# Patent

## Title
Substituted triazoles as herbicides

## Abstract

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




    
    
        wherein A, R1, Q and J are as defined in the disclosure.
    
    


Also disclosed are compositions containing the compounds 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 triazoles, 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 safe or have different sites of action.
SUMMARY OF THE INVENTION
This invention is directed to compounds of Formula 1 (including all stereoisomers), including N-oxides and salts thereof, agricultural compositions containing them and their use as herbicides:




wherein

    
    
        R1 is halogen, cyano, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C2-C6 alkylcarbonyloxy, C1-C4 hydroxyalkyl, SOn(R12), C2-C4 alkylthioalkyl, C2-C4 alkylsulfonylalkyl, C1-C4 alkylamino C2-C4 dialkylamino, C3-C6 cycloalkyl or hydroxy;
        A is a radical selected from the group consisting of
    
    






    
    
        each Y1, Y2, Y3, Y4 and Y5 is independently N or CR2, provided no more than 3 of Y1, Y2, Y3, Y4 and Y5 are N;
        each Y6, Y7 and Y8 is independently N or CR3, provided no more than 2 of Y6, Y7 and Y8 are N;
        Z is O or S;
        Q is C(R4)(R5), O, S or NR6;
        J is phenyl substituted with 1 R7 and optionally substituted with up to 2 R8; or
        J is a 6-membered aromatic heterocyclic ring substituted with 1 R7 and optionally substituted with up to 2 R8 on carbon ring members; or
        J is a 5-membered aromatic heterocyclic ring substituted with 1 R9 on carbon ring members and R11 on nitrogen ring members; and optionally substituted with 1 R10 on carbon ring members;
        each R2 is independently H, halogen, cyano, nitro, SF5, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C4 alkenyloxy, C3-C4 alkynyloxy or S(O)nR12;
        each R3 is independently H, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy or S(O)nR12;
        R4 is H, F, Cl, Br, cyano, C1-C4 alkyl, C1-C4 haloalkyl or CO2R13;
        R5 is H, F, C1-C4 alkyl, OH or OR13; or
        R4 and R5 are taken together with the carbon to which they are attached to form C(═O), C(═NOR13) or C(═N—N(R14)(R15));
        R6 is H, C1-C4 alkyl or C1-C4 haloalkyl;
        R7 is halogen, cyano, SF5, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy or S(O)nR12;
        each R8 is independently halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy or S(O)nR12; or
        R7 and R8 are taken together with two adjacent carbon atoms to form a 5-membered ring containing ring members selected from carbon atoms and up to two O atoms and up to two S atoms, and optionally substituted on carbon atom ring members with up to five halogen atoms;
        R9 is halogen, cyano, SF5, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy or S(O)nR12;
        R10 is halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy or S(O)nR12;
        R11 is C1-C4 alkyl or C1-C4 haloalkyl;
        each R12 is independently C1-C4 alkyl or C1-C4 haloalkyl;
        each R13 is independently H or C1-C4 alkyl;
        R14 is C1-C4 alkyl or C1-C4 haloalkyl;
        R15 is C1-C4 alkyl or C1-C4 haloalkyl; and
        each n is independently 0, 1 or 2;
        provided
        i) when R1 is CH3; A is A-1; Y1, Y2, Y3 and Y4 are each CH; and Y5 is CCF3 then J is other than 3-chloro-1H-1,2,4-thiadiazol-5-yl, 4-fluoro-2-pyridinyl, 4-chlorophenyl or 2,4-dichlorophenyl; and
        ii) when R1 is CH3; A is A-1; Y1, Y2, Y3 and Y4 are each CH; and Y5 is CF then J is other than 4-fluoro-3-methylphenyl.
    
    


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, 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 reagent” 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.
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. The term “cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. “Alkenyl” includes straight-chain or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, and the different butenyl isomers. “Alkenyl” also includes polyenes such as 1,2-propadienyl 1,3-butadienyl. “Alkynyl” includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl and pentynyl isomers. “Alkynyl” can also include moieties comprised of multiple triple bonds such as 1,3-butadiynyl. “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 and CH3CH2OCH2CH2. “Alkenyloxy” includes straight-chain or branched alkenyloxy moieties. Examples of “alkenyloxy” include H2C═CHCH2O, (CH3)CH═CHCH2O and CH2═CHCH2CH2O. “Alkynyloxy” includes straight-chain or branched alkynyloxy moieties. Examples of “alkynyloxy” include HC≡CCH2O and CH3C≡CCH2O. “Alkylcarbonyloxy” includes straight-chain or branched alkylcarbonyloxy moieties. Examples of “alkylcarbonyloxy” include CH3C(═O)O, (CH3)2CH2C(═O)O and CH3CH2CH2CH2C(═O)O. “Alkylthio” includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio and the different propylthio, butylthio isomers. “Alkylthioalkyl” denotes alkylthio substitution on alkyl. Examples of “alkylthioalkyl” include CH3SCH2, CH3SCH2CH2, CH3CH2SCH2 and CH3CH2SCH2CH2. Examples of “alkylsulfonyl” include CH3S(O)2—, CH3CH2S(O)2— and CH3CH2CH2S(O)2—, and the different butylsulfonyl isomers. The term “alkylsulfonylalkyl” denotes alkylsulfonyl substitution on alkyl. Examples of “alkylsulfonylalkyl” include CH3SO2CH2, CH3SO2CH2CH2, CH3CH2SO2CH2 and CH3CH2SO2CH2CH2. “Alkylthioalkoxy” denotes alkylthio substitution on alkoxy. “Hydroxyalkyl” denotes an alkyl group substituted with one hydroxy group. Examples of hydroxy alkyl include HOCH2CH2CH2—, CH3CH2CH(OH)CH2—, and CH3CH2CHOH—. “Alkylamino”, “dialkylamino” and the like, are defined analogously to the above examples.
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” and the like, is defined analogously to the term “haloalkyl”. Examples of “haloalkoxy” include CF3O—, CCl3CH2O—, HCF2CH2CH2O— and CF3CH2O—.
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 4. 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 group contains a substituent which can be hydrogen, for example R2, R3, R4, R5 and R6, 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 R8, 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” as a component of Formula 1 (e.g., substituent J) is heterocyclic. The term “ring member” refers to an atom or other moiety forming the backbone of a ring. The term “heterocyclic ring” denotes a ring in which at least one atom forming the ring backbone is not carbon, e.g., nitrogen, oxygen or sulfur. Typically a heterocyclic ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs. Unless otherwise indicated, a heterocyclic ring can be a saturated, partially unsaturated, or fully unsaturated ring. When a fully unsaturated heterocyclic ring satisfies Hückel's rule, then said ring is also called a “heteroaromatic ring” or “aromatic heterocyclic ring”. Unless otherwise indicated, heterocyclic rings and ring systems can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen. “Aromatic” indicates that each of the ring atoms is essentially in the same plane and has a p-orbital perpendicular to the ring plane, and that (4n+2) π electrons, where n is a positive integer, are associated with the ring to comply with Hückel's rule.
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 J is a 5- or 6-membered nitrogen-containing heterocyclic ring, it may be attached to the remainder of Formula 1 though any available carbon or nitrogen ring atom, unless otherwise described. As noted above, J can be (among others) phenyl optionally substituted with one or more substituents selected from a group of substituents as defined in the Summary of the Invention. An example of phenyl optionally substituted with one to five substituents is the ring illustrated as U-1 in Exhibit 1, wherein Rv is R7 and R8 as defined in the Summary of the Invention for substitution on J and r is an integer from 0 to 3 (i.e. substituted with one R7 and up to two R8).
As noted above, J can be phenyl or a 5- or 6-membered aromatic heterocyclic ring, which may be saturated or unsaturated, optionally substituted with one or more substituents selected from a group of substituents as defined in the Summary of the Invention. Examples of a 5- or 6-membered unsaturated aromatic heterocyclic ring optionally substituted with from one or more substituents include the rings U-2 through U-61 illustrated in Exhibit 1 wherein Rv is any substituent as defined in the Summary of the Invention for J (i.e. R7, R8, R9, R10 and R11) and r is an integer from 0 to 3, limited by the number of available positions on each U group. As U-29, U-30, U-36, U-37, U-38, U-39, U-40, U-41, U-42 and U-43 have only one available position, for these U groups r is limited to the integers 0 or 1, and r being 0 means that the U group is unsubstituted and a hydrogen is present at the position indicated by (Rv)r.

























Note that when J is a 5- or 6-membered saturated or unsaturated non-aromatic heterocyclic ring optionally substituted with one or more substituents selected from the group of substituents as defined in the Summary of the Invention for J, one or two carbon ring members of the heterocycle can optionally be in the oxidized form of a carbonyl moiety.
Examples of a 5-membered carbocyclic ring containing ring members selected from up to two O atoms and up to two S atoms, and optionally substituted on carbon atom ring members with up to five halogen atoms includes the rings G-1 through G-5 as illustrated in Exhibit 2 (i.e. when R7 and R8 are taken together with two adjacent carbon atoms). Note that when the attachment point on the Rv group is illustrated as floating, the Rv group can be attached to the remainder of Formula 1 through any available carbon G group by replacement of a hydrogen atom. The optional substituents corresponding to Rv can be attached to any available carbon or nitrogen by replacing a hydrogen atom. For these G rings, r is typically an integer from 0 to 5, limited by the number of available positions on each G group.




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. 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.
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.
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 (where Formula 1 as used in the following Embodiments includes N-oxides and salts thereof) the following:
Embodiment 1
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 1A
A compound of Formula 1 wherein R1 is H, halogen, cyano, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 hydroxyalkyl, SOn(R12), C2-C4 alkylthioalkyl, C2-C4 alkylsulfonylalkyl, C1-C4 alkylamino or C2-C4 dialkylamino.
Embodiment 1B
A compound of Embodiment 1A wherein R1 is other than H,
Embodiment 1C
A compound of Embodiment 1 wherein R1 is halogen, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C2-C6 alkylcarbonyloxy, C1-C4 hydroxyalkyl, SOn(R12), C2-C4 alkylthioalkyl or C2-C4 alkylsulfonylalkyl.
Embodiment 2
A compound of Embodiment 1 or 1C wherein R1 is halogen, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 hydroxyalkyl, SOn(R12), C2-C4 alkylthioalkyl or C2-C4 alkylsulfonylalkyl.
Embodiment 3
A compound of Embodiment 2 wherein R1 is halogen, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C1-C4 alkyl, C1-C4 haloalkyl or C2-C4 alkenyl.
Embodiment 4
A compound of Embodiment 3 wherein R1 is halogen, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C1-C4 alkyl or C1-C4 haloalkyl.
Embodiment 5
A compound of Embodiment 4 wherein R1 is C1-C4 alkoxy, C1-C4 haloalkoxy or C1-C4 alkyl.
Embodiment 6
A compound of Embodiment 5 wherein R1 is C1-C4 alkoxy or C1-C4 alkyl.
Embodiment 7
A compound of Embodiment 6 wherein R1 is C1-C4 alkyl.
Embodiment 7A
A compound of Embodiment 7 wherein R1 is C1-C3 alkyl.
Embodiment 7B
A compound of Embodiment 7 wherein R1 is C1-C2 alkyl.
Embodiment 8
A compound of Embodiment 7 wherein R1 is CH3.
Embodiment 8A
A compound of Embodiment 5 wherein R1 is CH3CH2O—, CH3O—, CF3CH2O— or CH3.
Embodiment 8B
A compound of Embodiment 5 wherein R1 is CH3CH2O—, CH3O— or CH3.
Embodiment 8C
A compound of Embodiment 5 wherein R1 is CH3CH2O— or CH3O—,
Embodiment 8D
A compound of Embodiment 5 wherein R1 is CH3CH2O—.
Embodiment 9
A compound of any one of Embodiments 1 through 8D wherein A is a radical selected from the group consisting of A-1 and A-2.
Embodiment 10
A compound of Embodiment 9 wherein A is A-1.
Embodiment 11
A compound of Embodiment 10 wherein each Y1, Y3, Y4 and Y5 is independently N or CR2; and Y2 is CR2.
Embodiment 12
A compound of Embodiment 11 wherein each Y1 and Y5 is independently N or CR2; and each Y2, Y3 and Y4 is CR2.
Embodiment 13
A compound of Embodiment 12 wherein Y1 is N or CR2; and each Y2, Y3, Y4 and Y5 is independently CR2.
Embodiment 14
A compound of Embodiment 13 wherein Y1 is N; and each Y2, Y3, Y4 and Y5 is independently CR2.
Embodiment 15
A compound of Embodiment 14 wherein Y1 is N; each Y2, Y3 and Y4 is CH; and Y5 is CF.
Embodiment 16
A compound of Embodiment 13 wherein each Y1, Y2, Y3 and Y4 and is CH; and Y5 is CCF3 or CF.
Embodiment 17
A compound of Embodiment 9 wherein A is A-2.
Embodiment 18
A compound of Embodiment 17 wherein each Y6 and Y7 is independently N or CR3; and Y8 is CR3.
Embodiment 19
A compound of Embodiment 18 wherein each Y6 and Y7 is N; and Y8 is CR3.
Embodiment 20
A compound of Embodiment 19 wherein each Y6 and Y7 is N; and Y8 is CH.
Embodiment 21
A compound of any one of Embodiments 1 through 9 or 17 through 20 wherein Z is S.
Embodiment 22
A compound of any one of Embodiments 1 through 21 wherein Q is C(R4)(R5), O or S.
Embodiment 23
A compound of Embodiment 22 wherein Q is C(R4)(R5) or O.
Embodiment 24
A compound of Embodiment 23 wherein Q is C(R4)(R5).
Embodiment 25
A compound of Embodiment 23 wherein Q is O.
Embodiment 26
A compound of any one of Embodiments 1 through 25 wherein J is selected from













    
    
        t is 0, 1 or 2; and
        u is 0 or 1.
    
    


Embodiment 27
A compound of Embodiment 26 wherein J is selected from J-1 through J-14 (i.e. J is a 6-membered aromatic heterocyclic ring selected from J-1 through J-14).
Embodiment 28
A compound of Embodiment 26 wherein J is selected from J-15 through J-33 (i.e. J is a 5-membered aromatic heterocyclic ring selected from J-15 through J-33).
Embodiment 29
A compound of Embodiment 26 wherein J is selected from J-1, J-2, J-3, J-4, J-5, J-6, J-7, J-9, J-12, J-17, J-18, J-20, J-22, J-26, J-29 and J-30 (i.e. all J groups prepared in Index Table A).
Embodiment 30
A compound of Embodiment 27 or 29 wherein J is selected from J-1, J-2, J-3, J-4, J-5, J-6, J-7, J-9 and J-12 (i.e. all 6-membered J groups prepared in Index Table A).
Embodiment 30A
A compound of Embodiment 27 or 29 wherein J is selected from J-2, J-3, J-4, J-5, J-6 and J-7 (i.e. all pyridine J groups).
Embodiment 30B
A compound of Embodiment 27 or 29 wherein J is selected from J-8, J-9, J-10, J-11, J-12, J-13 and J-14 (i.e. all pyrimidine J groups).
Embodiment 31
A compound of Embodiment 28 or 29 wherein J is selected from J-18, J-20, J-22, J-26, J-29 and J-30 (i.e. all 5-membered J groups prepared in Index Table A).
Embodiment 31A
A compound of Embodiment 28 wherein J is selected from J-15, J-21, J-22, J-23, J-24, J-25, J-26, J-27, J-28, J-31 and J-33 (i.e. all nitrogen containing 5-membered J groups linked through carbon).
Embodiment 31B
A compound of Embodiment 28 wherein J is selected from J-16, J-17, J-18, J-19, J-20 and J-32 (i.e. all nitrogen containing 5-membered J groups linked through nitrogen).
Embodiment 32
A compound of Embodiment 26 wherein J is selected from J-1, J-2, J-10, J-17, J-18 and J-20.
Embodiment 33
A compound of Embodiment 32 wherein J is selected from J-1, J-2, J-17 and J-18.
Embodiment 34
A compound of Embodiment 33 wherein J is J-1.
Embodiment 35
A compound of Embodiment 33 wherein J is J-2.
Embodiment 35A
A compound of any one of Embodiments 26, 27, 29, 30, 30A, 30B, 32 or 33 wherein t is 0 or 1.
Embodiment 35B
A compound of Embodiment 35A wherein t is 0.
Embodiment 35C
A compound of any one of Embodiments 26, 28, 29, 31, 31A, 31B, 32 or 33 wherein u is 0.
Embodiment 36
A compound of any one of Embodiments 1 through 26, 27, 29, 30 or 32 through 34 wherein J is other than J-1.
Embodiment 37
A compound of any one of Embodiments 1 through 36 wherein each R2 is independently H, halogen, C1-C4 alkoxy, C1-C4 alkyl or C1-C4 haloalkyl.
Embodiment 38
A compound of Embodiment 37 wherein each R2 is independently H, halogen, C1-C4 alkyl or C1-C4 haloalkyl.
Embodiment 39
A compound of Embodiment 38 wherein each R2 is independently H, F, Cl, CH3 or CF3.
Embodiment 40
A compound of Embodiment 39 wherein each R2 is independently H, F, Cl or CF3.
Embodiment 41
A compound of Embodiment 40 wherein each R2 is independently H or CF3.
Embodiment 42
A compound of Embodiment 40 wherein each R2 is independently H or F.
Embodiment 43
A compound of any one of Embodiments 1 through 42 wherein each R3 is independently H, halogen or C1-C4 haloalkyl.
Embodiment 44
A compound of Embodiment 43 wherein each R3 is independently H, F, Cl or CF3.
Embodiment 45
A compound of Embodiment 44 wherein each R3 is independently H or CF3.
Embodiment 45A
A compound of any one of Embodiments 1 through 45 wherein R4 is taken alone.
Embodiment 46
A compound of any one of Embodiments 1 through 45A wherein R4 is H, F, Cl, Br or C1-C4 alkyl.
Embodiment 47
A compound of Embodiment 46 wherein R4 is H, F or CH3.
Embodiment 48
A compound of Embodiment 47 wherein R4 is H.
Embodiment 48A
A compound of any one of Embodiments 1 through 48 wherein R5 is taken alone.
Embodiment 49
A compound of any one of Embodiments 1 through 48A wherein R5 is H, F or OH.
Embodiment 50
A compound of Embodiment 49 wherein R5 is H or F.
Embodiment 51
A compound of Embodiment 50 wherein R5 is H.
Embodiment 52
A compound of Embodiment 50 wherein R5 is F.
Embodiment 53
A compound of any one of Embodiments 1 through 45 wherein R4 and R5 are taken together with the carbon to which they are attached to form C(═O).
Embodiment 54
A compound of any one of Embodiments 1 through 53 wherein R6 is H or C1-C4 alkyl.
Embodiment 55
A compound of Embodiment 54 wherein R6 is CH3.
Embodiment 56
A compound of Embodiment 54 wherein R6 is H.
Embodiment 56A
A compound of any one of Embodiments 1 through 56 wherein R7 is taken alone.
Embodiment 57
A compound of any one of Embodiments 1 through 56A wherein R7 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy.
Embodiment 58
A compound of Embodiment 57 wherein R7 is halogen, C1-C4 alkyl or C1-C4 haloalkyl.
Embodiment 59
A compound of Embodiment 58 wherein R7 is F, CH3 or CF3.
Embodiment 60
A compound of Embodiment 59 wherein R7 is F or CF3.
Embodiment 61
A compound of Embodiment 60 wherein R7 is F.
Embodiment 62
A compound of Embodiment 60 wherein R7 is CF3.
Embodiment 62A
A compound of any one of Embodiments 1 through 62 wherein each R8 is taken alone.
Embodiment 63
A compound of any one of Embodiments 1 through 62A wherein each R8 is independently halogen or C1-C4 haloalkyl.
Embodiment 64
A compound of Embodiment 63 wherein each R8 is independently F, Cl or CF3.
Embodiment 65
A compound of Embodiment 63 wherein each R8 is F.
Embodiment 66
A compound of any one of Embodiments 1 through 56 wherein R7 and R8 are taken together with two adjacent carbon atoms to form a 5-membered ring containing ring members selected from carbon atoms and up to two O atoms, and optionally substituted on carbon atom ring members with up to five halogen atoms.
Embodiment 67
A compound of Embodiment 66 wherein R7 and R8 are taken together with two adjacent carbon atoms to form a 5-membered ring containing ring members selected from carbon atoms and up to two O atoms, and optionally substituted on carbon atom ring members with up to two halogen atoms.
Embodiment 68
A compound of Embodiment 67 wherein R7 and R8 are taken together with two adjacent carbon atoms to form a 5-membered ring containing ring members selected from carbon atoms and up to two O atoms, and substituted on carbon atom ring members with up to two F atoms.
Embodiment 69
A compound of Embodiment 68 wherein R7 and R8 are taken together with two adjacent carbon atoms to form a 2,2-difluorodioxolane ring (i.e. J is J-1B)




Embodiment 70
A compound of any one of Embodiments 1 through 69 wherein R9 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy.
Embodiment 71
A compound of Embodiment 70 wherein R9 is halogen, C1-C4 alkyl C1-C4 haloalkyl or C1-C4 alkoxy.
Embodiment 72
A compound of Embodiments 71 wherein R9 is halogen, C1-C4 alkyl or C1-C4 haloalkyl.
Embodiment 73
A compound of Embodiment 72 wherein R9 is F, CH3 or CF3.
Embodiment 74
A compound of Embodiment 73 wherein R9 is F or CF3.
Embodiment 75
A compound of Embodiment 74 wherein R9 is F.
Embodiment 76
A compound of Embodiment 74 wherein R9 is CF3.
Embodiment 77
A compound of any one of Embodiments 1 through 76 wherein R10 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy.
Embodiment 78
A compound of Embodiment 77 wherein R10 is halogen, C1-C4 alkyl or C1-C4 haloalkyl.
Embodiment 79
A compound of Embodiment 78 wherein R10 is F, CH3 or CF3.
Embodiment 80
A compound of Embodiment 79 wherein R10 is F or CF3.
Embodiment 81
A compound of Embodiment 80 wherein R10 is F.
Embodiment 82
A compound of Embodiment 80 wherein R10 is CF3.
Embodiment 83
A compound of any one of Embodiments 1 through 82 wherein R11 is C1-C4 alkyl or C1-C4 haloalkyl.
Embodiment 84
A compound of Embodiment 83 wherein R11 is C1-C4 alkyl.
Embodiment 85
A compound of Embodiment 84 wherein R11 is CH3.
Embodiment 86
A compound of any one of Embodiments 1 through 85 wherein each R12 is independently C1-C4 alkyl.
Embodiment 87
A compound of Embodiment 86 wherein each R12 is CH3.
Embodiment 88
A compound of any one of Embodiments 1 through 87 wherein each R13 is independently CH3 or CH2CH3.
Embodiment 89
A compound of Embodiment 88 wherein each R13 is CH3.
Embodiment 90
A compound of any one of Embodiments 1 through 89 wherein R14 is C1-C4 alkyl.
Embodiment 91
A compound of Embodiment 90 wherein R14 is CH3.
Embodiment 92
A compound of any one of Embodiments 1 through 91 wherein R15 is C1-C4 alkyl.
Embodiment 93
A compound of Embodiment 92 wherein R15 is CH3.
Embodiment 94
A compound of any one of Embodiments 1 through 93 wherein n is 0 or 2.
Embodiment 95
A compound of Embodiment 94 wherein n is 0.
Embodiment 96
A compound of Embodiment 94 wherein n is 2.
Embodiments of this invention, including Embodiments 1-96 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 compounds 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 1-96 above as well as any other embodiments described herein, and any combination thereof, pertain to the compositions and methods of the present invention.
Embodiment A
A compound of the Summary of the Invention wherein

    
    
        R1 is halogen, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C2-C6 alkylcarbonyloxy, C1-C4 hydroxyalkyl, SOn(R12), C2-C4 alkylthioalkyl or C2-C4 alkylsulfonylalkyl;
        A is a radical selected from the group consisting of A-1 and A-2;
        each Y1, Y3, Y4 and Y5 is independently N or CR2; and Y2 is CR2;
        each Y6 and Y7 is independently N or CR3; and Y8 is CR3;
        Z is S;
        Q is C(R4)(R5), O or S;
        J is selected from J-1 through J-33;
        t is 0, 1 or 2;
        u is 0;
        each R2 is independently H, halogen, C1-C4 alkoxy, C1-C4 alkyl or C1-C4 haloalkyl;
        each R3 is independently H, halogen or C1-C4 haloalkyl
        R4 is H, F, Cl, Br or C1-C4 alkyl;
        R5 is H, F or OH; or
        R4 and R5 are taken together with the carbon to which they are attached to form C(═O);
        R7 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy;
        R8 is independently halogen or C1-C4 haloalkyl; or
        R7 and R8 are taken together with two adjacent carbon atoms to form a 2,2-difluorodioxolane ring;
        R9 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy;
        R10 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy;
        R11 is C1-C4 alkyl or C1-C4 haloalkyl
        each R12 is independently C1-C4 alkyl;
        each R13 is independently CH3 or CH2CH3;
        R14 is C1-C4 alkyl;
        R15 is C1-C4 alkyl; and
        n is O or 2.
    
    


Embodiment B
A compound of Embodiment A wherein

    
    
        R1 is halogen, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C1-C4 alkyl, C1-C4 haloalkyl or C2-C4 alkenyl;
        each Y1 and Y5 is independently N or CR2; and each Y2, Y3 and Y4 is CR2;
        each Y6 and Y7 is N; and Y8 is CR3;
        Q is C(R4)(R5) or O;
        J is selected from J-1, J-2, J-3, J-4, J-5, J-6, J-7, J-9, J-12, J-17, J-18, J-20, J-22, J-26, J-29 and J-30;
        t is 0 or 1;
        u is 0;
        each R2 is independently H, halogen, C1-C4 alkyl or C1-C4 haloalkyl;
        each R3 is independently H, F, Cl or CF3;
        R4 is H, F or CH3;
        R5 is H or F;
        R7 is F, CH3 or CF3;
        R8 is independently F, Cl or CF3;
        R9 is halogen, C1-C4 alkyl or C1-C4 haloalkyl;
        R10 is halogen, C1-C4 alkyl or C1-C4 haloalkyl;
        R11 is C1-C4 alkyl;
        each R12 is CH3; and
        each R13 is CH3.
    
    


Embodiment C
A compound of Embodiment A wherein

    
    
        R1 is halogen, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C1-C4 alkyl or C1-C4 haloalkyl;
        A is A-1;
        Y1 is N or CR2; and each Y2, Y3, Y4 and Y5 is independently CR2;
        Q is C(R4)(R5);
        J is selected from J-1, J-2, J-10, J-17, J-18 and J-20;
        t is 0;
        each R2 is independently H, F, Cl, CH3 or CF3;
        R4 is H;
        R5 is H; and
        R7 is F or CF3.
    
    


Embodiment D
A compound of Embodiment B wherein

    
    
        R1 is C1-C4 alkoxy, C1-C4 haloalkoxy or C1-C4 alkyl;
        A is A-1;
        Y1 is N or CR2; and each Y2, Y3, Y4 and Y5 is independently CR2;
        Q is O;
        J is selected from J-1, J-2, J-17 and J-18;
        each R2 is independently H, F, Cl or CF3; and
        R7 is CF3.
    
    


Embodiment E
A compound of Embodiment D wherein

    
    
        R1 is CH3;
        each Y1, Y2, Y3, Y4 and Y5 is independently CR2;
        J is J-2;
        t is 0; and
        each R2 is independently H or F.
    
    


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

    4-[[2-(4-fluorophenyl)-5-methyl-2H-1,2,3-triazol-4-yl]oxy]-2-(trifluoromethyl)pyridine (Compound 129) and
    4-[[5-Methoxy-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine (Compound 15).


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

    4-[[2-(4-fluorophenyl)-5-methyl-2H-1,2,3-triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine (Compound 16);
    4-[[2-(4-fluorophenyl)-5-methyl-2H-1,2,3-triazol-4-yl]oxy]-2-(trifluoromethyl)pyridine (Compound 129);
    4-[[5-ethoxy-2-(4-fluorophenyl)-2H-1,2,3-triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine (Compound 196);
    4-[[5-methoxy-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine (Compound 15);
    4-[[5-methyl-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine (Compound 47);
    4-[[5-ethoxy-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine (Compound 164); and
    4-[[5-(2,2,2-trifluoroethoxy)-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine (Compound 14).


Specific embodiments also include compounds of Formula 1 selected from the group consisting of:
Compound 16, Compound 129, Compound 196, Compound 15 and Compound 47.
Specific embodiments also include compounds of Formula 1 selected from the group consisting of:
Compound 16, Compound 129 and Compound 196.
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 weeds in cereal 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 as described in the embodiments 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, difenzoquat, bromobutide, flurenol, cinmethylin, cumyluron, dazomet, dymron, methyldymron, etobenzanid, fosamine, fosamine-ammonium, metam, oxaziclomefone, oleic acid, 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, atrazine, cyanazine, desmetryne, dimethametryn, prometon, prometryne, propazine, simazine, simetryn, terbumeton, terbuthylazine, terbutryne, trietazine, hexazinone, metamitron, metribuzin, amicarbazone, bromacil, lenacil, terbacil, chloridazon, desmedipham, phenmedipham, chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, ethidimuron, fenuron, fluometuron, isoproturon, isouron, linuron, methabenzthiazuron, metobromuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron, propanil, pentanochlor, bromofenoxim, bromoxynil, ioxynil, bentazon, pyridate and pyridafol.
“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 (b2a), chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flupyrsulfuron-methyl (b2b), flupyrsulfuron-sodium, foramsulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron-methyl (including sodium salt), mesosulfuron-methyl, metazosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl (b2c), triasulfuron, tribenuron-methyl, trifloxysulfuron (including sodium salt), triflusulfuron-methyl, tritosulfuron, imazapic, imazamethabenz-methyl, imazamox, imazapyr, imazaquin, imazethapyr, cloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, bispyribac-sodium, pyribenzoxim, pyriftalid, pyrithiobac-sodium, pyriminobac-methyl, thiencarbazone, flucarbazone-sodium and propoxycarbazone-sodium.
“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 cyclopyrimorate, clodinafop, cyhalofop, diclofop, fenoxaprop, fluazifop, haloxyfop, propaquizafop, quizalofop, alloxydim, butroxydim, clethodim, cycloxydim, pinoxaden, profoxydim, 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 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, halauxifen-methyl, mecoprop, MCPA, MCPB, 2,3,6-TBA, picloram, triclopyr, quinclorac and quinmerac.
“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 paraquat and diquat.
“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, bifenox, chlomethoxyfen, fluoroglycofen-ethyl, fomesafen, halosafen, lactofen, oxyfluorfen, fluazolate, pyraflufen-ethyl, cinidon-ethyl, flumioxazin, flumiclorac-pentyl, fluthiacet-methyl, thidiazimin, oxadiazon, oxadiargyl, saflufencil, azafenidin, carfentrazone carfentrazone-ethyl, sulfentrazone, pentoxazone, benzfendizone, butafenacil, pyraclonil, profluazol, flufenpyr-ethyl and tiafenacil.
“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 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, butachlor, dimethachlor, dimethanamid, metazachlor, metolachlor, pethoxamid, pretilachlor, propachlor, propisochlor, pyroxasulfone, thenylchlor, diphenamid, napropamide, naproanilide, fenoxasulfone, flufenacet, indanofan, mefenacet, fentrazamide, anilofos, cafenstrole, piperophos 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 naptalam (also known as N-(1-naphthyl)phthalamic acid and 2-[(1-naphthalenylamino)carbonyl]benzoic acid) and diflufenzopyr.
“PDS (phytoene desaturase inhibitors) (b11) are chemical compounds that inhibit carotenoid biosynthesis pathway at the phytoene desaturase step. Examples of PDS inhibitors include norflurzon, diflufenican, picolinafen, beflubutamide, fluridone, flurochloridone and flurtamone.
“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 mesotrione, sulcotrione, topramezone, tembotrione, tefuryltrione, isoxachlortole, isoxaflutole, benzofenap, pyrasulfatole, pyrazolynate, pyrazoxyfen, bicyclopyrone, benzobicyclon, fenquinotrione and 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-(3-methoxyphenyl)-3-(3-methoxypropyl)-4(3H)-pyrimidinone (b12a).
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 and the compounds of Formulae A, B and C.




HST inhibitors also include compounds of Formulae D and E.




    
    
        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, diclobenil, flupoxam, indaziflam, 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, clomezone, fluometuron, difenzoquat, bromobutide, flurenol, cinmethylin, cumyluron, dazomet, dymron, methyldymron, methiozolon, ipfencarbazone, etobenzanid, fosamine, fosamine-ammonium, metam, oxaziclomefone, oleic acid, pelargonic acid and pyributicarb.
“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, 1-bromo-4-[(chloromethyl)sulfonyl]benzene, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon, 4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660), 2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone, naphthalic anhydride and oxabetrinil.
One or more of the following methods and variations as described in Schemes 1-23 can be used to prepare the compounds of Formula 1. The definitions of A, Q, J, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14 and R15 in the compounds of Formulae 1 through 32 below are as defined above in the Summary of the Invention unless otherwise noted. Formulae 1a-1f, 11a-b, 17a, 19a, 21a, 26a, and 27a and are various subsets of a compound of Formulae 1, 11, 17, 19, 21, 26 and 27, respectively. All substituents for Formulae 1a-1f are as defined above for Formula 1 unless otherwise noted.
Compounds of Formula 1a, 1b or 1c wherein Q is O, S or NR6 respectively can be synthesized from compounds of Formula 2 by the reaction shown in Scheme 1 using an electron-deficient aromatic or heteroaromatic compound of Formula 3 wherein X (bound though carbon) is a suitable leaving group, for example, a halogen, sulfonate or alkoxide, in the presence of an appropriate base such as potassium carbonate, cesium carbonate or potassium hydroxide. Typically the reaction is conducted in a polar aprotic solvent such as dimethylsulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidinone or acetonitrile at temperatures ranging from ambient temperature to the reflux temperature of the solvent. Compounds of Formula 3 are commercially available or their preparation is known in the art. For reaction conditions for this general coupling methodology, see Carey, F. A., Sundberg, R. J., Advanced Organic Chemistry Part B, 4th Edition; Kluwer Academic/Plenum Publishers, New York, 2001; Chapter 11.2.2 and references cited therein.




Compounds of Formula 1d wherein Q is CH2 can be synthesized from a compound of Formula 4 by the reaction shown in Scheme 2. Halomethyl compounds of Formula 4 are reacted with a suitable boronic acid or boronate ester in the presence of a palladium salt or complex such as palladium(II) acetate, tetrakis(triphenylphosphine)palladium(0) or bis(triphenylphosphine)palladium(II) chloride, an appropriate ligand and an inorganic base such as potassium phosphate, potassium carbonate or sodium carbonate. Typically the reaction is conducted in solvent such as 1,2-dimethoxyethane, 1,4-dioxane, toluene, tetrahydrofuran (or a mixture thereof) or t-butanol and water at temperatures ranging from ambient temperature to the reflux temperature of the solvent. Typical procedures using bromomethyl intermediates are disussed in Eur. J. Chem. 2011, 46(2), 488-496 and in PCT Patent Publication WO 2012/004714. A typical procedure using a chloromethyl intermediate is discussed in Angew. Chem., Int. Ed. 2011, 50(46), 10913-10916. Compounds of Formula 5 are commercially available or their preparation is known in the art.




Compounds of Formula 1d can also be synthesized from a compound of Formula 6 by the reaction shown in Scheme 3. Hydroxymethyl derivatives of Formula 6 are reacted with a suitable organomagnesium halide in the presence of a nickel salt or complex such as nickel(II) chloride, nickel(II) bromide, nickel(II) acetoacetate or bis(tricyclohexylphosphine)nickel(II) chloride and an appropriate ligand such as tricyclohexylphosphine, 1,2-bis(diphenylphosphino)ethane or 1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene. Typically the reaction is conducted in a mixture of solvents including but not limited to dibutyl ether, diisopropyl ether and toluene at temperatures ranging from ambient temperature to the reflux temperature of the solvent. For the discovery and optimization of these types of reactions, see D-G. Yu et al. in J.A.C.S. 2012, ASAP, available at http://pubs.acs.org/doi/pdf/10.1021/ja307045r. Compounds of Formula 7 are commercially available or their preparation is known in the art.




Compounds of Formula 1d (wherein Q is CH2 and J is directly bound to Q through a nitrogen atom) can be synthesized from a compound of Formula 4 by the reaction shown in Scheme 4 wherein X is a suitable leaving group, for example, a halogen or sulfonate, and wherein J is a nitrogen-containing heterocycle. The reaction is typically conducted in the presence of an appropriate base such as potassium carbonate, cesium carbonate or potassium hydroxide. Typically the reaction is conducted in a solvent such as dimethylsulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidinone or acetonitrile at temperatures ranging from ambient temperature to the reflux temperature of the solvent. Compounds of Formula 8 are commercially available or their preparation is known in the art. A typical procedure is discussed in Nature Chemical Biology 2008, 4(11), 691-699.




As shown in Scheme 5, compounds of Formula 1e wherein Q is C(═O) can be synthesized from a compound of Formula 9 and an organolithium or organomagnesium compound of Formula 10. Typically, these reactions are conducted in a solvent mixture containing tetrahydrofuran, diethyl ether or toluene at a temperature ranging from −78° C. to ambient temperature. Compounds of Formula 10 are commercially available or their preparation is known in the art. A typical procedure is disclosed in PCT Patent publication WO 2009/121939.




As shown in Scheme 6, a compound of Formula 1f can be prepared from esters of Formula 11 by general methods well known to one skilled in the art. Esters of Formula 11 can be reduced to the corresponding alcohols using a wide variety of reagents, but metal hydride reagents such as lithium aluminum hydride, diisobuyl aluminum hydride or lithium borohydride are particularly general and effective. Typically, these reductions are performed in an ethereal solvent such as diethyl ether, tetrahydrofuran or 1,2-dimethoxyethane at temperatures ranging from −78° C. to the reflux temperature of the solvent. For a comprehensive overview of the methodologies available to reduce esters to alcohols, see Larock, R. C., Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd Ed., Wiley-VCH, New York, 1999; and references cited therein.




Compounds of Formula 1a, 1b or 1c can alternatively be synthesized by the reaction of N-alkoxy triazolium salts of Formula 12 with a compound of Formula 13 in the presence of a base as shown in Scheme 7. The counterion is typically a non-nucleophilic anion such as tetrafluoroborane or trifluoromethanesufonate. Appropriate solvents for these substitution reactions include acetonitrile, methanol and tetrahydrofuran either alone or mixtures thereof. These reactions are usually conducted at temperatures ranging from 0° C. to the reflux temperature of the solvent. Bases such as potassium carbonate, sodium hydride, sodium carbonate, potassium tert-butoxide, and many others can be employed. The use of an exogenous base is not necessary when anilines are used as the nucleophile. A typical procedure using a phenol is disclosed in UK Patent Application GB 2193493. A typical procedure using a thiophenol is disclosed in Pest. Sci. 1996, 48(2), 189-196. A typical procedure using an aniline is disclosed in J. Chem. Soc., Perkin Transactions 1 1981, 503-513. Compounds of Formula 13 are commercially available or their preparation is known in the art.




Compounds of Formula 1a, 1b or 1c can also be synthesized from a compound of Formula 14 by the reaction shown in Scheme 8 of an electron-deficient aromatic or heteroaromatic compound of Formula 15 wherein X is a suitable leaving group, for example, a halogen, sulfonyl (such as alkylsulfonyl, trifluoromethanesulfonyl, phenylsulfonyl or p-toluenesulfonyl) or lower alkoxide, in the presence of an appropriate base such as potassium carbonate, cesium carbonate or potassium hydroxide. Typically the reaction is conducted in a solvent such as dimethylsulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidinone or acetonitrile at temperatures ranging from ambient temperature to the reflux temperature of the solvent. Compounds of Formula 15 are commercially available or their preparation is known in the art. For reaction conditions for this general coupling methodology, see Carey, F. A.; Sundberg, R. J., Advanced Organic Chemistry Part B, 4th Edition; Kluwer Academic/Plenum Publishers, New York, 2001; Chapter 11.2.2 and references cited therein. In cases where a compound of Formula 15 lacks sufficiently electron-withdrawing substituents to enable the aromatic substitution in a practical time frame, a suitable nitro-containing aromatic or heteroaromatic compound of Formula 16 can be used to enhance the reaction rate. It is obvious to one skilled in the art that reduction of the nitro group followed by diazotization/reduction of the resulting aniline will satisfactorily remove the activating nitro group. A typical procedure for this series of steps is disclosed in Angew. Chem., Int. Ed. 2010, 49(11), 2018-2022. Compounds of Formulae 15 and 16 are commercially available or their preparation is known in the art.




As shown in Scheme 9, a compound of Formula 2a can be synthesized by the reaction of triazole N-oxides of Formula 17 with a suitable activator such as an acid halide, acid anhydride or silyl halide followed by acidic or basic hydrolysis. The activator is selected from acetyl chloride, acetic anhydride (which can also act as the solvent) or trimethylsilyl iodide. Other solvents appropriate for this reaction include chloroform and dichloromethane. These reactions are usually conducted at temperatures ranging from 0° C. to the reflux temperature of the solvent. Basic hydrolysis is typically conducted with a base such as sodium hydroxide, potassium hydroxide or potassium carbonate in a solvent such as water, methanol, ethanol or a mixture tetrahydrofuran and water at temperatures ranging from 0° C. to the reflux temperature of the solvent. Acidic hydrolysis is typically conducted with, but not limited to, an acid such as hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or acetic acid in a solvent such as chloroform, toluene, methanol, ethanol or water (or a mixture of said solvents) at temperatures ranging from 0° C. to the reflux temperature of the solvent. A typical procedure using acetyl chloride as the activator followed by basic hydrolysis is disclosed in Bull. Chim. Belg. 1997, 106(11), 717-728. A typical procedure using trimethylsilyl iodide as the activator followed by acidic hydrolysis is discussed in Acta Chem. Scan. 1996, 50(6), 549-555.




As shown in Scheme 10, a compound of Formula 4 is a particularly useful intermediate for use in the preparation of a compound of Formula 1 and can be prepared from several different precursors. Using reaction conditions similar to those discussed in the method of Scheme 6, esters of Formula 18 can be converted to alcohols of Formula 6. Alcohols of Formula 6 can then be converted to the compounds of Formula 4 using a wide range of reagents such as thionyl chloride, phosphorus trichloride, phosphorus tribromide, triphenylphosphine/bromine, triphenylphosphine/iodine. Alternatively, halogenation methods using hydrohalides in solvents such as acetic acid, acetonitrile, diethyl ether, tetrahydrofuran, dichloromethane, water or a mixture of water with the aforementioned solvents, at temperatures ranging from 0° C. to the reflux temperature of the solvent can be used. Typical procedures for the production of a bromomethyl compound are disclosed in PCT Patent Publication WO 2005/115383. Alternatively, a compound of Formula 6 can be prepared by the reaction of a compound of Formula 19 using trifluoroacetic anhydride as described in Bull. Soc. Chim. Belg. 1997, 106(11), 717-727. Alcohols of Formula 6 can subsequently be converted to a compound of Formula 4 by the methods described above for Scheme 10.




Alternatively, a compound of Formula 4 can be prepared from triazole N-oxides of Formula 19 by the one-step procedure shown in Scheme 11. Reaction of a compound of Formula 19 with halogenating agent such as phosphorus oxybromide or phosphorus oxychloride, in solvents such as 1,4-dioxane, 1,2-dichloroethane, chloroform or toluene, at temperatures ranging from ambient to the reflux temperature of the solvent affords compounds of Formula 4 directly.




As shown in Scheme 12, bromides of Formula 4 can also be prepared by radical bromination of a compound of Formula 20 using a brominating agent such as N-bromosuccinimide or bromine, a radical initiator such as azobisisobutyronitrile, benzoyl peroxide or a UV light source, in solvents such as carbon tetrachloride or trifluoromethylcyclohexane at temperatures ranging from ambient to the reflux temperature of the solvent. A typical procedure for the synthesis of a bromomethyl compound is disclosed in PCT Patent publication WO 2007/071900.




As illustrated in Scheme 13, using reaction conditions similar to those discussed in the method of Scheme 8, triazoles of Formula 21 can be converted into N-aryl triazoles of Formula 11a which are useful for preparing alcohols of Formula 1f as depicted in Scheme 6. Compounds of Formulae 15 (where R is lower alkyl) and 16 are commercially available or their preparation is known in the art.




Compounds of Formula 18 can be prepared as shown in Scheme 14. Reaction of a dicarbonyl compound of Formula 22 with a diazonium salt in the presence of an acid acceptor results in a coupling reaction to form a compound of Formula 23. Suitable solvents include lower carboxylic acids such as acetic acid, lower alcohols such as methanol or ethanol, water, and mixtures thereof. Acid acceptors such as, but not limited to, alkali carbonates, bicarbonates, phosphates and acetates can be employed in this reaction. Compounds of Formula 23 can be cyclized to compounds of Formula 18 by reaction with an ammonium salt in the presence of an oxidizing agent. Suitable ammonium salts include halides, acetate, and sulfate among others. The oxidizing agent is preferably, but not limited to, a Cu(II) salt such as copper(II) sulfate, copper(II) chloride or copper(II) bromide or N-iodosuccinimide. Typical conditions for this procedure are described in U.S. Patent Application 20060014785.




