF3
420


65
N
CH
CBr
CH
O
Cl
3-Br
*


66
N
CH
CBr
CH
O
Cl
3-I
*


67
N
CH
CBr
CH
O
Cl
3-O(C═O)CH3
*


68
N
CH
CBr
CH
O
Cl
3-OH
*


69
N
CH
CBr
CH
O
Cl
3-OCH2CF3
*


70
N
CH
CBr
CH
O
Cl
3-OCH2CN
406


71
N
CH
CCl
CH
O
Br
3-CN
378


72
N
CH
CCl
CH
O
Cl
3-CN
332


73
N
CH
CCl
CH
O
F
3-CN
316


74
CH
CBr
N
CH
O
Cl
3-CN
*


75
N
CH
CCl
CH
O
I
3-CN
424


76
N
CH
CBr
CH
O
CH3
3-CN
358


77
N
CH
CBr
CH
O
Br
3-CF3
465


78
N
CH
CBr
CH
O
Cl
3-OCF3
436


79
N
CH
CCF3
CH
O
F
3-CN
*


80
N
CH
CF2H
CH
O
Cl
H (m is 0)
*


81
N
CH
CF2H
CH
O
Br
H (m is 0)
*


82
N
CH
C(t-Bu)
CH
O
Cl
3-CN
354


83
N
CH
CBr
CH
O
Cl
3-CH2F
384


84
N
N
COEt
CH
O
Cl
3-Br
398


85
N
CH
C(i-Pr)
CH
O
Cl
3-CN
340


86
N
CH
Cl
CH
O
F
3-CN
408


87
N
CH
Cl
CH
O
I
3-CN
516


88
N
CH
Cl
CH
O
Br
3-CN
470


89
N
CH
COEt
CH
O
F
3-CN
*


90
N
CH
CCN
CH
O
CH3
3-CN
303


91
N
CH
CCN
CH
O
I
3-CN
415


92
N
CH
COEt
CH
O
Cl
3-CN
342


93
N
CH
CCl
CH
O
F
3-CHO
319


94
N
CH
CCl
CH
O
F
3-CHF2
341


95
N
CH
CCH3
CH
O
Cl
3-CN
311


96
N
CH
CBr
CH
O
Cl
3-C(═O)CH3
395


97
N
CH
COCHF2
CH
O
Cl
3-CN
364


98
N
CH
COCHF2
CH
O
Cl
H (m is 0)
339


99
N
CH
COCH2CHF2
CH
O
Cl
3-CN
*


100
CH
N
CH
CH
O
Cl
H (m is 0)
273


101
N
CH
COCHF2
CH
O
F
3-Cl
*


102
N
N
C(cyclohexyl)
CH
O
Cl
3-F
374


103
N
CH
CO(i-Pr)
CH
O
Cl
3-Cl
*


104
N
CH
CCF3
CH
O
Cl
3-I
467


105
N
CH
CCHF2
CH
O
Cl
3-I
*


106
N
N
C(cyclopentyl)
CH
O
Cl
3-F
360


107
N
N
CCH2CH(Me)2
CH
O
Cl
3-F
348


108
N
N
CCH2CH2F
CH
O
Cl
3-F
338


109
N
CH
COCH2CF3
CH
O
F
3-Cl
389


110
N
CH
COCH2CF3
CH
O
Cl
3-Cl
*


111
N
CH
CCN
CH
O
F
3-CN
*


112
N
CH
CBr
CH
O
F
3-CHF2
386


113
N
CH
CBr
CH
O
CF3
3-CN
410


114
N
N
CC(═CH2)CH3
CH
O
Cl
3-Br
394


115
N
N
CC(═NOH)CH3
CH
O
Cl
3-Br
411


116
N
N
CCN
CH
O
Cl
3-Br
377


117
N
N
CI
CH
O
Cl
3-Br
480


118
N
CH
CCF3
CH
O
F
3-CH2F
357


119
N
CH
CCF3
CH
O
Cl
3-CH2F
373


120
N
CH
CCF3
CH
O
Br
3-CH2F
418


121
N
CH
COMe
CH
O
Cl
3-F
321


122
N
CH
COCHF2
CH
O
Cl
3-Br
418


123
N
N
CCH2F
CH
O
Cl
H (m is 0)
306


124
CH
CH
CCHO
CH
O
Cl
H (m is 0)
*


125
N
CH
CBr
CH
O
Br
3-CH2F
429


126
N
CH
COCH2CF3
CH
O
F
3-F
*


127
N
CH
CO(n-Pr)
CH
O
Cl
3-F
349


128
N
CH
COCH2CF3
CH
O
Cl
3-Br
450


129
N
N
CBr
CH
O
Cl
3-Br
432


130
N
CH
CBr
CH
O
i-Pr
3-CN
386


131
N
CH
CBr
CH
O
n-Pr
3-CN
384


132
N
CH
CSCF3
CH
O
Cl
H (m is 0)
*


133
N
CH
CSCF3
CH
O
Cl
3-I
*


134
N
CH
CSCF3
CH
O
Cl
3-CN
*


135
N
CH
CCN
CH
O
Br
3-CN
369


136
N
CH
CI
CH
O
CH3
3-CN
404


137
N
CH
COMe
CH
O
Cl
3-CN
328


138
N
CH
COCH2CF3
CH
O
Cl
H (m is 0)
371


139
N
N
CCHO
CH
O
Cl
3-F
320


140
N
CH
CCN
CH
O
Cl
3-Br
378


141
N
N
CCHF2
CH
O
Cl
3-F
342


142
N
CH
CBr
CH
O
Cl
3-SO2CH3
429


143
N
CH
CS(O)CF3
CH
O
Cl
H (m is 0)
*


144
N
CH
CCN
CH
O
Cl
3-Cl
332


145
N
CH
CBr
CH
O
F
3-CHF2
368


146
N
CH
CBr
CH
O
Cl
3-CHF(CH3)
398


147
N
N
CCHF2
CH
O
Cl
H (m is 0)
324


148
N
CH
CO(i-Pr)
CH
O
Cl
3-Br
*


149
N
CH
CO(i-Pr)
CH
O
Cl
3-CN
356


150
N
CH
CO(n-Pr)
CH
O
Cl
3-CN
356


151
N
CH
CCN
CH
O
F
3-CH2F
314


152
N
CH
CI
CH
O
F
3-CH2F
415


153
N
CH
CO(n-Pr)
CH
O
F
3-F
333


154
N
N
CCH2F
CH
O
Cl
3-F
324


155
N
N
C(c-Pr)
CH
O
Cl
3-F
332


156
N
CH
CO(i-Pr)
CH
O
F
3-Br
*


157
N
CH
COCH2CF3
CH
O
F
3-Br
*


158
N
CH
CO(i-Pr)
CH
O
F
3-CN
340


159
N
N
CH
CH
O
Cl
3-F
292


160
N
N
C(c-Pr)
CH
O
Cl
H (m is 0)
314


161
N
CH
CCF3
CH
O
Br
3-CHO
414


162
N
CH
CCF3
CH
O
F
3-CHO
353


163
N
CH
CCF3
CH
O
Br
3-CHF2
436


164
N
CH
CCF3
CH
O
F
3-CHF2
375


165
N
CH
CH
CH
O
Br
3-CN
342


166
N
N
CCF3
CH
O
Cl
H (m is 0)
342


167
N
CH
CCF3
CH
O
Cl
3-Cl
375


168
N
CH
CCF3
CH
O
Br
3-Cl
421


169
N
CH
CCl
CH
O
Cl
3-OMe
337


170
N
CH
CCF3
CH
O
Cl
3-CHF2
391


171
N
CH
CCF3
CH
O
Cl
3-CHO
369


172
N
CH
CBr
CH
O
I
3-CHO
472


173
N
CH
CBr
CH
O
I
3-CHF2
494


174
N
CH
CBr
CH
O
CN
3-CHO
371


175
N
CH
CBr
CH
O
CN
3-CHF2
393


176
N
CH
CH
CH
O
Cl
3-F
291


177
N
CH
CCl
CH
O
Cl
3-F
325


178
N
CH
CBr
CH
O
Cl
3-F
369


179
N
CH
CI
CH
O
Cl
3-F
417


180
N
CH
CCF3
CH
O
CH3
3-CN
*


181
N
CH
CI
CH
O
Cl
3-Cl
435


182
N
CH
CI
CH
O
Cl
3-CHO
425


183
N
CH
CI
CH
O
Br
3-CHO
472


184
N
CH
CI
CH
O
Cl
3-CHF2
449


185
N
CH
CI
CH
O
Br
3-CHF2
494


186
N
CH
COMe
CH
O
Cl
H (m is 0)
*


187
N
CH
COEt
CH
O
Cl
H (m is 0)
317


188
N
CH
CC≡CH
CH
O
Cl
H (m is 0)
297


189
N
CH
CC≡CMe
CH
O
Cl
H (m is 0)
311


190
N
CH
C(2-pyridinyl)
CH
O
Cl
H (m is 0)
350


191
N
CH
CCF3
CH
O
Cl
3-Br
419


192
N
CH
CCHF2
CH
O
Cl
3-Cl
358


193
N
CH
N
CH
O
Cl
3-CN
299


194
N
CH
CBr
CH
O
Cl
3-CHF2
402


195
N
CH
CBr
CH
O
Cl
3-Ph
428


196
N
CH
CBr
CH
O
Cl
4,5-diF
389


197
N
CH
CBr
CH
O
Cl
3-CH═CH2
392


198
N
CH
CBr
CH
O
Cl
3-C(Me)═CH2
392


199
N
CH
CBr
CH
O
Cl
3-C≡CH
377


200
N
CH
CCN
CH
O
Cl
3-CN
323


201
N
CH
CBr
CH
O
Cl
3-Br, 6-OMe
461


202
N
CH
CBr
CH
O
Cl
3-Br, 4-Me
445


203
N
CH
CBr
CH
O
Cl
3-CH═NOMe
*


204
N
CH
CI
CH
O
Cl
3-CN
424


205
N
CH
CCl
CH
O
Cl
3-CHO
334


206
N
CH
CCl
CH
O
Br
3-CHO
380


207
N
CH
CBr
CH
O
Cl
3-I, 6-OMe
508


208
N
CH
CH
CH
O
Cl
3-CN
298


209
N
CH
CCl
CH
O
Cl
3-CHF2
358


210
N
CH
CCl
CH
O
Br
3-CHF2
402


211
N
CH
CBr
CH
O
Cl
3-CO2Me
411


212
N
CH
CBr
CH
O
Cl
3-CN, 6-OMe
407


213
N
CH
CBr
CH
O
Cl
4-CN
*


214
N
CH
CBr
CH
O
CN
3-CN
369


215
N
CH
CBr
CH
O
C≡CH
3-CN
368


216
N
CH
CCl
CH
O
Cl
3-OC(═O)Me
365


217
N
N
CH
CH
O
Cl
H (m is 0)
274


218
N
CH
CBr
CH
O
OMe
3-CN
372


219
N
CH
CBr
CH
O
Cl
3-Cl
387


220
N
CH
CCl
CH
O
Cl
3-Cl
341


221
N
CH
CCl
CH
O
Cl
3-Br
387


222
N
N
CI
CH
O
Cl
H (m is 0)
400


223
N
N
CBr
CH
O
Cl
H (m is 0)
354


224
N
N
CCl
CH
O
Cl
H (m is 0)
308


225
N
CH
CBr
CH
O
NO2
H (m is 0)
*


226
N
CH
CH
CH
O
CN
H (m is 0)
*


227
N
CH
CH
CH
O
OMe
H (m is 0)
*


228
N
CH
CCHF2
CH
O
F
H (m is 0)
307


229
N
CH
CCl
CH
O
Cl
3-OH
324


230
N
CH
CBr
CH
O
Br
3-CHO
425


231
N
CH
CBr
CH
O
Br
3-CHF2
447


232
N
CH
CCHF2
CH
O
Cl
3-Br
*


233
N
CH
CBr
CH
O
CN
H (m is 0)
*


234
N
CH
CBr
CH
O
OMe
H (m is 0)
*


235
N
CH
CBr
CH
O
Cl
3-CN
377


236
N
CH
CCN
CH
O
Cl
3-CHF2
348


237
N
CH
CCN
CH
O
Cl
3-CHO
326


238
N
CH
CBr
CH
O
Cl
3-CN, 5-F
395


239
N
CH
CBr
CH
O
Br
3-CN, 5-F
440


240
N
CH
CCN
CH
O
F
3-CHF2
332


241
N
CH
COCH2CF3
CH
O
F
H (m is 0)
355


242
N
CH
CCN
CH
O
Cl
3-CH2F
330


243
N
CH
CCN
CH
O
Br
3-CH2F
375


244
N
CH
CI
CH
O
Br
3-CH2F
476


245
N
CH
CI
CH
O
Cl
3-CH2F
431


246
N
CH
CSCF3
CH
O
Br
H (m is 0)
417


247
N
CH
CSCF3
CH
O
F
H (m is 0)
357


248
N
CH
CCF3
CH
O
Cl
3-CO2Me
399


249
N
CH
CCl
CH
O
F
3-CH2F
322


250
N
CH
CCl
CH
O
Cl
3-CH2F
340


251
N
CH
CCl
CH
O
Br
3-CH2F
384


252
CH
N
CCF3
CH
O
Cl
3-CN
366


253
N
CH
CCHF2
CH
O
Cl
3-CN
348


254
N
CH
CO(i-Pr)
CH
O
Br
3-CN
*


255
N
CH
CCF3
CH
O
Cl
3-C(═O)NMe2
412


256
N
CH
CCF3
CH
O
Cl
3-C(═O)NHMe
398


257
N
CH
CCF3
CH
O
Cl
3-C(═O)NHEt
412


258
N
CH
COCHF2
CH
O
Cl
3-Cl
*


259
CH
N
CH
CBr
O
Cl
3-CHF2
402


260
CH
N
CMe
CH
O
Cl
3-CN
312


261
CH
N
CH
CH
O
Cl
3-CN
298


262
N
CH
CCF3
CH
O
Cl
3-C(═O)N(Me)Et
426


263
N
CH
CCF3
CH
O
Cl
3-C(═O)NEt2
440


264
N
CMe
CH
CMe
O
Cl
H (m is 0)
301


265
N
CMe
CH
CCF2
O
Cl
H (m is 0)
334


266
N
CCF3
CH
CMe
O
Cl
H (m is 0)
355


267
N
CCHF2
CH
CMe
O
Cl
H (m is 0)
337


268
N
CCHF2
CH
CCF2
O
Cl
H (m is 0)
121


269
CH
CH
CH
CH
O
Cl
H (m is 0)
*


270
N
CH
COCH2CF3
CH
O
Cl
3-F
389


271
N
CH
COCHF2
CH
O
Cl
3-F
357


272
N
N
CCHO
CH
O
Cl
H (m is 0)
302


273
N
N
CCN
CH
O
Cl
3-CN
324


274
N
CH
COCH2CF3
CH
O
Cl
3-CN
396


275
N
CH
CBr
CH
O
H
H (m is 0)
318


276
N
N
C(3-CF3—Ph)
CH
O
Cl
3-F
436


277
N
N
C(3-thienyl)
CH
O
Cl
3-F
374


278
N
CH
CCF3
CH
O
Cl
3-C(═O)NH2
384


279
N
CH
CCF3
CH
O
Cl
3-[3-(1,2,4-oxadiazole)]
409


280
N
N
CC(═O)CH3
CH
O
Cl
3-Br
396


281
N
CH
CC(═O)NH2
CH
O
Cl
H (m is 0)
316


282
N
CH
CSO2NH2
CH
O
Cl
H (m is 0)
352


283
N
CH
CSO2NH(t-Bu)
CH
O
Cl
H (m is 0)
408


284
N
CH
C(3-CF3-pyrazol-1-yl)
CH
O
Cl
3-CN
432


285
N
CH
CB(OCMe2CMe2O)
CH
O
Cl
3-CN
424


286
N
CH
C(4-pyridinyl)
CH
O
Cl
H (m is 0)
350


287
N
CH
CBr
CH
O
Cl
3-(2-oxazolyl)
419


288
N
CH
CBr
CH
O
Cl
3-CH═NNH2
394


289
N
CH
CBr
CH
O
Cl
3-CH═NNHMe
408


290
N
CH
CBr
CH
O
Cl
3-(3-pyridinyl)
429


291
N
CH
CBr
CH
O
Cl
3-(4-isoxazolyl)
419


292
N
CH
CCl
CH
O
Cl
3-C(═S)NH2
365


293
N
CH
CBr
CH
O
Cl
3-C≡CSi(Me)3
449


294
N
CH
CCO2Et
CH
O
Br
3-CN
416


295
N
CH
CCl
CH
O
Cl
3-CH═NNH2
350


296
N
CH
CCl
CH
O
Cl
3-CH═NNHMe
363


297
N
N
CSi(Me)3
CH
O
Cl
H (m is 0)
346


298
N
CH
CCF3
CH
O
Cl
3-[2-(1,3,4-oxadiazole)]
409


299
N
CH
CCF3
CH
O
Cl
3-[5-(3-Me-1,2,4-
423









oxadiazole)]



300
N
N
CSi(Me)3
CH
O
Cl
3-Br
*


301
N
CH
CCO2Et
CH
O
Cl
3-CN
*


302
N
N
CCO2Et
CH
O
Cl
H (m is 0)
346


303
N
N
C(3,5-diF—Ph)
CH
O
Cl
3-Br
466


304
N
CH
CNO2
CH
O
Cl
3-CN
343


305
N
N
CCHF2
CH
O
Br
3-F
386





* See Index Table B for 1H NMR data.














INDEX TABLE B





No.
1H NMR Data (CDCl3 solution unless indicated otherwise)a
















1
8.48 (s, 2H), 7.96 (s, 1H), 7.80 (d, 1H), 7.49 (t, 1H), 7.44 (t, 1H), 7.35 (d, 1H), 6.57 (s, 1H)


2
8.39 (s, 2H), 7.93 (s, 1H), 7.81 (d, 1H), 7.48 (t, 1H), 7.42 (t, 1H), 7.35 (d, 1H), 6.58 (s, 1H)


3
8.42 (s, 2H), 7.92 (s, 1H), 7.77 (d, 1H), 7.52 (s, 1H), 7.42 (m, 2H), 7.31 (d, 1H)


4
8.70 (s, 2H), 7.90 (s, 1H), 7.78 (d, 1H), 7.52 (t, 1H), 7.47 (t, 1H), 7.38 (d, 1H), 6.57 (s, 1H)


5
8.49 (s, 2H), 7.91 (s, 1H), 7.77 (d, 1H), 7.52 (s, 1H), 7.42 (m, 2H), 7.30 (d, 1H)


6
8.72 (s, 2H), 7.88 (s, 1H), 7.77 (d, 1H), 7.50 (s, 1H), 7.44-7.46 (m, 2H), 7.32 (d, 1H)


7
8.41 (s, 2H), 7.94 (s, 1H), 7.77 (d, 1H), 7.55 (s, 1H), 7.42 (m, 2H), 7.32 (d, 1H)


8
8.49 (s, 2H), 7.96 (s, 1H), 7.78 (d, 1H), 7.56 (s, 1H), 7.41-7.46 (m, 2H), 7.32 (d, 1H)


9
8.30 (s, 2H), 7.99 (s, 1H), 7.78 (d, 1H), 7.55 (s, 1H), 7.36-7.43 (m, 2H), 7.28 (d, 1H), 2.23 (s, 1H)


10
8.34 (s, 2H), 7.97 (s, 1H), 7.78 (d, 1H), 7.55 (s, 1H), 7.41-7.47 (m, 2H), 7.32 (d, 1H)


11
8.34 (s, 2H), 7.92 (s, 1H), 7.78 (d, 1H), 7.51 (s, 1H), 7.39-7.45 (m, 2H), 7.30 (d, 1H)


12
8.38 (s, 2H), 7.90 (s, 1H), 7.82 (d, 1H), 7.59 (s, 1H), 7.43 (m, 2H), 7.32 (d, 1H), 6.31 (s, 1H)


13
8.46 (s, 2H), 7.90 (s, 1H), 7.81 (d, 1H), 7.59 (s, 1H), 7.41 (m, 2H), 7.31 (d, 1H), 6.32 (s, 1H)


14
8.29 (s, 2H), 7.91 (s, 1H), 7.83 (d, 1H), 7.59 (s, 1H), 7.41 (m, 2H), 7.32 (d, 1H), 6.30 (s, 1H)


15
8.30 (s, 2H), 7.96 (s, 1H), 7.80 (d, 1H), 7.51 (s, 1H), 7.35-7.44 (m, 2H), 7.28 (d, 1H), 2.23 (s, 1H)


16
8.41 (s, 2H), 8.18 (s, 1H), 7.77 (m, 2H), 7.48 (t, 1H), 7.44 (t, 1H), 7.35 (d, 1H)


17
8.71 (s, 2H), 8.14 (s, 1H), 7.75 (m, 2H), 7.51 (t, 1H), 7.48 (t, 1H), 7.38 (d, 1H)


18
8.49 (s, 2H), 8.18 (s, 1H), 7.78 (m, 2H), 7.48 (t, 1H), 7.44 (t, 1H), 7.34 (d, 1H)


19
8.44 (s, 2H), 7.92 (s, 1H), 7.78 (d, 1H), 7.39-7.47 (m, 2H), 7.30 (d, 1H)


20
8.48 (s, 2H), 7.82 (s, 1H), 7.81 (d, 1H), 7.38-7.46 (m, 2H), 7.30 (d, 1H), 6.32 (s, 1H)


21
8.40 (s, 2H), 7.82 (s, 1H), 7.81 (d, 1H), 7.38-7.45 (m, 2H), 7.31 (d, 1H), 6.32 (s, 1H)


22
8.37 (s, 2H), 8.18 (s, 1H), 7.86 (s, 1H), 7.85 (d, 2H), 7.41-7.47 (m, 4H), 7.32-7.38 (m, 3H), 7.23 (d,



1H)


23
8.38 (s, 2H), 7.80 (d, 1H), 7.68 (s, 1H), 7.35-7.42 (m, 3H), 7.28 (d, 1H), 6.30 (s, 1H), 2.03 (s, 3H)


24
8.52 (s, 2H), 7.92 (s, 1H), 7.78 (d, 1H), 7.39-7.47 (m, 2H), 7.29 (d, 1H)


25
8.41 (s, 2H), 7.95 (s, 1H), 7.77 (d, 1H), 7.58 (s, 1H), 7.38-7.47 (m, 2H), 7.31 (d, 1H)


26
8.48 (s, 2H), 7.95 (s, 1H), 7.77 (d, 1H), 7.58 (s, 1H), 7.39-7.45 (m, 2H), 7.29 (d, 1H)


27
8.38 (s, 2H), 7.81 (s, 1H), 7.80 (d, 1H), 7.60 (s, 1H), 7.37-7.41 (m, 2H), 7.29 (m, 1H), 6.17 (d, 1H),



5.98 (d, 1H), 1.81 (d, 3H)


29
8.37 (s, 2H), 7.76 (d, 1H), 7.71 (s, 1H), 7.38 (m, 2H), 7.32 (d, 1H), 6.1 (s, 1H), 1.21 (s, 9H)


30
8.46 (s, 2H), 7.76 (d, 1H), 7.71 (s, 1H), 7.38 (m, 2H), 7.31 (d, 1H), 6.12 (s, 1H), 1.22 (s, 9H)


31
8.39 (s, 2H), 7.91 (s, 1H), 7.8 (d, 1H), 7.68 (s, 1H), 7.40 (m, 2H), 7.30 (d, 1H), 6.49 (m, 1H),



5.47 (dd, 1H), 5.08 (dd, 1H)


32
8.38 (s, 2H), 7.90 (d, 1H), 7.82 (s, 1H), 7.60 (d, 1H), 7.40 (m, 2H), 7.31 (d, 1H), 5.98 (dd, 1H),



5.63 (dd, 1H), 1.81 (t, 3H)


33
8.43 (s, 2H), 8.34 (s, 1H), 7.88 (s, 1H), 7.80 (d, 1H), 7.56 (t, 1H), 7.46 (t, 1H), 7.34 (d, 1H)


34
8.39 (s, 2H), 7.59 (s, 1H), 7.51 (m, 1H), 7.42 (d, 2H), 7.34 (d, 1H), 7.15 (s, 1H)


36
8.38 (s, 2H), 7.80 (m, 2H), 7.37 (m, 2H), 7.28 (d, 1H), 6.08 (s, 1H), 2.25 (s, 3H)


37
8.41 (s, 2H), 7.88 (s, 1H), 7.76 (d, 1H), 7.38 (m, 2H), 7.28 (d, 1H), 2.22 (s, 3H)


38
8.41 (s, 2H), 7.88 (s, 1H), 7.76 (d, 1H), 7.37-4.40 (m, 2H), 7.28 (d, 1H), 2.22 (s, 3H)


39
8.42 (s, 2H), 7.87 (s, 1H), 7.78 (d, 1H), 7.38 (m, 2H), 7.28 (d, 1H), 2.22 (s, 3H)


46
8.51 (s, 1H), 8.44 (s, 2H), 7.82 (d, 1H), 7.51 (t, 1H), 7.45 (t, 1H), 7.35 (d, 1H)


47
8.33 (s, 2H), 8.19 (s, 1H), 7.80 (s, 1H), 7.78 (d, 1H), 7.48 (t, 1H), 7.44 (t, 1H), 7.33 (d, 1H)


49
8.39 (s, 2H), 7.89 (d, 1H), 7.77 (d, 1H), 7.58 (1H), 7.39 (d, 1H), 7.33 (1H), 6.30 (d, 1H)


50
8.47 (s, 2H), 7.89 (d, 1H), 7.78 (d, 1H), 7.59 (s, 1H), 7.39 (d, 1H), 7.33 (1H), 6.30 (d, 1H)


51
8.43 (s, 2H), 7.93 (s, 1H), 7.73 (d, 1H), 7.55 (s, 1H), 7.40 (d, 1H), 7.33 (s, 1H)


56
8.53 (s, 2H), 8.03 (s, 1H), 7.96 (dd, 1H), 7.65-7.54 (m, 1H), 7.50-7.47 (m, 1H), 7.41 (dd, 1H)


58
8.40 (s, 2H), 8.05 (s, 1H), 7.85 (s, 1H), 7.78 (d, 1H), 7.6-7.7 (m, 2H)


59
8.49 (s, 2H), 8.05 (s, 1H), 7.85 (s, 1H), 7.79 (d, 1H), 7.62-7.65 (m, 2H)


65
8.41 (s, 2H), 7.66-7.64 (m, 1H), 7.53 (s, 1H), 7.53 (s, 1H), 7.45-7.40 (m, 1H), 7.32-7.28 (m, 1H)


66
8.41 (s, 2H), 7.90-7.86 (m, 1H), 7.54 (d, 1H), 7.50 (d, 1H), 7.33-7.26 (m, 2H)


67
8.40 (s, 2H), 7.56 (s, 1H), 7.54-7.50 (m, 2H), 7.24 (dd, 1H), 7.22-7.18 (m, 1H), 2.13 (s, 3H)


68
10.06 (s, 1H), 8.43 (s, 2H), 8.16 (s, 1H), 7.64 (s, 1H), 7.26 (t, 1H), 7.04 (dd, 1H), 6.79 (dd, 1H)


69
8.40 (s, 2H), 7.55 (d, 1H), 7.53-7.45 (m, 3H), 7.08 (dd, 1H), 7.01 (dd, 1H), 4.32 (q, 3H)


74
8.39 (s, 2H), 7.76 (d, 1H), 7.66 (t, 1H), 7.60 (d, 1H), 7.55 (s, 1H), 7.11 (s, 1H)


79
8.32 (s, 2H), 8.05 (s, 1H), 7.84 (s, 1H), 7.77 (d, 1H), 7.63-7.65 (m, 2H)


80
8.40 (s, 2H), 8.08 (s, 1H), 7.80 (d, 1H), 7.72 (s, 1H), 7.41-7.50 (m, 2H), 7.33 (d, 1H), 6.67 (t, 1H)


81
8.48 (s, 2H), 8.08 (s, 1H), 7.80 (d, 1H), 7.72 (s, 1H), 7.42-7.47 (m, 2H), 7.33 (d, 1H), 6.67 (t, 1H)


89
8.30 (s, 2H), 7.72 (m, 1H), 7.47-7.60 (m, 2H), 7.40 (m, 2H), 3.89 (m, 2H), 1.34 (m, 3H)


99
8.39 (s, 2H), 7.73 (m, 1H), 7.52-7.61 (m, 2H), 7.49 (m, 1H), 7.46 (m, 1H), 5.83-6.13 (m, 2H),



4.03-4.09 (m, 2H)


101
8.30 (s, 2H), 7.44-7.50 (m, 4H), 7.28 (m, 1H), 6.32-6.47 (s, 1H)


103
8.38 (s, 2H), 7.38-7.51 (m, 2H), 7.30 (m, 1H), 7.25 (m, 1H), 7.15 (m, 1H), 4.03-4.18 (m, 1H),



1.25 (m, 6H)


105
8.39 (s, 2H), 7.89 (d, 1H), 7.71 (s, 1H), 7.64 (s, 1H), 7.27-7.33 (m, 2H), 7.69 (t, 1H)


110
8.40 (s, 2H), 7.48 (s, 1H), 7.47 (m, 1H), 7.39 (m, 1H), 7.29 (m, 1H), 7.25-7.27 (m, 1H), 4.20 (m, 2H)


111
7.60-7.65 (m, 1H), 7.65-7.72 (m, 1H), 7.79 (d, J = 7.83 Hz, 1H), 7.96 (s, 1H), 8.21 (s, 1H), 8.36 (s, 2H)


124
9.74 (s, 1H), 8.35 (s, 2H), 7.40-7.53 (m, 4H), 7.33-7.36 (m, 1H), 6.91-6.94 (m, 1H), 6.61 (dd, 1H)


126
8.31 (s, 2H), 7.48-7.42 (m, 1H), 7.38-7.36 (m, 2H), 7.22-7.14 (m, 2H), 4.26-4.17 (m, 2H)


132
8.37 (s, 2H), 8.14 (s, 1H), 7.80 (d, 1H), 7.71 (s, 1H), 7.41-7.50 (2 × t, 1H each), 7.35 (d, 1H)


133
8.38 (s, 2H), 7.91 (d, 1H), 7.72 (d, 2H), 7.28-7.37 (m, 2H)


134
8.36 (s, 2H), 8.01 (s, 1H), 7.78 (s + d, 2H), 7.63 (2 × t, 2H)


143
8.43 (s, 1H), 8.40 (s, 2H), 8.01 (s, 1H), 7.82 (d, 1H), 7.53 (t, 1H), 7.46 (t, 1H), 7.37 (d, 1H)


148
8.38 (s, 2H), 7.68-7.56 (m, 1H), 7.44-7.33 (m, 1H), 7.31-7.27 (m, 2H), 7.15-7.11 (m, 1H),



4.16-4.05 (m, 1H), 1.27-1.24 (m, 6H)


156
8.38 (s, 2H), 7.68-7.56 (m, 1H), 7.44-7.33 (m, 1H), 7.31-7.27 (m, 2H), 7.15-7.11 (m, 1H),



4.16-4.05 (m, 1H), 1.27-1.24 (m, 6H)


157
8.32 (s, 2H), 7.73-7.54 (m, 1H), 7.43-7.36 (m, 2H), 7.31-7.27 (m, 2H), 4.26-4.17 (m, 2H)


180
8.28 (s, 2H), 8.08-7.99 (m, 1H), 7.84 (s, 1H), 7.78-7.72 (m, 1H), 7.67-7.57 (m, 2H),



2.42-2.07 (m, 4H)


186
8.39 (s, 2H), 7.80-7.77 (m, 1H), 7.61-7.60 (m, 1H), 7.40-7.36 (m, 2H), 7.36-7.33 (m, 1H),



7.32-7.27 (m, 1H), 3.70 (s, 3H)


203
3.95 (s, 3H), 7.31 (d, 1H), 7.51 (m, 1H), 7.53 (s, 1H), 7.57 (s, 1H), 7.69 (s, 1H), 7.94 (d, 1H), 8.40 (s,



2H)


213
7.42 (d, 1H), 7.61 (s, 1H), 7.67 (m, 1H), 8.05 (s, 1H), 8.2 (m, 1H), 8.45 (s, 2H)


225
9.24 (s, 2H), 7.87 (s, 1H), 7.73 (d, 1H), 7.49 (m, 3H), 7.32 (d, 1H)


226
8.69 (s, 2H), 7.82 (s, 1H), 7.75 (d, 1H), 7.54 (s, 1H), 7.45 (m, 2H), 7.35 (d, 1H), 6.30 (s, 1H)


227
8.12 (s, 2H), 7.98 (s, 1H), 7.85 (d, 1H), 7.59 (s, 1H), 7.38 (m, 2H), 7.29 (d, 1H), 6.29 (s, 1H),



3.82 (s, 3H)


232
8.39 (s, 2H), 7.71 (s, 1H), 7.65-7.69 (m, 2H), 7.45 (t, 1H), 7.32 (d, 2H), 6.68 (t, 1H)


233
8.73 (s, 2H), 7.87 (s, 1H), 7.73 (d, 1H), 7.52 (s, 1H), 7.47 (m, 2H), 7.33 (d, 1H)


234
8.15 (s, 2H), 8.00 (s, 1H), 7.79 (d, 1H), 7.56 (s, 1H), 7.38 (m, 2H), 7.28 (d, 1H), 3.85 (s, 3H)


254
8.45 (s, 2H), 7.77-7.66 (m, 1H), 7.61-7.45 (m, 2H), 7.39 (s, 2H), 4.17-4.08 (m, 1H),



1.28-1.24 (m, 6H)


258
8.39 (s, 2H), 7.50-7.44 (m, 4H), 7.29-7.26 (m, 1H), 6.46-6.16 (m, 1H)


269
8.32 (s, 2H), 7.28-7.47 (m, 4H), 6.89 (t, 2H), 6.13 (t, 2H)


300
8.37 (s, 2H), 7.69 (dd, J = 8.2, 1.3 Hz, 1H), 7.66 (s, 1H), 7.47 (t, J = 8.2 Hz, 1H), 7.34 (dd, J = 8.3, 1.3 Hz,



1H), 0.30 (m, 9H)


301
8.48-8.37 (m, 2H), 8.22 (s, 1H), 8.04 (s, 1H), 7.85-7.71 (m, 1H), 7.68-7.57 (m, 2H),



4.36-4.24 (m, 2H), 1.41-1.26 (m, 3H)





a1H NMR data are in ppm downfield from tetramethylsilane at 500 MHz. Couplings are designated by (s)-singlet, (d)-doublet, (t)-triplet, (m)-multiplet and (dd)-doublet of doublets.






Biological Examples of the Invention
Test A
Seeds of plant species selected from barnyardgrass (Echinochloa crus-galli), kochia (Kochia scoparia), ragweed (common ragweed, Ambrosia elatior), Italian ryegrass (Lolium multiflorum), large (Lg) crabgrass (Digitaria sanguinalis), giant foxtail (Setaria faberii), morningglory (Ipomoea spp.), pigweed (Amaranthus retroflexus), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), and corn (Zea mays) were planted into a blend of loam soil and sand and treated preemergence with a directed soil spray using test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant.
At the same time, plants selected from these crop and weed species and also blackgrass (Alopecurus myosuroides), and galium (catchweed bedstraw, Galium aparine) were planted in pots containing the same blend of loam soil and sand and treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from 2 to 10 cm and were in the one- to two-leaf stage for the postemergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately 10 days, after which time all treated plants were compared to untreated controls and visually evaluated for injury. Plant response ratings, summarized in Table A, are based on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test result.








