HERBICIDAL SULFONAMIDES

Abstract: Compounds of formula (I), and their N-oxides and agriculturally suitable salts, are disclosed which are useful for controlling undesired vegetation. In said formula (I) J is J-1 - J-19, R<2> is C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C3-C6 alkoxyalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C2-C6 cyanoalkyl, C1-C6 nitroalkyl, (CH2)p-OR<6>, CH=CH(CH2)q-OR<6>, CC(CH2)q-OR<6>, C2-C6 alkylthioalkyl, C2-C6 alkylsulfinylalkyl, C2-C6 alkylsulfonylalkyl, C3-C8 alkoxycarbonylalkyl, C3-C8 alkylcarbonyloxyalkyl or oxiranyl optionally substituted with 1-3 C1-C3 alkyl; also disclosed are compositions containing the compounds of formula (I) and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective amount of a compound of formula (I).

Description: TITLE HERBICIDAL SULFONAMIDES BACKGROUND OF THE INVENTION This invention relates to certain sulfonamides, their N-oxides, agriculturally suitable salts and compositions, and methods of their use for controlling undesirable vegetation. 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, corn (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 which are more effective, less costly, less toxic, environmentally safer or have different modes of action. U.S. 4,818,275 discloses herbicidal acyclic sulfonamides of the formula wherein, inter alia X and Y are Br, Cl or F; R is alkyl, haloalkyl or dialkylamino; R 1 is H, Νa, lower alkyl or SO 2 R; R 2 is alkyl, haloalkyl or lower alkoxy; and R 3 is halogen, alkyl or haloalkyl. The sulfonamides of the present invention are not disclosed therein. SUMMARY OF THE INVENTION This invention is directed to compounds of Formula I including all geometric and stereoisomers, N-oxides, and agriculturally suitable salts thereof, agricultural compositions containing them and their use for controlling undesirable vegetation: I wherein X is H, F or Cl; Y is F, Cl, Br, cyano, nitro, C1-C3 haloalkyl, C r C 3 alkoxy, C1-C3 haloalkoxy or C(S)NH 2 ; R 1 is H, C r C 6 alkyl, C r C 6 haloalkyl, C r C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 2 -C β alkoxyalkyl, C 2 -C 6 haloalkoxy alkyl, formyl, 2 -C 2 o alkylcarbonyl, C -C 7 cycloalkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C6 alkoxycarbonyl, C 3 -C 6 alkoxyalkylcarbonyl, C 2 -C 6 haloalkoxycarbonyl, C3-C6 cycloalkyl, C 3 -C 6 halocycloalkyl, C4-C7 cycloalkylalkyl, C 4 -C 7 halocycloalkylalkyl, S(O) 2 R 2 , C(O)SR 3 , C(O)NR 4 R 5 or benzoyl; R 2 is Cj-Cg alkoxy, C r C 6 haloalkoxy, C r C 6 haloalkyl, C 3 -C 6 cylcloalkyl, C 3 -C 6 halocycloalkyl, C -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 6 alkoxyalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 2 -C 6 cyanoalkyl, C r C 6 nitroalkyl, (CH 2 ) p -OR6, CH=CH(CH 2 ) q -OR6, C≡C(CH 2 ) q -OR6, C 2 -C 6 alkylthioalkyl, C 2 -C 6 alkylsulfmylalkyl, C 2 -C 6 alkylsulfonylalkyl, C 3 -C 8 alkoxycarbonylalkyl, C 3 -C 8 alkylcarbonyloxy- alkyl or oxiranyl optionally substituted with 1-3 C j -C 3 alkyl; R 3 is H, C1-C3 alkyl or C1-C3 haloalkyl; or R 3 is phenyl optionally substituted with C1-C3 alkyl, 1-3 halogen, 4-5 fluorine, 1-2 nitro, C r C 3 alkoxy or CF 3 ; R 4 is H, C1-C3 alkyl or C r C 3 haloalkyl; or R 4 is phenyl optionally substituted with C1-C3 alkyl, 1-3 halogen, 4-5 fluorine, 1-2 nitro, C1-C3 alkoxy or CF 3 ; R 5 is C r C 3 alkyl or C r C 3 haloalkyl; or R 4 and R 5 are taken together as -CH-CH 2 -, -CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH2-, -CH 2 CH 2 CH 2 CH 2 CH 2 - or -CH 2 CH 2 OCH 2 CH 2 -; R 6 is C r C 3 alkylsulfonyl, C,-C 3 haloalkylsulfonyl or P(=O)(OR 7 )(OR 8 ); or R 6 is phenylsulfonyl optionally substituted with C r C 6 alkyl, 1-3 halogen, 4-5 fluorine, C r C 6 alkoxy, CF 3 or C 2 -C 4 alkylcarbonyl; R 7 and R 8 are each independently H, C r C 3 alkyl or C1-C3 haloalkyl; J-17 J-18 J-19 wherein the dashed line in J-l, J-5, J-6, J-18, and J-19 indicates that the left-hand ring contains only single bonds or one bond in the ring is a carbon-carbon double bond; m and n are each independently 0, 1 , 2 or 3, provided that m + n is 2 or 3; Z is CR R1 0 , o, S, S(O), S(O) 2 , N(C r C 4 alkyl) Z i is CR 9 R 23 , 0, S, S(O), S(O) 2 , N(C Γ C 4 alkyl) each R 9 is independently H, C Cg alkyl, halogen, hydroxy, C j -Cg alkoxy, Ci-Cg haloalkyl, Cj-Cg haloalkoxy, C 2 -Cg alkylcarbonyloxy or C 2 -Cg haloalky lcarbonyloxy ; each R 10 is independently H, C j -Cg alkyl, hydroxy or halogen; or when R 9 and R 10 are bonded to adjacent carbon atoms they can be taken together with the carbons to which they are attached to form optionally substituted with at least one member selected from 1-2 halogen and 1-2 C1-C 3 alkyl; each R 1 1 is independently H, C Cg alkyl, C 3 - alkenyl, C r C 6 haloalkyl or C 2 -C 6 alkoxyalkyl; R 12 is H, halogen, C r C 6 alkyl, C 3 -C 6 alkenyl, C r C 6 haloalkyl or C 2 -C 6 alkoxyalkyl; R 13 is H, C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, HC(=O), C 2 -C 5 alkylcarbonyl or N(R J 1 ) 2 ; Rl is C r C 6 alkyl, C r C 6 alkylthio, C r C 6 haloalkyl or N(CH 3 ) 2 ; W is N or CR 15 ; R 15 is H, Ci-Cg alkyl or halogen; or R 15 is phenyl optionally substituted with Ci-Cg alkyl, 1-3 halogen, 4-5 fluorine, Cj-Cg alkoxy or CF 3 ; R 16 is C r C 6 alkyl, halogen or C r C 6 haloalkyl; R 17 and R 18 are each independently H, Cj-Cg alkyl or Cj-Cg haloalkyl; R 19 and R 20 are each independently C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl or C 3 -C 6 haloalkynyl; R 21 is H, halogen, cyano, C1-C3 alkoxy or C1-C3 haloalkoxy; R 22 is C j -Cg alkyl or C Cg haloalkyl; or R 22 is phenyl optionally substituted with Ci-Cg alkyl, 1-3 halogen, 4-5 fluorine, 1-2 nitro, Ci-Cg alkoxy or CF 3 ; R 23 is C1-C3 alkyl, hydroxy or halogen; R 24 is cyano or C(Q)R 25 ; R 25 is 0 R 2 6 or NR 27 R 28 ; R 26 is C r C 6 alkyl or C r C 6 haloalkyl; each R 27 is independently H or Cj-Cg alkyl; R 28 is H, C r C 6 alkyl, C r C 6 alkoxy or NR 2 R 29 ; or R 27 and R 28 can be taken together as -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 CH 2 - or -CH 2 CH 2 OCH 2 CH 2 -; R 29 is H, C r C 3 alkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 alkoxycarbonyl or C r C 3 alkylsulfonyl; Q is independently O or S; Q 1 is O or S; p is 1, 2 or 3; and q is O, 1, 2 or 3; provided that, (a) when J is J-5, X is F, Y is Cl, R 1 is H, Q is O, R 9 and R 10 are H, Z 1 is O, n is 2, and m is 1, then R 2 is other than CF3; (b) when J is J-6, X is F, Y is Cl, R 1 is H, Q is O, R 9 and R 10 are H, Z is CHCl or CHBr, n is 1, and m is 1, then R 2 is other than CF3; (c) when J is J-8, X is F, Y is Cl, R 1 is H, R 17 and R 18 are H, Q is O, R 9 and R 10 are H, Z is CH 2 , and (m+n) is 2 or 3, then R 2 is other than CF 3 ; (d) when J is J-8, X is F, Y is Cl, R 1 is H, R 17 and R 18 are H, Q is O, R 9 and R 10 are H, Z is O, n is 1, and m is 2, then R 2 is other than CF3; and (e) when J is J-l 1, X is F, Y is Cl, R 1 is H, R 21 is Cl, R 9 and R 10 are H, Z is CH 2 , and (m+n) is 3, then R 2 is other than CF 3 . 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, Ai-propyl, -propyl, or the different butyl, pentyl or hexyl isomers. The term "1-2 alkyl" indicates that one or two of the available positions for that substituent may be alkyl which are independently selected. "Alkenyl" includes straight-chain or branched alkenes such as vinyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. "Alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. "Alkynyl" includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. "Alkynyl" can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. "Alkoxy" includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. "Alkoxyalkyl" denotes alkoxy substitution on alkyl. "Alkoxyalkoxy" denotes alkoxy substitution on alkoxy. Examples of "alkoxyalkyl" include CH 3 OCH 2 , CH 3 OCH 2 CH 2 , CH 3 CH 2 OCH 2 , CH 3 CH 2 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 . "Alkylthio" includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. "Alkylthioalkyl" denotes alkylthio substitution on alkyl. Examples of "alkylthioalkyl" include CH 3 SCH 2 , CH 3 SCH 2 CH 2 , CH 3 CH 2 SCH 2 , CH 3 CH 2 CH 2 CH 2 SCH 2 and CH 3 CH 2 SCH 2 CH 2 . "Alkylsulfinyl" includes both enantiomers of an alkylsulfinyl group. Examples of "alkylsulfinyl" include CH 3 S(O), CH 3 CH 2 S(O), CH 3 CH 2 CH 2 S(O), (CH 3 ) 2 CHS(O) and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers. Examples of "alkylsulfonyl" include CH 3 S(O) 2 , CH 3 CH 2 S(O) 2 , CH 3 CH 2 CH 2 S(O) 2 , (CH 3 ) 2 CHS(O) 2 and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers. "Cyanoalkyl" denotes an alkyl group substituted with one cyano group. Examples of "cyanoalkyl" include NCCH 2 , NCCH 2 CH 2 and CH 3 CH(CN)CH 2 . "Alkylamino", "dialkylamino", and the like, are defined analogously to the above examples. "Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. 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. The term "halogen", either alone or in compound words such as "haloalkyl", includes fluorine, chlorine, bromine or iodine. The term "1-2 halogen" indicates that one or two of the available positions for that substituent may be halogen which are independently selected. Further, when used in compound words such as "haloalkyl", said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of "haloalkyl" include F 3 C, C1CH 2 , CF 3 CH 2 and CF 3 CC1 2 . The terms "haloalkenyl", "haloalkynyl", "haloalkoxy", and the like, are defined analogously to the term "haloalkyl". Examples of "haloalkenyl" include (C1) 2 C=CHCH 2 and CF 3 CH 2 CH=CHCH 2 . Examples of "haloalkynyl" include HG≡CCHCl, CF 3 C≡C, CC1 3 C≡C and FCH 2 C≡CCH 2 . Examples of "haloalkoxy" include CF 3 O, CCl 3 CH 2 O, HCF 2 CH 2 CH 2 O and CF 3 CH 2 O. Examples of "haloalkylthio" include CC1 3 S, CF 3 S, CC1 3 CH 2 S and C1CH 2 CH 2 CH 2 S. Examples of "haloalkylsulfinyl" include CF 3 S(O), CCl 3 S(O), CF 3 CH 2 S(O) and CF 3 CF 2 S(O). Examples of "haloalkylsulfonyl" include CF 3 S(O) 2 , CCl 3 S(O) 2 , CF 3 CH 2 S(O) 2 and CF 3 CF 2 S(O) 2 . Examples of "haloalkoxyalkoxy" include CF 3 OCH 2 O, ClCH 2 CH 2 OCH 2 CH 2 O, Cl 3 CCH 2 OCH 2 O as well as branched alkyl derivatives. The total number of carbon atoms in a substituent group is indicated by the "C j -C j " prefix where i and j are numbers from 1 to 20. For example, C1-C3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C 2 alkoxyalkyl designates CH 3 OCH 2 ; C 3 alkoxyalkyl designates, for example, CH 3 CH(OCH 3 ), CH 3 OCH 2 CH 2 or CH 3 CH 2 OCH 2 ; and C alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH 3 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 . Examples of "alkylcarbonyl" include C(O)CH 3 , C(O)CH 2 CH 2 CH 3 and C(O)CH(CH 3 ) 2 . Examples of "alkoxycarbonyl" include CH 3 OC(=O), CH 3 CH 2 OC(=O), CH 3 CH 2 CH 2 OC(=O), (CH 3 ) 2 CHOC(=O) and the different butoxy- or pentoxycarbonyl isomers. In the above recitations, when a compound of Formula I is comprised of one or more heterocyclic rings, all substituents are attached to these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen. When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1, said substituents (when they exceed 1) are independently selected from the group of defined substituents. Further, when the subscript indicates a range, e.g., (R) j _j, then the number of substituents may be selected from the integers between i and j inclusive. When a group contains a substituent which can be hydrogen, for example R 1 or R 13 , then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted. 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. Accordingly, the present invention comprises compounds selected from Formula I, N-oxides and agriculturally suitable salts thereof. The compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form. The salts of the compounds of the invention 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. The salts of the compounds of the invention also include those formed with organic bases (e.g., pyridine, ammonia, triethylamine or dicyclohexylamine) or inorganic bases (e.g., hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium) when the compound contains an acidic group such as a carboxylic acid or an amide. Preferred compounds for reasons of better activity and or ease of synthesis are: Preferred 1. Compounds of Formula I above, and N-oxides and agriculturally suitable salts thereof, wherein: X is F or Cl; Y is F. Cl or Br; R 1 is H, C r C 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C r C 6 haloalkyl, C 2 -C 6 alkoxyalkyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkoxyalkylcarbonyl, C -Cg alkylcarbonyl, C 2 -Cg alkoxycarbonyl, S(O) 2 R 2 or C(O)ΝR 4 R 5 ; R 2 is C ι -C 6 alkoxy, C 1 -C 6 haloalkoxy, C ι -C 6 haloalkyl, C 3 -C 6 cylcloalkyl, C 3 -Cg halocycloalkyl, C 2 -C 6 alkoxyalkyl or C 2 -C 6 haloalkoxy alkyl; J is J-5, J-6, J-l 1, J-17 or J-19; Z is CR 9 R ! 0, O, S or N(C r C 4 alkyl); each R 9 is independently H, halogen or C Cg haloalkoxy; each R 10 is independently H, hydroxy or halogen; each Q is O; Z 1 is CR 9 R 23 , O, S or N(C r C 4 alkyl); and R 23 is halogen. Preferred 2. Compounds of Preferred 1 wherein: Y is F or Cl; R 1 is H, C r C 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C r C 6 haloalkyl, C 2 -C 6 alkoxyalkyl, C 3 -C 6 haloalkenyl, C 2 -C 6 alkylcarbonyl or C 2 -Cg alkoxycarbonyl; R 2 is C r C 6 haloalkoxy, C r C 6 haloalkyl, C 3 -C 6 halocycloalkyl, C 2 -C 6 alkoxyalkyl or C 2 -Cf5 haloalkoxyalkyl; Z is CR 9 R'0 O r O; and Z' is CR 9 R 2 or O. Preferred 3. Compounds of Preferred 1 wherein: J is J-19; R 1 is H, C r C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 alkylcarbonyl or C 2 -C 6 alkoxycarbonyl; R 2 is C,-C 6 haloalkyl; R 9 is H; R 10 is hydroxy or halogen; Z is CR 9 R 10 ; n is 1 ; and m is l. Preferred 4. Compounds of Preferred 2 wherein: J is J-6; and Z is CR 9 R 10 . Most preferred are compounds of Preferred 4 selected from the group: a) (6S-cis)- 1 -chloro-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro- 1 ,3-dioxo- 1H- pyrrolo[ 1 ,2-c]imidazol-2(3H)-yl)phenyl]methanesulfonamide; b) (6S-cw)-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro- 1 ,3-dioxo- 1H- pyrrolof 1 ,2-c]imidazol-2(3H)-yl)phenyl]-N- [(chloromethyl)sulfonyl]acetamide; c) (65-C/5)- 1 -chloro-N-[2-chloro-5-(6-chlorotetrahydro- 1 ,3-dioxo- 1H- pyrrolo[ 1 ,2-c]imidazol-2(3H)-yl)-4-fluorophenyl]methanesulfonamide; d) (6S-cis)-N- [2-chloro-5-(6-chlorotetrahydro- 1 ,3-dioxo- lH-pyrrolo[ 1 ,2- c]imidazol-2(3H)-yl)-4-fluorophenyl)-N-[(chloromethyl)sulfonyl]acetamide; e) (65-c/5)- l-chloro-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro-l,3-dioxo-lH- pyrrolo[ 1 ,2-c]imidazol-2(3H)-yl)phenyl]methanesulfonamide monosodium salt; f) (6S-cis)- 1 -chloro-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro- 1 ,3-dioxo- 1H- pyrrolo[ 1 ,2-c]imidazol-2(3H)-yl)phenyl]methanesulfonamide monopotassium salt; g) (65-cw)-l-chloro-N-[2-chloro-5-(6-chlorotetrahydro-l,3-dioxo-lH- pyrrolo[ 1 ,2-c]imidazol-2(3H)-yl)-4-fluorophenyl]methanesulfonamide monosodium salt; and h) (6S-cis)- 1 -chloro-N-[2-chloro-5-(6-chlorotetrahydro- 1 ,3-dioxo- 1H- pyrrolo[ 1 ,2-c]imidazol-2(3H)-yl)-4-fluorophenyl]methanesulfonamide monopotassium salt. This invention also relates to herbicidal compositions comprising herbicidally effective amounts of the compounds of the invention and at least one of a surfactant, a solid diluent or a liquid diluent. The preferred compositions of the present invention are those which comprise the above preferred compounds. 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). The preferred methods of use are those involving the above preferred compounds. DETAILS OF THE INVENTION The compounds of Formula I can be prepared by one or more of the following methods and variations as described in Schemes 1-10. The definitions of X, Y, J, R!-R 29 , Z, Z 1 , n, m, W, Q, Q 1 , p, and q in the compounds of Formulae 1-23 below are as defined above in the Summary of the Invention. Compounds of Formulae Ia-If are various subsets of the compounds of Formula I, and all substituents for Formulae Ia-If are as defined above for Formula I. Compounds of Formula I are prepared from the corresponding anilines of Formula 1 as represented in Scheme 1. Scheme 1 Synthesis of Anilines of Formula 1 Anilines of Formula 1 are prepared by the method illustrated in Scheme 2. Nitration of acetanilide 2 using a nitric acid/sulfuric acid mixture affords the nitro compound of Formula 3. Reduction of the nitro group affords the aniline of Formula 4. The aniline of Formula 4 is contacted with a sulfonyl chloride to give the sulfonamide of Formula 5. For compounds wherein R 1 is other than H, the sulfonamide nitrogen can be alkylated, acylated or sulfonylated to give the R la -substituted compound of Formula 1. The alkylation is performed using an alkyl halide or alkyl sulfonate in the presence of a base such as potassium carbonate, sodium methoxide, potassium t-butoxide (t-BuOK) or sodium hydride in an anhydrous solvent such as dimethylformamide (DMF), tetrahydrofuran or acetonitrile at ambient temperature to 80 °C. Acylations to form the carbonyl-substituted sulfonamides are accomplished by condensing the sulfonamide of Formula 5 with the appropriate acylating agent, for example an acyl chloride, isocyanate or carbamoyl chloride. Sulfonylations to form the sulfonyl-substituted sulfonamides are accomplished in an analogous manner by reacting the sulfonamide of Formula 5 with the appropriate sulfonylating agent, for example a sulfonyl chloride. Scheme 2 R S0 C1 pyridine or sulfonylation G = Br, I, OS(0)2(4-CH3-Ph), Rla = Rl except H OS(0) 2 CH 3 Anilines of Formula 1 can also be prepared by the method illustrated in Scheme 3. The nitro aniline of Formula 6 is sulfonylated to afford the compound of Formula 7. Further alkylation, acylation or sulfonylation gives the nitro compound of Formula 8, which is reduced to the aniline of Formula 9. Chlorination of the phenyl ring provides the compound of Formula 1 wherein R , a is R 1 as defined in the Summary of the Invention except H. Scheme 3 G = Br, I, OS(0) 2 (4-CH3-Ph), OS(0) 2 CH 3 l cxce p t H Converting Anilines of Formula 1 to Compounds of Formula I The anilines prepared by the methods outlined in Schemes 2 and 3 are used in the condensation with J group derivatives to form compounds of Formula I. In some instances, the anilines are used directly in the condensation reactions. In other instances and depending on the nature of the J-group, the NH 2 of the aniline is first converted to another functional group prior to condensation. For example, the aniline may be converted first to a hydrazine, an isocyanate or an aryl iodide. These methods are described in more detail below. Direct Coupling with the Anilines In some instances where the aniline is used directly, the compounds of Formula I are prepared by condensation of the aniline with an anhydride precursor to the J group. For example, as illustrated in Scheme 4, the anhydride of Formula 10 is condensed with the aniline of Formula 1 to give compounds of Formula Ia wherein J = J-l. This