Similarly, Compounds of Formula 11b can be prepared as shown in Scheme 15. The coupling reaction of a dicarbonyl compound of Formula 24 with a diazonium salt in the presence of an acid acceptor can form a compound of Formula 25. Suitable solvents include lower carboxylic acids such as acetic acid, lower alcohols such as methanol or ethanol, water, and mixtures thereof. Acid acceptors such as, but not limited to, alkali carbonates, bicarbonates, phosphates and acetates can be employed in this reaction. Compounds of Formula 25 can be cyclized to compounds of Formula 11b by reaction with an ammonium salt in the presence of an oxidizing agent. Suitable ammonium salts include halides, acetate, and sulfate among others. The oxidizing agent is preferably, but not limited to, a Cu(II) salt such as copper(II) sulfate, copper(II) chloride or copper(II) bromide or N-iodosuccinimide. Typical conditions for this procedure are described in U.S. Patent Application 20060014785.




As shown in Scheme 16, compounds of Formula 12 can be synthesized by the reaction of triazole N-oxides of Formula 17 with strong alkylating reagents such as trimethyloxonium tetrafluoroborate or methyl trifluoromethanesulfonate. Preferred solvents for this substitution reaction include dichloromethane, chloroform and 1,2-dichloroethane. The reactions are usually conducted at temperatures ranging from 0° C. to the reflux temperature of the solvent. Typical procedures are disclosed in J. Chem. Soc., Perkin Transactions 1 1982, 2749-2756 and references cited therein.




As shown in Scheme 17, a compound of Formula 21 can be obtained by removal of an appropriate protecting group such as a trialkylsilyl group, (i.e. trimethylsilyl), or an optionally substituted benzyl group (i.e. benzyl or p-methoxybenzyl) from compounds of Formula 26. The p-methoxybenzyl group is of particular value as an intermediate to prepare a compound of Formula 1 via a compound of Formula 4 as shown in Scheme 2. Deprotection of a compound of Formula 26 wherein PG is p-methoxybenzyl is typically performed via one of the following two methods. First, acid-catalyzed deprotection is usually conducted in neat trifluoroacetic acid or as a mixture with a solvent such as dichloromethane or 1,2-dichloroethane at temperatures ranging from 0° C. to the reflux temperature of the solvent. A typical procedure is disclosed in PCT Patent publication WO 2005/073192. Second, the p-methoxybenzyl group can be removed using an oxidant such as ceric ammonium nitrate or 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in a mixture of acetonitrile and water or a mixture of dichloromethane and water, respectively. The useful temperature range for these reactions is from ambient to the reflux temperature of the solvent. A typical procedure is disclosed in PCT Patent Publication WO 2007/071900.




As illustrated in Scheme 18, a compound of Formula 23 can be prepared from a compound of Formula 27 using reaction conditions similar to those discussed in the method of Scheme 17. For an exemplary preparation of a compound of Formula 27 wherein R1 is either a lower alkoxy group or a haloalkoxy group, see PCT Patent Publication WO 2007/096576.




A compound of Formula 19a wherein R1 can independently be H or C1-C4 alkyl can be synthesized by the reaction of a compound of Formula 28 with a suitable oxidant as shown in Scheme 19. Suitable oxidants include a Cu(II) salt, such as copper(II) sulfate, copper(II) chloride or copper(II) bromide, or N-iodosuccinimide. The preferred solvents for the reaction are pyridine, carbon tetrachloride, methanol, ethanol, water and aqueous mixtures of the aforementioned solvents. The reactions are usually conducted at temperatures ranging from 0° C. to the reflux temperature of the solvent. A typical procedure is disclosed in J. Chem. Soc., Perkin Transactions 1 1981, 503-513. Compounds of Formula 28 are commercially available or their preparation is known in the art.




In a similar fashion, a compound of Formula 17a wherein R1 is H or C1-C4 alkyl can be synthesized by the reaction of a compound of Formula 29 with a suitable oxidant as shown in Scheme 20. Suitable oxidants and solvents include those discussed for Scheme 19. The reactions are usually conducted at temperatures ranging from 0° C. to the reflux temperature of the solvent. A typical procedure is disclosed in J. Chem. Soc., Perkin Transactions 1 1981, 503-513. Compounds of Formula 29 are commercially available or their preparation is known in the art. A typical procedure is disclosed in J. Chem. Soc., Perkin Transactions 1 1981, 503-513.




A compound of Formula 26a can be synthesized by the reaction of triazoles of Formula 30 with a wide range of carbon, oxygen, sulfur and nitrogen nucleophiles including cyanide, dialkyl malonates, aryl acetonitriles, aryl acetic acids, aryl acetic esters, amines, phenols, alcohols, thiophenols, alkyl thiols and anilines, optionally in the presence of a base, as shown in Scheme 21. Typical bases including sodium hydride, sodium methoxide, sodium ethoxide, cesium carbonate, potassium carbonate or potassium tert-butoxide can be employed. Solvents suitable for this substitution reaction are dimethylsulfoxide, N,N-dimethylformamide, tetrahydrofuran, lower alkyl alcohols and acetonitrile at temperatures ranging from ambient temperature to the reflux temperature of the solvent. For the preparation of compounds of Formula 30, see J. Het. Chem. 1981, 18(6), 1117-1122.




Similarly, a compound of Formula 27a can be synthesized by the reaction of triazoles of Formula 31 with a wide range of carbon, nitrogen, oxygen and sulfur nucleophiles including cyanide, dialkyl malonates, aryl acetonitriles, aryl acetic acids, aryl acetic esters, amines, phenols, alcohols, thiophenols, alkyl thiols and anilines, optionally in the presence of a base, as shown in Scheme 22. Typical bases including sodium hydride, sodium methoxide, sodium ethoxide, cesium carbonate, potassium carbonate or potassium tert-butoxide can be employed. Solvents suitable for this substitution reaction are dimethylsulfoxide, N,N-dimethylformamide, tetrahydrofuran, lower alkyl alcohols and acetonitrile at temperatures ranging from ambient temperature to the reflux temperature of the solvent. For the preparation of compounds of Formula 31, see J. Het. Chem. 1981, 18(6), 1117-1122.




As shown in Scheme 23, a compound of Formulae 21a or 14a wherein Q is C═O or CH2 respectively can be synthesized by the reaction of compounds of Formula 32 with an inorganic azide salt, typically sodium azide. The preferred solvents for the substitution reaction are dimethylsulfoxide, N,N-dimethylformamide, tetrahydrofuran, lower alkyl alcohols, acetonitrile and water or a mixture thereof at temperatures ranging from 0° C. to the reflux temperature of the solvent. A typical procedure is disclosed in J. Org. Chem. 2008, 73(11), 4317-4319. A compound of Formula 32 is commercially available or its preparation is known in the art.




The synthesis of 1,2,3-triazoles and derivatives thereof are well known in the literature. For a general discussion of their synthesis, see Rachwal, A. R, Katritzky, A. R., 1,2,3-Triazoles, Comprehensive Heterocyclic Chemistry III 2008, 5, 1-158 and Tome, A. C., Product class 13: 1,2,3-Triazoles, Science of Synthesis 2004, 13, 415-601.
It is recognized by one skilled in the art that various functional groups can be converted into others to provide different compounds 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 compounds 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 compounds 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 compounds 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, 2nd ed.; Wiley: New York, 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 compounds 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 order presented to prepare the compounds of Formula 1.
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 Synthesis Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Steps in the following Synthesis 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 unless otherwise noted; “s” means singlet, “m” means multiplet, “br s” means broad singlet. Mass spectra (MS) are reported as the molecular weight of the highest isotopic abundance parent ion (M+1) formed by addition of H+(molecular weight of 1) to the molecule, observed by mass spectrometry using atmospheric pressure chemical ionization (AP+) where “amu” stands for atomic mass units. The presence of molecular ions containing one or more higher atomic weight isotopes of lower abundance (e.g., 37Cl, 81Br) is not reported.
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; “s” means singlet, “d” means doublet, “t” means triplet, “q” means quartet, “m” means multiplet and “br s” means broad singlet.
Synthesis Example 1
Preparation of 4-[[5-methoxy-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine (Compound 15)
Step A: Preparation of 4-Methyl-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole 1-oxide
To a stirred solution of anti-pyruvic aldehyde 1-oxime (2.67 g, 30.7 mmol) in diethyl ether (50 mL) was added 4-(trifluoromethyl)phenylhydrazine (5.40 g, 30.7 mmol). The reaction mixture was stirred at 23° C. for 2 h, then concentrated under reduced pressure. The crude residue was dissolved in 15% aqueous pyridine (150 mL). A solution of copper(II) sulfate pentahydrate (15.31 g, 61.3 mmol) in water (75 mL) was added at once. The resulting mixture was stirred at reflux for 17 h, then cooled to 0° C. Ethyl acetate (100 mL) was added and the mixture was filtered through Celite® diatomaceaous filter aid. The layers were separated, and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with 1.0 M aqueous hydrochloric acid (3×50 mL). The organic layer was dried (MgSO4), filtered, and evaporated under reduced pressure. The residue was purified by chromatography on silica gel, eluting with 0 to 50% ethyl acetate in hexanes, to afford the title compound (5.84 g) as a colorless solid.
1H NMR δ 2.37 (s, 3H), 7.32 (s, 1H), 7.75-7.79 (m, 2H), 8.15-8.20 (m, 2H).
Step B: Preparation of 1-Methoxy-4-methyl-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazolium tetrafluoroborate (1:1)
To a stirred solution of 4-methyl-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole 1-oxide (i.e. the product of Step A, 5.22 g, 21.5 mmol) in dichloromethane (100 mL) was added trimethyloxonium tetrafluoroborate (4.13 g, 27.9 mmol). The reaction mixture was stirred at 23° C. for 65 h, then concentrated under reduced pressure to afford a crude mixture of the title compound as a brown oil which was used directly in the next step without further purification.
1H NMR δ 2.60 (s, 3H), 4.47 (s, 3H), 7.90-7.98 (m, 4H), 9.01 (s, 1H).
Step C: Preparation of 4-methoxy-5-methyl-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole
Sodium metal (0.25 g, 11.0 mmol) was stirred at 23° C. in methanol (10 mL) until a clear solution was obtained. This sodium methoxide solution was added to crude 1-methoxy-4-methyl-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazolium tetrafluoroborate (1:1) (i.e. the product of Step B, 1.1 g, 3.2 mmol). The reaction mixture was stirred at 23° C. for 6 h, during which time a white precipitate formed. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (40 mL, 10 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel eluting with 0 to 10% ethyl acetate in hexanes to afford the title compound (0.82 g) as a colorless solid.
1H NMR δ 2.28 (s, 3H), 4.05 (s, 3H), 7.64-7.68 (m, 2H), 7.96-8.00 (m, 2H).
Step D: Preparation of 4-(bromomethyl)-5-methoxy-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole
To a solution of 4-methoxy-5-methyl-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole (i.e. the product of Step C, 0.82 g, 3.2 mmol) in carbon tetrachloride (10 mL) was added N-bromosuccinimide (0.62 g, 3.5 mmol) and 2,2′-azobis(2-methylpropionitrile) (0.026 g, 0.2 mmol). The reaction mixture was heated at reflux for 2 h, then an additional portion of 2,2′-azobis(2-methylpropionitrile) (0.026 g, 0.2 mmol) was added. The reaction mixture was heated at reflux for 2.5 h, cooled to room temperature, diluted with water (10 mL) and extracted with dichloromethane (2×10 mL). The organic layers were dried (Na2SO4) and concentrated under reduced pressure to afford a crude material containing approximately 66% (by weight) of the title compound as determined by 1H NMR. The crude material was used directly in the next step without further purification.
1H NMR δ 4.11 (s, 3H), 4.53 (s, 2H), 7.67-7.72 (m, 2H), 8.02-8.07 (m, 2H).
Step E: Preparation of 4-[[5-methoxy-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine
To a solution of 4-(bromomethyl)-5-methoxy-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole (i.e. the product of Step D, 0.525 g, 66 weight %, 1.0 mmol) in tetrahydrofuran/water (3:1, 4 mL total), was added tetrakis(triphenylphosphine)palladium(0) (0.059 g, 0.05 mmol), potassium phosphate tribasic (0.43 g, 2.0 mmol) and 2-(trifluoromethyl)pyridine-4-boronic acid pinacol ester (0.42 g, 1.5 mmol). The mixture was heated to reflux and stirred for 17 h. The reaction mixture was diluted with water (20 mL) and extracted twice with ethyl acetate (25 mL, 15 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel eluting with 10% ethyl acetate in hexanes to afford the title compound (0.12 g) as a pale yellow solid.
1H NMR δ 4.06 (s, 3H), 4.09 (s, 2H), 7.42-7.45 (m, 1H), 7.63-7.72 (m, 3H), 8.00-8.04 (m, 2H), 8.64-8.67 (m, 1H).
Synthesis Example 2
Preparation of 4-methoxy-2-[4-(trifluoromethyl)phenyl]-5-[[3-(trifluoromethyl)-1H-pyrazol-1-yl]methyl]-2H-1,2,3-triazole (Compound 17)
Step A: Preparation of 4-methoxy-2-[4-(trifluoromethyl)phenyl]-5-[[3-(trifluoromethyl)-1H-pyrazol-1-yl]methyl]-2H-1,2,3-triazole
To a solution of 4-(bromomethyl)-5-methoxy-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole (i.e. the product of Example 1, Step D) (0.25 g, 66 weight %, 0.5 mmol) in N,N-dimethylformamide (2 mL total), was added 3-(trifluoromethyl)pyrazole (0.082 g, 0.6 mmol) and anhydrous potassium carbonate (0.21 g, 1.5 mmol). The mixture was heated to 55° C. and stirred for 75 min. The reaction mixture was cooled to 23° C., diluted with water (20 mL) and extracted with ethyl acetate (15 mL). The organic layer was washed with water (10 mL) and saturated aqueous sodium chloride solution (10 mL), dried (MgSO4) and concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel eluting with 0 to 40% ethyl acetate in hexanes to afford the title compound (0.098 g) as a colorless oil.
1H NMR δ 4.07 (s, 3H), 5.44 (s, 2H), 6.53-6.55 (m, 1H), 7.55-7.59 (m, 1H), 7.67-7.72 (m, 2H), 8.02-8.07 (m, 2H).
Synthesis Example 3
Preparation of 4-methyl-2-[4-(trifluoromethyl)phenyl]-5-[[5-(trifluoromethyl)-3-thienyl]oxy]-2H-1,2,3-triazole (Compound 1)
Step A: Preparation of 4-methyl-2-[4-(trifluoromethyl)phenyl]-5-[[5-(trifluoromethyl)-3-thienyl]oxy]-2H-1,2,3-triazole
Potassium tert-butoxide (0.30 g, 2.6 mmol) and 5-trifluoromethylthiophene-3-one (0.44 g, 2.6 mmol) were dissolved in acetonitrile (4 mL). A solution of crude 1-methoxy-4-methyl-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazolium tetrafluoroborate (1:1) (i.e., the product of Example 1, Step B, 0.70 g, 2.0 mmol) in acetonitrile (4 mL) was added at once. The reaction mixture was stirred at 23° C. for 27 h. The reaction mixture was diluted with water (20 mL) and extracted with diethyl ether (2×25 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel eluting with 0 to 5% ethyl acetate in hexanes to afford the title compound (0.105 g) as a colorless solid.
1H NMR δ 2.37 (s, 3H), 7.35-7.37 (m, 1H), 7.41-7.43 (m, 1H), 7.67-7.73 (m, 2H), 8.02-8.06 (m, 2H).
Synthesis Example 4
Preparation of 4-[[2-(4-fluorophenyl)-5-methyl-2H-1,2,3-triazol-4-yl]oxy]-2-(trifluoromethyl)pyridine (Compound 129)
Step A: Preparation of 2-(4-fluorophenyl)-4-methyl-2H-1,2,3-triazole 1-oxide
To a stirred solution of anti-pyruvic aldehyde 1-oxime (3.4 g, 39 mmol) in diethyl ether (75 mL) was added 4-fluorophenylhydrazine hydrochloride (5.85 g, 36 mmol). The reaction mixture was stirred at 23° C. for 16 h, and then concentrated under reduced pressure. The crude residue was dissolved in pyridine (120 mL). A solution of copper(II) sulfate pentahydrate (18 g, 72 mmol) in water (55 mL) was added dropwise over 4 min. The resulting mixture was stirred at reflux for 2 h. The mixture was concentrated under reduced pressure to remove excess pyridine. To the mixture was added 1.0 M aqueous hydrochloric acid. The mixture was extracted with ethyl acetate and the organic layer was separated and washed with 1.0 M aqueous hydrochloric acid until a clear amber organic layer was obtained. The organic layer was dried (MgSO4), filtered, and evaporated under reduced pressure to afford the title compound (6.6 g) as a colorless solid. The title compound was used directly in the next step without further purification.
1H NMR δ 2.35 (s, 3H), 7.17-7.22 (m, 2H), 7.29 (s, 1H), 7.86-7.91 (m, 2H).
Step B: Preparation of 2-(4-fluorophenyl)-5-methyl-2H-1,2,3-triazol-4-yl acetate
2-(4-Fluorophenyl)-4-methyl-2H-1,2,3-triazole 1-oxide (i.e. the product of Step A, 6.6 g, 34 mmol) was added to acetic anhydride (47 mL, 500 mmol), and the reaction mixture was stirred at reflux for 28 h. The reaction was concentrated under reduced pressure. The residue was taken up in ethyl acetate, washed successively with water and saturated aqueous sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure to afford the title compound (7.8 g) as a beige solid. The title compound was used directly in the next step without further purification.
1H NMR δ 2.26 (s, 3H), 2.38 (s, 3H), 7.10-7.16 (m, 2H), 7.88-7.94 (m, 2H).
Step C: Preparation of 2-(4-fluorophenyl)-2,3-dihydro-5-methyl-4H-1,2,3-triazol-4-one
2-(4-Fluorophenyl)-5-methyl-2H-1,2,3-triazol-4-yl acetate (i.e. the product of Step B, 7.8 g, 33 mmol) was suspended in methanol (150 mL). A solution of sodium hydroxide (7 M, 22 mL, 140 mmol) was added over several minutes with stirring during which time the mixture became homogeneous and then stirred at 23° C. for 18 h. The reaction was concentrated under reduced pressure to remove excess methanol. The remaining residue was diluted with water (200 mL) and washed with hexanes. The aqueous layer was acidified with concentrated hydrochloric acid during which time a thick creamy precipitate formed. The mixture was diluted with water and stirred for 30 min. The precipitate was filtered and washed well with water. The moist solid was dissolved in ethyl acetate, dried (MgSO4) and concentrated under reduced pressure to afford the title compound (6.1 g) as a beige solid. The title compound was used directly in the next step without further purification.
1H NMR δ 2.33 (s, 3H), 7.12-7.19 (m, 2H), 7.73-7.80 (m, 2H), 9.73 (s, 1H).
Step D: Preparation of 4-[[2-(4-fluorophenyl)-5-methyl-2H-1,2,3-triazol-4-yl]oxy]-2-(trifluoromethyl)pyridine
To a solution of 2-(4-fluorophenyl)-2,3-dihydro-5-methyl-4H-1,2,3-triazol-4-one (i.e. the product of Step C, 3.1 g, 16 mmol) in N,N-dimethylformamide (70 mL) was added anhydrous potassium carbonate (6.2 g, 45 mmol) under an atmosphere of nitrogen. 4-Chloro-2-trifluoromethyl-pyridine (2.9 g, 16 mmol) was added and the mixture was heated to 100° C. for 20 h. The reaction mixture was diluted with water, then extracted with diethyl ether. The organic layer was washed successively with water and saturated aqueous sodium chloride solution, dried (MgSO4), filtered, and concentrated under reduced pressure. The crude material was purified by chromatography on silica gel eluting with 0 to 20% ethyl acetate in hexanes to obtain the title compound (4.2 g) as a viscous light yellow oil that solidified upon standing to form an off-white solid.
1H NMR δ 2.32 (s, 3H), 7.14-7.19 (m, 2H). 7.28-7.32 (m, 1H), 7.50-7.54 (m, 1H), 7.90-7.96 (m, 2H), 8.65-8.69 (m, 1H).
Synthesis Example 5
Preparation of 5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole-4-methanol (Compound 114)
Step A: Preparation of 1-(azidomethyl)-4-methoxybenzene
To a stirred solution of 4-methoxybenzyl chloride (25.0 g, 156 mmol) in N,N-dimethylformamide (75 mL) was added sodium azide (11.5 g, 177 mmol). The reaction mixture was stirred at 23° C. for 15 h, then diluted with water (300 mL). The mixture was extracted with diethyl ether (3×75 mL) and the combined organic layers were washed with water (2×100 mL). The organic layer was dried (MgSO4), filtered, and evaporated under reduced pressure to afford the title compound (25.5 g) as a pale yellow oil. The title compound was used directly in the next step without further purification.
1H NMR δ 3.82 (s, 3H), 4.27 (s, 2H), 6.88-6.93 (m, 2H), 7.22-7.27 (m, 2H).
Step B: Preparation of ethyl 5-hydroxy-1-[(4-methoxyphenyl)methyl]-1H-1,2,3-triazole-4-carboxylate
Sodium metal (3.8 g, 164 mmol) was added to absolute ethanol (200 mL). The mixture was stirred under reflux until a clear solution was obtained. Diethyl malonate (26.3 g, 164 mmol) was added to this solution which was again heated to reflux, and a solution of 1-(azidomethyl)-4-methoxybenzene (i.e. the product of Step A, 25.5 g, 156 mmol) in ethanol (50 mL) was added at once. The reaction mixture was stirred at reflux for 24 h then the reaction mixture was concentrated to dryness under reduced pressure. The residue was diluted with water (100 mL) and acidified to pH 2 with 1 M aqueous hydrochloric acid, stirred for 30 min, and the solid was filtered off and washed with water. The solid was dried over phosphorus pentoxide. The solid was stirred in chloroform (500 mL) and the insoluble solids were filtered off. Hexanes (400 mL) were added to precipitate the product, which was removed by filtration and dried to afford the title compound (12.0 g) as a beige solid.
1H NMR δ 1.35-1.40 (m, 3H), 3.78 (s, 3H), 4.36-4.43 (m, 2H), 5.30 (s, 2H), 6.15 (br s, 1H) 6.83-6.88 (m, 2H), 7.27-7.32 (m, 2H).
Step C: Preparation of ethyl 5-chloro-1-[(4-methoxyphenyl)methyl]-1H-1,2,3-triazole-4-carboxylate
Ethyl 5-hydroxy-1-[(4-methoxyphenyl)methyl]-1H-1,2,3-triazole-4-carboxylate (i.e. the product of Step B, 10.0 g, 36.1 mmol) was suspended in anhydrous toluene (300 mL) under a nitrogen atmosphere. Phosphorus pentachloride (8.3 g, 39.8 mmol) was added and the mixture was stirred at 40° C. for 90 min. during which time a clear yellow solution was formed. The reaction was concentrated under reduced pressure to remove most of the toluene. The resulting residue was diluted with diethyl ether (150 mL) and washed with saturated aqueous sodium bicarbonate solution (70 mL) and water (70 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford the crude product which was recrystallized twice from hexanes (200 mL, 100 mL) to afford the title compound (6.0 g) as a pale yellow solid.
1H NMR δ 1.38-1.43 (m, 3H), 3.79 (s, 3H), 4.40-4.46 (m, 2H), 5.50 (s, 2H), 6.85-6.89 (m, 2H), 7.24-7.29 (m, 2H).
Step D: Preparation of ethyl-1-[(4-methoxyphenyl)methyl]-5-[(3-(trifluoromethoxy)phenoxy]-1H-1,2,3-triazole-4-carboxylate
To a solution of 3-(trifluoromethoxy)phenol (0.99 g, 5.6 mmol) in N,N-dimethylformamide (10 mL) was added sodium hydride (0.23 g, 5.8 mmol, 60% dispersion in oil). The mixture was stirred at 23° C. for 45 min. then ethyl 5-chloro-1-[(4-methoxyphenyl)methyl]-1H-1,2,3-triazole-4-carboxylate (i.e. the product of Step C, 1.50 g, 5.1 mmol) was added. The reaction mixture was heated to 75° C. for 90 h. Additional sodium hydride (0.06 g, 1.5 mmol) and 3-(trifluoromethoxy)phenol (0.25 g, 1.4 mmol) were added and the mixture was stirred at 75° C. for 45 h. The reaction mixture was concentrated to dryness under reduced pressure. The resulting residue was taken up in ethyl acetate (50 mL) and washed successively with water (2×50 mL) and saturated aqueous sodium chloride solution (50 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford the crude product. The crude material was purified by chromatography on silica gel eluting with 0 to 60% ethyl acetate in hexanes to obtain the title compound (1.52 g) as a yellow oil.
1H NMR δ 1.07-1.11 (m, 3H), 3.74 (s, 3H), 4.15-4.21 (m, 2H), 5.38 (s, 2H), 6.60-6.65 (m, 2H), 6.73-6.78 (m, 2H), 6.94-6.99 (m, 1H), 7.15-7.20 (m, 2H), 7.22-7.26 (m, 1H).
Step E: Preparation of ethyl 5-[3-(trifluoromethoxy)phenoxy]-2H-1,2,3-triazole-4-carboxylate
A solution of ethyl-1-[(4-methoxyphenyl)methyl]-5-[(3-(trifluoromethoxy)phenoxy]-1H-1,2,3-triazole-4-carboxylate (i.e. the product of Step D, 1.50 g, 3.4 mmol) in trifluoroacetic acid (35 mL) was heated to 65° C. with stirring for 5 h. The reaction mixture was concentrated to dryness under reduced pressure. The residue was taken up in ethyl acetate (50 mL) and washed with saturated aqueous sodium bicarbonate solution (30 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford the crude product. The crude material was purified by chromatography on silica gel eluting with 0 to 40% ethyl acetate in 1-chlorobutane to obtain the title compound (0.90 g) as a beige solid.
1H NMR δ 1.28-1.32 (m, 3H), 4.36-4.42 (m, 2H), 7.02-7.12 (m, 3H), 7.35-7.40 (m, 1H), 12.62 (br s, 1H).
Step F: Preparation of ethyl 2-[2-nitro-4-(trifluoromethyl)phenyl]-5-[3-(trifluoromethoxy)phenoxy]-2H-1,2,3-triazole-4-carboxylate
To a solution of ethyl 5-[3-(trifluoromethoxy)phenoxy]-2H-1,2,3-triazole-4-carboxylate (i.e. the product of Step E, 0.55 g, 1.7 mmol) in N,N-dimethylformamide (5 mL) was added anhydrous potassium carbonate (0.48 g, 3.5 mmol) and 4-fluoro-3-nitrobenzotrifluoride (0.29 mL, 2.1 mmol). The mixture was heated to 80° C. with stirring for 90 min. The reaction mixture was concentrated to dryness under reduced pressure. The resulting residue was diluted with water (10 mL) and extracted with ethyl acetate (30 mL, 15 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford the crude product. The crude material was purified by chromatography on silica gel eluting with 0 to 20% ethyl acetate in hexanes to obtain the title compound (0.76 g) as a pale yellow oil.
1H NMR δ 1.36-1.41 (m, 3H), 4.42-4.48 (m, 2H), 7.07-7.21 (m, 3H), 7.41-7.45 (m, 1H), 7.96-7.99 (m, 1H), 8.10-8.14 (m, 1H).
Step G: Preparation of 2-(2-amino-4-trifluoromethyl-phenyl)-5-(3-trifluoromethoxy-phenoxy)-2H-[1,2,3]triazole-4-carboxylic acid ethyl ester
To a solution of ethyl 2-[2-nitro-4-(trifluoromethyl)phenyl]-5-[3-(trifluoromethoxy)phenoxy]-2H-1,2,3-triazole-4-carboxylate (i.e. the product of Step F, 0.76 g, 1.5 mmol) in acetonitrile (30 mL) was added a solution of sodium hydrosulfite (1.31 g, 7.5 mmol) in water (20 mL). The mixture was stirred at 23° C. for 2.5 h. The reaction mixture was diluted with saturated aqueous sodium chloride solution (30 mL) and extracted with ethyl acetate (2×50 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford the title compound (0.70 g) as a pale yellow solid. The title compound was used directly in the next step without further purification.
1H NMR δ 1.31-1.36 (m, 3H), 4.38-4.44 (m, 2H), 7.00-7.18 (m, 5H), 7.39-7.44 (m, 1H), 7.98-8.01 (m, 1H).
Step H: Preparation of ethyl 5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole-4-carboxylate
To a solution of ethyl 2-[2-amino-4-(trifluoromethyl)phenyl]-5-[3-(trifluoromethoxy)phenoxy]-2H-1,2,3-triazole-4-carboxylate (i.e. the product of Step G, 0.70 g, 1.5 mmol) in ethanol (20 mL) was added concentrated sulfuric acid (2 mL). The stirring mixture was cooled to −20° C., and then isopentyl nitrite (0.91 g, 8.8 mmol) was added dropwise over 5 min. The reaction mixture was stirred at −20° C. for 1 h, after which an aqueous solution of hypophosphorus acid (3.9 g, 29.4 mmol, 50% in water) was added. The solution was stirred at 23° C. for 14 h. The reaction mixture was diluted with saturated aqueous sodium chloride solution (20 mL), extracted with ethyl acetate (2×40 mL), and washed with saturated aqueous sodium bicarbonate solution (2×20 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford the crude residue which was purified by chromatography on silica gel eluting with 0 to 15% ethyl acetate in hexanes to obtain the title compound (0.55 g) as a colorless solid.
1H NMR δ 1.33-1.38 (m, 3H), 4.40-4.46 (m, 2H), 7.07-7.12 (m, 1H), 7.17-7.21 (m, 2H), 7.39-7.44 (m, 1H), 7.73-7.78 (m, 2H), 8.15-8.19 (m, 2H).
Step I: Preparation of 5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole-4-methanol
To a solution of ethyl 5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole-4-carboxylate (i.e. the product of Step H, 0.39 g, 0.8 mmol) in anhydrous tetrahydrofuran (6 mL) that was cooled to 0° C. was added a solution of lithium aluminum hydride in tetrahydrofuran (1.0 M, 0.8 mL, 0.8 mmol). The reaction mixture was stirred at 0° C. for 20 min., after which the reaction was quenched with the addition of ethyl acetate (5 mL). The mixture was stirred at 23° C. for 5 min., and then water (6 drops) was added. The mixture was stirred for 5 min., and then sodium sulfate was added. The mixture was stirred for 5 min., and then the mixture was filtered and concentrated under reduced pressure to obtain the title compound (0.35 g, 100%) as a pale yellow oil. The title compound was used directly in the next step without further purification.
1H NMR δ 1.90-1.95 (m, 1H), 4.80-4.84 (m, 2H), 7.05-7.09 (m, 1H), 7.18-7.23 (m, 2H), 7.38-7.44 (m, 1H), 7.70-7.74 (m, 2H), 8.05-8.09 (m, 2H).
Synthesis Example 6
Preparation of 4-methyl-5-[3-(trifluoromethoxy)phenoxy]-2-[(4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole (Compound 119)
Step A: Preparation of 4-(Bromomethyl)-5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl)-2H-1,2,3-triazole
5-[3-(Trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole-4-methanol (i.e. the product of Example 5, Step I, 0.17 g, 0.4 mmol) was suspended in 33% hydrobromic acid in acetic acid (2 mL) and 48% hydrobromic acid in water (2 mL). The mixture was heated to reflux with stirring for 4 h. The reaction mixture was cooled to 0° C. and basified with 50% aqueous sodium hydroxide solution. The reaction mixture was diluted with water (20 mL), extracted with ethyl acetate (3×15 mL), and washed with saturated aqueous sodium bicarbonate solution (10 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to obtain the title compound (0.19 g) as a pale yellow solid. The title compound was used directly in the next step without further purification.
1H NMR δ 4.56 (s, 2H), 7.07-7.11 (m, 1H), 7.22-7.26 (m, 2H), 7.40-7.45 (m, 1H), 7.70-7.74 (m, 2H), 8.04-8.08 (m, 2H).
Step B: Preparation of 4-methyl-5-[3-(trifluoromethoxy)phenoxy]-2-[(4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole
A reaction vial was charged with a magnetic stir bar, 4-(bromomethyl)-5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl)-2H-1,2,3-triazole (i.e. the product of Step A, 0.075 g, 0.16 mmol) and palladium on carbon (5 weight %, 0.033 g, 0.03 mmol). The vial was purged with nitrogen gas, and then absolute ethanol (5 mL) was added. The vial was purged and backfilled with hydrogen gas 10 times. The solution was stirred at 23° C. for 6 h under a balloon of hydrogen gas. The reaction mixture was quenched with triethylamine (0.1 mL), stirred for 5 min., filtered, and concentrated under reduced pressure. The residue was diluted with water (5 mL) and extracted with ethyl acetate (2×5 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to obtain the title compound (0.046 g,) as a beige solid.
1H NMR δ 2.32 (s, 3H), 7.02-7.06 (m, 1H), 7.12-7.17 (m, 2H), 7.37-7.42 (m, 1H), 7.68-7.73 (m, 2H), 8.02-8.07 (m, 2H).
Synthesis Example 7
Preparation of 4-(methoxymethyl)-5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole (Compound 115)
Step A: Preparation of 4-(methoxymethyl)-5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole
To a stirred solution of 5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole-4-methanol (i.e. the product of Example 5, Step I, 0.075 g, 0.18 mmol) in anhydrous tetrahydrofuran (2 mL) was added sodium hydride (0.011 g, 0.28 mmol, 60% dispersion in oil). After 15 min., iodomethane (0.017 mL, 0.27 mmol) was added. The mixture was stirred at 23° C. for 1.75 h. The reaction mixture was diluted with water (20 mL), extracted with diethyl ether (3×15 mL), and washed with saturated aqueous sodium chloride solution (10 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford the crude product which was purified by chromatography on silica gel eluting with 0 to 10% ethyl acetate in hexanes to obtain the title compound (0.045 g.) as a clear, colorless oil.
1H NMR δ 3.43 (s, 3H), 4.56 (s, 3H), 7.04-7.08 (m, 1H), 7.17-7.22 (m, 2H), 7.38-7.43 (m, 1H), 7.69-7.74 (m, 2H), 8.06-8.11 (m, 2H).
Synthesis Example 8
Preparation of 4-(fluoromethyl)-5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole (Compound 116)
Step A: Preparation of 4-(fluoromethyl)-5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole
To a stirred solution of 5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole-4-methanol (i.e. the product of Example 5, Step I, 0.075 g, 0.18 mmol) in anhydrous dichloromethane (4 mL) cooled to −78° C. was added (diethylamino)sulfur trifluoride (0.032 mL, 0.24 mmol). The mixture was stirred for 2 h during which time the temperature increase to −30° C. The reaction mixture was diluted with saturated aqueous sodium bicarbonate solution (5 mL), extracted with ethyl acetate (3×15 mL), and washed with saturated aqueous sodium chloride solution (10 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford the crude product which was purified by chromatography on silica gel eluting with 0 to 10% ethyl acetate in hexanes to obtain the title compound (0.052 g) as a yellow solid.
1H NMR δ 5.44-5.46 (m, 2H), 7.07-7.11 (m, 1H), 7.21-7.25 (m, 2H), 7.40-7.45 (m, 1H), 7.71-7.76 (m, 2H), 8.07-8.12 (m, 2H).
Synthesis Example 9
Preparation of 4-ethyl-5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole (Compound 125)
Step A: Preparation of 4-ethyl-5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole
To a suspension of copper(I) cyanide (0.037 g, 0.41 mmol) in anhydrous tetrahydrofuran (2 mL) at −78° C. under a nitrogen atmosphere was added a solution of methyllithium in diethyl ether (1.6 M, 0.54 mL, 0.86 mmol). The mixture was stirred at 0° C. until a clear, colorless solution formed, and then the solution was cooled back to −78° C. To the methylcuprate solution was added a solution of 4-(bromomethyl)-5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl)-2H-1,2,3-triazole (i.e. the product of Example 6, Step A, 0.100 g, 0.21 mmol) in anhydrous tetrahydrofuran (4 mL). The mixture was stirred for 1 h. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (5 mL) and stirred vigorously at 23° C. until the solution turned deep blue in color. The reaction mixture was extracted with ethyl acetate (2×10 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford the crude product which was purified by chromatography on silica gel eluting with 0 to 10% ethyl acetate in hexanes to obtain the title compound (0.038 g) as a clear, colorless oil.
1H NMR δ 1.29-1.35 (m, 3H), 2.68-2.75 (m, 2H), 7.01-7.06 (m, 1H), 7.11-7.17 (m, 2H), 7.36-7.42 (m, 1H), 7.68-7.72 (m, 2H), 8.03-8.07 (m, 2H).
Synthesis Example 10
Preparation of 4-[[2-(2,4-difluorophenyl)-5-methyl-2H-1,2,3-triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine (Compound 54)
Step A: Preparation of 2-(2,4-difluorophenyl)-4,5-dimethyl-2H-1,2,3-triazole 1-oxide
To a stirred solution of anti-pyruvic aldehyde 1-oxime (2.2 g, 22.2 mmol) in diethyl ether (50 mL) was added 2,4-difluorophenylhydrazine hydrochloride (4.0 g, 22.2 mmol) and pyridine (2 mL). The reaction mixture was stirred at 23° C. for 64 h. The solid that formed was removed by filtration and washed with diethyl ether. The filtrate was concentrated under reduced pressure. The crude residue was dissolved in pyridine (100 mL). A solution of copper(II) sulfate pentahydrate (11.1 g, 44.4 mmol) in water (60 mL) was added at once and the resulting mixture was stirred at reflux for 20 h. The mixture was diluted with water and extracted with diethyl ether. The combined organic layers were washed with 1.0 M aqueous hydrochloric acid, dried (MgSO4) and concentrated under reduced pressure to afford the crude product. The crude material was purified by chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes to obtain the title compound (1.98 g) as an orange solid.
1H NMR δ 2.26 (s, 3H), 2.33 (s, 3H), 7.01-7.07 (m, 2H), 7.48-7.54 (m, 1H).
Step B: Preparation of [2-(2,4-difluoro-phenyl)-5-methyl-2H-[1,2,3]triazol-4-yl]-methanol
To a solution of 2-(2,4-difluorophenyl)-4,5-dimethyl-2H-1,2,3-triazole 1-oxide (i.e. the product of Step A, 1.78 g, 7.0 mmol) in tetrahydrofuran (14 mL) was added trifluoroacetic anhydride (2.5 mL, 17.5 mmol). The reaction mixture was stirred at 110° C. in the microwave for 75 min. The mixture was diluted with ethyl acetate, washed successively with 1.0 M aqueous sodium hydroxide and 50% aqueous sodium hydroxide, dried (MgSO4) and concentrated under reduced pressure to afford the crude product. The crude material was purified by chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes to obtain the title compound (0.59 g) as a colorless solid.
1H NMR δ 1.79 (br s, 1H), 2.43 (s, 3H), 4.82 (s, 2H), 6.96-7.05 (m, 2H), 7.70-7.76 (m, 1H).
Step C: Preparation of 4-(bromomethyl)-2-(2,4-difluorophenyl)-5-methyl-2H-1,2,3-triazole
2-(2,4-Difluorophenyl)-5-methyl-2H-1,2,3-triazole-4-methanol (i.e. the product of Step B, 0.70 g, 3.1 mmol) was suspended in 48% hydrobromic acid in water (16 mL). The mixture was heated to reflux with stirring for 2 h. The reaction mixture was diluted with water, cooled to 0° C. and basified with 50% aqueous sodium hydroxide solution. The reaction mixture was extracted with ethyl acetate, dried (MgSO4) and concentrated under reduced pressure to obtain the title compound (0.75 g) as a pale yellow oil. The title compound was used directly in the next step without further purification.
1H NMR δ 2.43 (s, 3H), 4.58 (s, 2H), 6.96-7.05 (m, 2H), 7.72-7.78 (m, 1H).
Step D: Preparation of 4-[[2-(2,4-difluorophenyl)-5-methyl-2H-1,2,3-triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine
To a solution of 4-(bromomethyl)-2-(2,4-difluorophenyl)-5-methyl-2H-1,2,3-triazole (i.e. the product of Step C, 0.30 g, 1.0 mmol) in tetrahydrofuran/water (3:1, 4 mL total), was added tetrakis(triphenylphosphine)palladium(0) (0.058 g, 0.05 mmol), potassium phosphate tribasic (0.43 g, 2.0 mmol) and 2-(trifluoromethyl)pyridine-4-boronic acid pinacol ester (0.31 g, 1.15 mmol). The mixture was heated to 70° C. and stirred for 96 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The crude residue was purified by twice by chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes, and then was purified by reverse-phase chromatography on C18 silica gel to afford the title compound (0.18 g) as a colorless solid.
1H NMR δ 2.30 (s, 3H), 4.17 (s, 2H), 6.97-7.06 (m, 2H), 7.37-7.41 (m, 1H), 7.60-7.63 (m, 1H), 7.72-7.78 (m, 1H), 8.64-8.68 (m, 1H).
Synthesis Example 11
Preparation of 4-[[5-ethoxy-2-(4-fluorophenyl)-2H-1,2,3-triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine (Compound 196)
Step A: Preparation of ethyl 5-ethoxy-2-(4-fluorophenyl)-2H-1,2,3-triazole-4-carboxylate
A stirred mixture of 4-fluoroaniline (11.1 g, 100 mmol) in water (50 mL) and concentrated hydrochloric acid (19 mL) was cooled to −15° C. To this mixture was added a previously cooled (0° C.) solution of sodium nitrite (7.6 g, 110 mmol) in water (25 mL) over 5 min. Ice was added directly to the reaction to maintain the temperature below 5° C. After the addition was complete, the reaction was stirred at 0° C. for 15 min. Sodium acetate (41.0 g, 500 mmol) was added followed by ethyl 3-ethoxy-3-iminopropionate (15.9 g, 100 mmol). A yellow precipitate formed immediately. The suspension was stirred at 23° C. for 30 min., and then the solid was filtered and washed with water (40 mL). The still wet hydrazone was dissolved in pyridine (150 mL). A solution of copper (II) sulfate (49.7 g, 199 mmol) in water (150 mL) was added at once. The dark mixture was heated to 90° C. for 4 h. The majority of the pyridine ( ̃100 mL) was removed under vacuum. The residue was diluted with ethyl acetate (200 mL), water (100 mL) and 2 M sulfuric acid (80 mL). The resulting emulsion was filtered through Celite® diatomaceaous earth filter aid. The organic layer was washed with 2 M sulfuric acid (2×100 mL), dried (MgSO4) and concentrated under reduced pressure. The resulting crude mixture was recrystallized from ethanol (80 mL) to obtain the title compound (15.1 g) as a pale red solid.
1H NMR δ 1.40-1.45 (m, 3H), 1.49-1.54 (m, 3H), 4.41-4.51 (m, 4H), 7.13-7.18 (m, 2H), 7.99-8.04 (m, 2H).
Step B: Preparation of 5-ethoxy-2-(4-fluorophenyl)-N-methoxy-N-methyl-2H-1,2,3-triazole-4-carboxamide
To an oven-dried flask under a nitrogen atmosphere was added N,O-dimethylhydroxylamine hydrochloride (2.8 g, 28.6 mmol) to which a solution of trimethylaluminum (2.0 M in toluene, 14.3 mL, 28.6 mmol) was added at 0° C. and stirred for 30 min. Ethyl 5-ethoxy-2-(4-fluorophenyl)-2H-1,2,3-triazole-4-carboxylate (i.e. the product of Step A, 4.0 g, 14.3 mmol) was added and the resulting solution was stirred at 23° C. for 4 h. The reaction mixture was cooled to 0° C. and carefully quenched by the dropwise addition of water (2 mL). Dichloromethane, (50 mL), sodium sulfate and water (3 mL) were added sequentially to the mixture which was then stirred for 20 min. at 23° C. The mixture was dried (Na2SO4 and MgSO4) and concentrated under reduced pressure to obtain the title compound (3.7 g) as an orange solid.
1H NMR δ 1.46-1.51 (m, 3H), 3.39 (s, 3H), 3.86 (s, 3H), 4.43-4.49 (m, 2H), 7.12-7.18 (m, 2H), 7.93-7.98 (m, 2H).
Step C: Preparation of [5-ethoxy-2-(4-fluorophenyl)-2H-1,2,3-triazol-4-yl][2-(trifluoromethyl)-4-pyridinyl]methanone
A solution of isopropylmagnesium chloride lithium chloride complex (1.3 M in THF, 8.5 mL, 11.0 mmol) was added to a solution of 4-iodo-2-(trifluoromethyl)pyridine (3.0 g, 11.0 mmol) in tetrahydrofuran (10 mL) cooled to 0° C. After 10 minutes, the solution was stirred at 23° C. for 35 min. The dark reddish brown solution was then cooled to −78° C. A solution of 5-ethoxy-2-(4-fluorophenyl)-N-methoxy-N-methyl-2H-1,2,3-triazole-4-carboxamide (i.e. the product of Step B, 2.5 g, 8.5 mmol) in tetrahydrofuran (25 mL) was added. The solution was stirred at 23° C. for 22 h. The reaction was quenched by the addition of a saturated aqueous ammonium chloride solution (10 mL) and water (10 mL). The mixture was extracted with ethyl acetate (2×40 mL), dried (MgSO4) and concentrated under reduced pressure to obtain the crude product. The crude residue was purified by chromatography on silica gel eluting with 0 to 20% ethyl acetate in hexanes to afford the title compound (1.8 g) as a colorless solid.
1H NMR δ 1.53-1.58 (t, 3H), 4.54-4.60 (m, 2H), 7.19-7.24 (m, 2H), 8.00-8.04 (m, 2H), 8.22-8.26 (m, 1H), 8.45-8.47 (m, 1H), 8.94-8.98 (m, 1H).
Step D: Preparation of 4-[[5-ethoxy-2-(4-fluorophenyl)-2H-1,2,3-triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine
To a solution of [5-ethoxy-2-(4-fluorophenyl)-2H-1,2,3-triazol-4-yl][2-(trifluoromethyl)-4-pyridinyl]methanone (i.e. the product of Step C, 2.7 g, 7.1 mmol) in acetic acid (15 mL) was added iodine (1.8 g, 7.1 mmol) and hypophosphorous acid (50% in water, 3.1 mL, 28.4 mmol). The mixture was heated to 110° C. under a nitrogen atmosphere for 6 h. The reaction mixture was cooled to 23° C. and neutralized to  ̃pH 7 with 1 M NaOH and a saturated aqueous sodium bicarbonate solution. The mixture was extracted with ethyl acetate (2×15 mL), dried (MgSO4) and concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel eluting with 0 to 20% ethyl acetate in hexanes to afford the title compound (2.1 g) as an off-white solid.
1H NMR δ 1.39-1.44 (t, 3H), 4.08 (s, 2H), 4.33-4.39 (m, 2H), 7.09-7.15 (m, 2H), 7.42-7.46 (m, 1H), 7.66-7.68 (m, 1H), 7.84-7.88 (m, 2H), 8.63-8.66 (m, 1H).
By the procedures described herein together with methods known in the art, the following compounds of Tables 1 to 126 can be prepared. The following abbreviations are used in the Tables which follow: n means normal, i means iso, Me means methyl, Et means ethyl, Pr means propyl, i-Pr means isopropyl, Ph means phenyl, OMe means methoxy, OEt means ethoxy and SMe means methylthio.
In the following Tables 1 to 125, J-1A, J-2A, J-10A, J-17A, J-17B, J-18A, J-18B, J-20A, J-22A and J-29A refer to the following structures:











TABLE 1










   1









J is J-2A; Q is O; R1 is Me; and A is











A

















Ph(4-F)



Ph(4-CF3)



Ph(4-Cl)



Ph(4-Br)



Ph(4-SF5)



Ph(4-OCF3)



Ph(4-SCH3)



Ph(4-OCH3)



Ph(4-CN)



Ph(4-Me)



Ph



Ph(3-F)



Ph(3-CF3)



Ph(3-Cl)



Ph(3-Br)



Ph(3-SF5)



Ph(3-OCF3)



Ph(3-SMe)



Ph(3-OMe)



Ph(3-CN)



Ph(3-Me)



Ph(2-F)



Ph(2-CF3)



Ph(2-Cl)



Ph(2-Br)



Ph(2,4-di-F)



Ph(3,4-di-F)



Ph(2,5-di-F)



Ph(2,4,6-tri-F)



Ph(2-Cl,4-F)



Ph(3-Cl,4-F)



Ph(4-F,3-CF3)



Ph(2-F,4-CF3)



Ph(3-F,4-CF3)



Ph(3-Cl,4-CF3)



Ph(2-Cl,4-CF3)



Ph(4-Cl,3-CF3)



2-Pyridinyl



3-Pyridinyl



4-Pyridinyl



2-Pyridinyl(5-CF3)



2-Pyridinyl(5-Cl)



4-Pyridinyl(2-CF3)



4-Pyridinyl(2-Cl)



2-Pyridinyl(6-CF3)



3-Pyridinyl(5-CF3)



5-Pyridinyl(2-CF3)



2-Pyrazinyl(5-CF3)



3-Pyridazinyl(6-CF3)



2-Pyridinyl(5-F)



4-Pyridinyl(2-F)



2-Pyridinyl(6-F)



3-Pyridinyl(5-F)



3-Pyridinyl(6-F)



2-Pyrimidinyl(5-Cl)



2-Pyrimidinyl(5-CF3)



4-Pyrimidinyl(2-CF3)



2-Pyrimidinyl(4-CF3)



2-Thienyl(5-Cl)



2-Thienyl(5-CF3)



2-Thiazolyl(4-CF3)



1,2,4-Thiadiazol-5-yl(3-CF3)










Table 2 is constructed in the same manner except that the Row Heading “J is J-2A; Q is O, R1 is Me; and A is” is replaced with the Row Heading listed for Table 2 below (i.e. “J is J-2A; Q is O; R1 is Et; and A is”). Therefore the first entry in Table 2 is a compound of Formula 1 wherein R1 is Et; Q is O; A is Ph(4-F) (i.e. 4-fluorophenyl); and J is J-2A. Tables 3 through 125 are constructed similarly.