TABLE A








Postemergence



1000 g ai/ha



Compounds


























12
13
14
53
54
55
56
65
66
67
69
70
102
114
115
116
123
139





Barnyardgrass
90
90
20
90
30
10
30
100
 80
20
50
80
50
100 
90
90
100
0


Blackgrass
—
—
—
—
—
—
—
—
—
—
—
—
40
—
—
—
90
0


Corn
30
40
20
30
50
20
20
 70
 40
10
20
10
20
70
90
60
70
20 


Crabgrass, Large
80
90
30
70
100
40
40
100
100
10
80
60
—
90
90
100
—
—


Foxtail, Giant
80
100 
40
80
70
60
30
100
100
10
70
60
40
90
90
90
90
0


Galium
—
—
—
—
—
—
—
—
—
—
—
—
70
—
—
—
100
10 


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
30
—
—
—
100
0


Morningglory
90
90
70
100 
100
80
 0
100
100
10
30
20
—
80
100 
100
—
—


Pigweed
100 
100 
100 
100 
100
90
90
100
100
100 
100 
70
80
100 
100 
100
100
30 


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
20
—
—
—
100
0


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
 0
—
—
—
90
0


Velvetleaf
100 
100 
90
100 
80
100 
100 
100
100
70
60
70
—
100 
100 
100
—
—


Wheat
20
60
20
30
0
 0
 0
 60
 20
 0
30
 0
 0
60
90
50
70
0












Postemergence



1000 g ai/ha



Compounds

























154
155
159
160
193
207
216
217
222
223
224
229
248
255
256
257
262





Barnyardgrass
100
100
70
100
90
10
0
30
100
100
90
0
70
10
10
10
10


Blackgrass
90
100
50
100
—
—
—
—
—
—
—
—
30
10
10
10
10


Corn
90
100
40
100
60
 0
0
 0
 50
 60
50
0
80
 0
 0
 0
 0


Crabgrass, Large
—
—
—
—
80
40
40
60
100
100
80
0
—
—
—
—
—


Foxtail, Giant
100
100
90
100
80
60
30
50
 90
 90
90
0
100 
10
10
10
10


Galium
100
100
90
100
—
—
—
—
—
—
—
—
100 
10
30
30
10


Kochia
100
100
100 
100
—
—
—
—
—
—
—
—
90
50
30
60
30


Morningglory
—
—
—
—
90
30
40
90
100
100
100 
0
—
—
—
—
—


Pigweed
100
100
100 
100
100 
70
100
100 
100
100
100 
60 
100 
30
10
40
50


Ragweed
100
100
80
100
—
—
—
—
—
—
—
—
50
10
10
30
10


Ryegrass, Italian
90
100
30
 90
—
—
—
—
—
—
—
—
50
 0
 0
 0
 0


Velvetleaf
—
—
—
—
90
30
100
100 
100
100
100 
0
—
—
—
—
—


Wheat
80
 90
30
100
20
 0
0
20
 40
 70
60
0
20
 0
 0
 0
 0












Postemergence










1000 g ai/ha
500 g ai/ha



Compounds
Compounds

























263
276
280
281
282
283
297
298
299
300
302
303
1
2
3
4
5





Barnyardgrass
0
20
90
0
90
0
10
90
80
0
0
20
30
70
90
0
60


Blackgrass
20
20
—
0
100 
10
—
80
80
0
0
—
—
—
—
—
—


Corn
0
10
50
10
50
0
 0
70
70
10
0
10
10
40
40
0
30


Crabgrass, Large
—
—
90
—
—
—
30
—
—
—
—
20
50
60
80
0
80


Foxtail, Giant
0
20
90
0
60
0
10
90
90
30
0
20
60
80
90
0
100 


Galium
10
20
—
60
30
30
—
80
80
40
0
—
—
—
—
—
—


Kochia
10
40
—
70
90
10
—
100 
70
20
0
—
—
—
—
—
—


Morningglory
—
—
30
—
—
—
30
—
—
—
—
30
20
70
70
0
90


Pigweed
10
80
100 
70
80
20
70
100 
100 
60
0
90
100 
100 
100 
20 
100 


Ragweed
0
30
—
70
100 
20
—
90
30
0
0
—
—
—
—
—
—


Ryegrass, Italian
0
 0
—
0
80
0
—
70
70
0
0
—
—
—
—
—
—


Velvetleaf
—
—
90
—
—
—
60
—
—
—
—
70
70
60
100 
0
100 


Wheat
0
 0
40
0
 0
0
 0
40
20
0
0
 0
 0
 0
 0
0
40












Postemergence



500 g ai/ha



Compounds

























6
7
8
9
10
11
15
16
17
18
19
20
21
22
23
24
25





Barnyardgrass
100
100
90
90
90
90
60
100
20
100
20
30
40
70
40
0
100


Blackgrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
60
 50
30
50
50
50
20
 80
40
 90
30
30
30
30
60
0
 40


Crabgrass, Large
100
100
90
80
80
90
60
100
90
100
20
30
50
70
60
0
100


Foxtail, Giant
100
100
90
90
90
90
70
100
90
100
30
60
90
90
90
0
100


Galium
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
70
100
100 
30
100 
100 
20
100
50
100
40
40
80
90
90
0
 90


Pigweed
100
100
100 
90
100 
100 
100 
100
100 
100
90
100 
100 
100 
100 
60 
100


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
100
100
100 
100 
100 
100 
100 
100
100 
100
60
70
80
100 
100 
0
100


Wheat
90
 50
20
30
60
20
10
 80
50
 50
 0
20
20
 0
20
0
 60












Postemergence



500 g ai/ha



Compounds

























26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42





Barnyardgrass
90
10
10
0
10
50
20
100
50
0
0
0
0
 0
20
50
 0


Blackgrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
30
10
20
0
 0
20
20
100
20
20 
0
0
0
10
0
20
 0


Crabgrass, Large
100 
60
20
40
40
60
50
 80
60
0
10 
0
10 
10
70
70
50


Foxtail, Giant
90
30
10
30
10
50
30
100
70
0
0
0
0
 0
60
80
30


Galium
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
90
50
10
0
 0
30
 0
—
80
—
—
—
—
—
100
30
40


Pigweed
100 
70
30
50
30
70
70
100
100 
40 
20 
10 
10 
40
60
80
30


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
100 
70
30
40
30
100 
100 
100
100 
100 
70 
40 
20 
30
100
100 
70


Wheat
30
 0
 0
0
 0
 0
 0
 90
20
0
0
0
0
 0
0
 0
 0












Postemergence



500 g ai/ha



Compounds

























43
44
45
46
47
48
49
50
51
52
57
58
59
60
61
62
63





Barnyardgrass
10
90
100 
20
100
10
10
10
10
100
100
100
100
50
0
100
70


Blackgrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
10
40
70
30
 90
 0
 0
 0
20
 90
 90
100
100
30
0
 90
30


Crabgrass, Large
20
100 
100 
20
100
20
10
10
20
100
100
100
100
70
0
100
90


Foxtail, Giant
40
90
90
20
100
20
10
 0
10
100
100
100
100
80
0
100
80


Galium
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
50
60
20
50
100
30
20
30
20
100
 80
100
100
50
0
100
80


Pigweed
40
100 
80
80
100
50
40
30
70
100
100
100
100
100 
0
100
100 


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
100 
100 
100 
40
100
10
30
10
60
100
100
100
100
100 
30 
100
100 


Wheat
 0
30
40
 0
100
 0
 0
 0
 0
100
 30
100
100
10
0
100
10












Postemergence



500 g ai/ha



Compounds

























64
68
71
72
73
74
75
76
77
78
79
80
81
82
83
84
85





Barnyardgrass
100
0
90
100
 90
90
70
100
70
50
100
100
100
20
100
100
90


Blackgrass
—
0
—
—
—
—
—
—
—
—
—
—
—
50
100
100
80


Corn
 90
0
60
 60
 80
70
40
80
40
30
100
 10
30
10
60
70
70


Crabgrass, Large
100
—
100 
100
100
90
70
100
90
100 
100
100
90
—
—
—
—


Foxtail, Giant
100
0
90
100
100
90
80
90
90
90
100
 90
90
20
100
100
90


Galium
—
0
—
—
—
—
—
—
—
—
—
—
—
20
100
100
100


Kochia
—
0
—
—
—
—
—
—
—
—
—
—
—
10
100
100
100


Morningglory
 80
—
90
100
100
100 
60
90
100 
90
100
100
100
—
—
—
—


Pigweed
100
0
100 
100
100
100 
100 
100
100 
100 
100
100
100
40
100
100
100


Ragweed
—
0
—
—
—
—
—
—
—
—
—
—
—
10
80
90
60


Ryegrass, Italian
—
0
—
—
—
—
—
—
—
—
—
—
—
20
80
80
100


Velvetleaf
100
—
100 
100
100
100 
70
100
100 
100 
100
100
100
—
—
—
—


Wheat
 30
0
40
 50
 50
50
 0
10
30
20
 90
 80
60
30
60
80
70












Postemergence



500 g ai/ha



Compounds

























86
87
88
89
90
91
92
93
94
95
96
97
98
111
112
113
117





Barnyardgrass
100
20
80
90
100
10
100
0
90
80
30
100
90
90
90
80
90


Blackgrass
100
50
100
90
70
30
—
—
—
—
—
—
—
—
—
—
80


Corn
100
20
50
90
80
 0
80
0
50
70
10
 90
70
90
70
60
50


Crabgrass, Large
—
—
—
—
—
—
90
0
90
90
30
100
100
90
100
70
—


Foxtail, Giant
100
60
80
90
90
10
90
0
90
80
20
 90
90
90
90
60
90


Galium
100
90
100
90
100
70
—
—
—
—
—
—
—
—
—
—
100


Kochia
100
90
100
90
100
30
—
—
—
—
—
—
—
—
—
—
100


Morningglory
—
—
—
—
—
—
100
0
100 
90
10
100
100
90
100
30
—


Pigweed
100
100 
100
100 
100
50
100
0
100 
100 
40
100
100
100 
100
80
100


Ragweed
100
70
30
90
80
30
—
—
—
—
—
—
—
—
—
—
100


Ryegrass, Italian
100
40
90
90
80
 0
—
—
—
—
—
—
—
—
—
—
90


Velvetleaf
—
—
—
—
—
—
100
0
100 
100 
10
100
100
100 
100
80
—


Wheat
 90
 0
50
70
50
10
70
0
50
40
 0
 70
60
80
70
60
70












Postemergence



500 g ai/ha



Compounds

























129
130
131
132
134
135
136
137
138
142
143
145
146
147
150
161
162





Barnyardgrass
90
0
0
70
90
100
90
100
100
0
80
100
60
90
—
0
10


Blackgrass
90
0
0
90
90
90
100
90
90
0
90
100
70
100
100
—
—


Corn
50
0
0
50
60
80
60
80
90
0
40
 60
30
90
 90
0
10


Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
0
10


Foxtail, Giant
100
0
0
90
100
100
90
100
100
0
100
100
80
90
100
0
 0


Galium
100
0
0
100 
100
90
100
100
100
0
100
100
100
100
100
—
—


Kochia
100
0
0
100 
100
70
100
100
100
70 
90
100
100
100
100
—
—


Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
0
10


Pigweed
100
0
0
100 
100
100
100
100
100
0
100
100
100
100
100
80 
70


Ragweed
90
0
0
30
60
100
100
100
60
0
100
100
10
100
 60
—
—


Ryegrass, Italian
90
0
0
60
100
70
90
80
90
0
90
100
40
90
100
—
—


Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
20 
50


Wheat
70
0
0
60
70
60
50
70
90
0
30
 70
0
80
 90
0
 0












Postemergence



500 g ai/ha



Compounds

























163
164
165
166
167
168
170
171
172
173
174
175
176
177
178
179
180





Barnyardgrass
100
100
 0
100
100
90
90
0
60
30
0
0
40
100
100
100
100


Blackgrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
50
 90
 0
 60
50
30
90
0
20
20
0
0
20
 70
 70
 60
90


Crabgrass, Large
90
100
10
100
90
90
90
0
30
40
0
0
40
100
100
100
90


Foxtail, Giant
90
100
20
 90
90
90
90
0
20
50
0
0
50
100
100
 90
90


Galium
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
100
100
20
100
100
100 
90
0
90
 0
0
0
80
100
100
100
100


Pigweed
100
100
80
100
100
100 
100 
100 
100 
100 
0
0
100 
100
100
100
100


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
100
100
30
100
100
100 
100 
70 
100 
70
0
0
90
100
100
100
100


Wheat
60
 90
 0
 70
60
50
70
0
 0
 0
0
0
10
 90
 80
 60
80












Postemergence



500 g ai/ha



Compounds

























181
182
183
184
185
186
187
188
189
190
191
192
194
195
196
197
198





Barnyardgrass
90
0
0
90
80
70
90
90
90
10
90
90
 90
20
50
60
50


Blackgrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
40
0
0
70
20
30
70
50
40
20
40
60
 60
20
40
10
20


Crabgrass, Large
90
0
0
80
90
70
100
80
80
50
90
90
100
60
90
70
90


Foxtail, Giant
90
0
0
80
80
80
90
90
80
40
90
90
100
50
80
70
80


Galium
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
100 
0
0
90
90
100 
100
100 
100 
90
100 
100 
100
70
80
30
70


Pigweed
100 
90 
50 
100 
100 
100 
100
100 
100 
100 
100 
100 
100
80
100 
60
100 


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
100 
30 
30 
90
100 
90
100
100 
100 
80
100 
100 
100
100 
100 
100 
100 


Wheat
30
0
0
90
40
60
60
30
50
 0
40
50
 60
 0
10
 0
10












Postemergence



500 g ai/ha



Compounds

























199
200
201
202
203
204
205
206
208
209
210
211
212
213
214
215
218





Barnyardgrass
80
90
10
 0
70
 90
0
0
0
100 
40
50
 0
10
0
30
70


Blackgrass
—
—
—
—
—
—
—
—
—
—
—
—
50
—
—
—
—


Corn
60
60
 0
 0
50
 60
0
0
20
70
30
0
 0
30
0
20
40


Crabgrass, Large
90
90
30
50
80
100
0
0
20
90
70
50
—
70
0
30
70


Foxtail, Giant
90
90
40
30
80
100
0
0
20
90
60
60
50
30
0
10
70


Galium
—
—
—
—
—
—
—
—
—
—
—
—
30
—
—
—
—


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
10
—
—
—
—


Morningglory
60
100 
20
20
70
100
0
0
80
90
30
100
—
30
0
10
90


Pigweed
100 
100 
40
50
90
100
0
0
100 
100 
100 
100
30
100 
0
80
100 


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
10
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
30
—
—
—
—


Velvetleaf
100 
100 
70
70
90
100
20 
20 
60
100 
80
90
—
20
0
50
100 


Wheat
30
60
 0
 0
20
 70
0
0
 0
70
 0
0
30
 0
0
 0
20












Postemergence



500 g ai/ha



Compounds

























219
220
221
225
226
227
228
230
231
232
233
234
235
236
237
238
239





Barnyardgrass
100
100
100
10 
0
 0
90
20
90
90
20
70
0
100
0
100 
80


Blackgrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
 70
 70
50
0
0
 0
10
 0
90
90
 0
30
0
100
0
80
20


Crabgrass, Large
100
100
100
10 
0
10
90
10
90
90
10
60
30
100
0
90
70


Foxtail, Giant
 90
 90
90
0
0
10
90
20
90
90
20
70
30
100
0
90
70


Galium
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
100
100
100
0
0
10
100 
 0
90
90
 0
60
30
100
0
60
40


Pigweed
100
100
100
0
10 
60
100 
60
100 
100 
50
100 
100
100
70 
100 
100 


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
100
100
100
0
10 
90
100 
30
100 
100 
30
100 
30
100
30 
100 
60


Wheat
 70
 60
30
0
0
 0
70
 0
50
50
 0
20
0
100
0
60
 0












Postemergence



500 g ai/ha



Compounds

























240
252
273
274
275
284
285
287
288
289
290
291
292
293
294
295
296





Barnyardgrass
100
100
90
100
 0
90
30
0
10
20
 0
40
90
10
60
0
0


Blackgrass
100
100
80
—
—
70
—
—
—
—
—
—
—
—
—
—
—


Corn
 90
90
50
90
 0
40
30
0
10
10
10
10
80
20
40
0
10


Crabgrass, Large
—
—
—
90
20
—
40
20
20
20
10
60
90
30
50
0
0


Foxtail, Giant
100
100
90
90
30
90
60
0
20
30
10
50
90
30
50
0
0


Galium
100
100
100 
—
—
60
—
—
—
—
—
—
—
—
—
—
—


Kochia
 60
100
100 
—
—
100 
—
—
—
—
—
—
—
—
—
—
—


Morningglory
—
—
—
100
50
—
40
20
40
50
10
40
100 
30
30
40 
20


Pigweed
100
100
100 
100
90
100 
100 
50
100 
100 
20
70
100 
90
90
70 
100


Ragweed
100
90
90
—
—
20
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
100
70
80
—
—
60
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
—
—
—
100
90
—
80
20
30
40
30
60
100 
80
60
30 
30


Wheat
 90
90
50
80
 0
20
20
0
 0
 0
 0
 0
60
 0
40
0
20












Postemergence










500 g ai/ha
125 g ai/ha



Compounds
Compounds

























301
304
1
2
3
4
5
6
7
8
9
10
11
15
16
17
18





Barnyardgrass
0
0
10
30
10
0
10
40
90
30
30
40
10
 0
60
 0
60


Blackgrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
0
0
 0
 0
 0
0
0
20
30
0
20
20
10
 0
70
 0
30


Crabgrass, Large
0
0
20
20
10
0
30
50
80
50
30
50
70
10
80
20
70


Foxtail, Giant
0
0
10
10
30
0
40
80
90
50
30
50
70
10
100 
20
80


Galium
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
0
0
 0
30
10
0
80
40
70
70
20
90
60
10
90
20
60


Pigweed
30 
50 
50
60
90
0
100
100 
100 
100
80
100 
100 
70
100 
70
100 


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
0
0
20
—
100 
0
100
100 
100 
100
100 
100 
100 
90
100 
50
100 


Wheat
0
0
 0
 0
 0
0
0
40
30
0
 0
 0
 0
 0
70
 0
50












Postemergence



125 g ai/ha



Compounds

























19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35





Barnyardgrass
0
0
 0
50
 0
0
30
20
0
0
0
10
10
0
0
20
0


Blackgrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
0
0
 0
 0
 0
0
20
20
0
0
0
0
0
0
0
10
0


Crabgrass, Large
0
0
20
30
20
0
80
60
20
0
10
30
50
50 
20
50
0


Foxtail, Giant
0
0
30
40
40
0
90
70
0
0
20
10
40
0
70
30
0


Galium
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
0
40 
40
80
50
0
80
60
10
10 
0
0
0
0
—
60
—


Pigweed
30 
80 
90
50
90
0
100 
100 
60
10 
20
0
40
50 
100
90
0


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
30 
20 
50
50
80
—
90
90
50
0
20
20
100
80 
100
80
20 


Wheat
0
0
 0
 0
 0
0
30
 0
0
0
0
0
0
0
0
 0
0












Postemergence



125 g ai/ha



Compounds

























36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52





Barnyardgrass
0
0
0
0
0
10
0
0
30
40
0
30
0
0
0
0
90


Blackgrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
0
0
0
0
0
 0
0
0
20
10
0
40
0
0
0
0
90


Crabgrass, Large
0
0
0
0
50
20
10 
10
80
60
0
70
10 
0
0
0
90


Foxtail, Giant
0
0
0
0
10
20
0
0
50
70
0
80
0
0
0
0
90


Galium
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
—
—
—
—
70
20
20 
30
20
10
20 
80
20 
0
20 
10 
100 


Pigweed
0
0
0
10 
40
50
0
30
70
60
40 
100 
20 
0
20 
30 
100 


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
20 
20 
10 
20 
100
70
60 
60
100 
100 
0
100 
0
10 
0
50 
100 


Wheat
0
0
0
0
0
 0
0
0
 0
 0
0
60
0
0
0
0
40












Postemergence



125 g ai/ha



Compounds

























57
58
59
60
61
62
63
64
71
72
73
74
75
76
77
79
80





Barnyardgrass
90
100
100
20
0
90
30
60
80
90
90
90
30
60
40
100
70


Blackgrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
30
100
 60
 0
0
70
 0
30
30
50
40
30
 0
10
20
 80
70


Crabgrass, Large
90
100
100
10
0
90
30
80
70
100 
90
70
20
70
50
100
80


Foxtail, Giant
80
100
100
20
0
90
20
80
80
90
90
80
10
60
50
100
80


Galium
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
90
100
 90
10
0
90
30
60
70
90
90
80
50
60
70
100
90


Pigweed
100 
100
100
50
0
100 
70
100 
100 
100 
100 
100 
70
90
100 
100
100 


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
100 
100
100
50
20 
100 
60
100 
90
100 
100 
90
40
80
80
100
100 


Wheat
 0
 90
 70
 0
0
20
 0
 0
10
20
20
 0
 0
 0
 0
 80
40












Postemergence



125 g ai/ha



Compounds

























81
82
83
84
85
86
87
88
89
90
91
92
93
94
95
96
97





Barnyardgrass
50
0
90
70
90
90
20
60
40
90
0
90
0
20
50
10 
90


Blackgrass
—
10 
100
80
70
90
40
70
40
50
0
—
—
—
—
—
—


Corn
50
0
40
20
30
50
20
30
60
 0
0
50
0
30
10
0
60


Crabgrass, Large
40
—
—
—
—
—
—
—
—
—
—
80
0
50
40
10 
90


Foxtail, Giant
50
0
90
100
70
90
20
50
80
80
10
80
0
70
40
0
90


Galium
—
10 
100
100
90
100 
60
100 
90
90
40
—
—
—
—
—
—


Kochia
—
0
100
100
70
100 
50
80
80
90
10
—
—
—
—
—
—


Morningglory
50
—
—
—
—
—
—
—
—
—
—
100 
0
80
60
0
90


Pigweed
100 
10 
100
100
80
100 
60
100 
90
100 
10
100 
0
100 
100 
10 
100 


Ragweed
—
0
70
50
50
90
50
10
30
60
10
—
—
—
—
—
—


Ryegrass, Italian
—
0
50
50
60
80
30
50
 0
30
0
—
—
—
—
—
—


Velvetleaf
100 
—
—
—
—
—
—
—
—
—
—
100 
0
90
70
0
100 


Wheat
10
0
0
30
 0
50
 0
 0
20
 0
0
60
0
 0
 0
0
50












Postemergence



125 g ai/ha



Compounds

























98
99
100
101
103
106
107
108
109
110
111
112
113
117
118
119
120





Barnyardgrass
80
100
0
20
0
50
40
60
60
90
60
40
0
70
80
70
80


Blackgrass
—
90
0
20
0
50
50
80
70
80
—
—
—
40
90
70
80


Corn
40
90
0
20
0
20
20
30
40
50
30
30
10
30
50
50
50


Crabgrass, Large
80
—
—
—
—
—
—
—
—
—
60
60
20
—
—
—
—


Foxtail, Giant
80
100
0
60
0
70
70
70
70
90
80
30
10
90
80
80
70


Galium
—
100
10 
60
0
70
80
90
90
90
—
—
—
100
90
100 
100 


Kochia
—
100
0
100 
0
50
20
90
60
100 
—
—
—
100
100 
90
90


Morningglory
100 
—
—
—
—
—
—
—
—
—
80
50
20
—
—
—
—


Pigweed
100 
100
10 
90
0
60
60
80
90
100 
100 
100 
60
100
100 
100 
100 


Ragweed
—
60
0
20
0
50
40
30
30
50
—
—
—
50
80
50
50


Ryegrass, Italian
—
60
0
 0
0
 0
 0
20
10
60
—
—
—
50
100 
60
80


Velvetleaf
100 
—
—
—
—
—
—
—
—
—
80
100 
30
—
—
—
—


Wheat
40
80
0
40
0
10
30
20
20
40
20
 0
20
0
70
60
20












Postemergence



125 g ai/ha



Compounds

























121
122
125
126
127
128
129
130
131
132
134
135
136
137
138
140
141





Barnyardgrass
20
40
90
40
10
50
90
0
0
50
80
40
30
 0
80
70
100


Blackgrass
30
80
80
20
10
40
70
0
0
60
30
30
20
20
50
70
100


Corn
10
30
50
20
10
30
30
0
0
20
40
10
10
30
60
30
 60


Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
30
60
80
50
20
60
90
0
0
60
70
70
30
70
90
90
100


Galium
30
40
90
60
20
80
100
0
0
100 
100 
60
80
70
90
90
100


Kochia
40
90
40
100 
30
80
100
0
0
90
90
20
70
80
90
100 
100


Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Pigweed
40
100 
70
80
30
100 
100
0
0
100 
100 
70
80
70
100 
100 
100


Ragweed
40
30
10
50
10
20
80
0
0
10
50
60
50
20
30
70
100


Ryegrass, Italian
 0
20
10
10
 0
30
50
0
0
10
50
20
30
20
40
30
 80


Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Wheat
 0
10
20
10
 0
10
0
0
0
 0
 0
10
 0
30
50
 0
 80












Postemergence



125 g ai/ha



Compounds

























142
143
144
145
146
147
148
149
150
151
152
153
156
157
158
161
162





Barnyardgrass
0
0
90
70
10
90
30
70
100
60
30
0
10
80
80
0
0


Blackgrass
0
0
90
80
20
100
10
80
100
50
90
0
20
50
60
—
—


Corn
0
30
40
10
10
40
20
20
50
40
30
0
10
40
30
0
0


Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
0
0


Foxtail, Giant
0
0
100 
80
20
90
40
90
100
40
40
0
10
80
70
0
0


Galium
0
30
90
100 
50
100
60
100 
90
40
90
0
30
90
100 
—
—


Kochia
0
30
100 
60
70
100
30
70
70
90
80
0
40
100 
80
—
—


Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
0
0


Pigweed
0
70
100 
100 
100 
100
50
100 
100
70
90
0
20
100 
50
50 
30 


Ragweed
0
0
80
90
10
100
20
80
20
100 
20
0
40
50
80
—
—


Ryegrass, Italian
0
0
50
50
 0
70
 0
30
40
30
20
0
 0
20
50
—
—


Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
10 
10 


Wheat
0
0
20
40
 0
50
 0
 0
30
30
40
0
 0
 0
 0
0
0












Postemergence



125 g ai/ha



Compounds

























163
164
165
166
167
168
169
170
171
172
173
174
175
177
178
179
180





Barnyardgrass
30
70
0
90
70
50
20
70
0
30
0
0
0
40
70
80
90


Blackgrass
—
—
—
—
—
—
30
—
—
—
—
—
—
—
—
—
—


Corn
30
40
0
50
40
20
 0
80
0
0
0
0
0
40
30
30
70


Crabgrass, Large
30
80
0
90
80
70
—
70
0
20
0
0
0
80
90
90
90


Foxtail, Giant
50
90
10
90
90
70
40
70
0
0
10 
0
0
80
90
80
90


Galium
—
—
—
—
—
—
40
—
—
—
—
—
—
—
—
—
—


Kochia
—
—
—
—
—
—
10
—
—
—
—
—
—
—
—
—
—


Morningglory
90
80
10
100 
80
50
—
60
0
80
0
0
0
90
70
70
100 


Pigweed
100 
100 
30
100 
100 
100 
20
100 
100 
100
100 
0
0
100 
100 
100 
100 


Ragweed
—
—
—
—
—
—
60
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
 0
—
—
—
—
—
—
—
—
—
—


Velvetleaf
100 
100 
10
100 
100 
90
—
70
40 
90
60 
0
0
100 
100 
100 
100 


Wheat
10
70
0
60
20
10
 0
30
0
0
0
0
0
20
40
30
40












Postemergence



125 g ai/ha



Compounds

























181
182
183
184
185
186
187
188
189
190
191
192
194
195
196
197
198





Barnyardgrass
60
0
0
60
50
20
80
30
10
0
50
60
80
 0
10
20
30


Blackgrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
40
0
0
20
10
 0
10
20
10
0
20
10
30
 0
10
 0
20


Crabgrass, Large
70
0
0
70
60
40
60
50
30
10
50
50
90
40
30
30
60


Foxtail, Giant
70
0
0
70
50
20
60
60
40
0
50
70
90
10
30
20
30


Galium
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
90
0
0
60
70
60
70
40
50
30
80
80
90
30
20
 0
60


Pigweed
100 
30 
20 
100 
100 
100 
70
100 
100 
100
100 
100 
100 
60
100 
30
90


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
100 
30 
20 
80
90
80
100 
90
90
60
90
90
100 
50
100 
60
90


Wheat
 0
0
0
30
 0
 0
20
 0
20
0
20
 0
30
 0
 0
 0
 0












Postemergence



125 g ai/ha



Compounds

























199
200
201
202
203
204
205
206
208
209
210
211
212
213
214
215
218





Barnyardgrass
30
80
0
0
40
80
0
0
0
40
20
10
0
0
0
0
30


Blackgrass
—
—
—
—
—
—
—
—
—
—
—
—
10
—
—
—
—


Corn
20
50
0
0
30
50
0
0
0
30
10
 0
0
0
0
0
 0


Crabgrass, Large
40
90
0
10
60
90
0
0
0
70
40
10
—
20
0
10
50


Foxtail, Giant
70
90
0
10
70
80
0
0
0
70
30
30
0
10
0
0
20


Galium
—
—
—
—
—
—
—
—
—
—
—
—
10
—
—
—
—


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
0
—
—
—
—


Morningglory
40
90
20 
0
20
80
0
0
20 
50
20
90
—
20
0
10
70


Pigweed
80
100 
20 
30
70
100 
0
0
30 
100 
100 
90
20
100
0
70
90


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
0
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
20
—
—
—
—


Velvetleaf
70
100 
30 
50
80
100 
10 
10 
40 
100 
60
50
—
10
0
40
30


Wheat
 0
40
0
0
 0
40
0
0
0
 0
 0
 0
0
0
0
0
 0












Postemergence



125 g ai/ha



Compounds

























219
220
221
225
226
227
228
230
231
232
233
234
235
236
237
238
239





Barnyardgrass
50
90
50
0
0
0
10
0
40
30
0
20
0
100 
0
40
 0


Blackgrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
20
40
10
0
0
0
50
0
20
30
0
20
0
70
0
0
 0


Crabgrass, Large
90
100 
60
0
0
0
40
0
70
60
0
20
10
80
0
60
10


Foxtail, Giant
70
80
50
0
0
0
50
0
70
70
0
30
0
90
0
60
20


Galium
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
70
50
90
0
0
0
80
0
30
80
0
40
30
80
0
40
40


Pigweed
100 
100 
100 
0
0
10 
100 
30 
100 
100 
20 
100 
90
100 
30 
100
90


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
100 
100 
100 
0
0
50 
100 
0
100 
80
0
70
30
90
20 
60
50


Wheat
 0
10
 0
0
0
0
 0
0
20
20
0
20
0
50
0
0
 0












Postemergence



125 g ai/ha



Compounds

























240
241
242
243
244
245
246
247
249
250
251
252
253
254
258
259
260





Barnyardgrass
90
10
60
 0
10
30
0
20
60
60
30
100
100
60
90
30
0


Blackgrass
90
20
90
30
30
70
0
40
80
100
70
60
80
60
50
50
0


Corn
30
10
60
 0
20
40
20
20
10
30
20
60
60
20
40
10
10


Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
90
20
50
10
10
80
0
10
60
80
60
100
100
60
70
40
0


Galium
100
60
30
10
100
100 
70
30
30
60
30
90
100
100 
90
80
60


Kochia
100
90
80
30
80
100 
70
40
80
90
60
100
100
60
100 
80
60


Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Pigweed
100
80
80
20
100
90
40
20
100 
90
70
100
100
30
100 
90
60


Ragweed
100
30
50
20
0
20
0
 0
70
100
20
70
80
20
50
70
40


Ryegrass, Italian
40
 0
30
 0
0
20
0
 0
 0
0
10
40
50
20
20
10
0


Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Wheat
30
10
60
20
20
40
0
20
 0
0
 0
30
30
30
50
 0
0












Postemergence



125 g ai/ha



Compounds

























261
264
265
266
267
268
269
270
271
272
273
274
275
277
278
279
284





Barnyardgrass
0
0
0
0
0
0
0
80
80
0
70
90
0
40
0
30
30


Blackgrass
0
0
0
0
0
0
0
40
80
0
60
—
—
50
0
40
30


Corn
0
0
0
0
0
0
0
50
30
0
40
80
0
20
0
10
20


Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
90
0
—
—
—
—


Foxtail, Giant
10
0
0
0
0
0
0
90
90
0
70
90
0
70
0
50
90


Galium
50
0
0
0
10 
0
0
90
100 
0
80
—
—
100 
10 
80
20


Kochia
70
0
0
0
0
0
0
70
100 
0
70
—
—
70
0
90
60


Morningglory
—
—
—
—
—
—
—
—
—
—
—
90
10 
—
—
—
—


Pigweed
60
0
0
0
0
20 
0
100 
100 
0
100 
100 
80 
70
10 
80
100 


Ragweed
30
0
0
0
0
10 
0
20
80
0
40
—
—
60
10 
40
20


Ryegrass, Italian
0
0
0
0
0
0
0
30
30
0
50
—
—
50
0
50
20


Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
100 
60 
—
—
—
—


Wheat
0
0
0
0
0
0
0
30
40
0
10
70
0
 0
0
30
20












Postemergence



125 g ai/ha



Compounds





















285
287
288
289
290
291
292
293
294
295
296
301
304





Barnyardgrass
0
0
 0
0
0
0
60
10
20
0
0
0
0


Blackgrass
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
0
0
 0
0
0
0
50
 0
 0
0
0
0
0


Crabgrass, Large
10
10
10
0
0
10
60
20
 0
0
0
0
0


Foxtail, Giant
0
0
10
0
0
0
70
20
10
0
0
0
0


Galium
—
—
—
—
—
—
—
—
—
—
—
—
—


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
30
10
20
20 
0
30
90
10
20
40 
20 
0
0


Pigweed
80
30
90
100 
10 
30
100 
60
60
40 
30 
0
30 


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
30
10
20
10 
10 
50
70
60
50
30 
30 
0
0