method is disclosed in EP-A-170,191. Scheme 4 Ia The anhydride of Formula 10 can be prepared by methods disclosed in EP 493,721, and WO 91/06216. Compounds of Formula I wherein J = J-8 and J-12 can be prepared using similar methodology. The aniline is condensed with the appropriate J-group anhydride, diester, or other bis-electrophile to form the compound of Formula I. The J-8 group precursor and the aniline condensation reaction are described in WO 94/03459. The J-12 group anhydride and the aniline condensation reaction are described in U.S. 4,003,926. Hvdrazines For some compounds of Formula I, the appropriate aniline is first converted to the corresponding hydrazine, and then the hydrazine is condensed with the J-group derivative, or precursor thereof, to form the desired material. The conversion of an aniline of Formula 1 to a hydrazine of Formula 11 is illustrated in Scheme 5. Subsequent condensation of the hydrazine with the iminoether precursor to J-2 followed by cyclization with phosgene forms the sulfonamide of Formula lb. The preparation of the iminoether J-2 precursor and the condensation procedure is described in U.S.4,315,767. Scheme 5 11 lb Anilines can be converted to the hydrazines by diazotization and then reduction as is well-known in the literature (for example, see U.S. 4,695,312). Compounds of Formula I wherein J = J-7 are also prepared by first converting the aniline to the appropriate hydrazine, and then condensation with the appropriate J-group precursor. Methods for the preparation of the J-7 precursor and the condensation with a hydrazine are described in WO 92/12139 and U.S. 4,560,752. The retrosynthetic analysis for the synthesis of the J-2 group is shown below in Scheme 6 for compounds of Formula I wherein J = J-2 and Z is CR 9 Rl°. The formation of ring A can be accomplished by intramolecular cyclization between the nitrogen in ring B and the terminal double bond of the triazolinone with the sulfonamide group already in place. The synthesis of the triazolinone ring B is known in the art and can be prepared by methods such as those described in U.S. 4,818,275 and U.S. 4,818,276. Scheme 6 J-2 m = 1 or 2 Isocyanates In some instances, the appropriate aniline is first converted to the corresponding isocyanate, and then the isocyanate is condensed with the J-group derivative, or precursor thereof, to form compounds of Formula I. In Scheme 7, the conversion of aniline of Formula 1 to isocyanate of Formula 12 is illustrated. Subsequent condensation of the isocyanate with the aminoester of Formula 13 followed by cyclization forms the sulfonamide of Formula Ic. The preparation of some aminoester precursors to J-6 and the condensation procedure are described in U.S. 4,179,276. Scheme 7 Ic Q = 0 Compounds of Formula I wherein J = J-3, J-4, J-5, J-9, J-10 and J-19 are also prepared by first converting the aniline to the appropriate isocyanate, and then condensation with the appropriate J-group precursor. Methods for the preparation of the J-4 precursor and the condensation are described in WO 92/11244, EP 476,697, ZA 91/00466, JP 377,874, and U.S. 3,902,887. The synthesis of the J-5 precursor and the condensation with isocyanates is described in WO 92/13453 and EP 230,874. Methods for the preparation of the J-3 precursor and the condensation with isocyanates are described in EP 484,776. Methods for the preparation of the J-19 precursor and its condensation with isocyanates are described in EP 493,323. The synthesis of the J-10 precursor and the condensation with isocyanates is described in J. Pesticide Sci., (1993), 18, 309. In a similar vein, the imino compounds of Formula I wherein J = J-9 can be prepared from the corresponding isocyanates of the anilines. The condensation procedure and J-group precursor preparation for compounds containing J-9 are disclosed in EP 457, 151 , JP 4, 145,087, EP 480,871 and DE 3,927,388. One skilled in the art will recognize that when Q or Ql is S in the desired product, the appropriate isothiocyanate is used instead of the isocyanate in the synthesis. For some compounds of Formula I wherein J = J-3, J-4, J-5, J-6, J-10, and J-19, the coupling can also be accomplished starting with the aniline rather than the isocyanate. For example, the synthesis of compounds of Formula Id (compounds of Formula I wherein R 9 and R' 0 are taken together to form a cyclopropane ring) is illustrated in Scheme 8. Scheme 8 KOH ethanol 17 18 19 Id Treatment of cyclopropane dicarboxylic acid of Formula 14 with urea and heating to 175-185 °C affords the dicarboximide of Formula 15 as described by G. C. Crockett et al. in Synth. Commun. (1981), 11, 447-454. The diester of the diacid of Formula 14 is prepared by the method described by L. L. McCoy in J. Am. Chem. Soc, (1958), 80, 65-68. The diacid can be obtained by saponification of the diester using well-known methods. Reduction of the dicarboximide of Formula 15 with borane in an inert solvent, such as tetrahydrofuran (THF), followed by work-up with aqueous hydrochloric acid affords the azabicyclo[3. l.Ojhexane hydrochloride of Formula 16. The reduction is preferably conducted with heating, for example in THF at reflux, as described by H. C. Brown and P. Heim in J. Org. Chem., (1973), 38, 912-916. The amine hydrochloride of Formula 16 is converted via a five step sequence to the α-aminoacid of Formula 20 as illustrated. Purification of the intermediates is not necessary. Neutralization of the amine hydrochloride with a base, such as concentrated aqueous potassium hydroxide, liberates the free amine. Dissolution of the amine in an inert solvent, such as diethyl ether, and treatment with a solution of N-chlorosuccinimide (ΝCS) in an inert solvent such as ether, produces the chloramine of Formula 17. The solution of the chloramine is then treated with ethanolic potassium hydroxide to effect dehydrochlorination and give the imine of Formula 18. Once again, the imine is not purified but treated directly first with aqueous sodium bisulfite, and then with solid sodium cyanide to afford the aminonitrile of Formula 19. The reaction mixture is poured into water and extracted with a water-immiscible solvent such as ether. The organic layers are dried and evaporated under reduced pressure to afford the aminonitrile. No additional purification is necessary. The aminonitrile can be converted to the aminoacid of Formula 20 by hydrolysis with aqueous barium hydroxide followed by neutralization with sulfuric acid. A mixture of epimers at the carboxylic acid centers is obtained, and the individual diastereomers can be separated by chromatography. The acid of Formula 20 is reacted with the aniline of Formula 1 and a trialkylaluminum reagent (e.g., trimethylaluminum), in a non-coordinating solvent such as an aromatic hydrocarbon (e.g., benzene and toluene) or halogenated hydrocarbon (e.g., methylene chloride, chloroform, and dichloroethane) to obtain the amide. Generally, the reaction requires 0.1 to 48 hours at a temperature of 0 °C to 25 °C to proceed to completion. The amides are isolated by extraction into an organic solvent, aqueous wash, and removal of the solvent under reduced pressure. Purification can be accomplished by chromatography or recrystallization. The condensation with the amine can also be performed starting with the ester of the acid of Formula 20. The tricyclic imide of Formula Id can be prepared from the oc-aminoamide by condensation with phosgene or a phosgene equivalent. Treatment of the α-aminoamide with phosgene is preferably carried out in the presence of a tertiary-amine base such as triethylamine, pyridine, or N,N-diisopropylethylamine, in an inert solvent such as dichloromethane or 1-chlorobutane. The phosgene can be added as a gas or as a solution in an inert solvent such as toluene. Suitable temperatures range from about 0 °C to the reflux temperature of the solvent. 1 , r-Carbonyldiimidazole, diphosgene (ClC(=O)OCCl 3 ) and triphosgene (Cl 3 COC(=O)OCCl 3 ) can also be used in a similar manner. The tricyclic imide of Formula Id can be isolated by extraction into an organic solvent, aqueous wash, and removal of the solvent under reduced pressure. Additional purification can be accomplished by chromatography or recrystallization. The preparation of compounds of Formula I wherein J = J-6 and Z is CR 9 R 10 is also described in WO94/05668. Aryl Iodides For the preparation of compounds of Formula I wherein J = J-l 1, the appropriate aniline is first converted to the aryl alkyne as illustrated in Scheme 9. The aniline of Formula 1 is converted to the aryl iodide of Formula 21 via diazotization followed by treatment with a metal iodide salt. The aryl iodide is linked by a palladium coupling reaction to give the trimethylsilyl (TMS) alkyne. Hydrolysis of the TMS group with base affords the terminal alkyne of Formula 22. In the case of J-l 1, a [3+2] cycloaddition using a sydnone as the dipole and the alkyne as the dipolarophile affords the bicyclic pyrazole compounds. Introduction of the R 21 group affords the sulfonamides of Formula le. For example, treatment with N-chlorosuccinimide affords the R 21 = Cl compound. These methods are described in WO 93/15074, JP 4,059,706, WO 92/06962, and JP 3,163,063. Scheme 9 For compounds of Formula I wherein J = J-5, the coupling can also be accomplished starting with the aniline rather than the isocyanate. This method is described in WO 94/10173. For example, the synthesis of compounds of Formula If is illustrated in Scheme 10. Treatment of a diester of Formula 23 with an aniline of Formula 1 in the presence of a trialkylaluminum reagent (e.g., trimethylaluminum) in a non-coordinating solvent such as an aromatic hydrocarbon (e.g., benzene, toluene) or a halogenated hydrocarbon (e.g., methylene chloride, chloroform, and dichloroethane) affords a compound of Formula If. Scheme 10 Methods for the preparation of compounds of Formula I wherein J = J-l 3 are described in EP 379,911, U.S. 4,123,252, and U.S. 4,042,373. Methods for the preparation of compounds of Formula I wherein J = J-14 are described in U.S. 4,818,272. Methods for the preparation of compounds of Formula I wherein J = J-17 are described in WO 95/25725 and DE 4,437,295. Methods for the preparation of compounds of Formula I wherein J = J-18 are described in DE 3,340,296 and U.S. 93/06132. Compounds of Formula I wherein J = 15 and J = 16 can be prepared by methods known in the art or by obvious modifications of these methods. It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula I 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 I. One skilled in the art will also recognize that compounds of Formula I and the intermediates described herein can be subjected to various electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents. Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. 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. IH NMR data are in ppm downfield from tetramethylsilane. Couplings are designated by (s)-singlet, (d)-doublet, (t)-triplet, (q)-quartet, (m)-multiplet, (dd)-doublet of doublets, (ddd)-doublet of doublet of doublets, (dt)-doublet of triplets, and (br s)-broad singlet. EXAMPLE 1 Step A: Preparation of N-(4-chloro-2-fluoro-5-nitrophenyl)acetamide To a stirred solution of N-(4-chloro-2-fluorophenyl)acetamide (180.6 g, 0.96 mol) in concentrated sulfuric acid (IL) was added a mixture of 175 mL of concentrated HΝO3 and 175 mL of concentrated sulfuric acid at 0 to 5 °C in 1.5 h. After the addition was finished, the reaction mixture was stirred for another 0.5 h. The solution was poured into 5 L of ice water. After the product precipitated, it was isolated by filtration and then was dissolved in 2.5 L of ethyl acetate. After separation of the water layer, the organic layer was dried over sodium sulfate and then the solvent was evaporated. The crude product was triturated in diisopropyl ether (1.5 L), isolated by filtration, and dried under reduced pressure to afford the title compound of Step A (196.2 g, 87.6%) melting at 145-146 °C. l H NMR (Me 2 SO-d 6 ) δ 10.3-10.2 (s, IH), 8.9 (d, IH), 7.9-7.8 (d, IH), 2.2-2.1 (s, 3H). Step B: Preparation of N-(5-amino-4-chloro-2-fluorophenyl)acetamide To a solution of the title compound of Step A (15 g, 65 mmol) in 500 mL ethyl acetate was added 1.5 g Raney-Νickel that previously has been washed with methanol and ethyl acetate. The hydrogenation was performed at 5 bar of hydrogen pressure in an autoclave for 24 h at 50 °C. After filtration of the reaction through Celite®, the solvent was removed under reduced pressure. The crude product was triturated with petroleum ether and dried to isolate the title compound of Step B (12.6 g, 96%) melting at 142-143 °C. »H ΝMR (CDCl 3 ) δ 7.9 (d, IH), 7.3-7.2 (br s, IH), 7.1-7.0 (d, IH), 4.1-4.0 (s, 2H), 2.2-2. l (s, 3H). Step C: Preparation of N-f4-chloro-5-rr(chloromethyl)sulfonvnamino1-2- fluorophenyllacetamide To a stirred solution of the title compound of Step B (8.10 g, 40 mmol) in pyridine (50 mL) was added chloromethylsulfonyl chloride (3.84 mL, 40.45 mmol) over 30 minutes at 0 °C. After stirring at room temperature for 14 h, chloromethylsulfonyl chloride (0.38 mL, 4.05 mmol) was added to complete the reaction. Water was added so that the product precipitated. After filtration and washing with water and petroleum ether, the title compound of Step C was isolated as a bright powder (1 1.17 g, 89%) melting at 208-210 °C. 'H ΝMR (Me 2 SO- 6 ) δ 10.2-10.1 (s, IH), 9.9 (s, IH), 8.1 (d, IH), 7.6-7.5 (d, IH), 5.0-4.9 (s, 2H), 2.1 (s, 3H). Step D: Preparation of /V-(5-amino-2-chloro-4-fluorophenyl)-l- chloromethanesulfonamide The title compound of Step C ( 10.3g, 32.6 mmol) was suspended in 450 mL of 2M HCl. The temperature was raised to the boiling point of the reaction mixture under an argon atmosphere. After 45 minutes of stirring at this temperature, the reaction was cooled to room temperature, neutralized with NaHCO3, and the product was extracted into ethyl acetate. After drying of the solution over sodium sulfate, the solvent was evaporated under reduced pressure yielding 8.9 g (98%) of the title compound of Step D as bright crystals melting at 105-107 °C. i H NMR (Me 2 SO-ci 6 ) δ 9.9-9.8 (br s, IH), 7.2 (d, IH), 6.9 (d, IH), 5.5-5.4 (s, 2H), 4.9 (s, 2H). Step E: Preparation of l-chloro-N-(2-chloro-4-fluoro-5- isocvanatophenvDmethanesulfonamide To a stirred solution of phosgene (68 mmol) in 35 mL toluene was added the title compound of Step D (4.2 g, 15.4 mmol) in 80 mL toluene at 0 °C and the reaction was stirred at room temperature overnight. The temperature was then raised to 70 °C for 4 h. After cooling to room temperature, the reaction mixture was filtrated and the solvent was removed under reduced pressure. Drying of the white precipitate under reduced pressure yielded the title compound of Step E (4.4 g, 95%) melting at 101.5-102.5 °C. *H ΝMR (CDC1 3 ) δ 7.5 (d, IH), 7.3 (d, IH), 7.0-6.9 (br s, IH), 4.6-4.5 (s, 2H). Step F: Preparation of (2/?-c j)-l-rrr4-chloro-5-rf(chloromethyl)sulfonyllamino1- 2-fluorophenyl1aminolcarbonyll-4-hydroxy-2-pyrrolidinecarboxylic acid To a stirred slurry of the title compound of Step E (34 mmol) in 550 mL toluene was added 4- .s-D-hydroxyproline (4.55 g, 35 mmol) at room temperature. 500 mL of dimethoxyethane was added and the temperature was raised to 70 °C. After 1 h the temperature was raised to 90 °C for 6 h, and then the reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and after the addition of water, petroleum ether and ethyl acetate, the product was extracted into the water phase. The product was precipitated by removal of the water under reduced pressure, dissolved in ethyl acetate, and dried over Νa SO . The solvent was removed under reduced pressure furnishing the title compound of Step F (8.06 g, 50%). i H NMR (Me 2 SO--i 6 ) δ 12.4 (br s, IH), 10.1 (br s, IH), 8 2 (s, IH), 7.7 (d, IH), 7.5 (d, IH), 5.1-5.0 (br s, IH), 5.0-4.9 (s, 2H), 4.4 (m, IH), 4.3 (m, IH), 3.7-3.6 (m, IH), 3.4-3.3 (m, 2H), 2.4-2.3 (m, IH). Step G: Preparation of (6/?-trg?i )-l-chloro-A -r2-chloro-4-fluoro-5-(tetrahvdro-6- hvdroxy- 1.3-dioxo- 1 H-pyrrolof 1 ,2-c1imidazol-2(3HV vDphenyllmethanesulfonamide To a stirred solution of the title compound of Step F (2.7 g, 5.4 mmol) and N-hydroxysuccinimide (0.621 g, 5.4 mmol) in acetonitrile (50 mL) was added a solution of NN-dicyclohexylcarbodiimide (1.14 g, 5.4 mmol) in acetonitrile (30 mL) over 30 minutes at 0 to -5 °C. The reaction was stirred at room temperature for 14 h. The by¬ products were removed by filtration and the solvent was evaporated under reduced pressure to yield the title compound of Step G (2.6 g, quantitative yield) as a crude product melting at 198-200 °C. l H ΝMR (Me 2 SO-<i 6 ) δ 10.2 (br s, IH), 7.8-7.7 (d, IH), 7.5-7.4 (d, IH), 5.2-5.1 (br s, IH), 5.1-5.0 (s, 2H), 4.5 (m, IH), 4.3-4.2 (m, IH), 3.7 (m, IH), 3.1 (m, IH), 2.3 ( , IH), 2.0 (m, IH). Step H: Preparation of ( 6S-c/j ) -l-chloro-N-r2-chloro-4-fIuoro-5-(6- fluorotetrahvdro- 1.3-dioxo- lH-pyrrolof 1.2-climidazol-2f 3H)- yl )phenyll me thanesulf onamide To a stirred solution of the title compound of Step G (2.7 g, 5.4 mmol) in dichloromethane (60 mL) was added pyridine (1.0 mL) at -55 °C and DAST (diethylaminosulfur trifluoride) (0.8 mL, 5.8 mmol) over 30 minutes at the same temperature. The reaction mixture was warmed to room temperature and the clear solution was stirred for 14 h. After concentration under reduced pressure, the resulting brown oil was dissolved in ethyl acetate and this solution was treated with water and dilute ΗC1. The organic layer was separated, dried with sodium sulfate, and the solvent * was evaporated under reduced pressure to yield a crude product containing the title product of Step Η (1.81 g, 61%). lΗ ΝMR (CDC1 3 ) δ 7.62 (d, 1Η), 7.34 (d, 1Η), 7.26 (br s, 1Η), 5.5 (m, 1Η), 4.60 (dd, 1Η), 4.52 (s, 2Η), 4.12 (m, IH), 3.62 (dd, IH), 2.64 (m, IH), 2.06 (m, IH). EXAMPLE 2 Step A: Preparation of (6S-cis)- 1 -chloro-N-r2-chloro-5-(6-chlorotetrahvdro- 1 ,3- dioxo-lH-pyrroloπ.2-climidazol-2f3H)-yl)-4- fluorophenyllmethanesulfonamide To a stirred suspension of the title compound of Example 1, Step G (3.3 g, 8 mmol) in 25 mL toluene and 0.02 g DMF was added at 80 °C thionyl chloride (1.31 g, 11 mmol) over a period of 15 minutes. The suspension was stirred at the same temperature for 2 h and at 105 °C for 30 minutes. After cooling to room temperature, the organic layer was washed with water, dried, and the solvent was evaporated under reduced pressure to yield the title compound of Step A, a compound of this invention, in quantitative yield as a crude powdery product melting at 169-170 °C. lΗ ΝMR (CDC1 3 ) δ 7.64 (d, 1Η), 7.36 (d, 1Η), 7.20 (br s, 1Η), 4.78 (m, 2Η), 4.56 (s, 2H), 4.24 (dd, IH), 3.62 (dd, IH), 2.62 (m, IH), 2.38 (m, IH). EXAMPLE 3 Step A: Preparation of (6S- 5)-N-f 2-chloro-4-fluoro-5-(6-fluorotetrahvdro- 1.3- dioxo- lH-pyrrolor 1 ,2-climidazol-2(3H)-yl)phenyll-N- rfchloromethvPsulfonyllacetamide To a solution of the title compound of Example 1, Step Η (4.14 g, 10 mmol) in anhydrous dichloromethane (200 