Table
Row Heading
















2
J is J-2A; Q is O; R1 is Et; and A is


3
J is J-2A; Q is O; R1 is n-Pr; and A is


4
J is J-2A; Q is O; R1 is i-Pr; and A is


5
J is J-2A; Q is O; R1 is OMe; and A is


6
J is J-2A; Q is O; R1 is SMe; and A is


7
J is J-2A; Q is O; R1 is OCHF2; and A is


8
J is J-2A; Q is O; R1 is CH2OCH3; and A is


9
J is J-2A; Q is O; R1 is OEt; and A is


10
J is J-2A; Q is O; R1 is OCH2CF3; and A is


11
J is J-2A; Q is CH2; R1 is Me; and A is


12
J is J-2A; Q is CH2; R1 is Et; and A is


13
J is J-2A; Q is CH2; R1 is n-Pr; and A is


14
J is J-2A; Q is CH2; R1 is i-Pr; and A is


15
J is J-2A; Q is CH2; R1 is OMe; and A is


16
J is J-2A; Q is CH2; R1 is SMe; and A is


17
J is J-2A; Q is CH2; R1 is OCHF2; and A is


18
J is J-2A; Q is CH2; R1 is CH2OCH3; and A is


19
J is J-2A; Q is CH2; R1 is OEt; and A is


20
J is J-2A; Q is CH2; R1 is OCH2CF3; and A is


21
J is J-1A; Q is O; R1 is Me; and A is


22
J is J-1A; Q is O; R1 is Et; and A is


23
J is J-1A; Q is O; R1 is n-Pr; and A is


24
J is J-1A; Q is O; R1 is i-Pr; and A is


25
J is J-1A; Q is O; R1 is OMe; and A is


26
J is J-1A; Q is O; R1 is SMe; and A is


27
J is J-1A; Q is O; R1 is OCHF2; and A is


28
J is J-1A; Q is O; R1 is CH2OCH3; and A is


29
J is J-1A; Q is O; R1 is OEt; and A is


30
J is J-1A; Q is O; R1 is OCH2CF3; and A is


31
J is J-1A; Q is CH2; R1 is Me; and A is


32
J is J-1A; Q is CH2; R1 is Et; and A is


33
J is J-1A; Q is CH2; R1 is n-Pr; and A is


34
J is J-1A; Q is CH2; R1 is i-Pr; and A is


35
J is J-1A; Q is CH2; R1 is OMe; and A is


36
J is J-1A; Q is CH2; R1 is SMe; and A is


37
J is J-1A; Q is CH2; R1 is OCHF2; and A is


38
J is J-1A; Q is CH2; R1 is CH2OCH3; and A is


39
J is J-1A; Q is CH2; R1 is OEt; and A is


40
J is J-1A; Q is CH2; R1 is OCH2CF3; and A is


41
J is J-10A; Q is O; R1 is Me; and A is


42
J is J-10A; Q is O; R1 is Et; and A is


43
J is J-10A; Q is O; R1 is OMe; and A is


44
J is J-10A Q is O; R1 is OCHF2; and A is


45
J is J-10A; Q is CH2; R1 is Me; and A is


46
J is J-10A; Q isCH2; R1 is Et; and A is


47
J is J-10A; Q is CH2; R1 is OMe; and A is


48
J is J-10A; Q is CH2; R1 is OCHF2; and A is


49
J is J-29A; Q is O; R1 is Me; and A is


50
J is J-29A; Q is O; R1 is Et; and A is


51
J is J-29A; Q is O; R1 is OMe; and A is


52
J is J-29A; Q is O; R1 is OCHF2; and A is


53
J is J-29A; Q is CH2; R1 is Me; and A is


54
J is J-29A; Q is CH2; R1 is Et; and A is


55
J is J-29A; Q is CH2; R1 is OMe; and A is


56
J is J-29A; Q is CH2; R1 is OCHF2; and A is


57
J is J-2A; Q is C═O; R1 is Me; and A is


58
J is J-2A; Q is C═O; R1 is Et; and A is


59
J is J-2A; Q is C═O; R1 is OMe; and A is


60
J is J-2A; Q is C═O; R1 is OCHF2; and A is


61
J is J-1A; Q is C═O; R1 is Me; and A is


62
J is J-1A; Q is C═O; R1 is Et; and A is


63
J is J-1A; Q is C═O; R1 is OMe; and A is


64
J is J-JA; Q is C═O; R1 is OCHF2; and A is


65
J is J-2A; Q is S; R1 is Me; and A is


66
J is J-2A; Q is S; R1 is Et; and A is


67
J is J-2A; Q is S; R1 is OMe; and A is


68
J is J-2A; Q is S; R1 is OCHF2; and A is


69
J is J-1A; Q is S; R1 is Me; and A is


70
J is J-1A; Q is S; R1 is Et; and A is


71
J is J-1A; Q is S; R1 is OMe; and A is


72
J is J-1A; Q is S; R1 is OCHF2; and A is


73
J is J-2A; Q is NH; R1 is Me; and A is


74
J is J-2A; Q is NH; R1 is Et; and A is


75
J is J-2A; Q is NH; R1 is OMe; and A is


76
J is J-2A; Q is NH; R1 is OCHF2; and A is


77
J is J-1A; Q is NH; R1 is Me; and A is


78
J is J-1A; Q is NH; R1 is Et; and A is


79
J is J-1A; Q is NH; R1 is OMe; and A is


80
J is J-1A; Q is NH; R1 is OCHF2; and A is


81
J is J-2A; Q is CHF; R1 is Me; and A is


82
J is J-2A; Q is CHF; R1 is Et; and A is


83
J is J-2A; Q is CHF; R1 is OMe; and A is


84
J is J-2A; Q is CHF; R1 is OCHF2; and A is


85
J is J-1A; Q is CHF; R1 is Me; and A is


86
J is J-1A; Q is CHF; R1 is Et; and A is


87
J is J-1A; Q is CHF; R1 is OMe; and A is


88
J is J-1A; Q is CHF; R1 is OCHF2; and A is


89
J is J-22A; Q is O; R1 is Me; and A is


90
J is J-22A; Q is O; R1 is Et; and A is


91
J is J-22A; Q is O; R1 is OMe; and A is


92
J is J-22A; Q is O; R1 is OCHF2; and A is


93
J is J-22A; Q is CH2; R1 is Me; and A is


94
J is J-22A; Q is CH2; R1 is Et; and A is


95
J is J-22A; Q is CH2; R1 is OMe; and A is


96
J is J-22A; Q is CH2; R1 is OCHF2; and A is


97
J is J-2A; Q is O; R1 is Cl; and A is


98
J is J-2A; Q is CH2; R1 is Cl; and A is


99
J is J-1A; Q is O; R1 is Br; and A is


100
J is J-1A; Q is CH2; R1 is Br; and A is


101
J is J-18A; Q is CH2; R1 is Et; and A is


102
J is J-18A; Q is CH2; R1 is Me; and A is


103
J is J-18A; Q is CH2; R1 is OMe; and A is


104
J is J-18A; Q is CH2; R1 is OCHF2; and A is


105
J is J-18A; Q is CH2; R1 is Cl; and A is


106
J is J-20A; Q is CH2; R1 is Et; and A is


107
J is J-20A; Q is CH2; R1 is Me; and A is


108
J is J-20A; Q is CH2; R1 is OMe; and A is


109
J is J-20A; Q is CH2; R1 is OCHF2; and A is


110
J is J-20A; Q is CH2; R1 is Cl; and A is


111
J is J-17A; Q is CH2; R1 is Et; and A is


112
J is J-17A; Q is CH2; R1 is Me; and A is


113
J is J-17A; Q is CH2; R1 is OMe; and A is


114
J is J-17A; Q is CH2; R1 is OCHF2; and A is


115
J is J-17A; Q is CH2; R1 is Cl; and A is


116
J is J-17B; Q is CH2; R1 is Et; and A is


117
J is J-17B; Q is CH2; R1 is Me; and A is


118
J is J-17B; Q is CH2; R1 is OMe; and A is


119
J is J-17B; Q is CH2; R1 is OCHF2; and A is


120
J is J-17B; Q is CH2; R1 is Cl; and A is


121
J is J-18B; Q is CH2; R1 is Et; and A is


122
J is J-18B; Q is CH2; R1 is Me; and A is


123
J is J-18B; Q is CH2; R1 is OMe; and A is


124
J is J-18B; Q is CH2; R1 is OCHF2; and A is


125
J is J-18B; Q is CH2; R1 is Cl; and A is









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 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 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. 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,
   1-50
40-99   
0-50


Suspensions, 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), 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 and γ-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 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 Tables A and B. 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 129
98.5%



silica aerogel
0.5%



synthetic amorphous fine silica
1.0%










Example B
Wettable Powder
















Compound 14
65.0%



dodecylphenol polyethylene glycol ether
2.0%



sodium ligninsulfonate
4.0%



sodium silicoaluminate
6.0%



montmorillonite (calcined)
23.0%










Example C
Granule
















Compound 15
10.0%



attapulgite granules (low volatile matter,
90.0%



0.71/0.30 mm; U.S.S. No. 25-50 sieves)










Example D
Extruded Pellet
















Compound 16
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 47
10.0%



polyoxyethylene sorbitol hexoleate
20.0%



C6-C10 fatty acid methyl ester
70.0%










Example F
Microemulsion
















Compound 129
5.0%



polyvinylpyrrolidone-vinyl
30.0%



copolymer acetate



alkylpolyglycoside
30.0%



glyceryl monooleate
15.0%



water
20.0%










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 intention 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 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, cyclopyrimorate (6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 4-morpholinecarboxylate), clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-olamine, cloransulam-methyl, cumyluron, cyanazine, cycloate, 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 (2-[[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxo-2-quinoxalinyl]carbonyl]-1,3-cyclohexanedione), 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, 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, methiozolin, 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, 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, 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 (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), tiocarbazil, topramezone, tralkoxydim, tri-allate, triafamone, triasulfuron, triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tridiphane, trietazine, trifloxysulfuron, trifluralin, triflusulfuron-methyl, tritosulfuron and vernolate. 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, N-(aminocarbonyl)-2-methylbenzenesulfonamide, benoxacor, BCS (1-bromo-4-[(chloromethyl)sulfonyl]benzene), cloquintocet-mexyl, cyometrinil, cyprosulfonamide, dichlormid, 4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660), 2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), dicyclonon, dietholate, ethyl 1,6-dihydro-1-(2-methoxyphenyl)-6-oxo-2-phenyl-5-pyrimidinecarboxylate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, 2-hydroxy-N,N-dimethyl-6-(trifluoromethyl)pyridine-3-carboxamide, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone ((4-methoxy-3-methylphenyl)(3-methylphenyl)methanone), naphthalic anhydride (1,8-naphthalic anhydride) oxabetrinil 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.
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 another herbicide. Table A1 lists specific combinations of a Component (a) with Component (b) illustrative of the mixtures, compositions and methods of the present invention. Compound 1 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 1 in Index Table A) with 2,4-D is typically applied in a weight ratio between 1:192 to 6:1. The remaining lines of Table A1 are to be construed similarly.











TABLE A1







Typical
More Typical
Most Typical


Component (a)
Component (b)
Weight Ratio
Weight Ratio
Weight Ratio







Compound 129
2,4-D
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 129
4-amino-3-chloro-6-(4-chloro-2-
 1:20 to 56:1
 1:6 to 19:1
 1:2 to 4:1



fluoro-3-methoxyphenyl)-2-



pyridinecarboxylic acid



(halauxifen)


Compound 129
4-amino-3-chloro-6-(4-chloro-2-
 1:20 to 56:1
 1:6 to 19:1
 1:2 to 4:1



fluoro-3-methoxyphenyl)-2-



pyridinecarboxylic acid methyl



ester (halauxifen methyl)


Compound 129
Acetochlor
1:768 to 2:1
1:256 to 1:2 
 1:96 to 1:11


Compound 129
Acifluorfen
 1:96 to 12:1
1:32 to 4:1
1:12 to 1:2


Compound 129
Aclonifen
1:857 to 2:1
1:285 to 1:3 
1:107 to 1:12


Compound 129
Alachlor
1:768 to 2:1
1:256 to 1:2 
 1:96 to 1:11


Compound 129
Ametryn
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Amicarbazone
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 129
Amidosulfuron
  1:6 to 168:1
 1:2 to 56:1
 1:1 to 11:1


Compound 129
Aminocyclopyrachlor
 1:48 to 24:1
1:16 to 8:1
 1:6 to 2:1


Compound 129
Aminopyralid
 1:20 to 56:1
 1:6 to 19:1
 1:2 to 4:1


Compound 129
Amitrole
1:768 to 2:1
1:256 to 1:2 
 1:96 to 1:11


Compound 129
Anilofos
 1:96 to 12:1
1:32 to 4:1
1:12 to 1:2


Compound 129
Asulam
1:960 to 2:1
1:320 to 1:3 
1:120 to 1:14


Compound 129
Atrazine
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 129
Azimsulfuron
  1:6 to 168:1
 1:2 to 56:1
 1:1 to 11:1


Compound 129
Beflubutamid
1:342 to 4:1
1:114 to 2:1 
1:42 to 1:5


Compound 129
Benfuresate
1:617 to 2:1
1:205 to 1:2 
1:77 to 1:9


Compound 129
Bensulfuron-methyl
 1:25 to 45:1
 1:8 to 15:1
 1:3 to 3:1


Compound 129
Bentazone
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 129
Benzobicyclon
 1:85 to 14:1
1:28 to 5:1
1:10 to 1:2


Compound 129
Benzofenap
1:257 to 5:1
1:85 to 2:1
1:32 to 1:4


Compound 129
Bicyclopyrone
 1:42 to 27:1
1:14 to 9:1
 1:5 to 2:1


Compound 129
Bifenox
1:257 to 5:1
1:85 to 2:1
1:32 to 1:4


Compound 129
Bispyribac-sodium
  1:10 to 112:1
 1:3 to 38:1
 1:1 to 7:1


Compound 129
Bromacil
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Bromobutide
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Bromoxynil
 1:96 to 12:1
1:32 to 4:1
1:12 to 1:2


Compound 129
Butachlor
1:768 to 2:1
1:256 to 1:2 
 1:96 to 1:11


Compound 129
Butafenacil
 1:42 to 27:1
1:14 to 9:1
 1:5 to 2:1


Compound 129
Butylate
1:1542 to 1:2 
1:514 to 1:5 
1:192 to 1:22


Compound 129
Carfenstrole
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 129
Carfentrazone-ethyl
1:128 to 9:1
1:42 to 3:1
1:16 to 1:2


Compound 129
Chlorimuron-ethyl
  1:8 to 135:1
 1:2 to 45:1
 1:1 to 9:1


Compound 129
Chlorotoluron
1:768 to 2:1
1:256 to 1:2 
 1:96 to 1:11


Compound 129
Chlorsulfuron
  1:6 to 168:1
 1:2 to 56:1
 1:1 to 11:1


Compound 129
Cincosulfuron
 1:17 to 68:1
 1:5 to 23:1
 1:2 to 5:1


Compound 129
Cinidon-ethyl
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Cinmethylin
 1:34 to 34:1
 1:11 to 12:1
 1:4 to 3:1


Compound 129
Clacyfos
 1:34 to 34:1
 1:11 to 12:1
 1:4 to 3:1


Compound 129
Clethodim
 1:48 to 24:1
1:16 to 8:1
 1:6 to 2:1


Compound 129
Clodinafop-propargyl
 1:20 to 56:1
 1:6 to 19:1
 1:2 to 4:1


Compound 129
Clomazone
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Clomeprop
1:171 to 7:1
1:57 to 3:1
1:21 to 1:3


Compound 129
Clopyralid
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 129
Cloransulam-methyl
 1:12 to 96:1
 1:4 to 32:1
 1:1 to 6:1


Compound 129
Cumyluron
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Cyanazine
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Cyclopyrimorate
 1:17 to 68:1
 1:5 to 23:1
 1:2 to 5:1


Compound 129
Cyclosulfamuron
 1:17 to 68:1
 1:5 to 23:1
 1:2 to 5:1


Compound 129
Cycloxydim
 1:96 to 12:1
1:32 to 4:1
1:12 to 1:2


Compound 129
Cyhalofop
 1:25 to 45:1
 1:8 to 15:1
 1:3 to 3:1


Compound 129
Daimuron
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 129
Desmedipham
1:322 to 4:1
1:107 to 2:1 
1:40 to 1:5


Compound 129
Dicamba
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 129
Dichlobenil
1:1371 to 1:2 
1:457 to 1:4 
1:171 to 1:20


Compound 129
Dichlorprop
1:925 to 2:1
1:308 to 1:3 
1:115 to 1:13


Compound 129
Diclofop-methyl
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Diclosulam
  1:10 to 112:1
 1:3 to 38:1
 1:1 to 7:1


Compound 129
Difenzoquat
1:288 to 4:1
1:96 to 2:1
1:36 to 1:4


Compound 129
Diflufenican
1:857 to 2:1
1:285 to 1:3 
1:107 to 1:12


Compound 129
Diflufenzopyr
 1:12 to 96:1
 1:4 to 32:1
 1:1 to 6:1


Compound 129
Dimethachlor
1:768 to 2:1
1:256 to 1:2 
 1:96 to 1:11


Compound 129
Dimethametryn
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 129
Dimethenamid-P
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Dithiopyr
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 129
Diuron
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
EPTC
1:768 to 2:1
1:256 to 1:2 
 1:96 to 1:11


Compound 129
Esprocarb
1:1371 to 1:2 
1:457 to 1:4 
1:171 to 1:20


Compound 129
Ethalfluralin
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Ethametsulfuron-methyl
 1:17 to 68:1
 1:5 to 23:1
 1:2 to 5:1


Compound 129
Ethoxyfen
  1:8 to 135:1
 1:2 to 45:1
 1:1 to 9:1


Compound 129
Ethoxysulfuron
 1:20 to 56:1
 1:6 to 19:1
 1:2 to 4:1


Compound 129
Etobenzanid
1:257 to 5:1
1:85 to 2:1
1:32 to 1:4


Compound 129
Fenoxaprop-ethyl
 1:120 to 10:1
1:40 to 4:1
1:15 to 1:2


Compound 129
Fenoxasulfone
 1:85 to 14:1
1:28 to 5:1
1:10 to 1:2


Compound 129
Fenquinotrione
 1:17 to 68:1
 1:5 to 23:1
 1:2 to 5:1


Compound 129
Fentrazamide
 1:17 to 68:1
 1:5 to 23:1
 1:2 to 5:1


Compound 129
Flazasulfuron
 1:17 to 68:1
 1:5 to 23:1
 1:2 to 5:1


Compound 129
Florasulam
  1:2 to 420:1
  1:1 to 140:1
 2:1 to 27:1


Compound 129
Fluazifop-butyl
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 129
Flucarbazone
  1:8 to 135:1
 1:2 to 45:1
 1:1 to 9:1


Compound 129
Flucetosulfuron
  1:8 to 135:1
 1:2 to 45:1
 1:1 to 9:1


Compound 129
Flufenacet
1:257 to 5:1
1:85 to 2:1
1:32 to 1:4


Compound 129
Flumetsulam
 1:24 to 48:1
 1:8 to 16:1
 1:3 to 3:1


Compound 129
Flumiclorac-pentyl
  1:10 to 112:1
 1:3 to 38:1
 1:1 to 7:1


Compound 129
Flumioxazin
 1:25 to 45:1
 1:8 to 15:1
 1:3 to 3:1


Compound 129
Fluometuron
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Flupyrsulfuron-methyl
  1:3 to 336:1
  1:1 to 112:1
 2:1 to 21:1


Compound 129
Fluridone
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Fluroxypyr
 1:96 to 12:1
1:32 to 4:1
1:12 to 1:2


Compound 129
Flurtamone
1:857 to 2:1
1:285 to 1:3 
1:107 to 1:12


Compound 129
Fluthiacet-methyl
 1:48 to 42:1
 1:16 to 14:1
 1:3 to 3:1


Compound 129
Fomesafen
 1:96 to 12:1
1:32 to 4:1
1:12 to 1:2


Compound 129
Foramsulfuron
 1:13 to 84:1
 1:4 to 28:1
 1:1 to 6:1


Compound 129
Glufosinate
1:288 to 4:1
1:96 to 2:1
1:36 to 1:4


Compound 129
Glyphosate
1:288 to 4:1
1:96 to 2:1
1:36 to 1:4


Compound 129
Halosulfuron-methyl
 1:17 to 68:1
 1:5 to 23:1
 1:2 to 5:1


Compound 129
Haloxyfop-methyl
 1:34 to 34:1
 1:11 to 12:1
 1:4 to 3:1


Compound 129
Hexazinone
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 129
Imazamox
 1:13 to 84:1
 1:4 to 28:1
 1:1 to 6:1


Compound 129
Imazapic
 1:20 to 56:1
 1:6 to 19:1
 1:2 to 4:1


Compound 129
Imazapyr
 1:85 to 14:1
1:28 to 5:1
1:10 to 1:2


Compound 129
Imazaquin
 1:34 to 34:1
 1:11 to 12:1
 1:4 to 3:1


Compound 129
Imazethabenz-methyl
1:171 to 7:1
1:57 to 3:1
1:21 to 1:3


Compound 129
Imazethapyr
 1:24 to 48:1
 1:8 to 16:1
 1:3 to 3:1


Compound 129
Imazosulfuron
 1:27 to 42:1
 1:9 to 14:1
 1:3 to 3:1


Compound 129
Indanofan
1:342 to 4:1
1:114 to 2:1 
1:42 to 1:5


Compound 129
Indaziflam
 1:25 to 45:1
 1:8 to 15:1
 1:3 to 3:1


Compound 129
Iodosulfuron-methyl
  1:3 to 336:1
  1:1 to 112:1
 2:1 to 21:1


Compound 129
Ioxynil
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 129
Ipfencarbazone
 1:85 to 14:1
1:28 to 5:1
1:10 to 1:2


Compound 129
Isoproturon
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Isoxaben
1:288 to 4:1
1:96 to 2:1
1:36 to 1:4


Compound 129
Isoxaflutole
 1:60 to 20:1
1:20 to 7:1
 1:7 to 2:1


Compound 129
Lactofen
 1:42 to 27:1
1:14 to 9:1
 1:5 to 2:1


Compound 129
Lenacil
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Linuron
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
MCPA
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 129
MCPB
1:288 to 4:1
1:96 to 2:1
1:36 to 1:4


Compound 129
Mecoprop
1:768 to 2:1
1:256 to 1:2 
 1:96 to 1:11


Compound 129
Mefenacet
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Mefluidide
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 129
Mesosulfuron-methyl
  1:5 to 224:1
 1:1 to 75:1
 1:1 to 14:1


Compound 129
Mesotrione
 1:42 to 27:1
1:14 to 9:1
 1:5 to 2:1


Compound 129
Metamifop
 1:42 to 27:1
1:14 to 9:1
 1:5 to 2:1


Compound 129
Metazachlor
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Metazosulfuron
 1:25 to 45:1
 1:8 to 15:1
 1:3 to 3:1


Compound 129
Methabenzthiazuron
1:768 to 2:1
1:256 to 1:2 
 1:96 to 1:11


Compound 129
Metolachlor
1:768 to 2:1
1:256 to 1:2 
 1:96 to 1:11


Compound 129
Metosulam
  1:8 to 135:1
 1:2 to 45:1
 1:1 to 9:1


Compound 129
Metribuzin
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 129
Metsulfuron-methyl
  1:2 to 560:1
  1:1 to 187:1
 3:1 to 35:1


Compound 129
Molinate
1:1028 to 2:1 
1:342 to 1:3 
1:128 to 1:15


Compound 129
Napropamide
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Naptalam
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 129
Nicosulfuron
 1:12 to 96:1
 1:4 to 32:1
 1:1 to 6:1


Compound 129
Norflurazon
1:1152 to 1:1 
1:384 to 1:3 
1:144 to 1:16


Compound 129
Orbencarb
1:1371 to 1:2 
1:457 to 1:4 
1:171 to 1:20


Compound 129
Orthosulfamuron
 1:20 to 56:1
 1:6 to 19:1
 1:2 to 4:1


Compound 129
Oryzalin
1:514 to 3:1
1:171 to 1:2 
1:64 to 1:8


Compound 129
Oxadiargyl
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Oxadiazon
1:548 to 3:1
1:182 to 1:2 
1:68 to 1:8


Compound 129
Oxasulfuron
 1:27 to 42:1
 1:9 to 14:1
 1:3 to 3:1


Compound 129
Oxaziclomefone
 1:42 to 27:1
1:14 to 9:1
 1:5 to 2:1


Compound 129
Oxyfluorfen
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Paraquat
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 129
Pendimethalin
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Penoxsulam
  1:10 to 112:1
 1:3 to 38:1
 1:1 to 7:1


Compound 129
Penthoxamid
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Pentoxazone
 1:102 to 12:1
1:34 to 4:1
1:12 to 1:2


Compound 129
Phenmedipham
 1:102 to 12:1
1:34 to 4:1
1:12 to 1:2


Compound 129
Picloram
 1:96 to 12:1
1:32 to 4:1
1:12 to 1:2


Compound 129
Picolinafen
 1:34 to 34:1
 1:11 to 12:1
 1:4 to 3:1


Compound 129
Pinoxaden
 1:25 to 45:1
 1:8 to 15:1
 1:3 to 3:1


Compound 129
Pretilachlor
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 129
Primisulfuron-methyl
  1:8 to 135:1
 1:2 to 45:1
 1:1 to 9:1


Compound 129
Prodiamine
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Profoxydim
 1:42 to 27:1
1:14 to 9:1
 1:5 to 2:1


Compound 129
Prometryn
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Propachlor
1:1152 to 1:1 
1:384 to 1:3 
1:144 to 1:16


Compound 129
Propanil
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Propaquizafop
 1:48 to 24:1
1:16 to 8:1
 1:6 to 2:1


Compound 129
Propoxycarbazone
 1:17 to 68:1
 1:5 to 23:1
 1:2 to 5:1


Compound 129
Propyrisulfuron
 1:17 to 68:1
 1:5 to 23:1
 1:2 to 5:1


Compound 129
Propyzamide
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Prosulfocarb
1:1200 to 1:2 
1:400 to 1:4 
1:150 to 1:17


Compound 129
Prosulfuron
  1:6 to 168:1
 1:2 to 56:1
 1:1 to 11:1


Compound 129
Pyraclonil
 1:42 to 27:1
1:14 to 9:1
 1:5 to 2:1


Compound 129
Pyraflufen-ethyl
  1:5 to 224:1
 1:1 to 75:1
 1:1 to 14:1


Compound 129
Pyrasulfotole
 1:13 to 84:1
 1:4 to 28:1
 1:1 to 6:1


Compound 129
Pyrazolynate
1:857 to 2:1
1:285 to 1:3 
1:107 to 1:12


Compound 129
Pyrazosulfuron-ethyl
  1:10 to 112:1
 1:3 to 38:1
 1:1 to 7:1


Compound 129
Pyrazoxyfen
  1:5 to 224:1
 1:1 to 75:1
 1:1 to 14:1


Compound 129
Pyribenzoxim
  1:10 to 112:1
 1:3 to 38:1
 1:1 to 7:1


Compound 129
Pyributicarb
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Pyridate
1:288 to 4:1
1:96 to 2:1
1:36 to 1:4


Compound 129
Pyriftalid
  1:10 to 112:1
 1:3 to 38:1
 1:1 to 7:1


Compound 129
Pyriminobac-methyl
 1:20 to 56:1
 1:6 to 19:1
 1:2 to 4:1


Compound 129
Pyrimisulfan
 1:17 to 68:1
 1:5 to 23:1
 1:2 to 5:1


Compound 129
Pyrithiobac
 1:24 to 48:1
 1:8 to 16:1
 1:3 to 3:1


Compound 129
Pyroxasulfone
 1:85 to 14:1
1:28 to 5:1
1:10 to 1:2


Compound 129
Pyroxsulam
  1:5 to 224:1
 1:1 to 75:1
 1:1 to 14:1


Compound 129
Quinclorac
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 129
Quizalofop-ethyl
 1:42 to 27:1
1:14 to 9:1
 1:5 to 2:1


Compound 129
Rimsulfuron
 1:13 to 84:1
 1:4 to 28:1
 1:1 to 6:1


Compound 129
Saflufenacil
 1:25 to 45:1
 1:8 to 15:1
 1:3 to 3:1


Compound 129
Sethoxydim
 1:96 to 12:1
1:32 to 4:1
1:12 to 1:2


Compound 129
Simazine
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Sulcotrione
 1:120 to 10:1
1:40 to 4:1
1:15 to 1:2


Compound 129
Sulfentrazone
1:147 to 8:1
1:49 to 3:1
1:18 to 1:3


Compound 129
Sulfometuron-methyl
 1:34 to 34:1
 1:11 to 12:1
 1:4 to 3:1


Compound 129
Sulfosulfuron
  1:8 to 135:1
 1:2 to 45:1
 1:1 to 9:1


Compound 129
Tebuthiuron
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Tefuryltrione
 1:42 to 27:1
1:14 to 9:1
 1:5 to 2:1


Compound 129
Tembotrione
 1:31 to 37:1
 1:10 to 13:1
 1:3 to 3:1


Compound 129
Tepraloxydim
 1:25 to 45:1
 1:8 to 15:1
 1:3 to 3:1


Compound 129
Terbacil
1:288 to 4:1
1:96 to 2:1
1:36 to 1:4


Compound 129
Terbuthylatrazine
1:857 to 2:1
1:285 to 1:3 
1:107 to 1:12


Compound 129
Terbutryn
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 129
Thenylchlor
 1:85 to 14:1
1:28 to 5:1
1:10 to 1:2


Compound 129
Thiazopyr
1:384 to 3:1
1:128 to 1:1 
1:48 to 1:6


Compound 129
Thiencarbazone
  1:3 to 336:1
  1:1 to 112:1
 2:1 to 21:1


Compound 129
Thifensulfuron-methyl
  1:5 to 224:1
 1:1 to 75:1
 1:1 to 14:1


Compound 129
Tiafenacil
 1:17 to 68:1
 1:5 to 23:1
 1:2 to 5:1


Compound 129
Thiobencarb
1:768 to 2:1
1:256 to 1:2 
 1:96 to 1:11


Compound 129
Topramazone
  1:6 to 168:1
 1:2 to 56:1
 1:1 to 11:1


Compound 129
Tralkoxydim
 1:68 to 17:1
1:22 to 6:1
 1:8 to 2:1


Compound 129
Triallate
1:768 to 2:1
1:256 to 1:2 
 1:96 to 1:11


Compound 129
Triasulfuron
  1:5 to 224:1
 1:1 to 75:1
 1:1 to 14:1


Compound 129
Triaziflam
1:171 to 7:1
1:57 to 3:1
1:21 to 1:3


Compound 129
Tribenuron-methyl
  1:3 to 336:1
  1:1 to 112:1
 2:1 to 21:1


Compound 129
Triclopyr
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 129
Trifloxysulfuron
  1:2 to 420:1
  1:1 to 140:1
 2:1 to 27:1


Compound 129
Trifluralin
1:288 to 4:1
1:96 to 2:1
1:36 to 1:4


Compound 129
Triflusulfuron-methyl
 1:17 to 68:1
 1:5 to 23:1
 1:2 to 5:1


Compound 129
Tritosulfuron
 1:13 to 84:1
 1:4 to 28:1
 1:1 to 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 2” (i.e. Compound 2 identified in Index Table A), and the first line below the column headings in Table A2 specifically discloses a mixture of Compound 2 with 2,4-D. Tables A3 and A4 are constructed similarly.














Table
Component (a)



Number
Column Entries









A2
Compound 14



A3
Compound 15



A4
Compound 16



A5
Compound 47



A6
Compound 129



A7
Compound 164



A8
Compound 196










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 glyphosate, chlorimuron-ethyl, nicosulfuron, mesotrione, thifensulfuron-methyl, flupyrsulfuron-methyl, tribenuron, pyroxasulfone. pinoxaden, tembotrione, florasulam, pyroxsulam, metolachlor and S-metolachlor.
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-B for compound descriptions. The following abbreviations are used in the Index Tables which follow: t is tertiary, s is secondary, n is normal, i is iso, c is cyclo, Pr is propyl, Bu is butyl, c-Pr is cyclopropyl, t-Bu is tert-butyl, Ph is phenyl, thiene means thiophene, 4-pyridinyl(2-CF3) corresponds to structure J-2A, and —NO2 is nitro. The abbreviation “Ex.” stands for “Example” and is followed by a number indicating in which example the compound is prepared.












INDEX TABLE A





Compd.




M.P. (° C.) or


No.
R1
A
Q
J
M.S. (AP+)







 1 (Ex. 3)
CH3
phenyl(4-CF3)
O
3-thienyl(5-CF3)
    392 # **


2
CH3
phenyl(4-F)
CH2
1H-pyrazol-1-yl(3-
40-42






CF3)


3
CH3
4-pyridinyl(2-F)
C═O
phenyl(3-CF3)
351


4
CH3
4-pyridinyl(2-Cl)
C═O
phenyl(3-CF3)
367


5
CH3
phenyl(2-Cl)
C═O
phenyl(3-CF3)
366


6
CH3
phenyl(2-SCH3)
C═O
phenyl(3-CF3)
378


7
CH3
2-pyridinyl(5-CF3)
CH2
1H-pyrazol-1-yl(3-
377






CF3)


8
CH3
2-pyridinyl(5-CF3)
CH2
1H-1,2,4-triazol-1-
378






yl(3-CF3)


9
CH3
phenyl(4-CF3)
CH2
1H-imidazol-1-yl(2-
119-121






Cl,4-CF3)


10
CH2CH3
phenyl(4-F)
CH2
1H-pyrazol-1-yl(3-
*






CF2CF3)


11
CH3
phenyl(4-CF3)
CH2
1H-imidazol-1-yl(2,5-
118-120






di-Cl,4-CF3)


12
CH3
phenyl(4-CF3)
CH2
1H-pyrazol-1-yl(3-
54-57






CF2CF3)


13
CH3
phenyl(4-CF3)
CH2
1H-imidazol-1-yl(5-
124-126






Cl,4-CF3)


14
OCH2CF3
phenyl(4-CF3)
CH2
4-pyridinyl(2-CF3)
471


 15 (Ex. 1)
OCH3
pheny(4-CF3)
CH2
4-pyridinyl(2-CF3)
  403 **


16
CH3
phenyl(4-F)
CH2
4-pyridinyl(2-CF3)
337


 17 (Ex. 2)
OCH3
phenyl(4-CF3)
CH2
1H-pyrazol-1-yl(3-
  392 **


18
OCH3
phenyl(4-CF3)
CH2
1H-1,2,4-triazol-1-
393






yl(3-CF3)


19
OCH3
phenyl(4-CF3)
CH2
1H-imidazol-1-yl(3-
392






CF3)


20
CH3
phenyl(4-F)
CH2
1H-imidazol-1-yl(2,5-
126-128






di-Cl,4-CF3)


21
CH3
2-pyridinyl(5-CF3)
CH2
1H-pyrazol-1-yl(3-
391






CF3,5-CH3)


22
CH3
4-pyridinyl
C═O
phenyl(3-CF3)
333


23
CH3
2-pyridinyl(5-CF3)
O
4-pyridinyl(2-CF3)
**


24
OCH3
phenyl(4-F)
C═O
4-pyridinyl(2-CF3)
367


25
OCHF2
phenyl(4-F)
CH2
4-pyridinyl(2-CF3)
389


26
OCHF2
phenyl(4-CF3)
CH2
4-pyridinyl(2-CF3)
439


27
SCH3
phenyl(4-F)
CH2
4-pyridinyl(2-CF3)
369


28
Cl
phenyl(4-CF3)
CH2
4-pyridinyl(2-CF3)
407


29
OCH3
phenyl(4-CF3)
CH2
phenyl(3-CF3)
402


30
OCH3
phenyl(4-CF3)
CH2
1H-pyrazol-1-yl(3,5-
*






di-CF3)


31
CH3
phenyl(4-CF3)
CH2
4-pyridinyl(2-OCH3)
*


32
CH3
phenyl(4-CF3)
CH2
1H-pyrazol-1-yl(4-
*






CF3)


33
CH3
phenyl(4-F)
CH2
4-pyridinyl(2-
367






OCH2CF3)


34
OCH3
phenyl(4-F)
O
4-pyridinyl(2-CF3)
355


35
CH3
phenyl(4-F)
CH2
1H-imidazol-1-yl(2-
124-126






Cl,4-CF3)


36
CH3
phenyl(4-F)
CH2
1H-imidazol-1-yl(5-
93-95






Cl,4-CF3)


37
CH3
phenyl(4-CF3)
O
3-pyridinyl(5-CF3)
389


38
CH3
phenyl(3-CF3)
O
4-pyrimidinyl(6-CF3)
390


39
CH3
2-pyridinyl(5-F)
C═O
phenyl(3-CF3)
321


40
CH3
phenyl(3-CF3)
O
4-pyridinyl(2-CF3)
389


41
CH3
phenyl(4-NO2)
C═O
phenyl(3-CF3)
*


42
CH3
phenyl(4-Cl)
C═O
phenyl(3-CF3)
*


43
CH3
phenyl
C═O
phenyl(3-CF3)
332


44
CH3
phenyl(4-CH3)
C═O
phenyl(3-CF3)
346


45
CH3
phenyl(4-CF3)
C═O
phenyl(3-CF3)
*


47
CH3
phenyl(4-CF3)
CH2
4-pyridinyl(2-CF3)
387


48
CH3
phenyl(4-CF3)
O
4-pyridinyl(2-OCHF2)
387


49
CH3
4-pyridinyl(2-CF3)
C═O
phenyl(3-CF3)
401


50
CH3
5-pyrazinyl(2-Cl)
C═O
phenyl(3-CF3)
368


51
CH3
phenyl(4-CF3)
CH2
1H-pyrazol-4-yl(1-
390






CH2CF3)


52
CH3
phenyl(4-Cl)
O
4-pyridinyl(2-CF3)
355


53
CH3
phenyl(4-Br)
O
4-pyridinyl(2-CF3)
400


 54 (Ex. 10)
CH3
phenyl(2,4-di-F)
CH2
4-pyridinyl(2-CF3)
  355 **


55
CH3
phenyl(3,4-di-F)
CH2
4-pyridinyl(2-CF3)
355


56
CH3
phenyl(4-F)
O
phenyl(4-F,3-CF3)
356


57
CH3
2-pyridinyl(6-CF3)
C═O
phenyl(3-CF3)
400


58
CH3
3-pyridazinyl(6-
C═O
phenyl(CF3)
*




CF3)


59
CH3
1H-1,2,4-thiadiazol-
C═O
phenyl(3-CF3)
374




5-yl(3-Cl)


60
CH3
2-pyridinyl
C═O
phenyl(3-CF3)
333


61
CH3
phenyl(4-I)
C═O
phenyl(3-CF3)
*


62
CH3
phenyl(3-NO2)
C═O
phenyl(3-CF3)


63
CH3
phenyl(2-NO2)
C═O
phenyl(3-CF3)


64
CH3
phenyl(3-CF3)
O
1H-pyrazol-5-yl(3-
392






CF3,1-CH3)


65
CH3
phenyl(2-Cl,4-F)
CH2
4-pyridinyl(2-CF3)
371


66
CH3
3-pyridinyl(5-CF3)
C═O
phenyl(3-CF3)
401


68
CH3
2-pyridinyl(5-CHF2)
C═O
phenyl(3-CF3)
383


69
CH3
phenyl(4-CF3)
NH
phenyl(3-CF3)
101-104


70
CH3
phenyl(3-CF3)
O
phenyl(3-CF3)
388


71
CH3
phenyl(4-F)
O
4-pyridinyl(2-
369






OCH2CF3)


72
CH3
3-pyridinyl(6-Cl)
C═O
phenyl(3-CF3)
367


73
CH3
3-pyridinyl(6-CF3)
C═O
phenyl(3-CF3)
401


74
CH3
phenyl(4-CF3)
O
1H-pyrazol-4-yl(1-
392






CH2CF3)


75
OCH3
phenyl(4-CF3)
C═O
4-pyridinyl(2-CF3)
417


76
CH3
phenyl(3-Cl)
C═O
phenyl(3-CF3)
*


77
CH3
phenyl(4-CF3)
O
4-pyridinyl(2-
419






OCH2CF3)