Wheat
0
0
 0
0
0
0
10
 0
 0
0
0
0
0












Postemergence



31 g ai/ha



Compounds

























99
100
101
103
106
107
108
109
110
118
119
120
121
122
125
126
127





Barnyardgrass
100
0
20
0
0
0
20
10
10
30
40
20
0
10
0
10
0


Blackgrass
50
0
20
0
30
10
30
20
20
60
40
60
10
30
40
10
0


Corn
20
0
10
0
0
0
20
10
10
10
10
10
0
10
20
0
0


Foxtail, Giant
90
0
20
0
50
20
20
10
20
30
30
20
0
10
0
10
0


Galium
90
0
40
0
50
30
70
50
40
70
70
90
10
20
20
20
10


Kochia
100
0
70
0
0
0
70
40
90
60
70
60
20
50
40
40
0


Pigweed
100
0
90
0
50
40
50
70
100
70
70
60
10
70
30
50
20


Ragweed
30
0
50
0
20
30
20
10
10
70
30
30
10
10
0
10
0


Ryegrass, Italian
20
0
0
0
0
0
0
0
0
20
30
0
0
0
0
0
0


Wheat
50
0
20
0
0
10
10
0
0
20
10
0
0
0
0
0
0












Postemergence



31 g ai/ha



Compounds

























128
140
141
144
148
149
151
152
153
156
157
158
169
241
242
243
244





Barnyardgrass
10
30
60
20
0
20
0
0
0
0
10
20
0
0
0
0
0


Blackgrass
30
30
90
20
0
50
20
50
0
0
30
50
0
0
30
0
0


Corn
0
20
30
20
0
0
0
20
0
0
0
0
0
0
0
0
0


Foxtail, Giant
20
30
90
20
10
20
0
0
0
0
10
20
0
0
0
0
0


Galium
50
80
100
80
20
70
10
90
0
20
60
60
10
40
10
0
70


Kochia
50
90
100
50
0
60
60
20
0
0
60
60
0
50
30
20
20


Pigweed
80
90
100
80
50
60
20
0
0
10
90
40
10
40
30
10
20


Ragweed
0
60
80
20
10
50
50
20
0
0
20
60
10
10
20
20
0


Ryegrass, Italian
0
0
60
0
0
0
0
0
0
0
0
20
0
0
0
0
0


Wheat
0
0
10
20
0
0
20
20
0
0
0
0
0
0
0
0
0












Postemergence



31 g ai/ha



Compounds

























245
246
247
249
250
251
252
253
254
258
259
260
261
264
265
266
267





Barnyardgrass
0
0
0
0
10
10
20
20
10
10
0
0
0
0
0
0
0


Blackgrass
30
0
0
60
70
50
10
20
0
20
20
0
0
0
0
0
0


Corn
20
0
0
0
10
0
20
20
10
10
0
0
0
0
0
0
0


Foxtail, Giant
0
0
0
0
10
30
20
20
10
20
10
0
0
0
0
0
0


Galium
100
20
10
20
10
20
60
60
20
70
70
50
30
0
0
0
0


Kochia
60
20
20
20
60
40
70
100
20
90
60
50
50
0
0
0
0


Pigweed
0
20
10
60
60
60
80
90
10
80
70
50
30
0
0
0
0


Ragweed
0
0
0
10
50
10
20
20
10
10
50
30
20
0
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Wheat
20
0
0
0
0
0
20
20
0
0
0
0
0
0
0
0
0















Postemergence





31 g ai/ha





Compounds



















268
269
270
271
272
277
278
279






Barnyardgrass
0
0
10
10
0
20
0
0



Blackgrass
0
0
10
10
0
30
0
10



Corn
0
0
20
20
0
0
0
10



Foxtail, Giant
0
0
10
10
0
40
0
10



Galium
0
0
60
70
0
100
0
20



Kochia
0
0
60
70
0
60
0
40



Pigweed
0
0
60
70
0
60
0
50



Ragweed
0
0
0
0
0
50
0
20



Ryegrass, Italian
0
0
0
0
0
30
0
0



Wheat
0
0
0
0
0
0
0
0












Preemergence



1000 g ai/ha



Compounds

























12
13
14
53
54
55
56
65
66
67
69
70
102
114
115
116
123





Barnyardgrass
100
80
30
100
0
40
0
100
90
0
70
50
50 
90
100
 90
100


Corn
 0
0
 0
 10
20
0
20
 40
30
0
 0
 0
—
20
 60
 30
—


Crabgrass, Large
100
100
90
100
100
90
80
100
100 
20
90
90
—
100
100
100
—


Foxtail, Giant
100
100
90
100
100
90
30
100
100 
10
90
60
100 
100
100
100
100


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
0
—
—
—
100


Morningglory
 0
0
20
 60
70
0
0
100
40
0
10
10
—
10
 50
100
—


Pigweed
100
100
100 
100
100
90
100
100
100 
100
100 
90
20 
100
100
100
100


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
0
—
—
—
 90


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
0
—
—
—
 70


Velvetleaf
100
100
90
100
100
100
90
100
90
10
80
70
—
100
100
100
—


Wheat
 20
20
20
 0
0
0
0
 30
10
0
20
 0
—
40
 40
 40
—












Preemergence



1000 g ai/ha



Compounds

























139
154
155
159
160
193
207
216
217
222
223
224
229
248
255
256
257





Barnyardgrass
0
100
100
100
100
60
0
30
70
100
100
100
0
80
10
20
50


Corn
—
—
—
—
—
20
0
0
0
 60
 80
 40
0
—
—
—
—


Crabgrass, Large
—
—
—
—
—
100
50 
70
100
100
100
100
10 
—
—
—
—


Foxtail, Giant
0
100
100
100
100
100
50 
40
90
100
100
100
0
100 
10
30
70


Kochia
0
100
100
100
100
—
—
—
—
—
—
—
—
100 
70
70
70


Morningglory
—
—
—
—
—
100
0
0
40
100
100
 90
0
—
—
—
—


Pigweed
50 
100
100
100
100
100
0
100
100
100
100
100
100 
100 
60
30
80


Ragweed
0
100
 90
100
100
—
—
—
—
—
—
—
—
40
20
30
70


Ryegrass, Italian
0
 90
 60
 30
 90
—
—
—
—
—
—
—
—
50
20
20
20


Velvetleaf
—
—
—
—
—
90
30 
30
100
100
100
100
0
—
—
—
—


Wheat
—
—
—
—
—
20
0
0
0
 70
 80
 60
0
—
—
—
—












Preemergence










1000 g ai/ha
500 g ai/ha



Compounds
Compounds

























262
263
276
280
281
282
283
297
298
299
300
302
303
1
2
3
4





Barnyardgrass
0
0
0
100
 0
 90
0
10
100
 90
20
0
0
70
90
100
0


Corn
—
—
—
 50
—
—
—
 0
—
—
—
—
0
0
30
10
0


Crabgrass, Large
—
—
—
100
—
—
—
90
—
—
—
—
60 
100
100
100
0


Foxtail, Giant
50 
50 
0
100
 0
100
0
80
100
100
80
0
50 
100
100
100
0


Kochia
20 
20 
0
—
 0
100
0
—
 90
100
60
0
—
—
—
—
—


Morningglory
—
—
—
 0
—
—
—
 0
—
—
—
—
0
0
20
20
0


Pigweed
10 
10 
0
100
60
100
0
70
100
100
100 
0
80 
100
100
100
0


Ragweed
0
0
0
—
30
100
0
—
 90
 70
 0
0
—
—
—
—
—


Ryegrass, Italian
0
0
0
—
10
 50
0
—
 50
 60
20
0
—
—
—
—
—


Velvetleaf
—
—
—
100
—
—
—
50
—
—
—
—
0
20
70
90
0


Wheat
—
—
—
 40
—
—
—
 0
—
—
—
—
0
0
0
10
0












Preemergence



500 g ai/ha



Compounds

























5
6
7
8
9
10
11
15
16
17
18
19
20
21
22
23
24





Barnyardgrass
80
90
100
90
100
90
100
100
100
60
100
20
20
30
20
50
0


Corn
0
20
 30
0
20
20
 30
 0
 30
 0
10
0
0
0
 0
20
0


Crabgrass, Large
90
100
100
100
100
100
100
100
100
90
100
90
90
100
90
90
0


Foxtail, Giant
100
100
100
100
90
100
100
100
100
90
100
90
80
100
90
90
0


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
20
10
 70
30
0
60
 60
 0
 90
20
40
0
0
0
 0
0
0


Pigweed
100
100
100
100
100
100
100
100
100
100 
100
100
90
100
90
100
0


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
100
100
100
100
100
100
100
100
100
90
90
20
0
20
20
90
0


Wheat
20
30
 20
0
0
20
 0
 0
 60
70
70
0
0
0
 0
0
0












Preemergence



500 g ai/ha



Compounds

























25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41





Barnyardgrass
100
90
20
10
20
10
50
60
 70
50
 0
 0
10
0
10
50
50


Corn
30
10
 0
0
0
0
 0
 0
 0
0
 0
 0
0
0
0
 0
0


Crabgrass, Large
100
90
50
10
40
60
90
60
100
90
10
70
80
40
90
80
70


Foxtail, Giant
100
90
40
10
20
30
90
70
100
100
10
20
30
20
50
60
80


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
0
 0
 0
0
0
0
 0
 0
—
—
—
—
0
0
0
 0
0


Pigweed
90
90
20
40
0
0
60
40
100
100
20
20
0
0
0
50
100


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
90
80
10
0
40
40
90
70
100
80
20
20
10
10
20
70
70


Wheat
0
 0
 0
0
0
0
 0
 0
 0
0
 0
 0
0
0
0
 0
0












Preemergence



500 g ai/ha



Compounds

























42
43
44
45
46
47
48
49
50
51
52
57
58
59
60
61
62





Barnyardgrass
10
10
100
100
20
100
0
0
0
30
100
100
100
100
70
20 
100


Corn
 0
 0
 20
 20
0
 90
0
0
0
0
 80
 70
 70
 30
0
0
 90


Crabgrass, Large
30
50
100
100
100
100
80 
20 
40 
90
100
100
100
100
100
20 
100


Foxtail, Giant
20
20
100
100
80
100
50 
10 
0
80
100
100
100
100
90
0
100


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
 0
 0
 60
 10
0
100
0
0
0
0
100
 40
100
100
0
0
 90


Pigweed
20
20
100
100
90
100
0
0
0
80
100
100
100
100
100
30 
100


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
60
50
100
100
0
100
0
20 
0
0
100
100
100
100
40
0
100


Wheat
 0
 0
 20
 0
0
 40
0
0
0
0
 80
 50
 90
 40
0
0
 80












Preemergence



500 g ai/ha



Compounds

























63
64
68
71
72
73
74
75
76
77
78
79
80
81
82
83
84





Barnyardgrass
70
100 
0
100
100
100
100
70
100
90
80
100
100
70
30
 90
 90


Corn
0
70
—
 40
 50
 70
 40
10
 30
0
10
100
40
10
—
—
—


Crabgrass, Large
100
90
—
100
100
100
100
100
100
100
100 
100
100
100
—
—
—


Foxtail, Giant
100
90
0
100
100
100
100
100
100
100
100 
100
100
100
70
100
100


Kochia
—
—
0
—
—
—
—
—
—
—
—
—
—
—
 0
100
100


Morningglory
0
20
—
 90
100
100
100
30
 80
60
20
100
80
60
—
—
—


Pigweed
100
100 
30 
100
100
100
100
100
100
100
100 
100
0
0
60
100
100


Ragweed
—
—
0
—
—
—
—
—
—
—
—
—
—
—
 0
 50
 40


Ryegrass, Italian
—
—
0
—
—
—
—
—
—
—
—
—
—
—
 0
 60
 20


Velvetleaf
20
90
—
100
100
100
100
80
100
100
50
100
90
100
—
—
—


Wheat
0
30
—
 40
 60
 80
 40
0
 30
0
10
100
50
10
—
—
—












Preemergence



500 g ai/ha



Compounds

























85
86
87
88
89
90
91
92
93
94
95
96
97
98
111
112
113





Barnyardgrass
100
100
10
 80
90
100
 0
100
0
100
100
30
100
100
100
100
90


Corn
—
—
—
—
—
—
—
 40
0
 30
 40
0
 60
 10
 50
 50
20


Crabgrass, Large
—
—
—
—
—
—
—
100
30 
100
100
90
100
100
100
100
100 


Foxtail, Giant
100
100
70
100
90
100
30
100
0
100
100
60
100
100
100
100
90


Kochia
100
100
60
100
100 
100
90
—
—
—
—
—
—
—
—
—
—


Morningglory
—
—
—
—
—
—
—
100
0
 90
100
0
100
 80
100
 90
30


Pigweed
100
100
100 
100
100 
100
90
100
30 
100
100
100
100
100
100
100
100 


Ragweed
 60
100
20
 60
70
 80
 0
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
 40
 60
 0
 30
10
 30
30
—
—
—
—
—
—
—
—
—
—


Velvetleaf
—
—
—
—
—
—
—
100
0
100
100
10
100
100
100
100
50


Wheat
—
—
—
—
—
—
—
 80
0
 30
 10
0
 80
 50
 40
 50
30












Preemergence



500 g ai/ha



Compounds

























117
129
130
131
132
134
135
136
137
138
142
143
145
146
147
150
161





Barnyardgrass
 90
 90
0
0
100
100
 90
100
100
100
0
100
100
 90
100
100
10


Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
0


Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
0


Foxtail, Giant
100
100
0
0
100
100
100
100
100
100
0
100
100
100
100
100
0


Kochia
100
100
0
0
100
100
100
100
100
100
50 
100
100
100
100
100
—


Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
0


Pigweed
100
100
0
0
100
100
100
100
100
100
0
100
100
100
100
100
100


Ragweed
 60
 80
0
0
 10
 80
 90
100
 60
 60
20 
 20
 80
100
100
 70
—


Ryegrass, Italian
 30
 30
0
0
 40
 40
 20
 30
 20
 50
0
 20
 50
 50
100
 50
—


Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
20


Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
0












Preemergence



500 g ai/ha



Compounds

























162
163
164
165
166
167
168
170
171
172
173
174
175
176
177
178
179





Barnyardgrass
50
100
100
20
100
100
80
100
60 
0
30
0
0
60
100
100
100


Corn
0
 10
 60
 0
 30
 40
20
20
0
0
0
0
0
0
 50
 30
10


Crabgrass, Large
10
100
100
90
100
100
100 
100
0
30 
80
0
0
100
100
100
100


Foxtail, Giant
0
100
100
90
100
100
100 
90
0
0
70
0
0
100
100
100
100


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
0
 70
100
—
100
100
80
90
0
0
0
0
0
0
 80
 90
80


Pigweed
100
100
100
90
100
100
100 
100
100 
50 
100
0
0
100
100
100
100


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
50
100
100
20
100
100
90
100
70 
0
0
0
0
90
100
100
80


Wheat
0
 10
 90
 0
 80
 50
20
20
0
0
0
0
0
0
 50
 40
30












Preemergence



500 g ai/ha



Compounds

























180
181
182
183
184
185
186
187
188
189
190
191
192
194
195
196
197





Barnyardgrass
100
100
20
0
100
80
100
100
100
90
10
100
100
100
 0
40
70


Corn
 90
30
0
0
20
10
 0
 40
 20
0
 0
30
 50
 50
 0
0
 0


Crabgrass, Large
100
100
30
0
100
100 
100
100
100
100
90
100
100
100
70
100
90


Foxtail, Giant
100
100
20
0
100
100 
100
100
100
100
80
100
100
100
80
90
80


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
100
30
0
0
90
30
 20
 50
 90
30
20
70
100
100
10
0
 0


Pigweed
100
100
100
90 
100
100 
100
100
100
100
100 
100
100
100
40
100
70


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
100
40
0
0
60
80
100
100
100
80
60
90
100
100
20
40
30


Wheat
 80
10
0
0
30
10
 20
 40
 30
10
 0
40
—
 30
 0
0
 0












Preemergence



500 g ai/ha



Compounds

























198
199
200
201
202
203
204
205
206
208
209
210
211
212
213
214
215





Barnyardgrass
80
80
 90
0
10 
40
100
0
0
70
100
70
60
20
10
0
10


Corn
0
0
 50
0
0
0
 30
0
0
 0
20
0
0
—
0
0
0


Crabgrass, Large
100
100
100
40 
70 
100
100
0
0
100 
100
100
100
—
100
0
80


Foxtail, Giant
100
100
100
50 
70 
100
100
0
0
90
100
100
100
50
100
0
50


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
40
—
—
—


Morningglory
10
20
100
0
0
10
 90
0
0
30
70
0
70
—
10
0
0


Pigweed
100
100
100
0
0
100
100
10 
50 
100 
100
100
100
90
100
0
100


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
 0
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
20
—
—
—


Velvetleaf
80
90
100
0
0
40
100
10 
0
50
90
60
90
—
0
0
10


Wheat
0
0
 50
0
0
0
 60
0
0
20
20
0
0
—
0
0
0












Preemergence



500 g ai/ha



Compounds

























218
219
220
221
225
226
227
228
230
231
232
233
234
235
236
237
238





Barnyardgrass
70
90
100
90
0
0
0
100
0
100
100
0
100
10
100
10
100


Corn
0
10
10
0
0
0
0
40
0
 20
60
0
 90
0
 90
0
 90


Crabgrass, Large
100
100
100
100
0
0
10
100
0
100
100
10 
100
100
100
10
100


Foxtail, Giant
100
100
100
100
0
0
10
100
0
100
90
0
 90
100
100
0
100


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
10
10
40
10
0
0
0
80
0
 30
90
0
100
0
100
0
100


Pigweed
100
100
100
100
0
0
60
0
70 
100
100
20 
100
100
100
80
100


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
50
20
70
70
0
0
20
100
0
100
100
0
100
0
100
10
 90


Wheat
0
0
20
10
0
0
0
0
0
 20
10
0
 0
0
100
0
 30












Preemergence



500 g ai/ha



Compounds

























239
240
252
273
274
275
284
285
287
288
289
290
291
292
293
294
295





Barnyardgrass
100
100
100
90
100
0
90
30
0
10
20
0
50
100
10
20
0


Corn
10
—
—
—
 50
0
—
20
0
0
0
0
 0
 30
0
0
0


Crabgrass, Large
100
—
—
—
100
70
—
100 
70 
10
10
10 
90
100
90
60
0


Foxtail, Giant
100
100
100
90
100
70
90
100 
40 
0
10
10 
80
100
90
70
0


Kochia
—
100
100
100 
—
—
100 
—
—
—
—
—
—
—
—
—
—


Morningglory
30
—
—
—
100
0
—
40
0
0
0
0
 0
 90
0
0
0


Pigweed
100
100
100
100 
100
90
100 
100 
100 
90
100
0
90
100
80
100
60 


Ragweed
—
100
100
80
—
—
 0
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
 70
 90
40
—
—
20
—
—
—
—
—
—
—
—
—
—


Velvetleaf
20
—
—
—
100
60
—
40
0
10
10
0
60
100
0
70
0


Wheat
20
—
—
—
 80
0
—
20
0
0
0
0
 0
 30
0
0
0












Preemergence










500 g ai/ha
125 g ai/ha



Compounds
Compounds

























296
301
304
1
2
3
4
5
6
7
8
9
10
11
15
16
17





Barnyardgrass
10
0
0
20
30
60
0
10
20
80
50
30
60
70
20
100
50


Corn
 0
0
0
0
 0
 0
0
0
0
0
0
0
0
 0
 0
 10
0


Crabgrass, Large
60
0
10 
50
80
90
0
90
90
100
80
90
100
90
40
100
40


Foxtail, Giant
10
0
0
60
80
90
0
90
90
100
70
80
90
90
30
100
60


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
 0
0
0
0
—
 0
0
0
0
20
20
0
40
30
 0
 30
0


Pigweed
90
0
0
60
90
90
0
100
100
90
90
100
100
90
90
100
100


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
10
0
0
0
30
70
0
90
100
100
100
80
100
90
60
100
70


Wheat
 0
0
0
0
 0
 0
0
0
0
0
0
0
0
 0
 0
 20
0












Preemergence



125 g ai/ha



Compounds

























18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34





Barnyardgrass
90
0
0
20
0
20
0
90
30
0
0
0
0
20
0
0
 0


Corn
0
0
0
0
0
0
0
 0
 0
0
0
0
0
 0
0
0
 0


Crabgrass, Large
100
0
20 
90
20 
90
0
90
70
0
0
10 
40 
50
0
90
70


Foxtail, Giant
100
20 
20 
70
20 
70
0
80
60
0
0
10 
0
20
0
90
30


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
0
0
0
0
0
0
0
 0
 0
0
0
0
0
 0
0
—
—


Pigweed
100
0
30 
90
20 
100
0
90
80
10 
0
0
0
40
0
100
80


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
90
0
0
0
0
90
0
—
60
0
0
0
10 
50
10 
50
60


Wheat
0
0
0
0
0
0
0
 0
 0
0
0
0
0
 0
0
0
 0












Preemergence



125 g ai/ha



Compounds

























35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51





Barnyardgrass
0
0
0
0
0
40
10
0
0
50
30
0
20
0
0
0
20


Corn
0
0
0
0
0
0
 0
0
0
0
0
0
0
0
0
0
0


Crabgrass, Large
0
0
10 
0
10 
60
30
10 
10 
90
90
20 
90
50 
0
0
40


Foxtail, Giant
0
0
10 
0
10 
10
10
10 
10 
60
90
0
100
10 
0
0
20


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
—
—
0
0
0
0
 0
0
0
50
0
0
0
0
0
0
0


Pigweed
0
0
0
0
0
0
70
0
0
100
100
20 
100
0
0
0
10


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
0
0
10 
0
10 
50
60
60 
30 
70
100
0
100
0
0
0
0


Wheat
0
0
0
0
0
0
 0
0
0
0
0
0
0
0
0
0
0












Preemergence



125 g ai/ha



Compounds

























52
57
58
59
60
61
62
63
64
71
72
73
74
75
76
77
79





Barnyardgrass
90
60
100
80
0
0
60
0
60
60
80
90
70
20
50
50
100


Corn
20
0
 40
20
0
0
0
0
 0
30
30
20
0
0
20
0
 80


Crabgrass, Large
100
90
100
100
40 
0
90
80 
90
100 
100 
100
100
70
100
90
100


Foxtail, Giant
100
80
100
100
20 
0
90
20 
90
100 
100 
100
90
40
80
90
100


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
90
0
100
80
0
0
0
0
 0
90
80
90
70
20
0
10
100


Pigweed
100
100
100
100
30 
0
100
90 
90
100 
100 
100
100
100
100
100
100


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
100
40
 90
100
0
0
50
0
40
70
90
100
70
40
90
60
100


Wheat
20
0
 60
20
0
0
0
0
 0
20
20
0
0
0
0
0
 70












Preemergence



125 g ai/ha



Compounds

























80
81
82
83
84
85
86
87
88
89
90
91
92
93
94
95
96





Barnyardgrass
60
0
0
 60
50
20
 80
 0
 60
60
70
 0
60
0
80
50
0


Corn
 0
0
—
—
—
—
—
—
—
—
—
—
10
0
0
0
0


Crabgrass, Large
100 
90
—
—
—
—
—
—
—
—
—
—
100
0
100
100
30 


Foxtail, Giant
90
80
10 
100
70
100 
100
60
100
90
90
10
100
0
100
100
10 


Kochia
—
—
0
100
100
80
100
30
100
90
100 
30
—
—
—
—
—


Morningglory
30
0
—
—
—
—
—
—
—
—
—
—
90
0
40
50
0


Pigweed
 0
0
0
100
100
100 
100
90
100
90
100 
70
100
0
100
90
50 


Ragweed
—
—
0
 20
10
40
 90
10
—
50
50
 0
—
—
—
—
—


Ryegrass, Italian
—
—
0
 50
0
 0
 10
 0
 20
 0
 0
 0
—
—
—
—
—


Velvetleaf
80
50
—
—
—
—
—
—
—
—
—
—
100
0
90
90
0


Wheat
10
10
—
—
—
—
—
—
—
—
—
—
0
0
0
0
0












Preemergence



125 g ai/ha



Compounds

























97
98
99
100
101
103
106
107
108
109
110
111
112
113
117
118
119





Barnyardgrass
 80
50
 90
0
70
0
40
60
70
60
90
90
70
0
30
100
 90


Corn
 40
0
—
—
—
—
—
—
—
—
—
20
0
0
—
—
—


Crabgrass, Large
100
100
—
—
—
—
—
—
—
—
—
100
100
80
—
—
—


Foxtail, Giant
100
100
100
0
90
0
70
80
90
90
100 
100
100
20
90
100
100


Kochia
—
—
100
0
70
0
 0
 0
70
60
80
—
—
—
70
100
100


Morningglory
100
60
—
—
—
—
—
—
—
—
—
90
80
0
—
—
—


Pigweed
100
100
100
0
100 
0
60
50
100 
100 
100 
100
100
100
100 
100
100


Ragweed
—
—
 90
0
30
0
 0
 0
80
10
10
—
—
—
20
 90
 60


Ryegrass, Italian
—
—
 30
0
 0
0
 0
 0
30
 0
20
—
—
—
20
 50
 80


Velvetleaf
100
90
—
—
—
—
—
—
—
—
—
70
90
10
—
—
—


Wheat
 0
0
—
—
—
—
—
—
—
—
—
0
0
0
—
—
—












Preemergence



125 g ai/ha



Compounds

























120
121
122
125
126
127
128
129
130
131
132
134
135
136
137
138
140





Barnyardgrass
70
30
 70
80
80
40
70
 70
0
0
50
 70
40
60
20
80
 70


Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
100 
50
100
100 
100 
60
100
100
0
0
90
100
70
60
90
90
100


Kochia
90
60
100
50
90
 0
70
100
0
0
100 
100
100 
90
90
90
100


Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Pigweed
100 
90
100
100 
100 
10
100
100
0
0
100 
100
100 
90
90
90
100


Ragweed
 0
10
 0
10
20
 0
0
 30
0
0
 0
 60
90
80
30
30
 70


Ryegrass, Italian
30
 0
 0
20
 0
 0
10
 10
0
0
30
 20
 0
 0
 0
 0
 0


Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—












Preemergence



125 g ai/ha



Compounds

























141
142
143
144
145
146
147
148
149
150
151
152
153
156
157
158
161





Barnyardgrass
100
0
30
 90
50
20
100
50
 90
 90
60
70
0
30
80
70
0


Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
0


Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
0


Foxtail, Giant
100
0
80
100
80
70
100
70
100
100
100 
100 
0
70
100 
90
0


Kochia
100
0
50
100
90
40
100
 0
100
100
90
90
0
10
90
70
—


Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
0


Pigweed
100
0
90
100
100 
60
100
10
100
100
90
90
0
 0
90
70
90 


Ragweed
100
0
 0
100
50
 0
 90
 0
 60
 30
80
40
0
 0
30
80
—


Ryegrass, Italian
 80
0
 0
 20
10
 0
 10
 0
 20
 20
 0
 0
0
 0
 0
50
—


Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
10 


Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
0












Preemergence



125 g ai/ha



Compounds

























162
163
164
165
166
167
168
169
170
171
172
173
174
175
177
178
179





Barnyardgrass
10 
50
90
0
 90
80
50
50
90
20 
0
0
0
0
70
90
20


Corn
0
0
10
0
 30
10
0
—
0
0
0
0
0
0
0
0
0


Crabgrass, Large
0
100
100
50
100
100
100
—
100
0
0
20 
0
0
100
100
100


Foxtail, Giant
0
100
90
20
100
100
100
80
100
0
0
50 
0
0
100
100
100


Kochia
—
—
—
—
—
—
—
 0
—
—
—
—
—
—
—
—
—


Morningglory
0
0
80
0
100
90
20
—
20
0
0
0
0
0
20
10
10


Pigweed
100 
100
100
60
100
100
100
80
100
90 
0
80 
0
0
100
100
100


Ragweed
—
—
—
—
—
—
—
 0
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
 0
—
—
—
—
—
—
—
—
—


Velvetleaf
10 
20
100
10
100
80
70
—
80
30 
0
0
0
0
80
80
60


Wheat
0
0
20
0
 50
0
20
—
20
0
0
0
0
0
0
0
0












Preemergence



125 g ai/ha



Compounds

























180
181
182
183
184
185
186
187
188
189
190
191
192
194
195
196
197





Barnyardgrass
100
50
0
0
30
40
30
80
30
20
0
70
60
80
0
0
30


Corn
 60
0
0
0
20
0
0
0
 0
0
0
0
0
30
0
0
0


Crabgrass, Large
100
100
0
0
100
90
100
100
90
90
20
100
100
100 
—
60
40


Foxtail, Giant
100
90
0
0
100
90
80
100
90
70
10
100
100
100 
10 
50
20


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
 90
0
0
0
0
10
0
0
10
0
0
50
30
60
0
0
0


Pigweed
100
100
90 
20 
100
100
100
100
100 
100
100
100
100
100 
0
90
50


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
100
20
0
0
20
40
70
80
70
60
50
80
90
80
0
20
0


Wheat
 20
0
0
0
0
0
0
0
 0
0
0
20
0
20
0
0
0












Preemergence



125 g ai/ha



Compounds

























198
199
200
201
202
203
204
205
206
208
209
210
211
212
213
214
215





Barnyardgrass
50
20
80
0
0
10
70
0
0
0
60
10
0
0
0
0
0


Corn
0
0
40
0
0
0
0
0
0
0
0
0
0
—
0
0
0


Crabgrass, Large
80
100
100
20 
40 
100
100
0
0
20 
100
100
80
—
10 
0
20 


Foxtail, Giant
70
90
100
20 
10 
90
100
0
0
20 
100
100
100
0
20 
0
0


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
0
—
—
—


Morningglory
0
0
90
0
0
0
90
0
0
0
10
0
20
—
0
0
0


Pigweed
100
90
100
0
0
90
100
0
0
30 
100
100
90
70 
50 
0
90 


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
0
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
0
—
—
—


Velvetleaf
40
20
100
0
0
30
80
0
0
0
90
20
60
—
0
0
0


Wheat
0
0
30
0
0
0
40
0
0
0
0
0
0
—
0
0
0












Preemergence



125 g ai/ha



Compounds

























218
219
220
221
225
226
227
228
230
231
232
233
234
235
236
237
238





Barnyardgrass
10
30
60
10
0
0
0
20
0
20
60
0
20
0
100
0
70


Corn
0
0
0
0
0
0
0
 0
0
0
0
0
 0
0
 20
0
0


Crabgrass, Large
80
100
100
100
0
0
0
90
0
90
90
0
90
70 
100
0
100


Foxtail, Giant
20
100
100
100
0
0
0
90
0
90
90
0
60
30 
100
0
100


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
0
0
0
0
0
0
0
10
0
0
20
0
 0
0
 30
0
10


Pigweed
100
100
100
100
0
0
10 
 0
0
90
100
0
90
90 
100
0
100


Ragweed
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
10
10
20
10
0
0
10 
70
0
0
20
0
40
0
100
0
70


Wheat
0
0
0
0
0
0
0
 0
0
0
0
0
 0
0
 0
0
0












Preemergence



125 g ai/ha



Compounds

























239
240
241
242
243
244
245
246
247
249
250
251
252
253
254
258
259





Barnyardgrass
20
90
 60
 70
30
20
70
30
70
 0
 90
50
100
100
80
90
70


Corn
0
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Crabgrass, Large
100
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
90
100
100
100
100 
80
100 
70
100 
 0
100
80
100
100
90
100 
100 


Kochia
—
100
100
100
90
40
30
 0
60
40
 0
70
100
100
80
90
80


Morningglory
0
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Pigweed
100
100
100
100
80
100 
90
20
80
90
100
90
100
100
90
100 
100 


Ragweed
—
 90
 40
 80
20
 0
 0
 0
 0
 0
—
30
 70
 80
 0
40
70


Ryegrass, Italian
—
 20
 0
 0
 0
 0
 0
 0
 0
30
 0
 0
 20
 20
40
10
 0


Velvetleaf
10
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Wheat
0
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—












Preemergence



125 g ai/ha



Compounds

























260
261
264
265
266
267
268
269
270
271
272
273
274
275
277
278
279





Barnyardgrass
0
0
0
0
0
0
0
0
100
100
0
70
 90
0
0
0
10


Corn
—
—
—
—
—
—
—
—
—
—
—
—
 50
0
—
—
—


Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
100
0
—
—
—


Foxtail, Giant
0
0
0
0
0
0
0
0
100
100
0
90
100
0
70 
0
50


Kochia
0
0
0
0
0
0
0
0
100
100
0
100 
—
—
0
0
90


Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
100
0
—
—
—


Pigweed
30 
0
0
0
0
0
0
0
100
100
0
100 
100
80 
60 
10 
100 


Ragweed
0
0
0
0
0
0
0
0
 20
 20
0
70
—
—
0
0
10


Ryegrass, Italian
0
0
0
0
0
0
0
0
 10
 10
0
20
—
—
0
0
 0


Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
100
20 
—
—
—


Wheat
—
—
—
—
—
—
—
—
—
—
—
—
 40
0
—
—
—












Preemergence



125 g ai/ha



Compounds






















284
285
287
288
289
290
291
292
293
294
295
296
301
304





Barnyardgrass
60
0
0
0
0
0
0
80
0
0
0
0
0
0


Corn
—
0
0
0
0
0
0
20
0
0
0
0
0
0


Crabgrass, Large
—
80
0
0
0
0
50
100 
40 
30
0
0
0
0


Foxtail, Giant
90
20
0
0
0
0
20
100 
20 
30
0
0
0
0


Kochia
80
—
—
—
—
—
—
—
—
—
—
—
—
—


Morningglory
—
0
0
0
0
0
0
30
0
0
0
0
0
0


Pigweed
100 
80
0
20 
20 
0
60
100 
20 
100
20 
0
0
0


Ragweed
 0
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
20
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
—
10
0
0
0
0
40
30
0
10
0
0
0
0


Wheat
—
0
0
0
0
0
0
10
0
0
0
0
0
0












Preemergence



31 g ai/ha



Compounds

























99
100
101
103
106
107
108
109
110
118
119
120
121
122
125
126
127





Barnyardgrass
80
0
60
0
0
10
10
20
30
50
30
20
0
10
10
10
0


Foxtail, Giant
100
0
70
0
30
30
20
70
100
80
90
50
10
50
20
50
10


Kochia
100
0
70
0
0
0
40
20
20
100
50
20
0
20
20
40
0


Pigweed
100
0
90
0
10
0
90
100
100
100
100
100
60
80
70
80
0


Ragweed
70
0
0
0
0
0
70
0
0
50
0
0
0
0
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
0
10
0
0
0
0
0
0












Preemergence



31 g ai/ha



Compounds

























128
140
141
144
148
149
151
152
153
156
157
158
169
241
242
243
244





Barnyardgrass
10
30
90
20
0
40
20
20
0
0
20
10
10
10
20
0
0


Foxtail, Giant
60
50
100
70
10
60
100
10
0
0
70
60
30
50
100
0
0


Kochia
0
60
100
70
0
70
80
20
0
0
60
50
0
50
30
0
0


Pigweed
100
90
100
90
0
100
90
90
0
0
90
50
0
80
90
0
0


Ragweed
0
30
90
0
0
0
20
20
0
0
—
40
0
0
50
0
0


Ryegrass, Italian
0
0
30
20
0
0
0
0
0
0
0
30
0
0
0
0
0












Preemergence



31 g ai/ha



Compounds

























245
246
247
249
250
251
252
253
254
258
259
260
261
264
265
266
267





Barnyardgrass
0
0
0
0
10
30
70
50
20
50
10
0
0
0
0
0
0


Foxtail, Giant
60
0
0
0
30
50
70
70
30
60
30
0
0
0
0
0
0


Kochia
0
0
0
0
90
10
80
90
20
90
20
0
0
0
0
0
0


Pigweed
90
0
0
90
80
70
100
100
30
100
70
0
0
0
0
0
0


Ragweed
0
0
0
0
—
0
20
20
0
0
10
0
0
0
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
20
20
0
0
0
0
0
0
0
0
0














Preemergence




31 g ai/ha




Compounds


















268
269
270
271
272
277
278
279






Barnyardgrass
0
0
20
20
0
0
0
0



Foxtail, Giant
0
0
40
40
0
30
0
40



Kochia
0
0
80
70
0
0
0
40



Pigweed
0
0
100
90
0
30
0
90



Ragweed
0
0
0
0
0
0
0
0



Ryegrass, Italian
0
0
0
0
0
0
0
0









Test B

Plant species in the flooded paddy test selected from rice (Oryza sativa), sedge, umbrella (small-flower umbrella sedge, Cyperus difformis), (Heteranthera limosa), and barnyardgrass (Echinochloa crus-galli) were grown to the 2-leaf stage for testing. At time of treatment, test pots were flooded to 3 cm above the soil surface, treated by application of test compounds directly to the paddy water, and then maintained at that water depth for the duration of the test. Treated plants and controls were maintained in a greenhouse for 13 to 15 days, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table B, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.