mL) and pyridine (5 mL) was added a solution of acetyl chloride (0.863 g, 11 mmol) in dichloromethane (10 mL) dropwise at room temperature. After completion of the reaction (monitored by tic), the organic phase was washed with water (50 mL) and diluted with ΗC1 (5%, 50 mL). The organic layer was separated, dried (MgSO ), and the solvent was removed in vacuo to give the title compound of Step A, a compound of this invention, as a white solid (4.3 g, 94%) melting at 198-200 °C. »Η ΝMR (CDC1 3 ) δ 7.56 (m, 2H), 5.52 (m, IH), 5.40 (dd, IH), 4.84 (d, IH), 4.62 (dd, IH), 4.08 (m, IH), 3.62 (m, IH), 2.68 (m, IH), 2.05 (s, 3H), 1.98 (m, IH). EXAMPLE 4 Step A: Preparation of (6S-c.j)-N-r2-chloro-5-(6-fluorotetrahvdro-l ,3-dioxo-lH- pyrrolof 1 ,2-c " limidazol-2(3HV yl -fluorophenyll-N- KchloromethvDsulfonyll acetamide To a solution of the title compound of Example 2, Step A (4.29 g, 10 mmol) in anhydrous dichloromethane (200 mL) and pyridine (5 mL) was added a solution of acetyl chloride (0.862 g, 11 mmol) in dichloromethane (10 mL) dropwise at room temperature. After completion of the reaction (monitored by tic), the organic phase was washed with water (50 mL) and diluted with ΗC1 (5%, 50 mL) and water (50 mL). The organic layer was separated, dried (MgSO4), and the removed the solvent to give the title compound of Step A, a compound of this invention, as a white solid (4.4 g, 93%) melting at 180-181 °C. lΗ ΝMR (CDC1 3 ) δ 7.50 (m, 2Η), 5.38 (dd, IH), 4.92 (d, IH), 4.78 (m, 2H), 4.24 (dd, IH), 3.62 (dd, IH), 2.62 (m, IH), 2.26 (m, IH), 2.04 (s, 3H). EXAMPLE 5 Step A: Preparation of (6S-cis)-l-chloro-N-r2-chloro-4-fluoro-5-(6- fluorotetrahvdro- 1 ,3-dioxo- lH-pyrrolor 1.2-climidazol-2(3jff)-vnphenyll- N-methylmethanesulfonamide A mixture of the title compound of Example 1, Step Η (0.414 g, 1 mmol), dimethyl sulfate (0.14 g, 1.1 mmol), and potassium carbonate (0.27 g) in acetone (10 mL) was stirred at room temperature for 4 h. After completion of the reaction, the potassium carbonate was filtered off and the solvent was removed on a rotary evaporator. The title compound of Step A, a compound of this invention, was isolated by flash chromatography (0.41 g, 95%) as a white solid melting at 90-92 °C. l H ΝMR (CDC1 3 ) δ 7.52 (d, IH), 7.39 (d, IH), 5.54 (m, IH), 4.62 (s, 2H), 4.60 (m, IH), 4.08 (m, IH), 3.60 (dd, IH), 3.42 (s, 3H), 2.64 (m, IH), 2.01 (m, IH). EXAMPLE 6 Step A: Preparation of (65-c/.?H-chloro-N-f2-chloro-4-fluoro-5-(6- fluorotetrahvdro-1.3-dioxo-lH-pyrrolori.2-c1imidazoI-2(3H -yl)phenyn- N-ethylmethanesulfonamide A mixture of the title compound of Example 1, Step Η (0.414 g, 1 mmol), diethyl sulfate (0.17 g, 1.1 mmol), and potassium carbonate (0.27 g) in acetone (10 mL) was stirred at room temperature for 4 h. After completion of the reaction, the potassium carbonate was filtered off and the solvent was removed on a rotary evaporator. The title compound of Step A, a compound of this invention, was isolated by flash chromatography (0.41 g, 92%) as a white solid melting at 198-200 °C. l ΝMR (CDCI3) δ 7.46 (d, 1Η), 7.42 (d, 1Η), 5.52 (m, 1Η), 4.62 (dd, 1Η), 4.59 (s, 2Η), 4.02 (dd, IH), 3.80 (m, 4H), 3.60 (dd, IH), 2.64 (m, IH), 2.01 (m, IH), 1.20 (t, 6H). EXAMPLE 7 Step A: Preparation of (65-ciy)-methyl r2-chloro-4-fluoro-5-(6-fluorotetrahydro- 1 ,3-dioxo- lH-pyrroloπ .2- limidazol-2(3H)- yl)phenvnr(chloromethyl)sulfonyncarbamate To a mixture of the title compound of Example 1, Step Η (0.32 g, 0.7 mmol) and pyridine (0.5 mL) in dichloromethane (5 mL) was added a solution of methyl chloroformate (0.09 g, 0.95 mmol) in dichloromethane (1 mL) at room temperature. After completion of the reaction (2 h), the solvents were removed in vacuo and the title compound of Step A, a compound of this invention, was isolated by flash chromatography (0.31 g, 95%) as a white solid melting at 108-115 °C. l E ΝMR (CDCI3) δ 7.40 ( . 2Η), 5.42 (m, IH), 5.36 (dd, IH), 4.92 (dd, IH), 4.60 (m, IH), 4.04 (m, IH), 3.82 (s, 3H). 3.60 (dd, IH), 2.64 (m, IH), 2.02 (m, IH). EXAMPLE 8 Step A: Preparation of (6S-cis)- 1 -chloro-N-r2-chloro-5-(6-chlorotetrahydro- 1 ,3- dioxo- 1 H-pyrrolor 1.2-climidazol-2(3H)-yl)-4-fluorophenvn-N- methylmethanesulfonamide A mixture of the title compound of Example 2, Step A (0.43 g, 1 mmol), dimethyl sulfate (0.17 g, 1.1 mmol), and potassium carbonate (0.27 g) in acetone (10 mL) was stirred at room temperature for 4 h. After completion of the reaction, potassium carbonate was filtered off and the solvent was removed on a rotary evaporator to yield the title compound of Step A, a compound of this invention, as a white solid purified by flash chromatography (0.40 g, 90%) and melting at 1 19-124 °C. >Η ΝMR (CDC1 3 ) δ 7.52 (d, IH), 7.42 (d, IH), 4.76 (m, 2H), 4.62 (s, 2H), 4.24 (dd, IH), 3.64 (dd, IH), 3.42 (s, 3H), 2.62 (m, IH), 2.22 (m, IH). EXAMPLE 9 Step A: Preparation of (6S-cis)- 1 -chloro-N-r2-chloro-5-(6-chlorotetrahvdro- 1.3- dioxo-lH-pyrrolof l.2-climidazol-2(3H)-yl)-4-fluorophenyll-N- ethylmethanesulfonamide A mixture of the title compound of Example 2, Step A (0.43 g, 1 mmol), diethyl sulfate (0.17 g, 1.1 mmol), and potassium carbonate (0.27 g) in acetone (10 mL) was stirred at room temperature for 4 h. After completion of the reaction, potassium carbonate was filtered off and the solvent was removed on a rotary evaporator to yield the title compound of Step A, a compound of this invention, as a white solid purified by flash chromatography (0.4 g, 89%) and melting at 152-154 °C. Η ΝMR (CDC1 3 ) δ 7.40 (m, 2Η), 5.30 (s, 2H), 4.72 (m, 2H), 4.22 (dd, IH), 3.82 (m, 4H), 3.60 (dd, IH), 2.60 (m, IH), 2.24 (m, IH), 1.40 (t, 3H), 1.20 (t, 3H). EXAMPLE 10 Step A: Preparation of (6S-ci-f)-methvI r2-chloro-5-(6-chlorotetrahydro-1.3- dioxo- 1 H-Pyrrolor 1.2-climidazol-2(3HV yl)-4- fluorophenvnf(chloromethyl)sulfonyllcarbamate To a mixture of the title compound of Example 2, Step A (0.34 g, 0.79 mmol) and pyridine (0.5 mL) in dichloromethane (5 mL) was added a solution of methyl chloroformate ( 85 mg, 0.9 mmol) in dichloromethane (1 mL) at room temperature. After completion of the reaction (2 h), the solvents were removed and the title compound of Step A, a compound of this invention, was isolated by flash chromatography (0.34 g, 93%) as a white solid melting at 117-124 °C. l U ΝMR (CDC1 3 ) δ 7.40 (m, 2Η), 5.40 (dd, IH), 4.96 (dd, IH), 4.76 (m, 2H), 4.24 (dd, IH), 3.84 (s, 3H), 3.62 (dd, IH), 2.60 (m, IH), 2.24 (m, IH). EXAMPLE 11 Step A: Preparation of l-chloro-N-r2-chloro-4-fluoro-5-(hexahvdro-7-hvdroxy- 1.3-dioxoimidazor 1.5-αlpyridin-2(3H)-yl)phenyllmethanesulfonamide To a solution of the title compound of Example 1, Step E (4.54 g, 15.2 mmol) in dichloromethane (20 mL) was added dropwise a solution of methyl cis-4-hydroxy-2- piperidinecarboxylate (2.41 g, 15.2 mmol, prepared as described in J. Org. Chem. (1991), 4084) in dichloromethane (20 mL) at room temperature. The reaction was stirred at room temperature for 20 hours, quenched by the addition of water, and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with water and dried over magnesium sulfate. The solvent was removed under reduced pressure and the title compound of Step A, a compound of this invention, was isolated as a foam by flash chromatography (4.98 g). ! Η ΝMR (Me 2 SO-rf6) δ 10.1 (br s, IH), 7.75 (m, IH), 7.4 (dd, IH), 5.1 (m, IH), 4.9 (s, 2H), 4.1-3.9 (m, 3H), 3.75 (m, IH), 2.95 ( , IH), 2.05 (m, IH), 1.9 (br d, IH), 1.2 (m, IH). EXAMPLE 12 Step A: Preparation of cis- 1 -chloro-N-f 2-chloro-4-fluoro-5-(7-fluorohexahydro- 1.3-dioxoimidazor 1.5-Ωlpyridin-2(3H)-yl)phenyllmethanesulfonamide To a solution of the title compound of Example 1 1, Step A (771 mg, 1.80 mmol) in dichloromethane (10 mL) was added dropwise diethylaminosulfur trifluoride (0.48 mL, 3.60 mmol) at 0 °C. The reaction was stirred at 0 °C for 1 hour, quenched with cold water, and extracted with dichloromethane. The combined organic layers were washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The title compound of Step A, a compound of this invention, was isolated by flash chromatography (332 mg) as a foam melting at 60-64 °C. ! Η ΝMR (CDC1 3 ) δ 7.7 (d, IH), 7.4 (d, IH), 7.1 (br s, IH), 5.28 and 5.12 (two br s, IH), 4.6 (s, 2H), 4.4 (dd, IH), 4.2 (dd, IH), 3.3 (ddd, IH), 2.65 (m, IH), 2.2 (m, IH), 1.9-1.6 (m, 2H). EXAMPLE 13 Step A: Preparation of ethyl rrdimethylamino)rrf(4-chloro-2-fluoro-5- nitrophenvDaminolcarbonylliminolmethvnmethylcarbamate To a solution of l-chloro-5-fluoro-4-isocyanato-2-nitrobenzene (3.4 g, 15.7 mmol) in toluene (50 mL) was added dropwise a solution of ethyl [(dimethylamino)iminomethyl]methylcarbamate (2.41 g, 15.2 mmol, prepared as described in U.S. 3,902,887) in toluene (50 mL) at room temperature. The reaction was stirred at room temperature for 2 hours, quenched by the addition of water, and the aqueous layer was extracted with dichloromethane. The excess solvent was removed under reduced pressure and the title compound of Step A was isolated by flash chromatography as a yellow solid (5.07 g) melting at 158-159 °C. iH ΝMR (CDC1 3 ) δ 9.05 (d, IH), 7.3 (br s, IH), 7.2 (d, IH), 4.2 (q, 2H), 3.15 (s, 3H), 3.0 (s, 6H), 1.2 (br s, 3H). Step B: Preparation of 3-(4-chloro-2-fluoro-5-nitrophenyl)-6-(dimethylamino)-5- methyl-1.3.5-triazine-2.4(lH.3H)-dione A mixture of the title compound of Step A (3.0 g, 7.7 mmol) in methanol (150 mL) was stirred at room temperature overnight. The excess solvent was removed under reduced pressure to provide the title compound of Step B as a white solid (2.8 g). lΗ ΝMR (CDC1 3 ) δ 8.05 (d, 1Η), 7.4 (d, 1Η), 3.45 (s, 3Η), 3.1 (s, 6H). Step C: Preparation of 3-(5-amino-4-chloro-2-fluorophenyl)-6-(dimethylamino)- 5-methyl- 1.3.5-triazine-2.4( lH.3H)-dione To a slurry of iron powder (5.3 g) in 5% aqueous acetic acid (30 mL) was added dropwise a solution of the title compound of step B (2.8 g, 8.1 mmol) in a mixture of concentrated acetic acid (25 mL) and ethyl acetate (25 mL) at room temperature. The reaction was stirred at room temperature for 30 minutes, diluted with excess ethyl acetate, filtered through Celite®, and washed with water. The aqueous phase was extracted with ethyl acetate and the combined organic layers were washed with saturated aqueous sodium bicarbonate solution and water. The organic layers were then dried over magnesium sulfate and concentrated under reduced pressure. The title compound of Step C was isolated by flash chromatography as a foam (1.59 g). H NMR (CDC1 3 ) δ 7.15 (d, IH), 6.65 (d, IH), 3.95 (br s, 2H), 3.4 (s, 3H), 3.1 (s, 6H). Step D: Preparation of l-chloro-N-f2-chloro-5-r4-(dimethylamino)-3.6-dihvdro- 3-methyl-2.6-dioxo- 1.3.5-triazin- 1 (2H)-yl1-4- fluorophenyllmethanesulfonamide To a solution of the title compound of Step C (359 mg, 1.15 mmol), pyridine (0.50 mL), and a catalytic amount of 4-dimethylamino pyridine in dichloromethane was added chloromethylsulfonyl chloride (0.136 mL, 1.37 mmol) at 0 °C. The reaction was stirred at 0 °C for 90 minutes and then concentrated under reduced pressure. The crude oil was dissolved in dichloromethane and washed sequentially with water, IN aqueous ΗC1, and water. The organic phase was then dried over magnesium sulfate and concentrated under reduced pressure. The title compound of Step D, a compound of this invention, was isolated by flash chromatography as a foam (126 mg) melting at 234-237 °C. Η ΝMR (CDC1 3 ) δ 7.7 (d, 1Η), 7.35 (d, 1Η), 7.0 (br s, 1Η), 4.55 (q, 2Η), 3.45 (s, 3H), 3.15 (s, 6H). By the procedures described herein together with methods known in the art, the following compounds of Table 1 can be prepared. The following abbreviations are used in the Table which follows: CΝ = cyano and Ph = phenyl. TABLE 1 J= 1. Y = Cl. and R2 = CH C1 J = 3. O = O.Y = Cl. and R 2 = CH C1 X F F F F F F F F Cl H CH 3 N(CH 3 ) 2 Cl C(=0)CH 3 CH 3 N(CH 3 ) 2 Cl C0 2 CH 3 CH 3 N(CH 3 ) 2 Cl H CHF 2 N(CH 3 ) 2 Cl C(=0)CH 3 CHF 2 N(CH 3 ) 2 Cl C0 2 CH 3 CHF 2 N(CH 3 ) 2 J = 5 and O = O X Y zl F H CH 2 F H CH 2 F H CH 2 F H CH 2 F H CHF F H CHF F H CHF F H CHF F H CHCl F H CHCl F H CHCl F H CHCl F Cl CH 2 F Cl CH 2 F Cl CH 2 F Cl CH 2 F Cl CH 2 F Cl CH 2 F Cl CH 2 F Cl CH 2 F Cl CH 2 F Cl CH 2 F Cl CH 2 F Cl CH 2 F Cl CH 2 F Cl CH 2 F Cl CH 2 F Cl CH 2 33 35 39 41 43 47 U CQ U CQ U PQ U PQ U CQ U PQ U CQ U PQ U CQ U CQ U CQ U OQ U OQ CN CS CN CN CN CS CN CS CN CN CS CN CN CN CN CN CN CS CS CN CN CN CN CN CN CS Xu Xυ Xu Xu Xu Xυ Xu Xu Xu Xu Xu Xu Xu Xu Xu Xu Xυ Xu Xu Xu Xu Xυ Xu 3u3 Xu 3u: — — CN CN CN CN CN CN CS x x x x x x x x , x x u υ υ υ u υ υ υ υ u υ u u υ u υ u u u u υ υ υ u υ u g u υ u δ δ u u δ u υ δ δ δ δ υ zu zυ zu zu zυ zu zu zu zu zu zu zυ zυ zu zυ zu zυ zυ zu zu zu zu zυ zυ zu zυ o I- •Λ IΛ u u u υ υ u u u u υ u u u u u u υ u u u u u u υ u u O 51 J = 7. Y = Cl. and R 2 - CHC1 S MM MM HM HM HM 8 ϊ ϊ ϊ ϊ ϊ ιc co co co co co co co co co co co co co co co co co co co co X SG CN CS U U fcC 33 33 33 a a u u u u u u u u u b υ HM uX uX u uHG uX uX uX uX u uX uDG u u υ u u ve PU U, li, U- U ii, , u. α. a, i , M H t. MM θ u u u ϋ u υ u u u u u u u u u u IΛ IΛ Os o 55 J=llandR 1 =Cl 57 59 U PQ U OQ U oa U CQ U OQ U CN cN CN CS CN cS CN cN CN CS CS xu xu xu xu xυ xu xu xu xυ xu xυ — CS CN CN CN CN CN CN CS CN CN CN CN CN CN CS cN -^ --ι CN CN — — CS CN -M — rS C O vO a a a a x a a a w w w w w w w w w w w w w w w w a a a x a a a a w ac jij j u u υ u u υ u u u O u u u u υ u u u u u υ u u u u y y y y y y y y u u υ u Z Zυ Zu Zu uZ uZ uZ Zυ uZ Zu uZ Zu Zu uZ Zυ Zu Zu Zu υZ Zu υZ Zu Zu Zυ uZ M 3 -* X DC X X X X X X X X ve r- IΛ IΛ ^ u υ u υ u u u u u u υ o 61 — CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN C CN O U U U U U U U U U CN N C CN ^ ^ CN C CS CS CS C CS N CN CN M fc fc lt fc lt l-H H M M p U -uC _uπ u DC u SC _uC u -C -uC Xu -GC y 33 y 33 y MG M y M y M M y M y MM y X X y y MM M y M H y G y HG y DG y 33 3 y 3 M y M y X X y y X X y X y X y y X y X H y M D y G 3 U υ U U U U U U U PQ CQ OQ PQ CQ PQ PQ PQ CQ CQ CQ CQ CQ CQ βa CQ ffl αa cQ CQ CQ oa PQ PQ PQ PQ OQ P u u υ υ u u u u u υ u u u u u u u υ υ u u u u u u u u u u u u u u u u u O 63 CN CN CS CN CN CN CS CS CN CN CS CN CS CN CN CN E| — — CN C Cl 3 & f fc & fc c feX fcX fe & CN CS CN ^ cH M fcH fe &^ HI< f .y^ yW yW y-^ yW y^ Wy y y y y y y y y y NI X u u υ u u u u u υ u u u u u u u u u u u υ u υ u u υ u u υ u uX uX H X X X XI MM UM O & t- fc u u u u N C^ UM ^ | £ UM M UM lM lt li. l . 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M M M UM UM UM It, li, li, UM UM t 0 CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN VO VO g y u g u % u % u % u % u % u % u % u % u £ %u u x 1 u % u % £u gu § y g y g y § y § y g y § y § y g y g y § y g y g y g y g y g y g y g y g y U U U U U U U U U U U U U U U U U n n rt ø PQ oa CQ OQ rt CQ CQ PQ PQ OQ PQ cQ OQ oa oQ O 67 CN CN CN CN CN CN CN CN CN CN CN CN CS CN CN CN CN CN u u u υ u u u u u u u u u u u u u u u u u y u u u u u u u u u u u u u υ Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z u u u u u u u u u υ u υ u υ u u υ u υ u υ u υ u u υ u u u u u u u u u υ vo IΛ IΛ li, U M U M l U- H H U^ U M U M lt H U M - U- MM M U M t MM U M - M p HM U- tt, Os O CS CS CN CN CN CS CN ON VO CN CN CS li, MM li, Uj y y y y C CN C C CN O> C C CN N CN CS C CS fc Jt U, H UM tt lt UM UH JyG Mu 3u3 Xυ Xu Xu Xu wy Xy _yc 5yC MuM MuM DuG MuM Mυ Mu Xu 3u3 3υ3 Xu 3u3 3υ3 HuM HuM 3υ3 Xu Xυ Xu MuM Xυ Xu Xυ Xu Xυ Xu X X X X X X X X X X X y y y y y y y y y y y y y y y y y y y y y y y y y vo IΛ IΛ u u u u u u u u u u u u u u u u u u u u u u u u u u u u u u u u u u u u ON CN CN CN CN CN CN CN CN CN CN CN CN CN M^ M< ^ X X X X X ?T -T- ?T W fT! X ^ ^ !τ ! -T ! ^ U U U U U U U U U U U U U U U y y y y y y y y y y y y y U U U y y y y m rt PQ CQ CQ CQ rt CQ rt PQ PQ PQ PQ CQ rt OQ CQ CQ CQ ffi rt ffi tt CQ ffl rt CQ CQ rt CQ y y y y y ve IΛ «Λ u υ υ υ υ υ υ υ u υ υ υ υ υ υ υ u u υ υ υ u υ υ υ υ u υ υ υ υ υ u υ u υ ON o rt CS U CN m CN U CN c CQN U CN rt CN UCN mCN ^U mCN UCN rtCN UCN rtcN UCN rtCN UCN oCQS UCN pCQN UCN pCQN UCN rtCN UCN rtcN UCN rtcS UCS mCN UCN rtCN UCS rtCS UCS X υ uX Xu uX uDC Xu uX uX uX Xu Xu Xu Xu Xu Xu Xu Xυ uX Xu uX Xu Xu uX uX Xu υX uX Xυ Xυ Xu uX uX υX uX Xu Xu vo CΛ a co co H u a a a a a a X U u III u a a a a u u u C- cs a a a a o a a O O a a II o II δ δ 8 a a o a o ». B δ 88 a y II II o u u u u u o O O r cs U U a a u u Jt Jl O O u u U U a u a u u υ υ CN r— X u uE uX u uX uX Xu Xu υ υ uz υz υz uz υz υz uz zυ uz υz uz uz zu υz uz zu uz υz zu zυ zu uz zu zυ zυ zu uz zu zυ zu υz υz zu zu zu uz vo I- IΛ IΛ u υ u u υ υ u u u u u u u u u u u u υ u u υ u u u u υ u u u u u u u u u ϊ O^N rt U CQ x x x co co co co co co co co co co co co co co co co co co co co co co co 33 33 X 33 33 33 u υ υ cs X X X D 3 3 3 X X 3 X X X X υ u u u u u D-l uM u u u 3u3 uC 3u3 u3 u3 u3 u u u3 Xu u u u X X X X X X u u u u u υ υ u u u u u u X X H U υ u III u o δ u X X u u El rs cs cs cs cs o d ( N ft [I tt, N M (S U, b [j, CN CN CN Uj Uj Uj CN CN CN UM U MM OJ OI OI - UH U- NI UυG Xu Xυ Xu Xu Xu Hu Mυ 3υ3 Xu DuC Xu 3u3 3u3 3u3 3u3 Xu 3u3 3υ3 MuM MυM MυM MuM Xu MuM HuM MυM Mυ 3u3 3u3 75 J = 15. Y = Cl. R 2 = CH C1 l9 = H J = 17. O = O. and R 19 = CH 3 X Y w F H N F H N F H N F H N U CQ U oQ U PQ U ffl U m U m U pQ U CQ U CQ U CQ U CQ U rt U CQ U CQ U CQ U rt U ffl U CQ CN CS OI OI OI CN CN CN CN OI CS CN CN CS CS CN CN CN CN CS CS CS CN CN CS OI CS CS CN CN C^ x x x x x x x a a a a a a a a a a a a a a x x x x x x x x x x x x x x x u υ υ υ υ υ υ υ u υ υ υ υ υ υ υ υ υ υ υ υ u υ u υ υ υ υ υ υ υ υ υ υ υ u m r r t m e co co co ro υ u u z z z z z z z z z z z z z z z X u υ υ u υ υ z z z z z z z z z u υ u u X u X u X u u υ u u X X X X X X X X y y y y y y y y y y y y y y y y y y y y U U y y y y y u t » IΛ U M U. U- U. UM U- UM MM U- UM U- U-. UM U- UM UM MM UM UM PM - MM U- U- M- U^ IΛ ON o 79 U CN rtol UOI fflOi UrS mrS UCS rtCN UOI rtCS UCS cCQS UCS rtCN UCN rtCN UCN cCQS UCS mCN UCS rtCN urS mCN uCN pCQN UOI oOQI UOI mCN uCN rtOI UCN cQCN UCS mCS X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X u υ υ υ υ υ υ u υ υ υ υ υ υ υ υ υ υ υ υ υ u u u u u υ u υ υ u υ υ υ u u co CO co co CO co z z z z z z Uu Uu Uu Uu Uu Uu Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z X X X X X X X X X X X X y y y U U U U U U U U U U U U U U U U U U U U U vO r~ IΛ IΛ υ u υ υ υ u υ u u υ u υ υ u υ u υ υ υ u u u u u u u υ u υ u υ υ u υ u u ON 83 19 O = O. and R 24 = CO 2 CH X Y Z F H CH 2 F H CH 2 89 u cN mcN UCN rtoi Uoi rtcs UcN rtrs Urs pcQN Urs mcN UCN PcQN Ucs mrs urs orQs Urs mrs urs mrs urs moi Uoi rtoi Uoi ooQi Uoi moi UcN pQoi Uoi pQoi Urs eQoi x x x x x x x x x Dc x x x x x x a a a a a a a a a a a a a a a a a a a x u u u u u u u u u u u u u u u u u u u u u u u u u u u u u u u u u u υ ve X X X X co co X X H X X U cN y. X X o x x u rs y π r-ι V o. 8 X8 X X X o o δ δ cN y o o 8.8 o y υ o o o u U u u u u u u u u υ u s cN oi oi rs rs rs rs rs rs rs rs cN CN CS CN OI OI ΓS O O ON M X 3U X X X X X X X X X u u u υ u υ u u _ _ _ u M u u υ υ υ υ u u X X X u u u u u u u u u u u υ u u u u u u u u υ u u u u zυ zυ uz zu zu zu zυ zυ υz υz zu zu zu zυ zu zu zu zu zu zu zυ zu υz zu υz zu zu zu zu zu zu zu z z z z u u u u vo t- IΛ It MM lt UM H lt HM lt l HM HH MM HM