78
OCH3
phenyl(4-CF3)
CH(OH)
4-pyridinyl(2-CF3)
*


79
OCH3
phenyl(4-CF3)
CCH3(OH)
4-pyridinyl(2-CF3)
*


80
OCH3
phenyl(4-CF3)
CHF
4-pyridinyl(2-CF3)
421


82
CH3
phenyl(4-CF3)
O
phenyl(2-Cl)
354


83
CH3
phenyl(4-CF3)
O
phenyl(4-CF3)
69-71


84
CH3
phenyl(4-CF3)
O
phenyl(3-Cl)
73-75


86
CH3
phenyl(4-F)
O
phenyl(4-F,3-CH3)
302


87
CH3
phenyl(4-F)
O
4-pyridinyl(3-CH3)
285


88
CH3
phenyl(4-CF3)
S
phenyl(3-CF3)
404


90
CH3
phenyl(3-I)
C═O
phenyl(3-CF3)
*


91
CH3
phenyl(2-I)
C═O
phenyl(3-CF3)
*


92
CH3
phenyl(4-Br)
C═O
phenyl(3-CF3)
*


93
CH3
phenyl(4-SCH3)
C═O
phenyl(3-CF3)
378


94
CH3
phenyl(4-F)
CH2
1H-1,2,4-triazol-1-
327






yl(3-CF3)


95
CH3
phenyl(4-F)
CH2
1H-pyrazol-1-yl(3-
83-85






CF3)


96
CH3
phenyl(4-CF3)
CH2
1H-imidazol-1-yl(4-
106-109






CF3)


97
CH3
phenyl(4-F)
CH2
1H-pyrazol-1-yl(3-
91-93






CF3,5-CH3)


98
CH3
phenyl(4-F)
O
phenyl(3-CF3)
*


99
CH3
phenyl(4-F)
O
phenyl(4-Cl,3-CF3)
*


100
CH3
phenyl(4-F)
O
phenyl(3-OCF3)
*


101
CH3
phenyl(4-F)
O
4-pyrimidinyl(2-CF3)
*


102
CH3
phenyl(4-F)
O
2-pyrimidinyl(4-CF3)
*


103
CH3
phenyl(4-CF3)
O
phenyl(4-Cl,3-CF3)
*


104
CH3
phenyl(4-CF3)
O
1H-pyrazol-5-yl(1-
*






CH3,3-CF3)


105
Br
2-pyridinyl(5-CF3)
CH2
phenyl(3-CF3)
453


106
CH3
2-pyridinyl(5-CF3)
CH2
phenyl(3-CF3)
387


107
CH3
2-pyridinyl(5-CF3)
C═O
phenyl(3-CF3)
401


108
CH2CH3
2-pyridinyl(5-CF3)
CH2
phenyl(3-CF3)
*


109
CH3
2-pyridinyl(5-CF3)
O
phenyl(3-CF3)
389


110
CH2OH
phenyl(4-CF3)
O
phenyl(3-CF3)
*


111
CH3
phenyl(4-CF3)
O
phenyl(3-CF3)
*


112
CH3
phenyl(4-F)
CH2
1H-imidazol-1-yl(4-
76-79






CF3)


113
CH2CH3
phenyl(4-CF3)
O
phenyl(3-CF3)
*


114 (Ex. 5)
CH2OH
phenyl(4-CF3)
O
phenyl(3-OCF3)
**


115 (Ex. 7)
CH2OCH3
phenyl(4-CF3)
O
phenyl(3-OCF3)
**


116 (Ex. 8)
CH2F
phenyl(4-CF3)
O
phenyl(3-OCF3)
**


117
CH3
phenyl(4-CF3)
CH2
1H-pyrazol-1-yl(3-
60-63






CF3)


118
CH2CH3
phenyl(4-CF3)
CH2
1H-pyrazol-1-yl(3-
390






CF3)


119 (Ex. 6)
CH3
phenyl(4-CF3)
O
phenyl(3-OCF3)
**


120
CH3
phenyl(4-CF3)
O
4-pyridinyl(2-CF3)
78.3-78.8


121
CH2CH3
phenyl(4-CF3)
CH2
1H-imidazol-1-yl(5-
 98-100






Cl,4-CF3)


122
CH2CH3
phenyl(4-CF3)
CH2
1H-imidazol-1-yl(2-
82-84






Cl,4-CF3)


123
Br
phenyl(4-CF3)
CH2
phenyl(3-CF3)
*


124
CH3
phenyl(4-CF3)
CH2
phenyl(3-CF3)
*


125 (Ex. 9)
CH2CH3
phenyl(4-CF3)
O
phenyl(3-OCF3)
**


126
CH3
phenyl(4-F)
O
1H-pyrazol-5-yl(3-
342






CF3,1-CH3)


127
CH3
phenyl(4-F)
O
2-pyridinyl(6-CF3)
*


128
CH3
phenyl(4-F)
O
2-pyridinyl(4-CF3)
*


129 (Ex. 4)
CH3
phenyl(4-F)
O
4-pyridinyl(2-CF3)
43.5-44.1


130
CH2CH3
phenyl(4-CF3)
CH2
1H-1,2,4-triazol-1-
391






yl(3-CF3)


131
CH2CH3
phenyl(4-CF3)
CH2
1H-pyrazol-1-yl(3-
74-76






CF3,5-CH3)


132
CH3
phenyl(4-CF3)
CH2
1H-1,2,4-triazol-1-
377






yl(3-CF3)


133
CH2CH3
phenyl(4-CF3)
CH2
1H-imidazol-1-yl(4-
84-86






CF3)


134
CH3
phenyl(4-CF3)
CH2
1H-pyrazol-1-yl(3-
101-103






CF3,5-CH3)


135
CH3
phenyl(4-F)
O
4-pyridinyl(2-CH3)
285


136
CH3
phenyl(3,4-di-F)
CH2
4-pyridinyl(2-CHF2)
337, 335 #


137
CH3
4-pyridinyl(2-CF3)
CH2
4-pyridinyl(2-CF3)
  386 #


138
OCH3
phenyl(4-CF3)
CH2
4-pyridinyl(2-CHF2)
385, 383 #


139
OCH3
phenyl(5-F)
CH2
4-pyridinyl(2-CF3)
353


140
CH3
4-pyridinyl(2-CF3)
C═N—OMe
phenyl(3-CF3)
430


141
CH3
4-pyridinyl(2-Cl)
CH2
4-pyridinyl(2-CF3)
354, 352 #


142
OCH2CF3
phenyl(4-F)
CH2
4-pyridinyl(2-CF3)
421


143
CH2CH3
phenyl(3-CF3)
CH2
phenyl(3-CF3)
44-46


144
CH2CH3
phenyl(4-F)
CH2
phenyl(3-CF3)
45-47


145
CH3
phenyl(3,4-di-F)
O
4-pyridinyl(2-CF3)
357


146
CH3
phenyl(2,4-di-F)
O
4-pyridinyl(2-CF3)
357


147
CH3
phenyl(4-F,3-CF3)
O
4-pyridinyl(2-CF3)
407


148
CH3
phenyl(3-F,4-CF3)
O
4-pyridinyl(2-CF3)
407


149
n-Pr
phenyl(4-F)
CH2
phenyl(3-CF3)
59-62


150
CH(CH3)2
phenyl(4-F)
CH2
phenyl(3-CF3)
364


151
CH(CH3)2
phenyl(4-F)
CH2
4-pyridinyl(2-CF3)
365


152
OCH3
phenyl(4-F)
CH(CH3)
4-pyridinyl(2-CF3)
418


153
n-Pr
phenyl(4-F)
CH2
4-pyridinyl(2-CF3)
365


154
CH2CH3
phenyl(4-F)
CH2
4-pyridinyl(2-CF3)
351


155
CH2CH3
phenyl(4-CF3)
CH2
4-pyridinyl(2-CF3)
401


156
CH3
phenyl(4-F,3-CF3)
CH2
4-pyridinyl(2-CF3)
405


157
CH3
phenyl(4-F)
CH2
phenyl(3-CF3)
336


158
F
phenyl(4-F)
C═O
4-pyridinyl(2-CF3)
*


159
F
phenyl(4-F)
CH2
4-pyridinyl(2-CF3)
*


160
CH2F
phenyl(4-F)
O
4-pyridinyl(2-CF3)
*


161
CH2OCH3
phenyl(4-F)
O
4-pyridinyl(2-CF3)
*


162
CH3
phenyl(3-F,4-CF3)
CH2
4-pyridinyl(2-CF3)
405


163
CH2OCH2CH3
phenyl(4-F)
O
4-pyridinyl(2-CF3)
*


164
OCH2CH3
phenyl(3-CF3)
CH2
4-pyridinyl(2-CF3)
*


165
OCH3
phenyl(2,4-di-F)
CH2
4-pyridinyl(2-CF3)
371


166
CH2CH3
phenyl(4-F)
O
4-pyridinyl(2-CF3)
*


167
CH3
phenyl(4-F)
C═O
4-pyridinyl(2-CF3)
*


168
n-Pr
phenyl(4-F)
O
4-pyridinyl(2-CF3)
*


169
CH2CH3
phenyl(4-CF3)
O
4-pyridinyl(2-CF3)
*


170
n-Pr
phenyl(4-CF3)
O
4-pyridinyl(2-CF3)
417


171
CH2CH3
phenyl(3,4-di-F)
O
4-pyridinyl(2-CF3)
371


172
n-Pr
phenyl(3,4-di-F)
O
4-pyridinyl(2-CF3)
385


173
CH2CH3
phenyl(3,4-di-F)
O
4-pyridinyl(2-CH2F)
353


174
n-Pr
phenyl(3,4-di-F)
O
4-pyridinyl(2-CH2F)
367


175
t-Bu
phenyl(4-F)
C═O
4-pyridinyl(2-CF3)
*


176
t-Bu
phenyl(4-F)
CH2
4-pyridinyl(2-CF3)
*


177
OCH2CH3
phenyl(4-F)
C═O
4-pyridinyl(2-CF3)
*


178
CH2CH3
phenyl(2,4-di-F)
O
4-pyridinyl(2-CF3)
371


179
n-Pr
phenyl(2,4-di-F)
O
4-pyridinyl(2-CF3)
385


180
CH2CH3
phenyl(4-F,3-CF3)
O
4-pyridinyl(2-CF3)
421


181
CH2CH3
phenyl(2,4-di-F)
O
4-pyridinyl(2-CHF2)
353


182
n-Pr
phenyl
O
4-pyridinyl(2-CHF2)
367


183
CH2CH3
phenyl(3-F,4-CF3)
O
4-pyridinyl(2-CF3)
421


184
n-Bu
phenyl(4-CF3)
O
4-pyridinyl(2-CF3)
*


185
n-Pr
phenyl(3-F,4-CF3)
O
4-pyridinyl(2-CF3)
*


186
CH2CH(CH3)2
phenyl(4-CF3)
O
4-pyridinyl(2-CF3)
431


187
CH2CH(CH3)2
phenyl(4-CF3)
O
4-pyridinyl(2-CHF2)
413


188
OCH2CH3
phenyl(4-Cl)
CH2
4-pyridinyl(2-CF3)
*


189
OCH2CH3
phenyl(4-Br)
CH2
4-pyridinyl(2-CF3)
*


190
OCH2CH3
phenyl(2,4-di-F)
CH2
4-pyridinyl(2-CF3)
*


191
O-n-Pr
phenyl(4-CF3)
CH2
4-pyridinyl(2-CF3)
*


192
OCH(CH3)2
phenyl(4-CF3)
CH2
4-pyridinyl(2-CF3)
*


193
OCH2CH(CH3)2
phenyl(4-CF3)
CH2
4-pyridinyl(2-CF3)
*


194
O-n-Bu
phenyl(4-CF3)
CH2
4-pyridinyl(2-CF3)
*


195
OCH2CH3
phenyl(4-F)
CH2
4-pyridinyl(2-CHF2)
*


 196 (Ex. 11)
OCH2CH3
phenyl(4-F)
CH2
4-pyridinyl(2-CF3)
59-60


197
OC(═O)CH3
phenyl(4-CF3)
CH2
4-pyridinyl(2-CF3)
*


198
OH
phenyl(4-CF3)
CH2
4-pyridinyl(2-CF3)
389


199
c-Pr
phenyl(3-CF3)
O
4-pyridinyl(2-CF3)
397


200
c-Pr
phenyl(3-CF3)
O
4-pyridinyl(2-CF3)
415


201
CH3
2-pyridinyl(5-CF3)
C═N—OH
phenyl(3-CF3)
416





* See Index Table B for 1H NMR data.


** See Synthesis Example for 1H NMR data.


# reported as AP−.














INDEX TABLE B





Compd.



No.
1H NMR dataa
















10
1.21 (t, 3H), 2.70 (q, 2H), 5.53 (s, 2H), 6.55 (d, 1H), 7.55 (t, 1H), 7.73 (d, 2H), 8.15 (d, 2H)


23
2.42 (s, 3H), 7.39 (m, 1H), 7.57 (m, 1H), 8.06 (m, 1H), 8.13 (m, 1H), 8.69 (m, 1H), 8.84 (s, 1H)


30
4.04 (s, 3H), 5.55 (s, 2H), 6.93 (s, 1H), 7.66-7.71 (m, 2H), 8.00-8.04 (m, 2H)


31
2.26 (s, 3H), 3.92 (s, 3H), 4.02 (s, 2H), 6.58-6.61 (m, 1H), 6.75-6.79 (m, 1H), 7.69-7.73 (m, 2H),



8.07-8.14 (m, 3H)


32
2.36 (s, 3H), 5.46 (s, 2H), 7.72-7.75 (m, 3H), 7.77 (s, 1H), 8.12-8.16 (m, 2H)


41
2.73 (s, 3H), 7.67-7.73 (m, 1H), 7.89-7.93 (m, 1H), 8.25-8.30 (m, 2H), 8.37-8.42 (m, 2H),



8.46-8.50 (m, 1H), 8.60-8.63 (m, 1H)


42
2.71 (s, 3H), 7.47-7.51 (m, 2H), 7.65-7.70 (m, 1H), 7.86-7.91 (m, 1H), 8.03-8.07 (m, 2H),



8.46-8.50 (m, 1H), 8.61-8.64 (m, 1H)


45
2.73 (s, 3H), 7.66-7.72 (m, 1H), 7.77-7.82 (m, 2H), 7.88-7.92 (m, 1H), 8.22-8.26 (m, 2H),



8.47-8.50 (m, 1H), 8.63-8.65 (m, 1H)


58
2.80 (s, 3H), 7.68-7.73 (m, 1H), 7.89-7.93 (m, 1H), 8.04-8.08 (m, 1H), 8.42-8.45 (m, 1H),



8.55-8.59 (m, 2H)


61
2.71 (s, 3H), 7.64-7.69 (m, 1H), 7.82-7.90 (m, 5H), 8.45-8.49 (m, 1H), 8.61-8.64 (m, 1H)


62
2.74 (s, 3H), 7.68-7.75 (m, 2H), 7.89-7.93 (m, 1H), 8.25-8.29 (m, 1H), 8.42-8.51 (m, 2H),



8.61-8.64 (m, 1H), 8.96-8.98 (m, 1H)


63
2.71 (s, 3H), 7.58-7.69 (m, 2H), 7.72-7.77 (m, 1H), 7.83-7.90 (m, 2H), 7.95-7.99 (m, 1H),



8.37-8.41 (m, 1H), 8.45-8.48 (m, 1H)


76
2.71 (s, 3H), 7.36-7.47 (m, 2H), 7.66-7.71 (m, 1H), 7.86-7.91 (m, 1H), 7.97-8.01 (m, 1H),



8.12-8.16 (m, 1H), 8.47-8.51 (m, 1H), 8.61-8.63 (m, 1H)


78
2.89-2.91 (m, 1H), 4.07 (s, 3H), 6.07-6.10 (m, 1H), 7.60-7.63 (m, 1H), 7.68-7.72 (m, 2H),



7.85-7.87 (m, 1H), 8.00-8.04 (m, 2H), 8.72-8.75 (m, 1H)


79
1.54 (s, 3H), 3.38 (s, 1H), 4.05 (s, 3H), 7.58-7.62 (m, 1H), 7.69-7.73 (m, 2H), 7.87-7.89 (m, 1H),



8.02-8.06 (m, 2H), 8.68-8.70 (m, 1H)


90
2.71 (s, 3H), 7.22-7.27 (m, 1H), 7.66-7.77 (m, 2H), 7.88-7.91 (m, 1H), 8.05-8.09 (m, 1H),



8.46-8.50 (m, 2H), 8.61-8.64 (m, 1H)


91
2.74 (s, 3H), 7.21-7.26 (m, 1H), 7.48-7.67 (m, 3H), 7.83-7.87 (m, 1H), 8.02-8.06 (m, 1H),



8.55-8.59 (m, 1H), 8.65-8.68 (m, 1H)


92
2.71 (s, 3H), 7.62-7.70 (m, 3H), 7.86-7.91 (m, 1H), 7.96-8.01 (m, 2H), 8.46-8.50 (m, 1H),



8.61-8.64 (m, 1H)


98
2.29 (s, 3H), 7.14 (m, 2H), 7.42 (m, 4H), 7.91 (m, 2H)


99
2.31 (s, 3H), 7.13 (m, 2H), 7.33 (m, 1H), 7.49 (m, 1H), 7.57 (m, 1H), 7.90 (m, 2H)


100
2.29 (s, 3H), 7.02 (m, 1H), 7.13 (m, 3H), 7.33 (m, 1H), 7.92 (m, 2H)


101
2.28 (s, 3H), 7.16 (m, 2H), 7.30 (m, 1H), 7.94 (m, 2H), 8.84 (m, 1H)


102
2.27 (s, 3H), 7.15 (m, 2H), 7.47 (m, 1H), 7.95 (m, 2H), 8.82 (m, 1H)


103
2.34 (s, 3H), 7.35-7.39 (m, 1H), 7.49-7.53 (m, 1H), 7.59-7.62 (m, 1H), 7.68-7.73 (m, 2H),



8.01-8.05 (m, 2H)


104
2.38 (m, 3H), 3.89-3.91 (m, 3H), 6.73-6.74 (m, 1H), 7.89-7.94 (m, 2H), 8.09-8.13 (m, 2H)



(dmso d6)


108
1.18-1.24 (m, 3H), 2.60-2.66 (m, 2H), 4.21 (s, 2H), 7.40-7.54 (m, 4H), 8.05-8.16 (m, 2H),



8.80-8.85 (m, 1H)


110
1.96 (br s, 1H), 4.81-4.85 (m, 2H), 7.44-7.58 (m, 4H), 7.70-7.74 (m, 2H), 8.04-8.08 (m, 2H)


111
2.33 (s, 3H), 7.39-7.53 (m, 4H), 7.68-7.72 (m, 2H), 8.02-8.06 (m, 2H)


113
1.30-1.35 (m, 3H), 2.69-2.75 (m, 2H), 7.39-7.53 (m, 4H), 7.68-7.72 (m, 2H), 8.03-8.07 (m, 2H)


123
4.16 (s, 2H), 7.42-7.60 (m, 3H), 7.72-7.76 (m, 2H), 8.12-8.16 (m, 2H)


124
2.25 (s, 3H), 4.14 (s, 2H), 7.42-7.53 (m, 3H), 7.69-7.73 (m, 2H), 8.10-8.14 (m, 2H)


127
2.25 (s, 3H), 7.14 (m, 2H), 7.30 (m, 2H), 7.58 (m, 1H), 7.95 (m, 3H)


128
2.25 (s, 3H), 7.14 (m, 2H), 7.29 (m, 1H), 7.34 (s, 1H), 7.93 (m, 2H), 8.33 (m, 1H)


158
7.23-7.29 (m, 2H), 8.02-8.06 (m, 2H), 8.31-8.33 (m, 1H), 8.51-8.53 (m, 1H), 9.01-9.04 (m, 1H)


159
4.16 (s, 2H), 7.13-7.19 (m, 2H), 7.43-7.46 (m, 1H), 7.63-7.66 (m, 1H), 7.87-7.94 (m, 2H),



8.67-8.71 (m, 1H)


160
5.43-5.56 (m, 2H), 7.17-7.23 (m, 2H), 7.37-7.42 (m, 1H), 7.59-7.62 (m, 1H), 7.95-8.02 (m, 2H),



8.68-8.72 (m, 1H)


161
3.40 (s, 3H), 4.55 (s, 2H), 7.14-7.21 (m, 2H), 7.33-7.36 (m, 1H), 7.54-7.57 (m, 1H), 7.95-8.00 (m,



2H), 8.66-8.70 (m, 1H)


163
1.13-1.18 (m, 3H), 3.53-3.59 (m, 2H), 4.59 (s, 2H), 7.15-7.21 (m, 2H), 7.32-7.35 (m, 1H),



7.52-7.55 (m, 1H), 7.95-8.00 (m, 2H), 8.66-8.70 (m, 1H)


164
1.40-1.45 (m, 3H), 4.10 (s, 2H), 4.36-4.40 (m, 2H), 7.43-7.46 (m, 1H), 7.66-7.70 (m, 3H),



7.99-8.02 (m, 2H), 8.64-8.67 (m, 1H)


166
1.29-1.35 (m, 3H), 2.66-2.75 (m, 2H), 7.13-7.20 (m, 2H), 7.28-7.32 (m, 1H), 7.51-7.53 (m, 1H),



7.91-7.98 (m, 2H), 8.65-8.68 (m, 1H)


167
2.73 (s, 3H), 7.24 (m, 2H), 8.15 (m, 1H), 8.31 (d, 1H), 8.51 (s, 1H), 9.00 (d, 1H)


168
0.97-1.00 (m, 3H), 1.79-1.69 (m, 2H), 2.63-2.68 (m, 2H), 7.13-7.20 (m, 2H), 7.28-7.32 (m, 1H),



7.51-7.53 (m, 1H), 7.91-7.98 (m, 2H), 8.65-8.68 (m, 1H)


169
1.31-1.37 (m, 3H), 2.71-2.77 (m, 2H), 7.34-7.37 (m, 1H), 7.54-7.57 (m, 1H), 7.72-7.76 (m, 2H),



8.07-8.11 (m, 2H), 8.68-8.71 (m, 1H)


175
1.53 (s, 9H), 7.24 (m, 2H), 8.00 (m, 2H), 8.10 (m, 1H), 8.35(s, 1H), 8.95 (m, 1H)


176
1.35 (s, 9H), 4.31 (s, 2H), 7.24(m, 2H), 7.35 (m, 1H), 7.61 (m, 1H), 8.00 (m, 2H), 8.65 (m, 1H)


177
1.53-1.58 (m, 3H), 4.54-4.60 (m, 2H), 7.18-7.25 (m, 2H), 7.99-8.06 (m, 2H), 8.23-8.26 (m, 1H),



8.45-8.47 (m, 1H), 8.95-8.98 (m, 1H)


184
0.92-0.97 (m, 3H), 1.36-1.45 (m, 2H), 1.67-1.75 (m, 2H), 2.68-2.73 (m, 2H), 7.34-7.37 (m, 1H),



7.54-7.57 (m, 1H), 7.72-7.76 (m, 2H), 8.11-8.07 (m, 2H), 8.68-8.71 (m, 1H)


185
0.99-1.04 (m, 3H), 1.72-1.81 (m, 2H), 2.65-2.72 (m, 2H), 7.35-7.39 (m, 1H), 7.55-7.57 (m, 1H),



7.68-7.73 (m, 1H), 7.81-7.87 (m, 2H), 8.69-8.72 (m, 1H)


188
1.39-1.44 (m, 3H), 4.08 (s, 2H), 4.32-4.40 (m, 2H), 7.36-7.41 (m, 2H), 7.41-7.45 (m, 1H),



7.66-7.68 (m, 1H), 7.81-7.86 (m, 2H), 8.63-8.66 (m, 1H)


189
1.38-1.44 (m, 3H), 4.08 (s, 2H), 4.32-4.40 (m, 2H), 7.42-7.45 (m, 1H), 7.51-7.57 (m, 2H),



7.66-7.68 (m, 1H), 7.75-7.81 (m, 2H), 8.63-8.66 (m, 1H)


190
1.38-1.43 (m, 3H), 4.10 (s, 2H), 4.32-4.38 (m, 2H), 6.94-7.03 (m, 2H), 7.65-7.72 (m, 2H),



7.43-7.46 (m, 1H), 8.63-8.66 (m, 1H)


191
0.97-1.02 (m, 3H), 1.77-1.87 (m, 2H), 4.11 (s, 2H), 4.26-4.30 (m, 2H), 7.43-7.47 (m, 1H),



7.65-7.71 (m, 3H), 7.99-8.03 (m, 2H), 8.64-8.67 (m, 1H)


192
1.37-1.40 (m, 6H), 4.09 (s, 2H), 4.93-5.01 (m, 1H), 7.43-7.46 (m, 1H), 7.66-7.70 (m, 3H),



7.98-8.02 (m, 2H), 8.63-8.66 (m, 1H)


193
0.95-0.99 (m, 6H), 2.05-2.14 (m, 1H), 4.07-4.10 (m, 2H), 4.11 (s, 2H), 7.43-7.47 (m, 1H),



7.66-7.70 (m, 3H), 7.99-8.03 (m, 2H), 8.64-8.67 (m, 1H)


194
0.94-0.99 (m, 3H), 1.37-1.47 (m, 2H), 1.73-1.80 (m, 2H), 4.10 (s, 2H), 4.30-4.34 (m, 2H),



7.42-7.46 (m, 1H), 7.64-7.71 (m, 3H), 7.99-8.02 (m, 2H), 8.63-8.66 (m, 1H)


195
1.38-1.44 (m, 3H), 4.06 (s, 2H), 4.32-4.40 (m, 2H), 6.50-6.74 (m, 1H), 7.07-7.15 (m, 2H),



7.33-7.37 (m, 1H), 7.61 (s, 1H), 7.83-7.90 (m, 2H), 8.54-8.57 (m, 1H)


197
2.28 (s, 3H), 4.11-4.13 (m, 2H), 7.38-7.41 (m, 1H), 7.60-7.63 (m, 1H), 7.72-7.76 (m, 2H),



8.06-8.10 (m, 2H), 8.67-8.70 (m, 1H)





a1H NMRH data are in ppm downfield from tetramethylsilane, in CDCl3 unless otherwise indicated. Couplings are designated by (s)-singlet, (d)-doublet, (t)-triplet, (m)-multiplet, (t)-triplet, (q)-quartet and (br s)-broad singlet.






BIOLOGICAL EXAMPLES OF THE INVENTION
Test A
Seeds of barnyardgrass (Echinochloa crus-galli), crabgrass, large (large crabgrass, Digitaria sanguinalis), foxtail, giant (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 these species were also treated with postemergence applications of test chemicals formulated in the same manner.
Plants ranged in height from two to ten 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 ten 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