TABLE B









Compounds





















250 g ai/ha
1
2
3
4
5
6
7
8
9
10
11
13
15
16










Flood





















Barnyardgrass
0
0
0
0
0
0
30
0
0
0
0
0
20
40


Ducksalad
0
45
90
0
50
65
80
100
80
75
50
30
75
90


Rice
0
0
0
0
10
15
20
30
0
0
0
0
20
40


Sedge, Umbrella
0
0
75
0
50
55
75
80
60
50
0
0
85
90












Compounds





















250 g ai/ha
17
18
19
20
21
22
23
24
25
26
27
28
29
30










Flood





















Barnyardgrass
0
30
0
20
25
20
20
0
20
0
0
0
0
0


Ducksalad
75
90
40
60
40
65
80
0
85
80
75
35
0
0


Rice
25
0
20
45
15
40
35
35
20
25
0
0
0
0


Sedge, Umbrella
90
90
30
75
70
80
70
60
85
80
75
0
0
0












Compounds





















250 g ai/ha
31
32
33
34
35
36
37
38
39
40
39 41
42
43
44










Flood





















Barnyardgrass
0
0
10
20
0
0
0
0
0
20
0
0
0
20


Ducksalad
80
0
80
90
0
0
0
0
50
80
70
45
75
100


Rice
25
15
0
30
0
0
0
0
0
15
0
15
0
45


Sedge, Umbrella
30
0
20
90
0
0
0
30
30
80
70
0
0
90












Compounds





















250 g ai/ha
45
46
47
48
49
50
51
52
53
54
57
58
59
60










Flood





















Barnyardgrass
30
0
10
0
0
0
0
30
0
0
0
80
40
0


Ducksalad
85
0
95
0
0
0
40
70
75
0
60
90
80
0


Rice
0
0
35
0
0
0
0
20
0
0
0
50
20
0


Sedge, Umbrella
75
0
70
0
0
0
65
95
0
0
80
90
90
0












Compounds





















250 g ai/ha
61
62
63
64
65
66
69
71
72
73
74
75
76
77










Flood





















Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ducksalad
0
80
0
70
95
30
0
0
75
70
40
60
70
40


Rice
0
0
0
0
0
0
0
30
0
0
0
0
0
20


Sedge, Umbrella
0
80
0
80
95
0
0
70
85
85
70
50
75
70












Compounds





















250 g ai/ha
79
80
81
82
83
84
85
86
87
88
89
90
91
92










Flood





















Barnyardgrass
40
0
0
0
0
0
0
0
0
0
10
0
0
20


Ducksalad
95
100
90
30
45
50
30
75
0
25
95
40
0
95


Rice
45
0
0
0
0
0
10
0
0
0
20
0
0
20


Sedge, Umbrella
95
80
80
0
45
30
30
65
0
0
85
40
0
90












Compounds





















250 g ai/ha
93
94
95
96
97
98
99
100
101
103
106
107
108
109










Flood





















Barnyardgrass
0
0
0
0
40
35
0
15
0
0
0
30
0
0


Ducksalad
0
40
40
0
95
85
0
0
0
0
75
40
85
80


Rice
0
0
0
0
0
15
0
0
0
0
0
0
35
0


Sedge, Umbrella
0
30
50
0
90
85
0
0
0
0
90
70
80
85












Compounds





















250 g ai/ha
110
111
112
113
114
115
116
117
118
119
120
121
122
123










Flood





















Barnyardgrass
45
0
0
0
0
0
0
0
50
40
0
20
0
35


Ducksalad
95
70
90
0
50
70
60
40
90
95
95
45
80
80


Rice
0
0
0
0
0
0
0
0
60
25
0
0
0
0


Sedge, Umbrella
95
75
85
0
30
20
30
20
95
95
95
0
75
40












Compounds





















250 g ai/ha
125
126
127
128
129
130
131
132
134
135
136
137
138
140










Flood





















Barnyardgrass
0
0
0
0
0
0
0
0
0
30
20
0
0
20


Ducksalad
70
65
60
85
65
0
0
0
30
70
70
30
90
80


Rice
0
0
0
0
0
0
0
0
0
0
15
0
0
0


Sedge, Umbrella
70
20
0
85
65
0
0
0
30
75
70
0
75
80












Compounds





















250 g ai/ha
141
142
143
144
145
146
147
148
149
150
151
152
153
154










Flood





















Barnyardgrass
100
0
0
0
20
20
35
0
0
0
0
0
0
20


Ducksalad
100
0
40
95
75
40
80
40
70
90
70
60
30
80


Rice
45
0
0
0
20
0
35
0
0
0
20
0
0
10


Sedge, Umbrella
90
0
0
80
65
40
75
30
65
85
0
50
0
30












Compounds





















250 g ai/ha
155
156
157
158
159
160
161
162
163
164
165
166
167
168










Flood





















Barnyardgrass
40
0
35
0
0
35
0
0
0
20
0
60
35
0


Ducksalad
100
0
80
50
0
80
0
35
90
100
0
95
100
90


Rice
50
0
35
40
0
35
0
0
25
0
0
75
0
30


Sedge, Umbrella
80
0
75
0
0
75
0
40
90
90
0
95
98
80












Compounds





















250 g ai/ha
169
170
171
172
173
174
175
177
178
179
180
181
182
183










Flood





















Barnyardgrass
25
70
0
0
0
0
0
30
0
20
60
0
0
0


Ducksalad
65
95
0
0
0
0
0
90
0
80
80
75
0
0


Rice
15
50
0
0
0
0
0
15
0
0
40
0
0
0


Sedge, Umbrella
75
90
0
0
0
0
0
100
0
85
80
85
0
0












Compounds





















250 g ai/ha
184
185
186
187
188
189
190
191
192
193
194
195
196
197










Flood





















Barnyardgrass
0
0
0
0
30
0
0
40
0
0
0
0
20
0


Ducksalad
100
95
0
65
90
70
0
95
90
0
98
20
85
0


Rice
10
0
0
0
0
0
0
0
0
0
0
20
0
0


Sedge, Umbrella
95
90
0
50
90
70
0
95
85
0
95
30
70
65












Compounds





















250 g ai/ha
198
199
200
201
202
203
204
205
206
208
209
210
211
212










Flood





















Barnyardgrass
0
0
20
0
0
0
20
0
0
0
30
0
0
0


Ducksalad
25
70
95
40
30
90
70
0
0
0
75
75
0
0


Rice
0
20
20
0
0
10
20
0
0
0
0
15
0
0


Sedge, Umbrella
20
70
85
20
10
90
90
0
0
0
60
60
0
0












Compounds





















250 g ai/ha
213
214
215
216
217
218
219
220
221
222
223
225
226
227










Flood





















Barnyardgrass
0
0
0
0
0
0
0
0
0
0
35
0
0
0


Ducksalad
0
0
0
0
0
50
100
100
0
50
90
0
0
0


Rice
0
0
0
0
0
0
0
0
0
0
50
0
0
0


Sedge, Umbrella
70
0
0
0
0
40
85
90
0
70
85
0
0
0












Compounds





















250 g ai/ha
228
230
231
232
233
234
235
236
237
238
239
240
241
242










Flood





















Barnyardgrass
0
20
20
10
10
20
0
30
0
0
0
0
0
20


Ducksalad
75
20
80
95
50
90
0
100
0
70
65
50
40
70


Rice
0
35
30
35
20
20
0
0
0
0
30
0
0
0


Sedge, Umbrella
60
50
80
80
50
90
0
100
0
90
70
30
0
75












Compounds





















250 g ai/ha
243
244
245
246
247
248
249
250
251
252
253
254
258
259










Flood





















Barnyardgrass
0
0
0
0
0
0
0
0
0
40
40
0
60
0


Ducksalad
30
40
75
0
65
50
70
70
75
75
75
65
100
70


Rice
0
0
0
0
0
15
0
0
0
0
25
0
30
0


Sedge, Umbrella
0
0
60
0
50
70
60
35
40
80
85
60
95
75












Compounds





















250 g ai/ha
260
261
264
265
266
267
268
269
270
271
272
273
274
275










Flood





















Barnyardgrass
0
0
0
0
0
0
0
0
35
0
0
0
65
15


Ducksalad
0
0
0
0
0
0
0
0
100
90
0
75
95
30


Rice
0
0
0
0
0
0
0
0
0
0
0
0
60
15


Sedge, Umbrella
0
0
0
0
0
0
50
0
90
60
0
75
95
0












Compounds





















250 g ai/ha
277
278
279
280
282
284
285
287
288
289
290
291
292
293










Flood





















Barnyardgrass
0
0
75
10
0
0
0
0
0
0
0
0
20
0


Ducksalad
80
0
90
30
0
80
0
0
0
0
0
0
45
80


Rice
0
0
50
10
0
0
0
0
0
0
0
0
20
0


Sedge, Umbrella
80
0
90
10
0
85
0
0
0
0
0
0
75
80













Compounds


















250 g ai/ha
294
295
296
297
298
299
301
304











Flood

















Barnyardgrass
0
0
0
0
0
20
0
0



Ducksalad
0
0
0
0
0
20
0
0



Rice
0
0
0
0
0
15
0
0



Sedge, Umbrella
0
0
0
0
30
70
0
0










Test C

Seeds of plant species selected from blackgrass (Alopecurus myosuroides), Italian ryegrass (Lolium multiflorum), wheat, winter (winter wheat, Triticum aestivum), galium (catchweed bedstraw, Galium aparine), corn (Zea mays), large (Lg) crabgrass (Digitaria sanguinalis), giant foxtail (Setaria faberii), johnsongrass (Sorghum halepense), lambsquarters (Chenopodium album), morningglory (Ipomoea coccinea), yellow nutsedge (Cyperus esculentus), pigweed (Amaranthus retroflexus), ragweed (common ragweed, Ambrosia elatior), soybean (Glycine max), barnyardgrass (Echinochloa crus-galli), oilseed rape (Brassica napus), waterhemp (common waterhemp, Amaranthus rudis), kochia (Kochia scoparia), wild oat (Avena fatua), surinam grass (Brachiaria decumbens), foxtail, green (green foxtail, Setaria viridis), goosegrass (Eleusine indica), bromegrass, downy (downy bromegrass, Bromus tectorum), nightshade (eastern black nightshade, Solanum ptycanthum), cocklebur (common cocklebur, Xanthium strumarium), cupgrass, woolly (woolly cupgrass, Eriochloa villosa), bermudagrass (Cynodon dactylon), sunflower, (common oilseed sunflower, Helianthus annuus), Russian thistle (Salsola kali), and velvetleaf (Abutilon theophrasti) were planted into a blend of loam soil and sand and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant.
At the same time, plants selected from these crop and weed species and also barley, winter (winter barley, Hordeum vulgare), windgrass (Apera spica-venti), chickweed (common chickweed, Stellaria media), deadnettle (henbit deadnettle, Lamium amplexicaule), and canarygrass (littleseed canarygrass, Phalaris minor) were planted in pots containing Redi-Earth® planting medium (Scotts Company, 14111 Scottslawn Road, Marysville, Ohio 43041) comprising spaghnum peat moss, vermiculite, wetting agent and starter nutrients and treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for 13 to 15 days, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table C, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.
Plant species in the flooded paddy test consisted of rice (Oryza sativa), sedge, umbrella (small-flower umbrella sedge, Cyperus difformis), ducksalad (Heteranthera limosa), and barnyardgrass (Echinochloa crus-galli) grown to the 2-leaf stage for testing. At time of treatment, test pots were flooded to 3 cm above the soil surface, treated by application of test compounds directly to the paddy water, and then maintained at that water depth for the duration of the test. Treated plants and controls were maintained in a greenhouse for 13 to 15 days, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table C, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.









TABLE C









Compounds





















250 g ai/ha
5
7
10
16
25
47
52
57
58
59
62
72
73
74










Postemergence





















Barley
10
15
10
35
—
—
—
—
—
—
—
—
—
—


Barnyardgrass
—
—
—
—
25
5
10
15
75
25
10
40
35
15


Bermudagrass
35
70
50
55
—
—
—
—
—
—
—
—
—
—


Blackgrass
45
50
75
70
85
40
25
30
55
40
50
15
25
5


Bromegrass, Downy
10
10
15
5
—
—
—
—
—
—
—
—
—
—


Canarygrass
40
80
40
80
—
—
—
—
—
—
—
—
—
—


Chickweed
45
98
98
90
98
50
95
80
100
98
90
80
80
50


Cocklebur
65
80
100
80
—
—
—
—
—
—
—
—
—
—


Corn
70
75
20
20
15
5
10
20
45
20
20
20
10
20


Crabgrass, Large
20
20
35
85
30
10
40
30
85
40
35
60
20
20


Cupgrass, Woolly
30
25
15
30
—
—
—
—
—
—
—
—
—
—


Deadnettle
90
100
95
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
10
10
5
85
30
80
70
30
95
90
25
65
30
20


Foxtail, Green
70
98
30
100
—
—
—
—
—
—
—
—
—
—


Galium
95
98
95
—
90
65
90
95
95
90
95
95
70
65


Goosegrass
15
15
10
30
—
—
—
—
—
—
—
—
—
—


Johnsongrass
10
10
10
10
15
5
10
20
85
85
15
25
25
25


Kochia
100
100
98
100
100
60
95
100
100
100
95
95
90
90


Lambsquarters
98
98
98
100
100
90
100
85
98
90
90
98
80
85


Morningglory
90
—
85
85
—
75
100
95
98
95
90
90
85
85


Nutsedge, Yellow
15
20
5
20
10
10
30
15
15
10
15
10
5
0


Oat, Wild
30
55
30
45
35
5
15
35
55
40
35
35
15
10


Oilseed Rape
—
—
—
—
—
55
85
85
85
95
75
90
80
65


Pigweed
100
100
100
100
98
70
95
95
100
98
80
95
90
80


Ragweed
85
60
80
90
65
85
95
65
90
55
50
60
65
60


Ryegrass, Italian
25
40
10
20
—
0
10
15
35
30
15
10
5
5


Soybean
95
98
95
90
80
65
95
100
98
98
95
95
90
80


Surinam Grass
—
—
15
40
—
—
—
—
—
—
—
—
—
—


Velvetleaf
98
85
90
75
65
100
90
60
85
70
85
75
70
65


Waterhemp
—
—
—
—
98
100
95
90
100
98
75
95
90
80


Wheat
40
15
10
35
10
0
5
15
30
20
20
5
5
5


Windgrass
85
80
65
50
—
—
—
—
—
—
—
—
—
—












Compounds














250 g ai/ha
79
194
200
204
284











Postemergence














Barley
—
—
—
—
—



Barnyardgrass
75
55
15
35
15



Bermudagrass
—
—
—
—
—



Blackgrass
80
35
35
25
5



Bromegrass, Downy
—
—
—
—
—



Canarygrass
—
—
—
—
—



Chickweed
95
85
98
100
100



Cocklebur
—
—
—
—
—



Corn
35
30
20
20
20



Crabgrass, Large
65
50
20
65
10



Cupgrass, Woolly
—
—
—
—
—



Deadnettle
—
—
—
—
—



Foxtail, Giant
65
15
15
90
25



Foxtail, Green
—
—
—
—
—



Galium
95
90
95
100
100



Goosegrass
—
—
—
—
—



Johnsongrass
85
35
30
30
20



Kochia
95
95
100
100
100



Lambsquarters
98
98
95
95
98



Morningglory
98
95
95
95
100



Nutsedge, Yellow
25
5
35
5
5



Oat, Wild
50
45
20
15
5



Oilseed Rape
90
90
70
75
80



Pigweed
98
95
95
98
100



Ragweed
85
50
85
75
80



Ryegrass, Italian
20
15
5
10
5



Soybean
95
85
90
95
65



Surinam Grass
—
—
—
—
—



Velvetleaf
90
75
70
70
70



Waterhemp
100
90
95
95
100



Wheat
35
5
5
10
5



Windgrass
—
—
—
—
—













Compounds





















125 g ai/ha
5
7
10
16
25
47
52
57
58
59
62
65
72
73










Postemergence





















Barley
5
10
5
10
—
—
—
—
—
—
—
—
—
—


Barnyardgrass
—
—
—
—
20
0
5
10
15
10
5
10
10
10


Bermudagrass
10
15
5
50
—
—
—
—
—
—
—
—
—
—


Blackgrass
20
45
40
30
60
5
10
30
30
25
30
15
15
5


Bromegrass, Downy
5
10
10
5
—
—
—
—
—
—
—
—
—
—


Canarygrass
30
30
25
60
—
—
—
—
—
—
—
—
—
—


Chickweed
—
90
35
75
98
50
90
80
100
80
75
98
80
50


Cocklebur
50
55
55
—
—
—
—
—
—
—
—
—
—
—


Corn
60
60
5
10
—
5
10
20
25
15
15
10
15
10


Crabgrass, Large
20
10
5
30
20
5
20
10
50
30
10
5
55
10


Cupgrass, Woolly
10
25
5
20
—
—
—
—
—
—
—
—
—
—


Deadnettle
90
98
80
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
5
10
5
15
30
25
70
15
80
45
20
10
10
10


Foxtail, Green
40
50
0
30
—
—
—
—
—
—
—
—
—
—


Galium
80
90
80
—
90
55
85
70
85
90
80
98
95
70


Goosegrass
10
15
5
15
—
—
—
—
—
—
—
—
—
—


Johnsongrass
5
5
5
10
10
5
5
5
35
35
10
5
5
5


Kochia
70
100
95
98
100
25
90
90
100
100
90
98
95
90


Lambsquarters
98
98
75
100
98
60
90
70
98
90
85
90
85
70


Morningglory
60
95
65
80
98
70
95
85
98
95
85
95
85
85


Nutsedge, Yellow
15
15
5
5
10
0
5
5
15
5
5
15
0
5


Oat, Wild
10
35
5
35
30
0
10
30
45
40
30
5
30
10


Oilseed Rape
—
—
—
—
90
55
70
80
85
85
60
90
70
60


Pigweed
100
100
100
100
90
65
80
—
98
95
75
98
85
80


Ragweed
55
55
55
40
65
50
80
55
85
25
50
35
60
50


Ryegrass, Italian
10
10
5
20
—
0
10
10
10
10
5
5
10
0


Soybean
95
98
85
90
80
65
95
95
98
98
95
85
90
80


Surinam Grass
45
30
15
40
—
—
—
—
—
—
—
—
—
—


Velvetleaf
80
85
70
75
50
70
70
40
60
55
75
65
55
50


Waterhemp
—
—
—
—
90
100
75
80
90
90
75
90
75
75


Wheat
10
10
5
35
10
0
5
10
25
20
5
10
0
0


Windgrass
60
55
50
50
—
—
—
—
—
—
—
—
—
—












Compounds





















125 g ai/ha
74
79
80
83
84
85
86
88
89
90
92
94
97
98










Postemergence





















Barley
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Barnyardgrass
5
20
5
5
15
5
5
10
5
10
10
10
15
15


Bermudagrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Blackgrass
0
35
40
20
20
10
10
10
5
15
35
5
40
20


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Canarygrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Chickweed
50
90
70
70
50
40
80
90
60
50
70
70
90
85


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
15
15
5
10
5
10
10
10
5
5
5
5
15
20


Crabgrass, Large
15
30
5
10
30
10
5
10
5
10
10
10
55
5


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
10
20
5
40
50
15
25
40
10
20
10
10
15
10


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Galium
65
80
95
60
95
75
80
95
55
85
80
80
90
80


Goosegrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Johnsongrass
25
40
5
10
0
10
5
10
5
5
5
5
5
10


Kochia
90
95
95
95
80
90
95
100
50
90
85
90
100
98


Lambsquarters
75
95
55
80
80
70
85
75
55
60
75
85
98
98


Morningglory
75
95
60
85
85
40
85
95
85
85
85
55
95
85


Nutsedge, Yellow
0
5
5
5
—
10
5
10
5
10
5
10
5
5


Oat, Wild
10
20
10
5
15
5
10
10
15
5
15
5
25
20


Oilseed Rape
40
50
90
80
60
15
45
45
60
40
70
80
80
98


Pigweed
65
95
75
85
85
70
80
90
40
70
75
85
95
75


Ragweed
40
70
45
70
80
65
85
60
70
65
55
45
70
40


Ryegrass, Italian
0
20
5
5
0
5
5
0
5
0
35
5
15
25


Soybean
75
90
80
90
90
90
75
65
95
60
95
80
95
90


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
50
70
75
65
90
55
65
55
40
60
60
40
70
90


Waterhemp
60
90
90
90
70
60
75
90
60
75
80
70
95
85


Wheat
0
5
30
5
0
0
0
5
5
0
5
0
10
10


Windgrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—












Compounds





















125 g ai/ha
111
116
117
120
123
129
132
134
136
138
140
141
145
147










Postemergence





















Barley
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Barnyardgrass
35
20
10
10
15
5
5
10
5
5
10
40
5
10


Bermudagrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Blackgrass
10
25
10
30
0
10
5
10
5
10
5
60
10
10


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Canarygrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Chickweed
95
80
80
80
60
55
40
80
60
55
70
100
65
90


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
15
5
5
10
5
15
10
5
5
10
10
20
5
10


Crabgrass, Large
35
30
20
10
5
10
10
15
15
15
20
45
5
10


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
65
10
55
35
20
10
10
5
10
50
20
70
25
50


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Galium
100
80
80
60
90
85
70
85
60
85
95
100
60
90


Goosegrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Johnsongrass
10
15
5
10
10
5
5
15
—
10
25
30
10
10


Kochia
95
95
100
100
85
100
95
95
70
95
90
100
90
100


Lambsquarters
90
80
75
85
85
85
50
65
75
75
85
100
85
98


Morningglory
98
80
90
80
75
85
65
95
40
85
70
100
60
80


Nutsedge, Yellow
5
—
5
25
10
10
10
10
10
10
5
15
0
5


Oat, Wild
5
15
20
5
0
10
5
10
5
10
5
30
5
5


Oilseed Rape
80
40
70
15
70
60
95
60
5
80
50
98
70
95


Pigweed
85
95
90
95
85
90
80
85
55
80
90
98
75
85


Ragweed
90
70
60
60
75
85
35
55
45
45
75
90
50
85


Ryegrass, Italian
0
5
5
5
0
5
5
0
0
5
0
40
0
5


Soybean
95
95
50
80
90
60
50
90
90
95
75
95
65
90


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
80
85
45
50
100
40
45
55
25
55
60
100
80
75


Waterhemp
90
95
90
85
80
85
75
85
30
85
85
100
80
70


Wheat
5
5
20
0
5
5
5
25
5
5
10
25
0
15


Windgrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—












Compounds





















125 g ai/ha
150
154
155
160
163
164
166
167
177
178
180
181
191
192










Postemergence





















Barley
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Barnyardgrass
5
20
10
5
5
5
15
10
10
10
20
10
15
10


Bermudagrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Blackgrass
10
0
5
15
15
15
60
30
35
60
30
25
10
10


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Canarygrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Chickweed
70
60
90
70
95
90
95
80
85
80
80
85
98
60


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
10
0
10
5
10
5
15
15
10
10
10
5
10
5


Crabgrass, Large
10
10
15
10
10
10
15
10
10
10
35
10
10
5


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
25
15
25
10
10
10
35
30
20
25
80
10
15
10


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Galium
80
85
100
85
95
65
95
90
98
98
90
80
98
85


Goosegrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Johnsongrass
5
5
5
5
10
10
5
25
10
35
5
20
10
10


Kochia
85
80
100
100
100
95
100
95
95
95
60
100
100
90


Lambsquarters
80
70
98
95
95
65
98
100
90
98
85
100
95
90


Morningglory
80
80
85
65
90
80
95
90
85
65
90
98
50
35


Nutsedge, Yellow
5
10
5
5
5
5
5
20
10
10
10
—
5
40


Oat, Wild
5
0
25
0
20
15
50
35
30
30
30
5
10
5


Oilseed Rape
50
80
80
60
80
60
98
70
90
98
55
100
50
60


Pigweed
65
75
98
85
90
80
98
98
95
98
70
98
98
70


Ragweed
65
90
85
70
60
55
80
55
60
65
70
45
35
45


Ryegrass, Italian
5
0
10
5
10
0
30
30
0
20
10
10
5
5


Soybean
95
75
80
60
75
65
95
60
95
95
95
95
30
80


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
30
80
85
90
—
65
85
70
80
100
85
70
65
75


Waterhemp
65
70
98
85
80
75
90
98
100
100
75
98
95
85


Wheat
25
5
35
5
5
0
20
5
5
0
5
5
0
5


Windgrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—












Compounds





















125 g ai/ha
194
200
204
220
221
223
228
232
236
240
245
253
258
273










Postemergence





















Barley
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Barnyardgrass
15
10
5
15
10
5
5
20
10
20
5
20
10
10


Bermudagrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Blackgrass
30
10
10
50
5
0
40
25
20
5
5
10
10
10


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Canarygrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Chickweed
70
95
98
80
50
60
50
60
50
55
100
90
95
70


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
25
15
20
10
10
5
5
15
10
15
5
25
20
5


Crabgrass, Large
10
15
15
5
25
5
5
5
5
20
15
20
15
10


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
15
5
10
5
5
5
5
15
15
40
15
20
45
20


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Galium
85
85
75
95
90
100
80
95
85
70
85
100
100
80


Goosegrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Johnsongrass
25
5
10
5
20
5
10
5
20
10
10
10
5
5


Kochia
90
98
100
95
95
90
85
98
90
90
98
100
100
95


Lambsquarters
90
85
90
75
65
95
65
75
90
90
98
95
90
80


Morningglory
80
95
98
50
55
80
35
85
75
90
85
85
95
85


Nutsedge, Yellow
5
30
0
5
10
5
5
5
5
5
10
5
5
25


Oat, Wild
40
25
15
50
30
5
5
20
5
0
5
10
15
10


Oilseed Rape
85
50
85
90
80
85
85
60
65
60
80
80
98
25


Pigweed
90
95
95
90
85
90
55
85
95
75
85
95
90
90


Ragweed
50
55
35
25
10
75
45
60
75
75
60
80
75
80


Ryegrass, Italian
0
5
10
10
5
5
10
10
0
0
5
0
30
10


Soybean
75
95
95
95
80
95
80
75
95
75
90
90
95
90


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
70
75
60
60
75
90
70
65
80
80
55
85
80
30


Waterhemp
85
90
90
85
80
95
75
85
90
70
75
85
90
80


Wheat
0
5
10
0
0
5
0
5
0
5
5
0
5
10


Windgrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—













Compounds












125 g ai/ha
274
284











Postemergence











Barley
—
—



Barnyardgrass
15
15



Bermudagrass
—
—



Blackgrass
20
5



Bromegrass, Downy
—
—



Canarygrass
—
—



Chickweed
98
100



Cocklebur
—
—



Corn
15
20



Crabgrass, Large
60
10



Cupgrass, Woolly
—
—



Deadnettle
—
—



Foxtail, Giant
60
20



Foxtail, Green
—
—



Galium
98
85



Goosegrass
—
—



Johnsongrass
10
20



Kochia
100
100



Lambsquarters
98
98



Morningglory
95
85



Nutsedge, Yellow
10
0



Oat, Wild
30
5



Oilseed Rape
90
80



Pigweed
98
100



Ragweed
75
50



Ryegrass, Italian
35
5



Soybean
98
85



Surinam Grass
—
—



Velvetleaf
75
30



Waterhemp
98
98



Wheat
15
5



Windgrass
—
—













Compounds





















62 g ai/ha
5
7
10
16
25
47
52
57
58
59
62
65
72
73










Postemergence





















Barley
0
0
5
5
—
—
—
—
—
—
—
—
—
—


Barnyardgrass
—
—
—
—
20
0
5
10
5
5
5
5
5
0


Bermudagrass
0
5
5
15
—
—
—
—
—
—
—
—
—
—


Blackgrass
5
10
5
30
50
0
5
15
15
10
5
40
10
0


Bromegrass, Downy
5
5
5
5
—
—
—
—
—
—
—
—
—
—


Canarygrass
10
10
0
30
—
—
—
—
—
—
—
—
—
—


Chickweed
15
—
30
65
90
5
60
50
95
70
50
70
65
50


Cocklebur
50
45
55
55
—
—
—
—
—
—
—
—
—
—


Corn
20
25
5
5
15
0
10
15
15
15
15
10
10
5


Crabgrass, Large
15
5
5
20
20
5
15
5
20
10
5
5
10
10


Cupgrass, Woolly
10
20
5
15
—
—
—
—
—
—
—
—
—
—


Deadnettle
50
98
60
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
5
5
0
10
15
25
50
10
40
45
10
10
10
5


Foxtail, Green
40
—
0
30
—
—
—
—
—
—
—
—
—
—


Galium
70
80
80
—
80
50
60
50
70
80
65
85
80
55


Goosegrass
5
5
5
10
—
—
—
—
—
—
—
—
—
—


Johnsongrass
5
0
—
5
5
5
5
5
15
35
5
5
5
5


Kochia
55
98
40
80
98
10
90
90
95
100
90
98
90
85


Lambsquarters
95
98
55
100
80
45
90
70
90
80
60
75
75
55


Morningglory
60
80
65
80
98
70
80
80
95
85
70
65
75
65


Nutsedge, Yellow
5
15
5
5
10
0
5
5
5
5
5
5
0
0


Oat, Wild
5
35
0
35
15
0
5
15
40
25
0
5
5
5


Oilseed Rape
—
—
—
—
85
50
40
40
70
50
20
60
70
30


Pigweed
98
100
98
98
90
55
60
85
95
90
65
95
80
70


Ragweed
45
55
50
30
65
50
45
40
45
25
40
25
40
35


Ryegrass, Italian
5
10
0
15
—
0
5
5
5
10
0
0
5
0


Soybean
90
98
75
85
80
45
90
85
95
85
85
60
80
70


Surinam Grass
35
20
10
15
—
—
—
—
—
—
—
—
—
—


Velvetleaf
55
50
70
—
40
50
60
35
50
30
20
55
40
30


Waterhemp
—
—
—
—
80
100
70
80
90
85
60
95
75
60


Wheat
5
5
5
15
5
0
0
5
15
5
0
5
0
0


Windgrass
40
55
10
40
—
—
—
—
—
—
—
—
—
—












Compounds





















62 g ai/ha
74
79
80
83
84
85
86
88
89
90
92
94
97
98










Postemergence





















Barley
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Barnyardgrass
5
5
5
5
0
5
5
5
5
5
5
10
10
10


Bermudagrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Blackgrass
0
30
10
5
5
5
5
10
5
5
10
5
10
30


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Canarygrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Chickweed
30
65
65
60
40
50
60
20
50
15
60
60
80
75


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
10
5
5
5
0
10
5
10
5
5
5
35
10
5


Crabgrass, Large
5
20
5
10
5
5
5
10
5
10
5
10
15
5


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
5
10
5
10
5
10
15
30
5
20
5
10
10
5


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Galium
55
75
85
70
60
50
80
70
50
65
65
80
85
75


Goosegrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Johnsongrass
0
10
5
10
0
5
5
5
5
5
5
5
15
5


Kochia
90
90
95
90
70
80
90
95
60
45
80
90
95
90


Lambsquarters
75
95
55
60
55
75
65
60
65
60
40
75
80
80


Morningglory
75
95
60
75
85
25
85
85
55
75
90
75
85
65


Nutsedge, Yellow
0
5
5
5
—
5
5
10
20
10
5
45
5
5


Oat, Wild
0
15
5
10
5
5
5
10
5
5
10
0
15
10


Oilseed Rape
40
50
80
55
45
30
60
55
55
50
60
50
80
95


Pigweed
60
95
65
75
80
70
65
85
35
45
55
80
85
75


Ragweed
40
70
40
60
40
20
55
55
60
50
50
55
60
30


Ryegrass, Italian
0
10
20
5
0
0
5
10
5
5
5
0
5
5


Soybean
65
85
75
70
90
65
70
95
90
75
90
85
90
60


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
35
70
65
50
70
45
65
40
25
60
50
65
75
70


Waterhemp
60
80
70
70
70
70
60
85
30
65
75
75
90
80


Wheat
0
5
5
0
0
5
0
5
0
0
0
0
5
5


Windgrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—












Compounds





















62 g ai/ha
111
116
117
120
123
129
132
134
136
138
140
141
145
147










Postemergence





















Barley
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Barnyardgrass
5
5
5
10
15
5
5
5
0
5
10
20
0
5


Bermudagrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Blackgrass
5
10
5
5
0
5
10
5
5
5
0
35
5
0


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Canarygrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Chickweed
75
55
70
70
50
70
30
55
5
50
45
95
45
75


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
10
5
5
5
5
10
5
10
0
5
10
5
5
5


Crabgrass, Large
10
15
20
10
5
5
5
10
5
15
15
10
5
10


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
35
40
40
10
20
5
5
5
5
10
20
45
25
20


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Galium
90
80
70
30
85
55
65
85
55
65
90
98
55
90


Goosegrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Johnsongrass
5
0
5
5
10
5
5
5
0
5
5
10
0
5


Kochia
90
90
100
95
70
95
85
95
60
95
85
100
85
95


Lambsquarters
80
50
50
70
85
80
60
75
60
60
80
100
85
90


Morningglory
80
60
90
35
55
80
75
85
50
65
75
95
50
75


Nutsedge, Yellow
5
—
5
10
10
5
0
10
5
5
5
15
5
0


Oat, Wild
5
5
10
5
0
15
5
10
5
5
0
10
0
0


Oilseed Rape
60
10
60
5
60
60
70
70
5
60
50
95
60
75


Pigweed
85
90
85
85
85
80
75
85
55
80
90
100
65
75


Ragweed
70
25
35
25
70
40
10
55
45
40
60
98
35
75


Ryegrass, Italian
0
5
0
0
0
20
5
5
0
0
0
5
0
0


Soybean
80
60
50
30
65
85
35
65
75
65
65
90
35
85


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
75
60
30
35
80
40
40
50
10
20
45
100
60
85


Waterhemp
80
80
85
80
80
65
65
60
35
75
80
100
55
85


Wheat
0
5
5
0
0
0
0
5
5
0
0
5
0
10


Windgrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—












Compounds





















62 g ai/ha
150
154
155
160
163
164
166
167
172
177
178
180
181
191










Postemergence





















Barley
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Barnyardgrass
5
10
5
5
5
5
10
10
5
10
5
5
10
15


Bermudagrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Blackgrass
10
0
5
5
5
5
45
5
0
5
20
5
15
5


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Canarygrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Chickweed
65
10
75
80
80
80
90
70
70
55
65
70
80
80


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
10
0
5
5
10
5
10
10
0
10
10
5
5
10


Crabgrass, Large
5
10
5
5
10
5
10
5
0
10
5
5
10
5


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
20
5
15
5
10
10
10
10
5
10
5
10
25
10