HM IΛ O 91 cN cs cs rs rs rs rs rs rs oi r u u u u u u u u u u 4? j? j? jy j? 4? jy j? j? j? j? j? j? j? 4? y y y y y u y U U y U U U U U U U U U U U U U U U U U U U U U U U U U U a a a a a a a x x x υ u u υ u u υ u u u u u u u u u υ u u u u u u υ u u vo I-- IΛ u u u u u u υ υ u u u u u u u u u u u u u u u u u u u u u u u u u u u u IΛ o rs rs rs cN CN rs rs rs cs oi cs oi oi oi rs cs CO £ fe £ £ y y y y y y y y y y y y y y : y ^ u u u u y y y y y y y y y y y y O u u y y y y y y y y y y y y y y y y u u u υ u u u u u υ u u υ u υ u υ υ υ u pQ m m m « m oQ m rt rt PQ m m ffl CQ cQ ve r- IΛ IΛ υ u u u υ u u u u υ υ υ υ υ υ υ υ u u u u υ υ υ u υ u υ u u υ υ u υ u u r- ON O U ffl ars o υ au CN CN cN oi rs rs cs rs rs rs rs cs cs rs rs cs σv X X X X X X X X X X X X ^ W H ff W HMJ ^ IT lM^ ^ H fT fT fTJ HM ^ U U U U U U U U U U U U U U y y y y y y y y y y y y y y y y U U U U U U rt m α cQ CQ OQ rt CQ CQ CQ PQ PQ n oQ rt oa OQ CQ rt PQ CQ PQ pQ CQ OQ PQ OQ n cQ PQ zυ υz uz uz uz uz vo r- IΛ IΛ u u u u u u υ υ u u u u υ υ υ υ υ u u u υ υ u υ u u u u u υ u u u u u υ r- O rs oi rs rs rs rs rs rs rs rs cs cN cN cs oi uM uX uX uX uX uX Xu Xu uX uX xu ux ux xu uX u xu ux ux ux ux uX Xu uX 2yc Xy Xy Xy yX D Xu zu zu zυ zu zu zu zυ zu zu zu zu zυ zυ zu zυ zu zυ zu zυ zu zu zy zy zu zυ zu zu zυ zu zu zu zu zυ zu zu zυ vo IΛ IΛ u u u u u u u υ u u u υ υ u υ u u υ u u u u υ u υ υ u υ u u u u u u u υ Cl CN CHCl CH 2 C≡CH CH 2 C1 Cl CN CHCl CH 2 C≡CH CH 2 Br J = 19. O = O. and R 24 = αθ)N(OCH 3 )(CH 3 ) X Y Z F H CH 2 F H CH 2 F H CH 2 F H CH 2 F H CH 2 F H CH 2 F H CH 2 F H CH 2 F H CH 2 F H CH 2 F H CH 2 F H CH 2 F H CH 2 F H CH 2 F H CH 2 F H CH 2 F H CHF F H CHF F H CHF F H CHF F H CHF F H CHF F H CHF F H CHF F H CHF F H CHF F H CHF F H CHF F H CHF F H CHF F H CHF F H CHF 97 99 os rs cs rs rs rs cN cs cs rs rs cs o» cs cs cs O o Mu 3uM υX υ33 3u3 3u3 uX uX Xu uX υX u33 3υ3 3u3 Xu 3υ3 Xu uX 3u3 Xu Xu 3υ3 3υ3 3u3 3u3 υ33 u33 3u3 uMM HuG y£ y£ υ£ Xu υ£ 3u Zu Zu Zυ Zu Zu Zu Zu Zu uZ Zu Zu Zu Zu Zu Zu Zu Zu Zυ Zu Zυ Zυ Zu Zu Zu Zu Zu Zυ Zu Zu Zu Zu Zu Zu Zu Zu Zυ IΛ t U. UM UM lt l UM UM lt lt t HM tt l l U, b HH t l HM MM lt t HM M H^ IΛ o> o CN CS Ol I cs os rs CS CS CS CN CS CS CN CN CN CN CN Ol u u u u u i f u uT u u'Tl υfuf uff υW υ u > T u zu zu zu zυ zu uz zu zu x x x x x x x x x x x x x x x x x x a a a a a a a a a a ve IΛ u- u- UM UM UM UM U- lt y y y y y y y y y y y y y y y y y u u y y y y y y y y y IΛ ON 103 Cl Cl CHF Cl Cl CHF Cl Cl CHF Cl Cl CHF Cl Cl CHF Cl Cl CHF Cl Cl CHF Cl Cl CHF Cl Cl CHF Cl Cl CHF Cl Cl CHF Cl Cl CHF Cl Cl CHCl Cl Cl CHCl Cl Cl CHCl Cl Cl CHCl Cl Cl CHCl Cl Cl CHCl Cl Cl CHCl Cl Cl CHCl Cl Cl CHCl Cl Cl CHCl Cl Cl CHCl Cl Cl CHCl Cl Cl CHCl Cl Cl CHCl Cl Cl CHCl Cl Cl CHCl Cl Br CH 2 Cl Br CH 2 Cl Br CH 2 Cl Br CH 2 Cl Br CH 2 Cl Br CH 2 Cl Br CH 2 Cl Br CH 2 Cl Br CH 2 Cl Br CH 2 oi oi i oi rs rs rs rs rs rs rs rs rs oi cs cs oi oi oi TI¬ CS C MM M X X X X X X X X x x x X x x fc & u u u u u u u u u u u u u u u u u u u υ u υ υ u υ u u u u υ υ υ rUi rUi y x xy xy y x xy y X Xy y X Xu Xu Xu xu xy y x y rt rt rt rt n m m m m m n rt m m ή rt rt rt ή rt rt rt rt oQ rt rt oQ rt rt n oQ cQ rt PQ rt cQ PQ IΛ IΛ u υ u υ υ u u u u u υ u u υ u u u u υ u u u u u u u υ u u υ u u u u u u u o cN oi rs rs cs cs cN cs cs cs oi os tS (N C ( CN <N rN| t u HU Xu Xu Xu Hu Xu Xu Xu Xu Xu u X Xu Xu MMuMM X MuM uX MM X Xu uX X Xu Xυ Xυ Xυ Xυ Xu Xu Xu Xυ Xυ X DC X X XX XX j!ττ*! ^m ^^ ^ p U U U U y y u•^ u uz uz zu zu zu uz zu zu zu zu zυ υz zu zυ zυ zu zu zυ zu zu zυ zu zu zu zu zu uz zu zu zu uz zu zu zu zu zu VO IΛ IΛ u υ υ u u υ u u u u u υ u υ υ υ u υ u u u u u u υ u u u u u u u υ u u u ON o — — oi rs rs cN oi ol oi rs El oi rs rs rs cs oi os i i r cs cN rs cN i rs r s cN s rs oi UM lt lt U HM l M DC X X DG X X X DC HG X HM HG 33 33 33 33 33 X 33 33 X 33 U U U U U U U U U U U U U U U U U U U U U U X X X X X X X X X X X X X X X X X X X X X lt l HM HM HM MM M H lt UM UM H M H t lt l lt lt UM lt lt HM HM M 0 107 U rt U rt U tr U rt U rt U rt U rt U eQ U cQ U cQ U m u cQ U eM U m u m U m U β U rt au au au au au au au xu xu xu xu xu xu au xu xu xu xu xu xu xu xu xu xu xu xu xu xu xu DuC Xu xu xu xu xu xu CN oi Ol N cs rs rs rs rs oi oi ol oi oi !τ W !τ f*r r y y y u rt ffi rt rt n rt n cQ rt rt m n m m m n cQ m m oa m m ffl oQ ffi ffl ffl ffi oQ rt oa cQ rt CQ cQ cQ c cs rs rs rs rs ol oi rs rs cs rs os ol os rs υ u u u u u u u u u u υ υ u u u CS rS CN CN CN cN ol cS CN CN rs rs cs cs rs t UM UM u u u u u u u u u u u u u u u O u y y y y y y y y y y y y y y £ yg. y y y zu zu zυ zu zu zυ zu zu zu zu zu zυ zu zu zu zu 33 DG X HG M M MM MM X X X X HM MG DG X X X X X X ve r- IΛ IΛ ^ U U U U U U U U U U U U U U U U U U U U U o- Ol Ol Ol Ol OS OI OI CS OI OI OI CN CN OI OI OI OI CS CS OI — • CO ^ .^ . M^ MMpU' feX feX fe ftX feX feX feX fcH fe fe fe feK fe fe f u Xe Kfc u u υ X u Xu u ffiu Xu Xu u u u uX u u u Xu ^ |i « u u υ u u u υ υ υ u u u u υ υ u υ u G G G u G G G G G G G G G G G G y u υ u u u u u υ υ u u u u u u u u u u υ u υ u u υ υ u u u u u u u υ u u m u u u u υ u u u u u u u u u u υ υ u υ u u u u u u u u u u u u u u u u u u O U rs p oQ4 Uoi mos Uoι ooQι Urs rtcN UCN poQι Uo4 mrs UcN rtrs Uo4 rtrs Uol rtcs Urs rtcN UCN coQι Urs crQs Uoi rtoι Urs mcs urs moι Urs cQrs UcN moι Urs rtcs UcN Xu Xu Xυ uX Xu Xu Xυ Xu Xu Xu Xu Xu Xu uX puC DuC Xυ Xu Xu Xu Xu Xu uX Xu Xu Xu Xu Xu Xu uX uX Xu uX Xu Xu Xu Xu X X X X X X CO CO ro ro X X X X a υ υ x x a P I δ X a a o a BN CN V P C δ. δ. X u υ £ P cN B rs U CN.8 U CN x a O & 8 £8 C II P P rs rs a a a a I P P u I 9 N CN rs u u g g II II u y y y X X u u u u u P u P a a u a u a u u U U u a cs cN oi oi os rs os ol rs oi rs rs oi rs cs MM W X u G u cQ n rt m rt m rt cQ oQ cQ PQ m m rt OQ rt rt PQ CQ n cQ OQ CQ rt rt rt CQ n n m cQ rt oQ m m m rt ve |-~ IΛ u u u u u u u u u u u υ u u u u υ υ υ u u u u u u u u u u u u u u u u u u IΛ 0 U cN rtcN Uoi moi uoi moi uoi mcN UcN moi UcN rtcN UCN cQrs Urs rtrs Urs rtrs Urs rtrs Urs rtcN Urs mcN Uoi rtoi U rtoi oi oi oi oi oi rs r ux ux xu ux ux xu ux ux ux ux xu ux xu υx ux ux ua xu ua aυ Ua au ua υa υa ua oi ua ua ua ua au ua ua ua au cs cs rs cs rs cN cs rs rs cN oi oi rs rs rs oi cs rs cs rs oi O U U U U cN os cs rs cN CN cN rs rs cN rs rs u -π u-C -uE -uE DuC DuC υ-C uS-i y X y X y y X y X y y a y x y a y a a y y xX y xX y Xx xX y x y x y xX y xX y xX xX xX y x y Xx y Xx y xX y xX xX y m m rt O Q £O Q £C Q rt £rt Zy Zy Zy Zu Zu Zu Zy Zy Zy Zu Zy Z y Zy Zy Zy Zu UZ ZU ZU ZU ZU ZU ZU ZU ZU ZU ZU ZU ZU voo u u u u u u υ u u u υ u u υ u υ υ u u u υ υ u u u u u u u u u u u u u u u Uoi crQs U xcs ua xu u oi rs oi oi rs oi oi oi a rs oi oi oi rs rs rs VO rs rs cN CN cN ol rs rs rs rs cN oi cN oi ol u u u u u u u u u u u u u υ x x x x x x x x x x x x x x x It It It UM O u oi uX rs oi cs oi oi rs rs oi rs rs os oi rs oi cN rs It It cs os rs os rs X X X X X X X X X X X X X w w w ?τ W ^ rτ W W ff fτ? rτ ?τ ?r !τf l'r* X X DC X M u u u u υ υ u u υ u υ u u υ u υ G G G G G G G G G G G G G G u υ y y y y y X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X y y y y y vo IΛ IΛ o OI OI OI OI Ol rS CN OI rs oi oi rs oi rs oi oi rs u υ u u u u u u u u u u u u ^ ^ ^ ^ H^ M^ ^ H? 4 ^ ^ H r ^ H? , ^ H r , ^ ^ fe s It t It It UM u a ua u a ua ua au au ua u au u u au y rt rt y π y rt S y π y r y ι S y r y ι ? y ι r y ι π y ^ y S y ή y S y ri S X ^^ u u u u u ffl m rt ffl rt W ffl m m β PQ PQ W PQ y y y y y y y zu zu zu zu zυ zυ zu zυ zu zu zu uz zu zu zu vO UM UM t UM UM UM UM It UM M It UM UM UM M lt lt l l M - M M HM l UM U- MM M U. U, t- IΛ IΛ ON OI OI OI OI OI OI CN CN cs ol rs oi oi — CN CN MM MM 33 MM D X 33 X X X X X X MM 33 & U U U U U U U U U U U U U U U U _P J HP , u u u u υ u u u u u u u u u u P y - xu ux xυ xu xυ ux ux ux xu ux ux xu xu xu xυ υx rt y rt y rt y x x x x x x x x x x x x x x x x a a a a a a a a a a a a a a a a a a u u u VO ι-~ IΛ u u u u u u u u u u u u u υ υ u u u υ u u u u u u υ υ υ u u u u u u u u u IΛ O 123 U m u xu xu xu CN rs os oi oi oi Ol ol N CN rs s rs rs rs os rs TI¬ C U Ux U U U U ^ ^ " < ^ ^ < ^ ^ ^ < ^ ^ ^* ^ κ^ * < ^ ^* ? < * ?^* ^^ ^^ fe χ & χ fex χ χ χ x χ x x χ χ u G G G G y y y y y y y y y y y y y y y y y y y y y y y y y y y u u u u u U rt cQ CQ m m pQ PQ PQ PQ rt rt cQ cQ α n cQ CQ a m ca cQ CQ CQ rt rt rt m m rt rt PQ r- ■Λ u u u υ u u u υ u u υ u υ u u u u u u u u u u u u u u u u u u u u u u u υ IΛ o moι ucN ooQι Uoi rtoι au au au au aυ X X ol os oi ol rS CN oi cN rs ol oi oi rs rs oi CS u u υ u u υ υ u u u u u u u υ υ CN CN CN CS CS cN CN OI OI CS OI OI rS rS X HM MM HM X X MC X X HG DC M M X X ua Xu uX u uX υX uX uX uX uX Xu υX Xu uX Xυ uX S y ? y ! ? y ? n y n y n y n y S y S y n y n y n y n y n y n y Z zu zu zO zu zO zu zu zu zu zu zu zu zu zu zu zu zu zu zu VO IΛ u u u u u u u υ u u u u u u u u υ u u u u u u u υ u u u u u u u u u υ u IΛ Ov U rs rtoi Us ooQs Uoi moi urs mcN Uoi rtoi Urs rtoi Urs rtrs UrS ooQi Urs rtcN UCN rtrs UcN pcQN UCN moi Urs rto! u X Xu Xu Xu Xu Xu uX Xu Xu uX Xu Xu Xu Xu Xu uX Xu uDC uX Xu uX Xu Xu Xu uX uX — ■ — cN os cs rs rs cN oi oi os rs os rs os rs VO rs x x x x x S x χ , x' x υ υ υ υ υ υ u υ υ u u u u υ υ u u u u u u u u u u u g g δ δ δ δ δ δ δ δ δ δ δ δ δ δ uz zu zu uz zu uz uz uz zu zu zu zu zu zu zu uz zu zu zu zu uz zu zu zu uz uz VO r- IΛ u u u u u u u u u u u u u u u u u u u u u u u u u u IΛ r- ON O CHF H CH 2 OCH 3 C0 2 CH 2 CH 3 CHF H CH 2 OCH 3 C(0)N(CH 2 CH 3 ) 2 CHF H CH 2 OCH 3 C(0)NHCH 3 CHF H CH 2 CN QO) — N O CHF H CH 2 SCH 3 C0 2 CH 2 CH 3 CHF H CH 2 SCH 3 C(0)N(CH 2 CH 3 ) 2 CHF H CH 2 SCH 3 C(0)NHCH 3 CHF H CH 2 SCH 3 QO) — N H CH 2 CN C0 2 CH 2 CH 3 CHCl H CH 2 CN C(0)N(CH 2 CH 3 ) 2 CHCl C0 2 CH 2 CH 3 CHCl H CH 2 SCH 3 H CH 2 SCH 3 C(0)N(CH 2 CH 3 ) 2 CHCl H CH 2 S0 2 CH 3 C0 2 CH 2 CH 3 CHCl H CH 2 S0 2 CH 3 C(0)N(CH 2 CH 3 ) 2 CHCl CHBr H CH 2 C1 C0 2 CH 2 CH 3 N(CH 2 CH 3 ) 2 CHBr H CH 2 C1 C(0) CHBr H CH 2 Br C0 2 CH 2 CH 3 CHBr H CH 2 Br C(0)N(CH 2 CH 3 ) 2 CHBr H CH 2 Br C(0)NHCH 3 CHBr H CH 2 F C0 2 CH 2 CH 3 CHBr H CH 2 F C(0)N(CH 2 CH 3 ) 2 CHBr H CH 2 F C(0)NHCH 3 CHBr H CH 2 F QO) — N O CHBr H CH 2 OCH 3 C0 2 CH 2 CH 3 CHBr H CH 2 OCH 3 C(0)N(CH 2 CH 3 ) 2 CHBr H CH 2 OCH 3 C(0)NHCH 3 CHBr H CH 2 CN C0 2 CH 2 CH 3 CHBr H CH 2 CN C(0)N(CH 2 CH 3 ) 2 CHBr H CH 2 CN C(0)NHCH 3 CHBr H CH 2 S0 2 CH 3 C(0)N(CH 2 CH 3 ) 2 CHBr H CH 2 S0 2 CH 3 C(0)NHCH 3 CHBr H CH 2 S0 2 CH 3 QO) — N O Formulation/Utility Compounds of this invention will generally be used as a formulation or composition with an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent or a surfactant. 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 liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like which optionally can be thickened into gels. Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible ("wettable") or water-soluble. 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. Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation. 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 Water-Dispersible and Water-soluble Granules, Tablets and Powders Suspensions, Emulsions, Solutions 5-50 40-95 0-15 (including Emulsifiable Concentrates) Dusts 1-25 70-99 0-5 Granules and Pellets 001n99 5-99 99 0-15 High Strength Compositions 90-99 0-10 0-2 Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon 's Detergents and Emuls if iers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity. Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, NN-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and polyoxyethylene/polyoxypropylene block copolymers. Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Liquid diluents include, for example, water, N,N-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4- methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol. Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 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. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566. For further information regarding the art of formulation, see U.S. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41 ; U.S. 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. 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; and Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989. 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-J. Example A High Strength Concentrate Compound 23 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0%. Example B Wettable Powder Compound 25 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%. Example C Granule Compound 21 10.0% attapulgite granules (low volatile matter, 0.71/0.30 mm; U.S.S. No. 25-50 sieves) 90.0%. Example D Extruded Pellet Compound 52 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium magnesium bentonite 59.0%. Test results indicate that the compounds of the present invention are highly active preemergent and postemergent herbicides or plant growth regulants. 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. Some of the compounds are useful for the control of selected grass and broadleaf weeds with tolerance to important agronomic crops which include but are 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). 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. Compounds of this invention can be used alone or in combination with other commercial herbicides, insecticides or fungicides. Compounds of this invention can also be used in combination with commercial herbicide safeners such as benoxacor, dichlormid and furilazole to increase safety to certain crops. 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, ametryn, amidosulfuron, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azimsulfuron, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, bifenox, bromacil, bromoxynil, bromoxynil octanoate, butachlor, butralin, butylate, chlomethoxyfen, chloramben, chlorbromuron, chloridazon, chlorimuron-ethyl, chlornitrofen, chlorotoluron, chlorpropham, chlorsulfuron, chlorthal-dimethyl, cinmethylin, cinosulfuron, clethodim, clomazone, clopyralid, clopyralid-olamine, cyanazine, cycloate, cyclosulfamuron, 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, 2-[4,5-dihydro-4-methyl-4-(l-methylethyl)-5- oxo-lH-imidazol-2-yl]-5-methyl-3-pyridinecarboxylic acid (AC 263,222), difenzoquat metilsulfate, diflufenican, dimepiperate, dimethenamid, dimethylarsinic acid and its sodium salt, dinitramine, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethofumesate, ethyl α,2-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-lH-l,2,4-triazol-l-yl]- 4-fluorobenzenepropanoate (F8426), fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, fluazifop-butyl, fluazifop-P-butyl, fluchloralin, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupoxam, fluridone, flurochloridone, fluroxypyr, fomesafen, fosamine-ammonium, glufosinate, glufosinate-ammonium, glyphosate, glyphosate-isopropylammonium, glyphosate-sesquisodium, glyphosate-trimesium, halosulfuron-methyl, haloxyfop-ethyl, haloxyfop-methyl, hexazinone, imazamethabenz-methyl, imazamox (AC 299 263), imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, ioxynil, ioxynil octanoate, ioxynil-sodium, isoproturon, isouron, isoxaben, isoxaflutole (RPA 201772), lactofen, lenacil, linuron, maleic hydrazide, MCPA and its dimethylammonium, potassium and sodium salts, MCPA-isoctyl, mecoprop, mecoprop-P, mefenacet, mefluidide, metam-sodium, methabenzthiazuron, methyl [[2-chloro-4-fluoro-5-[(tetrahydro-3-oxo- lH,3H-[ 1 ,3,4]thiadiazolo[3,4- α]pyridazin-l-ylidene)amino]phenyl]thioacetate (KTΗ 9201), methylarsonic acid and its calcium, monoammonium, monosodium and disodium salts, methyl [[[l-[5-[2-chloro-4- (trifluoromethyl)phenoxy]-2-nitrophenyl]-2-methoxyethylidene]amino]oxy]acetate (AKΗ-7088), methyl 5-[[[[(4,6-dimethyl-2- pyrimidinyl)amino]carbonyl]amino]sulfonyl]-l-(2-pyridinyl)-lH-pyrazole-4-carboxylate (NC-330), metobenzuron, metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl, molinate, monolinuron, napropamide, naptalam, neburon, nicosulfuron, norflurazon, oryzalin, oxadiazon, 3-oxetanyl 2-[[[[(4,6-dimethyl-2- pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoate (CGA 277476), oxyfluorfen, paraquat dichloride, pebulate, pendimethalin, perfluidone, phenmedipham, picloram, picloram-potassium, pretilachlor, primisulfuron-methyl, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propyzamide, prosulfuron, pyrazolynate, pyrazosulfuron-ethyl, pyridate, pyrithiobac, pyrithiobac-sodium, quinclorac, quizalof op-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, sethoxydim, siduron, simazine, sulcotrione (ICIA0051), sulfentrazone, sulfometuron-methyl, TCA, TCA-sodium, tebuthiuron, terbacil, terbuthylazine, terbutryn, thenylchlor, thiafluamide (BAY 11390), thifensulfuron-methyl, thiobencarb, tralkoxydim, tri-allate, triasulfuron, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tridiphane, trifluralin, triflusulfuron-methyl, and vernolate. In certain instances, combinations with other herbicides having a similar spectrum of control but a different mode of action will be particularly advantageous for preventing the development of resistant weeds. Certain combinations of compounds of this invention with other herbicides may provide synergistic herbicidal effects on weeds or may provide enhanced crop safety. Preferred for better control of undesired vegetation in corn (e.g., lower use rate, broader spectrum of weeds controlled, or enhanced crop safety) or for preventing the development of resistant weeds in corn are mixtures of a compound of this invention with one or more of the herbicides selected from the group rimsulfuron, thifensulfuron- methyl, chlorimuron-ethyl, nicosulfuron, prosulfuron, primsulfuron, atrazine, terbuthylazine, dicamba, 2,4-D, bomoxynil, pyridate, sulcotrione, glufosinate, glyphosate, glyphosate-trimesium, fluthiacet-methyl, quizalofop-p-ethyl, bentazone, clopyralid, flumetsulam, halosulfuron, sethoxydim, flumiclorac-pentyl, imozamox, acetachlor, alachlor, dimethenamid, isoxaflutole, metolachlor, metribuzin, pendimethalin, and thiafluimid. Preferred for better control of undesired vegetation in soybeans (e.g., lower use rate, broader spectrum of weeds controlled, or enhanced crop safety) or for preventing the development of resistant weeds in soybeans are mixtures of a compound of this invention with one or more of the herbicides selected from the group chlorimuron-ethyl, thifensulfuron-methyl, clethodim, sethoxydim, fluazifop-p-butyl, haloxyfop, imazethapyr, imozamox, imazaquin, glufosinate, glyphosate, glyphosate-trimesium, lactofen, fluthiacet-methyl, quizalofop-p-ethyl, acifluorfen-sodium, oxasulfuron, imazameth, flumiclorac-pentyl, and bentazone. Preferred for better control of undesired vegetation in winter wheat, winter barley, spring wheat, spring barley, and peas (e.g., lower use rate, broader spectrum of weeds controlled, or enhanced crop safety) or for preventing the development of resistant weeds in winter wheat, winter barley, spring wheat, spring barley, and peas are mixtures of a compound of this invention with one or more of the herbicides selected from the group tribenuron-methyl, thifensulfuron-methyl, metsulfuron-methyl, chlorsulfuron, triasulfuron, 