Compounds

















Compounds





















1000 g ai/ha
94
95
96
97
105
106
109
117
118
123
124
130
131
132










Postemergence





















Barnyardgrass
40
60
40
30
10
40
90
80
30
10
70
50
30
80


Corn
40
30
30
10
10
10
90
40
30
40
60
30
30
30


Crabgrass, Large
80
80
70
60
50
80
90
90
90
80
90
90
90
90


Foxtail, Giant
70
60
60
20
—
—
90
90
60
60
90
80
50
90


Morningglory
100
60
80
40
90
100
90
90
100
100
100
100
70
100


Pigweed
100
100
90
60
100
100
100
100
100
100
100
100
100
100


Velvetleaf
80
70
70
50
40
70
80
100
70
100
100
100
40
90


Wheat
30
0
30
0
0
10
50
20
20
20
40
30
0
30














Compounds

Compound














1000 g ai/ha
133
134
167
31 g ai/ha
34











Postemergence














Barnyardgrass
40
30
100
Barnyardgrass
0



Corn
20
20
30
Corn
10



Crabgrass, Large
80
90
100
Crabgrass, Large
10



Foxtail, Giant
70
50
100
Foxtail, Giant
10



Morningglory
90
100
100
Morningglory
20



Pigweed
100
100
100
Pigweed
20



Velvetleaf
90
50
50
Velvetleaf
0



Wheat
30
0
40
Wheat
0













Compounds





















500 g ai/ha
1
2
3
4
5
6
7
8
9
10
11
12
13
14










Postemergence





















Barnyardgrass
20
10
50
30
0
0
90
80
60
50
0
80
0
90


Corn
20
10
30
30
0
0
50
40
30
20
0
30
0
40


Crabgrass, Large
90
20
90
70
0
20
90
80
70
60
0
90
0
90


Foxtail, Giant
70
20
90
40
0
10
90
80
70
50
0
70
10
90


Morningglory
100
20
100
40
0
0
90
90
100
100
0
100
10
100


Pigweed
100
90
100
100
30
30
100
100
100
100
20
100
0
100


Velvetleaf
70
0
60
30
0
0
70
80
80
50
0
100
0
100


Wheat
20
10
40
40
0
0
20
20
20
10
0
30
0
50












Compounds





















500 g ai/ha
15
16
17
18
19
20
21
22
23
24
25
26
27
28










Postemergence





















Barnyardgrass
90
100
90
60
50
0
10
20
90
20
90
90
20
90


Corn
50
50
30
30
20
10
10
20
50
20
30
40
20
50


Crabgrass, Large
90
90
90
80
70
10
40
60
90
20
90
90
40
90


Foxtail, Giant
90
90
80
70
50
10
10
50
90
20
90
90
40
90


Morningglory
100
100
90
90
80
10
40
20
100
20
100
100
90
100


Pigweed
100
100
100
100
100
30
80
80
100
90
100
100
100
100


Velvetleaf
100
100
100
80
70
20
20
30
100
20
100
100
50
100


Wheat
50
30
40
30
30
0
0
—
50
10
60
80
40
50












Compounds





















500 g ai/ha
29
30
31
32
33
35
36
37
38
39
40
41
42
43










Postemergence





















Barnyardgrass
40
0
10
10
0
90
0
20
0
10
40
10
10
20


Corn
20
0
20
10
10
50
0
20
0
10
30
20
10
30


Crabgrass, Large
90
0
50
30
10
90
0
70
50
10
90
30
30
40


Foxtail, Giant
90
0
50
20
10
90
0
80
0
10
90
20
20
30


Morningglory
100
0
100
50
10
100
0
90
0
0
100
10
50
40


Pigweed
100
0
90
100
50
100
20
100
30
50
100
80
90
70


Velvetleaf
80
0
20
20
0
100
10
50
60
0
100
50
20
20


Wheat
30
0
10
0
0
60
0
10
0
0
30
10
10
30












Compounds





















500 g ai/ha
44
45
47
48
49
50
51
52
53
54
55
56
57
58










Postemergence





















Barnyardgrass
20
10
90
30
20
10
10
70
90
90
90
30
0
10


Corn
30
20
40
30
20
10
10
20
40
60
50
20
0
10


Crabgrass, Large
40
70
90
90
90
10
10
100
90
90
90
80
10
10


Foxtail, Giant
30
50
90
70
60
10
10
100
90
90
90
80
0
10


Morningglory
70
80
90
90
50
10
10
100
—
—
—
—
0
10


Pigweed
90
100
100
100
100
20
60
100
100
100
100
100
10
80


Velvetleaf
70
70
100
50
60
10
10
100
100
100
100
90
0
0


Wheat
30
20
50
20
20
0
0
20
30
30
40
20
0
10












Compounds





















500 g ai/ha
59
60
61
62
63
64
65
66
68
69
70
71
72
73










Postemergence





















Barnyardgrass
0
10
10
10
0
0
40
10
10
10
10
10
10
30


Corn
0
10
10
0
0
0
20
10
10
20
20
10
10
20


Crabgrass, Large
0
10
10
0
0
0
50
10
10
20
30
10
10
60


Foxtail, Giant
0
0
10
0
0
0
70
10
10
10
20
10
10
40


Morningglory
0
0
30
0
0
0
—
10
10
30
20
10
10
70


Pigweed
0
10
80
10
10
0
100
30
50
90
100
40
70
100


Velvetleaf
0
0
30
0
0
0
60
10
0
20
50
10
10
40


Wheat
0
0
0
0
0
0
20
10
10
10
10
0
0
20












Compounds





















500 g ai/ha
74
75
76
77
78
79
80
82
83
84
86
87
88
90










Postemergence





















Barnyardgrass
0
10
20
10
10
0
70
0
0
10
0
0
20
10


Corn
0
10
20
10
10
0
20
0
0
30
0
0
10
10


Crabgrass, Large
0
20
30
20
20
0
80
0
0
50
0
0
80
10


Foxtail, Giant
0
20
20
20
30
10
80
0
0
20
0
0
40
10


Morningglory
0
30
20
10
40
0
90
0
0
30
0
0
50
10


Pigweed
0
60
60
100
90
0
100
0
0
90
0
0
100
30


Velvetleaf
0
10
10
10
20
0
100
0
0
20
0
0
80
0


Wheat
0
0
20
0
0
0
40
0
0
0
0
0
10
0












Compounds





















500 g ai/ha
91
92
93
98
99
100
101
102
103
104
107
108
110
111










Postemergence





















Barnyardgrass
10
10
10
80
30
30
60
0
0
30
60
70
30
30


Corn
10
10
10
30
20
20
20
0
0
20
30
30
30
30


Crabgrass, Large
10
30
20
90
70
80
90
10
30
70
90
90
70
90


Foxtail, Giant
10
20
10
90
80
70
90
0
20
50
90
90
30
90


Morningglory
0
30
10
100
80
90
40
0
0
90
80
100
100
100


Pigweed
30
90
20
100
100
90
90
70
70
100
100
100
100
90


Velvetleaf
10
20
20
80
60
70
20
0
10
60
50
80
60
70


Wheat
0
10
0
30
20
20
10
0
0
0
40
30
30
40












Compounds




















500 g ai/ha
112
114
115
116
119
120
121
122
125
126
127
128
129










Postemergence




















Barnyardgrass
30
30
30
20
20
80
0
70
30
70
20
20
90


Corn
20
30
30
30
30
50
10
30
30
30
20
10
40


Crabgrass, Large
90
70
80
80
70
90
10
90
90
90
30
20
90


Foxtail, Giant
80
40
60
50
60
80
0
90
60
90
20
10
90


Morningglory
100
90
100
100
70
100
0
100
100
80
30
30
100


Pigweed
100
90
100
100
100
100
20
100
100
100
60
40
100


Velvetleaf
60
50
30
50
40
80
10
100
70
80
20
30
100


Wheat
30
30
20
10
10
30
0
30
20
20
10
0
30












Compounds





















500 g ai/ha
135
136
137
138
139
140
141
142
143
144
145
146
147
148










Postemergence





















Barnyardgrass
10
90
90
90
100
30
90
100
50
30
90
90
80
90


Corn
20
40
30
70
50
30
50
80
50
30
90
80
40
40


Crabgrass, Large
20
90
90
90
90
50
90
100
100
90
90
90
90
80


Foxtail, Giant
10
90
90
90
100
50
90
100
100
90
100
90
80
80


Morningglory
10
100
100
100
100
90
90
100
90
90
100
90
90
90


Pigweed
50
100
100
100
100
100
100
100
100
100
100
100
100
100


Velvetleaf
30
100
100
100
100
70
90
100
80
50
100
100
90
—


Wheat
0
30
30
60
40
20
50
80
40
20
50
30
50
40












Compounds





















500 g ai/ha
149
150
151
152
153
154
155
156
157
158
159
160
161
162










Postemergence





















Barnyardgrass
80
0
20
20
90
90
90
90
70
0
80
90
70
90


Corn
40
10
20
20
80
80
70
70
40
20
30
60
30
40


Crabgrass, Large
90
20
30
30
100
100
100
100
80
20
40
90
90
90


Foxtail, Giant
90
0
30
50
100
100
100
100
90
0
90
90
90
90


Morningglory
100
0
70
60
100
100
100
90
80
10
90
90
50
90


Pigweed
100
50
80
90
100
100
100
100
100
80
100
100
100
100


Velvetleaf
100
10
50
60
100
100
100
100
—
0
60
100
80
100


Wheat
30
0
0
0
70
50
80
60
20
0
30
50
30
30












Compounds





















500 g ai/ha
163
164
165
166
168
169
170
171
172
173
174
175
176
177










Postemergence





















Barnyardgrass
100
90
90
90
90
90
90
90
90
70
90
0
0
20


Corn
30
40
30
30
50
50
50
30
50
20
30
0
0
30


Crabgrass, Large
100
90
90
90
90
90
100
100
100
90
90
0
0
60


Foxtail, Giant
90
90
90
90
90
90
90
90
90
90
90
0
0
70


Morningglory
80
100
80
100
—
—
100
100
100
90
100
0
0
100


Pigweed
100
100
100
100
100
100
100
100
100
100
100
0
0
100


Velvetleaf
100
100
70
100
100
100
100
90
100
70
80
0
0
50


Wheat
40
60
30
40
50
40
50
40
50
30
40
0
0
30












Compounds





















500 g ai/ha
178
179
180
181
182
183
184
185
186
187
188
189
190
191










Postemergence





















Barnyardgrass
80
90
80
30
80
90
30
90
0
0
90
80
100
100


Corn
30
30
30
10
20
50
20
50
20
0
50
40
90
80


Crabgrass, Large
90
90
90
50
90
90
90
90
0
0
90
90
100
100


Foxtail, Giant
90
90
90
80
100
90
80
90
0
0
90
90
100
100


Morningglory
100
100
100
90
100
100
100
100
10
0
100
80
100
100


Pigweed
100
100
100
100
100
100
100
100
60
0
100
100
100
100


Velvetleaf
100
100
100
70
100
100
90
100
20
0
90
90
100
100


Wheat
40
40
40
20
30
40
20
40
0
0
70
60
100
80













Compounds




















500 g ai/ha
192
193
194
195
196
197
198
199
200
201











Postemergence



















Barnyardgrass
20
20
20
90
90
10
0
10
10
10



Corn
30
30
20
60
80
20
10
20
20
20



Crabgrass, Large
30
30
20
90
90
20
10
20
40
30



Foxtail, Giant
20
20
30
90
90
40
10
20
20
10



Morningglory
70
40
30
100
100
40
20
20
30
50



Pigweed
100
100
100
100
100
70
50
60
100
100



Velvetleaf
100
70
50
100
100
30
10
10
40
40



Wheat
10
10
20
30
70
0
0
0
0
10













Compounds





















125 g ai/ha
1
2
3
4
5
6
7
8
9
10
11
12
13
14










Postemergence





















Barnyardgrass
0
0
30
20
0
0
30
10
50
20
0
30
0
80


Corn
20
10
20
20
0
0
10
20
20
20
0
20
0
20


Crabgrass, Large
70
10
40
30
0
0
70
40
60
40
0
50
0
80


Foxtail, Giant
50
10
30
20
0
0
50
30
50
20
0
50
0
80


Morningglory
50
10
30
20
0
0
90
90
70
100
0
70
10
80


Pigweed
90
30
90
80
10
0
100
60
90
70
0
100
0
100


Velvetleaf
30
0
50
30
0
0
30
30
60
40
0
70
0
100


Wheat
10
0
30
20
0
0
0
0
0
0
0
10
0
30












Compounds





















125 g ai/ha
15
16
17
18
19
20
21
22
23
24
25
26
27
28










Postemergence





















Barnyardgrass
90
90
30
50
20
0
0
10
70
0
50
80
0
70


Corn
30
30
30
20
20
0
0
10
30
10
30
30
20
30


Crabgrass, Large
90
90
90
60
60
0
20
40
90
10
90
90
30
70


Foxtail, Giant
90
90
60
30
30
0
0
20
90
10
90
90
30
90


Morningglory
100
80
50
80
50
0
20
10
90
20
100
100
40
100


Pigweed
100
100
90
100
90
0
60
50
100
40
100
100
90
100


Velvetleaf
100
100
90
70
60
0
10
10
90
20
80
100
40
80


Wheat
30
20
20
20
10
0
0
10
20
10
40
60
20
40












Compounds





















125 g ai/ha
29
30
31
32
33
34
35
36
37
38
39
40
41
42










Postemergence





















Barnyardgrass
20
0
10
10
0
10
40
0
10
0
0
30
10
0


Corn
20
0
10
0
0
10
20
0
10
0
0
10
10
10


Crabgrass, Large
90
0
10
20
0
20
80
0
20
20
0
80
10
10


Foxtail, Giant
60
0
10
10
0
20
60
0
30
0
0
60
10
10


Morningglory
80
0
20
10
0
30
90
0
20
0
0
70
10
10


Pigweed
100
0
60
60
10
80
100
0
80
0
30
100
30
50


Velvetleaf
60
0
10
20
0
10
70
0
20
0
0
70
10
10


Wheat
0
0
0
0
0
0
10
0
0
0
0
20
0
0












Compounds





















125 g ai/ha
43
44
45
47
48
49
50
51
52
53
54
55
56
57










Postemergence





















Barnyardgrass
10
20
10
90
10
10
0
0
20
90
70
90
10
0


Corn
20
30
10
20
10
10
0
0
10
30
30
20
10
0


Crabgrass, Large
30
30
60
80
50
60
0
0
50
90
80
80
50
0


Foxtail, Giant
20
20
20
80
30
30
0
0
50
90
80
90
20
0


Morningglory
0
20
40
90
10
20
0
0
40
—
—
—
—
0


Pigweed
50
70
100
100
100
80
10
10
100
100
100
100
100
0


Velvetleaf
20
60
40
100
30
30
0
0
30
80
90
100
40
0


Wheat
0
20
10
30
10
10
0
0
10
20
20
20
10
0












Compounds





















125 g ai/ha
58
59
60
61
62
63
64
65
66
68
69
70
71
72










Postemergence





















Barnyardgrass
0
0
0
0
0
0
0
10
0
0
10
0
0
0


Corn
0
0
0
10
0
0
0
10
0
0
10
10
0
0


Crabgrass, Large
0
0
0
0
0
0
0
20
10
10
10
10
10
0


Foxtail, Giant
0
0
0
0
0
0
0
20
0
10
10
10
10
0


Morningglory
0
0
0
10
0
0
0
—
0
0
20
10
10
0


Pigweed
50
0
0
40
0
0
0
90
10
10
30
40
10
10


Velvetleaf
0
0
0
10
0
0
0
30
0
—
10
10
0
0


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
0












Compounds





















125 g ai/ha
73
74
75
76
77
78
79
80
82
83
84
86
87
88










Postemergence





















Barnyardgrass
10
0
0
0
0
0
0
30
0
0
0
0
0
10


Corn
10
0
0
10
0
0
0
20
0
0
10
0
0
0


Crabgrass, Large
20
0
10
10
10
10
0
40
0
0
10
0
0
30


Foxtail, Giant
10
0
10
10
10
10
0
30
0
0
10
0
0
10


Morningglory
20
0
0
10
10
0
0
40
0
0
30
0
0
10


Pigweed
70
0
30
50
90
50
0
100
0
0
40
0
0
80


Velvetleaf
20
0
10
0
10
10
0
80
0
0
10
0
0
10


Wheat
10
0
0
0
0
0
0
20
0
0
0
0
0
0












Compounds





















125 g ai/ha
90
91
92
93
98
99
100
101
102
103
104
107
108
110










Postemergence





















Barnyardgrass
0
0
0
0
30
10
10
20
0
0
20
30
40
20


Corn
0
10
10
10
20
20
10
10
0
0
10
20
20
20


Crabgrass, Large
0
0
10
10
90
30
60
70
0
0
50
60
90
50


Foxtail, Giant
0
0
10
10
80
20
50
70
0
0
20
40
60
20


Morningglory
0
0
10
0
80
60
90
40
0
0
60
70
100
90


Pigweed
0
10
30
10
100
70
80
80
10
50
70
90
90
70


Velvetleaf
0
0
20
10
60
10
30
10
0
0
30
40
60
30


Wheat
0
0
0
0
10
0
0
0
0
0
0
20
20
10












Compounds





















125 g ai/ha
111
112
114
115
116
119
120
121
122
125
126
127
128
129










Postemergence





















Barnyardgrass
20
0
30
20
10
10
60
0
40
0
20
10
0
90


Corn
20
20
20
10
20
10
20
0
20
20
20
10
10
30


Crabgrass, Large
90
50
30
50
40
40
80
0
80
60
90
10
10
90


Foxtail, Giant
80
20
30
30
30
20
80
0
60
50
60
10
0
90


Morningglory
70
60
60
90
70
20
90
0
90
60
70
20
30
100


Pigweed
90
90
80
80
50
70
90
0
100
90
100
40
30
100


Velvetleaf
20
50
30
10
20
20
50
0
80
30
40
20
20
70


Wheat
10
10
10
10
10
0
10
0
20
0
10
0
0
20












Compounds





















1000 g ai/ha
94
95
96
97
105
106
109
117
118
123
124
130
131
132










Preemergence





















Barnyardgrass
70
50
70
30
10
50
100
100
70
10
90
50
20
90


Corn
0
10
0
0
0
10
40
50
20
0
10
0
0
0


Crabgrass, Large
100
100
100
40
50
90
100
100
100
60
100
90
90
100


Foxtail, Giant
100
100
90
20
—
—
100
100
100
80
100
90
90
100


Morningglory
60
0
40
0
10
20
50
40
20
0
40
40
10
60


Pigweed
100
90
100
0
90
90
100
100
100
80
100
90
90
100


Velvetleaf
20
40
0
0
10
0
30
30
10
10
80
20
0
60


Wheat
0
0
0
0
0
0
20
10
10
0
0
10
0
0












Compounds





















125 g ai/ha
135
136
137
138
139
140
141
142
143
144
145
146
147
148










Postemergence





















Barnyardgrass
0
60
70
90
90
10
80
100
20
10
80
30
80
80


Corn
10
20
20
50
30
20
30
50
40
10
40
20
30
20


Crabgrass, Large
10
60
90
90
90
20
90
100
80
50
90
80
80
80


Foxtail, Giant
0
90
90
90
90
20
90
100
80
30
90
80
70
80


Morningglory
0
70
80
100
80
50
80
100
50
20
100
90
90
80


Pigweed
20
100
100
100
100
100
100
100
100
100
100
100
100
100


Velvetleaf
10
90
80
100
90
20
70
100
40
40
100
70
50
100


Wheat
0
30
20
50
30
10
20
80
10
0
20
10
20
20












Compounds





















125 g ai/ha
149
150
151
152
153
154
155
156
157
158
159
160
161
162










Postemergence





















Barnyardgrass
30
0
10
20
90
90
90
90
20
0
50
70
30
80


Corn
30
0
10
10
60
30
40
40
20
0
20
30
10
20


Crabgrass, Large
80
0
10
20
100
100
100
100
40
0
20
90
70
90


Foxtail, Giant
80
0
10
30
90
90
90
90
80
0
40
90
60
90


Morningglory
90
0
40
50
90
80
90
90
60
0
60
90
30
90


Pigweed
100
10
60
60
100
100
100
100
100
10
90
100
100
100


Velvetleaf
60
0
30
40
100
100
100
100
40
0
20
90
40
90


Wheat
20
0
0
0
60
20
40
40
0
0
0
40
10
20












Compounds





















125 g ai/ha
163
164
165
166
168
169
170
171
172
173
174
175
176
177










Postemergence





















Barnyardgrass
70
90
40
70
90
80
90
80
90
30
70
0
0
0


Corn
20
30
20
20
20
10
30
20
30
20
20
0
0
20


Crabgrass, Large
70
90
70
90
90
90
100
90
90
60
90
0
0
10


Foxtail, Giant
60
90
60
90
90
80
90
80
90
30
80
0
0
20


Morningglory
30
100
60
90
—
—
100
100
100
90
70
0
0
90


Pigweed
100
100
100
100
100
100
100
100
100
80
100
0
0
60


Velvetleaf
40
100
40
80
100
100
100
70
90
50
70
0
0
20


Wheat
20
50
20
30
40
30
40
30
40
10
30
0
0
20












Compounds





















125 g ai/ha
178
179
180
181
182
183
184
185
186
187
188
189
190
191










Postemergence





















Barnyardgrass
30
90
50
0
30
80
10
70
0
0
90
60
100
60


Corn
20
20
20
0
10
20
10
20
10
0
40
20
60
30


Crabgrass, Large
90
90
90
50
70
90
50
90
0
0
90
80
100
90


Foxtail, Giant
60
90
90
30
50
90
30
90
0
0
90
90
100
90


Morningglory
90
100
100
90
60
100
30
100
0
0
90
60
100
100


Pigweed
100
100
100
90
100
100
100
100
20
0
100
100
100
100


Velvetleaf
60
90
70
30
70
100
40
100
0
0
70
70
100
80


Wheat
20
30
30
0
20
30
10
20
0
0
70
50
70
70













Compounds




















125 g ai/ha
192
193
194
195
196
197
198
199
200
201











Postemergence



















Barnyardgrass
0
10
10
90
80
0
0
10
0
0



Corn
10
10
0
30
70
0
0
10
10
10



Crabgrass, Large
10
10
10
90
90
10
0
10
10
20



Foxtail, Giant
10
10
10
90
90
10
0
10
10
0



Morningglory
30
10
10
80
100
30
10
10
10
10



Pigweed
40
70
40
100
100
30
10
20
50
60



Velvetleaf
20
30
30
90
100
20
10
10
10
20



Wheat
0
0
0
30
50
0
0
0
0
0















Compounds

Compound














1000 g ai/ha
133
134
167
31 g ai/ha
34











Preemergence














Barnyardgrass
40
30
100
Barnyardgrass
0



Corn
10
10
30
Corn
0



Crabgrass, Large
90
100
100
Crabgrass, Large
0



Foxtail, Giant
90
100
100
Foxtail, Giant
0



Morningglory
40
10
—
Morningglory
0



Pigweed
90
90
100
Pigweed
0



Velvetleaf
40
0
20
Velvetleaf
0



Wheat
0
0
80
Wheat
0













Compounds





















500 g ai/ha
1
2
3
4
5
6
7
8
9
10
11
12
13
14










Preemergence





















Barnyardgrass
50
10
50
60
0
0
100
80
70
10
0
80
0
90


Corn
0
0
10
0
0
0
30
0
10
0
0
10
0
30


Crabgrass, Large
100
90
100
90
0
0
100
100
100
90
0
100
0
100


Foxtail, Giant
100
50
100
100
0
0
100
90
90
80
0
100
0
100


Morningglory
20
0
50
40
0
0
80
90
60
10
0
40
0
80


Pigweed
90
60
100
100
0
0
100
100
100
80
0
100
0
100


Velvetleaf
10
0
10
0
0
0
60
60
50
20
0
70
0
90


Wheat
0
0
40
30
0
0
0
10
0
0
0
0
0
50












Compounds





















500 g ai/ha
15
16
17
18
19
20
21
22
23
24
25
26
27
28










Preemergence





















Barnyardgrass
100
100
90
30
50
0
10
10
100
0
90
90
10
90


Corn
50
20
20
0
0
0
0
0
40
0
30
50
0
20


Crabgrass, Large
100
100
100
90
80
0
60
40
100
20
100
100
40
90


Foxtail, Giant
100
100
100
90
90
0
30
80
100
70
100
100
80
100


Morningglory
80
80
50
50
50
0
0
0
80
0
80
80
0
—


Pigweed
100
100
100
100
90
0
50
10
100
20
100
100
80
100


Velvetleaf
80
80
40
30
30
0
0
0
100
0
80
90
0
80


Wheat
50
20
0
0
0
0
0
0
70
0
80
80
0
20












Compounds





















500 g ai/ha
29
30
31
32
33
35
36
37
38
39
40
41
42
43










Preemergence





















Barnyardgrass
50
0
0
0
0
90
0
90
0
0
80
20
10
20


Corn
0
0
0
0
0
30
0
—
0
0
10
0
0
10


Crabgrass, Large
100
0
60
30
10
100
10
100
60
50
100
70
50
80


Foxtail, Giant
100
0
90
80
0
100
0
100
20
10
100
70
70
90


Morningglory
10
0
0
0
0
50
0
20
0
0
10
10
10
—


Pigweed
90
0
50
70
0
100
0
100
10
0
100
50
60
60


Velvetleaf
50
0
0
0
0
50
0
10
0
0
20
10
0
0


Wheat
0
0
0
0
0
0
0
0
0
0
20
0
0
0












Compounds





















500 g ai/ha
44
45
47
48
49
50
51
52
53
54
55
56
57
58










Preemergence





















Barnyardgrass
30
10
100
30
30
0
0
90
100
100
100
80
0
0


Corn
20
0
30
0
10
0
0
10
20
40
50
10
0
0


Crabgrass, Large
90
70
100
100
100
20
0
100
100
100
100
100
0
10


Foxtail, Giant
90
60
100
100
100
40
10
100
100
100
100
100
0
10


Morningglory
—
10
80
20
10
0
0
20
40
90
80
10
0
0


Pigweed
90
20
100
90
100
10
0
—
100
100
100
90
0
30


Velvetleaf
50
10
100
0
10
0
0
10
50
60
70
10
0
0


Wheat
30
0
40
0
20
0
0
0
30
30
40
10
0
0












Compounds





















500 g ai/ha
59
60
61
62
63
64
65
66
68
69
70
71
72
73










Preemergence





















Barnyardgrass
0
0
0
0
0
0
70
0
0
0
0
0
0
40


Corn
0
0
0
0
0
0
10
0
0
0
0
0
0
0


Crabgrass, Large
0
0
10
0
0
0
100
50
0
10
40
10
10
90


Foxtail, Giant
0
0
10
0
0
0
100
70
0
0
50
0
20
90


Morningglory
0
0
0
0
0
0
20
0
0
0
0
0
0
10


Pigweed
0
0
10
0
0
0
100
10
0
10
10
0
10
100


Velvetleaf
0
0
0
0
0
0
10
0
0
0
0
0
0
10


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
10












Compounds





















500 g ai/ha
74
75
76
77
78
79
80
82
83
84
86
87
88
90










Preemergence





















Barnyardgrass
0
20
0
0
20
0
70
0
0
0
0
0
10
0


Corn
0
0
0
0
0
0
10
0
0
0
0
0
0
0


Crabgrass, Large
0
70
40
10
80
0
100
0
0
60
0
0
50
0


Foxtail, Giant
0
90
80
10
70
0
100
0
0
30
0
0
40
0


Morningglory
0
—
0
0
10
0
60
0
0
0
0
0
0
0


Pigweed
0
40
20
10
70
0
100
0
0
50
0
0
50
0


Velvetleaf
0
0
0
0
20
0
70
0
0
0
0
0
0
0


Wheat
0
10
0
0
0
0
40
0
0
0
0
0
0
0












Compounds





















500 g ai/ha
91
92
93
98
99
100
101
102
103
104
107
108
110
111










Preemergence





















Barnyardgrass
0
0
0
60
10
20
80
0
0
20
80
80
0
80


Corn
0
0
0
10
0
0
10
0
0
0
10
0
0
20


Crabgrass, Large
0
40
0
100
60
90
100
0
10
90
100
100
20
100


Foxtail, Giant
0
20
0
100
80
70
100
0
0
90
100
100
20
100


Morningglory
0
0
0
10
0
0
10
0
0
0
30
20
20
30


Pigweed
0
10
0
100
60
90
100
0
30
90
100
100
50
90


Velvetleaf
0
0
0
50
20
0
0
0
0
30
10
20
10
50


Wheat
0
0
0
20
0
0
0
0
0
0
0
0
0
0












Compounds




















500 g ai/ha
112
114
115
116
119
120
121
122
125
126
127
128
129










Preemergence




















Barnyardgrass
40
0
60
30
30
100
0
70
50
80
10
0
100


Corn
0
0
10
10
0
30
0
20
0
20
0
0
60


Crabgrass, Large
100
30
100
100
100
100
10
100
90
100
40
20
100


Foxtail, Giant
90
10
100
90
100
100
0
100
90
90
30
20
100


Morningglory
20
30
10
10
10
30
0
50
10
30
0
20
60


Pigweed
100
10
100
100
100
100
0
100
90
100
20
0
100


Velvetleaf
20
10
20
20
10
70
0
60
50
40
0
0
70


Wheat
0
0
10
10
0
20
0
20
0
0
0
0
50












Compounds





















500 g ai/ha
135
136
137
138
139
140
141
142
143
144
145
146
147
148










Preemergence





















Barnyardgrass
0
100
70
100
100
30
100
100
90
30
100
100
100
100


Corn
0
10
0
60
30
0
30
80
20
0
40
10
30
20


Crabgrass, Large
0
100
90
90
100
50
100
100
100
100
100
100
100
100


Foxtail, Giant
0
100
90
100
100
70
100
100
100
100
100
100
100
100


Morningglory
0
60
60
90
70
0
60
80
0
0
60
60
80
90


Pigweed
0
90
100
100
100
80
100
100
100
100
100
100
100
100


Velvetleaf
0
60
20
100
90
30
60
90
20
0
80
50
50
70


Wheat
0
10
0
60
50
0
20
80
10
0
60
30
50
50












Compounds





















500 g ai/ha
149
150
151
152
153
154
155
156
157
158
159
160
161
162










Preemergence





















Barnyardgrass
90
0
0
0
100
100
100
100
100
0
80
100
60
100


Corn
20
0
0
0
80
70
80
70
0
0
0
40
10
30


Crabgrass, Large
100
0
10
10
100
100
100
100
90
0
30
100
100
100


Foxtail, Giant
100
0
20
20
100
100
100
100
100
0
90
100
100
100


Morningglory
30
0
0
0
100
80
90
90
0
0
0
70
10
90


Pigweed
100
0
60
40
100
100
100
100
100
0
90
100
100
100


Velvetleaf
50
0
0
0
100
70
—
—
0
0
0
70
50
100


Wheat
50
0
0
0
70
20
70
80
0
0
0
50
10
30












Compounds





















500 g ai/ha
163
164
165
166
168
169
170
171
172
173
174
175
176
177










Preemergence





















Barnyardgrass
100
100
100
100
100
90
—
—
—
—
—
0
0
70


Corn
10
30
10
30
40
20
40
30
60
0
20
0
0
0


Crabgrass, Large
100
100
100
100
100
100
100
100
100
100
100
0
0
100


Foxtail, Giant
100
100
100
100
100
100
100
100
100
100
100
0
0
100


Morningglory
30
90
—
—
50
40
90
60
80
10
40
0
0
40


Pigweed
100
100
100
100
100
100
100
100
100
70
100
0
0
50


Velvetleaf
20
100
10
70
90
90
100
80
90
20
70
0
0
20


Wheat
0
60
0
50
60
50
80
60
70
0
30
0
0
0












Compounds





















500 g ai/ha
178
179
180
181
182
183
184
185
186
187
188
189
190
191










Preemergence





















Barnyardgrass
100
100
80
20
90
100
50
100
0
0
100
90
100
100


Corn
10
30
20
0
10
30
0
30
0
0
20
10
90
60


Crabgrass, Large
100
100
100
80
100
100
100
100
0
0
100
100
100
100


Foxtail, Giant
100
100
100
80
100
100
90
100
0
0
100
100
100
100


Morningglory
60
70
70
10
10
90
10
100
0
0
90
30
80
30


Pigweed
100
100
100
90
100
100
100
100
0
0
100
100
100
100


Velvetleaf
60
100
60
0
70
80
30
100
0
0
90
60
100
80


Wheat
10
50
40
0
0
60
0
50
0
0
50
50
80
70













Compounds




















500 g ai/ha
192
193
194
195
196
197
198
199
200
201











Preemergence



















Barnyardgrass
0
0
0
100
100
0
0
0
0
0



Corn
0
0
0
30
50
0
0
0
0
0



Crabgrass, Large
70
40
10
100
100
0
0
70
100
20



Foxtail, Giant
80
70
30
100
100
0
0
50
100
20



Morningglory
10
0
0
60
90
0
0
0
10
0



Pigweed
40
20
10
100
100
0
0
30
100
10



Velvetleaf
0
0
0
80
100
0
0
0
0
0



Wheat
0
0
0
50
70
0
0
0
0
0













Compounds





















125 g ai/ha
1
2
3
4
5
6
7
8
9
10
11
12
13
14










Preemergence





















Barnyardgrass
20
0
10
10
0
0
40
20
30
0
0
30
0
70


Corn
0
0
0
0
0
0
0
0
0
0
0
0
0
20


Crabgrass, Large
70
10
90
80
0
0
100
90
90
40
0
90
0
90


Foxtail, Giant
60
10
90
80
0
0
90
60
80
20
0
80
0
100


Morningglory
0
0
0
0
0
0
30
30
50
0
0
10
0
60


Pigweed
60
0
70
50
0
0
100
90
90
60
0
80
0
90


Velvetleaf
0
0
0
0
0
0
30
20
30
0
0
60
0
70


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
30












Compounds





















125 g ai/ha
15
16
17
18
19
20
21
22
23
24
25
26
27
28










Preemergence





















Barnyardgrass
100
90
30
20
20
0
0
0
70
0
80
90
0
50


Corn
20
10
0
0
0
0
0
0
10
0
10
30
0
20


Crabgrass, Large
100
90
100
90
60
0
0
10
100
0
90
100
20
30


Foxtail, Giant
100
100
90
80
50
0
0
20
100
20
100
100
10
100


Morningglory
60
—
0
10
10
0
0
0
80
0
30
80
0
20


Pigweed
100
90
90
80
80
0
0
10
100
0
100
100
0
100


Velvetleaf
70
30
30
20
20
0
0
0
50
0
20
80
0
20


Wheat
30
10
0
0
0
0
0
0
0
0
20
50
0
0












Compounds





















125 g ai/ha
29
30
31
32
33
34
35
36
37
38
39
40
41
42










Preemergence





















Barnyardgrass
10
0
0
0
0
0
60
0
30
0
0
30
10
0


Corn
0
0
0
0
0
0
10
0
0
0
0
0
0
0


Crabgrass, Large
90
0
0
10
0
50
90
0
90
50
0
100
20
10


Foxtail, Giant
80
0
30
10
0
30
80
0
90
0
0
100
40
10


Morningglory
0
0
0
0
0
0
20
0
0
0
0
0
0
0


Pigweed
50
0
0
0
0
10
90
0
70
0
0
90
20
10


Velvetleaf
0
0
0
0
0
0
30
0
0
0
0
10
10
0


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
0












Compounds





















125 g ai/ha
43
44
45
47
48
49
50
51
52
53
54
55
56
57










Preemergence





















Barnyardgrass
0
0
0
90
0
10
0
0
20
80
80
90
0
0


Corn
0
0
0
20
0
0
0
0
0
0
10
20
0
0


Crabgrass, Large
30
60
70
100
30
80
10
0
100
100
100
100
90
0


Foxtail, Giant
20
70
50
100
40
80
10
0
100
100
100
100
30
0


Morningglory
—
—
0
70
0
0
0
0
10
30
60
50
0
0


Pigweed
50
20
10
100
40
60
0
0
100
90
100
100
30
0


Velvetleaf
0
0
0
80
0
0
0
0
0
10
30
40
0
0


Wheat
0
0
0
30
0
10
0
0
0
10
10
10
0
0












Compounds





















125 g ai/ha
58
59
60
61
62
63
64
65
66
68
69
70
71
72










Preemergence





















Barnyardgrass
0
0
0
0
0
0
0
10
0
0
0
0
0
0


Corn
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Crabgrass, Large
0
0
0
0
0
0
0
30
10
0
0
0
0
0


Foxtail, Giant
0
0
0
0
0
0
0
90
10
0
0
0
0
0


Morningglory
0
0
0
0
0
0
0
10
0
0
0
0
0
0


Pigweed
0
0
0
0
0
0
0
80
0
0
0
0
0
0


Velvetleaf
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
0












Compounds





















125 g ai/ha
73
74
75
76
77
78
79
80
82
83
84
86
87
88










Preemergence





















Barnyardgrass
0
0
10
0
0
0
0
20
0
0
0
0
0
0


Corn
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Crabgrass, Large
50
0
20
10
0
60
0
90
0
0
0
0
0
0


Foxtail, Giant
60
0
50
10
0
20
0
90
0
0
0
0
0
0


Morningglory
0
0
—
0
0
0
0
0
0
0
0
0
0
0


Pigweed
30
0
30
0
0
60
0
100
0
0
0
0
0
0


Velvetleaf
0
0
0
0
0
10
0
30
0
0
0
0
0
0


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
0












Compounds





















125 g ai/ha
90
91
92
93
98
99
100
101
102
103
104
107
108
110










Preemergence





















Barnyardgrass
0
0
0
0
10
0
0
50
0
0
10
30
30
0


Corn
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Crabgrass, Large
0
0
10
0
80
30
10
100
0
0
60
100
90
0


Foxtail, Giant
0
0
10
0
70
10
20
100
0
0
60
90
80
0


Morningglory
0
0
0
0
0
0
0
0
0
0
0
20
0
10


Pigweed
0
0
0
0
60
20
10
100
0
10
30
70
80
0


Velvetleaf
0
0
0
0
0
0
0
0
0
0
0
10
0
0


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
0












Compounds





















125 g ai/ha
111
112
114
115
116
119
120
121
122
125
126
127
128
129










Preemergence





















Barnyardgrass
20
0
0
30
0
0
90
0
20
30
70
0
0
100


Corn
0
0
0
0
0
0
20
0
10
0
0
0
0
50


Crabgrass, Large
80
80
0
80
70
70
100
0
90
80
100
10
0
100


Foxtail, Giant
70
60
0
60
60
50
100
0
90
80
70
10
0
100


Morningglory
0
0
10
0
0
0
10
0
20
0
10
0
0
50


Pigweed
70
90
0
100
50
60
100
0
90
70
100
0
0
100


Velvetleaf
0
0
0
0
0
0
40
0
30
0
10
0
0
60


Wheat
0
0
0
0
0
0
10
0
0
0
0
0
0
10












Compounds





















125 g ai/ha
135
136
137
138
139
140
141
142
143
144
145
146
147
148










Preemergence





















Barnyardgrass
0
70
50
90
80
0
40
100
30
0
100
90
90
90


Corn
0
0
0
30
10
0
0
30
0
0
10
0
10
10


Crabgrass, Large
0
80
90
90
100
20
100
100
90
50
100
100
100
100


Foxtail, Giant
0
100
90
100
100
20
100
100
90
50
100
100
100
100


Morningglory
0
20
40
70
50
0
30
50
0
0
10
10
—
40


Pigweed
0
90
100
100
100
30
100
100
100
50
100
100
100
100


Velvetleaf
0
30
20
70
30
20
20
60
0
0
50
10
20
20


Wheat
0
0
0
30
10
0
0
70
0
0
20
0
30
30












Compounds





















125 g ai/ha
149
150
151
152
153
154
155
156
157
158
159
160
161
162










Preemergence





















Barnyardgrass
60
0
0
0
100
100
100
100
20
0
10
100
20
90


Corn
10
0
0
0
70
20
60
40
0
0
0
20
10
20


Crabgrass, Large
90
0
0
0
100
100
100
100
20
0
10
100
100
100


Foxtail, Giant
90
0
0
0
100
100
100
100
90
0
40
100
100
100


Morningglory
10
0
0
0
80
20
80
80
0
0
0
40
10
30


Pigweed
90
0
10
0
100
100
100
100
80
0
70
100
100
100


Velvetleaf
20
0
0
0
80
30
—
30
0
0
0
50
0
100


Wheat
0
0
0
0
50
0
10
20
0
0
0
30
0
10












Compounds





















125 g ai/ha
163
164
165
166
168
169
170
171
172
173
174
175
176
177










Preemergence





















Barnyardgrass
90
90
30
90
90
80
—
—
—
—
—
0
0
0


Corn
0
30
0
10
20
20
30
10
30
0
10
0
0
0


Crabgrass, Large
100
100
100
100
100
100
100
100
100
60
100
0
0
90


Foxtail, Giant
100
100
90
100
100
100
100
100
100
80
90
0
0
90


Morningglory
10
80
—
—
20
20
70
50
60
0
20
0
0
20


Pigweed
100
100
100
100
100
100
100
100
100
50
100
0
0
10


Velvetleaf
0
80
0
30
30
50
90
60
80
0
50
0
0
0


Wheat
0
50
0
10
40
20
60
10
50
0
0
0
0
0












Compounds





















125 g ai/ha
178
179
180
181
182
183
184
185
186
187
188
189
190
191










Preemergence





















Barnyardgrass
20
90
60
0
30
90
0
100
0
0
90
80
100
90


Corn
0
20
10
0
0
20
0
10
0
0
10
10
30
20


Crabgrass, Large
90
100
100
10
90
100
70
100
0
0
100
100
100
100


Foxtail, Giant
90
100
100
10
90
100
70
100
0
0
100
100
100
100


Morningglory
0
40
40
0
0
70
0
60
0
0
20
20
80
20


Pigweed
100
100
100
60
80
100
90
100
0
0
100
100
100
100


Velvetleaf
10
80
50
0
60
70
0
90
0
0
40
20
40
30


Wheat
0
20
20
0
0
30
0
30
0
0
30
20
60
40













Compounds




















125 g ai/ha
192
193
194
195
196
197
198
199
200
201











Preemergence



















Barnyardgrass
0
0
0
90
100
0
0
0
0
0



Corn
0
0
0
20
30
0
0
0
0
0



Crabgrass, Large
0
0
0
100
100
0
0
20
80
0



Foxtail, Giant
0
10
0
100
100
0
0
0
70
0



Morningglory
0
0
0
50
60
0
0
0
0
0



Pigweed
10
0
0
100
100
0
0
10
50
0



Velvetleaf
0
0
0
70
80
0
0
0
0
0



Wheat
0
0
0
20
50
0
0
0
0
0










Test B
Seeds selected from rice (Oryza sativa), sedge, umbrella (small-flower umbrella sedge Cyperus difformis), ducksalad (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
3
4
5
6
24
25
26
27
28
34
43
44
53
54










Flood





















Barnyardgrass
0
20
0
0
0
30
60
20
90
65
0
0
60
30


Ducksalad
0
40
0
0
0
90
40
50
95
75
85
0
85
85


Rice
0
0
0
0
0
35
80
10
80
35
0
0
50
30


Sedge, Umbrella
0
70
0
0
0
95
90
20
95
90
100
0
85
85












Compounds














250 g ai/ha
55
56
65
86
87











Flood














Barnyardgrass
70
30
30
0
0



Ducksalad
100
80
60
0
0



Rice
60
40
25
0
0



Sedge, Umbrella
100
80
75
50
50













Compounds





















250 g ai/ha
135
136
137
138
139
140
141
142
143
144
145
146
147
148










Flood





















Barnyardgrass
0
45
45
80
65
30
20
70
40
30
90
50
55
65


Ducksalad
0
75
50
90
70
0
85
90
0
40
60
60
40
85


Rice
0
35
40
50
45
0
35
60
30
20
80
35
50
45


Sedge, Umbrella
0
85
70
90
80
0
85
90
75
80
85
80
80
85












Compounds





















250 g ai/ha
149
150
151
152
153
154
155
156
157
158
159
160
168
169










Flood





















Barnyardgrass
40
20
0
0
80
60
75
75
0
0
30
65
80
75


Ducksalad
60
0
0
0
90
80
80
90
20
0
20
90
80
85


Rice
30
0
30
0
60
45
50
50
0
75
30
55
60
55


Sedge, Umbrella
60
0
0
0
90
80
80
85
40
0
60
85
85
85












Compounds




















250 g ai/ha
170
171
172
173
174
184
185
192
195
196
197
198
201










Flood




















Barnyardgrass
80
70
80
0
70
25
90
0
85
85
0
0
0


Ducksalad
35
0
0
0
50
0
65
0
100
100
0
0
0


Rice
60
60
50
0
50
25
65
0
60
70
0
0
0


Sedge, Umbrella
90
85
75
0
75
60
95
0
100
100
0
0
0












Compounds





















125 g ai/ha
161
162
163
164
165
166
167
175
176
177
178
179
180
181










Flood





















Barnyardgrass
0
70
15
60
10
70
0
0
0
0
0
0
0
0


Ducksalad
0
0
70
0
40
70
0
0
0
0
30
65
60
0


Rice
20
25
15
45
20
80
30
0
0
0
20
35
30
20


Sedge, Umbrella
80
80
80
75
70
70
50
0
0
40
60
75
70
0












Compounds



















125 g ai/ha
182
183
186
187
188
189
190
191
193
194
199
200










Flood



















Barnyardgrass
0
30
0
0
75
0
70
50
0
0
0
0


Ducksalad
0
65
0
0
90
20
70
20
0
0
0
0


Rice
15
45
0
0
50
35
50
50
0
0
0
0


Sedge, Umbrella
50
95
0
0
100
0
95
50
0
0
0
0









Test C
Seeds of plant species selected from blackgrass (Alopecurus myosuroides), bromegrass, downy (downy bromegrass, Bromus tectorum), foxtail, green (green foxtail, Setaria viridis), ryegrass, Italian (Italian ryegrass, Lolium multiflorum), winter wheat (Triticum aestivum), wild oat (Avena fatua), galium (catchweed bedstraw, Galium aparine), bermudagrass (Cynodon dactylon), surinam grass (Brachiaria decumbens), cocklebur (common cocklebur, Xanthium strumarium), corn (Zea mays), large crabgrass (Digitaria sanguinalis), woolly cupgrass (Eriochloa villosa), foxtail, giant (giant foxtail, Setaria faberii), goosegrass (Eleusine indica), johnsongrass (Sorghum halepense), kochia (Kochia scoparia), lambsquarters (Chenopodium album), morningglory (Ipomoea coccinea), nightshade (eastern black nightshade, Solanum ptycanthum), nutsedge, yellow (yellow nutsedge, Cyperus esculentus), pigweed (Amaranthus retroflexus), ragweed (common ragweed, Ambrosia elation), soybean (Glycine max), 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 barley, Hordeum vulgare), canarygrass (Phalaris minor), chickweed (common chickweed, Stellaria media) windgrass (Apera spica-venti) and deadnettle (henbit deadnettle, Lamium amplexicaule) 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.
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
1
2
7
8
9
10
11
12
13
14
15
16
17
18










Flood





















Barnyardgrass
0
0
20
0
30
0
0
60
0
70
75
80
45
0


Ducksalad
0
0
70
45
0
0
0
70
0
60
60
100
20
0


Rice
0
0
15
0
0
0
0
25
0
45
50
50
45
0


Sedge, Umbrella
0
70
85
75
85
0
0
80
0
75
80
95
75
65












Compounds





















250 g ai/ha
19
20
21
22
23
29
30
31
32
33
35
36
37
38










Flood





















Barnyardgrass
0
0
0
0
25
20
0
0
0
0
30
0
35
0


Ducksalad
0
0
0
0
85
0
0
0
0
0
75
0
70
0


Rice
0
0
0
0
30
0
0
0
0
0
0
0
20
0


Sedge, Umbrella
70
0
0
0
90
75
30
0
0
0
80
0
0
0












Compounds





















250 g ai/ha
39
40
41
42
45
47
48
49
50
51
52
57
58
59










Flood





















Barnyardgrass
0
30
0
0
0
80
30
15
0
0
75
0
0
0


Ducksalad
40
70
0
0
0
90
65
40
0
0
95
0
0
0


Rice
10
25
0
0
0
60
20
0
0
0
40
0
0
0


Sedge, Umbrella
20
80
0
0
0
90
45
75
0
0
85
0
0
0












Compounds





















250 g ai/ha
60
61
62
63
64
66
68
70
71
72
73
74
75
76










Flood





















Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ducksalad
0
0
0
0
0
0
0
0
0
0
85
0
0
0


Rice
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












Compounds





















250 g ai/ha
77
78
79
80
82
83
84
88
90
91
92
93
94
95










Flood





















Barnyardgrass
0
20
0
20
0
0
10
0
0
0
0
0
0
0


Ducksalad
0
0
0
0
0
30
40
0
0
0
0
0
60
0


Rice
0
0
0
0
0
25
20
0
0
0
0
0
0
0


Sedge, Umbrella
0
0
0
70
0
30
20
0
0
0
0
0
75
0












Compounds





















250 g ai/ha
96
98
101
105
106
107
108
109
111
115
116
117
118
119










Flood





















Barnyardgrass
10
70
60
0
40
25
30
75
35
60
60
80
65
30


Ducksalad
50
70
65
0
70
40
45
80
80
20
50
85
70
80


Rice
0
40
20
0
30
25
20
25
30
40
30
40
20
25


Sedge, Umbrella
80
80
75
0
80
80
85
85
85
80
85
85
75
85












Compounds



















250 g ai/ha
120
122
123
124
125
126
129
130
131
132
133
134










Flood



















Barnyardgrass
80
40
0
50
10
40
85
15
10
0
15
15


Ducksalad
85
65
75
90
90
65
90
20
20
20
20
0


Rice
80
30
10
20
10
20
50
15
0
0
0
0


Sedge, Umbrella
90
85
75
90
85
80
95
75
0
65
50
0












Compounds





















125 g ai/ha
7
8
16
17
18
19
20
21
22
23
29
30
31
32










Flood





















Barnyardgrass
0
0
70
40
0
0
0
0
0
20
0
0
0
0


Ducksalad
30
0
95
0
0
0
0
0
0
60
0
0
0
0


Rice
0
0
40
35
0
0
0
0
0
0
0
0
0
0


Sedge, Umbrella
50
0
95
30
40
0
0
0
0
80
70
20
0
0












Compounds





















125 g ai/ha
33
35
36
40
41
45
47
49
57
58
59
60
61
62










Flood





















Barnyardgrass
0
0
0
30
0
0
80
10
0
0
0
0
0
0


Ducksalad
0
70
0
60
0
0
90
30
0
0
0
0
0
0


Rice
0
0
0
20
0
0
60
0
0
0
0
0
0
0


Sedge, Umbrella
0
80
0
80
0
0
90
70
0
0
0
0
0
0












Compounds





















125 g ai/ha
63
64
68
70
71
72
73
74
75
76
77
78
79
80










Flood





















Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ducksalad
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Rice
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












Compounds





















125 g ai/ha
82
83
84
88
90
91
92
93
94
98
101
105
106
107










Flood





















Barnyardgrass
0
0
0
0
0
0
0
0
0
30
55
0
20
20


Ducksalad
0
20
0
0
0
0
0
0
40
30
50
0
70
20


Rice
0
20
20
0
0
0
0
0
0
30
15
0
25
0


Sedge, Umbrella
0
20
0
0
0
0
0
0
60
40
50
0
75
60












Compounds





















125 g ai/ha
108
109
111
115
116
117
118
119
120
122
123
124
125
126
























Barnyardgrass
20
40
20
45
40
65
50
25
80
40
0
50
0
30


Ducksalad
30
60
70
0
30
80
70
80
80
60
75
90
75
20


Rice
15
15
25
30
20
25
15
25
70
25
0
15
0
10


Sedge, Umbrella
75
85
80
75
75
75
70
85
90
85
50
90
80
75














Compound



125 g ai/ha
129











Flood










Barnyardgrass
80



Ducksalad
80



Rice
40



Sedge, Umbrella
85













Compounds





















62 g ai/ha
1
2
7
8
9
10
11
12
13
14
15
16
17
18










Flood





















Barnyardgrass
0
0
0
0
0
0
0
40
0
50
65
65
20
0


Ducksalad
0
0
0
0
0
0
0
60
0
40
40
85
0
0


Rice
0
0
0
0
0
0
0
0
0
40
45
30
15
0


Sedge, Umbrella
0
0
40
0
40
0
0
50
0
40
75
90
20
0












Compounds





















62 g ai/ha
19
20
21
22
23
29
30
31
32
33
35
36
37
38










Flood





















Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
0
10
0


Ducksalad
0
0
0
0
60
0
0
0
0
0
65
0
0
0


Rice
0
0
0
0
0
0
0
0
0
0
0
0
10
0


Sedge, Umbrella
0
0
0
0
75
60
0
0
0
0
75
0
0
0












Compounds





















62 g ai/ha
39
40
41
42
45
47
48
49
50
51
52
57
58
59










Flood





















Barnyardgrass
0
20
0
0
0
50
10
0
0
0
40
0
0
0


Ducksalad
0
30
0
0
0
90
20
0
0
0
80
0
0
0


Rice
0
10
0
0
0
50
10
0
0
0
15
0
0
0


Sedge, Umbrella
0
75
0
0
0
85
0
0
0
0
65
0
0
0












Compounds





















62 g ai/ha
60
61
62
63
64
66
68
70
71
72
73
74
75
76










Flood





















Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ducksalad
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Rice
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












Compounds





















62 g ai/ha
77
78
79
80
82
83
84
88
90
91
92
93
94
95










Flood





















Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ducksalad
0
0
0
0
0
20
0
0
0
0
0
0
0
0


Rice
0
0
0
0
0
20
0
0
0
0
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
20
0
0
0
0
0
0
50
0












Compounds





















62 g ai/ha
96
98
101
105
106
107
108
109
111
115
116
117
118
119










Flood





















Barnyardgrass
10
0
0
0
0
15
0
20
0
40
35
60
30
20


Ducksalad
40
0
20
0
60
0
0
20
30
0
0
50
30
50


Rice
0
0
0
0
0
0
0
15
0
20
0
15
0
15


Sedge, Umbrella
75
0
0
0
50
40
20
63
65
70
60
70
65
75












Compounds



















62 g ai/ha
120
122
123
124
125
126
129
130
131
132
133
134










Flood



















Barnyardgrass
65
20
0
40
0
0
75
0
0
0
0
0


Ducksalad
70
0
40
90
0
0
75
0
0
0
0
0


Rice
60
0
0
0
0
0
30
0
0
0
0
0


Sedge, Umbrella
85
75
0
90
40
40
75
30
0
0
0
0












Compounds





















31 g ai/ha
7
8
16
17
18
19
20
21
22
23
29
30
31
32










Flood





















Barnyardgrass
0
0
25
0
0
0
0
0
0
0
0
0
0
0


Ducksalad
0
0
70
0
0
0
0
0
0
50
0
0
0
0


Rice
0
0
20
10
0
0
0
0
0
0
0
0
0
0


Sedge, Umbrella
30
0
80
0
0
0
0
0
0
60
50
0
0
0












Compounds





















31 g ai/ha
33
35
36
40
41
45
47
49
57
58
59
60
61
62










Flood





















Barnyardgrass
0
0
0
20
0
0
40
0
0
0
0
0
0
0


Ducksalad
0
40
0
30
0
0
0
0
0
0
0
0
0
0


Rice
0
0
0
0
0
0
30
0
0
0
0
0
0
0


Sedge, Umbrella
0
75
0
70
0
0
75
0
0
0
0
0
0
0












Compounds





















31 g ai/ha
63
64
68
70
71
72
73
74
75
76
77
78
79
80










Flood





















Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ducksalad
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Rice
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












Compounds





















31 g ai/ha
82
83
84
88
90
91
92
93
94
98
101
105
106
107










Flood





















Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ducksalad
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Rice
0
10
0
0
0
0
0
0
0
0
0
0
0
0