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Galium
75
80
98
95
85
80
90
70
10
85
85
60
70
98


Goosegrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Johnsongrass
5
0
5
0
5
5
5
15
10
5
15
0
5
15


Kochia
55
80
98
98
100
90
90
90
30
90
95
50
100
98


Lambsquarters
35
60
98
70
85
40
95
98
0
75
85
75
100
75


Morningglory
65
65
80
75
65
55
85
98
10
80
85
75
75
85


Nutsedge, Yellow
15
10
5
5
5
5
5
5
5
5
5
10
5
5


Oat, Wild
5
0
5
0
10
5
35
35
0
10
10
20
5
5


Oilseed Rape
45
50
50
60
60
55
95
85
0
90
90
40
60
50


Pigweed
55
60
98
75
90
75
90
95
5
85
95
60
85
95


Ragweed
35
100
70
60
35
60
60
30
0
55
30
80
30
30


Ryegrass, Italian
5
0
10
0
0
0
15
5
5
0
0
5
5
5


Soybean
65
65
75
60
80
75
90
60
5
85
65
98
50
60


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
30
70
70
80
—
40
80
40
10
70
85
65
40
75


Waterhemp
35
65
80
70
85
65
90
85
5
95
90
70
85
95


Wheat
5
0
15
5
0
0
35
5
0
0
0
0
0
0


Windgrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—












Compounds





















62 g ai/ha
192
194
200
204
220
221
222
223
228
232
236
240
245
253










Postemergence





















Barley
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Barnyardgrass
10
5
5
10
10
5
15
5
5
10
5
10
5
10


Bermudagrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Blackgrass
5
20
5
5
40
5
60
5
0
5
5
0
5
0


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Canarygrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Chickweed
70
70
75
95
80
60
100
50
50
50
65
55
80
90


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
5
—
10
20
10
10
0
5
0
10
5
5
5
5


Crabgrass, Large
5
10
5
10
5
5
5
5
5
5
5
5
10
15


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
5
10
5
5
10
5
5
5
0
5
15
20
20
25


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Galium
80
65
65
75
80
55
85
80
70
80
80
55
80
80


Goosegrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Johnsongrass
5
5
5
5
5
5
10
0
5
5
15
5
10
5


Kochia
85
90
95
100
95
95
100
80
80
90
85
45
90
100


Lambsquarters
90
80
80
80
55
50
75
75
75
70
75
75
80
80


Morningglory
35
80
80
65
40
50
70
70
25
55
70
75
65
75


Nutsedge, Yellow
0
5
5
10
0
5
5
5
5
5
0
0
5
5


Oat, Wild
5
15
15
15
35
10
30
0
0
5
5
0
5
10


Oilseed Rape
60
40
55
70
85
60
20
80
60
5
30
55
50
10


Pigweed
80
75
90
95
85
50
85
80
60
60
90
45
75
98


Ragweed
15
25
40
40
15
20
60
55
55
50
40
55
45
55


Ryegrass, Italian
5
0
10
5
5
5
0
0
0
5
0
0
0
0


Soybean
75
50
95
95
60
65
60
85
60
70
85
60
60
40


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
65
45
50
40
65
45
50
80
60
30
85
45
35
70


Waterhemp
65
80
98
90
75
80
90
85
60
70
90
55
85
80


Wheat
5
0
0
5
0
0
5
0
0
0
0
5
0
0


Windgrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—













Compounds














62 g ai/ha
258
273
274
284











Postemergence













Barley
—
—
—
—



Barnyardgrass
10
5
10
10



Bermudagrass
—
—
—
—



Blackgrass
5
10
15
5



Bromegrass, Downy
—
—
—
—



Canarygrass
—
—
—
—



Chickweed
90
35
90
100



Cocklebur
—
—
—
—



Corn
10
5
10
10



Crabgrass, Large
10
10
30
5



Cupgrass, Woolly
—
—
—
—



Deadnettle
—
—
—
—



Foxtail, Giant
25
10
10
10



Foxtail, Green
—
—
—
—



Galium
95
60
90
85



Goosegrass
—
—
—
—



Johns ongrass
5
5
5
5



Kochia
100
80
100
100



Lambsquarters
90
85
95
85



Morningglory
85
65
95
100



Nutsedge, Yellow
5
5
20
0



Oat, Wild
10
5
35
5



Oilseed Rape
95
5
85
70



Pigweed
85
65
90
98



Ragweed
50
55
40
55



Ryegrass, Italian
0
5
30
5



Soybean
70
90
90
40



Surinam Grass
—
—
—
—



Velvetleaf
75
25
65
15



Waterhemp
80
65
95
85



Wheat
5
0
5
5



Windgrass
—
—
—
—













Compounds





















31 g ai/ha
5
7
10
16
25
47
52
57
58
59
62
65
72
73










Postemergence





















Barley
0
0
0
0
—
—
—
—
—
—
—
—
—
—


Barnyardgrass
—
—
—
—
15
0
0
5
5
5
0
5
5
0


Bermudagrass
0
0
0
10
—
—
—
—
—
—
—
—
—
—


Blackgrass
0
5
5
5
5
0
5
10
10
5
0
10
10
0


Bromegrass, Downy
5
5
5
0
—
—
—
—
—
—
—
—
—
—


Canarygrass
5
5
0
10
—
—
—
—
—
—
—
—
—
—


Chickweed
5
80
5
40
80
5
40
50
95
40
50
50
50
50


Cocklebur
25
35
45
50
—
—
—
—
—
—
—
—
—
—


Corn
15
—
5
5
5
0
5
10
10
10
5
10
5
5


Crabgrass, Large
5
5
5
10
15
5
5
5
5
10
5
5
5
5


Cupgrass, Woolly
0
10
0
5
—
—
—
—
—
—
—
—
—
—


Deadnettle
50
85
50
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
5
0
0
5
10
10
45
10
15
10
5
10
10
0


Foxtail, Green
0
0
0
10
—
—
—
—
—
—
—
—
—
—


Galium
55
65
65
—
70
35
60
50
60
65
65
50
75
40


Goosegrass
0
0
0
0
—
—
—
—
—
—
—
—
—
—


Johnsongrass
5
0
5
0
5
0
5
5
15
15
5
5
0
0


Kochia
20
98
20
35
95
5
75
85
95
95
80
90
90
80


Lambsquarters
80
60
55
75
75
30
85
70
75
70
60
80
75
25


Morningglory
40
75
40
65
60
20
80
45
80
80
65
30
75
65


Nutsedge, Yellow
5
10
0
5
0
0
0
5
5
0
0
5
0
0


Oat, Wild
0
5
0
25
0
0
0
10
35
25
0
0
5
5


Oilseed Rape
—
—
—
—
50
15
25
30
60
50
20
25
55
10


Pigweed
98
100
75
80
90
40
60
65
90
80
50
90
70
45


Ragweed
15
50
50
15
15
20
40
35
40
10
40
5
40
30


Ryegrass, Italian
0
5
0
10
—
0
0
0
5
5
0
0
5
0


Soybean
55
85
50
75
60
35
40
65
95
75
45
40
—
40


Surinam Grass
10
15
0
10
—
—
—
—
—
—
—
—
—
—


Velvetleaf
45
40
50
60
30
45
50
25
45
15
20
50
40
30


Waterhemp
—
—
—
—
75
100
70
75
85
85
40
75
75
50


Wheat
0
5
5
5
5
0
0
0
10
5
0
0
0
0


Windgrass
10
10
10
30
—
—
—
—
—
—
—
—
—
—












Compounds





















31 g ai/ha
74
79
80
83
84
85
86
88
89
90
92
94
97
98










Postemergence





















Barley
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Barnyardgrass
0
5
5
5
0
5
5
5
5
5
5
10
10
5


Bermudagrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Blackgrass
0
10
5
5
5
0
5
10
0
0
0
5
5
5


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Canarygrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Chickweed
25
50
60
40
10
40
55
15
50
30
60
60
60
50


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
10
5
0
5
0
5
5
10
5
5
5
5
5
10


Crabgrass, Large
5
20
5
5
5
10
5
5
5
5
5
5
10
5


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
5
10
5
35
5
10
5
35
5
15
5
10
5
5


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Galium
40
65
70
65
75
50
60
80
40
55
80
70
75
60


Goosegrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Johnsongrass
—
5
0
0
0
0
5
0
5
5
0
5
5
0


Kochia
80
90
90
70
55
50
60
95
50
70
60
80
90
80


Lambsquarters
40
90
60
80
30
55
45
75
30
75
35
65
75
35


Morningglory
60
70
10
65
70
60
80
90
70
60
85
75
85
30


Nutsedge, Yellow
0
5
5
0
—
5
0
5
5
5
5
5
5
10


Oat, Wild
0
10
0
0
0
0
0
5
5
0
5
0
10
5


Oilseed Rape
35
30
70
50
20
5
40
50
25
5
45
50
60
80


Pigweed
40
75
60
75
50
55
65
85
35
45
60
80
85
75


Ragweed
40
55
40
40
10
20
50
55
40
40
40
15
40
10


Ryegrass, Italian
0
5
0
0
0
0
0
5
0
5
5
0
5
0


Soybean
40
65
60
60
55
75
60
65
65
65
70
45
60
40


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
30
55
45
55
45
45
25
35
15
55
45
20
40
50


Waterhemp
35
75
65
50
50
55
70
75
40
35
45
80
85
50


Wheat
0
0
0
0
0
0
0
5
0
0
0
0
5
0


Windgrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—












Compounds





















31 g ai/ha
111
115
116
117
120
123
129
132
134
136
138
140
141
145










Postemergence





















Barley
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Barnyardgrass
5
5
5
5
5
15
5
0
5
0
5
10
15
0


Bermudagrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Blackgrass
0
5
5
10
5
0
5
5
25
5
5
0
35
0


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Canarygrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Chickweed
60
5
60
75
50
20
60
30
50
5
40
40
90
40


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
5
5
0
5
5
5
5
5
5
0
5
5
5
5


Crabgrass, Large
5
5
5
10
10
5
5
5
5
5
15
15
10
5


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
20
25
35
20
5
0
5
5
5
5
10
15
35
0


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Galium
80
50
55
65
30
75
50
60
75
40
60
90
95
50


Goosegrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Johnsongrass
5
5
0
5
5
10
5
5
5
0
5
5
5
0


Kochia
65
5
75
95
80
60
95
45
90
30
95
85
100
45


Lambsquarters
65
25
5
50
65
60
75
50
65
40
30
65
85
55


Morningglory
85
10
80
40
35
25
80
55
75
25
65
65
85
30


Nutsedge, Yellow
0
0
—
5
5
5
0
0
10
0
0
5
15
0


Oat, Wild
0
5
5
15
5
0
10
0
5
5
5
0
0
0


Oilseed Rape
60
0
5
30
5
40
15
50
10
0
80
30
55
40


Pigweed
75
60
85
85
85
80
75
45
80
20
85
85
90
60


Ragweed
45
10
15
40
15
45
20
0
20
35
35
60
98
35


Ryegrass, Italian
0
5
5
5
0
0
10
0
5
0
0
0
0
0


Soybean
75
5
50
40
55
50
35
35
60
65
75
50
80
25


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
60
5
40
15
10
70
20
20
35
15
45
25
85
30


Waterhemp
65
40
70
65
80
55
65
20
75
30
70
75
85
35


Wheat
0
0
5
0
0
0
0
0
0
5
0
0
0
0


Windgrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—












Compounds





















31 g ai/ha
147
150
152
154
155
160
163
164
166
167
172
177
178
180










Postemergence





















Barley
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Barnyardgrass
5
5
5
5
5
5
5
0
10
5
5
5
5
5


Bermudagrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Blackgrass
0
5
0
0
5
0
5
0
10
5
20
5
5
10


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Canarygrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Chickweed
70
65
30
5
80
55
80
50
80
80
50
50
50
60


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
5
10
5
0
5
5
5
5
5
5
0
5
10
5


Crabgrass, Large
5
5
5
10
5
5
5
5
5
5
0
5
10
5


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
0
20
5
10
5
5
5
20
5
10
0
10
5
5


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Galium
90
65
55
65
95
80
50
55
85
70
0
50
75
55


Goosegrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Johnsongrass
5
0
5
0
0
0
5
0
5
15
10
5
5
0


Kochia
90
55
40
50
98
90
90
90
90
90
0
70
90
50


Lambsquarters
75
30
80
55
90
65
80
25
80
90
0
65
80
55


Morningglory
70
60
40
65
80
75
50
35
70
60
20
10
70
65


Nutsedge, Yellow
0
0
0
10
5
5
5
5
5
0
5
5
5
0


Oat, Wild
0
5
5
0
0
0
5
5
10
25
0
0
0
10


Oilseed Rape
40
40
60
50
50
55
30
10
90
50
0
80
85
25


Pigweed
60
55
60
30
75
75
85
75
85
90
10
80
85
55


Ragweed
65
30
40
45
55
45
35
15
45
10
0
15
55
65


Ryegrass, Italian
0
0
0
0
0
0
0
0
5
10
0
0
0
0


Soybean
65
65
60
65
70
55
50
35
95
30
0
65
70
85


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
70
25
45
45
75
65
—
15
55
40
10
70
70
40


Waterhemp
55
35
60
60
65
35
75
45
85
75
5
75
90
60


Wheat
5
5
0
0
10
5
0
0
5
0
0
0
0
0


Windgrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—












Compounds





















31 g ai/ha
181
191
192
194
200
204
220
221
222
223
228
232
236
240










Postemergence





















Barley
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Barnyardgrass
5
10
10
5
0
5
10
5
10
0
0
5
5
10


Bermudagrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Blackgrass
5
0
0
15
5
5
60
0
30
30
0
0
5
0


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Canarygrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Chickweed
75
80
50
50
55
75
70
60
85
50
30
30
50
5


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
5
5
5
5
5
10
10
5
5
5
0
10
5
5


Crabgrass, Large
5
5
10
10
5
5
5
5
5
5
5
5
5
5


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
10
10
5
10
5
5
5
5
5
5
0
5
50
35


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Galium
65
80
80
60
60
70
70
55
85
80
50
70
75
40


Goosegrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Johnsongrass
5
10
10
—
5
5
0
5
10
0
0
0
25
5


Kochia
100
95
45
90
80
90
90
80
100
85
60
85
80
45


Lambsquarters
100
60
25
60
80
85
50
60
65
75
40
60
85
45


Morningglory
20
85
50
50
85
60
50
40
45
45
10
80
45
65


Nutsedge, Yellow
0
0
5
5
5
0
0
0
5
5
0
5
0
0


Oat, Wild
5
5
0
5
15
20
25
5
10
0
0
0
0
0


Oilseed Rape
60
45
5
30
55
40
65
50
10
50
60
50
10
35


Pigweed
98
85
65
75
75
80
75
75
80
70
50
70
90
30


Ragweed
35
20
25
15
25
25
10
5
45
20
20
35
15
40


Ryegrass, Italian
0
0
0
0
5
5
0
0
0
0
0
0
0
0


Soybean
50
55
30
30
90
70
65
55
65
65
35
55
75
40


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
20
65
60
40
20
35
50
35
35
55
55
60
65
25


Waterhemp
85
85
50
80
70
85
70
70
90
60
45
65
70
25


Wheat
0
0
0
0
0
5
0
0
0
0
0
0
0
0


Windgrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—













Compounds
















31 g ai/ha
245
253
258
273
274
284











Postemergence















Barley
—
—
—
—
—
—



Barnyardgrass
5
5
10
5
10
10



Bermudagrass
—
—
—
—
—
—



Blackgrass
0
0
5
5
5
5



Bromegrass, Downy
—
—
—
—
—
—



Canarygrass
—
—
—
—
—
—



Chickweed
60
70
50
30
70
65



Cocklebur
—
—
—
—
—
—



Corn
5
5
5
5
10
5



Crabgrass, Large
5
5
5
5
5
5



Cupgrass, Woolly
—
—
—
—
—
—



Deadnettle
—
—
—
—
—
—



Foxtail, Giant
35
45
20
40
10
10



Foxtail, Green
—
—
—
—
—
—



Galium
60
80
90
60
80
100



Goosegrass
—
—
—
—
—
—



Johnsongrass
5
5
5
0
5
5



Kochia
75
98
95
65
90
100



Lambsquarters
70
80
65
40
95
70



Morningglory
30
75
85
65
85
70



Nutsedge, Yellow
5
5
0
5
5
0



Oat, Wild
0
0
5
5
—
5



Oilseed Rape
50
60
85
0
80
70



Pigweed
55
85
85
80
85
98



Ragweed
40
45
50
55
60
55



Ryegrass, Italian
0
0
0
5
5
5



Soybean
60
60
75
70
70
35



Surinam Grass
—
—
—
—
—
—



Velvetleaf
10
70
65
10
50
15



Waterhemp
65
75
70
40
85
85



Wheat
0
0
0
0
5
0



Windgrass
—
—
—
—
—
—













Compounds





















16 g ai/ha
65
80
83
84
85
86
88
89
90
92
94
97
98
111










Postemergence





















Barnyardgrass
5
0
5
0
10
0
5
0
5
5
10
10
5
5


Blackgrass
0
0
0
5
0
5
5
0
0
0
0
10
0
0


Chickweed
60
50
35
10
5
40
5
20
5
50
10
70
30
50


Corn
5
0
0
0
5
5
5
5
0
5
5
5
5
5


Crabgrass, Large
5
0
5
5
10
5
5
5
5
5
5
5
5
5


Foxtail, Giant
5
0
35
40
5
5
20
5
35
5
10
10
5
20


Galium
100
55
50
60
40
55
70
45
70
70
45
55
50
80


Johnsongrass
5
0
0
0
0
0
0
0
0
0
5
5
0
5


Kochia
90
60
60
55
50
50
90
45
45
40
30
80
70
60


Lambsquarters
55
50
60
50
35
15
25
30
35
15
70
15
10
70


Morningglory
45
5
10
55
45
75
30
70
40
70
70
80
50
50


Nutsedge, Yellow
0
10
0
—
0
0
0
0
0
5
5
0
0
0


Oat, Wild
0
0
0
0
0
0
5
0
5
5
0
5
0
0


Oilseed Rape
10
50
30
10
10
20
50
25
0
40
10
35
75
40


Pigweed
65
45
70
50
30
65
80
10
25
30
75
70
50
65


Ragweed
5
5
30
5
40
40
35
35
35
50
5
40
10
40


Ryegrass, Italian
0
10
0
0
0
0
0
0
5
0
0
5
0
0


Soybean
30
55
15
55
30
55
30
55
30
80
50
35
50
60


Velvetleaf
35
20
30
40
40
20
25
10
55
35
25
35
35
40


Waterhemp
75
40
65
35
25
35
75
25
35
35
80
80
55
50


Wheat
0
0
0
0
0
0
0
0
0
0
0
5
0
0












Compounds





















16 g ai/ha
115
116
117
120
123
129
132
134
136
138
140
141
145
147










Postemergence





















Barnyardgrass
0
0
5
5
10
5
0
0
0
5
5
15
0
0


Blackgrass
0
0
5
0
0
5
5
5
0
0
0
5
0
0


Chickweed
5
40
50
40
5
50
10
45
5
5
30
70
15
15


Corn
5
0
5
5
0
5
5
5
0
5
0
5
5
5


Crabgrass, Large
5
5
10
5
0
5
5
5
5
10
10
5
0
5


Foxtail, Giant
5
30
20
5
0
5
0
5
5
5
5
10
0
0


Galium
40
55
80
30
40
50
50
65
20
50
50
90
45
85


Johnsongrass
5
0
0
0
10
5
5
5
0
5
0
5
0
5


Kochia
0
70
90
75
50
90
10
75
5
80
70
100
30
40


Lambsquarters
10
5
45
55
60
35
10
5
20
20
35
85
25
60


Morningglory
40
50
80
20
5
75
10
70
5
65
0
85
5
70


Nutsedge, Yellow
0
—
5
0
5
0
0
0
0
0
0
10
0
0


Oat, Wild
0
5
10
0
0
0
0
5
0
5
0
0
0
0


Oilseed Rape
0
5
25
5
30
5
40
5
0
5
5
50
5
25


Pigweed
50
80
80
40
70
70
25
75
45
60
85
90
35
35


Ragweed
5
5
25
10
35
15
0
10
25
40
25
80
5
40


Ryegrass, Italian
0
5
0
0
0
0
0
10
0
0
0
0
0
0


Soybean
10
15
35
30
45
35
20
60
35
40
25
85
25
65


Velvetleaf
5
25
10
10
60
15
5
30
10
30
5
80
15
55


Waterhemp
30
65
60
75
25
65
45
55
40
60
75
85
15
40


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
0












Compounds





















16 g ai/ha
150
152
154
155
160
163
164
166
167
172
177
178
180
181










Postemergence





















Barnyardgrass
5
5
5
0
5
5
0
5
5
5
5
5
—
5


Blackgrass
5
0
0
0
0
0
0
5
0
0
0
0
0
5


Chickweed
50
10
5
90
50
40
45
60
55
0
50
40
50
55


Corn
5
5
0
5
0
5
0
5
5
0
5
5
0
5


Crabgrass, Large
5
5
5
5
5
5
5
5
5
0
5
5
5
5


Foxtail, Giant
5
5
5
0
0
5
0
5
10
10
5
5
5
10


Galium
60
35
60
75
80
70
50
80
70
0
60
80
50
60


Johnsongrass
0
5
0
0
0
5
0
5
5
0
5
0
0
0


Kochia
50
15
50
80
85
90
80
90
90
0
70
60
40
70


Lambsquarters
10
40
20
65
65
60
15
40
80
0
60
70
35
75


Morningglory
40
10
55
70
5
20
35
85
80
0
20
10
45
15


Nutsedge, Yellow
0
0
5
5
5
5
5
0
0
0
0
5
0
0


Oat, Wild
5
0
0
0
0
0
0
5
5
0
5
0
5
0


Oilseed Rape
5
35
40
60
10
45
10
60
15
0
60
70
15
55


Pigweed
40
50
25
80
80
80
50
80
80
10
75
80
10
85


Ragweed
30
10
35
50
10
10
20
35
10
0
10
20
35
5


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Soybean
65
35
40
5
40
35
40
40
20
0
45
50
85
35


Velvetleaf
20
20
25
45
45
—
—
45
35
5
50
50
30
25


Waterhemp
35
45
5
45
70
75
50
75
65
5
70
80
25
80


Wheat
5
0
0
5
0
0
0
5
0
0
0
0
0
0












Compounds





















16 g ai/ha
191
192
220
221
222
223
228
232
236
240
245
253
258
273










Postemergence





















Barnyardgrass
10
5
5
5
5
0
0
10
5
0
5
5
5
5


Blackgrass
0
0
0
0
5
0
0
10
0
0
0
0
0
5


Chickweed
10
45
65
20
60
35
10
5
40
5
5
60
50
10


Corn
5
0
5
0
5
5
0
5
5
0
5
5
5
5


Crabgrass, Large
5
5
5
5
5
5
0
5
5
10
5
5
5
5


Foxtail, Giant
10
5
0
0
5
5
0
5
5
0
35
10
5
10


Galium
80
60
50
60
70
75
50
65
60
35
60
45
85
55


Johnsongrass
30
5
5
5
0
0
5
0
10
10
5
0
0
0


Kochia
85
30
90
90
85
70
30
85
30
40
45
80
90
70


Lambsquarters
85
10
15
15
65
60
25
55
80
15
50
30
50
25


Morningglory
40
30
15
45
90
5
5
70
10
30
5
60
65
60


Nutsedge, Yellow
0
5
10
0
5
5
0
5
0
0
5
5
0
10


Oat, Wild
5
0
5
5
10
0
0
0
0
0
0
0
5
5


Oilseed Rape
10
10
50
40
5
10
40
5
30
30
40
5
70
0


Pigweed
95
60
65
60
70
70
25
60
60
15
40
85
75
65


Ragweed
5
10
10
5
40
10
5
25
10
35
35
20
25
30


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
0
0
0
0
5


Soybean
40
30
40
30
55
60
25
30
60
30
40
40
50
60


Velvetleaf
50
35
30
35
40
30
15
35
55
10
5
30
55
5


Waterhemp
80
40
65
65
70
70
15
65
70
10
60
75
65
35


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
0














Compound



16 g ai/ha
274











Postemergence










Barnyardgrass
5



Blackgrass
5



Chickweed
70



Corn
5



Crabgrass, Large
5



Foxtail, Giant
5



Galium
70



Johnsongrass
5



Kochia
85



Lambsquarters
85



Morningglory
85



Nutsedge, Yellow
10



Oat, Wild
30



Oilseed Rape
60



Pigweed
95



Ragweed
50



Ryegrass, Italian
5



Soybean
45



Velvetleaf
30



Waterhemp
70



Wheat
5














Compounds














8 g ai/ha
115
152
172
222











Postemergence













Barnyardgrass
0
0
0
5



Blackgrass
0
0
0
0



Chickweed
5
5
0
10



Corn
10
0
0
0



Crabgrass, Large
5
5
0
5



Foxtail, Giant
5
0
0
0



Galium
5
15
0
65



Johnsongrass
5
0
0
0



Kochia
0
10
0
60



Lambsquarters
10
60
0
50



Morningglory
0
0
0
40



Nutsedge, Yellow
0
0
0
0



Oat, Wild
0
0
0
5



Oilseed Rape
0
5
0
10



Pigweed
15
30
5
65



Ragweed
5
15
0
20



Ryegrass, Italian
0
0
0
0



Soybean
5
30
0
40



Velvetleaf
5
5
5
35



Waterhemp
5
15
0
60



Wheat
0
0
0
0














Compounds












4 g ai/ha
115
152











Postemergence











Barnyardgrass
0
0



Blackgrass
0
0



Chickweed
0
5



Corn
5
0



Crabgrass, Large
0
5



Foxtail, Giant
5
0



Galium
5
5



Johnsongrass
5
0



Kochia
0
0



Lambsquarters
10
25



Morningglory
0
0



Nutsedge, Yellow
0
0



Oat, Wild
0
0



Oilseed Rape
0
5



Pigweed
10
10



Ragweed
5
15



Ryegrass, Italian
0
0



Soybean
5
35



Velvetleaf
5
5



Waterhemp
5
20



Wheat
0
0













Compounds




















250 g ai/ha
7
16
18
25
52
58
59
72
73
79
194
200
204










Preemergence




















Barnyardgrass
—
—
—
98
100
100
100
100
100
100
100
100
100


Bermudagrass
100
98
100
—
—
—
—
—
—
—
—
—
—


Blackgrass
85
90
90
85
90
90
90
95
90
90
90
98
95


Bromegrass, Downy
75
95
95
—
—
—
—
—
—
—
—
—
—


Cocklebur
5
20
15
—
—
—
—
—
—
—
—
—
—


Corn
5
35
35
10
70
98
90
65
70
95
25
75
35


Crabgrass, Large
100
100
100
100
100
100
100
100
100
100
100
100
100


Cupgrass, Woolly
98
98
100
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
100
100
100
100
100
100
100
100
100
100
100
100
100


Foxtail, Green
95
90
90
—
—
—
—
—
—
—
—
—
—


Galium
100
100
100
100
100
100
100
95
95
90
100
100
100


Goosegrass
100
100
100
—
—
—
—
—
—
—
—
—
—


Johnsongrass
75
100
98
45
100
100
100
100
98
100
95
98
98


Kochia
100
100
98
—
—
—
—
—
—
—
—
—
—


Lambsquarters
95
90
80
100
100
100
100
100
98
100
100
98
98


Morningglory
40
98
98
30
100
100
100
100
98
100
98
98
98


Nightshade
98
98
95
—
—
—
—
—
—
—
—
—
—


Nutsedge, Yellow
15
65
35
30
45
95
90
80
15
75
25
95
60


Oat, Wild
80
90
85
—
—
—
—
—
—
—
—
—
—


Oilseed Rape
—
—
—
100
100
100
100
100
100
95
100
98
100


Pigweed
100
100
100
95
100
100
100
100
100
100
100
100
98


Ragweed
40
60
30
35
100
100
100
95
85
90
75
98
85


Russian Thistle
—
90
95
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
40
90
85
25
90
90
90
80
70
90
90
95
95


Soybean
98
90
85
75
90
98
95
85
90
95
45
100
80


Sunflower
10
0
40
—
—
—
—
—
—
—
—
—
—


Surinam Grass
85
100
100
—
—
—
—
—
—
—
—
—
—


Velvetleaf
100
100
100
100
100
100
100
100
100
100
100
100
98


Waterhemp
—
—
—
95
100
100
100
100
100
100
100
100
98


Wheat
40
60
35
0
45
90
90
35
85
90
35
95
60












Compounds





















125 g ai/ha
7
16
18
25
52
58
59
72
73
79
83
84
85
86










Preemergence





















Barnyardgrass
—
—
—
35
100
100
100
100
100
100
90
85
95
95


Bermudagrass
100
98
98
—
—
—
—
—
—
—
—
—
—
—


Blackgrass
50
90
90
85
90
90
90
90
90
90
85
85
90
98


Bromegrass, Downy
45
90
50
—
—
—
—
—
—
—
—
—
—
—


Cocklebur
5
5
—
—
—
—
—
—
—
—
—
—
—
—


Corn
5
25
10
0
60
98
75
65
5
80
15
5
45
80


Crabgrass, Large
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Cupgrass, Woolly
98
98
98
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
98
100
100
75
100
100
100
100
100
100
100
100
100
100


Foxtail, Green
90
90
90
—
—
—
—
—
—
—
—
—
—
—


Galium
100
100
100
100
100
100
100
90
90
90
100
100
85
90


Goosegrass
95
100
95
—
—
—
—
—
—
—
—
—
—
—


Johnsongrass
10
100
80
5
90
100
98
100
75
100
85
85
85
95


Kochia
100
85
80
—
—
—
—
—
—
—
—
—
—
—


Lambsquarters
85
80
65
100
100
100
100
100
98
100
100
100
100
100


Morningglory
10
90
80
5
100
100
100
100
95
100
10
100
20
100


Nightshade
95
80
80
—
—
—
—
—
—
—
—
—
—
—


Nutsedge, Yellow
15
65
25
0
40
90
85
10
5
65
15
40
20
35


Oat, Wild
50
90
80
—
—
—
—
—
—
—
—
—
—
—


Oilseed Rape
—
—
—
100
100
100
100
100
100
95
100
100
98
100


Pigweed
100
100
100
95
100
100
100
100
100
100
100
100
100
100


Ragweed
5
55
10
35
95
100
100
85
85
90
45
85
65
100


Russian Thistle
—
90
95
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
5
80
45
20
80
90
90
40
55
90
50
5
50
35


Soybean
60
90
85
60
90
98
90
80
75
90
75
70
60
85


Sunflower
10
0
0
—
—
—
—
—
—
—
—
—
—
—


Surinam Grass
30
100
100
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Waterhemp
—
—
—
95
100
100
100
100
100
100
100
100
100
100


Wheat
10
35
35
0
30
80
85
30
5
85
0
0
5
35












Compounds





















125 g ai/ha
88
89
90
92
94
97
111
112
116
118
129
132
134
136










Preemergence





















Barnyardgrass
95
100
85
100
100
100
100
90
70
100
90
75
85
100


Bermudagrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Blackgrass
90
50
85
90
90
90
90
95
85
95
90
95
98
80


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
15
5
45
65
55
80
65
20
25
85
30
35
40
15


Crabgrass, Large
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
100
100
100
100
100
100
100
100
95
100
100
98
100
100


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Galium
80
100
98
98
100
95
75
95
100
100
100
90
98
85


Goosegrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Johnsongrass
85
75
80
85
70
90
80
40
70
100
90
35
85
60


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Lambsquarters
100
100
100
98
100
98
100
98
100
100
100
100
100
100


Morningglory
90
98
100
98
90
100
100
75
20
100
75
5
40
60


Nightshade
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Nutsedge, Yellow
5
70
60
75
65
90
50
40
40
70
25
15
10
35


Oat, Wild
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Oilseed Rape
100
98
100
95
98
90
100
100
100
100
100
100
100
100


Pigweed
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Ragweed
60
100
95
85
25
100
100
100
45
100
85
30
50
70


Russian Thistle
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
5
50
50
85
50
90
60
30
35
100
35
30
70
15


Soybean
90
98
95
95
95
98
95
95
70
95
80
55
55
85


Sunflower
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
100
100
100
100
100
100
100
100
100
100
100
100
100
90


Waterhemp
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Wheat
5
5
0
80
5
90
20
10
5
90
15
0
15
0












Compounds





















125 g ai/ha
137
138
141
145
147
150
151
154
164
166
167
170
179
180










Preemergence





















Barnyardgrass
40
95
100
75
100
80
100
100
100
100
100
100
100
100


Bermudagrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Blackgrass
10
90
95
95
90
50
90
90
90
100
90
90
90
90


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
10
25
90
5
35
45
70
10
45
80
60
40
15
65


Crabgrass, Large
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
90
100
100
100
100
100
100
100
100
100
100
100
100
100


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Galium
95
100
100
98
98
100
—
95
95
95
100
100
100
100


Goosegrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Johnsongrass
45
65
100
65
90
80
65
85
80
95
95
85
98
98


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Lambsquarters
100
100
100
100
100
100
100
100
98
98
100
100
100
100


Morningglory
90
35
100
35
100
75
25
85
100
100
100
100
90
100


Nightshade
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Nutsedge, Yellow
10
55
95
10
55
40
25
65
25
80
60
55
15
85


Oat, Wild
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Oilseed Rape
95
100
100
100
100
100
100
100
100
100
98
95
100
100


Pigweed
100
100
100
100
100
100
100
100
98
100
100
100
100
100


Ragweed
95
10
100
70
100
55
100
90
85
95
20
65
10
98


Russian Thistle
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
0
60
100
75
70
50
45
25
98
90
90
90
70
80


Soybean
85
90
98
95
95
90
95
95
95
95
90
55
65
98


Sunflower
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
85
100
100
100
100
70
100
100
100
100
100
100
100
100


Waterhemp
100
100
100
100
100
98
100
100
100
100
100
100
100
100


Wheat
0
5
60
0
25
5
40
5
35
90
50
60
5
50












Compounds





















125 g ai/ha
187
194
200
204
236
240
250
252
253
258
270
273
274
292










Preemergence





















Barnyardgrass
90
100
100
100
100
100
100
100
100
100
100
85
100
100


Bermudagrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Blackgrass
100
90
98
90
90
95
90
95
90
90
95
70
90
90


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
5
15
60
5
90
35
10
70
90
65
55
35
80
45


Crabgrass, Large
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
85
100
100
100
100
100
100
100
100
100
100
90
100
100


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Galium
98
90
100
100
100
100
98
98
95
100
100
98
98
100


Goosegrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Johnsongrass
45
80
98
95
85
45
70
100
100
90
95
80
98
85


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Lambsquarters
100
100
98
95
100
100
100
100
100
98
100
100
98
100


Morningglory
5
95
98
98
98
75
50
100
100
98
100
85
100
70


Nightshade
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Nutsedge, Yellow
5
0
90
60
75
40
5
60
65
100
45
35
95
35


Oat, Wild
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Oilseed Rape
90
90
98
98
100
100
100
100
100
100
100
100
95
98


Pigweed
100
100
100
98
100
65
100
100
100
100
100
100
100
100


Ragweed
55
20
100
5
90
80
75
100
100
90
70
85
75
70


Russian Thistle
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
5
70
85
75
85
50
15
90
80
70
50
60
90
85