2,4-D. dicamba, bromoxynil, MCPA, fluroxypyr, clopyralid, fenoxaprop, fenchlorazole, diclofop, tralkoxydim, clodinafop, cloquintocet-mexyl, imazamethabenz, sulfosulfuron, difenzoquat, propanil, prosulfuron, metribuzin, glyphosate, triallate, trifluralin, paraquat, diallate, linuron, diflufenican, pendimethalin, cyanazine, neburon, terbutryn, prosulfocarb, isoproturon, chlortoluron, methabenzthiazuron, metoxuron, simazine, ioxynil, mecoprop, metosulam, fluroglycophen-ethyl, flamprop-M-isopropyl, and benzoylpropethyl. Specifically preferred mixtures for use in corn are selected from the group: a) (6S-cis)- 1 -chloro-V-[2-chloro-4-fluoro-5-(6-fluorotetrahydro- 1 ,3-dioxo- 1H- pyrrolo[l,2-c]imidazol-2(3H)-yl)phenyl]methanesulfonamide (mixture partner A, generally applied at a rate of 0.1 to 50 g/ha, preferably applied at a rate of 1 to 20 g/ha) in combination with: Combination 1 is generally used in a ratio of A to B of 1:500 to 50: 1, preferably 1 :20 to 4: 1, with B being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha. Combination 2 is generally used in a ratio of A to B of 1:500 to 50: 1, preferably 1 : 10 to 20: 1 , with B being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 3 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 4 is generally used in a ratio of A to Bl of 1:500 to 50: 1, preferably 1:20 to 4: 1, and a ratio of A to B2 of 1:500 to 50: 1, preferably 1 : 10 to 20: 1, with B 1 being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha, and B2 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 5 is generally used in a ratio of A to B of 1 :2,000 to 5: 1, preferably 1:50 to 2: 1, with B being applied at a rate of 10 to 200 g ha, preferably 10 to 50 g/ha. Combination 6 is generally used in a ratio of A to B3 of 1 :500 to 50: 1 , preferably 1 :20 to 4: 1 , and a ratio of A to B4 of 1 :2,000 to 5 : 1 , preferably 1:50 to 2: 1, with B3 being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha, and B4 being applied at a rate of 10 to 200 g/ha, preferably 10 to 50 g/ha. Combination 7 is generally used in a ratio of A to B5 of 1 :500 to 50: 1 , preferably 1 :20 to 4: 1 , and a ratio of A to B6 of 1:2,000 to 5: 1, preferably 1:50 to 2: 1, and a ratio of A to B7 of 1:500 to 50: 1, preferably 1: 10 to 20:1, with B5 being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha, and B6 being applied at a rate of 10 to 200 g/ha, preferably 10 to 50 g/ha, and B7 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 8 is generally used in a ratio of A to B of 1 : 1 ,000 to 5: 1 , preferably 1 :60 to 1 : 1 , with B being applied at a rate of 10 to 100 g/ha, preferably 20 to 60 g/ha. Combination 9 is generally used in a ratio of A to B8 of 1 : 1 ,000 to 5: 1 , preferably 1 :60 to 1: 1, and a ratio of A to B9 of 1 : 1 ,000 to 5: 1 , preferably 1 :60 to 1 : 1 , with B8 being applied at a rate of 10 to 100 g/ha, preferably 20 to 60 g/ha, and B9 being applied at a rate of 10 to 100 g/ha, preferably 20 to 60 g/ha. Combination 10 is generally used in a ratio of A to B of 1 :30,000 to 1 : 10, preferably 1 : 1 ,000 to 1 :25, with B being applied at a rate of 500 to 3,000 g/ha, preferably 500 to 1,000 g/ha. Combination 11 is generally used in a ratio of A to B of 1 :50,000 to 1 : 10, preferably 1 :2,000 to 1 :25, with B being applied at a rate of 500 to 5,000 g/ha, preferably 500 to 2,000 g/ha. Combination 12 is generally used in a ratio of A to B of 1 : 10,000 to 1 :2, preferably 1 :500 to 1 :5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 500 g/ha. Combination 13 is generally used in a ratio of A to B of 1 : 10,000 to 1 :2, preferably 1:500 to 1 :5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 500 g/ha. Combination 14 is generally used in a ratio of A to B of 1 : 10,000 to 1:2, preferably 1 :500 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 500 g/ha. Combination 15 is generally used in a ratio of A to B of 1:30,000 to 1:40, preferably 1:1,000 to 1: 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. Combination 16 is generally used in a ratio of A to B of 1:30,000 to 1:40, preferably 1: 1,000 to 1: 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. Combination 17 is generally used in a ratio of A to B of 1 :30,000 to 1 :40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1 ,000 g/ha. Combination 18 is generally used in a ratio of A to B of 1:30,000 to 1:40, preferably 1: 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. Combination 19 is generally used in a ratio of A to B of 1:30,000 to 1:40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. b) (6S-cιs)-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro- 1 ,3-dioxo- 1H- pyrrolo[ 1 ,2-c]imidazol-2(3H)-yl)phenyl]-N-[(chloromethyl)sulfonyl]acetamide (mixture partner A, generally applied at a rate of 0.1 to 50 g/ha, preferably applied at a rate of 1 to 20 g/ha) in combination with: Combination 1 is generally used in a ratio of A to B of 1 :500 to 50: 1 , preferably 1 :20 to 4: 1 , with B being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha. Combination 2 is generally used in a ratio of A to B of 1:500 to 50: 1, preferably 1 : 10 to 20: 1, with B being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 3 is generally used in a ratio of A to B of 1: 1,000 to 50: 1, preferably 1:20 to 20: 1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 4 is generally used in a ratio of A to B 1 of 1 :500 to 50: 1 , preferably 1 :20 to 4: 1 , and a ratio of A to B2 of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1 , with B 1 being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha, and B2 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 5 is generally used in a ratio of A to B of 1 :2,000 to 5: 1 , preferably 1 :50 to 2: 1 , with B being applied at a rate of 10 to 200 g/ha, preferably 10 to 50 g/ha. Combination 6 is generally used in a ratio of A to B3 of 1:500 to 50: 1, preferably 1:20 to 4: 1, and a ratio of A to B4 of 1:2,000 to 5:1, preferably 1:50 to 2: 1, with B3 being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha, and B4 being applied at a rate of 10 to 200 g/ha, preferably 10 to 50 g/ha. Combination 7 is generally used in a ratio of A to B5 of 1 :500 to 50: 1 , preferably 1 :20 to 4: 1 , and a ratio of A to B6 of 1 :2,000 to 5:1, preferably 1:50 to 2: 1, and a ratio of A to B7 of 1:500 to 50: 1, preferably 1: 10 to 20: 1, with B5 being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha, and B6 being applied at a rate of 10 to 200 g/ha, preferably 10 to 50 g/ha, and B7 being applied at a rate of 1 to 50 g ha, preferably 1 to 10 g/ha. Combination 8 is generally used in a ratio of A to B of 1 : 1 ,000 to 5: 1 , preferably 1 : 60 to 1:1, with B being applied at a rate of 10 to 100 g/ha, preferably 20 to 60 g/ha. Combination 9 is generally used in a ratio of A to B 8 of 1:1,000 to 5:1, preferably 1:60 to 1:1, and a ratio of A to B9 of 1: 1,000 to 5: 1, preferably 1:60 to 1: 1, with B8 being applied at a rate of 10 to 100 g/ha, preferably 20 to 60 g/ha, and B9 being applied at a rate of 10 to 100 g/ha, preferably 20 to 60 g/ha. Combination 10 is generally used in a ratio of A to B of 1 :30,000 to 1 : 10, preferably 1 : 1 ,000 to 1 :25, with B being applied at a rate of 500 to 3,000 g/ha, preferably 500 to 1,000 g/ha. Combination 11 is generally used in a ratio of A to B of 1:50,000 to 1:10, preferably 1:2,000 to 1:25, with B being applied at a rate of 500 to 5,000 g/ha, preferably 500 to 2,000 g/ha. Combination 12 is generally used in a ratio of A to B of 1:10,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 500 g/ha. Combination 13 is generally used in a ratio of A to B of 1 : 10,000 to 1 :2, preferably 1 :500 to 1 :5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 500 g/ha. Combination 14 is generally used in a ratio of A to B of 1 : 10,000 to 1 :2, preferably 1 :500 to 1 :5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 500 g/ha. Combination 15 is generally used in a ratio of A to B of 1 :30,000 to 1 :40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. Combination 16 is generally used in a ratio of A to B of 1:30,000 to 1:40, preferably 1: 1,000 to 1: 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. Combination 17 is generally used in a ratio of A to B of 1 : 30,000 to 1 :40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. Combination 18 is generally used in a ratio of A to B of 1:30,000 to 1:40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1 ,000 g/ha. Combination 19 is generally used in a ratio of A to B of 1 :30,000 to 1 :40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. c) (65-c 5)-l-chloro- /-[2-chloro-5-(6-chlorotetrahydro-l,3-dioxo-lH- pyrrolo[ 1 ,2-c]imidazol-2(3H)-yl)-4-fluorophenyl]methanesulfonamide (mixture partner A, generally applied at a rate of 0.1 to 50 g/ha, preferably applied at a rate of 1 to 20 g/ha) in combination with: Combination 1 is generally used in a ratio of A to B of 1:500 to 50:1, preferably 1 :20 to 4: 1 , with B being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha. Combination 2 is generally used in a ratio of A to B of 1 :500 to 50: 1, preferably 1 : 10 to 20: 1 , with B being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 3 is generally used in a ratio of A to B of 1 : 1,000 to 50: 1 , preferably 1 :20 to 20: 1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 4 is generally used in a ratio of A to Bl of 1:500 to 50:1, preferably 1:20 to 4: 1 , and a ratio of A to B2 of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1 , with B 1 being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha, and B2 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 5 is generally used in a ratio of A to B of 1:2,000 to 5: 1, preferably 1:50 to 2: 1, with B being applied at a rate of 10 to 200 g/ha, preferably 10 to 50 g/ha. Combination 6 is generally used in a ratio of A to B 3 of 1 :500 to 50: 1 , preferably 1 :20 to 4: 1 , and a ratio of A to B4 of 1 :2,000 to 5 : 1 , preferably 1 :50 to 2: 1, with B3 being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha, and B4 being applied at a rate of 10 to 200 g/ha, preferably 10 to 50 g/ha. Combination 7 is generally used in a ratio of A to B5 of 1 :500 to 50: 1 , preferably 1 :20 to 4: 1 , and a ratio of A to B6 of 1:2,000 to 5:1, preferably 1:50 to 2: 1, and a ratio of A to B7 of 1:500 to 50: 1, preferably 1:10 to 20:1, with B5 being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha, and B6 being applied at a rate of 10 to 200 g/ha, preferably 10 to 50 g/ha, and B7 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 8 is generally used in a ratio of A to B of 1 : 1 ,000 to 5: 1 , preferably 1 :60 to 1 : 1 , with B being applied at a rate of 10 to 100 g/ha, preferably 20 to 60 g/ha. Combination 9 is generally used in a ratio of A to B8 of 1 : 1 ,000 to 5 : 1 , preferably 1 :60 to 1:1, and a ratio of A to B9 of 1:1,000 to 5: 1, preferably 1:60 to 1:1, with B 8 being applied at a rate of 10 to 100 g/ha, preferably 20 to 60 g/ha, and B9 being applied at a rate of 10 to 100 g/ha, preferably 20 to 60 g ha. Combination 10 is generally used in a ratio of A to B of 1 :30,000 to 1 : 10, preferably 1: 1,000 to 1:25, with B being applied at a rate of 500 to 3,000 g/ha, preferably 500 to 1,000 g/ha. Combination 11 is generally used in a ratio of A to B of 1:50,000 to 1: 10, preferably 1:2,000 to 1:25, with B being applied at a rate of 500 to 5,000 g/ha, preferably 500 to 2,000 g/ha. Combination 12 is generally used in a ratio of A to B of 1 : 10,000 to 1 :2, preferably 1 :500 to 1 :5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 500 g/ha. Combination 13 is generally used in a ratio of A to B of 1:10,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 500 g/ha. Combination 14 is generally used in a ratio of A to B of 1 : 10,000 to 1 :2, preferably 1 :500 to 1 :5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 500 g/ha. Combination 15 is generally used in a ratio of A to B of 1:30,000 to 1:40, preferably 1: 1,000 to 1: 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. Combination 16 is generally used in a ratio of A to B of 1 : 30,000 to 1 :40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. Combination 17 is generally used in a ratio of A to B of 1:30,000 to 1:40, preferably 1:1,000 to 1:10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. Combination 18 is generally used in a ratio of A to B of 1 :30,000 to 1 :40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1 ,000 g/ha. Combination 19 is generally used in a ratio of A to B of 1 :30,000 to 1 :40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. d) (6S-cw)- -[2-chloro-5-(6-chlorotetrahydro-l,3-dioxo-lH-pyrrolo[l,2- c]imidazol-2(3H)-yl)-4-fluorophenyl)-N-[(chloromethyl)sulfonyl]acetamide (mixture partner A, generally applied at a rate of 0.1 to 50 g/ha, preferably applied at a rate of 1 to 20 g/ha) in combination with: Combination 1 is generally used in a ratio of A to B of 1:500 to 50:1, preferably 1 :20 to 4: 1 , with B being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha. Combination 2 is generally used in a ratio of A to B of 1 :500 to 50: 1, preferably 1 : 10 to 20: 1 , with B being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 3 is generally used in a ratio of A to B of 1:1,000 to 50: 1, preferably 1:20 to 20: 1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 4 is generally used in a ratio of A to B 1 of 1 :500 to 50: 1 , preferably 1 :20 to 4: 1 , and a ratio of A to B2 of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1 , with B 1 being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha, and B2 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 5 is generally used in a ratio of A to B of 1 :2,000 to 5: 1 , preferably 1 :50 to 2: 1 , with B being applied at a rate of 10 to 200 g/ha, preferably 10 to 50 g/ha. Combination 6 is generally used in a ratio of A to B 3 of 1:500 to 50: 1, preferably 1:20 to 4: 1, and a ratio of A to B4 of 1:2,000 to 5: 1, preferably 1:50 to 2: 1, with B3 being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha, and B4 being applied at a rate of 10 to 200 g/ha, preferably 10 to 50 g/ha. Combination 7 is generally used in a ratio of A to B5 of 1 :500 to 50: 1 , preferably 1 :20 to 4: 1 , and a ratio of A to B6 of 1:2,000 to 5:1, preferably 1:50 to 2: 1, and a ratio of A to B7 of 1:500 to 50: 1, preferably 1: 10 to 20: 1, with B5 being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha, and B6 being applied at a rate of 10 to 200 g/ha, preferably 10 to 50 g/ha, and B7 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 8 is generally used in a ratio of A to B of 1 : 1 ,000 to 5: 1 , preferably 1 : 60 to 1: 1, with B being applied at a rate of 10 to 100 g/ha, preferably 20 to 60 g/ha. Combination 9 is generally used in a ratio of A to B8 of 1 : 1 ,000 to 5 : 1 , preferably 1 :60 to 1: 1, and a ratio of A to B9 of 1 : 1 ,000 to 5: 1 , preferably 1 :60 to 1 : 1 , with B8 being applied at a rate of 10 to 100 g/ha, preferably 20 to 60 g/ha, and B9 being applied at a rate of 10 to 100 g/ha, preferably 20 to 60 g/ha. Combination 10 is generally used in a ratio of A to B of 1 :30,000 to 1 : 10, preferably 1 : 1 ,000 to 1 :25, with B being applied at a rate of 500 to 3,000 g/ha, preferably 500 to 1,000 g/ha. Combination 11 is generally used in a ratio of A to B of 1:50,000 to 1:10, preferably 1:2,000 to 1:25, with B being applied at a rate of 500 to 5,000 g/ha, preferably 500 to 2,000 g/ha. Combination 12 is generally used in a ratio of A to B of 1:10,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 500 g/ha. Combination 13 is generally used in a ratio of A to B of 1 : 10,000 to 1 :2, preferably 1 :500 to 1 :5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 500 g/ha. Combination 14 is generally used in a ratio of A to B of 1 : 10,000 to 1 :2, preferably 1 :500 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 500 g/ha. Combination 15 is generally used in a ratio of A to B of 1 :30,000 to 1 :40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. Combination 16 is generally used in a ratio of A to B of 1 : 30,000 to 1 :40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. Combination 17 is generally used in a ratio of A to B of 1:30,000 to 1 :40, preferably 1: 1,000 to 1: 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. Combination 18 is generally used in a ratio of A to B of 1:30,000 to 1:40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1 ,000 g/ha. Combination 19 is generally used in a ratio of A to B of 1 :30,000 to 1 :40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. e) (65-cw)-l-chloro-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro-l,3-dioxo-lH- pyrrolo[l,2-c]imidazol-2(3H)-yl)phenyl]methanesulfonamide monosodium salt (mixture partner A, generally applied at a rate of 0.1 to 50 g/ha, preferably applied at a rate of 1 to 20 g/ha) in combination with: Combination 1 is generally used in a ratio of A to B of 1:500 to 50: 1, preferably 1:20 to 4: 1, with B being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha. Combination 2 is generally used in a ratio of A to B of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1, with B being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 3 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 4 is generally used in a ratio of A to B 1 of 1 :500 to 50: 1 , preferably 1 :20 to 4: 1 , and a ratio of A to B2 of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1 , with B 1 being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha, and B2 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 5 is generally used in a ratio of A to B of 1 :2,000 to 5: 1 , preferably 1 :50 to 2: 1, with B being applied at a rate of 10 to 200 g ha, preferably 10 to 50 g/ha. Combination 6 is generally used in a ratio of A to B3 of 1:500 to 50: 1, preferably 1:20 to 4: 1, and a ratio of A to B4 of 1:2,000 to 5: 1, preferably 1:50 to 2: 1, with B3 being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha, and B4 being applied at a rate of 10 to 200 g/ha, preferably 10 to 50 g/ha. Combination 7 is generally used in a ratio of A to B5 of 1 :500 to 50: 1 , preferably 1 :20 to 4: 1 , and a ratio of A to B6 of 1:2,000 to 5: 1, preferably 1:50 to 2: 1, and a ratio of A to B7 of 1:500 to 50: 1, preferably 1:10 to 20:1, with B5 being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha, and B6 being applied at a rate of 10 to 200 g/ha, preferably 10 to 50 g/ha, and B7 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 8 is generally used in a ratio of A to B of 1 : 1 ,000 to 5: 1 , preferably 1 : 60 to 1: 1, with B being applied at a rate of 10 to 100 g/ha, preferably 20 to 60 g/ha. Combination 9 is generally used in a ratio of A to B8 of 1: 1,000 to 5:1, preferably 1:60 to 1: 1, and a ratio of A to B9 of 1: 1,000 to 5: 1, preferably 1:60 to 1: 1, with B8 being applied at a rate of 10 to 100 g/ha, preferably 20 to 60 g/ha, and B9 being applied at a rate of 10 to 100 g/ha, preferably 20 to 60 g/ha. Combination 10 is generally used in a ratio of A to B of 1:30,000 to 1: 10, preferably 1:1,000 to 1:25, with