Sedge, Umbrella
0
10
0
0
0
0
0
0
0
0
0
0
50
0












Compounds


















31 g ai/ha
108
109
111
117
118
122
123
124
125
126
129










Flood


















Barnyardgrass
0
0
0
50
20
10
0
20
0
0
55


Ducksalad
0
0
0
30
0
0
0
20
0
0
70


Rice
0
15
0
15
0
0
0
0
0
0
20


Sedge, Umbrella
20
38
45
65
40
70
0
50
0
30
75













Compounds




















250 g ai/ha
14
16
23
25
26
28
47
106
120
129











Postemergence



















Barley
50
45
30
30
40
35
55
40
55
50



Bermudagrass
65
65
30
25
30
25
75
80
10
70



Blackgrass
85
80
25
60
90
60
90
60
85
80



Bromegrass, Downy
45
25
5
10
50
35
65
40
—
40



Canarygrass
85
90
15
55
90
90
90
80
90
85



Chickweed
80
100
70
98
100
100
—
98
100
98



Cocklebur
75
45
50
20
65
25
70
55
65
25



Corn
15
15
30
25
25
25
25
55
10
65



Crabgrass, Large
60
60
35
65
40
25
50
65
45
85



Cupgrass, Woolly
65
75
50
45
55
40
90
50
45
70



Deadnettle
100
100
98
100
100
100
100
90
100
100



Foxtail, Giant
35
50
25
60
60
50
98
55
55
65



Foxtail, Green
90
—
50
70
85
85
100
85
100
95



Galium
80
90
90
55
75
80
98
80
—
90



Goosegrass
75
10
30
40
70
45
75
55
45
55



Johnsongrass
75
45
20
15
40
10
50
55
45
70



Kochia
95
98
85
90
98
95
—
90
98
98



Lambsquarters
100
100
98
98
98
95
—
100
100
100



Morningglory
95
80
90
—
—
—
100
40
98
75



Nutsedge, Yellow
0
0
10
10
15
25
0
0
0
0



Oat, Wild
60
80
35
30
85
70
90
45
90
80



Pigweed
85
100
95
98
98
98
100
98
100
100



Ragweed
80
75
20
60
95
85
95
60
85
45



Ryegrass, Italian
40
20
15
5
35
30
85
30
30
60



Soybean
35
35
65
30
55
60
75
65
100
75



Surinam Grass
55
45
15
20
45
15
60
40
20
60



Velvetleaf
90
85
50
50
85
50
90
65
65
100



Wheat
45
30
30
30
35
20
50
—
35
40



Windgrass
95
50
15
40
80
50
100
85
—
100













Compounds





















250 g ai/ha
137
138
139
141
142
145
148
153
154
155
156
162
164
166










Postemergence





















Barley
35
60
40
30
45
45
45
—
—
—
—
—
—
—


Barnyardgrass
—
—
—
—
—
—
—
75
40
75
55
95
10
60


Bermudagrass
45
95
80
95
85
90
55
—
—
—
—
—
—
—


Blackgrass
60
45
70
75
90
70
80
90
70
90
85
90
15
60


Bromegrass, Downy
85
65
30
45
50
25
65
—
—
—
—
—
—
—


Canarygrass
75
90
80
80
100
90
95
—
—
—
—
—
—
—


Chickweed
98
98
100
100
98
100
98
95
95
100
98
100
45
90


Cocklebur
60
85
—
—
50
65
—
—
—
—
—
—
—
—


Corn
—
—
60
60
45
50
60
55
20
45
30
40
20
15


Crabgrass, Large
65
95
80
95
95
95
80
90
70
85
70
80
10
40


Cupgrass, Woolly
90
85
—
45
85
75
75
—
—
—
—
—
—
—


Deadnettle
95
100
100
100
100
100
100
—
—
—
—
—
—
—


Foxtail, Giant
50
95
75
80
90
85
75
95
75
100
50
98
35
40


Foxtail, Green
95
90
100
100
100
100
100
—
—
—
—
—
—
—


Galium
70
90
80
90
90
95
90
85
75
95
95
95
60
80


Goosegrass
—
80
80
60
90
80
40
—
—
—
—
—
—
—


Johnsongrass
90
95
80
15
80
75
98
90
85
98
85
98
10
20


Kochia
90
98
90
90
95
95
95
90
95
95
95
95
90
90


Lambsquarters
100
100
98
98
98
95
98
95
98
98
98
98
70
98


Morningglory
90
98
70
—
80
98
98
95
98
98
100
—
75
65


Nutsedge, Yellow
15
20
25
15
20
15
15
15
15
20
10
10
10
10


Oat, Wild
70
98
80
70
70
80
90
85
65
90
70
90
10
30


Oilseed Rape
—
—
—
—
—
—
—
95
95
95
95
95
25
40


Pigweed
100
100
98
98
98
98
98
98
98
100
100
95
80
98


Ragweed
85
85
75
85
75
70
85
85
40
85
80
95
60
75


Ryegrass, Italian
90
75
40
70
50
50
65
65
35
70
70
80
5
25


Soybean
60
80
45
65
55
60
90
85
75
80
95
95
50
35


Surinam Grass
45
—
40
30
50
75
30
—
—
—
—
—
—
—


Velvetleaf
70
90
75
60
75
60
85
95
65
80
80
85
40
30


Waterhemp
—
—
—
—
—
—
—
98
98
98
98
100
75
98


Wheat
35
35
40
20
45
40
40
30
30
40
30
25
10
10


Windgrass
90
80
—
60
95
90
100
—
—
—
—
—
—
—












Compounds


















250 g ai/ha
168
169
170
171
172
179
183
185
188
195
196










Postemergence


















Barley
—
—
—
—
—
—
—
—
—
35
50


Barnyardgrass
95
85
95
75
90
75
85
80
100
—
—


Bermudagrass
—
—
—
—
—
—
—
—
—
95
90


Blackgrass
80
50
70
30
60
60
60
50
90
80
80


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
60
80


Canarygrass
—
—
—
—
—
—
—
—
—
100
90


Chickweed
100
100
95
100
90
95
98
95
95
98
100


Cocklebur
—
—
—
—
—
—
—
—
—
50
75


Corn
45
30
30
15
30
15
30
25
35
80
65


Crabgrass, Large
95
80
90
55
95
80
85
80
95
95
95


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
75
90


Deadnettle
—
—
—
—
—
—
—
—
—
100
100


Foxtail, Giant
95
90
98
70
95
80
85
98
100
90
90


Foxtail, Green
—
—
—
—
—
—
—
—
—
100
100


Galium
95
95
90
80
90
90
90
90
90
95
95


Goosegrass
—
—
—
—
—
—
—
—
—
80
85


Johnsongrass
75
50
98
25
95
55
75
75
98
95
95


Kochia
90
90
90
90
90
90
95
90
90
95
90


Lambsquarters
95
98
98
95
98
90
98
95
98
95
95


Morningglory
90
100
100
—
80
90
100
100
—
95
75


Nutsedge, Yellow
20
10
10
10
15
10
10
15
15
25
20


Oat, Wild
60
50
90
20
80
50
85
60
90
85
90


Oilseed Rape
95
60
85
30
95
90
50
55
95
—
—


Pigweed
98
100
100
98
98
100
100
100
100
98
98


Ragweed
80
95
90
55
80
75
95
95
85
85
90


Ryegrass, Italian
80
40
70
10
40
40
40
35
90
60
85


Soybean
60
55
—
—
60
45
90
55
55
65
70


Surinam Grass
—
—
—
—
—
—
—
—
—
60
75


Velvetleaf
90
80
90
75
80
75
75
90
70
65
80


Waterhemp
95
95
100
98
98
95
100
100
100
—
—


Wheat
45
30
35
20
30
15
30
20
50
30
45


Windgrass
—
—
—
—
—
—
—
—
—
100
95












Compounds



















125 g ai/ha
14
15
16
23
25
26
28
47
106
120
124
129










Postemergence



















Barley
50
50
45
20
30
30
20
50
35
40
30
45


Bermudagrass
55
35
15
15
25
30
20
55
55
5
60
60


Blackgrass
60
80
40
20
40
70
55
60
45
60
85
70


Bromegrass, Downy
40
40
25
5
5
40
35
50
40
30
0
40


Canarygrass
85
85
60
15
30
90
60
85
70
60
85
50


Chickweed
75
75
100
60
98
100
95
—
95
100
55
80


Cocklebur
45
75
45
40
20
55
20
70
40
65
55
15


Corn
15
35
15
20
20
20
25
15
15
10
25
40


Crabgrass, Large
45
60
20
25
40
40
20
35
65
25
45
65


Cupgrass, Woolly
35
75
65
15
25
45
35
80
45
40
20
65


Deadnettle
100
100
98
85
90
98
90
100
90
100
98
100


Foxtail, Giant
30
75
50
15
55
45
35
80
55
50
45
30


Foxtail, Green
90
85
98
45
35
70
70
100
70
100
95
95


Galium
80
80
80
90
55
75
70
95
80
85
85
90


Goosegrass
60
65
10
15
25
40
25
70
45
10
65
30


Johnsongrass
55
80
45
10
10
25
5
35
40
25
45
15


Kochia
95
95
98
80
90
95
75
—
85
98
85
98


Lambsquarters
100
100
100
98
98
98
95
—
100
100
98
98


Morningglory
80
90
75
90
—
—
—
100
40
65
40
65


Nutsedge, Yellow
0
0
0
10
10
15
15
0
0
0
0
0


Oat, Wild
50
60
20
35
30
40
40
85
45
80
35
50


Pigweed
80
90
100
80
95
80
55
100
98
98
98
98


Ragweed
60
70
75
20
60
90
—
75
60
80
65
45


Ryegrass, Italian
35
60
20
10
5
30
25
75
20
5
65
30


Soybean
30
45
35
55
30
50
35
75
60
55
60
70


Surinam Grass
30
50
10
10
20
25
15
60
35
20
20
50


Velvetleaf
85
90
65
40
45
55
35
80
65
55
55
80


Wheat
40
35
25
15
30
30
10
45
30
35
20
30


Windgrass
95
90
50
15
40
80
50
85
80
90
98
85












Compounds





















125 g ai/ha
137
138
139
141
142
145
148
153
154
155
156
160
162
164










Postemergence





















Barley
30
35
35
15
40
35
40
—
—
—
—
—
—
—


Barnyardgrass
—
—
—
—
—
—
—
45
25
55
40
35
90
10


Bermudagrass
—
75
55
55
75
75
50
—
—
—
—
—
—
—


Blackgrass
35
40
70
35
80
70
70
70
55
85
75
65
85
15


Bromegrass, Downy
60
50
15
30
45
20
60
—
—
—
—
—
—
—


Canarygrass
70
70
60
50
85
50
95
—
—
—
—
—
—
—


Chickweed
98
95
98
98
98
98
90
95
95
95
95
98
100
45


Cocklebur
—
85
—
—
40
65
98
—
—
—
—
—
—
—


Corn
—
—
55
55
35
—
55
45
—
45
25
25
30
20


Crabgrass, Large
40
55
55
80
95
85
60
80
45
75
40
40
35
10


Cupgrass, Woolly
55
55
50
30
75
40
65
—
—
—
—
—
—
—


Deadnettle
95
100
98
100
100
100
100
—
—
—
—
—
—
—


Foxtail, Giant
—
55
40
45
80
50
35
90
55
75
25
75
65
20


Foxtail, Green
95
90
100
100
100
100
100
—
—
—
—
—
—
—


Galium
70
—
80
90
90
90
90
85
70
80
90
95
80
60


Goosegrass
65
50
60
50
70
70
25
—
—
—
—
—
—
—


Johnsongrass
80
45
80
15
80
70
55
60
65
98
65
30
80
10


Kochia
90
98
90
90
95
90
85
90
90
95
90
95
95
40


Lambsquarters
100
100
95
98
98
95
98
95
98
98
98
95
98
60


Morningglory
80
98
60
95
60
95
98
95
75
65
75
98
—
—


Nutsedge, Yellow
10
15
10
15
15
15
15
15
15
10
10
15
5
5


Oat, Wild
50
80
60
45
70
60
80
70
65
75
50
60
60
5


Oilseed Rape
—
—
—
—
—
—
—
90
95
95
95
95
90
20


Pigweed
100
98
98
98
98
98
98
98
98
98
95
98
90
80


Ragweed
75
85
45
—
75
70
85
80
30
85
75
40
85
—


Ryegrass, Italian
65
60
30
50
50
40
60
60
30
65
35
45
60
5


Soybean
55
80
45
55
55
55
80
70
65
80
95
30
75
—


Surinam Grass
45
65
35
30
45
60
25
—
—
—
—
—
—
—


Velvetleaf
55
80
70
60
55
50
80
65
55
75
60
75
60
40


Waterhemp
—
—
—
—
—
—
—
98
98
98
98
98
100
65


Wheat
30
35
40
20
40
30
40
30
20
35
25
25
25
10


Windgrass
70
55
80
55
85
90
98
—
—
—
—
—
—
—












Compounds



















125 g ai/ha
166
168
169
170
171
172
179
183
185
188
195
196










Postemergence



















Barley
—
—
—
—
—
—
—
—
—
—
35
45


Barnyardgrass
45
90
75
85
60
85
65
80
70
98
—
—


Bermudagrass
—
—
—
—
—
—
—
—
—
—
90
85


Blackgrass
40
80
35
60
10
60
55
60
50
85
80
80


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
50
70


Canarygrass
—
—
—
—
—
—
—
—
—
—
85
90


Chickweed
90
90
95
—
95
90
85
80
95
90
98
100


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
65


Corn
15
30
20
30
15
25
15
—
25
20
—
65


Crabgrass, Large
20
95
40
80
40
65
35
35
60
95
90
85


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
75
85


Deadnettle
—
—
—
—
—
—
—
—
—
—
100
100


Foxtail, Giant
40
95
65
98
55
80
55
65
90
98
75
90


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
100
100


Galium
60
90
90
90
80
90
90
90
90
85
95
90


Goosegrass
—
—
—
—
—
—
—
—
—
—
60
80


Johnsongrass
20
70
35
80
25
65
20
50
65
95
95
90


Kochia
90
90
90
90
90
90
90
90
90
90
90
90


Lambsquarters
95
95
98
95
95
98
85
95
85
98
95
95


Morningglory
35
90
100
100
98
—
80
100
100
100
90
75


Nutsedge, Yellow
5
15
10
5
10
15
10
10
10
10
25
15


Oat, Wild
—
50
30
85
10
45
35
55
55
60
80
85


Oilseed Rape
5
90
40
50
30
90
90
25
50
90
—
—


Pigweed
95
98
100
100
90
98
98
100
100
98
98
98


Ragweed
25
65
85
90
55
80
60
90
95
85
70
90


Ryegrass, Italian
20
60
25
35
10
35
25
20
25
85
60
85


Soybean
35
60
50
90
40
60
45
55
45
50
65
65


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
70


Velvetleaf
20
80
75
85
45
75
75
75
85
70
60
75


Waterhemp
98
95
80
98
75
98
95
100
95
100
—
—


Wheat
5
35
30
35
20
25
15
20
15
45
25
45


Windgrass
—
—
—
—
—
—
—
—
—
—
95
95












Compounds



















62 g ai/ha
14
15
16
23
25
26
28
47
106
120
124
129










Postemergence



















Barley
35
35
35
15
25
30
15
45
25
30
30
35


Bermudagrass
15
15
5
10
20
20
15
20
40
5
45
45


Blackgrass
40
60
25
20
35
35
10
45
40
30
50
60


Bromegrass, Downy
40
35
15
5
5
30
25
30
35
15
0
35


Canarygrass
80
85
60
10
10
45
50
75
50
35
35
45


Chickweed
75
70
98
55
60
98
55
—
70
100
55
45


Cocklebur
5
60
45
25
20
15
15
65
35
50
20
10


Corn
10
15
15
15
20
20
20
15
15
10
25
15


Crabgrass, Large
45
45
5
15
20
30
15
15
55
25
40
45


Cupgrass, Woolly
5
5
20
10
25
40
30
65
45
10
10
65


Deadnettle
98
100
98
80
55
98
80
100
80
100
98
100


Foxtail, Giant
15
10
40
15
45
30
35
65
40
45
25
20


Foxtail, Green
—
85
98
30
35
40
70
98
50
85
90
95


Galium
80
55
65
85
50
55
55
80
65
80
80
85


Goosegrass
5
40
5
10
20
30
20
35
35
5
55
25


Johnsongrass
20
60
0
10
5
15
5
10
15
5
40
15


Kochia
95
95
98
75
80
95
65
—
85
95
80
95


Lambsquarters
100
100
100
40
80
95
35
—
100
100
98
98


Morningglory
80
75
75
70
—
—
—
95
20
60
40
55


Nutsedge, Yellow
0
0
0
10
5
10
5
0
0
0
0
0


Oat, Wild
45
55
10
10
5
30
15
—
30
60
25
35


Pigweed
60
70
95
—
95
60
55
100
98
98
95
98


Ragweed
55
60
25
10
50
55
60
65
55
60
65
40


Ryegrass, Italian
35
45
10
10
5
20
25
65
5
5
35
15


Soybean
25
35
25
55
30
40
35
70
15
25
55
40


Surinam Grass
5
15
5
10
15
20
10
10
25
5
15
45


Velvetleaf
80
60
65
25
15
50
25
70
45
45
50
45


Wheat
35
35
20
10
20
20
10
35
30
10
15
25


Windgrass
90
85
50
15
35
55
45
80
65
55
95
80












Compounds





















62 g ai/ha
137
138
139
141
142
145
148
153
154
155
156
160
162
164










Postemergence





















Barley
10
30
10
10
35
20
35
—
—
—
—
—
—
—


Barnyardgrass
—
—
—
—
—
—
—
35
25
35
30
30
65
10


Bermudagrass
30
45
40
—
70
40
30
—
—
—
—
—
—
—


Blackgrass
30
40
40
20
60
60
50
60
35
70
60
45
80
5


Bromegrass, Downy
30
45
10
30
45
10
55
—
—
—
—
—
—
—


Canarygrass
60
55
45
25
80
40
60
—
—
—
—
—
—
—


Chickweed
80
80
98
90
98
85
75
95
85
70
95
95
100
40


Cocklebur
50
70
—
—
30
15
98
—
—
—
—
—
—
—


Corn
—
—
25
45
35
45
30
25
20
25
15
20
30
15


Crabgrass, Large
40
50
45
55
80
50
60
55
30
45
30
35
35
5


Cupgrass, Woolly
50
55
30
20
40
25
55
—
—
—
—
—
—
—


Deadnettle
95
100
95
100
100
100
95
—
—
—
—
—
—
—


Foxtail, Giant
40
55
30
20
75
20
35
80
20
45
15
—
55
20


Foxtail, Green
85
85
95
100
100
100
98
—
—
—
—
—
—
—


Galium
70
90
70
85
80
80
90
65
60
75
90
85
75
30


Goosegrass
25
25
40
40
35
35
15
—
—
—
—
—
—
—


Johnsongrass
40
45
50
10
70
20
20
—
30
80
50
—
80
10


Kochia
90
95
85
90
90
85
85
90
90
90
90
95
90
40


Lambsquarters
100
100
95
98
98
95
98
95
98
95
98
95
95
55


Morningglory
60
90
60
85
—
90
98
80
75
65
70
98
—
60


Nutsedge, Yellow
10
10
10
10
5
10
10
10
10
10
10
10
5
5


Oat, Wild
50
60
50
15
45
40
45
50
35
45
50
45
60
5


Oilseed Rape
—
—
—
—
—
—
—
90
90
90
90
95
90
5


Pigweed
100
98
98
95
98
98
98
95
95
90
90
98
85
75


Ragweed
—
80
40
70
70
—
85
55
30
—
75
40
—
50


Ryegrass, Italian
55
55
30
30
40
30
35
35
10
45
35
30
35
5


Soybean
55
70
40
55
55
50
45
70
60
75
80
25
70
40


Surinam Grass
45
50
35
15
40
30
20
—
—
—
—
—
—
—


Velvetleaf
55
75
35
55
50
35
50
60
45
60
50
50
55
30


Waterhemp
—
—
—
—
—
—
—
98
98
98
98
98
100
65


Wheat
15
10
10
15
25
15
25
30
15
30
15
25
20
10


Windgrass
50
50
70
50
80
70
80
—
—
—
—
—
—
—












Compounds



















62 g ai/ha
166
168
169
170
171
172
179
183
185
188
195
196










Postemergence



















Barley
—
—
—
—
—
—
—
—
—
—
20
40


Barnyardgrass
25
75
25
55
15
45
45
35
35
95
—
—


Bermudagrass
—
—
—
—
—
—
—
—
—
—
60
80


Blackgrass
20
45
15
10
10
25
50
20
40
55
70
80


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
30
50


Canarygrass
—
—
—
—
—
—
—
—
—
—
60
90


Chickweed
90
80
60
95
70
85
80
75
85
90
95
98


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
60


Corn
15
15
15
25
15
20
15
20
20
20
75
60


Crabgrass, Large
15
65
35
30
20
55
20
35
40
85
60
85


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
65
80


Deadnettle
—
—
—
—
—
—
—
—
—
—
100
100


Foxtail, Giant
40
65
65
80
35
35
40
45
80
98
35
85


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
100
100


Galium
50
90
90
90
75
90
90
70
80
80
95
85


Goosegrass
—
—
—
—
—
—
—
—
—
—
50
75


Johnsongrass
15
55
30
25
15
60
20
30
30
75
80
90


Kochia
90
90
90
90
90
90
90
90
90
90
85
90


Lambsquarters
95
95
90
95
75
98
80
95
80
95
95
95


Morningglory
30
80
—
98
65
80
80
98
98
100
90
75


Nutsedge, Yellow
5
10
5
5
5
10
5
10
10
10
20
10


Oat, Wild
20
45
25
65
5
20
20
40
30
60
75
85


Oilseed Rape
5
70
40
50
20
90
40
25
50
90
—
—


Pigweed
85
98
95
100
90
98
98
—
98
95
95
98


Ragweed
15
65
60
85
55
75
55
80
90
75
50
85


Ryegrass, Italian
5
35
10
35
5
20
15
15
10
70
55
60


Soybean
35
35
30
70
35
45
35
55
45
50
40
50


Surinam Grass
—
—
—
—
—
—
—
—
—
—
50
70


Velvetleaf
20
75
65
85
25
65
75
—
80
65
50
65


Waterhemp
—
90
80
98
75
95
90
100
90
100
—
—


Wheat
5
20
10
20
10
20
10
20
15
30
20
35


Windgrass
—
—
—
—
—
—
—
—
—
—
80
80












Compounds



















31 g ai/ha
14
15
16
23
25
26
28
47
106
120
124
129










Postemergence



















Barley
30
35
115
5
20
20
10
35
15
20
15
30


Bermudagrass
0
5
5
5
15
20
10
10
40
5
25
40


Blackgrass
15
30
10
15
10
30
10
40
30
25
35
40


Bromegrass, Downy
30
25
15
5
5
15
5
10
30
15
0
35


Canarygrass
55
60
20
5
5
40
30
60
35
25
20
30


Chickweed
60
55
85
30
30
40
30
80
60
75
50
15


Cocklebur
5
5
35
25
15
10
10
10
35
45
15
5


Corn
5
5
5
10
20
20
15
5
10
5
20
10


Crabgrass, Large
10
15
5
10
15
20
10
5
40
5
30
20


Cupgrass, Woolly
5
5
5
10
25
25
20
55
5
10
5
35


Deadnettle
98
100
50
80
50
98
40
95
75
100
80
100


Foxtail, Giant
10
10
40
15
35
25
35
65
40
5
15
0


Foxtail, Green
70
40
30
—
35
30
30
20
50
15
70
85


Galium
60
55
60
85
50
50
40
80
65
80
70
60


Goosegrass
5
25
5
10
15
25
20
5
10
5
45
15


Johnsongrass
20
45
0
5
5
15
5
0
0
0
5
5


Kochia
90
95
95
65
75
75
40
65
85
65
80
95


Lambsquarters
100
100
95
40
70
80
35
100
80
100
95
98


Morningglory
75
75
50
70
—
—
—
75
0
60
15
50


Nutsedge, Yellow
0
0
0
10
5
10
5
0
0
0
0
0


Oat, Wild
25
45
5
5
5
10
10
35
10
55
20
20


Pigweed
45
60
75
70
85
—
55
100
95
95
90
85


Ragweed
55
60
5
10
50
40
35
45
10
60
50
40


Ryegrass, Italian
30
30
10
5
5
10
10
35
5
5
15
5


Soybean
25
10
20
30
25
35
30
40
10
25
55
20


Surinam Grass
5
10
5
5
10
15
5
5
20
5
10
45


Velvetleaf
75
60
10
15
15
25
20
65
5
20
45
45


Wheat
30
25
5
10
10
10
5
15
10
10
10
20


Windgrass
70
20
45
10
30
40
30
60
50
50
80
60












Compounds





















31 g ai/ha
137
138
139
141
142
145
148
153
154
155
156
160
162
164










Postemergence





















Barley
10
10
5
5
20
15
35
—
—
—
—
—
—
—


Barnyardgrass
—
—
—
—
—
—
—
20
15
25
20
20
20
5


Bermudagrass
30
20
35
15
15
10
10
—
—
—
—
—
—
—


Blackgrass
10
20
35
20
55
10
40
55
15
40
50
35
45
5


Bromegrass, Downy
10
40
5
25
25
5
45
—
—
—
—
—
—
—


Canarygrass
45
30
40
20
45
15
40
—
—
—
—
—
—
—


Chickweed
70
—
75
80
85
75
75
95
85
50
95
90
100
10


Cocklebur
45
65
—
5
—
10
85
—
—
—
—
—
—
—


Corn
—
—
—
45
30
35
25
20
20
25
—
15
15
15


Crabgrass, Large
15
45
40
20
65
25
15
50
20
20
10
25
20
5


Cupgrass, Woolly
45
50
15
15
40
20
55
—
—
—
—
—
—
—


Deadnettle
80
98
95
100
100
100
95
—
—
—
—
—
—
—


Foxtail, Giant
10
20
15
10
20
15
10
45
20
15
10
20
45
10


Foxtail, Green
80
35
95
100
100
98
80
—
—
—
—
—
—
—


Galium
45
85
60
85
80
80
80
60
45
70
80
80
75
30


Goosegrass
20
5
15
35
35
25
—
—
—
—
—
—
—
—


Johnsongrass
5
45
30
10
55
10
20
40
10
20
45
15
45
10


Kochia
90
95
85
85
80
85
80
90
90
90
90
90
90
40


Lambsquarters
100
100
90
98
80
95
98
95
75
80
98
80
95
50


Morningglory
—
90
55
85
60
90
70
40
40
55
65
60
—
50


Nutsedge, Yellow
5
10
10
0
5
5
10
10
10
5
5
10
5
0


Oat, Wild
45
55
40
10
35
20
15
35
15
40
35
30
40
5


Oilseed Rape
—
—
—
—
—
—
—
90
80
90
80
95
90
5


Pigweed
98
98
95
95
98
85
65
95
95
90
75
95
85
50


Ragweed
65
75
—
60
65
60
65
55
30
80
75
10
85
50


Ryegrass, Italian
35
40
25
15
10
20
10
30
5
35
15
30
30
5


Soybean
40
55
40
40
50
50
45
55
45
50
55
25
70
30


Surinam Grass
40
45
10
15
40
25
20
—
—
—
—
—
—
—


Velvetleaf
35
50
20
40
30
35
50
50
35
50
45
30
35
25


Waterhemp
—
—
—
—
—
—
—
98
90
98
98
95
98
35


Wheat
10
10
10
10
15
5
20
10
10
15
5
5
20
5


Windgrass
40
50
50
50
80
50
60
—
—
—
—
—
—
—












Compounds



















31 g ai/ha
166
168
169
170
171
172
179
183
185
188
195
196










Postemergence



















Barley
—
—
—
—
—
—
—
—
—
—
15
30


Barnyardgrass
10
40
15
20
10
40
40
15
30
75
—
—


Bermudagrass
—
—
—
—
—
—
—
—
—
—
40
80


Blackgrass
10
45
5
10
5
10
30
10
20
55
45
70


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
15
50


Canarygrass
—
—
—
—
—
—
—
—
—
—
40
80


Chickweed
55
80
60
75
50
65
75
75
70
80
95
98


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
55


Corn
15
15
10
15
15
20
15
10
15
10
60
60


Crabgrass, Large
15
30
35
30
15
20
20
25
25
50
55
80


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
50
30


Deadnettle
—
—
—
—
—
—
—
—
—
—
100
100


Foxtail, Giant
20
55
20
55
25
35
35
45
40
98
35
85


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
100
100


Galium
50
90
80
80
70
90
90
70
70
60
80
80


Goosegrass
—
—
—
—
—
—
—
—
—
—
50
75


Johnsongrass
10
30
15
20
15
35
10
20
10
45
55
80


Kochia
90
90
85
90
90
90
80
90
90
70
75
85


Lambsquarters
60
80
90
85
75
98
80
85
80
90
95
95


Morningglory
30
50
98
75
60
65
65
98
90
70
65
75


Nutsedge, Yellow
0
10
5
5
5
10
5
10
10
10
10
10


Oat, Wild
15
30
5
30
5
15
10
30
25
45
60
55


Oilseed Rape
5
40
30
30
5
50
30
20
10
40
—
—


Pigweed
35
80
95
100
70
98
95
100
98
95
95
98


Ragweed
15
65
40
85
55
75
50
65
75
65
—
70


Ryegrass, Italian
5
10
10
15
5
10
10
10
10
50
25
35


Soybean
35
30
30
30
25
35
30
35
40
40
40
45


Surinam Grass
—
—
—
—
—
—
—
—
—
—
30
35


Velvetleaf
10
60
50
75
25
65
55
75
55
50
45
55


Waterhemp
90
80
75
85
70
90
80
85
90
70
—
—


Wheat
5
20
10
10
5
10
5
10
5
20
10
15


Windgrass
—
—
—
—
—
—
—
—
—
—
55
80















Compounds

Compounds















16 g ai/ha
15
124
16 g ai/ha
15
124











Postemergence














Barley
30
5
Goosegrass
5
25



Bermudagrass
5
5
Johnsongrass
0
5



Blackgrass
20
0
Kochia
90
75



Bromegrass, Downy
10
0
Lambsquarters
100
85



Canarygrass
35
0
Morningglory
45
15



Chickweed
55
45
Nutsedge, Yellow
0
0



Cocklebur
—
10
Oat, Wild
40
20



Corn
0
5
Pigweed
5
75



Crabgrass, Large
5
20
Ragweed
45
45



Cupgrass, Woolly
5
5
Ryegrass, Italian
10
5



Deadnettle
90
75
Soybean
10
45



Foxtail, Giant
5
15
Surinam Grass
5
5



Foxtail, Green
30
65
Velvetleaf
60
45



Galium
50
70
Wheat
15
5



Goosegrass
5
25
Windgrass
20
50

















Compound

Compound



16 g ai/ha
160
16 g ai/ha
160











Postemergence












Barnyardgrass
15
Nutsedge, Yellow
5



Blackgrass
25
Oat, Wild
15



Chickweed
70
Oilseed Rape
85



Corn
15
Pigweed
95



Crabgrass, Large
20
Ragweed
10



Foxtail, Giant
15
Ryegrass, Italian
10



Galium
55
Soybean
15



Johnsongrass
10
Velvetleaf
20



Kochia
90
Waterhemp
95



Lambsquarters
70
Wheat
5



Morningglory
60













Compounds


















250 g ai/ha
14
16
23
25
26
47
106
120
129











Preemergence


















Bermudagrass
100
75
100
100
100
100
100
100
98



Blackgrass
98
100
100
100
90
100
95
90
90



Bromegrass, Downy
98
100
10
80
85
100
60
90
100



Cocklebur
45
—
5
30
55
5
—
5
0



Corn
10
—
85
10
5
40
10
50
65



Crabgrass, Large
100
—
100
100
100
100
100
100
100



Cupgrass, Woolly
80
—
100
98
90
98
90
98
98



Foxtail, Giant
100
—
100
100
100
100
100
100
98



Foxtail, Green
100
100
100
95
95
100
95
90
90



Galium
100
100
100
98
100
100
90
100
100



Goosegrass
100
—
100
100
100
100
100
98
98



Johnsongrass
85
—
98
98
98
95
85
98
95



Kochia
85
—
100
85
98
98
65
100
95



Lambsquarters
100
—
100
98
100
100
100
100
100



Morningglory
65
—
100
—
—
65
60
90
65



Nightshade
98
—
98
95
98
98
100
95
95



Nutsedge, Yellow
0
—
55
0
0
0
0
0
5



Oat, Wild
90
100
100
90
95
100
80
95
95



Pigweed
100
—
100
100
100
100
100
100
100



Ragweed
—
—
60
50
75
80
55
65
55



Russian Thistle
95
100
—
90
95
100
100
100
—



Ryegrass, Italian
85
100
70
90
80
98
50
95
95



Soybean
0
—
50
10
15
35
5
20
40



Sunflower
15
—
0
0
15
10
0
5
0



Surinam Grass
85
—
100
100
90
65
90
100
98



Velvetleaf
75
—
100
70
100
100
10
100
95



Wheat
45
45
35
35
30
40
5
50
60













Compounds





















250 g ai/ha
138
139
142
145
146
147
148
153
154
155
156
162
163
164










Preemergence





















Barnyardgrass
—
—
—
—
—
—
—
100
100
100
100
100
100
70


Bermudagrass
100
100
98
98
98
100
100
—
—
—
—
—
—
—


Blackgrass
95
90
90
90
90
90
90
90
90
90
90
95
95
70


Bromegrass, Downy
80
85
90
85
80
90
80
—
—
—
—
—
—
—


Cocklebur
15
5
—
—
0
—
—
—
—
—
—
—
—
—


Corn
55
30
30
60
25
35
45
35
15
45
30
35
10
10


Crabgrass, Large
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Cupgrass, Woolly
100
90
98
98
100
98
98
—
—
—
—
—
—
—


Foxtail, Giant
100
100
100
100
100
100
100
100
100
100
95
100
100
100


Foxtail, Green
95
90
90
90
90
95
95
—
—
—
—
—
—
—


Galium
100
95
100
100
100
100
100
100
100
100
100
100
75
80


Goosegrass
100
100
100
100
100
100
100
—
—
—
—
—
—
—


Johnsongrass
100
100
100
100
100
98
98
98
95
95
95
98
60
40


Kochia
90
100
100
98
85
85
95
—
—
—
—
—
—
—


Lambsquarters
98
90
98
98
95
80
85
100
100
100
100
—
—
95


Morningglory
98
55
—
85
90
35
75
50
25
90
30
85
75
45


Nightshade
98
98
98
90
98
98
85
—
—
—
—
—
—
—


Nutsedge, Yellow
5
5
0
10
10
15
—
—
—
—
0
5
75
0


Oat, Wild
95
85
90
90
90
95
85
—
—
—
—
—
—
—


Oilseed Rape
—
—
—
—
—
—
—
98
100
100
98
100
95
30


Pigweed
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Ragweed
50
55
80
55
45
80
70
80
70
95
60
95
35
30


Russian Thistle
100
5
90
95
95
90
95
—
—
—
—
—
—
—


Ryegrass, Italian
90
90
90
90
90
95
90
90
90
90
90
95
85
75


Soybean
30
25
20
10
40
35
30
35
15
40
25
25
20
5


Sunflower
30
10
25
25
35
25
10
—
—
—
—
—
—
—


Surinam Grass
100
98
98
100
100
95
100
—
—
—
—
—
—
—


Velvetleaf
98
40
100
85
60
100
80
100
100
100
100
100
75
70


Waterhemp
—
—
—
—
—
—
—
100
100
100
100
100
100
—


Wheat
50
20
50
50
10
45
35
60
55
35
35
35
0
5












Compounds




















250 g ai/ha
166
168
169
170
171
172
174
179
183
185
188
195
196










Preemergence




















Barnyardgrass
100
100
100
100
98
100
98
100
100
100
100
—
—


Bermudagrass
—
—
—
—
—
—
—
—
—
—
—
98
100


Blackgrass
95
98
95
100
100
95
100
100
100
98
100
90
90


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
—
90
100


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
—
75


Corn
20
55
20
60
25
40
10
20
40
35
20
35
50


Crabgrass, Large
100
100
100
100
100
100
100
100
100
100
100
100
100


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
—
98
100


Foxtail, Giant
100
100
100
100
100
100
100
100
100
100
100
100
100


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
—
90
90


Galium
100
100
100
100
100
100
100
100
100
100
95
95
100


Goosegrass
—
—
—
—
—
—
—
—
—
—
—
100
100


Johnsongrass
100
100
98
95
95
98
95
100
95
100
98
100
100


Kochia
—
—
—
—
—
—
—
—
—
—
—
95
98


Lambsquarters
—
98
90
98
100
95
90
100
100
100
100
95
95


Morningglory
45
80
85
100
25
70
55
65
95
100
100
90
100


Nightshade
—
—
—
—
—
—
—
—
—
—
—
98
100


Nutsedge, Yellow
15
5
5
5
0
5
0
5
5
5
20
80
10


Oat, Wild
—
—
—
—
—
—
—
—
—
—
—
90
90


Oilseed Rape
100
100
100
100
90
100
50
100
100
100
100
—
—


Pigweed
100
100
100
100
100
100
100
100
100
100
100
100
98


Ragweed
55
80
65
95
15
85
55
45
95
95
—
55
90


Russian Thistle
—
—
—
—
—
—
—
—
—
—
—
90
90


Ryegrass, Italian
100
100
95
95
100
100
95
95
95
100
98
90
90


Soybean
35
35
30
45
—
35
10
25
30
40
65
25
35


Sunflower
—
—
—
—
—
—
—
—
—
—
—
20
40


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
98
100


Velvetleaf
60
100
100
100
65
100
100
80
100
100
90
90
100


Waterhemp
100
—
—
—
—
—
—
—
—
—
100
—
—


Wheat
15
60
50
60
45
45
40
55
40
55
40
30
50













Compounds




















125 g ai/ha
14
15
16
23
25
26
47
106
120
129











Preemergence



















Bermudagrass
100
100
75
100
98
100
100
100
98
98



Blackgrass
85
95
100
100
95
90
100
90
90
90



Bromegrass, Downy
60
80
50
5
40
50
90
40
90
95



Cocklebur
20
65
—
5
0
15
0
—
—
0



Corn
5
10
—
70
5
5
10
0
25
45



Crabgrass, Large
100
100
—
100
100
100
100
100
100
100



Cupgrass, Woolly
75
95
—
100
65
70
95
80
98
98



Foxtail, Giant
100
100
—
100
100
100
100
100
98
98



Foxtail, Green
100
100
100
100
95
95
100
95
90
90



Galium
100
98
100
100
80
100
100
60
100
100



Goosegrass
100
100
—
100
100
100
100
98
98
98



Johnsongrass
80
90
—
95
65
95
60
75
95
85



Kochia
75
85
—
95
55
95
98
45
100
90



Lambsquarters
100
100
—
98
98
98
100
100
100
98



Morningglory
55
45
—
100
—
—
50
10
45
60



Nightshade
95
90
—
95
95
98
98
90
95
90



Nutsedge, Yellow
0
10
—
35
0
0
0
0
0
0



Oat, Wild
70
70
100
80
80
70
90
70
95
95



Pigweed
100
100
—
100
100
100
100
100
100
100



Ragweed
—
—
—
20
20
50
45
0
45
0



Russian Thistle
95
100
100
—
90
95
100
30
85
—



Ryegrass, Italian
60
80
100
25
45
60
90
45
90
90



Soybean
0
25
—
10
0
5
5
5
10
10



Sunflower
0
25
—
0
0
10
0
0
0
0



Surinam Grass
60
90
—
100
55
65
65
80
98
98



Velvetleaf
70
80
—
80
15
75
90
0
35
45



Wheat
35
50
15
20
10
30
35
0
40
30













Compounds





















125 g ai/ha
138
139
142
145
146
147
148
153
154
155
156
160
162
163










Preemergence





















Barnyardgrass
—
—
—
—
—
—
—
100
90
98
90
100
100
75


Bermudagrass
100
100
98
98
98
100
100
—
—
—
—
—
—
—


Blackgrass
95
90
90
90
90
90
90
90
90
90
90
90
90
90


Bromegrass, Downy
60
—
90
70
15
85
50
—
—
—
—
—
—
—


Cocklebur
15
0
10
10
0
—
—
—
—
—
—
—
—
—


Corn
40
10
20
25
15
25
15
25
10
10
10
5
20
—


Crabgrass, Large
100
100
100
100
100
100
100
100
100
100
98
100
100
100


Cupgrass, Woolly
95
75
95
95
90
95
95
—
—
—
—
—
—
—


Foxtail, Giant
100
100
100
100
100
100
100
100
100
100
90
100
100
80


Foxtail, Green
95
—
90
90
90
95
95
—
—
—
—
—
—
—


Galium
100
85
100
100
95
100
100
100
85
100
100
100
100
5


Goosegrass
100
100
100
100
100
100
98
—
—
—
—
—
—
—


Johnsongrass
98
100
100
100
98
95
98
95
90
90
90
100
98
60


Kochia
85
90
98
98
85
80
90
—
—
—
—
—
—
—


Lambsquarters
98
85
95
95
85
80
65
100
100
100
100
100
—
—


Morningglory
65
35
—
70
45
—
55
50
5
60
10
20
80
30


Nightshade
98
85
98
85
90
98
85
—
—
—
—
—
—
—


Nutsedge, Yellow
5
0
0
5
—
0
5
5
—
—
0
0
5
20


Oat, Wild
95
—
85
90
85
85
85
—
—
—
—
—
—
—


Oilseed Rape
—
—
—
—
—
—
—
98
90
90
90
80
100
80


Pigweed
100
100
100
98
100
100
100
100
100
100
100
100
100
100


Ragweed
50
30
70
40
45
70
55
80
50
85
30
5
80
20


Russian Thistle
90
—
90
90
80
90
95
—
—
—
—
—
—
—


Ryegrass, Italian
70
—
90
90
55
85
60
90
90
85
90
90
90
65


Soybean
—
25
5
5
—
20
20
35
15
35
25
20
—
10


Sunflower
30
5
15
20
30
15
10
—
—
—
—
—
—
—


Surinam Grass
85
85
98
100
100
95
75
—
—
—
—
—
—
—


Velvetleaf
55
40
80
75
15
60
70
95
90
85
40
30
100
20


Waterhemp
—
—
—
—
—
—
—
100
100
100
100
100
100
100


Wheat
10
10
35
5
0
30
30
60
5
10
20
40
20
0












Compounds





















125 g ai/ha
164
166
168
169
170
171
172
174
179
183
185
188
189
195










Preemergence





















Barnyardgrass
25
98
100
98
100
95
100
98
100
100
100
100
100
—


Bermudagrass
—
—
—
—
—
—
—
—
—
—
—
—
—
98


Blackgrass
60
90
95
95
100
100
95
85
100
95
95
100
100
90


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
—
—
—
85


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
—
—
0


Corn
10
5
25
10
15
5
15
5
20
40
35
10
20
15


Crabgrass, Large
98
100
100
100
100
100
100
100
100
100
100
100
100
100


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
—
—
—
95


Foxtail, Giant
98
100
100
100
100
100
100
100
100
100
100
100
100
100


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
—
—
—
90


Galium
80
90
100
100
100
98
100
80
100
100
100
95
95
90


Goosegrass
—
—
—
—
—
—
—
—
—
—
—
—
—
100


Johnsongrass
20
75
100
95
95
75
95
50
95
80
80
95
85
98


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Lambsquarters
95
—
98
90
98
—
95
90
98
100
100
98
90
90


Morningglory
25
25
55
80
100
25
55
15
55
70
70
85
60
75


Nightshade
—
—
—
—
—
—
—
—
—
—
—
—
—
95


Nutsedge, Yellow
0
5
5
5
—
0
5
0
0
5
0
5
0
5


Oat, Wild
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Oilseed Rape
—
90
100
100
100
50
98
50
100
100
100
100
85
—


Pigweed
90
100
100
100
100
100
100
100
100
100
100
100
100
100


Ragweed
25
25
80
30
75
10
80
55
45
95
95
—
—
20


Russian Thistle
—
—
—
—
—
—
—
—
—
—
—
—
—
90


Ryegrass, Italian
55
50
100
90
95
60
100
90
95
90
100
95
100
90


Soybean
5
20
10
10
20
5
10
10
10
10
40
—
25
0


Sunflower
—
—
—
—
—
—
—
—
—
—
—
—
—
15


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
—
—
85


Velvetleaf
30
15
100
75
100
55
100
65
80
100
100
85
60
55


Waterhemp
—
100
—
—
—
—
—
—
—
—
—
100
100
—


Wheat
0
5
40
20
60
5
45
20
50
35
40
35
30
5
















Compound

Compound



125 g ai/ha
196
62 g ai/ha
196











Preemergence












Barnyardgrass
—
Barnyardgrass
—



Bermudagrass
100
Bermudagrass
98



Blackgrass
90
Blackgrass
90



Bromegrass, Downy
100
Bromegrass, Downy
95



Cocklebur
45
Cocklebur
—



Corn
45
Corn
35



Crabgrass, Large
100
Crabgrass, Large
100



Cupgrass, Woolly
100
Cupgrass, Woolly
98



Foxtail, Giant
100
Foxtail, Giant
100



Foxtail, Green
90
Foxtail, Green
90



Galium
98
Galium
95



Goosegrass
100
Goosegrass
100



Johnsongrass
—
Johnsongrass
100



Kochia
98
Kochia
98



Lambsquarters
95
Lambsquarters
90



Morningglory
100
Morningglory
85



Nightshade
100
Nightshade
100



Nutsedge, Yellow
5
Nutsedge, Yellow
0



Oat, Wild
90
Oat, Wild
90



Oilseed Rape
—
Oilseed Rape
—



Pigweed
98
Pigweed
98



Ragweed
80
Ragweed
60



Russian Thistle
90
Russian Thistle
90



Ryegrass, Italian
90
Ryegrass, Italian
90



Soybean
30
Soybean
15



Sunflower
30
Sunflower
20



Surinam Grass
100
Surinam Grass
98



Velvetleaf
80
Velvetleaf
70



Waterhemp
—
Waterhemp
—



Wheat
40
Wheat
15














Compounds




















62 g ai/ha
14
15
16
23
25
26
47
106
120
129











Preemergence



















Bermudagrass
100
100
25
100
98
100
100
100
98
98



Blackgrass
40
85
100
85
85
90
98
50
90
90



Bromegrass, Downy
35
30
10
0
5
45
40
5
85
80



Cocklebur
—
—
—
0
0
5
0
—
0
0



Corn
0
0
—
30
0
5
5
0
5
10



Crabgrass, Large
100
100
—
100
100
98
98
100
100
100



Cupgrass, Woolly
75
85
—
100
40
65
80
60
95
95



Foxtail, Giant
98
100
—
100
100
100
100
85
98
98



Foxtail, Green
100
100
100
100
95
95
100
95
90
90



Galium
90
95
100
95
15
75
100
10
100
100



Goosegrass
100
100
—
100
100
100
100
98
98
98



Johnsongrass
45
85
—
75
30
55
10
20
80
75



Kochia
0
70
—
95
40
95
90
0
90
90



Lambsquarters
100
100
—
98
90
98
100
100
100
95



Morningglory
10
15
—
20
—
—
20
0
45
20



Nightshade
80
85
—
90
45
90
98
75
95
90



Nutsedge, Yellow
0
0
—
10
0
0
0
0
0
0



Oat, Wild
40
70
100
80
30
70
90
45
90
85



Pigweed
100
100
—
100
100
100
100
98
100
100



Ragweed
—
—
—
20
5
35
15
0
45
0



Russian Thistle
90
95
100
—
—
80
100
5
—
—



Ryegrass, Italian
35
45
95
5
35
60
50
20
90
90



Soybean
0
0
—
5
0
5
0
0
5
0



Sunflower
0
0
—
0
0
—
0
0
0
0



Surinam Grass
45
55
—
60
20
50
20
20
95
95



Velvetleaf
10
20
—
25
5
35
60
0
15
10



Wheat
15
25
5
0
5
5
5
0
25
20













Compounds





















62 g ai/ha
138
139
142
145
146
147
148
153
154
155
156
160
162
163










Preemergence





















Barnyardgrass
—
—
—
—
—
—
—
90
90
90
90
90
100
25


Bermudagrass
100
100
98
98
98
100
100
—
—
—
—
—
—
—


Blackgrass
95
90
90
90
70
85
85
90
90
90
90
90
90
85


Bromegrass, Downy
30
20
60
20
0
45
40
—
—
—
—
—
—
—


Cocklebur
5
0
10
0
0
—
—
—
—
—
—
—
—
—


Corn
30
0
5
10
0
10
10
25
5
5
5
5
20
10


Crabgrass, Large
100
100
100
100
100
100
100
100
100
100
90
100
100
100


Cupgrass, Woolly
90
40
70
90
45
55
90
—
—
—
—
—
—
—


Foxtail, Giant
100
100
100
100
100
98
100
100
100
100
90
100
100
60


Foxtail, Green
95
90
90
90
90
95
95
—
—
—
—
—
—
—


Galium
100
80
80
98
95
100
100
98
85
100
100
100
—
5


Goosegrass
100
100
100
100
85
100
95
—
—
—
—
—
—
—


Johnsongrass
85
45
98
35
75
55
80
90
40
90
90
100
60
35


Kochia
65
75
80
90
55
40
40
—
—
—
—
—
—
—


Lambsquarters
98
70
90
85
40
45
25
100
100
100
100
100
—
—


Morningglory
55
15
35
20
40
30
20
30
5
40
10
15
60
25


Nightshade
95
75
95
80
35
98
60
—
—
—
—
—
—
—


Nutsedge, Yellow
—
0
—
—
0
0
5
0
—
—
0
0
0
0


Oat, Wild
85
50
85
70
40
70
85
—
—
—
—
—
—
—


Oilseed Rape
—
—
—
—
—
—
—
95
90
90
60
80
100
50


Pigweed
100
98
98
98
90
100
100
100
100
100
100
100
100
98


Ragweed
45
0
40
10
0
40
45
10
0
40
10
5
75
10


Russian Thistle
90
—
80
—
0
90
85
—
—
—
—
—
—
—


Ryegrass, Italian
40
60
90
35
30
50
60
90
30
85
80
80
80
45


Soybean
20
15
5
5
15
20
10
20
0
35
10
20
15
5


Sunflower
10
0
—
5
20
15
0
—
—
—
—
—
—
—


Surinam Grass
80
65
75
55
20
80
75
—
—
—
—
—
—
—


Velvetleaf
—
10
75
10
5
55
55
85
45
80
40
30
80
10


Waterhemp
—
—
—
—
—
—
—
100
100
100
100
100
100
100


Wheat
5
0
5
5
0
5
5
35
5
5
5
15
5
0












Compounds





















62 g ai/ha
164
166
168
169
170
171
172
174
179
183
185
188
189
195










Preemergence





















Barnyardgrass
15
75
100
80
98
75
98
20
100
95
98
100
98
—


Bermudagrass
—
—
—
—
—
—
—
—
—
—
—
—
—
98


Blackgrass
10
90
90
90
95
98
95
80
100
95
95
100
100
90


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
—
—
—
45


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
5
—
15
5
10
0
5
5
20
15
5
5
15
5