Soybean
85
25
95
65
95
98
90
98
98
95
85
65
98
90


Sunflower
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
100
100
100
98
100
85
100
100
100
100
100
85
100
100


Waterhemp
95
100
100
100
100
100
100
100
100
100
100
100
100
100


Wheat
0
0
90
30
60
5
0
45
60
25
5
5
90
15












Compounds





















62 g ai/ha
7
16
18
25
52
58
59
72
73
79
83
84
85
86










Preemergence





















Barnyardgrass
—
—
—
10
95
100
100
100
80
100
45
40
75
40


Bermudagrass
100
98
98
—
—
—
—
—
—
—
—
—
—
—


Blackgrass
10
90
80
5
85
90
85
90
80
90
90
40
10
90


Bromegrass, Downy
5
60
10
—
—
—
—
—
—
—
—
—
—
—


Cocklebur
5
5
0
—
—
—
—
—
—
—
—
—
—
—


Corn
5
15
10
0
5
90
55
25
0
—
0
0
5
30


Crabgrass, Large
98
100
100
85
100
100
100
100
100
100
100
100
100
100


Cupgrass, Woolly
55
90
55
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
80
98
100
60
100
100
98
100
100
100
100
98
90
100


Foxtail, Green
90
90
90
—
—
—
—
—
—
—
—
—
—
—


Galium
100
100
95
90
100
100
100
90
90
90
85
100
50
98


Goosegrass
85
98
85
—
—
—
—
—
—
—
—
—
—
—


Johnsongrass
5
85
30
0
25
100
85
55
35
90
50
40
55
60


Kochia
95
80
60
—
—
—
—
—
—
—
—
—
—
—


Lambsquarters
80
80
50
100
100
100
100
100
98
100
100
100
100
100


Morningglory
0
75
30
5
95
100
100
85
45
100
0
25
0
60


Nightshade
95
65
30
—
—
—
—
—
—
—
—
—
—
—


Nutsedge, Yellow
0
25
15
0
10
85
65
0
0
15
0
5
5
5


Oat, Wild
5
90
50
—
—
—
—
—
—
—
—
—
—
—


Oilseed Rape
—
—
—
98
100
100
100
100
95
95
98
100
90
100


Pigweed
100
100
100
95
100
100
100
100
100
100
100
100
100
100


Ragweed
0
25
0
20
90
100
95
75
75
90
40
60
50
100


Russian Thistle
—
80
0
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
0
30
5
5
55
90
85
10
5
90
30
5
0
30


Soybean
40
90
65
20
85
95
90
55
60
75
60
60
40
75


Sunflower
10
0
0
—
—
—
—
—
—
—
—
—
—
—


Surinam Grass
5
100
30
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
100
100
100
85
100
100
100
95
75
100
100
85
100
100


Waterhemp
—
—
—
95
100
100
100
100
100
100
100
100
100
100


Wheat
5
0
5
0
0
80
50
0
0
35
0
0
0
0












Compounds





















62 g ai/ha
88
89
90
92
94
97
111
112
116
118
129
132
134
135










Preemergence





















Barnyardgrass
35
70
75
100
85
100
90
30
45
100
40
10
60
60


Bermudagrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Blackgrass
60
5
30
70
90
90
40
40
60
90
5
40
85
20


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
5
0
10
5
5
45
5
5
5
70
5
20
40
30


Crabgrass, Large
100
100
98
100
100
100
100
100
100
85
100
98
98
100


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
98
100
75
100
100
100
100
100
85
95
100
70
100
70


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Galium
90
85
100
95
98
98
100
100
100
100
95
90
90
90


Goosegrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Johnsongrass
40
20
20
70
35
90
25
20
55
85
40
0
45
45


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Lambsquarters
100
95
100
100
100
100
100
100
85
100
100
100
100
85


Morningglory
40
95
55
98
40
100
85
65
20
100
45
5
35
80


Nightshade
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Nutsedge, Yellow
5
10
5
50
55
60
15
15
10
25
5
15
0
15


Oat, Wild
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Oilseed Rape
70
95
98
85
98
98
98
95
98
100
100
100
100
95


Pigweed
100
100
98
100
100
100
100
100
100
100
100
70
100
98


Ragweed
5
75
100
50
10
85
100
35
45
100
60
40
55
65


Russian Thistle
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
0
45
0
50
10
85
40
5
10
70
10
5
15
10


Soybean
40
90
65
80
85
95
80
50
40
90
40
5
20
85


Sunflower
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
100
100
98
100
100
100
90
100
100
100
100
100
85
85


Waterhemp
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Wheat
0
0
0
30
0
60
0
0
0
10
0
0
0
0












Compounds





















62 g ai/ha
136
137
138
141
145
147
150
151
154
164
166
167
170
179










Preemergence





















Barnyardgrass
60
10
65
100
50
90
65
70
70
98
100
100
100
90


Bermudagrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Blackgrass
75
5
80
95
85
50
50
10
20
90
90
90
90
40


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
5
5
0
80
0
20
25
15
5
5
40
25
15
5


Crabgrass, Large
100
98
100
100
100
100
100
98
100
100
100
100
100
98


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
80
60
100
100
75
100
100
80
85
100
100
100
98
100


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Galium
30
10
90
100
90
98
90
—
95
95
95
100
100
98


Goosegrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Johnsongrass
20
5
40
100
25
80
70
50
40
75
85
80
70
65


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Lambsquarters
80
100
100
100
100
100
80
100
90
100
98
100
100
100


Morningglory
10
45
10
100
0
95
45
10
50
85
98
50
40
35


Nightshade
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Nutsedge, Yellow
10
5
25
70
0
15
25
5
5
20
35
10
15
10


Oat, Wild
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Oilseed Rape
50
85
100
100
100
100
90
100
100
100
100
90
98
98


Pigweed
40
90
100
100
100
100
100
100
100
100
100
100
100
100


Ragweed
20
80
5
100
100
98
25
85
95
75
95
15
55
0


Russian Thistle
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
0
0
20
75
40
50
30
35
20
65
90
80
75
30


Soybean
50
80
90
90
90
95
45
85
80
65
95
90
45
45


Sunflower
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
30
65
98
100
100
100
60
100
100
100
100
100
80
98


Waterhemp
75
95
100
100
100
100
98
100
100
100
100
100
100
98


Wheat
0
0
5
40
0
0
5
0
0
30
60
5
20
0












Compounds





















62 g ai/ha
180
187
194
200
204
236
240
250
252
253
258
270
273
274










Preemergence





















Barnyardgrass
100
65
85
100
95
98
60
50
100
100
90
90
25
100


Bermudagrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Blackgrass
90
30
50
95
80
90
95
70
90
90
90
70
5
90


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
30
5
0
5
0
10
5
0
40
35
45
20
45
85


Crabgrass, Large
100
100
98
100
100
100
100
98
100
100
100
100
95
100


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
100
85
90
100
98
100
100
100
100
98
100
100
75
100


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Galium
100
90
90
100
100
100
100
70
90
100
100
95
95
98


Goosegrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Johnsongrass
75
30
25
98
80
60
10
35
80
60
75
40
55
95


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Lambsquarters
100
98
100
98
98
100
100
100
100
100
98
100
100
100


Morningglory
100
0
0
95
98
55
75
50
95
98
45
55
55
100


Nightshade
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Nutsedge, Yellow
65
5
0
40
0
60
15
—
40
20
95
15
5
85


Oat, Wild
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Oilseed Rape
100
90
30
98
95
100
100
100
100
100
100
100
80
95


Pigweed
100
90
100
100
100
100
55
100
100
100
100
100
100
100


Ragweed
80
45
10
100
5
85
100
40
98
85
80
45
55
35


Russian Thistle
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
50
0
20
70
35
45
0
5
60
35
25
10
0
90


Soybean
98
55
20
90
35
90
85
65
95
95
75
25
40
95


Sunflower
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
100
95
75
100
85
100
80
100
100
100
100
98
85
100


Waterhemp
100
85
100
100
100
98
100
100
100
100
98
100
98
100


Wheat
5
0
0
65
5
0
0
0
0
0
5
0
0
90














Compound



62 g ai/ha
292











Preemergence










Barnyardgrass
85



Bermudagrass
—



Blackgrass
90



Bromegrass, Downy
—



Cocklebur
—



Corn
10



Crabgrass, Large
100



Cupgrass, Woolly
—



Foxtail, Giant
100



Foxtail, Green
—



Galium
100



Goosegrass
—



Johnsongrass
40



Kochia
—



Lambsquarters
98



Morningglory
35



Nightshade
—



Nutsedge, Yellow
0



Oat, Wild
—



Oilseed Rape
98



Pigweed
100



Ragweed
35



Russian Thistle
—



Ryegrass, Italian
10



Soybean
85



Sunflower
—



Surinam Grass
—



Velvetleaf
98



Waterhemp
100



Wheat
10













Compounds





















31 g ai/ha
7
16
18
25
52
58
59
72
73
79
83
84
85
86










Preemergence





















Barnyardgrass
—
—
—
0
50
98
80
75
60
100
5
25
15
10


Bermudagrass
85
95
95
—
—
—
—
—
—
—
—
—
—
—


Blackgrass
5
85
10
0
—
90
5
50
0
90
5
5
5
20


Bromegrass, Downy
0
30
0
—
—
—
—
—
—
—
—
—
—
—


Cocklebur
0
0
—
—
—
—
—
—
—
—
—
—
—
—


Corn
0
0
0
0
5
60
—
—
0
40
0
0
10
25


Crabgrass, Large
80
98
75
55
100
100
100
100
100
100
85
98
90
100


Cupgrass, Woolly
15
75
40
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
40
95
65
10
100
100
95
100
85
98
75
55
35
75


Foxtail, Green
50
90
85
—
—
—
—
—
—
—
—
—
—
—


Galium
85
95
90
80
100
100
100
80
85
90
0
90
0
80


Goosegrass
65
75
75
—
—
—
—
—
—
—
—
—
—
—


Johnsongrass
0
0
30
0
15
85
60
35
10
75
0
20
20
20


Kochia
55
50
15
—
—
—
—
—
—
—
—
—
—
—


Lambsquarters
80
20
30
100
100
100
100
98
60
100
100
85
100
100


Morningglory
0
10
10
0
55
100
95
15
45
95
0
10
0
25


Nightshade
80
20
—
—
—
—
—
—
—
—
—
—
—
—


Nutsedge, Yellow
0
15
10
—
0
70
—
0
0
10
0
0
0
0


Oat, Wild
0
50
0
—
—
—
—
—
—
—
—
—
—
—


Oilseed Rape
—
—
—
85
100
100
90
65
85
90
95
85
40
100


Pigweed
100
100
100
80
100
100
100
100
100
100
100
100
40
100


Ragweed
0
0
0
20
90
85
90
55
—
90
35
60
0
20


Russian Thistle
—
0
0
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
0
0
0
0
5
90
50
5
0
40
0
5
0
0


Soybean
15
75
25
0
5
90
85
40
—
75
10
20
15
45


Sunflower
0
0
0
—
—
—
—
—
—
—
—
—
—
—


Surinam Grass
0
25
20
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
40
98
60
75
75
100
100
60
60
90
100
60
80
50


Waterhemp
—
—
—
80
100
100
100
100
100
100
100
75
85
100


Wheat
0
0
0
0
0
45
0
0
0
10
0
0
0
0












Compounds





















31 g ai/ha
88
89
90
92
94
97
111
112
116
118
129
132
134
135










Preemergence





















Barnyardgrass
5
35
5
75
10
95
55
5
25
80
15
0
15
15


Bermudagrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Blackgrass
5
0
5
5
20
70
10
30
10
80
50
5
45
5


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
5
0
0
0
5
5
5
0
0
40
5
10
30
5


Crabgrass, Large
70
100
98
100
98
100
100
100
100
80
95
85
98
100


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
65
35
45
98
65
100
100
85
10
75
80
55
65
70


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Galium
50
100
5
85
98
90
100
98
100
95
80
0
0
80


Goosegrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Johnsongrass
0
0
10
5
25
40
5
5
25
25
10
0
25
5


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Lambsquarters
100
80
98
98
85
98
100
100
95
100
40
55
100
85


Morningglory
5
35
20
25
30
98
45
15
5
75
35
0
20
50


Nightshade
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Nutsedge, Yellow
0
5
0
5
0
20
0
5
5
5
0
0
0
0


Oat, Wild
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Oilseed Rape
100
80
80
80
98
85
90
90
5
100
85
85
45
95


Pigweed
100
90
85
85
100
100
95
100
100
100
100
45
100
80


Ragweed
0
55
60
5
0
35
50
0
5
100
20
10
25
55


Russian Thistle
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
0
5
0
10
0
60
0
0
0
40
0
0
5
5


Soybean
5
45
35
65
50
90
60
35
25
75
10
0
15
65


Sunflower
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
98
70
65
90
100
95
60
70
70
100
70
85
35
45


Waterhemp
100
100
100
98
100
100
100
98
100
100
100
98
100
100


Wheat
0
0
0
0
0
10
30
0
0
0
0
0
0
0












Compounds





















31 g ai/ha
136
137
138
141
145
147
150
151
154
164
166
167
170
179










Preemergence





















Barnyardgrass
10
5
25
100
0
80
20
5
25
70
100
85
55
10


Bermudagrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Blackgrass
0
0
20
95
65
40
10
0
10
50
85
30
80
50


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
0
5
0
20
0
0
0
5
0
5
25
5
5
5


Crabgrass, Large
100
70
90
100
75
100
98
85
90
85
100
98
95
90


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
5
5
90
100
55
100
75
35
70
95
100
95
85
85


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Galium
0
5
90
98
85
98
80
—
95
100
100
100
98
95


Goosegrass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Johnsongrass
0
0
5
70
0
35
30
5
0
20
40
40
25
0


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Lambsquarters
10
30
100
100
100
100
100
100
85
98
98
100
98
100


Morningglory
30
10
0
90
0
80
5
0
25
55
70
35
15
0


Nightshade
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Nutsedge, Yellow
0
0
5
30
0
5
0
0
5
5
10
10
0
0


Oat, Wild
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Oilseed Rape
0
60
100
100
100
100
5
100
100
98
100
80
80
95


Pigweed
50
75
95
100
100
100
70
100
100
100
100
100
100
100


Ragweed
25
25
5
100
75
100
—
70
85
10
65
30
25
5


Russian Thistle
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
0
0
0
45
5
35
5
0
5
40
40
40
10
10


Soybean
30
40
55
85
45
80
35
65
70
25
90
70
10
10


Sunflower
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Velvetleaf
—
25
80
100
100
100
10
100
100
100
100
85
55
75


Waterhemp
40
100
100
100
100
98
50
100
95
100
100
100
100
98


Wheat
0
0
0
5
0
0
0
0
0
5
15
0
10
0














Compound



31 g ai/ha
292











Preemergence










Barnyardgrass
15



Bermudagrass
—



Blackgrass
70



Bromegrass, Downy
—



Cocklebur
—



Corn
5



Crabgrass, Large
100



Cupgrass, Woolly
—



Foxtail, Giant
100



Foxtail, Green
—



Galium
98



Goosegrass
—



Johnsongrass
5



Kochia
—



Lambsquarters
80



Morningglory
30



Nightshade
—



Nutsedge, Yellow
0



Oat, Wild
—



Oilseed Rape
80



Pigweed
100



Ragweed
35



Russian Thistle
—



Ryegrass, Italian
0



Soybean
40



Sunflower
—



Surinam Grass
—



Velvetleaf
35



Waterhemp
100



Wheat
0













Compounds





















16 g ai/ha
83
84
85
86
88
89
90
92
94
97
111
112
116
118










Preemergence





















Barnyardgrass
5
0
0
5
5
5
0
5
5
35
5
0
0
20


Blackgrass
0
0
0
0
0
0
5
0
5
0
20
0
0
35


Corn
0
0
5
0
5
0
0
0
5
0
5
0
0
10


Crabgrass, Large
65
45
65
85
45
80
25
90
25
98
98
35
5
30


Foxtail, Giant
5
5
20
35
5
5
5
30
5
60
15
15
0
25


Galium
0
80
0
90
0
30
5
80
80
85
90
55
0
95


Johnsongrass
0
0
15
10
0
0
5
0
0
10
0
0
0
0


Lambsquarters
100
75
65
100
70
45
100
65
40
95
50
98
10
100


Morningglory
0
0
0
10
0
45
0
10
0
40
20
5
0
40


Nutsedge, Yellow
0
0
0
0
0
0
35
5
0
10
0
0
0
0


Oilseed Rape
75
50
0
25
10
80
60
80
85
85
60
65
0
98


Pigweed
85
85
50
90
100
55
40
90
90
100
75
100
75
90


Ragweed
0
0
0
5
0
40
10
10
0
35
10
0
0
70


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Soybean
5
0
0
35
0
30
25
30
35
50
30
10
0
60


Velvetleaf
60
50
35
20
15
20
35
30
40
40
60
65
20
100


Waterhemp
75
100
55
100
98
80
85
95
80
100
100
90
100
85


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
0












Compounds





















16 g ai/ha
129
132
134
135
136
137
138
141
145
147
150
151
154
164










Preemergence





















Barnyardgrass
5
0
0
0
0
0
10
80
0
10
5
5
5
15


Blackgrass
0
0
0
0
0
0
5
80
0
0
0
0
0
0


Corn
0
0
0
10
5
0
0
5
0
0
0
0
5
0


Crabgrass, Large
75
65
60
60
35
10
100
100
70
98
70
5
75
75


Foxtail, Giant
0
5
10
5
0
35
30
90
10
70
5
5
5
40


Galium
50
0
0
0
0
5
90
98
0
90
0
—
80
75


Johnsongrass
0
0
20
0
0
0
0
30
0
10
0
0
0
5


Lambsquarters
50
75
60
30
—
100
100
85
55
100
10
100
70
70


Morningglory
5
25
5
50
20
25
0
75
0
40
0
0
10
10


Nutsedge, Yellow
0
100
0
0
0
0
5
—
0
0
0
0
0
0


Oilseed Rape
50
20
20
55
0
50
80
100
95
100
0
95
98
70


Pigweed
98
30
100
85
0
75
85
100
25
100
55
100
85
98


Ragweed
0
10
0
40
0
45
0
85
20
75
0
55
75
0


Ryegrass, Italian
0
0
0
0
0
0
0
40
0
0
0
0
0
0


Soybean
10
0
0
20
20
10
20
65
35
85
0
35
50
0


Velvetleaf
35
75
30
40
5
40
60
100
55
100
5
85
85
50


Waterhemp
100
85
85
75
0
100
100
100
95
100
20
95
100
85


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
0












Compounds





















16 g ai/ha
166
167
170
179
180
187
236
240
250
252
253
258
270
273










Preemergence





















Barnyardgrass
85
5
10
5
60
5
10
5
5
10
30
45
0
0


Blackgrass
40
30
0
0
20
0
5
0
0
10
0
0
0
0


Corn
0
0
0
0
5
0
0
5
0
10
0
0
0
0


Crabgrass, Large
100
75
25
55
100
5
90
75
75
60
85
100
50
90


Foxtail, Giant
100
35
80
40
90
0
35
10
5
35
35
75
5
0


Galium
98
98
95
90
80
30
90
5
0
80
70
80
70
0


Johnsongrass
5
5
0
0
0
0
5
5
0
5
15
5
0
0


Lambsquarters
90
75
90
85
85
5
98
70
90
98
100
65
80
35


Morningglory
15
30
0
10
35
0
0
15
0
45
40
10
0
5


Nutsedge, Yellow
0
0
0
0
5
0
0
0
0
0
0
5
0
0


Oilseed Rape
90
80
70
60
55
70
80
70
100
80
75
80
95
0


Pigweed
100
100
100
100
85
45
100
5
85
98
100
100
100
55


Ragweed
50
15
85
0
20
55
15
10
15
40
35
0
0
10


Ryegrass, Italian
5
5
5
0
5
0
0
0
0
0
0
0
0
0


Soybean
60
10
5
0
90
5
35
40
—
65
40
35
0
5


Velvetleaf
80
45
25
60
75
25
65
25
100
75
55
80
0
10


Waterhemp
100
100
100
90
90
25
98
50
85
100
100
100
80
45


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
0














Compounds

Compound













16 g ai/ha
274
292
8 g ai/ha
135











Preemergence













Barnyardgrass
90
0
Barnyardgrass
0



Blackgrass
50
0
Blackgrass
0



Corn
5
0
Corn
5



Crabgrass, Large
100
100
Crabgrass, Large
45



Foxtail, Giant
98
45
Foxtail, Giant
0



Galium
90
80
Galium
0



Johnsongrass
10
0
Johnsongrass
0



Lambsquarters
100
35
Morningglory
5



Morningglory
35
25
Nutsedge, Yellow
0



Nutsedge, Yellow
20
0
Oilseed Rape
30



Oilseed Rape
80
70
Pigweed
50



Pigweed
100
100
Ragweed
0



Ragweed
10
25
Ryegrass, Italian
0



Ryegrass, Italian
25
0
Soybean
10



Soybean
35
5
Velvetleaf
5



Velvetleaf
80
15
Waterhemp
55



Waterhemp
100
100
Wheat
0



Wheat
20
0

















Compound

Compound



2000 g ai/ha
80
500 g ai/ha
80











Flood












Barnyardgrass
0
Barnyardgrass
0



Ducksalad
80
Ducksalad
75



Rice
0
Rice
0



Sedge, Umbrella
85
Sedge, Umbrella
0















Compound



1000 g ai/ha
80











Flood










Barnyardgrass
0



Ducksalad
80



Rice
0



Sedge, Umbrella
60













Compounds





















250 g ai/ha
3
8
18
25
26
34
40
59
62
65
80
81
89
97










Flood





















Barnyardgrass
0
0
20
0
0
10
15
40
40
0
0
0
20
0


Ducksalad
85
70
90
90
85
75
60
95
100
85
50
90
80
80


Rice
0
10
10
0
0
0
0
20
25
0
0
0
0
0


Sedge, Umbrella
70
85
90
85
85
70
75
95
100
85
0
90
70
80












Compounds





















250 g ai/ha
120
141
150
164
167
177
179
184
185
188
191
192
194
200










Flood





















Barnyardgrass
85
20
0
0
0
0
0
0
0
0
20
0
0
25


Ducksalad
90
100
75
95
80
95
95
75
40
60
80
75
100
80


Rice
60
60
0
0
0
10
10
0
15
0
0
0
10
0


Sedge, Umbrella
85
100
85
95
85
85
80
75
85
75
98
85
95
90













Compounds














250 g ai/ha
231
234
236
270











Flood













Barnyardgrass
0
0
20
60



Ducksalad
75
30
90
95



Rice
0
0
20
30



Sedge, Umbrella
80
40
80
95













Compounds





















125 g ai/ha
3
8
18
25
26
34
40
59
62
65
81
89
97
120










Flood





















Barnyardgrass
0
0
10
0
0
0
15
30
0
0
0
15
0
60


Ducksalad
70
50
85
85
65
20
40
95
85
85
60
65
75
80


Rice
0
10
0
0
0
0
0
20
15
0
0
0
0
15


Sedge, Umbrella
20
75
85
80
75
0
75
90
90
75
70
50
75
60












Compounds





















125 g ai/ha
141
150
164
167
177
179
184
185
188
191
192
194
200
203










Flood





















Barnyardgrass
15
0
0
0
0
0
0
0
0
0
0
0
0
50


Ducksalad
95
70
75
60
85
85
30
0
40
75
70
90
20
70


Rice
40
0
0
0
10
10
0
0
0
0
0
10
0
20


Sedge, Umbrella
75
75
75
80
60
40
50
50
50
85
50
85
90
85












Compounds














125 g ai/ha
231
234
236
270
293











Flood














Barnyardgrass
0
0
0
45
0



Ducksalad
70
0
80
80
75



Rice
0
0
10
0
0



Sedge, Umbrella
70
0
60
60
85













Compounds





















62 g ai/ha
3
8
18
25
26
34
40
59
62
65
81
89
97
120










Flood





















Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ducksalad
50
40
80
70
30
0
0
75
70
30
40
0
40
40


Rice
0
0
0
0
0
0
0
15
15
0
0
0
0
0


Sedge, Umbrella
0
50
75
50
0
0
75
80
50
65
50
0
60
0












Compounds





















62 g ai/ha
141
150
164
167
177
179
184
185
188
191
192
194
200
203










Flood





















Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
0
0
50


Ducksalad
80
40
0
50
60
60
30
0
0
50
0
80
0
50


Rice
0
0
0
0
0
0
0
0
0
0
0
10
0
20


Sedge, Umbrella
40
50
20
70
0
0
0
50
0
60
0
75
80
75












Compounds














62 g ai/ha
231
234
236
270
293











Flood














Barnyardgrass
0
0
0
30
0



Ducksalad
30
0
40
60
40



Rice
0
0
0
0
0



Sedge, Umbrella
50
0
20
25
75













Compounds





















31 g ai/ha
3
8
18
25
26
34
40
59
62
65
81
97
120
141










Flood





















Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ducksalad
0
0
80
0
0
0
0
50
30
0
30
0
0
65


Rice
0
0
0
0
0
0
0
0
15
0
0
0
0
0


Sedge, Umbrella
0
0
70
0
0
0
50
60
0
50
0
60
0
0












Compounds





















31 g ai/ha
150
164
167
177
179
184
185
188
191
192
194
200
203
231










Flood





















Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
0
40
0


Ducksalad
0
0
0
20
20
0
0
0
30
0
65
0
0
0


Rice
0
0
0
0
0
0
0
0
0
0
10
0
0
0


Sedge, Umbrella
0
0
60
0
0
0
0
0
40
0
50
0
50
0













Compounds














31 g ai/ha
234
236
270
293











Flood













Barnyardgrass
0
0
0
0



Ducksalad
0
0
20
30



Rice
0
0
0
0



Sedge, Umbrella
0
0
0
60










Test D

Seeds of plant species selected from bluegrass (annual bluegrass, Poa annua), blackgrass (Alopecurus myosuroides), canarygrass (littleseed canarygrass, Phalaris minor), chickweed (common chickweed, Stellaria media), galium (catchweed bedstraw, Galium aparine), bromegrass, downy (downy bromegrass, Bromus tectorum), field poppy (Papaver rhoeas), field violet (Viola arvensis), green foxtail (Setaria viridis), deadnettle (henbit deadnettle, Lamium amplexicaule), Italian ryegrass (Lolium multiflorum), kochia (Kochia scoparia), lambsquarters (Chenopodium album), oilseed rape (Brassica napus), pigweed (Amaranthus retroflexus), chamomile (scentless chamomile, Matricaria inodora), Russian thistle (Salsola kali), speedwell (bird's-eye speedwell, Veronica persica), spring barley (Hordeum vulgare), spring wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), wild mustard (Sinapis arvensis), wild oat (Avena fatua), wild radish (Raphanus raphanistrum), windgrass (Apera spica-venti), winter barley (Hordeum vulgare), and winter wheat (Triticum aestivum) were planted into a silt loam soil and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant.
At the same time, these species were planted in pots containing Redi-Earth® planting medium (Scotts Company, 14111 Scottslawn Road, Marysville, Ohio 43041) comprising spaghnum peat moss, vermiculite, wetting agent and starter nutrients and treated with postemergence applications of the test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage). Treated plants and controls were maintained in a controlled growth environment for 7 to 21 days after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table D, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.