B being applied at a rate of 500 to 3,000 g/ha, preferably 500 to 1,000 g/ha. Combination 11 is generally used in a ratio of A to B of 1:50,000 to 1:10, preferably 1:2,000 to 1:25, with B being applied at a rate of 500 to 5,000 g/ha, preferably 500 to 2,000 g/ha. Combination 12 is generally used in a ratio of A to B of 1:10,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 500 g/ha. Combination 13 is generally used in a ratio of A to B of 1: 10,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 500 g/ha. Combination 14 is generally used in a ratio of A to B of 1 : 10,000 to 1 :2, preferably 1 :500 to 1 :5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 500 g/ha. Combination 15 is generally used in a ratio of A to B of 1 :30,000 to 1 :40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. Combination 16 is generally used in a ratio of A to B of 1:30,000 to 1:40, preferably 1:1,000 to 1:10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1 ,000 g/ha. Combination 17 is generally used in a ratio of A to B of 1:30,000 to 1:40, preferably 1:1,000 to 1:10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. Combination 18 is generally used in a ratio of A to B of 1:30,000 to 1:40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1 ,000 g/ha. Combination 19 is generally used in a ratio of A to B of 1 :30,000 to 1 :40, preferably 1 : 1 ,000 to 1:10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. f) (65-c 5)-l-chloro-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro- l,3-dioxo-lH- pyrrolo[ 1 ,2-c]imidazol-2(3H)-yl)phenyl]methanesulfonamide monopotassium salt (mixture partner A, generally applied at a rate of 0.1 to 50 g/ha, preferably applied at a rate of 1 to 20 g/ha) in combination with: Combination 1 is generally used in a ratio of A to B of 1:500 to 50: 1, preferably 1 :20 to 4: 1 , with B being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha. Combination 2 is generally used in a ratio of A to B of 1:500 to 50: 1, preferably 1: 10 to 20: 1 , with B being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 3 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 4 is generally used in a ratio of A to Bl of 1:500 to 50: 1, preferably 1:20 to 4: 1, and a ratio of A to B2 of 1:500 to 50: 1, preferably 1: 10 to 20:1, with Bl being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha, and B2 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 5 is generally used in a ratio of A to B of 1 :2,000 to 5: 1, preferably 1 :50 to 2: 1, with B being applied at a rate of 10 to 200 g/ha, preferably 10 to 50 g/ha. Combination 6 is generally used in a ratio of A to B3 of 1 :500 to 50: 1 , preferably 1 :20 to 4: 1 , and a ratio of A to B4 of 1 :2,000 to 5 : 1 , preferably 1 :50 to 2: 1 , with B3 being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha, and B4 being applied at a rate of 10 to 200 g/ha, preferably 10 to 50 g/ha. Combination 7 is generally used in a ratio of A to B5 of 1:500 to 50: 1 , preferably 1 :20 to 4: 1, and a ratio of A to B6 of 1:2,000 to 5: 1, preferably 1:50 to 2: 1, and a ratio of A to B7 of 1:500 to 50: 1 , preferably 1 : 10 to 20: 1 , with B5 being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha, and B6 being applied at a rate of 10 to 200 g/ha, preferably 10 to 50 g/ha, and B7 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 8 is generally used in a ratio of A to B of 1 : 1 ,000 to 5: 1 , preferably 1 :60 to 1 : 1 , with B being applied at a rate of 10 to 100 g/ha, preferably 20 to 60 g/ha. Combination 9 is generally used in a ratio of A to B8 of 1 : 1 ,000 to 5: 1 , preferably 1 :60 to 1 : 1 , and a ratio of A to B9 of 1:1,000 to 5:1, preferably 1:60 to 1:1, with B8 being applied at a rate of 10 to 100 g/ha, preferably 20 to 60 g/ha, and B9 being applied at a rate of 10 to 100 g/ha, preferably 20 to 60 g/ha. Combination 10 is generally used in a ratio of A to B of 1 :30,000 to 1 : 10, preferably 1 : 1 ,000 to 1 :25, with B being applied at a rate of 500 to 3,000 g/ha, preferably 500 to 1,000 g/ha. Combination 11 is generally used in a ratio of A to B of 1:50,000 to 1:10, preferably 1:2,000 to 1:25, with B being applied at a rate of 500 to 5,000 g/ha, preferably 500 to 2,000 g ha. Combination 12 is generally used in a ratio of A to B of 1 : 10,000 to 1 :2, preferably 1 :500 to 1 :5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 500 g ha. Combination 13 is generally used in a ratio of A to B of 1:10,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 500 g/ha. Combination 14 is generally used in a ratio of A to B of 1 : 10,000 to 1 :2, preferably 1 :500 to 1 :5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 500 g/ha. Combination 15 is generally used in a ratio of A to B of 1 :30,000 to 1 :40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. Combination 16 is generally used in a ratio of A to B of 1:30,000 to 1:40, preferably 1:1,000 to 1:10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. Combination 17 is generally used in a ratio of A to B of 1 :30,000 to 1 :40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. Combination 18 is generally used in a ratio of A to B of 1:30,000 to 1:40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1 ,000 g/ha. Combination 19 is generally used in a ratio of A to B of 1 :30,000 to 1 :40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. g) (6S-cis)- 1 -chloro-N-[2-chloro-5-(6-chlorotetrahydro- 1 ,3-dioxo- 1H- pyrrolo[ 1 ,2-c]imidazol-2(3H)-yl)-4-fluorophenyl]methanesulfonamide monosodium salt (mixture partner A, generally applied at a rate of 0.1 to 50 g/ha, preferably applied at a rate of 1 to 20 g/ha) in combination with: Combination 1 is generally used in a ratio of A to B of 1:500 to 50: 1, preferably 1:20 to 4: 1, with B being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha. Combination 2 is generally used in a ratio of A to B of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1 , with B being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 3 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 4 is generally used in a ratio of A to Bl of 1:500 to 50:1, preferably 1:20 to 4: 1 , and a ratio of A to B2 of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1 , with B 1 being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha, and B2 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 5 is generally used in a ratio of A to B of 1:2,000 to 5: 1, preferably 1:50 to 2: 1, with B being applied at a rate of 10 to 200 g/ha, preferably 10 to 50 g/ha. Combination 6 is generally used in a ratio of A to B3 of 1 :500 to 50: 1 , preferably 1 :20 to 4: 1 , and a ratio of A to B4 of 1 :2,000 to 5: 1 , preferably 1 :50 to 2: 1, with B3 being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha, and B4 being applied at a rate of 10 to 200 g/ha, preferably 10 to 50 g/ha. Combination 7 is generally used in a ratio of A to B5 of 1:500 to 50: 1, preferably 1:20 to 4: 1, and a ratio of A to B6 of 1:2,000 to 5:1, preferably 1:50 to 2: 1, and a ratio of A to B7 of 1:500 to 50:1, preferably 1:10 to 20:1, with B5 being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha, and B6 being applied at a rate of 10 to 200 g/ha, preferably 10 to 50 g/ha, and B7 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 8 is generally used in a ratio of A to B of 1 : 1 ,000 to 5: 1 , preferably 1 :60 to 1: 1, with B being applied at a rate of 10 to 100 g/ha, preferably 20 to 60 g/ha. Combination 9 is generally used in a ratio of A to B8 of 1 : 1 ,000 to 5 : 1 , preferably 1 : 60 to 1: 1, and a ratio of A to B9 of 1:1,000 to 5:1, preferably 1:60 to 1:1, with B8 being applied at a rate of 10 to 100 g/ha, preferably 20 to 60 g/ha, and B9 being applied at a rate of 10 to 100 g/ha, preferably 20 to 60 g/ha. Combination 10 is generally used in a ratio of A to B of 1 :30,000 to 1 : 10, preferably 1 : 1 ,000 to 1 :25, with B being applied at a rate of 500 to 3,000 g/ha, preferably 500 to 1,000 g/ha. Combination 11 is generally used in a ratio of A to B of 1:50,000 to 1:10, preferably 1:2,000 to 1:25, with B being applied at a rate of 500 to 5,000 g/ha, preferably 500 to 2,000 g/ha. Combination 12 is generally used in a ratio of A to B of 1:10,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 500 g/ha. Combination 13 is generally used in a ratio of A to B of 1: 10,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 500 g/ha. Combination 14 is generally used in a ratio of A to B of 1 : 10,000 to 1 :2, preferably 1 :500 to 1 :5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 500 g/ha. Combination 15 is generally used in a ratio of A to B of 1 :30,000 to 1 :40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. Combination 16 is generally used in a ratio of A to B of 1 :30,000 to 1 :40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3 ,000 g/ha, preferably 200 to 1 ,000 g/ha. Combination 17 is generally used in a ratio of A to B of 1 : 30,000 to 1 :40, preferably 1 : 1 ,000 to 1: 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. Combination 18 is generally used in a ratio of A to B of 1:30,000 to 1:40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1 ,000 g/ha. Combination 19 is generally used in a ratio of A to B of 1 :30,000 to 1 :40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. h) (6S- s)-l-chloro-N-[2-chloro-5-(6-chlorotetrahydro-l,3-dioxo-lH- pyrrolof 1 ,2-c]imidazol-2(3H)-yl)-4-fluorophenyl]methanesulfonamide monopotassium salt (mixture partner A, generally applied at a rate of 0.1 to 50 g/ha, preferably applied at a rate of 1 to 20 g/ha) in combination with: Combination 1 is generally used in a ratio of A to B of 1:500 to 50: 1, preferably 1:20 to 4: 1, with B being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha. Combination 2 is generally used in a ratio of A to B of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1 , with B being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 3 is generally used in a ratio of A to B of 1 : 1,000 to 50: 1 , preferably 1 :20 to 20: 1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 4 is generally used in a ratio of A to Bl of 1:500 to 50: 1, preferably 1:20 to 4: 1 , and a ratio of A to B2 of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1 , with B 1 being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha, and B2 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 5 is generally used in a ratio of A to B of 1:2,000 to 5: 1, preferably 1:50 to 2: 1, with B being applied at a rate of 10 to 200 g/ha, preferably 10 to 50 g/ha. Combination 6 is generally used in a ratio of A to B 3 of 1 :500 to 50: 1 , preferably 1 :20 to 4: 1 , and a ratio of A to B4 of 1 :2,000 to 5: 1 , preferably 1 :50 to 2: 1 , with B3 being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha, and B4 being applied at a rate of 10 to 200 g/ha, preferably 10 to 50 g ha. Combination 7 is generally used in a ratio of A to B5 of 1 :500 to 50: 1 , preferably 1 :20 to 4: 1 , and a ratio of A to B6 of 1:2,000 to 5:1, preferably 1:50 to 2: 1, and a ratio of A to B7 of 1:500 to 50: 1, preferably 1:10 to 20:1, with B5 being applied at a rate of 1 to 50 g/ha, preferably 5 to 20 g/ha, and B6 being applied at a rate of 10 to 200 g/ha, preferably 10 to 50 g/ha, and B7 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 8 is generally used in a ratio of A to B of 1 : 1 ,000 to 5: 1 , preferably 1 :60 to 1: 1, with B being applied at a rate of 10 to 100 g/ha, preferably 20 to 60 g/ha. Combination 9 is generally used in a ratio of A to B8 of 1 : 1 ,000 to 5: 1 , preferably 1 :60 to 1 : 1 , and a ratio of A to B9 of 1: 1,000 to 5:1, preferably 1:60 to 1:1, with B8 being applied at a rate of 10 to 100 g/ha, preferably 20 to 60 g/ha, and B9 being applied at a rate of 10 to 100 g/ha, preferably 20 to 60 g/ha. Combination 10 is generally used in a ratio of A to B of 1:30,000 to 1:10, preferably 1:1,000 to 1:25, with B being applied at a rate of 500 to 3,000 g/ha, preferably 500 to 1,000 g/ha. Combination 11 is generally used in a ratio of A to B of 1:50,000 to 1: 10, preferably 1:2,000 to 1:25, with B being applied at a rate of 500 to 5,000 g ha, preferably 500 to 2,000 g ha. Combination 12 is generally used in a ratio of A to B of 1 : 10,000 to 1 :2, preferably 1 :500 to 1 :5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 500 g/ha. Combination 13 is generally used in a ratio of A to B of 1:10,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 500 g/ha. Combination 14 is generally used in a ratio of A to B of 1 : 10,000 to 1 :2, preferably 1 :500 to 1 :5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 500 g/ha. Combination 15 is generally used in a ratio of A to B of 1:30,000 to 1:40, preferably 1:1,000 to 1:10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. Combination 16 is generally used in a ratio of A to B of 1 :30,000 to 1 :40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. Combination 17 is generally used in a ratio of A to B of 1 :30,000 to 1 :40, preferably 1 : 1,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. Combination 18 is generally used in a ratio of A to B of 1:30,000 to 1:40, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g ha, preferably 200 to 1 ,000 g/ha. Combination 19 is generally used in a ratio of A to B of 1 : 30,000 to 1 :40, preferably 1 : 1,000 to 1 : 10, with B being applied at a rate of 200 to 3,000 g/ha, preferably 200 to 1,000 g/ha. Specifically preferred mixtures for use in soybeans are selected from the group: a) (6S-cis)- 1 -chloro-/V-[2-chloro-4-fluoro-5-(6-fluorotetrahydro- 1 ,3-dioxo- 1H- pyrrolo[l,2-c]imidazol-2(3H)-yl)phenyl]methanesulfonamide (mixture partner A, generally applied at a rate of 0.1 to 50 g/ha, preferably applied at a rate of 1 to 20 g/ha) in combination with: Combination 1 is generally used in a ratio of A to B of 1:1,000 to 10:1, preferably 1 :25 to 4: 1 , with B being applied at a rate of 5 to 100 g/ha, preferably 5 to 25 g ha. Combination 2 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1:10 to 10: 1, with B being applied at a rate of 1 to 100 g ha, preferably 1 to 10 g/ha. Combination 3 is generally used in a ratio of A to B 1 of 1 : 1 ,000 to 50: 1 , preferably 1 :50 to 4: 1 , and ratio of A to B2 of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1 , with B 1 being applied at a rate of 1 to 100 g/ha, preferably 5 to 50 g/ha, and B2 being applied at a rate of 1 to 50 g ha, preferably 1 to 10 g/ha. Combination 4 is generally used in a ratio of A to B of 1 :5,000 to 50: 1 , preferably 1 :50 to 2: 1 , with B being applied at a rate of 1 to 500 g/ha, preferably 10 to 50 g ha. Combination 5 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 6 is generally used in a ratio of A to B of 1 :5,000 to 5: 1 , preferably 1 :200 to 1 :2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 7 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 8 is generally used in a ratio of A to B of 1 :5,000 to 5: 1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 9 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1: 100 to 2: 1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 10 is generally used in a ratio of A to B of 1: 10,000 to 1:2, preferably 1:400 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 400 g/ha. Combination 11 is generally used in a ratio of A to B of 1 :40,000 to 1 :2, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 100 to 4,000 g/ha, preferably 200 to 1,000 g/ha. Combination 12 is generally used in a ratio of A to B of 1 :40,000 to 1 :2, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 100 to 4,000 g/ha, preferably 200 to 1,000 g/ha. Combination 13 is generally used in a ratio of A to B of 1 :40,000 to 1 :2, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 100 to 4,000 g/ha, preferably 200 to 1,000 g/ha. Combination 14 is generally used in a ratio of A to B of 1:5,000 to 50:1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. b) (6S-c.s)-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro- 1 ,3-dioxo- 1H- pyrrolo[ 1 ,2-c]imidazol-2(3H)-yl)phenyl]-N-[(chloromethyl)sulfonyl]acetamide (mixture partner A, generally applied at a rate of 0.1 to 50 g/ha, preferably applied at a rate of 1 to 20 g/ha) in combination with: Combination 1 is generally used in a ratio of A to B of 1:1,000 to 10: 1, preferably 1 :25 to 4: 1 , with B being applied at a rate of 5 to 100 g/ha, preferably 5 to 25 g/ha. Combination 2 is generally used in a ratio of A to B of 1:1,000 to 50:1, preferably 1:10 to 10: 1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 10 g/ha. Combination 3 is generally used in a ratio of A to B 1 of 1: 1,000 to 50: 1, preferably 1:50 to 4: 1 , and ratio of A to B2 of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1 , with B 1 being applied at a rate of 1 to 100 g/ha, preferably 5 to 50 g/ha, and B2 being applied at a rate of 1 to 50 g ha, preferably 1 to 10 g ha. Combination 4 is generally used in a ratio of A to B of 1 :5,000 to 50: 1 , preferably 1 :50 to 2: 1 , with B being applied at a rate of 1 to 500 g/ha, preferably 10 to 50 g/ha. Combination 5 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 6 is generally used in a ratio of A to B of 1 :5,000 to 5: 1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 7 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 8 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 9 is generally used in a ratio of A to B of 1 :5,000 to 5: 1, preferably 1 : 100 to 2: 1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 10 is generally used in a ratio of A to B of 1 : 10,000 to 1 :2, preferably 1 :400 to 1 :5, with B being applied at a rate of 100 to 1 ,000 g ha, preferably 100 to 400 g/ha. Combination 11 is generally used in a ratio of A to B of 1:40,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 4,000 g/ha, preferably 200 to 1,000 g/ha. Combination 12 is generally used in a ratio of A to B of 1:40,000 to 1:2, preferably 1: 1,000 to 1:10, with B being applied at a rate of 100 to 4,000 g/ha, preferably 200 to 1,000 g/ha. Combination 13 is generally used in a ratio of A to B of 1:40,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 4,000 g/ha, preferably 200 to 1,000 g/ha. Combination 14 is generally used in a ratio of A to B of 1:5,000 to 50:1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. c) (6S-C/5)- 1 -chloro-N-[2-chloro-5-(6-chlorotetrahydro- 1 ,3-dioxo- 1H- pyrrolo[ 1 ,2-c]imidazol-2(3H)-yl)-4-fluorophenyl]methanesulfonamide (mixture partner A, generally applied at a rate of 0.1 to 50 g/ha, preferably applied at a rate of 1 to 20 g/ha) in combination with: Combination 1 is generally used in a ratio of A to B of 1 : 1 ,000 to 10: 1 , preferably 1 :25 to 4: 1 , with B being applied at a rate of 5 to 100 g/ha, preferably 5 to 25 g/ha. Combination 2 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1: 10 to 10: 1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 10 g/ha. Combination 3 is generally used in a ratio of A to B 1 of 1 : 1 ,000 to 50: 1 , preferably 1 :50 to 4: 1 , and ratio of A to B2 of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1 , with B 1 being applied at a rate of 1 to 100 