Crabgrass, Large
75
98
100
100
100
100
100
98
100
100
100
100
100
100


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
—
—
—
95


Foxtail, Giant
65
100
100
100
100
100
100
85
100
100
100
100
100
98


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
—
—
—
90


Galium
50
10
100
100
100
98
100
50
100
100
100
90
80
80


Goosegrass
—
—
—
—
—
—
—
—
—
—
—
—
—
100


Johnsongrass
15
30
98
75
75
25
75
25
60
35
70
85
85
—


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
75


Lambsquarters
85
—
98
90
85
100
90
85
98
100
100
90
90
80


Morningglory
15
10
55
55
55
20
35
5
40
45
55
60
40
50


Nightshade
—
—
—
—
—
—
—
—
—
—
—
—
—
85


Nutsedge, Yellow
0
0
0
5
5
0
5
0
0
0
0
5
0
0


Oat, Wild
—
—
—
—
—
—
—
—
—
—
—
—
—
90


Oilseed Rape
5
50
100
98
95
50
90
5
98
80
85
70
70
—


Pigweed
35
100
100
100
100
100
100
100
100
100
100
100
100
98


Ragweed
20
20
30
15
60
5
40
15
40
50
80
—
—
20


Russian Thistle
—
—
—
—
—
—
—
—
—
—
—
—
—
90


Ryegrass, Italian
10
40
98
90
90
50
100
40
95
80
100
65
85
80


Soybean
0
5
10
5
5
0
10
0
10
5
10
20
15
0


Sunflower
—
—
—
—
—
—
—
—
—
—
—
—
—
15


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
—
—
75


Velvetleaf
10
0
100
75
100
25
75
15
75
55
80
65
40
25


Waterhemp
—
100
—
—
—
—
—
—
—
—
—
100
100
—


Wheat
0
0
40
15
40
0
40
0
15
10
40
30
15
5













Compounds




















31 g ai/ha
14
15
16
23
25
26
47
106
120
129











Preemergence



















Bermudagrass
98
100
5
100
85
75
100
100
98
98



Blackgrass
5
50
90
5
60
55
90
50
90
90



Bromegrass, Downy
30
25
5
0
5
5
15
0
45
30



Cocklebur
0
0
—
0
0
0
0
—
0
0



Corn
0
0
—
5
0
0
0
0
0
0



Crabgrass, Large
95
100
—
100
98
98
45
100
100
98



Cupgrass, Woolly
5
45
—
95
20
10
45
5
90
80



Foxtail, Giant
95
95
—
98
98
98
95
65
98
95



Foxtail, Green
80
95
100
100
90
85
100
90
90
90



Galium
20
75
100
80
0
50
85
5
98
85



Goosegrass
98
100
—
95
90
95
98
80
98
98



Johnsongrass
20
55
—
55
5
15
5
0
25
25



Kochia
0
70
—
95
10
45
85
0
10
5



Lambsquarters
95
100
—
95
90
70
100
85
85
95



Morningglory
10
5
—
20
—
—
5
0
45
0



Nightshade
55
25
—
50
10
55
45
0
95
85



Nutsedge, Yellow
0
0
—
5
0
0
0
0
0
0



Oat, Wild
20
40
98
45
20
45
80
10
85
40



Pigweed
100
100
—
100
100
100
100
85
100
100



Ragweed
—
—
—
5
5
15
5
0
0
0



Russian Thistle
10
50
45
—
0
—
85
0
0
—



Ryegrass, Italian
10
40
5
0
5
10
35
5
40
60



Soybean
0
0
—
0
0
0
0
0
0
0



Sunflower
0
0
—
0
0
0
0
—
0
0



Surinam Grass
20
40
—
15
15
10
5
5
65
95



Velvetleaf
10
0
—
5
0
25
45
0
5
0



Wheat
0
10
0
0
0
0
0
0
5
0













Compounds





















31 g ai/ha
138
139
142
145
146
147
148
153
154
155
156
160
162
163










Preemergence





















Barnyardgrass
—
—
—
—
—
—
—
90
45
40
85
35
98
10


Bermudagrass
100
98
98
98
98
100
98
—
—
—
—
—
—
—


Blackgrass
90
45
90
85
50
50
60
90
90
90
85
40
60
5


Bromegrass, Downy
10
0
20
5
0
10
5
—
—
—
—
—
—
—


Cocklebur
5
—
0
0
0
35
10
—
—
—
—
—
—
—


Corn
20
0
0
0
0
10
5
10
0
5
5
5
5
10


Crabgrass, Large
98
100
100
98
98
98
100
100
90
100
90
100
100
65


Cupgrass, Woolly
60
30
55
55
40
50
50
—
—
—
—
—
—
—


Foxtail, Giant
98
95
100
95
40
85
98
100
100
100
90
100
98
40


Foxtail, Green
90
90
90
90
90
95
95
—
—
—
—
—
—
—


Galium
95
5
60
60
95
100
80
80
5
98
85
5
100
0


Goosegrass
100
98
100
98
70
98
90
—
—
—
—
—
—
—


Johnsongrass
45
15
90
0
5
40
15
90
40
80
75
100
35
30


Kochia
55
65
55
50
30
35
40
—
—
—
—
—
—
—


Lambsquarters
95
60
80
55
10
35
15
95
100
90
100
100
—
—


Morningglory
15
15
—
15
35
30
20
20
0
10
5
5
55
20


Nightshade
90
—
95
35
—
98
25
—
—
—
—
—
—
—


Nutsedge, Yellow
5
0
0
—
0
0
0
0
0
0
0
0
0
0


Oat, Wild
80
10
85
45
5
60
35
—
—
—
—
—
—
—


Oilseed Rape
—
—
—
—
—
—
—
90
5
50
10
5
80
0


Pigweed
98
98
98
90
85
100
100
100
100
100
100
100
100
95


Ragweed
40
0
40
0
0
25
15
5
0
20
5
0
50
0


Russian Thistle
85
—
—
0
0
0
—
—
—
—
—
—
—
—


Ryegrass, Italian
10
35
30
5
0
10
5
60
10
35
45
15
60
10


Soybean
5
5
0
—
10
—
5
20
0
0
5
5
15
5


Sunflower
5
0
15
0
10
15
0
—
—
—
—
—
—
—


Surinam Grass
55
15
60
35
10
55
60
—
—
—
—
—
—
—


Velvetleaf
5
0
35
0
0
25
15
—
5
30
5
5
55
0


Waterhemp
—
—
—
—
—
—
—
100
95
100
100
100
100
90


Wheat
5
0
0
0
0
0
0
10
0
5
0
0
0
0












Compounds





















31 g ai/ha
164
166
168
169
170
171
172
174
179
183
185
188
189
195










Preemergence





















Barnyardgrass
5
5
75
40
80
5
85
5
40
40
55
80
45
—


Bermudagrass
—
—
—
—
—
—
—
—
—
—
—
—
—
98


Blackgrass
5
15
90
80
90
5
90
80
80
80
90
80
90
90


Bromegrass, Downy
—
—
—
—
—
—
—
—
—
—
—
—
—
15


Cocklebur
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Corn
0
0
5
5
5
0
5
0
5
15
5
5
5
0


Crabgrass, Large
70
85
100
100
100
85
100
60
100
100
100
98
98
98


Cupgrass, Woolly
—
—
—
—
—
—
—
—
—
—
—
—
—
20


Foxtail, Giant
50
100
100
100
98
98
100
40
100
100
100
100
100
98


Foxtail, Green
—
—
—
—
—
—
—
—
—
—
—
—
—
90


Galium
0
10
85
100
98
5
80
5
80
60
80
90
80
10


Goosegrass
—
—
—
—
—
—
—
—
—
—
—
—
—
98


Johnsongrass
5
10
75
20
50
0
60
5
5
10
25
55
50
—


Kochia
—
—
—
—
—
—
—
—
—
—
—
—
—
60


Lambsquarters
85
—
98
90
85
100
90
85
98
80
100
90
85
55


Morningglory
5
—
45
25
35
0
30
0
5
30
45
—
10
30


Nightshade
—
—
—
—
—
—
—
—
—
—
—
—
—
60


Nutsedge, Yellow
0
0
0
0
0
0
0
0
0
0
0
5
0
0


Oat, Wild
—
—
—
—
—
—
—
—
—
—
—
—
—
80


Oilseed Rape
5
50
100
50
95
0
60
0
80
60
60
20
—
—


Pigweed
10
100
100
100
100
60
100
98
100
100
100
100
98
98


Ragweed
20
20
10
15
5
0
35
5
40
50
40
—
—
15


Russian Thistle
—
—
—
—
—
—
—
—
—
—
—
—
—
90


Ryegrass, Italian
5
5
70
85
55
10
100
10
45
65
90
60
60
50


Soybean
0
5
5
0
5
0
5
0
0
5
5
5
5
0


Sunflower
—
—
—
—
—
—
—
—
—
—
—
—
—
0


Surinam Grass
—
—
—
—
—
—
—
—
—
—
—
—
—
55


Velvetleaf
10
0
80
50
60
5
60
5
30
45
60
45
15
10


Waterhemp
—
55
—
—
—
—
—
—
—
—
—
100
98
—


Wheat
0
0
5
5
10
0
15
0
5
5
10
30
5
0
















Compound

Compound



31 g ai/ha
196
31 g ai/ha
196











Preemergence












Barnyardgrass
—
Morningglory
40



Bermudagrass
98
Nightshade
100



Blackgrass
90
Nutsedge, Yellow
0



Bromegrass, Downy
60
Oat, Wild
80



Cocklebur
5
Oilseed Rape
—



Corn
25
Pigweed
95



Crabgrass, Large
100
Ragweed
40



Cupgrass, Woolly
90
Russian Thistle
90



Foxtail, Giant
100
Ryegrass, Italian
80



Foxtail, Green
90
Soybean
10



Galium
85
Sunflower
5



Goosegrass
100
Surinam Grass
90



Johnsongrass
98
Velvetleaf
60



Kochia
90
Waterhemp
—



Lambsquarters
85
Wheat
0








Compound

Compound



16 g ai/ha
15
16 g ai/ha
15











Preemergence












Bermudagrass
100
Lambsquarters
95



Blackgrass
15
Morningglory
5



Bromegrass, Downy
15
Nightshade
10



Cocklebur
0
Nutsedge, Yellow
0



Corn
0
Oat, Wild
35



Crabgrass, Large
98
Pigweed
98



Cupgrass, Woolly
5
Russian Thistle
5



Foxtail, Giant
95
Ryegrass, Italian
10



Foxtail, Green
95
Soybean
0



Galium
50
Sunflower
0



Goosegrass
100
Surinam Grass
10



Johnsongrass
15
Velvetleaf
0



Kochia
0
Wheat
0

















Compounds


Compounds















16 g ai/ha
160
189
16 g ai/ha
160
189











Preemergence














Barnyardgrass
5
25
Nutsedge, Yellow
0
0



Blackgrass
0
75
Oilseed Rape
0
5



Corn
5
5
Pigweed
90
85



Crabgrass, Large
90
98
Ragweed
0
—



Foxtail, Giant
80
100
Ryegrass, Italian
5
50



Galium
—
80
Soybean
0
5



Johnsongrass
85
30
Velvetleaf
0
10



Lambsquarters
95
45
Waterhemp
100
90



Morningglory
0
—
Wheat
0
0










Test D
Seeds of plant species selected from bluegrass (annual bluegrass, Poa annua), blackgrass (Alopecurus myosuroides), 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), foxtail, green (green foxtail, Setaria viridis), deadnettle (henbit deadnettle, Lamium amplexicaule), ryegrass, Italian (Italian ryegrass, Lolium multiflorum), kochia (Kochia scoparia), lambsquarters (Chenopodium album), oilseed rape (Brassica napus), pigweed (Amaranthus retroflexus), Russian thistle (Salsola iberica), chamomile (scentless chamomile, Matricaria inodora), speedwell (bird's-eye speedwell, Veronica persica), barley, spring (spring barley, Hordeum vulgare), wheat, spring (spring wheat, Triticum aestivum), buckwheat, wild (wild buckwheat, Polygonum convolvulus), mustard, wild (wild mustard, Sinapis arvensis), oat, wild (wild oat, Avena fatua), radish, wild (wild radish, Raphanus raphanistrum), windgrass (Apera spica-venti), barley, winter (winter barley, Hordeum vulgare), and wheat, winter (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 same crop and weed species were planted in pots containing the planting medium 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 14 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









Compounds
















250 g ai/ha
14
15
16
23
106
120
129











Postemergence
















Barley, Spring
40
40
35
15
30
30
10



Barley, Winter
40
40
40
20
10
40
30



Blackgrass
85
85
40
30
30
85
70



Bluegrass
95
95
70
40
30
95
70



Bromegrass, Downy
40
40
50
25
15
25
30



Buckwheat, Wild
100
100
50
75
100
98
100



Canarygrass
80
80
80
30
30
95
80



Chamomile
100
100
10
5
25
90
35



Chickweed
98
100
95
90
90
100
100



Deadnettle
100
100
90
90
80
100
100



Field Poppy
100
100
100
100
100
100
85



Field Violet
100
100
80
80
100
100
80



Foxtail, Green
95
100
95
25
40
100
100



Galium
70
100
70
90
60
100
98



Kochia
100
100
95
95
100
100
100



Lambsquarters
100
100
100
100
90
100
100



Mustard, Wild
100
100
100
100
100
—
—



Oat, Wild
55
40
50
20
20
70
25



Oilseed Rape
100
100
100
95
95
98
100



Pigweed
100
100
100
100
90
100
100



Radish, Wild
100
100
100
100
100
100
100



Russian Thistle
100
100
100
100
100
100
100



Ryegrass, Italian
35
20
35
15
20
30
15



Speedwell
100
100
100
60
90
100
100



Wheat, Spring
40
50
20
15
20
25
20



Wheat, Winter
25
35
25
15
5
20
20



Windgrass
100
100
35
30
50
100
95















Compounds

Compounds
















250 g ai/ha
137
138
195
250 g ai/ha
137
138
195











Postemergence
















Barley, Spring
40
40
40
Kochia
100
100
100



Barley, Winter
10
20
45
Lambsquarters
95
100
100



Blackgrass
80
85
70
Mustard, Wild
100
100
100



Bluegrass
90
85
80
Oat, Wild
50
75
45



Bromegrass, Downy
40
50
40
Oilseed Rape
100
100
100



Buckwheat, Wild
80
80
65
Pigweed
100
100
95



Canarygrass
75
80
55
Radish, Wild
100
100
—



Chamomile
40
80
50
Russian Thistle
90
100
100



Chickweed
90
100
90
Ryegrass, Italian
40
50
25



Deadnettle
85
95
90
Speedwell
100
100
100



Field Poppy
100
100
100
Wheat, Spring
25
35
35



Field Violet
95
90
95
Wheat, Winter
20
25
40



Foxtail, Green
95
100
100
Windgrass
80
90
80



Galium
75
100
80













Compounds
















125 g ai/ha
14
15
16
23
106
120
129











Postemergence
















Barley, Spring
30
30
20
10
20
15
10



Barley, Winter
35
20
25
10
5
20
15



Blackgrass
70
50
25
20
20
75
50



Bluegrass
70
50
60
30
15
70
60



Bromegrass, Downy
30
20
40
20
15
20
30



Buckwheat, Wild
60
70
20
40
10
95
100



Canarygrass
55
50
40
25
20
90
70



Chamomile
100
25
5
0
0
80
30



Chickweed
90
100
95
30
90
100
100



Deadnettle
100
100
50
60
60
100
98



Field Poppy
100
100
100
100
100
100
100



Field Violet
100
100
70
70
85
100
100



Foxtail, Green
30
75
90
25
30
95
95



Galium
55
100
60
70
40
98
85



Kochia
100
100
75
90
95
100
100



Lambsquarters
100
100
100
100
50
100
100



Mustard, Wild
100
100
—
100
90
—
—



Oat, Wild
40
30
45
15
5
35
20



Oilseed Rape
90
100
100
85
80
90
100



Pigweed
100
100
90
95
90
100
100



Radish, Wild
100
100
100
75
100
100
100



Russian Thistle
100
100
100
90
60
100
100



Ryegrass, Italian
25
10
30
10
10
15
10



Speedwell
100
100
95
50
90
100
100



Wheat, Spring
35
40
15
10
10
20
15



Wheat, Winter
15
25
20
15
5
15
20



Windgrass
75
75
25
20
35
100
70













Compounds
















125 g ai/ha
137
138
145
147
148
155
156
195
196










Postemergence
















Barley, Spring
30
35
20
25
25
35
30
30
55


Barley, Winter
1
20
20
30
30
35
30
30
40


Blackgrass
70
80
30
60
65
85
60
50
80


Bluegrass
80
70
40
70
70
90
80
60
80


Bromegrass, Downy
30
40
10
50
20
55
35
35
65


Buckwheat, Wild
65
80
85
70
70
75
85
35
95


Canarygrass
50
50
60
80
70
85
80
40
85


Chamomile
20
60
30
80
95
85
100
20
85


Chickweed
85
95
90
80
90
100
95
85
100


Deadnettle
80
80
100
100
100
100
100
75
100


Field Poppy
100
100
100
100
100
100
100
100
100


Field Violet
90
85
95
90
95
95
95
85
100


Foxtail, Green
80
80
100
60
60
80
65
100
95


Galium
75
90
70
90
75
75
80
75
90


Kochia
95
100
100
95
85
85
90
100
90


Lambsquarters
95
95
100
95
95
95
95
95
95


Mustard, Wild
95
100
100
100
100
100
100
95
100


Oat, Wild
35
50
35
35
55
75
65
35
70


Oilseed Rape
100
100
100
100
100
100
100
100
100


Pigweed
100
100
100
95
95
95
95
80
100


Radish, Wild
100
100
—
100
100
100
100
—
100


Russian Thistle
85
95
100
80
75
85
80
85
75


Ryegrass, Italian
35
40
30
35
20
60
25
20
75


Speedwell
95
98
100
—
—
—
—
100
—


Wheat, Spring
20
25
25
25
25
50
25
25
35


Wheat, Winter
15
20
10
20
25
25
20
25
35


Windgrass
50
60
80
75
80
95
80
70
95












Compounds
















62 g ai/ha
14
15
16
23
106
120
129











Postemergence
















Barley, Spring
25
25
15
10
15
15
5



Barley, Winter
25
15
10
10
5
20
10



Blackgrass
35
30
20
10
10
30
10



Bluegrass
35
25
40
25
10
40
20



Bromegrass, Downy
20
10
20
15
10
10
20



Buckwheat, Wild
40
30
10
35
10
85
80



Canarygrass
40
40
35
20
10
20
15



Chamomile
60
0
0
0
0
40
30



Chickweed
80
100
90
15
90
98
100



Deadnettle
40
98
45
50
40
90
80



Field Poppy
100
100
100
90
100
100
100



Field Violet
100
100
30
50
70
100
100



Foxtail, Green
25
80
80
20
20
80
85



Galium
55
70
50
50
40
70
75



Kochia
95
90
95
85
70
100
100



Lambsquarters
80
100
100
80
30
100
95



Mustard, Wild
90
100
90
85
80
—
—



Oat, Wild
25
10
30
10
5
20
10



Oilseed Rape
70
70
95
75
10
80
95



Pigweed
100
80
80
80
60
90
100



Radish, Wild
85
100
100
40
100
90
100



Russian Thistle
75
100
100
70
30
98
100



Ryegrass, Italian
20
5
25
10
5
10
5



Speedwell
100
100
85
20
0
100
100



Wheat, Spring
20
30
10
10
5
10
10



Wheat, Winter
5
15
15
10
5
10
10



Windgrass
40
25
20
10
25
95
30













Compounds
















62 g ai/ha
137
138
145
147
148
155
156
195
196










Postemergence
















Barley, Spring
25
25
15
20
20
25
25
20
35


Barley, Winter
5
15
10
25
25
25
25
15
35


Blackgrass
50
70
25
30
30
60
35
35
85


Bluegrass
40
50
25
55
25
75
70
40
75


Bromegrass, Downy
20
30
10
15
15
35
15
20
50


Buckwheat, Wild
65
50
45
65
75
70
80
30
90


Canarygrass
30
30
35
55
20
70
65
20
80


Chamomile
15
30
10
75
75
80
75
20
75


Chickweed
80
85
80
80
80
75
90
60
95


Deadnettle
70
75
90
90
100
90
100
75
100


Field Poppy
100
90
100
100
95
100
100
95
100


Field Violet
85
75
95
100
95
100
95
75
95


Foxtail, Green
70
75
100
25
50
70
25
75
85


Galium
40
80
40
75
70
70
75
50
70


Kochia
90
100
100
90
85
85
95
95
90


Lambsquarters
80
90
100
90
95
90
85
80
90


Mustard, Wild
80
95
90
100
100
100
100
80
100


Oat, Wild
20
30
30
30
30
55
20
25
45


Oilseed Rape
98
100
70
95
80
100
100
95
100


Pigweed
95
95
100
85
95
95
90
75
95


Radish, Wild
90
95
—
95
100
95
100
—
100


Russian Thistle
85
90
98
80
85
85
90
80
80


Ryegrass, Italian
25
35
15
15
20
25
10
20
30


Speedwell
85
90
85
—
—
—
—
100
—


Wheat, Spring
10
10
20
20
20
25
20
20
35


Wheat, Winter
10
20
10
15
15
15
15
10
25


Windgrass
40
50
60
50
60
80
70
30
95












Compounds
















31 g ai/ha
14
15
16
23
106
120
129











Postemergence
















Barley, Spring
25
15
15
0
10
10
5



Barley, Winter
10
10
10
0
5
15
5



Blackgrass
25
15
10
10
10
10
10



Bluegrass
20
10
20
20
10
10
10



Bromegrass, Downy
15
10
10
10
0
10
10



Buckwheat, Wild
0
30
0
25
0
75
60



Canarygrass
25
35
30
15
5
5
10



Chamomile
20
0
0
0
0
25
30



Chickweed
50
100
70
10
90
85
90



Deadnettle
25
75
25
30
30
90
75



Field Poppy
100
100
100
70
100
100
100



Field Violet
100
100
20
40
70
70
100



Foxtail, Green
10
30
30
15
10
15
35



Galium
45
55
40
30
40
60
50



Kochia
95
90
90
80
60
98
98



Lambsquarters
80
100
80
30
30
98
85



Mustard, Wild
50
70
—
40
80
—
—



Oat, Wild
15
10
10
10
5
10
10



Oilseed Rape
30
100
70
50
10
50
80



Pigweed
100
80
70
50
50
90
100



Radish, Wild
70
100
100
20
100
100
90



Russian Thistle
0
100
95
50
25
95
98



Ryegrass, Italian
5
5
20
10
5
5
5



Speedwell
100
100
75
10
0
100
100



Wheat, Spring
15
25
10
5
5
10
10



Wheat, Winter
5
10
10
5
5
5
5



Windgrass
30
10
10
5
10
15
20













Compounds
















31 g ai/ha
137
138
145
147
148
155
156
195
196










Postemergence
















Barley, Spring
15
20
10
15
15
15
20
15
20


Barley, Winter
5
5
5
20
20
20
20
10
20


Blackgrass
30
50
20
25
15
50
15
25
65


Bluegrass
20
30
20
10
15
35
65
20
70


Bromegrass, Downy
15
20
5
5
5
15
10
15
35


Buckwheat, Wild
30
40
35
50
60
70
75
20
70


Canarygrass
20
25
35
35
30
70
30
10
70


Chamomile
10
10
10
60
70
70
70
20
70


Chickweed
50
60
60
70
70
70
75
40
85


Deadnettle
40
50
70
95
65
75
85
65
100


Field Poppy
40
90
100
90
100
95
100
75
100


Field Violet
70
70
75
95
95
100
95
70
85


Foxtail, Green
50
40
60
15
15
15
25
50
80


Galium
20
75
35
65
70
70
75
30
85


Kochia
85
95
98
85
85
80
80
85
85


Lambsquarters
75
80
90
75
85
95
90
75
90


Mustard, Wild
60
90
75
100
100
100
95
80
100


Oat, Wild
10
20
20
15
15
20
15
20
50


Oilseed Rape
90
95
50
60
35
100
100
85
100


Pigweed
90
95
95
70
85
75
90
65
95


Radish, Wild
40
80
—
100
100
95
85
—
100


Russian Thistle
—
75
95
85
75
80
85
40
90


Ryegrass, Italian
10
25
10
10
15
15
15
10
15


Speedwell
70
80
70
—
—
—
—
100
—


Wheat, Spring
5
5
10
15
10
20
15
10
25


Wheat, Winter
5
20
10
15
10
10
15
10
20


Windgrass
20
30
35
25
30
70
50
15
75













Compounds
















16 g ai/ha
15
16
23
106
120
129











Postemergence















Barley, Spring
10
5
0
5
5
5



Barley, Winter
10
5
0
0
10
5



Blackgrass
15
5
5
5
5
5



Bluegrass
0
10
20
10
10
10



Bromegrass, Downy
5
0
0
0
5
10



Buckwheat, Wild
0
0
20
0
50
60



Canarygrass
25
20
10
5
0
10



Chamomile
0
0
0
0
10
20



Chickweed
40
40
5
20
75
75



Deadnettle
50
10
20
20
30
60



Field Poppy
100
0
75
100
100
100



Field Violet
80
0
20
70
70
40



Foxtail, Green
15
30
15
0
5
35



Galium
50
20
25
20
50
40



Kochia
20
85
20
60
98
98



Lambsquarters
50
75
30
20
95
85



Mustard, Wild
0
10
20
20
—
—



Oat, Wild
10
0
10
0
10
10



Oilseed Rape
70
40
50
10
20
80



Pigweed
80
50
50
10
0
100



Radish, Wild
100
90
20
100
100
90



Russian Thistle
60
90
50
20
95
98



Ryegrass, Italian
0
10
5
5
5
5



Speedwell
100
25
5
0
60
100



Wheat, Spring
20
5
0
0
10
5



Wheat, Winter
5
5
0
5
5
5



Windgrass
5
0
0
5
5
15













Compounds
















16 g ai/ha
137
138
145
147
148
155
156
195
196










Postemergence
















Barley, Spring
10
10
10
15
10
10
15
10
15


Barley, Winter
0
5
5
15
10
15
10
0
15


Blackgrass
10
30
20
15
10
5
10
20
15


Bluegrass
5
20
0
5
5
20
15
10
60


Bromegrass, Downy
5
10
5
5
5
5
10
5
15


Buckwheat, Wild
30
40
30
45
60
75
70
15
50


Canarygrass
10
10
30
15
10
20
15
10
30


Chamomile
0
0
0
45
60
60
50
20
60


Chickweed
40
60
75
60
60
65
60
30
70


Deadnettle
20
50
50
65
70
75
70
60
85


Field Poppy
30
80
75
90
90
80
85
35
100


Field Violet
50
60
80
95
90
95
95
70
80


Foxtail, Green
40
20
5
15
15
20
10
30
55


Galium
20
60
30
55
60
65
70
20
70


Kochia
75
95
90
70
75
70
75
70
70


Lambsquarters
40
70
25
75
85
95
85
60
85


Mustard, Wild
50
75
70
95
55
80
100
60
100


Oat, Wild
0
10
10
10
5
10
10
10
15


Oilseed Rape
70
85
50
25
30
85
100
70
80


Pigweed
90
90
70
75
70
70
85
60
85


Radish, Wild
40
80
—
85
90
85
65
—
65


Russian Thistle
30
50
40
45
65
70
60
15
80


Ryegrass, Italian
0
10
0
5
5
5
5
5
5


Speedwell
70
80
55
—
—
—
—
100
—


Wheat, Spring
0
5
5
10
10
15
10
5
15


Wheat, Winter
5
10
5
10
10
5
10
5
15


Windgrass
10
15
10
15
15
20
25
10
60
















Compound

Compound



8 g ai/ha
145
8 g ai/ha
145











Postemergence












Barley, Spring
5
Galium
5



Barley, Winter
0
Kochia
80



Blackgrass
5
Lambsquarters
10



Bluegrass
0
Mustard, Wild
25



Bromegrass, Downy
5
Oat, Wild
10



Buckwheat, Wild
15
Oilseed Rape
0



Canarygrass
20
Pigweed
20



Chamomile
0
Russian Thistle
10



Chickweed
40
Ryegrass, Italian
0



Deadnettle
0
Speedwell
50



Field Poppy
25
Wheat, Spring
5



Field Violet
70
Wheat, Winter
5



Foxtail, Green
5
Windgrass
5













Compounds
















250 g ai/ha
14
15
16
106
120
129
195











Preemergence
















Barley, Spring
20
15
5
0
20
20
30



Barley, Winter
35
30
25
20
40
15
20



Blackgrass
60
90
100
0
100
100
100



Bluegrass
100
100
100
0
100
100
80



Bromegrass, Downy
30
40
40
0
60
30
50



Buckwheat, Wild
40
100
20
100
100
100
40



Canarygrass
98
100
100
0
100
100
95



Chamomile
—
—
100
—
100
100
100



Chickweed
100
100
—
100
100
100
—



Deadnettle
100
100
100
0
100
100
100



Field Poppy
—
—
100
—
100
100
100



Field Violet
95
—
100
—
100
100
—



Foxtail, Green
100
100
100
100
100
100
100



Galium
100
100
20
80
100
100
80



Kochia
90
100
100
30
100
100
85



Lambsquarters
75
100
100
40
100
100
75



Mustard, Wild
95
100
100
60
100
100
100



Oat, Wild
50
100
100
10
100
100
75



Oilseed Rape
40
75
100
20
70
60
20



Pigweed
100
100
100
40
100
100
95



Radish, Wild
100
100
—
30
100
100
—



Russian Thistle
40
80
90
0
100
100
30



Ryegrass, Italian
50
70
60
0
100
90
60



Speedwell
100
—
100
—
—
—
100



Wheat, Spring
15
5
10
0
20
15
0



Wheat, Winter
20
5
0
0
10
10
10



Windgrass
85
100
100
80
100
100
100














Compounds
















125 g ai/ha
14
15
16
106
120
129











Preemergence















Barley, Spring
15
10
5
0
10
15



Barley, Winter
10
20
10
0
15
10



Blackgrass
10
80
70
0
100
100



Bluegrass
85
80
30
0
100
100



Bromegrass, Downy
20
0
25
0
25
20



Buckwheat, Wild
35
100
0
100
70
70



Canarygrass
90
90
90
0
100
100



Chamomile
—
—
70
—
100
30



Chickweed
100
100
—
100
100
100



Deadnettle
100
95
100
0
100
100



Field Poppy
—
—
100
—
100
100



Field Violet
95
—
90
—
100
100



Foxtail, Green
75
100
100
0
100
100



Galium
100
100
20
40
100
100



Kochia
80
70
90
30
95
100



Lambsquarters
60
100
95
40
100
90



Mustard, Wild
90
100
100
50
100
80



Oat, Wild
20
40
100
10
55
55



Oilseed Rape
30
20
50
10
30
30



Pigweed
90
98
90
20
100
100



Radish, Wild
100
100
—
30
90
100



Russian Thistle
10
80
—
0
100
100



Ryegrass, Italian
25
25
60
0
80
70



Speedwell
100
—
100
—
—
—



Wheat, Spring
5
0
5
0
10
5



Wheat, Winter
10
0
0
0
5
5



Windgrass
40
100
100
25
100
75














Compounds
















125 g ai/ha
147
148
155
156
195
196











Preemergence















Barley, Spring
10
5
10
15
0
30



Barley, Winter
15
5
10
15
0
40



Blackgrass
40
5
70
70
80
100



Bluegrass
35
50
85
100
50
100



Bromegrass, Downy
15
20
35
95
35
90



Buckwheat, Wild
100
50
70
100
20
95



Canarygrass
100
100
100
100
80
100



Chamomile
95
100
100
100
100
100



Chickweed
100
100
100
100
—
100



Deadnettle
100
100
95
100
100
100



Field Poppy
100
95
100
100
100
100



Field Violet
100
100
100
100
—
100



Foxtail, Green
100
100
100
100
100
100



Galium
—
—
—
—
30
—



Kochia
70
75
75
80
80
100



Lambsquarters
85
90
90
100
30
100



Mustard, Wild
95
95
100
100
100
100



Oat, Wild
70
65
60
90
75
100



Oilseed Rape
15
20
100
100
10
100



Pigweed
100
100
100
100
100
100



Radish, Wild
100
100
100
100
—
100



Russian Thistle
—
—
—
—
0
—



Ryegrass, Italian
30
35
65
60
20
100



Speedwell
100
100
100
100
100
100



Wheat, Spring
5
5
5
5
0
25



Wheat, Winter
5
10
5
5
0
15



Windgrass
100
90
100
100
100
100














Compounds
















62 g ai/ha
14
15
16
106
120
129











Preemergence















Barley, Spring
10
0
5
0
5
5



Barley, Winter
0
5
5
0
10
0



Blackgrass
0
25
40
0
98
30



Bluegrass
30
5
20
0
100
85



Bromegrass, Downy
10
0
25
0
5
10



Buckwheat, Wild
30
100
0
100
10
0



Canarygrass
25
80
50
0
100
100



Chamomile
—
—
25
—
20
30



Chickweed
100
100
—
100
90
100



Deadnettle
70
40
60
0
100
100



Field Poppy
—
—
100
—
80
70



Field Violet
90
—
80
—
95
100



Foxtail, Green
10
100
100
0
100
100



Galium
0
30
—
0
65
100



Kochia
40
0
90
0
30
75



Lambsquarters
40
90
80
40
90
90



Mustard, Wild
50
100
100
50
90
40



Oat, Wild
20
15
10
0
25
5



Oilseed Rape
0
10
50
10
10
10



Pigweed
70
70
80
0
100
90



Radish, Wild
40
0
—
30
20
10



Russian Thistle
0
0
40
0
100
100



Ryegrass, Italian
25
5
10
0
40
10



Speedwell
100
—
40
—
—
—



Wheat, Spring
0
0
0
0
5
0



Wheat, Winter
0
0
0
0
5
0



Windgrass
20
40
90
5
100
10














Compounds
















62 g ai/ha
147
148
155
156
195
196











Preemergence















Barley, Spring
5
5
5
5
0
15



Barley, Winter
5
5
5
10
0
15



Blackgrass
30
5
20
15
75
100



Bluegrass
20
60
60
40
20
75



Bromegrass, Downy
10
10
10
20
25
70



Buckwheat, Wild
30
65
50
65
20
70



Canarygrass
100
60
100
100
40
100



Chamomile
90
70
95
100
100
100



Chickweed
70
70
100
100
—
100



Deadnettle
100
100
80
100
60
100



Field Poppy
95
100
95
95
60
100



Field Violet
95
95
95
100
—
100



Foxtail, Green
75
70
85
30
100
75



Galium
—
—
—
—
10
—



Kochia
50
10
65
65
60
100



Lambsquarters
80
80
90
85
0
100



Mustard, Wild
100
55
100
95
40
100



Oat, Wild
35
30
15
25
0
75



Oilseed Rape
5
10
100
85
0
100



Pigweed
80
85
100
100
60
100



Radish, Wild
100
100
100
100
—
70



Russian Thistle
—
—
—
—
0
—



Ryegrass, Italian
15
5
10
5
0
60



Speedwell
100
50
100
100
100
100



Wheat, Spring
0
0
0
0
0
5



Wheat, Winter
0
0
5
0
0
10



Windgrass
100
35
85
85
75
100















Compounds

Compounds

















31 g ai/ha
14
15
16
106
120
129
16 g ai/ha
16
120
129










Preemergence

















Barley, Spring
0
0
0
0
0
0
Barley, Spring
0
0
0


Barley, Winter
0
0
0
0
0
0
Barley, Winter
0
0
0


Blackgrass
0
0
0
0
80
0
Blackgrass
0
0
0


Bluegrass
0
0
20
—
100
0
Bluegrass
0
0
0


Bromegrass, Downy
0
0
20
0
0
10
Bromegrass, Downy
0
0
0


Buckwheat, Wild
0
0
0
50
—
0
Buckwheat, Wild
0
—
0


Canarygrass
10
25
40
0
90
15
Canarygrass
20
0
0


Chamomile
—
—
0
—
10
30
Chamomile
0
0
0


Chickweed
75
100
—
100
90
100
Chickweed
—
20
0


Deadnettle
60
10
40
0
85
10
Deadnettle
0
0
0


Field Poppy
—
—
100
—
80
75
Field Poppy
100
0
0


Field Violet
75
—
30
—
90
100
Field Violet
0
75
100


Foxtail, Green
0
70
100
0
100
90
Foxtail, Green
25
70
5


Galium
—
—
0
0
15
0
Galium
0
0
—


Kochia
10
0
30
0
10
25
Kochia
30
0
20


Lambsquarters
0
0
50
40
80
80
Lambsquarters
30
—
0


Mustard, Wild
0
100
0
20
—
5
Mustard, Wild
0
0
0


Oat, Wild
0
—
10
0
5
0
Oat, Wild
0
0
0


Oilseed Rape
0
0
0
10
10
0
Oilseed Rape
0
0
0


Pigweed
20
20
80
0
100
80
Pigweed
25
30
30


Radish, Wild
—
0
—
0
—
0
Radish, Wild
—
0
0


Russian Thistle
0
0
35
0
100
100
Russian Thistle
0
100
80


Ryegrass, Italian
0
0
0
0
5
5
Ryegrass, Italian
0
0
0


Speedwell
100
—
20
—
—
—
Speedwell
—
0
—


Wheat, Spring
0
0
0
0
0
0
Wheat, Spring
0
0
0


Wheat, Winter
0
0
0
0
0
0
Wheat, Winter
0
0
0


Windgrass
10
30
20
5
80
0
Windgrass
20
0
0













Compounds
















31 g ai/ha
147
148
155
156
195
196











Preemergence















Barley, Spring
0
0
5
5
0
5



Barley, Winter
0
0
0
5
0
10



Blackgrass
0
10
10
5
70
20



Bluegrass
15
15
15
5
10
35



Bromegrass, Downy
5
0
5
5
0
15



Buckwheat, Wild
10
30
25
50
0
45



Canarygrass
35
50
70
70
25
100



Chamomile
15
20
80
55
0
85



Chickweed
85
60
50
100
—
65



Deadnettle
10
45
5
15
60
40



Field Poppy
75
70
95
100
40
90



Field Violet
100
100
95
95
—
95



Foxtail, Green
25
50
65
10
90
60



Galium
—
—
—
—
0
—



Kochia
15
20
60
30
50
70



Lambsquarters
50
40
55
30
0
65



Mustard, Wild
60
15
55
85
10
95



Oat, Wild
15
20
50
10
0
30



Oilseed Rape
0
0
5
0
0
15



Pigweed
75
70
80
85
60
100



Radish, Wild
10
20
95
10
—
20



Russian Thistle
—
—
—
—
0
—



Ryegrass, Italian
5
5
0
5
0
10



Speedwell
20
95
100
100
100
100



Wheat, Spring
0
0
0
0
0
5



Wheat, Winter
0
5
0
0
0
5



Windgrass
60
10
10
10
40
100














Compounds
















16 g ai/ha
147
148
155
156
195
196











Preemergence















Barley, Spring
0
0
0
5
0
5



Barley, Winter
0
0
5
5
0
5



Blackgrass
0
0
5
0
0
10



Bluegrass
0
0
15
5
0
5



Bromegrass, Downy
0
0
0
0
0
5



Buckwheat, Wild
15
20
10
0
0
60



Canarygrass
5
0
10
15
0
40



Chamomile
25
10
5
10
0
55



Chickweed
35
25
35
50
—
50



Deadnettle
5
10
5
5
60
10



Field Poppy
55
10
80
85
30
95



Field Violet
75
90
90
60
—
80



Foxtail, Green
10
15
20
5
15
60



Galium
—
—
—
—
0
—



Kochia
15
10
30
10
40
35



Lambsquarters
5
35
20
25
0
55



Mustard, Wild
55
20
55
10
0
35



Oat, Wild
5
5
5
5
0
25



Oilseed Rape
0
5
0
0
0
5



Pigweed
35
15
60
50
60
65



Radish, Wild
—
10
100
5
—
50



Russian Thistle
—
—
—
—
0
—



Ryegrass, Italian
0
0
0
0
0
5



Speedwell
10
5
100
10
30
5



Wheat, Spring
0
0
0
0
0
0



Wheat, Winter
0
0
0
0
0
5



Windgrass
0
5
5
0
25
20










Test E
Seeds of plant species selected from corn (Zea mays), soybean (Glycine max), velvetleaf (Abutilon theophrasti), lambsquarters (Chenopodium album), poinsettia, wild (wild poinsettia, Euphorbia heterophylla), pigweed, palmer (palmer pigweed, Amaranthus palmeri), waterhemp (common waterhemp, Amaranthus rudis), smartweed (ladysthumb smartweed, Polygonum persicaria), surinam grass (Brachiaria decumbens), crabgrass, large (large crabgrass, Digitaria sanguinalis), crabgrass, Brazil (Brazilian crabgrass, Digitaria horizontalis), panicum, fall (fall panicum, Panicum dichotomiflorum), foxtail, giant (giant foxtail, Setaria faberii), foxtail, green (green foxtail, Setaria viridis), goosegrass (Eleusine indica), johnsongrass (Sorghum halepense), ragweed (common ragweed, Ambrosia elation), barnyardgrass (Echinochloa crus-galli), sandbur (southern sandbur, Cenchrus echinatus), arrowleaf sida (Sida rhombifolia), ryegrass, Italian (Italian ryegrass, Lolium multiflorum), dayflower, (VA) (Virginia dayflower, Commelina virginica), field bindweed (Convolvulus arvensis), cocklebur (common cocklebur, Xanthium strumarium), morningglory (Ipomoea coccinea), nightshade (eastern black nightshade, Solanum ptycanthum), kochia (Kochia scoparia), nutsedge, yellow (yellow nutsedge, Cyperus esculentus) and beggarticks (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 selected from these crop and weed species were planted in pots containing a growing medium comprising spaghnum peat moss, vermiculite, wetting agent and starter nutrients and treated with postemergence applications of some of the 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