TABLE D









Postemergence










250 g ai/ha
125 g ai/ha



Compounds
Compounds

























3
7
18
52
58
59
284
3
7
18
25
52
58
59
138
141
145





Barley, Spring
10
5
25
20
40
35
25
0
5
15
15
15
30
20
15
25
10


Barley, Winter
0
0
20
20
50
25
25
0
0
15
5
15
25
15
10
35
15


Blackgrass
10
25
35
65
90
70
35
0
10
20
25
40
70
40
15
55
35


Bluegrass
10
15
40
25
55
40
45
0
10
40
55
15
45
20
10
40
45


Bromegrass, Downy
0
5
15
25
35
30
45
0
5
20
30
20
35
25
5
45
25


Buckwheat, Wild
80
100
95
100
100
100
100
60
85
100
100
100
100
100
80
100
100


Canarygrass
10
25
35
60
70
35
25
0
10
20
40
50
50
35
15
55
35


Chamomile
0
0
10
15
35
15
10
0
0
10
5
20
35
10
0
20
10


Chickweed
40
80
95
90
100
95
100
30
60
60
100
85
100
95
55
100
80


Deadnettle
20
40
100
100
100
100
100
10
30
90
55
70
100
100
25
100
85


Field Poppy
0
60
100
100
100
100
100
—
50
100
75
80
100
100
75
85
100


Field Violet
20
70
90
100
100
100
100
5
70
80
100
100
100
100
75
95
75


Foxtail, Green
10
20
25
75
80
80
85
0
10
20
20
40
65
50
30
100
50


Galium
75
90
70
100
100
95
95
45
80
65
90
95
100
95
75
98
75


Kochia
55
100
100
90
95
95
100
25
100
100
100
90
95
95
75
100
75


Lambsquarters
85
100
95
95
90
95
100
80
90
95
95
75
95
80
60
98
85


Mustard, Wild
85
98
100
100
100
100
100
35
95
80
100
95
100
100
75
100
100


Oat, Wild
0
25
25
35
55
50
35
0
10
20
50
30
35
35
10
30
25


Oilseed Rape
95
100
100
95
95
100
100
90
100
100
55
85
95
75
75
100
95


Pigweed
90
100
95
95
100
95
100
70
100
95
100
85
100
95
90
100
100


Radish, Wild
75
—
100
90
95
85
100
50
—
100
100
80
90
80
90
100
100


Russian Thistle
20
70
100
—
—
—
95
10
30
60
—
—
—
—
—
95
65


Ryegrass, Italian
0
0
15
35
65
50
15
0
0
10
15
20
50
40
5
25
15


Speedwell
75
100
100
100
100
100
100
60
100
100
100
100
100
100
75
100
100


Wheat, Spring
0
10
25
15
35
25
35
0
10
20
20
10
20
20
15
35
15


Wheat, Winter
0
10
20
25
40
20
25
0
10
15
10
20
25
20
15
50
15


Windgrass
10
25
10
40
90
45
30
0
10
10
35
25
55
35
20
60
15












Postemergence










125 g ai/ha
62 g ai/ha



Compound
Compounds

























166
178
245
274
284
3
7
18
25
52
58
59
138
141
145
166
178





Barley, Spring
45
10
30
35
20
0
0
10
10
15
20
20
10
25
5
30
5


Barley, Winter
35
10
20
30
20
0
0
10
5
10
15
15
5
25
15
25
5


Blackgrass
65
—
25
30
30
0
5
15
10
30
45
30
10
35
25
40
25


Bluegrass
65
55
30
30
40
0
0
30
50
20
35
15
5
35
30
55
35


Bromegrass, Downy
50
20
30
40
45
0
0
15
20
20
30
20
5
30
25
35
10


Buckwheat, Wild
100
85
90
100
100
50
60
70
100
95
100
100
65
100
60
95
75


Canarygrass
55
35
35
30
25
0
5
15
25
35
40
30
10
35
25
50
20


Chamomile
15
5
40
25
10
0
0
5
5
15
25
10
0
15
10
10
5


Chickweed
90
75
98
80
90
25
20
45
75
70
90
75
40
95
35
80
65


Deadnettle
70
65
100
70
100
10
20
75
35
70
100
75
15
100
90
65
50


Field Poppy
75
75
100
80
100
0
50
75
60
75
85
65
40
90
55
80
65


Field Violet
85
70
90
85
100
5
70
65
100
100
100
100
65
85
65
70
65


Foxtail, Green
35
35
45
45
50
0
0
15
15
20
40
35
20
45
20
20
30


Galium
90
80
98
85
85
40
70
70
75
80
100
80
75
98
40
80
75


Kochia
95
85
90
95
100
5
100
90
85
90
95
95
55
100
65
90
75


Lambsquarters
95
85
95
95
100
60
80
90
95
75
90
85
60
95
85
95
75


Mustard, Wild
100
100
98
100
100
35
75
70
100
80
100
95
75
100
75
85
75


Oat, Wild
40
25
10
40
25
0
0
15
40
35
35
30
5
15
15
35
25


Oilseed Rape
100
90
75
75
100
80
95
100
60
65
85
65
75
100
75
95
80


Pigweed
95
90
100
95
100
70
100
75
100
85
100
100
90
100
95
95
85


Radish, Wild
95
80
85
90
100
40
—
100
100
70
70
70
80
100
98
95
70


Russian Thistle
—
—
80
—
85
10
30
50
—
—
—
—
—
85
55
—
—


Ryegrass, Italian
40
15
20
35
15
0
0
5
10
5
20
10
0
20
10
25
5


Speedwell
100
100
100
100
100
45
100
100
100
95
100
75
75
100
100
100
100


Wheat, Spring
35
5
20
25
30
0
0
15
15
10
15
15
5
25
20
25
0


Wheat, Winter
40
10
10
30
20
0
0
10
5
15
20
15
5
20
10
30
0


Windgrass
55
20
25
35
30
0
0
10
20
20
35
25
15
50
5
35
15












Postemergence










62 g ai/ha
31 g ai/ha



Compounds
Compounds

























245
274
284
3
7
18
25
52
58
59
138
141
145
166
178
245
274





Barley, Spring
20
30
15
0
0
5
5
10
15
10
10
20
0
20
5
20
25


Barley, Winter
20
25
15
0
0
10
0
10
10
10
5
20
15
15
0
15
20


Blackgrass
20
20
25
0
5
15
5
30
20
25
5
25
25
20
10
10
15


Bluegrass
15
30
35
0
0
25
35
15
25
15
5
20
10
40
30
20
25


Bromegrass, Downy
25
35
40
0
0
15
15
15
25
20
0
20
25
20
5
20
25


Buckwheat, Wild
75
100
100
10
30
55
85
80
90
80
70
100
30
95
75
70
85


Canarygrass
25
25
20
0
0
15
20
35
35
20
10
25
15
35
15
20
20


Chamomile
45
25
0
0
0
10
0
10
10
5
0
20
0
5
0
30
10


Chickweed
95
70
85
0
10
40
65
60
70
70
20
90
30
65
60
75
65


Deadnettle
100
60
100
10
10
65
35
65
80
70
5
100
85
60
45
100
45


Field Poppy
80
40
70
0
20
75
25
60
80
70
35
95
25
60
55
95
40


Field Violet
90
70
85
5
20
80
75
100
100
100
50
75
45
65
60
80
75


Foxtail, Green
35
25
10
0
0
10
10
15
20
20
20
20
15
15
20
20
20


Galium
90
75
85
30
40
60
65
70
70
75
70
98
35
75
75
75
70


Kochia
90
90
100
5
70
85
70
80
95
95
40
85
50
65
70
70
70


Lambsquarters
85
95
98
20
70
50
80
80
75
90
60
95
70
90
70
80
80


Mustard, Wild
100
100
100
20
50
90
80
70
85
100
75
100
70
80
75
70
75


Oat, Wild
10
35
25
0
0
10
35
20
30
25
0
10
10
30
25
0
30


Oilseed Rape
60
65
70
80
80
70
75
55
55
65
70
95
60
65
65
45
55


Pigweed
100
95
100
70
90
75
100
80
90
100
70
98
90
85
80
95
95


Radish, Wild
55
70
100
30
—
90
60
65
65
35
65
95
100
70
65
45
70


Russian Thistle
70
—
75
10
0
5
—
—
—
—
—
40
55
—
—
75
—


Ryegrass, Italian
20
35
10
0
0
5
5
5
10
10
0
15
0
20
0
10
25


Speedwell
100
85
75
30
70
100
90
70
100
100
70
100
100
85
80
100
100


Wheat, Spring
10
15
25
0
0
10
5
5
10
10
5
20
15
10
0
10
15


Wheat, Winter
10
20
25
0
0
5
0
10
15
10
0
5
10
15
0
10
20


Windgrass
15
35
20
0
0
10
15
15
20
15
0
10
5
25
10
15
25












Postemergence










31 g ai/ha
16 g ai/ha



Compound
Compounds




















284
3
7
18
25
138
141
145
166
178
245
274





Barley, Spring
5
50
0
5
0
10
10
0
10
0
10
20


Barley, Winter
15
50
0
10
0
5
20
5
5
0
25
10


Blackgrass
20
70
0
10
0
5
10
5
15
5
5
10


Bluegrass
25
40
0
15
5
0
5
15
20
20
10
20


Bromegrass, Downy
30
50
0
15
5
0
15
10
15
5
20
20


Buckwheat, Wild
100
50
20
60
80
65
100
10
70
65
70
65


Canarygrass
20
30
0
10
10
5
10
0
20
5
0
15


Chamomile
0
0
0
5
0
0
10
0
5
0
30
5


Chickweed
80
40
10
15
60
20
70
15
55
55
45
65


Deadnettle
70
10
10
50
15
5
100
85
40
40
100
50


Field Poppy
65
10
10
80
20
30
40
35
40
45
90
25


Field Violet
100
20
10
55
100
25
45
30
60
50
25
—


Foxtail, Green
10
10
0
10
5
20
15
5
10
15
10
15


Galium
70
40
20
40
55
70
95
35
70
75
70
70


Kochia
100
20
30
35
60
25
70
35
65
60
25
60


Lambsquarters
85
25
70
15
70
55
80
65
80
65
65
75


Mustard, Wild
100
75
20
60
65
65
80
65
75
70
80
70


Oat, Wild
20
70
0
10
20
5
5
5
25
20
0
20


Oilseed Rape
65
90
75
35
100
70
75
55
60
60
30
40


Pigweed
100
70
70
65
90
65
98
95
80
75
95
75


Radish, Wild
75
70
—
95
70
60
90
95
70
60
35
70


Russian Thistle
65
0
0
10
—
—
40
25
—
—
55
—


Ryegrass, Italian
10
60
0
5
0
5
5
0
10
0
0
15


Speedwell
70
60
30
100
70
70
100
100
70
70
100
75


Wheat, Spring
15
60
0
10
0
5
15
10
5
0
10
10


Wheat, Winter
10
65
0
5
0
0
5
5
5
0
5
10


Windgrass
20
70
0
5
10
0
5
0
15
5
10
15












Preemergence










250 g ai/ha
125 g ai/ha



Compounds
Compounds

























3
7
18
52
58
59
284
3
7
18
25
52
58
59
138
141
145





Barley, Spring
0
0
30
50
100
75
35
0
0
0
0
10
85
50
15
90
20


Barley, Winter
20
—
25
35
100
80
20
10
—
15
5
5
80
40
15
90
60


Blackgrass
0
15
100
95
100
85
65
0
0
100
55
30
100
70
30
95
90


Bluegrass
40
40
100
60
100
85
25
20
30
100
15
10
100
35
10
90
85


Bromegrass, Downy
0
0
50
0
75
40
10
0
0
10
0
0
35
10
10
95
55


Buckwheat, Wild
100
90
100
100
100
100
100
60
80
100
50
100
100
100
75
100
100


Canarygrass
25
25
100
55
100
100
60
0
0
100
30
35
100
65
40
100
80


Chamomile
40
25
55
80
100
85
100
20
20
50
15
60
80
95
—
100
100


Chickweed
90
95
100
100
100
95
30
—
90
90
100
100
100
100
100
100
100


Deadnettle
50
80
100
100
100
100
100
40
20
70
100
100
100
100
30
100
100


Field Poppy
80
100
100
100
100
100
100
70
60
95
100
90
100
100
100
100
100


Field Violet
85
80
90
100
100
100
100
85
70
85
60
100
100
100
75
100
100


Foxtail, Green
30
20
100
100
100
100
80
10
0
95
50
100
100
100
100
100
85


Galium
100
40
100
70
100
100
25
70
30
100
65
75
100
60
100
100
90


Kochia
50
70
100
95
95
100
95
30
0
100
100
95
95
100
55
100
100


Lambsquarters
50
60
100
100
100
100
100
25
40
100
95
100
100
95
100
100
100


Mustard, Wild
100
100
100
100
100
100
100
90
90
90
100
90
100
100
100
100
100


Oat, Wild
10
10
30
20
100
55
50
0
10
5
15
0
60
20
0
98
75


Oilseed Rape
100
100
100
100
100
100
10
100
100
100
70
100
100
100
65
100
100


Pigweed
100
90
100
100
100
100
100
80
90
100
100
100
100
100
100
100
100


Radish, Wild
95
—
100
100
100
100
35
90
—
100
100
95
100
95
85
100
100


Russian Thistle
40
0
95
—
—
—
30
40
0
40
—
—
—
—
—
100
50


Ryegrass, Italian
0
5
50
50
100
70
30
0
0
25
10
5
100
60
10
75
65


Speedwell
100
100
—
100
100
100
100
100
100
—
—
100
100
100
100
100
100


Wheat, Spring
0
0
15
30
100
55
30
0
0
5
0
0
75
40
15
75
20


Wheat, Winter
0
10
40
35
90
35
25
0
5
5
0
25
50
5
5
60
20


Windgrass
20
30
100
100
100
100
55
10
0
100
80
100
100
100
15
100
80












Preemergence










125 g ai/ha
62 g ai/ha



Compounds
Compounds

























166
178
245
274
284
3
7
18
25
52
58
59
138
141
145
166
178





Barley, Spring
60
—
35
15
25
0
0
5
0
10
50
5
10
65
15
30
—


Barley, Winter
50
—
40
55
15
0
—
15
0
0
35
10
5
65
20
35
—


Blackgrass
95
85
65
95
35
0
0
50
25
5
55
55
25
90
80
70
35


Bluegrass
100
70
20
70
20
0
0
70
0
0
50
10
0
90
40
65
20


Bromegrass, Downy
50
10
40
35
0
0
0
5
0
0
15
0
0
85
50
25
0


Buckwheat, Wild
100
100
35
100
70
0
75
80
25
50
100
100
55
100
80
100
100


Canarygrass
100
95
35
85
35
0
0
65
20
0
55
15
20
100
75
70
60


Chamomile
55
60
100
65
100
0
0
520
15
65
50
15
—
70
98
50
55


Chickweed
100
90
100
100
20
0
10
—
100
100
100
100
100
100
100
95
85


Deadnettle
100
100
15
100
75
40
10
55
5
75
100
100
20
98
70
100
75


Field Poppy
100
85
100
100
100
40
30
85
75
80
100
100
100
100
100
100
85


Field Violet
100
100
100
100
100
80
20
85
30
95
100
85
70
100
100
100
90


Foxtail, Green
100
95
35
100
10
10
0
50
20
60
100
100
20
100
25
100
5


Galium
100
60
85
100
20
10
20
80
50
20
100
95
90
100
85
100
45


Kochia
100
100
75
100
100
30
0
75
55
95
95
80
35
100
100
95
85


Lambsquarters
100
85
100
100
100
0
30
100
80
100
100
100
60
100
100
100
80


Mustard, Wild
100
95
100
100
90
80
80
100
80
55
100
100
100
100
95
100
95


Oat, Wild
75
25
15
25
20
0
0
0
0
0
25
0
0
80
55
55
10


Oilseed Rape
100
100
100
75
10
70
25
100
60
80
100
60
50
100
100
100
—


Pigweed
100
100
100
100
100
40
90
100
100
100
100
100
100
100
100
100
100


Radish, Wild
100
100
85
85
0
60
—
100
90
80
100
100
70
100
85
100
100


Russian Thistle
—
—
70
—
20
30
0
25
—
—
—
—
—
75
30
—
—


Ryegrass, Italian
85
20
40
70
0
0
0
20
10
0
35
5
0
70
25
60
15


Speedwell
100
100
100
100
100
100
100
—
—
100
100
100
100
100
100
100
100


Wheat, Spring
60
—
20
55
20
0
0
0
0
0
15
5
15
65
20
10
—


Wheat, Winter
25
—
30
35
20
0
0
5
0
0
20
5
5
60
10
0
—


Windgrass
100
95
60
100
45
0
0
75
25
70
100
100
0
85
65
100
70












Preemergence










62 g ai/ha
31 g ai/ha



Compounds
Compounds

























245
274
284
3
7
18
25
52
58
59
138
141
145
166
178
245
274





Barley, Spring
15
10
15
0
0
5
0
5
10
5
10
20
0
0
—
5
0


Barley, Winter
25
10
0
0
—
10
0
0
10
0
0
35
5
0
—
35
0


Blackgrass
10
70
10
0
0
5
15
5
20
25
0
65
15
55
10
0
30


Bluegrass
0
30
15
0
0
30
0
0
10
5
0
35
20
20
10
0
5


Bromegrass, Downy
35
5
0
0
0
0
0
0
10
0
0
45
30
5
0
0
5


Buckwheat, Wild
25
100
20
0
0
70
10
10
100
60
35
100
25
95
55
0
100


Canarygrass
15
60
25
0
0
25
20
0
20
5
10
75
45
50
60
0
20


Chamomile
55
35
100
0
0
5
5
15
30
10
—
100
85
25
70
30
—


Chickweed
100
100
15
—
0
—
75
100
100
100
100
100
100
95
50
85
85


Deadnettle
0
100
45
30
0
5
5
70
100
100
5
100
55
75
60
0
100


Field Poppy
100
100
100
—
0
70
70
95
95
95
100
100
100
100
70
100
100


Field Violet
100
100
100
80
0
70
25
75
100
65
25
100
90
100
—
95
100


Foxtail, Green
0
100
5
—
0
15
15
20
100
35
0
100
5
65
0
0
75


Galium
5
100
20
0
0
15
15
10
65
0
40
100
15
80
30
0
60


Kochia
75
65
20
30
0
90
15
95
95
90
20
100
95
65
35
0
70


Lambsquarters
100
100
100
0
0
80
25
80
100
95
10
100
100
95
70
100
90


Mustard, Wild
85
95
15
80
20
85
0
20
90
15
65
100
100
95
35
80
25


Oat, Wild
20
15
0
0
0
0
0
0
15
0
0
65
15
30
0
5
0


Oilseed Rape
30
65
0
75
10
30
10
0
100
65
30
100
70
50
75
0
30


Pigweed
100
100
100
0
30
100
95
100
100
100
25
100
100
100
100
100
100


Radish, Wild
0
40
0
20
—
100
20
30
100
95
85
98
75
80
90
0
5


Russian Thistle
30
—
10
0
0
10
—
—
—
—
—
50
15
—
—
10
—


Ryegrass, Italian
20
50
0
0
0
10
0
0
10
0
0
55
15
40
0
15
0


Speedwell
100
100
100
100
50
—
—
100
100
15
100
100
100
100
100
100
100


Wheat, Spring
20
10
10
0
0
0
0
0
0
0
10
30
15
0
—
10
0


Wheat, Winter
20
5
15
0
0
0
0
0
0
0
5
20
0
0
—
15
0


Windgrass
35
100
35
0
0
20
5
50
100
70
0
70
35
75
75
15
90












Preemergence












31 g ai/ha
16 g ai/ha




Compound
Compounds






















284
3
7
18
25
138
141
145
166
178
245
274







Barley, Spring
10
0
0
0
0
10
15
5
0
—
0
0



Barley, Winter
0
0
—
0
0
0
15
0
0
—
0
0



Blackgrass
0
0
0
0
20
0
40
0
10
5
0
10



Bluegrass
0
0
0
10
0
0
15
0
5
0
0
0



Bromegrass, Downy
0
0
0
0
0
0
30
15
5
0
0
0



Buckwheat, Wild
10
0
0
10
10
60
100
0
60
15
25
10



Canarygrass
30
0
0
10
20
10
35
40
30
10
0
20



Chamomile
100
—
0
5
0
—
90
30
5
0
25
5



Chickweed
10
0
0
—
50
100
100
75
85
0
55
60



Deadnettle
35
30
0
10
5
5
90
35
70
50
0
55



Field Poppy
100
40
0
—
0
100
98
90
100
20
100
75



Field Violet
45
40
0
65
25
70
100
60
70
20
55
75



Foxtail, Green
10
10
0
5
0
0
10
5
25
0
0
15



Galium
20
0
0
0
20
25
75
10
65
10
0
0



Kochia
0
0
0
15
15
20
85
5
35
0
0
0



Lambsquarters
30
0
0
70
25
45
100
85
85
20
85
20



Mustard, Wild
15
30
20
80
0
55
90
90
65
25
80
15



Oat, Wild
0
0
0
0
0
0
30
0
0
0
0
0



Oilseed Rape
0
10
0
40
5
35
100
35
35
65
0
35



Pigweed
75
0
0
30
60
0
98
100
100
75
98
70



Radish, Wild
0
0
—
100
10
90
40
75
55
55
0
5



Russian Thistle
0
0
—
—
—
—
15
0
—
—
5
—



Ryegrass, Italian
0
0
0
10
0
0
35
0
20
0
15
0



Speedwell
0
100
20
50
—
70
100
35
100
100
5
100



Wheat, Spring
10
0
0
0
0
0
25
15
0
—
5
0



Wheat, Winter
15
0
0
0
0
0
15
0
0
—
10
0



Windgrass
20
0
0
5
0
0
35
15
50
75
5
20










Test E

Seeds of plant species selected from corn (Zea mays), soybean (Glycine max), velvetleaf (Abutilon theophrasti), lambsquarters (Chenopodium album), wild poinsettia (Euphorbia heterophylla), palmer pigweed (Amaranthus palmeri), waterhemp (common waterhemp, Amaranthus rudis), surinam grass (Brachiaria decumbens), large (Lg) crabgrass (Digitaria sanguinalis), Brazilian crabgrass (Digitaria horizontalis), fall panicum (Panicum dichotomiflorum), giant foxtail (Setaria faberii), green foxtail (Setaria viridis), goosegrass (Eleusine indica), johnsongrass (Sorghum halepense), ragweed (common ragweed, Ambrosia elatior), barnyardgrass (Echinochloa crus-galli), sandbur (southern sandbur, Cenchrus echinatus), arrowleaf sida (Sida rhombifolia), Italian ryegrass (Lolium multiflorum), dayflower (Virginia (VA) dayflower, Commelina virginica), field bindweed (Convolvulus arvensis), morningglory (Ipomoea coccinea), nightshade (eastern black nightshade, Solanum ptycanthum), kochia (Kochia scoparia), yellow nutsedge (Cyperus esculentus), cocklebur (common cocklebur, Xanthium strumarium), smartweed (ladysthumb smartweed, and hairy beggarticks (Bidens pilosa), were planted into a silt loam soil and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant.
At the same time, plants from these crop and weed species and also horseweed (Canada horseweed, Conyza canadensis), waterhemp_RES1, (ALS & Triazine resistant common waterhemp, Amaranthus rudis), and waterhemp_RES2, (ALS & HPPD resistant common waterhemp, Amaranthus rudis) were planted in pots containing Redi-Earth® planting medium (Scotts Company, 14111 Scottslawn Road, Marysville, Ohio 43041) comprising spaghnum peat moss, vermiculite, wetting agent and starter nutrients were treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm for postemergence treatments (1- to 4-leaf stage). Treated plants and controls were maintained in a greenhouse for 14 to 21 days, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table E, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.









TABLE E









Compounds
















250 g ai/ha
5
10
16
25
58
59
200











Postemergence
















Arrowleaf Sida
85
85
90
95
98
90
98



Barnyardgrass
10
0
15
15
70
30
40



Beggarticks
70
80
60
50
95
95
95



Corn
0
0
15
15
15
15
25



Crabgrass, Brazil
20
5
40
35
75
50
60



Dayflower, VA
75
75
40
75
100
100
70



Field Bindweed
40
50
60
70
80
80
95



Panicum, Fall
0
0
25
40
60
45
50



Pigweed, Palmer
98
95
—
100
100
100
100



Poinsettia, Wild
50
60
80
70
90
80
90



Ryegrass, Italian
0
0
0
5
60
60
0



Sandbur
20
0
0
15
55
20
10



Smartweed
—
—
—
—
100
100
—



Soybean
95
95
95
98
100
98
98



Waterhemp
98
95
90
100
100
100
100



Waterhemp_RES1
—
—
95
—
100
100
100



Waterhemp_RES2
95
90
85
—
100
100
100













Compounds





















125 g ai/ha
5
7
10
16
25
52
58
59
65
72
79
181
191
200










Postemergence





















Arrowleaf Sida
80
95
80
80
90
70
95
85
80
75
98
95
100
90


Barnyardgrass
0
10
0
10
10
30
30
15
0
10
20
25
0
20


Beggarticks
60
60
50
50
50
75
90
70
50
80
80
60
50
90


Corn
0
5
0
10
10
25
10
10
10
10
15
15
15
20


Crabgrass, Brazil
10
30
0
30
20
40
55
25
15
20
30
30
20
50


Dayflower, VA
40
90
50
30
70
60
90
70
20
60
50
60
10
60


Field Bindweed
30
70
40
50
60
65
70
70
40
80
80
50
50
95


Horseweed
—
—
—
—
—
—
—
—
—
—
30
5
—
—


Kochia
—
—
—
—
—
80
—
—
—
—
75
90
—
—


Panicum, Fall
0
0
0
20
40
40
60
30
15
10
30
30
20
50


Pigweed, Palmer
95
85
85
—
75
95
100
100
60
90
90
98
85
98


Poinsettia, Wild
35
60
30
70
60
70
—
65
40
60
60
60
60
90


Ragweed
—
—
—
—
—
60
—
—
—
—
60
50
—
—


Ryegrass, Italian
0
0
0
0
0
10
35
25
0
5
0
20
0
0


Sandbur
10
0
0
0
5
20
20
10
0
0
10
20
10
0


Smartweed
—
100
—
—
—
—
100
100
—
—
—
—
—
—


Soybean
80
98
90
95
80
95
95
95
98
95
95
95
95
95


Waterhemp
95
90
95
90
85
95
100
90
95
98
100
98
95
95


Waterhemp_RES1
—
90
—
75
—
—
95
95
98
95
100
95
95
100


Waterhemp_RES2
90
95
80
70
—
90
95
95
98
90
95
100
100
100













Compounds












125 g ai/ha
223
274











Postemergence











Arrowleaf Sida
90
85



Barnyardgrass
0
60



Beggarticks
85
95



Corn
5
15



Crabgrass, Brazil
20
50



Dayflower, VA
65
70



Field Bindweed
50
75



Horseweed
—
—



Kochia
—
—



Panicum, Fall
0
20



Pigweed, Palmer
85
100



Poinsettia, Wild
60
70



Ragweed
—
—



Ryegrass, Italian
0
40



Sandbur
0
0



Smartweed
—
—



Soybean
98
95



Waterhemp
98
98



Waterhemp_RES1
95
100



Waterhemp_RES2
95
100













Compounds





















62 g ai/ha
5
7
10
16
25
52
58
59
65
72
79
181
191
200










Postemergence





















Arrowleaf Sida
70
90
70
75
80
70
90
80
80
50
85
70
70
80


Barnyardgrass
0
10
0
0
10
20
20
10
0
0
10
15
0
0


Beggarticks
60
50
40
50
40
70
80
60
50
70
75
50
50
70


Corn
0
10
0
0
10
20
10
10
10
15
10
15
10
15


Crabgrass, Brazil
10
20
0
10
20
30
40
20
10
10
20
30
10
30


Dayflower, VA
10
70
40
15
60
50
75
50
10
50
50
40
10
40


Field Bindweed
30
50
30
40
50
65
70
65
40
70
80
40
40
90


Horseweed
—
—
—
—
—
—
—
—
—
—
20
5
—
—


Kochia
—
—
—
—
—
55
—
—
—
—
80
50
—
—


Panicum, Fall
0
50
0
10
30
10
40
20
0
10
30
50
10
20


Pigweed, Palmer
85
75
75
—
70
95
100
85
50
75
95
90
75
75


Poinsettia, Wild
30
60
30
60
50
50
—
60
20
55
50
50
50
70


Ragweed
—
—
—
—
—
55
—
—
—
—
50
30
—
—


Ryegrass, Italian
0
0
0
0
0
0
20
15
0
0
0
10
0
0


Sandbur
0
0
0
0
0
25
10
0
0
0
0
10
0
0


Smartweed
—
70
—
—
—
—
85
80
—
—
—
—
—
—


Soybean
70
98
75
80
80
90
95
95
50
95
95
90
50
95


Waterhemp
90
90
85
85
80
75
95
90
75
80
85
95
90
95


Waterhemp_RES1
—
95
—
60
—
—
95
90
90
75
75
90
90
90


Waterhemp_RES2
80
90
75
60
—
95
90
90
95
80
90
98
95
90













Compounds












62 g ai/ha
223
274











Postemergence











Arrowleaf Sida
80
75



Barnyardgrass
0
10



Beggarticks
75
70



Corn
0
10



Crabgrass, Brazil
10
35



Dayflower, VA
55
40



Field Bindweed
50
70



Horseweed
—
—



Kochia
—
—



Panicum, Fall
0
50



Pigweed, Palmer
60
95



Poinsettia, Wild
50
70



Ragweed
—
—



Ryegrass, Italian
0
10



Sandbur
0
15



Smartweed
—
—



Soybean
98
95



Waterhemp
85
95



Waterhemp_RES1
70
90



Waterhemp_RES2
80
95













Compounds





















31 g ai/ha
5
7
10
16
25
52
58
59
65
79
181
191
200
223










Postemergence





















Arrowleaf Sida
60
80
50
70
70
60
80
70
60
75
75
70
80
70


Barnyardgrass
0
0
0
0
10
10
5
0
0
0
20
0
0
0


Beggarticks
40
40
30
30
30
60
65
60
40
50
40
40
60
60


Corn
0
0
0
0
10
10
10
5
10
0
5
10
10
0


Crabgrass, Brazil
5
10
0
0
10
30
20
15
10
10
20
10
15
10


Dayflower, VA
10
50
10
10
60
40
60
35
10
30
30
5
25
25


Field Bindweed
20
30
30
30
50
50
60
60
20
70
40
50
70
35


Horseweed
—
—
—
—
—
—
—
—
—
0
0
—
—
—


Kochia
—
—
—
—
—
50
—
—
—
70
60
—
—
—


Panicum, Fall
—
15
0
0
30
10
30
20
5
35
20
5
10
0


Pigweed, Palmer
75
50
70
—
50
70
95
80
50
50
70
75
70
50


Poinsettia, Wild
20
30
20
60
50
40
—
50
20
40
50
50
80
40


Ragweed
—
—
—
—
—
50
—
—
—
40
25
—
—
—


Ryegrass, Italian
0
0
0
0
0
0
10
0
0
—
5
0
0
0


Sandbur
0
0
0
0
0
10
10
0
0
0
15
0
0
0


Smartweed
—
40
—
—
—
—
65
—
—
—
—
—
—
—


Soybean
30
90
50
30
80
75
95
65
20
70
80
60
95
95


Waterhemp
80
90
80
60
80
70
85
65
70
90
95
90
90
70


Waterhemp_RES1
—
80
—
50
—
—
80
80
85
60
95
80
80
80


Waterhemp_RES2
70
80
60
50
—
90
90
85
90
80
95
95
90
80












Compound










31 g ai/ha
274











Postemergence










Arrowleaf Sida
60



Barnyardgrass
20



Beggarticks
60



Corn
10



Crabgrass, Brazil
25



Dayflower, VA
20



Field Bindweed
50



Horseweed
—



Kochia
—



Panicum, Fall
20



Pigweed, Palmer
85



Poinsettia, Wild
70



Ragweed
—



Ryegrass, Italian
10



Sandbur
10



Smartweed
—



Soybean
75



Waterhemp
90



Waterhemp_RES1
80



Waterhemp_RES2
85













Compounds





















16 g ai/ha
5
7
10
16
25
52
58
59
65
79
181
191
200
223










Postemergence





















Arrowleaf Sida
60
75
40
50
60
50
70
65
50
65
60
60
60
60


Barnyardgrass
0
0
0
0
0
5
0
0
0
0
10
0
0
0


Beggarticks
30
35
10
30
20
30
60
50
35
40
40
20
50
50


Corn
0
0
0
0
0
10
5
5
0
0
5
0
10
0


Crabgrass, Brazil
0
0
0
0
10
15
10
15
0
0
20
10
10
0


Dayflower, VA
0
40
5
0
50
30
50
20
5
10
20
0
15
0


Field Bindweed
10
20
15
10
40
50
50
50
10
60
25
40
70
20


Horseweed
—
—
—
—
—
—
—
—
—
0
0
—
—
—


Kochia
—
—
—
—
—
40
—
—
—
50
35
—
—
—


Panicum, Fall
0
0
0
0
10
5
20
10
0
20
20
0
10
0


Pigweed, Palmer
60
60
60
—
50
60
90
75
20
50
80
40
40
25


Poinsettia, Wild
10
30
5
50
20
45
—
50
20
40
40
40
50
30


Ragweed
—
—
—
—
—
40
—
—
—
30
20
—
—
—


Ryegrass, Italian
0
0
0
0
0
0
10
0
0
0
5
0
0
0


Sandbur
0
0
0
0
0
15
0
0
0
0
5
0
0
0


Smartweed
—
30
—
—
—
—
50
55
—
—
—
—
—
—


Soybean
20
80
30
15
75
70
75
60
20
60
50
30
95
60


Waterhemp
70
80
—
60
80
65
75
—
50
70
65
70
80
50


Waterhemp_RES1
—
70
—
50
—
—
80
70
70
40
90
70
70
60


Waterhemp_RES2
60
75
50
25
—
80
80
75
80
75
85
90
90
75












Compound










16 g ai/ha
274











Postemergence










Arrowleaf Sida
75



Barnyardgrass
10



Beggarticks
50



Corn
15



Crabgrass, Brazil
20



Dayflower, VA
10



Field Bindweed
50



Horseweed
—



Kochia
—



Panicum, Fall
15



Pigweed, Palmer
65



Poinsettia, Wild
65



Ragweed
—



Ryegrass, Italian
5



Sandbur
0



Smartweed
—



Soybean
35



Waterhemp
95



Waterhemp_RES1
75



Waterhemp_RES2
80













Compounds














8 g ai/ha
7
65
191
223
274











Postemergence














Arrowleaf Sida
65
55
50
50
55



Barnyardgrass
0
0
0
0
5



Beggarticks
25
20
10
40
30



Corn
0
0
0
0
10



Crabgrass, Brazil
0
0
10
0
10



Dayflower, VA
10
5
0
0
5



Field Bindweed
15
0
20
20
60



Panicum, Fall
0
0
0
0
10



Pigweed, Palmer
40
10
20
15
70



Poinsettia, Wild
0
15
20
30
50



Ryegrass, Italian
0
0
0
0
0



Sandbur
0
0
0
0
0



Smartweed
15
—
—
—
—



Soybean
60
15
20
30
20



Waterhemp
70
60
60
60
70



Waterhemp_RES1
65
65
50
30
60














Compounds


















250 g ai/ha
16
18
52
58
59
72
73
89
180
200










Preemergence

















Arrowleaf Sida
98
95
100
100
100
100
100
100
85
100


Barnyardgrass
40
20
98
98
95
90
75
98
100
95


Beggarticks
0
0
65
100
25
30
75
95
90
95


Cocklebur
—
—
25
50
0
15
25
—
—
95


Corn
25
0
40
70
50
0
5
70
65
75


Crabgrass, Brazil
100
100
100
100
100
100
100
100
100
100


Crabgrass, Large
100
100
100
100
100
100
100
100
100
100


Dayflower, VA
98
98
98
98
98
95
95
98
90
85


Field Bindweed
60
40
95
100
100
95
85
90
90
95


Foxtail, Giant
100
98
100
100
100
100
100
100
100
70


Foxtail, Green
100
100
100
100
100
100
95
85
100
100


Goosegrass
95
98
100
100
98
100
100
50
100
90


Johnsongrass
40
—
98
100
100
98
85
100
80
75


Kochia
100
100
100
100
100
100
100
100
100
100


Lambsquarters
98
98
100
98
100
100
100
100
100
100


Morningglory
95
35
98
100
100
35
60
100
100
98


Nightshade
100
100
100
100
100
100
100
100
100
100


Nutsedge, Yellow
35
10
50
80
50
50
30
35
75
70


Panicum, Fall
100
100
100
100
100
100
100
100
100
100


Pigweed, Palmer
—
—
100
100
100
100
100
100
90
100


Poinsettia, Wild
100
50
100
100
100
70
85
85
98
95


Ragweed
65
0
70
85
50
95
80
90
100
95


Ryegrass, Italian
75
35
90
98
95
75
65
0
70
80


Sandbur
95
75
80
95
95
50
35
20
90
70


Smartweed
—
—
—
—
—
98
98
—
—
—


Soybean
95
90
90
95
95
90
80
80
98
90


Surinam Grass
50
20
10
90
65
30
35
75
100
100


Velvetleaf
100
100
90
100
100
100
95
100
100
100


Waterhemp
100
100
100
100
100
100
100
100
100
100












Compounds





















125 g ai/ha
7
16
18
25
52
58
59
72
73
86
88
89
90
111










Preemergence





















Arrowleaf Sida
80
95
85
65
80
100
100
100
100
100
35
100
90
98


Barnyardgrass
0
10
5
0
75
95
75
35
20
30
0
70
40
35


Beggarticks
0
0
0
50
40
15
0
5
50
70
0
80
30
80


Cocklebur
0
—
—
—
—
0
—
0
—
—
—
—
—
—


Corn
0
20
0
0
0
65
30
0
0
5
35
30
0
15


Crabgrass, Brazil
100
100
100
100
100
100
100
100
100
95
60
100
80
100


Crabgrass, Large
98
80
100
95
100
100
100
100
100
98
95
100
98
100


Dayflower, VA
65
70
95
40
70
98
85
65
65
65
60
80
0
20


Field Bindweed
0
30
40
65
80
98
60
60
75
90
50
95
65
80


Foxtail, Giant
90
100
95
80
100
100
100
98
95
100
25
65
50
100


Foxtail, Green
75
90
100
80
80
100
100
100
80
75
35
65
50
90


Goosegrass
75
75
90
75
98
100
98
98
98
50
5
5
50
65


Johnsongrass
50
25
80
60
70
95
75
95
35
65
15
50
15
70


Kochia
95
100
100
85
100
100
100
100
98
100
50
100
100
95


Lambsquarters
100
98
98
98
98
98
100
100
100
100
100
95
100
100


Morningglory
0
25
0
50
95
100
75
15
30
75
15
75
35
75


Nightshade
98
100
100
98
98
100
100
98
98
98
0
100
80
95


Nutsedge, Yellow
0
35
0
0
25
60
30
25
40
20
0
20
0
15


Panicum, Fall
—
100
100
—
100
100
100
100
98
100
10
100
80
100


Pigweed, Palmer
100
—
—
100
100
100
100
100
100
100
75
40
65
100


Poinsettia, Wild
0
50
0
40
50
100
20
70
65
65
0
70
75
85


Ragweed
0
30
0
5
5
50
5
50
60
20
65
80
75
90


Ryegrass, Italian
20
40
20
10
60
98
75
35
35
5
0
0
0
20


Sandbur
35
70
5
15
35
90
50
35
30
10
10
10
0
0


Smartweed
—
—
—
—
—
—
—
90
98
—
—
—
—
—


Soybean
50
90
90
30
60
75
50
70
70
60
20
60
35
70


Surinam Grass
35
30
0
35
10
65
20
10
20
0
10
10
0
25


Velvetleaf
100
100
100
80
85
100
100
65
70
80
65
90
85
75


Waterhemp
100
100
100
100
100
100
100
100
100
100
100
80
100
100












Compounds


















125 g ai/ha
138
145
151
164
167
170
179
180
200
250
292










Preemergence


















Arrowleaf Sida
100
100
100
100
100
100
100
70
100
100
80


Barnyardgrass
60
0
75
65
75
75
20
100
60
25
40


Beggarticks
0
35
100
20
0
0
0
40
75
20
35


Cocklebur
—
—
—
—
90
—
—
—
75
—
—


Corn
35
10
0
0
25
30
0
40
30
20
0


Crabgrass, Brazil
98
85
75
100
100
100
100
100
100
98
100


Crabgrass, Large
100
90
100
100
100
100
98
100
80
100
100


Dayflower, VA
40
80
85
90
100
95
60
85
65
70
85


Field Bindweed
50
0
35
50
10
30
30
65
70
0
65


Foxtail, Giant
75
70
95
95
100
100
100
100
25
98
95


Foxtail, Green
98
65
75
100
90
100
100
100
75
90
75


Goosegrass
70
25
85
75
98
98
70
98
80
65
70


Johnsongrass
40
75
70
70
70
70
25
75
30
50
35


Kochia
100
90
100
100
90
98
75
100
100
98
98


Lambsquarters
100
100
100
100
100
100
100
100
98
100
100


Morningglory
40
35
0
98
65
95
30
60
90
20
50


Nightshade
90
80
90
95
100
98
95
98
100
98
80


Nutsedge, Yellow
40
20
0
20
0
40
30
60
40
40
35


Panicum, Fall
100
98
98
98
100
100
98
100
100
100
100


Pigweed, Palmer
70
95
100
80
100
100
100
75
100
100
100


Poinsettia, Wild
25
35
100
30
25
40
35
65
90
20
60


Ragweed
0
60
100
60
35
35
0
100
80
0
35


Ryegrass, Italian
20
0
65
60
40
70
15
30
60
0
35


Sandbur
15
20
35
10
65
35
15
75
40
25
35


Smartweed
—
—
—
—
—
—
—
—
—
—
—


Soybean
35
65
75
70
50
60
40
90
65
65
50


Surinam Grass
50
0
100
20
0
25
0
75
100
0
20


Velvetleaf
100
100
100
100
100
100
100
100
100
100
90


Waterhemp
100
100
100
90
100
80
98
100
100
100
100












Compounds





















62 g ai/ha
7
16
18
25
52
58
59
72
73
86
88
89
90
111










Preemergence





















Arrowleaf Sida
50
70
70
35
60
100
75
40
80
60
10
75
75
70


Barnyardgrass
0
0
0
0
30
90
50
15
0
0
0
20
0
0


Beggarticks
0
0
0
50
0
0
0
5
20
35
0
60
10
60


Cocklebur
—
—
0
—
0
—
0
—
—
—
—
—
—
—


Corn
0
0
0
0
0
40
0
0
0
0
35
0
0
0


Crabgrass, Brazil
100
100
98
100
100
100
100
100
100
75
60
90
50
75


Crabgrass, Large
75
65
40
50
98
100
100
100
100
95
65
85
75
90


Dayflower, VA
20
35
35
25
5
70
25
35
25
30
0
60
—
20


Field Bindweed
0
0
30
60
25
70
60
10
50
20
0
75
70
60


Foxtail, Giant
40
100
65
50
70
100
85
95
50
30
0
20
15
70


Foxtail, Green
35
70
65
60
75
100
100
95
70
15
0
35
10
70


Goosegrass
40
50
30
25
65
95
65
80
70
50
5
0
5
40


Johnsongrass
40
0
0
25
30
95
60
40
20
65
15
10
0
15


Kochia
50
65
80
35
65
100
100
98
98
100
35
75
100
95


Lambsquarters
98
98
98
98
98
98
100
100
98
100
100
5
50
98


Morningglory
0
0
0
25
35
100
65
15
10
30
10
65
20
75


Nightshade
98
100
98
98
75
100
90
100
90
0
—
80
80
80


Nutsedge, Yellow
0
0
0
0
0
25
0
0
50
0
0
0
0
0


Panicum, Fall
—
100
70
—
100
100
98
98
98
90
0
65
0
80


Pigweed, Palmer
100
—
—
100
100
100
100
100
100
100
0
0
0
100


Poinsettia, Wild
—
50
0
0
25
90
10
15
35
20
0
40
70
70


Ragweed
0
0
0
0
0
5
0
5
30
5
0
80
50
70


Ryegrass, Italian
0
15
0
10
0
75
50
20
35
0
0
0
0
0


Sandbur
0
20
0
5
10
75
30
30
20
10
0
10
0
0


Smartweed
—
—
—
—
—
—
—
0
20
—
—
—
—
—


Soybean
40
60
60
0
0
60
—
25
25
35
20
30
30
40


Surinam Grass
10
0
0
40
0
25
5
20
5
0
0
0
0
0


Velvetleaf
98
85
100
80
75
90
75
40
60
50
20
65
60
60


Waterhemp
100
100
100
100
100
100
100
100
100
100
35
70
20
80












Compounds



















62 g ai/ha
138
145
151
164
167
170
179
180
194
200
250
292










Preemergence



















Arrowleaf Sida
40
100
100
100
100
90
100
30
100
70
60
5


Barnyardgrass
15
0
10
0
25
35
10
98
0
10
0
0


Beggarticks
0
30
95
20
0
0
0
20
0
35
0
15


Cocklebur
—
—
—
—
100
—
—
—
—
—
—
—


Corn
15
0
0
0
15
10
0
15
0
30
0
0


Crabgrass, Brazil
90
50
70
75
75
100
65
100
98
100
5
100


Crabgrass, Large
98
35
60
75
100
98
75
98
95
65
0
90


Dayflower, VA
30
0
65
65
65
80
0
35
40
65
50
35


Field Bindweed
40
0
20
30
0
20
0
25
40
40
0
30


Foxtail, Giant
30
20
60
60
100
100
65
100
75
0
15
80


Foxtail, Green
20
35
70
60
70
90
25
100
80
30
0
25


Goosegrass
50
0
70
20
75
75
35
90
75
60
0
50


Johnsongrass
35
0
35
10
30
25
20
50
50
25
0
20


Kochia
90
0
90
75
65
90
25
20
35
95
0
70


Lambsquarters
100
100
100
98
100
100
95
100
100
80
0
25


Morningglory
0
20
0
35
40
35
10
15
0
50
0
15


Nightshade
98
65
75
80
100
98
80
98
95
85
35
70


Nutsedge, Yellow
15
0
0
0
0
30
30
30
20
0
0
15


Panicum, Fall
100
90
100
30
100
98
75
100
100
95
0
90


Pigweed, Palmer
75
50
100
75
98
100
100
0
100
100
0
100


Poinsettia, Wild
35
20
100
5
20
25
30
15
0
50
0
35


Ragweed
0
0
95
25
35
5
0
90
20
80
0
0


Ryegrass, Italian
0
0
10
30
10
35
15
0
0
20
0
0


Sandbur
10
0
0
0
20
30
15
20
20
5
0
0


Smartweed
—
—
—
—
—
—
—
—
90
—
—
—


Soybean
—
65
—
15
20
30
25
70
20
35
15
40


Surinam Grass
20
0
35
20
0
15
0
25
0
70
0
10


Velvetleaf
90
95
100
100
65
65
100
80
25
80
75
35


Waterhemp
90
100
98
90
98
90
90
98
100
100
0
80












Compounds





















31 g ai/ha
7
16
18
25
52
58
59
72
73
86
88
89
90
111










Preemergence





















Arrowleaf Sida
25
35
5
35
40
100
50
40
40
5
40
50
50
50


Barnyardgrass
0
0
0
0
0
40
20
0
0
0
0
0
0
0


Beggarticks
0
0
0
35
0
0
0
0
5
0
0
35
5
30


Cocklebur
—
—
—
—
0
0
0
—
0
—
—
—
—
—


Corn
0
0
0
0
0
5
0
0
0
0
0
0
0
0


Crabgrass, Brazil
80
—
95
100
90
100
100
98
95
0
0
20
20
30


Crabgrass, Large
70
0
0
20
35
100
95
80
30
0
35
35
40
35


Dayflower, VA
0
0
0
25
0
20
5
0
0
0
0
0
0
0


Field Bindweed
0
0
0
60
0
20
5
5
15
10
0
35
50
15


Foxtail, Giant
20
20
15
35
70
100
10
35
20
15
0
0
0
0


Foxtail, Green
30
20
0
20
20
95
60
30
20
0
0
0
0
10


Goosegrass
35
35
0
25
50
70
25
60
20
0
0
0
0
5


Johnsongrass
0
0
0
—
0
35
0
0
20
0
0
0
0
0


Kochia
0
0
0
25
25
100
80
75
75
90
0
60
50
10


Lambsquarters
75
80
90
50
75
98
98
90
65
65
50
20
75
80


Morningglory
0
0
0
0
5
50
15
0
0
10
0
30
0
35


Nightshade
98
98
95
98
0
98
50
65
80
0
0
—
10
50


Nutsedge, Yellow
0
0
0
0
0
5
0
0
0
0
0
0
0
0


Panicum, Fall
—
80
50
—
0
98
75
65
40
35
0
0
0
5


Pigweed, Palmer
85
—
—
100
100
100
100
100
75
0
0
0
0
20


Poinsettia, Wild
0
0
0
0
0
15
0
5
30
10
0
20
35
30


Ragweed
0
0
0
0
0
0
0
0
5
0
0
65
50
50


Ryegrass, Italian
0
0
0
0
0
35
0
15
20
0
0
0
0
0


Sandbur
0
20
0
0
0
20
15
40
20
10
0
0
0
0


Smartweed
—
—
—
—
—
—
—
0
0
—
—
—
—
—


Soybean
0
60
0
0
0
0
0
10
25
0
0
—
15
20


Surinam Grass
0
0
0
65
0
0
0
20
0
0
0
0
0
0


Velvetleaf
65
50
95
60
0
70
25
0
20
0
0
20
20
10


Waterhemp
100
100
100
100
100
100
100
98
100
70
35
0
0
65












Compounds


















31 g ai/ha
138
145
151
164
167
170
180
194
200
250
292










Preemergence


















Arrowleaf Sida
0
100
80
100
65
10
15
35
20
20
5


Barnyardgrass
0
0
20
0
20
0
20
0
0
0
0


Beggarticks
0
0
65
0
0
0
10
0
10
0
15


Cocklebur
—
—
—
—
0
—
—
—
0
—
—


Corn
0
0
0
0
0
20
0
0
5
0
0


Crabgrass, Brazil
40
0
35
20
20
100
90
65
85
0
40


Crabgrass, Large
70
0
5
35
65
70
90
85
35
0
20


Dayflower, VA
5
0
10
20
5
30
0
0
35
0
20


Field Bindweed
20
0
0
0
0
0
10
0
10
0
5


Foxtail, Giant
0
0
25
20
0
25
75
25
0
0
5


Foxtail, Green
0
0
20
25
35
40
65
35
5
0
10


Goosegrass
30
0
0
5
60
40
70
40
5
0
20


Johnsongrass
0
0
0
0
10
15
0
0
15
0
15


Kochia
75
0
80
0
40
30
0
5
60
0
0


Lambsquarters
50
100
100
75
98
98
98
80
65
0
0


Morningglory
0
0
0
65
25
10
0
0
20
0
0


Nightshade
0
0
30
50
98
50
75
95
10
0
5


Nutsedge, Yellow
10
0
0
0
0
20
0
0
0
0
0


Panicum, Fall
25
0
60
0
65
20
95
80
75
0
0


Pigweed, Palmer
70
0
100
0
0
95
0
98
40
0
35


Poinsettia, Wild
25
0
60
0
0
20
10
10
50
0
5


Ragweed
0
0
90
0
15
0
70
0
0
0
0


Ryegrass, Italian
0
0
10
0
0
20
0
0
0
0
0


Sandbur
0
0
0
0
0
0
0
20
0
0
20


Smartweed
—
—
—
—
—
—
—
0
—
—
—


Soybean
0
15
30
0
0
0
35
0
25
0
0


Surinam Grass
0
0
0
0
0
0
10
0
5
0
0


Velvetleaf
70
90
95
50
20
60
35
5
35
75
30


Waterhemp
100
98
75
65
98
80
98
98
100
0
20












Compounds





















16 g ai/ha
7
16
18
25
52
58
59
72
73
86
88
90
111
138










Preemergence





















Arrowleaf Sida
0
5
0
20
35
80
50
20
5
0
30
20
40
0


Barnyardgrass
0
0
0
0
0
20
0
0
0
0
0
0
0
0


Beggarticks
0
0
0
20
0
0
0
0
5
0
0
0
20
0


Cocklebur
—
0
—
—
0
—
—
0
0
—
—
—
—
—


Corn
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Crabgrass, Brazil
0
—
0
0
0
100
80
90
25
0
0
0
0
0


Crabgrass, Large
0
0
0
15
0
75
5
50
0
0
0
30
15
0


Dayflower, VA
0
0
0
35
0
5
0
0
0
0
0
0
0
0


Field Bindweed
0
0
0
60
0
0
0
0
0
0
0
35
15
0


Foxtail, Giant
20
15
0
10
0
75
5
35
0
0
0
0
0
0


Foxtail, Green
0
0
0
20
0
65
0
30
0
0
0
0
0
0


Goosegrass
0
0
0
20
5
10
15
0
0
0
0
0
0
10


Johnsongrass
0
0
0
0
0
—
0
0
0
0
0
0
0
0


Kochia
0
0
0
0
—
35
20
10
5
0
0
0
0
60


Lambsquarters
0
50
80
0
0
98
98
0
10
0
75
5
50
0


Morningglory
0
0
0
0
0
—
0
0
0
0
0
0
20
0


Nightshade
65
0
0
0
0
90
0
0
65
0
—
10
65
0


Nutsedge, Yellow
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Panicum, Fall
—
0
0
—
0
95
50
0
0
0
0
0
0
0


Pigweed, Palmer
95
—
—
70
25
100
35
95
0
—
0
0
10
0


Poinsettia, Wild
0
0
0
0
0
5
0
15
0
0
0
10
15
0


Ragweed
0
0
0
0
0
0
0
0
0
0
0
0
25
0


Ryegrass, Italian
0
0
0
0
0
30
0
0
0
0
0
0
0
0


Sandbur
0
0
0
0
0
0
0
25
10
0
0
0
0
0


Smartweed
—
—
—
—
—
—
—
0
0
—
—
—
—
—


Soybean
0
0
0
0
0
0
0
0
15
0
35
—
0
0


Surinam Grass
0
0
0
50
0
0
0
20
0
0
0
0
0
0


Velvetleaf
50
0
25
35
0
40
0
0
0
0
0
0
5
40


Waterhemp
100
100
100
100
80
98
100
95
65
0
20
0
0
0









Compounds


















16 g ai/ha
145
151
164
167
170
179
200
250
292











Preemergence


















Arrowleaf Sida
35
60
40
65
0
20
20
0
0



Barnyardgrass
0
0
0
20
0
0
0
0
0



Beggarticks
0
65
0
0
0
0
0
0
0



Cocklebur
—
—
—
0
—
—
0
—
—



Corn
0
0
0
0
0
0
0
0
0



Crabgrass, Brazil
0
0
0
0
40
0
30
0
10



Crabgrass, Large
0
0
35
0
0
0
5
0
0



Dayflower, VA
0
0
0
0
30
0
0
0
20



Field Bindweed
0
0
0
0
0
0
5
0
0



Foxtail, Giant
0
0
0
0
0
0
0
0
0



Foxtail, Green
0
20
0
10
0
0
0
0
0



Goosegrass
0
0
0
0
0
30
10
0
0



Johnsongrass
0
0
0
10
15
0
0
0
15



Kochia
0
5
0
0
0
0
40
0
0



Lambsquarters
0
98
65
40
0
0
0
0
0



Morningglory
0
0
20
25
0
0
10
0
0



Nightshade
0
0
60
0
0
0
0
0
0



Nutsedge, Yellow
0
0
0
0
0
0
0
0
0



Panicum, Fall
0
80
0
0
0
30
20
0
0



Pigweed, Palmer
0
25
0
0
50
0
0
0
0



Poinsettia, Wild
0
20
0
0
0
0
20
0
15



Ragweed
0
65
0
0
0
0
0
0
0



Ryegrass, Italian
0
0
0
0
0
0
0
0
0



Sandbur
0
0
0
0
0
0
0
0
0



Smartweed
—
—
—
—
—
—
—
—
—



Soybean
0
25
0
0
0
0
0
0
0



Surinam Grass
0
0
0
0
0
0
0
0
0



Velvetleaf
35
50
20
20
20
25
0
20
20



Waterhemp
0
75
0
20
35
70
30
0
0













Compounds














8 g ai/ha
7
25
170
179
292











Preemergence














Arrowleaf Sida
0
0
0
0
0



Barnyardgrass
0
0
0
0
0



Beggarticks
0
0
0
0
0



Corn
0
0
0
0
0



Crabgrass, Brazil
0
—
30
0
0



Crabgrass, Large
0
0
0
0
0



Dayflower, VA
0
30
0
0
20



Field Bindweed
0
30
0
0
0



Foxtail, Giant
15
15
0
0
0



Foxtail, Green
0
20
0
0
0



Goosegrass
0
25
0
0
0



Johnsongrass
0
0
15
0
0



Kochia
0
0
0
0
0



Lambsquarters
0
0
0
0
0



Morningglory
0
0
0
0
0



Nightshade
0
0
0
0
0



Nutsedge, Yellow
0
0
0
0
0



Panicum, Fall
—
—
0
0
0



Pigweed, Palmer
0
35
0
0
0



Poinsettia, Wild
0
0
0
0
0



Ragweed
0
0
0
0
0



Ryegrass, Italian
0
0
0
0
0



Sandbur
0
0
0
0
0



Soybean
0
0
0
0
0



Surinam Grass
0
35
0
0
0



Velvetleaf
20
—
0
20
0



Waterhemp
95
95
0
0
0










Test F

Seeds of plant species selected from bermudagrass (Cynodon dactylon), surinam grass (Brachiaria decumbens), large (Lg) crabgrass (Digitaria sanguinalis), crabgrass, naked (naked crabgrass, Digitaria nuda), foxtail, green (green foxtail, Setaria viridis), johnsongrass (Sorghum halepense), kochia (Kochia scoparia), morningglory (pitted morningglory, Ipomoea lacunosa), nutsedge, purple (purple nutsedge, Cyperus rotundus), ragweed (common ragweed, Ambrosia elatior), mustard, black (black mustard, Brassica nigra), guineagrass (Panicum maximum), dallisgrass (Paspalum dilatatum), barnyardgrass (Echinochloa crus-galli), sandbur (southern sandbur, Cenchrus echinatus), sowthistle (common sowthistle, Sonchus oleraceous), Italian ryegrass (Lolium multiflorum), signalgrass (broadleaf signalgrass, Brachiaria platyphylla), dayflower (Virginia (VA) dayflower, Commelina virginica), bluegrass (annual bluegrass, Poa annua), quackgrass (Elytrigia repens), mallow (common mallow, Malva sylvestris), buckwheat, wild (wild buckwheat, Polygonum convolvulus), leafy spurge (Euphorbia esula), chickweed (common chickweed, Stellaria media), wild poinsettia (Euphorbia heterophylla), and pigweed (Amaranthus retroflexus) were planted into a blend of loam soil and sand and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant.
Treated plants and controls were maintained in a greenhouse for 21 days, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table F, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.










TABLE F









Compounds















58
79
97
274











250 g ai/ha


Preemergence













Barnyardgrass
100
100
100
100



Bermudagrass
100
100
100
100



Bluegrass
100
100
100
100



Buckwheat, Wild
100
100
100
100



Chickweed
100
100
100
100



Crabgrass, Large
100
100
100
100



Crabgrass, Naked
100
100
100
100



Dallisgrass
100
100
100
100



Dayflower, VA
100
100
100
100



Foxtail, Green
100
100
100
100



Guineagrass
100
100
100
100



Johnsongrass
100
100
100
100



Kochia
100
100
100
100



Leafy Spurge
100
100
100
100



Mallow
100
100
100
100



Morningglory
100
100
100
100



Mustard, Black
100
100
100
100



Nutsedge, Purple
80
85
90
98



Pigweed
100
100
100
100



Poinsettia, Wild
100
100
98
100



Quackgrass
100
100
100
98



Ragweed
95
100
100
100



Ryegrass, Italian
100
100
100
100



Sandbur
100
100
100
100



Signalgrass
100
100
100
100



Sowthistle
100
100
100
100



Surinam Grass
100
100
100
100







125 g ai/ha


Preemergence













Barnyardgrass
100
100
100
100



Bermudagrass
100
100
100
100



Bluegrass
98
100
98
85



Buckwheat, Wild
100
100
100
100



Chickweed
100
100
100
100



Crabgrass, Large
100
100
100
100



Crabgrass, Naked
100
100
100
100



Dallisgrass
100
100
100
100



Dayflower, VA
100
100
98
100



Foxtail, Green
100
100
100
100



Guineagrass
100
100
100
100



Johnsongrass
100
100
100
100



Kochia
100
100
100
100



Leafy Spurge
100
100
100
100



Mallow
100
100
100
100



Morningglory
100
100
98
98



Mustard, Black
100
100
100
100



Nutsedge, Purple
70
70
75
85



Pigweed
100
100
100
100



Poinsettia, Wild
100
100
98
95



Quackgrass
100
98
95
85



Ragweed
75
100
95
70



Ryegrass, Italian
100
100
85
75



Sandbur
100
98
100
95



Signalgrass
100
100
100
100



Sowthistle
100
100
100
100



Surinam Grass
100
100
90
100







62 g ai/ha


Preemergence













Barnyardgrass
100
100
95
100



Bermudagrass
100
100
100
100



Bluegrass
98
98
75
50



Buckwheat, Wild
100
100
100
100



Chickweed
100
100
100
100



Crabgrass, Large
100
100
100
100



Crabgrass, Naked
100
100
100
100



Dallisgrass
100
100
100
100



Dayflower, VA
100
100
98
98



Foxtail, Green
100
100
100
100



Guineagrass
100
100
100
100



Johnsongrass
100
100
95
100



Kochia
100
100
100
100



Leafy Spurge
100
100
100
100



Mallow
98
100
98
98



Morningglory
100
100
90
65



Mustard, Black
100
100
100
100



Nutsedge, Purple
40
70
30
65



Pigweed
100
100
100
100



Poinsettia, Wild
100
98
75
70



Quackgrass
98
95
50
70



Ragweed
70
98
85
30



Ryegrass, Italian
98
98
70
70



Sandbur
95
95
25
70



Signalgrass
100
100
85
100



Sowthistle
100
100
100
100



Surinam Grass
98
95
50
70







31 g ai/ha


Preemergence













Barnyardgrass
100
100
90
100



Bermudagrass
100
100
95
100



Bluegrass
80
75
35
20



Buckwheat, Wild
100
100
100
100



Chickweed
100
100
100
98



Crabgrass, Large
100
100
100
100



Crabgrass, Naked
100
100
100
100



Dallisgrass
100
98
98
100



Dayflower, VA
95
98
80
95



Foxtail, Green
100
100
100
100



Guineagrass
100
100
100
100



Johnsongrass
98
100
65
70



Kochia
100
100
100
100



Leafy Spurge
95
98
98
98



Mallow
100
100
75
98



Morningglory
98
100
60
50



Mustard, Black
100
100
100
100



Nutsedge, Purple
60
10
35
50



Pigweed
100
100
100
100



Poinsettia, Wild
65
85
20
10



Quackgrass
70
70
35
40



Ragweed
65
70
75
30



Ryegrass, Italian
95
75
35
40



Sandbur
35
15
10
20



Signalgrass
100
100
90
70



Sowthistle
100
100
100
100



Surinam Grass
60
90
10
35







16 g ai/ha


Preemergence













Barnyardgrass
70
75
0
75



Bermudagrass
95
98
80
85



Bluegrass
50
50
5
0



Buckwheat, Wild
90
98
85
100



Chickweed
100
98
100
98



Crabgrass, Large
100
98
98
100



Crabgrass, Naked
100
100
100
100



Dallisgrass
90
65
75
95



Dayflower, VA
90
95
35
90



Foxtail, Green
75
95
75
100



Guineagrass
100
100
100
100



Johnsongrass
65
65
0
65



Kochia
98
100
100
100



Leafy Spurge
100
95
98
100



Mallow
60
98
30
98



Morningglory
100
98
10
35



Mustard, Black
100
100
90
98



Nutsedge, Purple
0
0
15
35



Pigweed
100
100
100
100



Poinsettia, Wild
25
50
10
5



Quackgrass
50
40
0
40



Ragweed
60
25
10
30



Ryegrass, Italian
35
30
0
35



Sandbur
10
10
0
5



Signalgrass
95
98
25
75



Sowthistle
100
100
100
100



Surinam Grass
25
75
0
10










Test G

Three plastic pots (ca. 16-cm diameter) per rate were partially filled with sterilized Tama silt loam soil comprising a 35:50:15 ratio of sand, silt and clay and 2.6% organic matter. Separate plantings for each of the three pots were as follows. Seeds from the U.S. of monochoria (Monochoria vaginalis), sedge, umbrella (small-flower umbrella sedge, Cyperus difformis), hardstem bulrush (Scirpus juncoides), and redstem (purple redstem, Ammannia coccinea), were planted into one 16-cm pot for each rate. Seeds from the U.S. of rice flatsedge (Cyperus iria), bearded sprangletop (Leptochloa fascicularis), one stand of 9 or 10 water seeded rice seedlings (Oryza sativa cv. ‘Japonica—M202’), and two stands of 3 or 4 transplanted rice seedlings (Oryza sativa cv. ‘Japonica—M202’) were planted into one 16-cm pot for each rate. Seeds from the U.S. of barnyardgrass (Echinochloa crus-galli), and late watergrass (Echinochloa oryzicola) were planted into one 16-cm pot for each rate. Plantings were sequential so that crop and weed species were at the 2.0 to 2.5-leaf stage at time of treatment.
Potted plants were grown in a greenhouse with day/night temperature settings of 30/27° C., and supplemental balanced lighting was provided to maintain a 16-hour photoperiod. Test pots were maintained in the greenhouse until test completion.
At time of treatment, test pots were flooded to 3 cm above the soil surface, treated by application of test compounds directly to the paddy water, and then maintained at that water depth for the duration of the test. Effects of treatments on rice and weeds were visually evaluated by comparison to untreated controls after 21 days. Plant response ratings, summarized in Table G, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.










TABLE G









Compounds











16
18











250 g ai/ha


Flood











Barnyardgrass
100
100



Bulrush, Hardstem
80
85



Flatsedge, Rice
100
100



Monochoria
100
100



Redstem
95
90



Rice, Transplanted
—
20



Rice, Water Seeded
100
100



Sedge, Umbrella
100
100



Sprangletop, Brdd.
100
100



Watergrass, Late
80
70







125 g ai/ha


Flood











Barnyardgrass
100
35



Bulrush, Hardstem
65
0



Flatsedge, Rice
100
100



Monochoria
100
100



Redstem
85
75



Rice, Transplanted
—
15



Rice, Water Seeded
100
90



Sedge, Umbrella
100
35



Sprangletop, Brdd.
100
90



Watergrass, Late
0
0







64 g ai/ha


Flood











Barnyardgrass
40
20



Bulrush, Hardstem
50
0



Flatsedge, Rice
85
75



Monochoria
95
95



Redstem
60
0



Rice, Water Seeded
90
60



Sedge, Umbrella
60
20



Sprangletop, Brdd.
100
80



Watergrass, Late
0
0







32 g ai/ha


Flood











Barnyardgrass
0
0



Bulrush, Hardstem
40
0



Flatsedge, Rice
40
30



Monochoria
95
95



Redstem
0
0



Rice, Transplanted
0
—



Rice, Water Seeded
50
—



Sedge, Umbrella
0
0



Sprangletop, Brdd.
65
70



Watergrass, Late
0
0

## Claims

1. A compound selected from a compound of Formula 1, N-oxides and salts thereof



wherein
each Y1, Y2, Y3 and Y4 is independently selected from the group consisting of N and CR1, provided no more than 3 of Y1, Y2, Y3 and Y4 are N;
Z is selected from the group consisting of O and S;
each R1 is independently selected from the group consisting of hydrogen, halogen, cyano, nitro, SF5, CHO, C(═O)NH2, C(═S)NH2, SO2NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C8 alkylcycloalkyl, C4-C8 cycloalkylalkyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C3-C7 cycloalkylcarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C4-C8 cycloalkylalkoxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkoxyhaloalkyl, C2-C6 alkoxyalkoxy, C2-C4 alkylcarbonyloxy, C2-C6 cyanoalkyl, C2-C6 cyanoalkoxy, C2-C4 alkylthioalkyl, SOnR1A, Si(CH3)3, B(—OC(R1B)2C(R1B)2O—); a phenyl ring optionally substituted with up to 5 substituents independently selected from R1C; and a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from the group consisting of up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R1C on carbon atom ring members and R1D on nitrogen atom ring members;
R2 is selected from the group consisting of halogen, cyano, nitro, C1-C4 alkoxy, C1-C4 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, SOnR2A, C1-C4 haloalkyl and C3-C6 cycloalkyl;
m is selected from the group consisting of 0, 1, 2 and 3;
each R3 is independently selected from the group consisting of halogen, cyano, hydroxy, nitro, amino, CHO, C(═O)NH2, C(═S)NH2, SO2NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C8 alkylcycloalkyl, C4-C8 cycloalkylalkyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C3-C7 cycloalkylcarbonyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C4-C8 cycloalkylalkoxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkoxyhaloalkyl, C2-C6 alkoxyalkoxy, C2-C4 alkylcarbonyloxy, C2-C6 cyanoalkyl, C2-C6 cyanoalkoxy, C2-C4 alkylthioalkyl, Si(CH3)3, C≡CSi(CH3)3, C(═O)N(R3A)(R3B), C(═NOR3C)H, C(═NR3D)H, SOnR3E; a phenyl ring optionally substituted with up to 5 substituents independently selected from R3F; a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from the group consisting of up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R3F on carbon atom ring members and R3G on nitrogen atom ring members; and pyrimidinyloxy;
each n is independently selected from the group consisting of 0, 1 and 2;
each R1A, R2A and R3E is independently selected from the group consisting of C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkylamino and C2-C6 dialkylamino;
each R1B is independently selected from the group consisting of H and C1-C4 alkyl;
each R1C is independently selected from the group consisting of hydroxy, halogen, cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy;
each R1D is independently selected from the group consisting of cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C2-C6 alkylcarbonyl;
each R3A is independently selected from the group consisting of C1-C4 alkyl and C1-C4 haloalkyl;
each R3B is independently selected from the group consisting of H, C1-C4 alkyl and C1-C4 haloalkyl;
each R3C is independently selected from the group consisting of H and C1-C4 alkyl;
each R3D is independently selected from the group consisting of H, amino, C1-C4 alkyl and C1-C4 alkylamino;
each R3F is independently selected from the group consisting of hydroxy, halogen, cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; and
each R3G is independently selected from the group consisting of cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C2-C6 alkylcarbonyl;
provided when i) Y1 is N; Y2 is CH; Y3 is CBr; Y4 is CH; and R2 is Cl, then R3 is other than 5-CF3, 5-CN or 5-NO2; ii) Y1 is N; Y2 is CH; Y3 is CBr; Y4 is CH; and R2 is Br, then R3 is other than 5-CF3; and iii) Y1 is N; Y2 is CCH3; Y3 is CCl; Y4 is CCl; and R2 is Cl, then m is other than 0.

2. A compound of claim 1 wherein
—Y1═Y2—Y3═Y4— including the nitrogen to which Y1 and Y4 are both attached is selected from the group consisting of




Z is O;
each R1 is independently selected from the group consisting of hydrogen, halogen, cyano, SF5, CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 cyanoalkyl, C2-C4 alkylthioalkyl, SOnR1A, Si(CH3)3 and B(—OC(R1B)2C(R1B)2O—);
R2 is selected from the group consisting of halogen, C1-C4 alkyl and C1-C4 haloalkyl;
each R3 is independently selected from the group consisting of halogen, cyano, CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C8 alkylcycloalkyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C4 alkylcarbonyloxy, C2-C6 cyanoalkyl, C(═O)N(R3A)(R3B), C(═NOR3C)H, SOnR3E; a phenyl ring optionally substituted with up to 5 substituents independently selected from R3F; and a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R3F on carbon atom ring members and R3G on nitrogen atom ring members; and
m is selected from the group consisting of 0, 1 and 2.

3. A compound of claim 2 wherein
—Y1═Y2—Y3═Y4— including the nitrogen to which Y1 and Y4 are both attached is selected from the group consisting of Q-2 and Q-5;
each R1 is independently selected from the group consisting of hydrogen, halogen, cyano, CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C4 alkylthioalkyl and SOnR1A;
R2 is selected from the group consisting of halogen and C1-C4 alkyl;
each R3 is independently selected from the group consisting of halogen, cyano, CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 cyanoalkyl, SOnR3E; and a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from the group consisting of up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R3F on carbon atom ring members and R3G on nitrogen atom ring members; and
m is selected from the group consisting of 0 and 1.

4. A compound of claim 3 wherein
each R1 is independently selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and SOnR1A;
R2 is selected from the group consisting of halogen and CH3;
each R3 is independently selected from the group consisting of halogen, cyano, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C6 alkoxyalkyl and C2-C6 haloalkoxyalkyl; and
each R1A is independently selected from the group consisting of C1-C4 alkyl and C1-C4 haloalkyl.

5. A compound of claim 4 wherein
—Y1═Y2—Y3═Y4— including the nitrogen to which Y1 and Y4 are both attached is Q-2;
each R1 is independently selected from the group consisting of hydrogen, halogen, C1-C4 haloalkyl and C1-C4 haloalkoxy; and
each R3 is independently selected from the group consisting of halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl.

6. A compound of claim 4 wherein
—Y1═Y2—Y3═Y4— including the nitrogen to which Y1 and Y4 are both attached is Q-5;
each R1 is independently selected from the group consisting of hydrogen, halogen, C1-C4 haloalkyl and C1-C4 haloalkoxy; and
each R3 is independently selected from the group consisting of halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl.

7. A compound of claim 1 selected from the group consisting of
5-chloro-2-[2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]phenoxy]pyrimidine,
5-bromo-2-[2-(4-chloro-1H-pyrazol-1-yl)phenoxy]pyrimidine,
2-[2-(4-bromo-1H-pyrazol-1-yl)phenoxy]-5-chloropyrimidine,
2-[2-(4-bromo-1H-pyrazol-1-yl)phenoxy]-5-fluoropyrimidine,
5-bromo-2-[2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]phenoxy]pyrimidine,
2-(4-bromo-1H-pyrazol-1-yl)-3-[(5-chloro-2-pyrimidinyl)oxy]benzonitrile,
2-[2-(4-bromo-2H-1,2,3-triazol-2-yl)phenoxy]-5-chloropyrimidine,
3[(5-chloro-2-pyrimidinyl)oxy]-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]benzonitrile,
3-[(5-bromo-2-pyrimidinyl)oxy]-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]benzonitrile,
5-chloro-2-[2-[4-(difluoromethyl)-1H-1,2,3-triazol-1-yl]-3-fluorophenoxy]pyrimidine,
5-chloro-2-[2-[4-(trifluoromethyl)-1H-1,2,3-triazol-1-yl]phenoxy]pyrimidine,
5-chloro-2-[2-[4-(difluoromethyl)-1H-1,2,3-triazol-1-yl]phenoxy]pyrimidine,
3-[(5-fluoro-2-pyrimidinyl)oxy]-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]benzonitrile,
2-[2-(4-bromo-1H-pyrazol-1-yl)-3-fluorophenoxy]-5-chloropyrimidine,
3-[(5-chloro-2-pyrimidinyl)oxy]-2-[4-(2,2,2-trifluoroethoxy)-1H-pyrazol-1-yl]benzonitrile,
5-chloro-2-[2-[4-(2,2,2-trifluoroethoxy)-1H-pyrazol-1-yl]phenoxy]pyrimidine,
2-[2-(4-bromo-1H-pyrazol-1-yl)-3-(difluoromethyl)phenoxy]-5-chloropyrimidine,
3-[(5-chloro-2-pyrimidinyl)oxy]-2-[4-(difluoromethyl)-1H-pyrazol-1-yl]benzonitrile,
3-[(5-chloro-2-pyrimidinyl)oxy]-2-[4-(trifluoromethyl)-1H-imidazol-1-yl]benzonitrile,
5-bromo-2-[2-[4-(difluoromethyl)-1H-1,2,3-triazol-1-yl]-3-fluorophenoxy]pyrimidine and
5-chloro-2-[3-fluoro-2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]phenoxy]pyrimidine.

8. A herbicidal composition comprising a compound of claim 1 and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.

9. A herbicidal composition comprising a compound of claim 1, at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners, and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.

10. A herbicidal mixture comprising (a) a compound of claim 1, and (b) at least one additional active ingredient selected from the group consisting of (b1) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3) acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5) 5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b6) photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitors, (b10) auxin transport inhibitors, (b11) phytoene desaturase (PDS) inhibitors, (b12) 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, (b13) homogentisate solanesyl transferase (HST) inhibitors, (b14) cellulose biosynthesis inhibitors, (b15) other herbicides selected from the group consisting of mitotic disruptors, organic arsenicals, asulam, bromobutide, cinmethylin, cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol, fosamine, fosamine-ammonium, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and pyributicarb, (b16) herbicide safeners and salts of compounds of (b1) through (b16).

11. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of claim 1.

12. A method for controlling the growth of undesired vegetation in a genetically modified plants that exhibit traits of glyphosate tolerance, glufosinate tolerance, ALS herbicide tolerance, dicamba tolerance, imidazolinone herbicide tolerance, 2,4-D tolerance, HPPD tolerance or mesotrione tolerance, comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of claim 1.

13. A herbicidal mixture comprising (a) a compound of claim 1, and (b) at least one additional active ingredient selected from the group consisting of (b1) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b4) auxin mimics, (b5) 5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitors and (b12) 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors.

14. A herbicidal mixture comprising (a) a compound of claim 1, and (b) at least one additional active ingredient selected from the group consisting of 2,4-D, acetochlor, alachlor, atrazine, bromoxynil, bentazon, bicyclopyrone, carfentrazone-ethyl, cloransulam-methyl, dicamba, dimethenamid-p, florasulam, flufenacet, flumioxazin, flupyrsulfuron-methyl, fluroxypyr-meptyl, glyphosate, halauxifen-methyl, isoxaflutole, MCPA, mesotrione, metolachlor, metsulfuron-methyl, nicosulfuon, pyrasulfotole, pyroxasulfone, pyroxsulam, rimsulfuron, saflufenacil, tembotrione, thifensulfuron-methyl, topramazone and tribenuron.