Compound

Compounds














250 g ai/ha
47
125 g ai/ha
47
120











Postemergence













Arrowleaf Sida
85
Arrowleaf Sida
80
50



Barnyardgrass
60
Barnyardgrass
45
30



Beggarticks
50
Beggarticks
50
35



Corn
20
Corn
20
20



Crabgrass, Brazil
50
Crabgrass, Brazil
40
40



Dayflower, VA
30
Dayflower, VA
25
15



Field Bindweed
65
Field Bindweed
—
35



Panicum, Fall
40
Panicum, Fall
30
25



Pigweed, Palmer
100
Pigweed, Palmer
100
100



Poinsettia, Wild
100
Poinsettia, Wild
98
90



Ryegrass, Italian
80
Ryegrass, Italian
50
35



Sandbur
50
Sandbur
30
35



Smartweed
85
Smartweed
80
40



Soybean
75
Soybean
60
50



Waterhemp
95
Waterhemp
85
75
















Compounds

Compounds















62 g ai/ha
47
120
31 g ai/ha
47
120











Postemergence














Arrowleaf Sida
70
50
Arrowleaf Sida
60
40



Barnyardgrass
40
25
Barnyardgrass
30
20



Beggarticks
40
30
Beggarticks
30
20



Corn
20
20
Corn
15
10



Crabgrass, Brazil
40
30
Crabgrass, Brazil
30
25



Dayflower, VA
20
10
Dayflower, VA
10
10



Field Bindweed
—
35
Field Bindweed
40
30



Panicum, Fall
30
20
Panicum, Fall
20
10



Pigweed, Palmer
95
95
Pigweed, Palmer
90
90



Poinsettia, Wild
90
60
Poinsettia, Wild
75
13 



Ryegrass, Italian
30
20
Ryegrass, Italian
20
15



Sandbur
25
30
Sandbur
25
20



Smartweed
50
—
Smartweed
40
—



Soybean
60
40
Soybean
50
30



Waterhemp
80
75
Waterhemp
70
65















Compounds

Compound













16 g ai/ha
47
120
8 g ai/ha
120











Postemergence













Arrowleaf Sida
50
40
Arrowleaf Sida
30



Barnyardgrass
30
10
Barnyardgrass
10



Beggarticks
30
10
Beggarticks
10



Corn
10
10
Corn
10



Crabgrass, Brazil
20
15
Crabgrass, Brazil
10



Dayflower, VA
10
10
Dayflower, VA
10



Field Bindweed
—
20
Panicum, Fall
5



Panicum, Fall
10
10
Pigweed, Palmer
90



Pigweed, Palmer
70
90
Poinsettia, Wild
25



Poinsettia, Wild
75
35
Ryegrass, Italian
0



Ryegrass, Italian
10
10
Sandbur
10



Sandbur
20
10
Smartweed
10



Smartweed
30
10
Soybean
15



Soybean
50
20
Waterhemp
30



Waterhemp
60
50















Compounds

Compounds


















250 g ai/ha
14
15
23
47
120
250 g ai/ha
14
15
23
47
120










Preemergence


















Arrowleaf Sida
80
60
35
95
50
Morningglory
75
65
—
65
60


Barnyardgrass
60
100
20
100
100
Nightshade
98
100
98
98
100


Beggarticks
100
100
—
—
—
Nutsedge, Yellow
15
0
15
35
25


Cocklebur
—
20
0
50
—
Panicum, Fall
100
100
100
100
100


Corn
0
10
20
25
10
Pigweed, Palmer
100
100
100
100
100


Crabgrass, Brazil
100
100
85
100
100
Poinsettia, Wild
75
80
35
100
50


Crabgrass, Large
100
100
100
100
100
Ragweed
90
60
25
90
80


Dayflower, VA
75
95
5
—
50
Ryegrass, Italian
100
100
10
100
98


Field Bindweed
75
95
70
100
98
Sandbur
50
100
65
100
75


Foxtail, Giant
100
100
100
100
100
Smartweed
80
100
—
—
—


Foxtail, Green
100
100
95
100
100
Soybean
35
35
20
40
35


Goosegrass
100
100
60
100
100
Surinam Grass
100
100
20
65
100


Johnsongrass
95
100
60
100
65
Velvetleaf
95
95
65
100
65


Kochia
100
100
100
100
100
Waterhemp
100
100
100
100
100


Lambsquarters
98
100
98
100
98












Compounds
















125 g ai/ha
14
15
16
23
47
120
129











Preemergence
















Arrowleaf Sida
65
50
35
0
60
15
30



Barnyardgrass
60
98
98
20
100
25
35



Beggarticks
98
80
—
—
—
80
—



Cocklebur
50
—
0
0
35
90
35



Corn
0
5
20
0
20
10
10



Crabgrass, Brazil
100
100
100
65
100
100
100



Crabgrass, Large
100
100
90
70
100
100
100



Dayflower, VA
70
60
85
5
—
50
—



Field Bindweed
65
60
50
0
85
40
35



Foxtail, Giant
100
100
100
100
100
100
100



Foxtail, Green
70
100
100
70
100
100
100



Goosegrass
100
100
100
35
100
100
100



Johnsongrass
90
98
98
20
40
35
25



Kochia
98
100
100
100
100
90
95



Lambsquarters
98
100
98
98
100
98
98



Morningglory
75
65
—
—
40
60
50



Nightshade
98
98
100
95
98
98
60



Nutsedge, Yellow
0
0
20
15
10
15
20



Panicum, Fall
100
100
100
100
100
100
100



Pigweed, Palmer
100
100
100
100
100
100
100



Poinsettia, Wild
65
75
98
35
65
35
25



Ragweed
80
30
30
0
50
35
20



Ryegrass, Italian
95
100
98
0
100
90
60



Sandbur
50
90
60
25
—
20
50



Smartweed
—
98
—
—
—
—
—



Soybean
—
35
20
0
40
35
25



Surinam Grass
65
98
35
20
40
90
60



Velvetleaf
80
65
80
65
75
50
25



Waterhemp
100
100
100
98
100
100
100













Compounds
















62 g ai/ha
14
15
16
23
47
120
129











Preemergence
















Arrowleaf Sida
30
40
0
0
40
0
30



Barnyardgrass
35
85
98
0
85
5
10



Beggarticks
90
50
—
—
—
—
—



Cocklebur
0
0
0
0
20
90
35



Corn
0
0
20
0
20
5
10



Crabgrass, Brazil
100
100
100
65
100
100
95



Crabgrass, Large
95
100
90
35
100
98
100



Dayflower, VA
60
25
50
0
—
50
—



Field Bindweed
65
40
20
0
50
20
35



Foxtail, Giant
98
100
—
5
100
100
98



Foxtail, Green
50
90
100
5
100
100
100



Goosegrass
100
100
100
20
—
100
60



Johnsongrass
70
65
40
0
35
15
20



Kochia
90
90
100
60
100
50
95



Lambsquarters
98
100
98
0
98
90
75



Morningglory
35
50
—
—
35
35
40



Nightshade
98
98
100
0
98
80
50



Nutsedge, Yellow
0
0
20
0
10
0
0



Panicum, Fall
100
100
100
80
100
100
100



Pigweed, Palmer
100
100
98
100
100
100
100



Poinsettia, Wild
50
65
40
0
40
0
0



Ragweed
35
—
30
0
10
30
20



Ryegrass, Italian
85
80
50
0
70
35
40



Sandbur
15
50
50
0
90
5
20



Smartweed
80
98
—
—
—
—
—



Soybean
25
20
0
0
40
35
20



Surinam Grass
25
75
30
10
25
35
15



Velvetleaf
50
65
80
10
40
35
20



Waterhemp
100
100
100
80
100
100
100













Compounds
















31 g ai/ha
14
15
16
23
47
120
129











Preemergence
















Arrowleaf Sida
30
30
0
0
20
0
0



Barnyardgrass
15
50
50
0
30
0
5



Beggarticks
50
5
—
—
—
0
—



Cocklebur
0
0
0
0
10
0
0



Corn
0
0
0
0
15
—
0



Crabgrass, Brazil
75
98
95
0
80
100
60



Crabgrass, Large
75
90
5
5
75
95
80



Dayflower, VA
50
10
35
0
—
0
—



Field Bindweed
20
5
0
0
25
10
0



Foxtail, Giant
75
98
100
5
100
100
75



Foxtail, Green
35
—
90
0
100
85
100



Goosegrass
100
100
98
—
100
100
50



Johnsongrass
20
65
20
0
30
15
20



Kochia
50
65
70
0
35
20
50



Lambsquarters
98
100
75
0
95
50
0



Morningglory
20
50
—
—
30
30
0



Nightshade
60
35
50
0
75
0
0



Nutsedge, Yellow
0
0
0
0
0
0
0



Panicum, Fall
80
98
100
15
100
95
98



Pigweed, Palmer
100
100
98
90
100
100
100



Poinsettia, Wild
25
30
20
0
25
0
0



Ragweed
20
5
0
0
0
0
5



Ryegrass, Italian
40
75
30
0
40
35
25



Sandbur
5
25
10
0
20
5
20



Smartweed
25
60
—
—
—
—
—



Soybean
10
0
0
0
40
25
15



Surinam Grass
10
50
0
0
20
35
15



Velvetleaf
35
30
30
0
40
30
0



Waterhemp
98
100
100
80
100
98
80















Compounds

Compounds

















16 g ai/ha
14
15
16
23
47
120
129
8 g ai/ha
16
129










Preemergence

















Arrowleaf Sida
10
—
0
0
0
0
0
Arrowleaf Sida
0
0


Barnyardgrass
5
10
10
0
5
0
0
Barnyardgrass
0
0


Beggarticks
5
5
—
—
—
0
—
Cocklebur
—
0


Cocklebur
0
—
0
0
0
0
0
Corn
0
0


Corn
0
0
0
0
0
0
0
Crabgrass, Brazil
30
10


Crabgrass, Brazil
60
60
70
0
35
90
15
Crabgrass, Large
0
0


Crabgrass, Large
65
15
5
5
20
75
10
Dayflower, VA
0
—


Dayflower, VA
10
5
0
0
—
0
—
Field Bindweed
0
0


Field Bindweed
5
5
0
0
25
0
0
Foxtail, Giant
5
0


Foxtail, Giant
50
65
80
0
90
85
20
Foxtail, Green
60
0


Foxtail, Green
25
20
90
0
85
15
60
Goosegrass
40
40


Goosegrass
65
75
40
0
100
95
40
Johnsongrass
0
0


Johnsongrass
10
10
15
0
25
15
20
Kochia
0
35


Kochia
20
35
20
0
25
0
35
Lambsquarters
0
0


Lambsquarters
80
90
0
—
95
0
0
Morningglory
—
0


Morningglory
0
10
—
—
15
0
0
Nightshade
0
0


Nightshade
35
5
0
0
—
0
0
Nutsedge, Yellow
0
0


Nutsedge, Yellow
0
0
0
0
0
0
0
Panicum, Fall
0
0


Panicum, Fall
65
98
70
0
100
95
35
Pigweed, Palmer
95
30


Pigweed, Palmer
75
100
98
90
100
65
80
Poinsettia, Wild
0
0


Poinsettia, Wild
15
30
0
0
0
0
0
Ragweed
0
0


Ragweed
0
0
0
0
0
0
0
Ryegrass, Italian
0
0


Ryegrass, Italian
0
20
0
0
20
0
25
Sandbur
0
0


Sandbur
5
5
0
0
0
5
0
Soybean
0
0


Soybean
0
0
0
0
0
0
15
Surinam Grass
0
0


Surinam Grass
5
5
0
0
15
0
0
Velvetleaf
0
0


Velvetleaf
20
20
20
0
30
15
0
Waterhemp
60
20


Waterhemp
90
98
70
0
100
95
35









Test F
Seeds of plant species selected from corn (Zea mays), soybean (Glycine max), velvetleaf (Abutilon theophrasti), lambsquarters (Chenopodium album), poinsettia, wild (wild poinsettia, Euphorbia heterophylla), pigweed, palmer (palmer pigweed, Amaranthus palmeri), waterhemp (common waterhemp, Amaranthus rudis), surinam grass (Brachiaria decumbens), crabgrass, Brazil (Brazilian crabgrass, Digitaria horizontalis), panicum, fall (fall panicum Panicum dichotomiflorum), crabgrass, large (large crabgrass, Digitaria sanguinalis), foxtail, giant (giant foxtail, Setaria faberii), foxtail, green (green foxtail Setaria viridis), goosegrass (Eleusine indica), ragweed (common ragweed, Ambrosia elatior), barnyardgrass (Echinochloa crus-galli), sandbur (southern sandbur, Cenchrus echinatus), arrowleaf sida (Sida rhombifolia), ryegrass, Italian (Italian ryegrass, Lolium multiflorum), dayflower, VA (Virginia (VA) dayflower, Commelina virginica), field bindweed (Convolvulus arvensis), cocklebur (common cocklebur, Xanthium strumarium), morningglory (Ipomoea coccinea), nightshade (eastern black nightshade, Solanum ptycanthum), kochia (Kochia scoparia), nutsedge, yellow (yellow nutsedge, Cyperus esculentus), johnsongrass (Sorghum halepense), smartweed (ladysthumb smartweed, Polygonum persicaria), and beggarticks (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 selected from these crop and weed species and also pigweed (Amaranthus retroflexus), waterhemp_RES1 (ALS/Triazine resistant common waterhemp, Amaranthus rudis) and waterhemp_RES2 (ALS/HPPD resistant common waterhemp, Amaranthus rudis) were planted in pots containing a planting medium comprising spaghnum peat moss, vermiculite, wetting agent and starter nutrients treated with postemergence applications of some of the 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 F









Compounds

Compounds















250 g ai/ha
169
172
125 g ai/ha
141
145
169
172
196










Postemergence















Arrowleaf Sida
50
100
Arrowleaf Sida
75
70
30
90
95


Barnyardgrass
40
85
Barnyardgrass
40
40
25
50
90


Beggarticks
40
60
Beggarticks
75
45
30
50
70


Corn
10
30
Corn
30
10
10
20
25


Crabgrass, Brazil
30
90
Crabgrass, Brazil
95
50
20
70
95


Dayflower, VA
20
50
Dayflower, VA
75
70
10
30
70


Field Bindweed
55
60
Field Bindweed
85
75
35
60
75


Panicum, Fall
30
50
Panicum, Fall
75
40
25
50
85


Pigweed, Palmer
100
100
Pigweed
95
—
—
—
95


Poinsettia, Wild
85
100
Pigweed, Palmer
100
90
100
100
100


Ryegrass, Italian
30
50
Poinsettia, Wild
98
—
70
100
95


Sandbur
25
40
Ryegrass, Italian
40
40
20
40
80


Smartweed
35
70
Sandbur
35
35
20
30
50


Soybean
50
90
Smartweed
—
—
25
60
—


Waterhemp
100
100
Soybean
85
60
40
75
80


Waterhemp, Res2
100
—
Waterhemp
—
95
100
100
—


Waterhemp, Res1
95
95
Waterhemp, Res2
100
85
100
—
95





Waterhemp, Res1
95
90
95
95
100














Compounds

Compounds


















62 g ai/ha
141
145
162
169
196
62 g ai/ha
141
145
162
169
196










Postemergence


















Arrowleaf Sida
70
60
60
20
95
Pigweed, Palmer
100
85
90
90
100


Barnyardgrass
30
30
35
15
60
Poinsettia, Wild
95
—
80
60
95


Beggarticks
60
35
30
25
60
Ryegrass, Italian
25
30
0
20
70


Corn
20
10
10
10
20
Sandbur
30
35
20
20
30


Crabgrass, Brazil
95
40
30
20
95
Smartweed
—
—
15
15
—


Dayflower, VA
60
60
25
10
60
Soybean
—
50
55
30
70


Field Bindweed
80
70
50
30
75
Waterhemp
—
95
95
90
—


Panicum, Fall
60
40
30
20
85
Waterhemp, Res2
95
—
100
95
95


Pigweed
95
—
—
—
95
Waterhemp, Res1
95
—
95
90
95













Compounds
















31 g ai/ha
141
145
162
169
172
196











Postemergence















Arrowleaf Sida
60
50
35
20
65
90



Barnyardgrass
20
30
25
0
20
60



Beggarticks
50
30
25
25
40
60



Corn
20
10
10
5
15
20



Crabgrass, Brazil
95
40
20
20
50
85



Dayflower, VA
35
50
20
10
20
60



Field Bindweed
70
—
30
20
25
70



Panicum, Fall
50
40
25
15
20
80



Pigweed
95
—
—
—
—
95



Pigweed, Palmer
95
—
90
50
100
100



Poinsettia, Wild
85
—
75
60
80
95



Ryegrass, Italian
15
20
0
0
20
40



Sandbur
20
30
20
15
20
20



Smartweed
—
—
15
10
30
—



Soybean
80
40
45
20
50
65



Waterhemp
—
95
95
90
95
—



Waterhemp, Res2
95
—
95
85
—
95



Waterhemp, Res1
95
—
95
90
70
95















Compounds

Compounds


















16 g ai/ha
141
145
162
169
196
16 g ai/ha
141
145
162
169
196










Postemergence


















Arrowleaf Sida
50
40
30
20
90
Pigweed, Palmer
95
70
80
50
100


Barnyardgrass
20
20
10
0
40
Poinsettia, Wild
80
—
60
50
85


Beggarticks
40
25
25
25
60
Ryegrass, Italian
10
10
0
0
20


Corn
15
10
10
5
15
Sandbur
10
20
15
15
20


Crabgrass, Brazil
80
25
15
20
75
Smartweed
—
—
10
10
—


Dayflower, VA
10
20
20
10
50
Soybean
70
35
30
20
60


Field Bindweed
60
60
20
20
60
Waterhemp
—
90
90
75
—


Panicum, Fall
50
25
20
10
40
Waterhemp, Res2
95
—
90
75
90


Pigweed
95
—
—
—
95
Waterhemp, Res1
95
—
90
85
95














Compounds

Compound















8 g ai/ha
141
145
162
196
4 g ai/ha
162











Postemergence















Arrowleaf Sida
40
30
25
80
Arrowleaf Sida
10



Barnyardgrass
10
20
10
30
Barnyardgrass
10



Beggarticks
40
10
20
50
Beggarticks
15



Corn
15
5
5
15
Corn
5



Crabgrass, Brazil
70
15
15
60
Crabgrass, Brazil
15



Dayflower, VA
10
15
15
30
Dayflower, VA
5



Field Bindweed
50
50
20
50
Field Bindweed
20



Panicum, Fall
30
10
20
20
Panicum, Fall
15



Pigweed
90
—
—
85
Pigweed, Palmer
70



Pigweed, Palmer
95
40
70
95
Poinsettia, Wild
15



Poinsettia, Wild
60
—
30
75
Ryegrass, Italian
0



Ryegrass, Italian
10
5
0
15
Sandbur
10



Sandbur
10
10
10
10
Smartweed
10



Smartweed
—
—
10
—
Soybean
20



Soybean
50
25
30
50
Waterhemp
80



Waterhemp
—
90
90
—
Waterhemp, Res2
75



Waterhemp, Res2
85
—
90
90
Waterhemp, Res1
70



Waterhemp, Res1
90
—
90
95













Compounds

















250 g ai/ha
139
146
148
153
154
155
169
171
172
174










Preemergence

















Arrowleaf Sida
0
10
0
65
0
75
5
60
100
25


Barnyardgrass
98
20
98
100
100
100
95
100
100
100


Beggarticks
0
0
0
—
15
80
5
0
25
0


Cocklebur
—
—
—
—
0
40
—
—
5
0


Corn
5
0
5
10
5
15
0
5
15
0


Crabgrass, Brazil
—
—
100
100
100
100
100
100
100
100


Crabgrass, Large
100
100
100
100
100
100
100
100
100
100


Dayflower, VA
65
35
90
95
90
60
75
30
90
5


Field Bindweed
20
25
50
100
95
100
80
5
95
5


Foxtail, Giant
100
100
100
100
100
100
100
100
100
100


Foxtail, Green
100
100
100
100
100
100
100
100
100
100


Goosegrass
100
98
100
100
100
100
100
100
100
100


Johnsongrass
100
100
40
100
98
100
80
75
100
70


Kochia
98
98
98
100
98
100
98
98
100
98


Lambsquarters
98
98
100
98
98
98
100
98
98
98


Morningglory
20
25
70
65
—
—
40
65
5
20


Nightshade
100
100
98
100
100
100
100
5
100
35


Nutsedge, Yellow
0
0
35
10
0
30
25
0
25
35


Panicum, Fall
100
100
100
100
100
100
100
100
100
100


Pigweed, Palmer
—
100
100
100
100
100
100
100
100
100


Poinsettia, Wild
80
40
100
98
85
100
98
10
98
30


Ragweed
0
25
75
80
40
80
100
—
—
—


Ryegrass, Italian
95
25
100
95
100
95
100
50
100
80


Sandbur
40
70
100
100
100
100
75
50
100
70


Smartweed
—
—
90
—
—
—
95
5
98
50


Soybean
35
0
40
25
25
30
20
20
20
0


Surinam Grass
75
35
98
98
90
90
100
30
98
50


Velvetleaf
65
25
65
100
100
98
100
50
100
35


Waterhemp
100
100
100
100
100
100
100
100
100
100












Compounds



















125 g ai/ha
139
142
146
148
153
154
155
169
171
172
174
196










Preemergence



















Arrowleaf Sida
0
35
0
0
25
0
40
5
30
95
25
15


Barnyardgrass
10
80
10
20
75
90
30
60
80
100
35
100


Beggarticks
0
75
0
0
65
0
70
5
0
25
0
65


Cocklebur
0
—
—
0
—
—
40
—
—
—
—
0


Corn
0
0
0
0
0
5
15
0
0
15
0
30


Crabgrass, Brazil
—
—
—
100
100
100
100
100
100
100
100
—


Crabgrass, Large
100
100
98
100
100
100
100
100
100
100
95
100


Dayflower, VA
60
70
35
65
80
70
35
65
30
70
5
65


Field Bindweed
0
98
0
20
100
35
95
20
5
95
5
65


Foxtail, Giant
98
100
98
100
100
100
100
100
100
100
90
100


Foxtail, Green
100
100
100
100
100
100
100
100
100
100
95
100


Goosegrass
98
100
75
100
100
100
100
100
100
100
—
100


Johnsongrass
98
30
70
30
100
50
90
50
65
75
30
98


Kochia
90
95
50
95
100
95
98
98
15
100
10
100


Lambsquarters
90
98
98
100
98
98
98
98
65
98
65
98


Morningglory
5
35
0
50
65
—
—
40
35
5
0
70


Nightshade
100
98
65
98
100
90
100
100
5
100
—
100


Nutsedge, Yellow
0
0
0
20
10
0
25
25
0
25
20
75


Panicum, Fall
100
100
100
100
100
100
100
100
100
100
100
100


Pigweed, Palmer
—
—
100
100
100
100
100
100
100
100
98
—


Poinsettia, Wild
75
70
40
20
70
25
80
40
10
50
20
75


Ragweed
0
40
0
75
20
0
50
60
—
—
—
50


Ryegrass, Italian
30
100
20
95
65
70
85
100
25
100
50
100


Sandbur
35
70
25
70
95
98
100
65
50
70
5
98


Smartweed
—
—
—
75
—
—
—
40
0
50
0
—


Soybean
0
25
0
20
5
25
30
—
0
20
0
35


Surinam Grass
75
60
20
98
75
70
90
75
10
35
5
100


Velvetleaf
0
75
0
25
98
40
98
60
15
80
15
95


Waterhemp
100
100
100
100
100
100
100
100
100
100
98
100












Compounds



















62 g ai/ha
139
142
146
148
153
154
155
162
169
171
174
196










Preemergence



















Arrowleaf Sida
0
30
0
0
25
0
10
0
0
15
0
15


Barnyardgrass
10
30
10
0
10
85
30
30
20
5
5
70


Beggarticks
0
65
0
0
35
0
40
0
0
0
0
50


Cocklebur
0
0
—
—
0
0
0
0
0
0
—
0


Corn
0
0
0
0
0
0
10
0
0
0
0
5


Crabgrass, Brazil
—
—
—
100
100
100
100
100
100
100
100
—


Crabgrass, Large
95
98
98
100
100
100
100
100
100
98
95
100


Dayflower, VA
30
50
10
40
40
25
20
65
10
0
0
50


Field Bindweed
0
75
0
0
65
5
85
5
—
0
0
—


Foxtail, Giant
85
100
90
100
100
100
98
100
100
100
70
98


Foxtail, Green
98
98
50
100
100
100
100
100
100
95
75
100


Goosegrass
80
100
70
100
98
95
100
100
100
100
98
100


Johnsongrass
90
—
60
20
50
25
90
20
20
10
30
95


Kochia
35
85
30
90
95
85
70
98
95
5
0
100


Lambsquarters
65
98
40
98
98
75
98
98
98
35
0
95


Morningglory
0
25
0
30
30
—
—
30
30
5
0
70


Nightshade
75
98
65
0
100
10
98
95
100
5
0
100


Nutsedge, Yellow
0
0
0
0
0
0
10
35
—
0
0
10


Panicum, Fall
100
100
90
100
100
100
100
100
100
100
85
100


Pigweed, Palmer
—
—
100
100
100
100
100
100
100
95
75
—


Poinsettia, Wild
35
35
20
0
40
25
40
10
30
0
0
65


Ragweed
0
30
0
0
5
0
5
95
5
—
—
50


Ryegrass, Italian
30
70
15
65
20
10
75
95
5
0
0
75


Sandbur
5
50
10
15
40
80
95
50
20
10
5
90


Smartweed
—
—
—
0
—
—
—
95
40
0
0
—


Soybean
0
0
0
20
0
20
30
25
20
0
0
20


Surinam Grass
5
5
0
75
10
50
70
30
70
5
5
25


Velvetleaf
0
65
0
0
65
30
60
35
0
0
0
75


Waterhemp
100
100
98
100
100
98
100
100
98
—
98
100












Compounds



















31 g ai/ha
139
142
146
148
153
154
162
169
171
172
174
196










Preemergence



















Arrowleaf Sida
0
30
0
0
5
0
0
0
0
30
0
15


Barnyardgrass
10
5
0
0
10
5
30
0
5
70
0
40


Beggarticks
0
40
0
0
25
0
0
0
0
15
0
50


Cocklebur
—
0
—
0
—
—
0
0
0
—
—
0


Corn
0
0
0
0
0
0
0
0
0
0
0
0


Crabgrass, Brazil
—
—
—
100
100
100
100
100
98
100
80
—


Crabgrass, Large
95
20
75
100
95
98
95
98
98
100
85
100


Dayflower, VA
5
5
0
40
10
0
35
5
0
40
0
35


Field Bindweed
0
50
0
0
65
0
5
0
0
5
0
25


Foxtail, Giant
40
75
20
95
85
65
100
100
60
100
5
98


Foxtail, Green
35
75
20
100
75
75
100
100
50
75
50
85


Goosegrass
70
70
40
98
95
95
100
95
80
98
50
75


Johnsongrass
75
5
50
20
10
20
20
0
0
50
0
65


Kochia
0
80
5
90
75
25
70
95
0
20
0
10


Lambsquarters
20
65
0
50
65
30
98
30
0
50
0
80


Morningglory
0
0
0
30
30
—
30
0
0
0
0
30


Nightshade
35
80
10
0
50
10
—
80
0
5
0
95


Nutsedge, Yellow
0
0
0
0
0
0
35
20
0
25
0
0


Panicum, Fall
25
65
5
85
100
90
100
100
65
75
65
98


Pigweed, Palmer
—
—
100
90
100
100
100
100
0
100
0
—


Poinsettia, Wild
20
10
20
0
25
0
10
0
0
20
0
50


Ragweed
0
0
0
0
5
0
70
0
—
—
—
0


Ryegrass, Italian
5
65
10
0
5
0
80
0
0
35
0
75


Sandbur
5
5
0
0
35
30
15
20
5
5
5
5


Smartweed
—
—
—
0
—
—
0
0
0
5
0
—


Soybean
0
0
0
0
0
0
25
0
0
0
0
20


Surinam Grass
0
5
0
40
5
10
—
65
0
20
0
15


Velvetleaf
0
0
0
0
50
20
0
0
0
0
0
20


Waterhemp
100
98
75
90
100
60
100
80
95
98
65
98












Compounds


















16 g ai/ha
139
142
146
148
153
154
162
169
171
174
196










Preemergence


















Arrowleaf Sida
0
0
0
0
5
0
0
0
0
0
0


Barnyardgrass
0
0
0
0
5
0
20
0
0
0
25


Beggarticks
0
0
0
0
0
0
0
0
0
0
50


Cocklebur
—
0
—
—
0
0
—
0
0
—
—


Corn
0
0
0
0
0
0
0
0
0
0
0


Crabgrass, Brazil
—
—
—
100
98
75
100
100
0
0
—


Crabgrass, Large
30
—
0
95
80
50
0
98
75
50
75


Dayflower, VA
0
0
0
0
5
0
35
0
0
0
35


Field Bindweed
0
20
0
0
5
0
5
0
0
0
0


Foxtail, Giant
0
35
20
25
40
5
70
70
40
0
85


Foxtail, Green
10
20
20
35
50
40
80
98
20
35
75


Goosegrass
5
40
0
25
80
10
95
50
70
35
60


Johnsongrass
0
0
0
0
0
0
20
0
0
0
65


Kochia
0
20
0
0
25
5
—
0
0
0
5


Lambsquarters
0
0
0
0
0
0
98
0
0
0
70


Morningglory
0
0
0
0
0
—
20
0
0
0
30


Nightshade
20
65
0
0
50
0
5
0
0
0
95


Nutsedge, Yellow
0
0
0
0
0
0
35
0
0
0
0


Panicum, Fall
0
25
0
75
5
15
100
65
0
0
—


Pigweed, Palmer
—
—
85
0
98
100
98
35
0
0
—


Poinsettia, Wild
0
0
20
0
0
0
0
0
0
0
50


Ragweed
0
0
0
0
5
0
0
0
—
—
0


Ryegrass, Italian
0
5
0
0
5
0
35
0
0
0
40


Sandbur
0
5
0
0
5
0
5
0
0
0
5


Smartweed
—
—
—
0
—
—
0
0
0
0
—


Soybean
0
0
0
0
0
0
0
0
0
0
0


Surinam Grass
0
5
0
25
0
0
—
0
0
0
—


Velvetleaf
0
0
0
0
20
0
0
0
0
0
10


Waterhemp
70
98
25
30
65
50
90
60
0
0
95














Compounds

Compound













8 g ai/ha
162
196
4 g ai/ha
162











Preemergence













Arrowleaf Sida
0
0
Arrowleaf Sida
0



Barnyardgrass
20
0
Barnyardgrass
0



Beggarticks
0
0
Beggarticks
0



Cocklebur
0
—
Cocklebur
0



Corn
0
0
Corn
0



Crabgrass, Brazil
100
—
Crabgrass, Brazil
0



Crabgrass, Large
0
—
Dayflower, VA
0



Dayflower, VA
35
5
Field Bindweed
0



Field Bindweed
0
0
Foxtail, Giant
0



Foxtail, Giant
20
5
Foxtail, Green
0



Foxtail, Green
15
75
Goosegrass
0



Goosegrass
0
40
Johnsongrass
20



Johnsongrass
20
—
Kochia
30



Kochia
—
5
Lambsquarters
0



Lambsquarters
0
60
Morningglory
0



Morningglory
0
0
Nightshade
0



Nightshade
0
95
Nutsedge, Yellow
0



Nutsedge, Yellow
0
0
Panicum, Fall
0



Panicum, Fall
0
25
Pigweed, Palmer
0



Pigweed, Palmer
25
—
Poinsettia, Wild
0



Poinsettia, Wild
0
0
Ragweed
0



Ragweed
0
0
Ryegrass, Italian
0



Ryegrass, Italian
0
0
Sandbur
0



Sandbur
0
5
Smartweed
0



Smartweed
0
—
Soybean
0



Soybean
0
0
Surinam Grass
0



Surinam Grass
0
0
Velvetleaf
0



Velvetleaf
0
0
Waterhemp
50



Waterhemp
85
50










Test G
Seeds of smallflower umbrella sedge (CYPDI, Cyperus difformis) and ducksalad (HETLI, Heteranthera limosa) were sown on the soil surface in two separate quadrants of 11 cm tubs filled with steam pasteurized Tama soil. Simultaneously, plantings of barnyardgrass (ECHCG, Echinochloa crus-galli) and japonica rice (ORYSP, Oryza sativa) were established in separate “plug” flats. Plants were grown in a greenhouse using supplemental lighting to maintain a photoperiod of approximately 16 h; daytime and nighttime temperatures were approximately 27-30° C. and 19-22° C., respectively. After 8 days, barnyardgrass plants were transplanted to one of the remaining quadrants of the tub, and the water level was adjusted to a final depth of 3 cm. Herbicide application timing was targeted at the 2.0 to 2.5 leaf stage and the plants were treated with test chemicals formulated in a non-phytotoxic solvent. Treated plants and controls were maintained in a greenhouse for 14 days, after which time all species were compared to controls and visually evaluated. Plant response ratings are summarized in Tables G1 through G3, and 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 G1







Results from Compd. No. 16 Alone and in


Combination with Bensulfuron-Methyl (b2a)












Treatment
Rate (g/ha)
ORYSP
ECHCG
CYPDI
HETLI















b2a
16
0
60
90
90


b2a
31
0
68
90
95


b2a
62
0
75
93
98


Compd. No. 16
 8
10
25
85
0


Compd. No. 16
16
15
35
85
60


b2a + Compd.
16 + 8 
0
40
93
99


No. 16


b2a + Compd.
31 + 8 
8
58
97
100


No. 16


b2a + Compd.
62 + 8 
13
73
98
100


No. 16


b2a + Compd.
16 + 16
18
45
95
99


No. 16


b2a + Compd.
31 + 16
25
52
96
98


No. 16


b2a + Compd.
62 + 16
18
67
98
99


No. 16
















TABLE G2







Results from Compd. No. 129 Alone and in


Combination with Bensulfuron-Methyl (b2a)












Treatment
Rate (g/ha)
ORYSP
ECHCG
CYPDI
HETLI















b2a
32
0
60
90
90


b2a
64
0
68
90
95


b2a
125 
0
75
93
98


Compd. No. 129
16
0
0
0
0


Compd. No. 129
32
10
5
48
25


b2a + Compd.
32 + 16
0
47
99
99


No. 129


b2a + Compd.
64 + 16
5
60
98
99


No. 129


b2a + Compd.
125 + 16 
13
72
99
100


No. 129


b2a + Compd.
32 + 32
3
40
98
98


No. 129


b2a + Compd.
64 + 32
10
55
93
95


No. 129


b2a + Compd.
125 + 32 
17
68
94
98


No. 129
















TABLE G3







Results from Compd. No. 129 Alone and in Combination with


5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-(3-


methoxyphenyl)-3-(3-methoxypropyl)-4(3H)-pyrimidinone (b12a)













Rate






Treatment
(g/ha)
ORYSP
ECHCG
CYPDI
HETLI















Compd. No. 129
31
5
15
75
40


b12a
125
5
35
80
80


Cmpd. No. 129 +
31 + 125
13
93
95
100


b12a









Test H
Seeds of plant species selected from wheat (TRZAW, Triticum aestivum), barley (HORBW, Hordeum vulgare), Kochia (KCHSC, Kochia caoparia) blackgrass (ALOMY, Alopecurus myosuroides), canarygrass (PHAMI, Phalaris minor), Italian ryegrass (LOLMU, Lolium multiflorum) common lambsquarter (CHEAL, Chenopodium album), pigweed (AMARE, Amaranthus retroflexus), Common Chickweed (STEME, Stellaria media), Russian thistle (SASKR, Salsola iberica), Wild Buckwheat (POLCO, Polygonum convolvulus), Catchweed Bedstraw (GALAP, Galium aparine), Mustard (SINAR, Sinapisar arvensis), Henbit Deadnettle (LAMAM, Lamium amplexicaule), Wild Radish (RAPRA, Raphanus raphanistrum), Field Poppy (PAPRH, Papaver rhoeas), Field Violet (VIOAR, Viola arvennsis), Scentless Chamomile (MATIN Matricaria inodora) were planted into soil and treated post-emergence with test chemicals formulated in a non-phytotoxic solvent mixture. Plants were grown in a greenhouse using supplemental lighting to maintain a photoperiod of approximately 14 hours; daytime and nighttime temperatures were approximately 23°-29° and 16°-19° Celsius, respectively. Balanced fertilizer was applied through the watering system. Treated plants and controls were maintained in a greenhouse for 20 days, after which time all species were compared to controls and visually evaluated. Plant response ratings were calculated as the mean of three replicates (unless otherwise indicated), are summarized in Table G, and 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 H1





Results from Compd. No. 129 Alone and in Combination with Flupyrsulfuron-


methyl (b2b) and in Combination with Thifensulfuron-methyl (b2c)






















Treatment
Rate
TRZAW
HORBW
KCHSC
SASKR
STEME
CHEAL





Compd. No. 129
31
10
10
80
65
50
85


Compd. No. 129
62
15
15
85
80
70
80


Compd. No. 129
125
15
15
95
90
80
90


b2b
8
0
20
75
50
90
60


b2b
16
5
30
100
50
100
85


b2b
31
5
60
80
50
100
75


b2b
62
25
70
95
60
100
80


b2c
8
0
0
70
100
85
85


b2c
16
0
5
85
100
100
70


b2c
31
0
5
95
100
100
100


b2c
62
5
5
100
100
100
95


Compd. No. 129 + b2b
31 + 8 
10
35
90
50
95
80


Compd. No. 129 + b2b
31 + 16
10
35
95
50
100
85


Compd. No. 129 + b2b
31 + 31
15
70
90
95
100
95


Compd. No. 129 + b2b
31 + 62
25
75
95
60
100
95


Compd. No. 129 + b2b
62 + 8 
15
35
90
65
100
90


Compd. No. 129 + b2b
62 + 16
20
40
100
100
100
95


Compd. No. 129 + b2b
62 + 31
20
60
100
70
100
95


Compd. No. 129 + b2b
62 + 62
25
75
100
65
100
100


Compd. No. 129 + b2b
125 + 8 
15
35
90
90
100
95


Compd. No. 129 + b2b
125 + 16 
15
65
90
90
100
75


Compd. No. 129 + b2b
125 + 31 
25
75
95
90
95
95


Compd. No. 129 + b2b
125 + 62 
40
80
100
95
100
—


Compd. No. 129 + b2c
31 + 16
10
10
100
95
95
80


Compd. No. 129 + b2c
31 + 31
10
10
90
100
95
95


Compd. No. 129 + b2c
62 + 16
10
10
85
100
90
95


Compd. No. 129 + b2c
62 + 31
10
10
95
100
100
95


Compd. No. 129 + b2c
62 + 62
10
10
95
95
95
95


Compd. No. 129 + b2c
125 + 16 
15
20
100
100
100
100


Compd. No. 129 + b2c
125 + 31 
15
20
100
95
100
95


Compd. No. 129 + b2c
125 + 62 
15
20
100
95
100
—

















Treatment
Rate
POLCO
AMARI
SINAR
GALAP
LAMAM
RAPRA





Compd. No. 129
31
30
80
80
65
60
60


Compd. No. 129
62
25
90
95
60
70
85


Compd. No. 129
125
70
95
95
70
80
90


b2b
8
100
100
100
90
90
100


b2b
16
85
100
95
95
95
100


b2b
31
100
100
100
90
95
100


b2b
62
100
100
100
100
90
100


b2c
8
95
100
80
80
60
95


b2c
16
95
100
90
90
70
75


b2c
31
95
100
85
75
75
100


b2c
62
95
100
95
95
75
95


Compd. No. 129 + b2b
31 + 8 
100
100
95
95
95
100


Compd. No. 129 + b2b
31 + 16
90
100
100
95
95
100


Compd. No. 129 + b2b
31 + 31
100
100
100
100
95
100


Compd. No. 129 + b2b
31 + 62
100
100
100
100
90
100


Compd. No. 129 + b2b
62 + 8 
95
100
100
95
85
100


Compd. No. 129 + b2b
62 + 16
100
100
100
100
90
100


Compd. No. 129 + b2b
62 + 31
95
100
100
100
90
100


Compd. No. 129 + b2b
62 + 62
100
100
100
100
100
95


Compd. No. 129 + b2b
125 + 8 
95
100
100
100
85
100


Compd. No. 129 + b2b
125 + 16 
95
100
95
95
90
100


Compd. No. 129 + b2b
125 + 31 
95
100
100
100
90
100


Compd. No. 129 + b2b
125 + 62 
100
100
95
95
90
100


Compd. No. 129 + b2c
31 + 16
90
100
85
65
70
95


Compd. No. 129 + b2c
31 + 31
95
100
90
80
70
95


Compd. No. 129 + b2c
62 + 16
95
100
85
85
70
100


Compd. No. 129 + b2c
62 + 31
100
100
90
85
90
100


Compd. No. 129 + b2c
62 + 62
100
100
95
95
90
100


Compd. No. 129 + b2c
125 + 16 
95
100
95
80
85
95


Compd. No. 129 + b2c
125 + 31 
95
100
90
95
85
95


Compd. No. 129 + b2c
125 + 62 
100
100
95
100
85
95

















Treatment
Rate
PAPRH
VIOAR
MATIN
LOLMU
PHAMI
ALOMY





Compd. No. 129
31
85
60
0
10
15
5


Compd. No. 129
62
90
75
5
10
20
10


Compd. No. 129
125
90
90
10
15
60
30


b2b
8
100
50
90
60
40
100


b2b
16
90
75
95
60
55
100


b2b
31
100
70
100
65
85
100


b2b
62
95
95
95
80
90
100


b2c
8
70
80
95
20
10
10


b2c
16
75
85
90
50
60
45


b2c
31
100
75
100
70
70
60


b2c
62
100
95
100
90
90
65


Compd. No. 129 + b2b
31 + 8 
90
60
100
65
55
95


Compd. No. 129 + b2b
31 + 16
90
65
100
70
65
95


Compd. No. 129 + b2b
31 + 31
100
80
100
75
70
100


Compd. No. 129 + b2b
31 + 62
100
100
100
75
95
100


Compd. No. 129 + b2b
62 + 8 
85
95
95
50
25
95


Compd. No. 129 + b2b
62 + 16
90
70
95
60
55
95


Compd. No. 129 + b2b
62 + 31
90
85
95
65
70
100


Compd. No. 129 + b2b
62 + 62
95
85
95
85
95
95


Compd. No. 129 + b2b
125 + 8 
75
65
90
60
55
90


Compd. No. 129 + b2b
125 + 16 
85
70
95
70
60
95


Compd. No. 129 + b2b
125 + 31 
100
80
90
60
70
95


Compd. No. 129 + b2b
125 + 62 
90
85
95
90
85
95


Compd. No. 129 + b2c
31 + 16
70
75
80
10
25
15


Compd. No. 129 + b2c
31 + 31
75
75
90
20
35
45


Compd. No. 129 + b2c
62 + 16
80
90
90
20
60
40


Compd. No. 129 + b2c
62 + 31
80
75
95
65
75
50


Compd. No. 129 + b2c
62 + 62
95
80
95
65
90
60


Compd. No. 129 + b2c
125 + 16 
95
80
95
60
60
60


Compd. No. 129 + b2c
125 + 31 
95
80
100
60
75
65


Compd. No. 129 + b2c
125 + 62 
95
80
95
70
85
70

## Claims

1. A compound selected from Formula 1, N-oxides and salts thereof,




wherein
R1 is halogen, cyano, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C2-C6 alkylcarbonyloxy, C1-C4 hydroxyalkyl, SOn(R12), C2-C4 alkylthioalkyl, C2-C4 alkylsulfonylalkyl, C1-C4 alkylamino, C2-C4 dialkylamino, C3-C6 cycloalkyl or hydroxy;
A is a radical selected from the group consisting of




each Y1, Y2, Y3, Y4 and Y5 is independently N or CR2, provided no more than 3 of Y1, Y2, Y3, Y4 and Y5 are N;
each Y6, Y7 and Y8 is independently N or CR3, provided no more than 2 of Y6, Y7 and Y8 are N;
Z is O or S;
Q is C(R4)(R5), O, S or NR6;
J is phenyl substituted with 1 R7 and optionally substituted with up to 2 R8; or
J is a 6-membered aromatic heterocyclic ring substituted with 1 R7 and optionally substituted with up to 2 R8 on carbon ring members; or
J is a 5-membered aromatic heterocyclic ring substituted with 1 R9 on carbon ring members and R11 on nitrogen ring members; and optionally substituted with 1 R10 on carbon ring members;
each R2 is independently H, halogen, cyano, nitro, SF5, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C4 alkenyloxy, C3-C4 alkynyloxy or S(O)nR12;
each R3 is independently H, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy or S(O)nR2;
R4 is H, F, Cl, Br, cyano, C1-C4 alkyl, C1-C4 haloalkyl or CO2R13;
R5 is H, F, C1-C4 alkyl, OH or OR13; or
R4 and R5 are taken together with the carbon to which they are attached to form C(═O), C(═NOR13) or C(═N—N(R14)(R15));
R6 is H, C1-C4 alkyl or C1-C4 haloalkyl;
R7 is halogen, cyano, SF5, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy or S(O)nR12;
each R8 is independently halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy or S(O)nR12; or
R7 and R8 are taken together with two adjacent carbon atoms to form a 5-membered carbocyclic ring containing ring members selected from up to two O atoms and up to two S atoms, and optionally substituted on carbon atom ring members with up to five halogen atoms;
R9 is halogen, cyano, SF5, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy or S(O)nR12;
R10 is halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy or S(O)nR12;
R11 is C1-C4 alkyl or C1-C4 haloalkyl;
each R12 is independently C1-C4 alkyl or C1-C4 haloalkyl;
each R13 is independently H or C1-C4 alkyl;
R14 is C1-C4 alkyl or C1-C4 haloalkyl;
R15 is C1-C4 alkyl or C1-C4 haloalkyl; and
each n is independently 0, 1 or 2;
provided
i) when R1 is CH3; A is A-1; Y1, Y2, Y3 and Y4 are each CH; and Y5 is CCF3 then J is other than 3-chloro-1H-1,2,4-thiadiazol-5-Y1,4-fluoro-2-pyridinyl, 4-chlorophenyl or 2,4-dichlorophenyl; and
ii) when R1 is CH3; A is A-1; Y1, Y2, Y3 and Y4 are each CH; and Y5 is CF then J is other than 4-fluoro-3-methylphenyl.

2. The compound of claim 1 wherein
R1 is halogen, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C2-C6 alkylcarbonyloxy, C1-C4 hydroxyalkyl, SOn(R12), C2-C4 alkylthioalkyl or C2-C4 alkylsulfonylalkyl;
A is a radical selected from the group consisting of A-1 and A-2;
each Y1, Y3, Y4 and Y5 is independently N or CR2; and Y2 is CR2;
each Y6 and Y7 is independently N or CR3; and Y8 is CR3;
Z is S;
Q is C(R4)(R5), O or S;
J is selected from the group consisting of













 t is 0, 1 or 2;
 u is 0 or 1;
each R2 is independently H, halogen, C1-C4 alkoxy, C1-C4 alkyl or C1-C4 haloalkyl;
each R3 is independently H, halogen or C1-C4 haloalkyl;
R4 is H, F, Cl, Br or C1-C4 alkyl;
R5 is H, F or OH; or
R4 and R5 are taken together with the carbon to which they are attached to form C(═O);
R7 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy;
R8 is independently halogen or C1-C4 haloalkyl; or
R7 and R8 are taken together with two adjacent carbon atoms to form a 2,2-difluorodioxolane ring;
R9 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy;
R10 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy;
R11 is C1-C4 alkyl or C1-C4 haloalkyl;
each R12 is independently C1-C4 alkyl;
each R13 is independently CH3 or CH2CH3;
R14 is C1-C4 alkyl;
R15 is C1-C4 alkyl; and
n is 0 or 2.

3. The compound of claim 2 wherein
R1 is halogen, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C1-C4 alkyl, C1-C4 haloalkyl or C2-C4 alkenyl;
each Y1 and Y5 is independently N or CR2; and each Y2, Y3 and Y4 is CR2;
each Y6 and Y7 is N; and Y8 is CR3;
Q is C(R4)(R5) or O;
J is selected from J-1, J-2, J-3, J-4, J-5, J-6, J-7, J-9, J-12, J-17, J-18, J-20, J-22, J-26, J-29 and J-30;
t is 0 or 1;
u is 0;
each R2 is independently H, halogen, C1-C4 alkyl or C1-C4 haloalkyl;
each R3 is independently H, F, Cl or CF3;
R4 is H, F or CH3;
R5 is H or F;
R7 is F, CH3 or CF3;
R8 is independently F, Cl or CF3;
R9 is halogen, C1-C4 alkyl or C1-C4 haloalkyl;
R10 is halogen, C1-C4 alkyl or C1-C4 haloalkyl;
R11 is C1-C4 alkyl;
each R12 is CH3; and
each R13 is CH3.

4. The compound of claim 2 wherein
R1 is halogen, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C1-C4 alkyl or C1-C4 haloalkyl;
A is A-1;
Y1 is N or CR2; and each Y2, Y3, Y4 and Y5 is independently CR2;
Q is C(R4)(R5);
J is selected from J-1, J-2, J-10, J-17, J-18 and J-20;
t is 0;
each R2 is independently H, F, Cl, CH3 or CF3;
R4 is H;
R5 is H; and
R7 is F or CF3.

5. The compound of claim 3 wherein
R1 is C1-C4 alkoxy, C1-C4 haloalkoxy or C1-C4 alkyl;
A is A-1;
Y1 is N or CR2; and each Y2, Y3, Y4 and Y5 is independently CR2;
Q is O;
J is selected from J-1, J-2, J-17 and J-18;
each R2 is independently H, F, Cl or CF3; and
R7 is CF3.

6. The compound of claim 3 wherein
R1 is CH3;
each Y1, Y2, Y3, Y4 and Y5 is independently CR2;
J is J-2; and
each R2 is independently H or F.

7. The compound of claim 1 selected from the group consisting of
4-[[2-(4-fluorophenyl)-5-methyl-2H-1,2,3-triazol-4-yl]oxy]-2-(trifluoromethyl)pyridine and
4-[[5-Methoxy-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine.

8. The compound of claim 1 selected from the group consisting of
4-[[2-(4-fluorophenyl)-5-methyl-2H-1,2,3-triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine;
4-[[2-(4-fluorophenyl)-5-methyl-2H-1,2,3-triazol-4-yl]oxy]-2-(trifluoromethyl)pyridine;
4-[[5-ethoxy-2-(4-fluorophenyl)-2H-1,2,3-triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine;
4-[[5-methoxy-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine;
4-[[5-methyl-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine;
4-[[5-ethoxy-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine; and
4-[[5-(2,2,2-trifluoroethoxy)-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine.

9. 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.

10. 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.

11. A herbicidal mixture comprising (a) a compound of Formula 1, N-oxides, and salts thereof from claim 1, 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, (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, difenzoquat, bromobutide, flurenol, cinmethylin, cumyluron, dazomet, dymron, methyldymron, etobenzanid, fosamine, fosamine-ammonium, metam, oxaziclomefone, oleic acid, pelargonic acid and pyributicarb, and (b16) herbicide safeners;
and salts of compounds 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 solenesyltransererase (HST) inhibitors, (b14) cellulose biosynthesis inhibitors, (b15) other herbicides including mitotic disruptors, organic arsenicals, asulam, difenzoquat, bromobutide, flurenol, cinmethylin, cumyluron, dazomet, dymron, methyldymron, etobenzanid, fosamine, fosamine-ammonium, metam, oxaziclomefone, oleic acid, pelargonic acid and pyributicarb, and (b16) herbicide safeners.

12. 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.