g/ha, preferably 5 to 50 g/ha, and B2 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 4 is generally used in a ratio of A to B of 1:5,000 to 50: 1, preferably 1:50 to 2: 1, with B being applied at a rate of 1 to 500 g/ha, preferably 10 to 50 g/ha. Combination 5 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 6 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 7 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 8 is generally used in a ratio of A to B of 1 :5,000 to 5: 1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 9 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1:100 to 2:1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 10 is generally used in a ratio of A to B of 1:10,000 to 1:2, preferably 1:400 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 400 g/ha. Combination 11 is generally used in a ratio of A to B of 1:40,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 4,000 g/ha, preferably 200 to 1,000 g ha. Combination 12 is generally used in a ratio of A to B of 1 :40,000 to 1 :2, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 100 to 4,000 g/ha, preferably 200 to 1,000 g/ha. Combination 13 is generally used in a ratio of A to B of 1 :40,000 to 1 :2, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 100 to 4,000 g/ha, preferably 200 to 1,000 g/ha. Combination 14 is generally used in a ratio of A to B of 1:5,000 to 50:1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. d) (65-cw)-N-[2-chloro-5-(6-chlorotetrahydro- 1 ,3-dioxo- 1 H-pyrrolo[ 1 ,2- c]imidazol-2(3H)-yl)-4-fluorophenyl)-N-[(chloromethyl)sulfonyl]acetamide (mixture partner A, generally applied at a rate of 0.1 to 50 g/ha, preferably applied at a rate of 1 to 20 g/ha) in combination with: Combination 1 is generally used in a ratio of A to B of 1:1,000 to 10:1, preferably 1 :25 to 4: 1 , with B being applied at a rate of 5 to 100 g/ha, preferably 5 to 25 g/ha. Combination 2 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1:10 to 10: 1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 10 g/ha. Combination 3 is generally used in a ratio of A to B 1 of 1 : 1 ,000 to 50: 1 , preferably 1 :50 to 4: 1 , and ratio of A to B2 of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1 , with B 1 being applied at a rate of 1 to 100 g/ha, preferably 5 to 50 g/ha, and B2 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 4 is generally used in a ratio of A to B of 1 :5,000 to 50: 1, preferably 1:50 to 2: 1, with B being applied at a rate of 1 to 500 g/ha, preferably 10 to 50 g/ha. Combination 5 is generally used in a ratio of A to B of 1:5,000 to 5:1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 6 is generally used in a ratio of A to B of 1:5,000 to 5:1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 7 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 8 is generally used in a ratio of A to B of 1 :5,000 to 5: 1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 gha. Combination 9 is generally used in a ratio of A to B of 1 :5,000 to 5: 1 , preferably 1 : 100 to 2: 1 , with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 10 is generally used in a ratio of A to B of 1: 10,000 to 1:2, preferably 1:400 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 400 g/ha. Combination 11 is generally used in a ratio of A to B of 1 :40,000 to 1 :2, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 100 to 4,000 g/ha, preferably 200 to 1,000 g/ha. Combination 12 is generally used in a ratio of A to B of 1:40,000 to 1:2, preferably 1: 1,000 to 1:10, with B being applied at a rate of 100 to 4,000 g/ha, preferably 200 to 1,000 g/ha. Combination 13 is generally used in a ratio of A to B of 1 :40,000 to 1:2, preferably 1: 1,000 to 1 : 10, with B being applied at a rate of 100 to 4,000 g/ha, preferably 200 to 1 ,000 g/ha. Combination 14 is generally used in a ratio of A to B of 1 :5,000 to 50: 1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. e) (6S-cw)-l-chloro-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro-l,3-dioxo-lH- pyrrolo[l,2-c]imidazol-2(3H)-yl)phenyl]methanesulfonamide monosodium salt (mixture partner A, generally applied at a rate of 0.1 to 50 g/ha, preferably applied at a rate of 1 to 20 g/ha) in combination with: Combination 1 is generally used in a ratio of A to B of 1:1,000 to 10:1, preferably 1 :25 to 4: 1, with B being applied at a rate of 5 to 100 g/ha, preferably 5 to 25 g/ha. Combination 2 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1:10 to 10: 1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 10 g/ha. Combination 3 is generally used in a ratio of A to B 1 of 1 : 1 ,000 to 50: 1 , preferably 1 :50 to 4: 1 , and ratio of A to B2 of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1 , with B 1 being applied at a rate of 1 to 100 g/ha, preferably 5 to 50 g/ha, and B2 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 4 is generally used in a ratio of A to B of 1 :5,000 to 50: 1 , preferably 1 :50 to 2: 1 , with B being applied at a rate of 1 to 500 g/ha, preferably 10 to 50 g/ha. Combination 5 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 6 is generally used in a ratio of A to B of 1 :5,000 to 5: 1 , preferably 1 :200 to 1 :2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 7 is generally used in a ratio of A to B of 1 :5,000 to 5: 1 , preferably 1 :200 to 1 :2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 8 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 9 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1: 100 to 2: 1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 10 is generally used in a ratio of A to B of 1: 10,000 to 1:2, preferably 1:400 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 400 g/ha. Combination 11 is generally used in a ratio of A to B of 1:40,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 4,000 g/ha, preferably 200 to 1,000 g/ha. Combination 12 is generally used in a ratio of A to B of 1:40,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 4,000 g/ha, preferably 200 to 1,000 g/ha. Combination 13 is generally used in a ratio of A to B of 1 :40,000 to 1 :2, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 100 to 4,000 g/ha, preferably 200 to 1,000 g/ha. Combination 14 is generally used in a ratio of A to B of 1:5,000 to 50:1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. f) (6S-cis)- 1 -chloro-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro- 1 ,3-dioxo- 1H- pyrrolof 1 ,2-c]imidazol-2(3H)-yl)phenyl]methanesulfonamide monopotassium salt (mixture partner A, generally applied at a rate of 0.1 to 50 g/ha, preferably applied at a rate of 1 to 20 g/ha) in combination with: Combination 1 is generally used in a ratio of A to B of 1: 1,000 to 10: 1, preferably 1:25 to 4: 1, with B being applied at a rate of 5 to 100 g/ha, preferably 5 to 25 g/ha. Combination 2 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1 : 10 to 10: 1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 10 g/ha. Combination 3 is generally used in a ratio of A to B l of 1: 1,000 to 50: 1, preferably 1:50 to 4: 1, and ratio of A to B2 of 1:500 to 50: 1, preferably 1: 10 to 20: 1, with B l being applied at a rate of 1 to 100 g/ha, preferably 5 to 50 g/ha, and B2 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 4 is generally used in a ratio of A to B of 1:5,000 to 50: 1, preferably 1:50 to 2: 1, with B being applied at a rate of 1 to 500 g/ha, preferably 10 to 50 g/ha. Combination 5 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 6 is generally used in a ratio of A to B of 1 :5,000 to 5:1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 7 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 8 is generally used in a ratio of A to B of 1 :5,000 to 5: 1 , preferably 1 :200 to 1 :2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 9 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1: 100 to 2: 1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 10 is generally used in a ratio of A to B of 1: 10,000 to 1:2, preferably 1:400 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 400 g/ha. Combination 11 is generally used in a ratio of A to B of 1:40,000 to 1:2, preferably 1:1,000 to 1: 10, with B being applied at a rate of 100 to 4,000 g/ha, preferably 200 to 1,000 g/ha. Combination 12 is generally used in a ratio of A to B of 1 :40,000 to 1 :2, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 100 to 4,000 g/ha, preferably 200 to 1,000 g/ha. Combination 13 is generally used in a ratio of A to B of 1 :40,000 to 1 :2, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 100 to 4,000 g/ha, preferably 200 to 1,000 g/ha. Combination 14 is generally used in a ratio of A to B of 1:5,000 to 50:1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. g) (65-cw)- l-chloro-N-[2-chloro-5-(6-chlorotetrahydro-l ,3-dioxo-lH- pyrrolo[l,2-c]imidazol-2(3H)-yl)-4-fluorophenyl]methanesulfonamide monosodium salt (mixture partner A, generally applied at a rate of 0.1 to 50 g/ha, preferably applied at a rate of 1 to 20 g/ha) in combination with: Combination 1 is generally used in a ratio of A to B of 1 : 1,000 to 10: 1, preferably 1 :25 to 4: 1 , with B being applied at a rate of 5 to 100 g/ha, preferably 5 to 25 g/ha. Combination 2 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1 : 10 to 10: 1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 10 g/ha. Combination 3 is generally used in a ratio of A to B 1 of 1 : 1 ,000 to 50: 1 , preferably 1 :50 to 4: 1, and ratio of A to B2 of 1:500 to 50:1, preferably 1: 10 to 20: 1, with Bl being applied at a rate of 1 to 100 g/ha, preferably 5 to 50 g/ha, and B2 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 4 is generally used in a ratio of A to B of 1 :5,000 to 50: 1 , preferably 1 :50 to 2: 1 , with B being applied at a rate of 1 to 500 g/ha, preferably 10 to 50 g/ha. Combination 5 is generally used in a ratio of A to B of 1:5,000 to 5:1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 6 is generally used in a ratio of A to B of 1:5,000 to 5:1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 7 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 8 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 9 is generally used in a ratio of A to B of 1 :5,000 to 5: 1 , preferably 1 : 100 to 2: 1 , with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 10 is generally used in a ratio of A to B of 1:10,000 to 1:2, preferably 1:400 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 400 g/ha. Combination 11 is generally used in a ratio of A to B of 1:40,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 4,000 g/ha, preferably 200 to 1,000 g/ha. Combination 12 is generally used in a ratio of A to B of 1:40,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 4,000 g/ha, preferably 200 to 1,000 gha. Combination 13 is generally used in a ratio of A to B of 1 :40,000 to 1 :2, preferably l 1 ,000 to 1 : 10, with B being applied at a rate of 100 to 4,000 g/ha, preferably 200 to 1,000 g/ha. Combination 14 is generally used in a ratio of A to B of 1 :5,000 to 50: 1 , preferably 1 :200 to 1 :2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. h) (65-CΛS)- 1 -chloro-N-[2-chloro-5-(6-chlorotetrahydro- 1 ,3-dioxo- 1 H- pyrrolof 1 ,2-c]imidazol-2(3H)-yl)-4-fluorophenyl]methanesulfonamide monopotassium salt (mixture partner A, generally applied at a rate of 0.1 to 50 g/ha, preferably applied at a rate of 1 to 20 g/ha) in combination with: Combination 1 is generally used in a ratio of A to B of 1 : 1 ,000 to 10: 1, preferably 1 :25 to 4: 1, with B being applied at a rate of 5 to 100 g/ha, preferably 5 to 25 g/ha. Combination 2 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1:10 to 10:1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 10 g/ha. Combination 3 is generally used in a ratio of A to B 1 of 1 : 1 ,000 to 50: 1 , preferably 1 :50 to 4: 1 , and ratio of A to B2 of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1 , with B 1 being applied at a rate of 1 to 100 g/ha, preferably 5 to 50 g/ha, and B2 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 4 is generally used in a ratio of A to B of 1 :5,000 to 50: 1 , preferably 1 :50 to 2: 1 , with B being applied at a rate of 1 to 500 g/ha, preferably 10 to 50 g/ha. Combination 5 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 6 is generally used in a ratio of A to B of 1 :5,000 to 5 : 1 , preferably 1 :200 to 1 :2, with B being applied at a rate of 10 to 500 gha, preferably 50 to 200 g/ha. Combination 7 is generally used in a ratio of A to B of 1:5,000 to 5:1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 8 is generally used in a ratio of A to B of 1:5,000 to 5:1, preferably 1:200 to 1:2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Combination 9 is generally used in a ratio of A to B of 1:5,000 to 5:1, preferably 1:100 to 2:1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 10 is generally used in a ratio of A to B of 1: 10,000 to 1:2, preferably 1:400 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 400 g/ha. Combination 11 is generally used in a ratio of A to B of 1 :40,000 to 1 :2, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 100 to 4,000 g/ha, preferably 200 to 1,000 g/ha. Combination 12 is generally used in a ratio of A to B of 1:40,000 to 1:2, preferably 1:1,000 to 1: 10, with B being applied at a rate of 163 100 to 4,000 g/ha, preferably 200 to 1,000 g/ha. Combination 13 is generally used in a ratio of A to B of 1:40,000 to 1:2, preferably 1:1,000 to 1: 10, with B being applied at a rate of 100 to 4,000 g/ha, preferably 200 to 1,000 g/ha. Combination 14 is generally used in a ratio of A to B of 1 :5,000 to 50: 1 , preferably 1 :200 to 1 :2, with B being applied at a rate of 10 to 500 g/ha, preferably 50 to 200 g/ha. Specifically preferred mixtures for use in winter wheat, winter barley, spring wheat, spring barley, and peas are selected from the group: a) (6S-cis)- 1 -chloro-N- [2-chloro-4-fluoro-5-(6-fluorotetrahydro- 1 ,3 -dioxo- 1 H- pyrrolo[l,2-c]imidazol-2(3H)-yl)phenyl]methanesulfonamide (mixture partner A, generally applied at a rate of 0.1 to 50 g/ha, preferably applied at a rate of 1 to 20 g/ha) in combination with: Combination 1 is generally used in a ratio of A to B of 1:500 to 50: 1, preferably 1 : 10 to 20: 1 , with B being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 2 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 3 is generally used in a ratio of A to B 1 of 1 :500 to 50: 1 , preferably 1 :20 to 20: 1 , and ratio of A to B2 of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1 , with B 1 being applied at a rate of 1 to 50 g/ha, preferably 1 to 20 g/ha, and B2 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 4 is generally used in a ratio of A to B of 1 :200 to 50: 1 , preferably 1 :20 to 20: 1 , with B being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 5 is generally used in a ratio of A to B 3 of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , and ratio of A to B4 of 1 :200 to 50: 1 , preferably 1:20 to 20:1, with B3 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha, and B4 being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 6 is generally used in a ratio of A to B5 of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20:1, and ratio of A to B6 of 1:500 to 50:1, preferably 1:10 to 20:1, and ratio of A to B7 of 1:200 to 50:1, preferably 1:20 to 20:1, with B5 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha, and B6 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha, and B7 being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 7 is generally used in a ratio of A to B of 1 :500 to 50: 1, preferably 1 : 10 to 20: 1, with B being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 8 is generally used in a ratio of A to B 8 of 1 :500 to 50: 1 , preferably 1:10 to 20:1, and ratio of A to B9 of 1:200 to 50:1, preferably 1:20 to 20:1, with B8 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha, and B9 being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 9 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 10 is generally used in a ratio of A to B of 1:30,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 3,000 g/ha, preferably 100 to 500 g/ha. Combination 11 is generally used in a ratio of A to B of 1 :5,000 to 5: 1 , preferably 1 : 100 to 2: 1 , with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 12 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha. Combination 13 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha. Combination 14 is generally used in a ratio of A to B10 of 1:20,000 to 1:2, preferably 1:500 to 1:5, and ratio of A to Bl 1 of 1:20,000 to 1:2, preferably 1:500 to 1:5, with B10 being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha, and B 11 being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha. Combination 15 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1:100 to 2: 1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 16 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1 : 100 to 2 : 1 , with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 17 is generally used in a ratio of A to B 12 of 1 :5,000 to 5: 1 , preferably 1 :500 to 1 :5, and ratio of A to B 13 of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20:1, with B 12 being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha, and B13 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 18 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 19 is generally used in a ratio of A to B of 1:10,000 to 1:2, preferably 1:300 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 300 g/ha. Combination 20 is generally used in a ratio of A to B 14 of 1 :2,000 to 5: 1 , preferably 1 :60 to 2: 1 , and ratio of A to B 15 of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , with B 14 being applied at a rate of 10 to 200 g/ha, preferably 10 to 60 g/ha, and B 15 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 21 is generally used in a ratio of A to B of 1:10,000 to 1:2, preferably 1:300 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 300 g/ha. Combination 22 is generally used in a ratio of A to B of 1:1,000 to 50:1, preferably 1:20 to 20:1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 23 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1 ,000 g/ha. Combination 24 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 25 is generally used in a ratio of A to B of 1 : 1 ,000 to 5 : 1 , preferably 1 :50 to 2: 1 , with B being applied at a rate of 10 to 100 g/ha, preferably 10 to 50 g/ha. Combination 26 is generally used in a ratio of A to B of 1:10,000 to 5:1, preferably 1:100 to 2:1, with B being applied at a rate of 10 to 1,000 g/ha, preferably 10 to 100 g/ha. Combination 27 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 28 is generally used in a ratio of A to B of 1 :20,000 to 1 :20, preferably 1 : 1 ,500 to 1:50, with B being applied at a rate of 1,000 to 2,000 g/ha, preferably 1,000 to 1,500 g/ha. Combination 29 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. b) (6S-cw)-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro- 1 ,3-dioxo- 1H- pyrrolo[ 1 ,2-c]imidazol-2(3H)-yl)phenyl]-N-[(chloromethyl)sulfonyl]acetamide (mixture partner A, generally applied at a rate of 0.1 to 50 g/ha, preferably applied at a rate of 1 to 20 g/ha) in combination with: Combination 1 is generally used in a ratio of A to B of 1:500 to 50:1, preferably 1 : 10 to 20: 1, with B being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 2 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 3 is generally used in a ratio of A to B 1 of 1 :500 to 50: 1 , preferably 1 :20 to 20:1, and ratio of A to B2 of 1:500 to 50:1, preferably 1:10 to 20:1, with Bl being applied at a rate of 1 to 50 g/ha, preferably 1 to 20 g/ha, and B2 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 4 is generally used in a ratio of A to B of 1 :200 to 50: 1 , preferably 1 :20 to 20: 1 , with B being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 5 is generally used in a ratio of A to B3 of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , and ratio of A to B4 of 1 :200 to 50: 1 , preferably 1:20 to 20:1, with B3 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha, and B4 being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 6 is generally used in a ratio of A to B 5 of 1 : 1 ,000 to 50: 1 , preferably 1:20 to 20:1, and ratio of A to B6 of 1:500 to 50:1, preferably 1:10 to 20:1, and ratio of A to B7 of 1:200 to 50:1, preferably 1:20 to 20:1, with B5 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha, and B6 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha, and B7 being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 7 is generally used in a ratio of A to B of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1, with B being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 8 is generally used in a ratio of A to B8 of 1:500 to 50:1, preferably 1: 10 to 20: 1 , and ratio of A to B9 of 1 :200 to 50: 1 , preferably 1 :20 to 20: 1 , with B8 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha, and B9 being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 9 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 10 is generally used in a ratio of A to B of 1:30,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 3,000 g/ha, preferably 100 to 500 g/ha. Combination 11 is generally used in a ratio of A to B of 1 :5,000 to 5: 1 , preferably 1 : 100 to 2: 1 , with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 12 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g ha. Combination 13 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha. Combination 14 is generally used in a ratio of A to B 10 of 1 :20,000 to 1 :2, preferably 1 :500 to 1 :5, and ratio of A to B 11 of 1 :20,000 to 1 :2, preferably 1:500 to 1:5, with B10 being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha, and B 11 being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha. Combination 15 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1: 100 to 2: 1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 16 is generally used in a ratio of A to B of 1 : 5,000 to 5: 1 , preferably 1 : 100 to 2: 1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 17 is generally used in a ratio of A to B 12 of 1 :5,000 to 5: 1 , preferably 1:500 to 1:5, and ratio of A to B13 of 1:1,000 to 50: 1, preferably 1:20 to 20: 1 , with B 12 being applied at a rate of 10 to 500 g/ha, preferably '10 to 100 g/ha, and B13 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 18 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 19 is generally used in a ratio of A to B of 1:10,000 to 1:2, preferably 1:300 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 300 g/ha. Combination 20 is generally used in a ratio of A to B 14 of 1 :2,000 to 5: 1 , preferably 1 :60 to 2: 1 , and ratio of A to B15 of 1:1,000 to 50:1, preferably 1:20 to 20:1, with B14 being applied at a rate of 10 to 200 g/ha, preferably 10 to 60 g/ha, and B 15 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 21 is generally used in a ratio of A to B of 1: 10,000 to 1:2, preferably 1:300 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 300 g/ha. Combination 22 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 23 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 24 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 25 is generally used in a ratio of A to B of 1 : 1 ,000 to 5: 1 , preferably 1 :50 to 2: 1 , with B being applied at a rate of 10 to 100 g/ha, preferably 10 to 50 g/ha. Combination 26 is generally used in a ratio of A to B of 1 : 10,000 to 5: 1 , preferably 1 : 100 to 2: 1 , with B being applied at a rate of 10 to 1,000 g/ha, preferably 10 to 100 g/ha. Combination 27 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1: 1,000 to 1: 10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 28 is generally used in a ratio of A to B of 1:20,000 to 1:20, preferably 1: 1,500 to 1:50, with B being applied at a rate of 1,000 to 2,000 g/ha, preferably 1,000 to 1,500 g/ha. Combination 29 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1 ,000 g/ha. c) (6S-cis)- l-chloro-N-[2-chloro-5-(6-chlorotetrahydro- 1 ,3-dioxo- 1H- pyrrolof 1 ,2-c]imidazol-2(3H)-yl)-4-fluorophenyl]methanesulfonamide (mixture partner A, generally applied at a rate of 0.1 to 50 g/ha, preferably applied at a rate of 1 to 20 g/ha) in combination with: 169 Combination 1 is generally used in a ratio of A to B of 1:500 to 50:1, preferably 1:10 to 20: 1, with B being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 2 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 3 is generally used in a ratio of A to Bl of 1:500 to 50: 1, preferably 1:20 to 20: 1 , and ratio of A to B2 of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1 , with B 1 being applied at a rate of 1 to 50 g/ha, preferably 1 to 20 g/ha, and B2 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 4 is generally used in a ratio of A to B of 1:200 to 50:1, preferably 1:20 to 20: 1, with B being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 5 is generally used in a ratio of A to B 3 of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , and ratio of A to B4 of 1 :200 to 50: 1 , preferably 1:20 to 20: 1, with B3 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha, and B4 being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 6 is generally used in a ratio of A to B 5 of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20:1, and ratio of A to B6 of 1:500 to 50:1, preferably 1:10 to 20:1, and ratio of A to B7 of 1:200 to 50:1, preferably 1:20 to 20:1, with B5 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha, and B6 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha, and B7 being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 7 is generally used in a ratio of A to B of 1:500 to 50: 1, preferably 1: 10 to 20:1, with B being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 8 is generally used in a ratio of A to B8 of 1:500 to 50: 1, preferably 1:10 to 20: 1 , and ratio of A to B9 of 1 :200 to 50: 1 , preferably 1 :20 to 20: 1 , with B8 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha, and B9 being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 9 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 10 is generally used in a ratio of A to B of 1:30,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 3,000 g/ha, preferably 100 to 500 g/ha. Combination 11 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1 : 100 to 2: 1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 12 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha. Combination 13 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha. Combination 14 is generally used in a ratio of A to B 10 of 1 :20,000 to 1 :2, preferably 1 :500 to 1 :5, and ratio of A to B 11 of 1 :20,000 to 1 :2, preferably 1:500 to 1:5, with B10 being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha, and Bl 1 being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha. Combination 15 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1:100 to 2: 1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 16 is generally used in a ratio of A to B of 1 :5,000 to 5: 1 , preferably 1:100 to 2:1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 17 is generally used in a ratio of A to B 12 of 1 :5,000 to 5: 1 , preferably 1 :500 to 1 :5, and ratio of A to B 13 of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , with B 12 being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha, and B13 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 18 is generally used in a ratio of A to B of 1 :20,000 to 1 :2, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 19 is generally used in a ratio of A to B of 1 : 10,000 to 1 :2, preferably 1 : 300 to 1 : 5 , with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 300 g/ha. Combination 20 is generally used in a ratio of A to B 14 of 1 :2,000 to 5: 1 , preferably 1 :60 to 2: 1 , and ratio of A to B 15 of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , with B 14 being applied at a rate of 10 to 200 g/ha, preferably 10 to 60 g/ha, and B 15 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 21 is generally used in a ratio of A to B of 1:10,000 to 1:2, preferably 1:300 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 300 g/ha. Combination 22 is generally used in a ratio of A to B of 1:1,000 to 50:1, preferably 1:20 to 20:1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 23 is generally used in a ratio of A to B of 1 :20,000 to 1 :2, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 24 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 25 is generally used in a ratio of A to B of 1 : 1 ,000 to 5: 1 , preferably 1 :50 to 2: 1 , with B being applied at a rate of 10 to 100 g/ha, preferably 10 to 50 g/ha. Combination 26 is generally used in a ratio of A to B of 1:10,000 to 5: 1, preferably 1:100 to 2:1, with B being applied at a rate of 10 to 1,000 g/ha, preferably 10 to 100 g/ha. Combination 27 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1 ,000 g/ha. Combination 28 is generally used in a ratio of A to B of 1:20,000 to 1:20, preferably 1:1,500 to 1:50, with B being applied at a rate of 1,000 to 2,000 g ha. preferably 1,000 to 1,500 g/ha. Combination 29 is generally used in a ratio of A to B of 1 :20,000 to 1 :2, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. d) (6S-cw)-N-[2-chloro-5-(6-chlorotetrahydro- 1 ,3-dioxo- lH-pyrrolo[ 1 ,2- c]imidazol-2(3H)-yl)-4-fluorophenyl)-N-[(chloromethyl)sulfonyl]acetamide (mixture partner A, generally applied at a rate of 0.1 to 50 g/ha, preferably applied at a rate of 1 to 20 g/ha) in combination with: 172 Combination 1 is generally used in a ratio of A to B of 1:500 to 50:1, preferably 1 : 10 to 20: 1 , with B being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 2 is generally used in a ratio of A to B of 1: 1,000 to 50: 1, preferably 1:20 to 20: 1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 3 is generally used in a ratio of A to B 1 of 1 :500 to 50: 1 , preferably 1 :20 to 20: 1 , and ratio of A to B2 of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1 , with B 1 being applied at a rate of 1 to 50 g/ha, preferably 1 to 20 g/ha, and B2 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 4 is generally used in a ratio of A to B of 1:200 to 50:1, preferably 1:20 to 20: 1, with B being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 5 is generally used in a ratio of A to B3 of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , and ratio of A to B4 of 1 :200 to 50: 1 , preferably 1:20 to 20: 1, with B3 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha, and B4 being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 6 is generally used in a ratio of A to B5 of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , and ratio of A to B6 of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1 , and ratio of A to B7 of 1:200 to 50:1, preferably 1:20 to 20:1, with B5 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha, and B6 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha, and B7 being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 7 is generally used in a ratio of A to B of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1, with B being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 8 is generally used in a ratio of A to B8 of 1 :500 to 50: 1 , preferably 1:10 to 20: 1 , and ratio of A to B9 of 1 :200 to 50: 1 , preferably 1 :20 to 20: 1 , with B8 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha, and B9 being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g ha. Combination 9 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 10 is generally used in a ratio of A to B of 1:30,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 3,000 g/ha, preferably 100 to 500 g/ha. Combination 11 is generally used in a ratio of A to B of 1:5,000 to 5:1, preferably 1:100 to 2:1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 12 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha. Combination 13 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha. Combination 14 is generally used in a ratio of A to B 10 of 1 :20,000 to 1 :2, preferably 1 :500 to 1 :5, and ratio of A to B 11 of 1 :20,000 to 1:2, preferably 1:500 to 1:5, with B10 being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha, and Bl 1 being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha. Combination 15 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1 : 100 to 2: 1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 16 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1:100 to 2:1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 17 is generally used in a ratio of A to B12 of 1:5,000 to 5: 1, preferably 1:500 to 1:5, and ratio of A to B13 of 1: 1,000 to 50: 1, preferably 1:20 to 20: 1, with B 12 being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha, and B 13 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 18 is generally used in a ratio of A to B of 1 :20,000 to 1 :2, preferably 1 : 1 ,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 19 is generally used in a ratio of A to B of 1 : 10,000 to 1 :2, preferably 1 :300 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 300 g/ha. Combination 20 is generally used in a ratio of A to B 14 of 1:2,000 to 5:1, preferably 1:60 to 2:1, and ratio of A to B 15 of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , with B 14 being applied at a rate of 10 to 200 g/ha, preferably 10 to 60 g/ha, and B15 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 21 is generally used in a ratio of A to B of 1:10,000 to 1:2, preferably 1:300 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 300 g/ha. Combination 22 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 23 is generally used in a ratio of A to B of l:20,000 to 1:2, preferably l: l,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 24 is generally used in a ratio of A to B of 1 :20,000 to 1:2, preferably 1 : 1,000 to 1 : 10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 25 is generally used in a ratio of A to B of 1 : 1 ,000 to 5: 1 , preferably 1 :50 to 2: 1 , with B being applied at a rate of 10 to 100 g/ha, preferably 10 to 50 g/ha. Combination 26 is generally used in a ratio of A to B of 1: 10,000 to 5:1, preferably 1: 100 to 2: 1, with B being applied at a rate of 10 to 1,000 g/ha, preferably 10 to 100 g/ha. Combination 27 is generally used in a ratio of A to B of 1:20,000 to 1 :2. preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 28 is generally used in a ratio of A to B of 1 :20,000 to 1 :20, preferably 1 : 1,500 to 1 :50, with B being applied at a rate of 1,000 to 2,000 g ha. preferably 1,000 to 1,500 g/ha. Combination 29 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. e) (6S-C.-?)- 1 -chloro-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro- 1 ,3-dioxo- 1H- pyrrolo[ 1 ,2-c]imidazol-2(3H)-yl)phenyl]methanesulfonamide monosodium salt (mixture partner A, generally applied at a rate of 0.1 to 50 g/ha, preferably applied at a rate of 1 to 20 g/ha) in combination with: 175 Combination 1 is generally used in a ratio of A to B of 1:500 to 50: 1, preferably 1:10 to 20:1, with B being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 2 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 3 is generally used in a ratio of A to B 1 of 1 :500 to 50: 1 , preferably 1 :20 to 20: 1 , and ratio of A to B2 of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1 , with B 1 being applied at a rate of 1 to 50 g/ha, preferably 1 to 20 gha, and B2 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 4 is generally used in a ratio of A to B of 1:200 to 50: 1, preferably 1:20 to 20: 1, with B being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 5 is generally used in a ratio of A to B3 of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , and ratio of A to B4 of 1 :200 to 50: 1 , preferably 1 :20 to 20: 1, with B3 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha, and B4 being applied at a rate of 1 to 20 g ha, preferably 1 to 10 g/ha. Combination 6 is generally used in a ratio of A to B5 of 1:1,000 to 50:1, preferably 1:20 to 20: 1, and ratio of A to B6 of 1:500 to 50:1, preferably 1:10 to 20: 1, and ratio of A to B7 of 1:200 to 50:1, preferably 1:20 to 20:1, with B5 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha, and B6 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha, and B7 being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 7 is generally used in a ratio of A to B of 1:500 to 50: 1, preferably 1 : 10 to 20: 1, with B being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 8 is generally used in a ratio of A to B8 of 1 :500 to 50: 1 , preferably 1:10 to 20:1, and ratio of A to B9 of 1:200 to 50:1, preferably 1:20 to 20:1, with B8 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha, and B9 being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 9 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 10 is generally used in a ratio of A to B of 1:30,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 3,000 g/ha, preferably 100 to 500 g/ha. Combination 11 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1:100 to 2: 1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 12 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha. Combination 13 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha. Combination 14 is generally used in a ratio of A to B 10 of 1 :20,000 to 1 :2, preferably 1 :500 to 1 :5, and ratio of A to B 11 of 1 :20,000 to 1 :2, preferably 1:500 to 1:5, with B10 being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha, and B 11 being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha. Combination 15 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1 : 100 to 2: 1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 16 is generally used in a ratio of A to B of 1:5,000 to 5:1, preferably 1:100 to 2:1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 17 is generally used in a ratio of A to B 12 of 1 :5,000 to 5: 1 , preferably 1:500 to 1:5, and ratio of A to B13 of 1 : 1,000 to 50: 1, preferably 1:20 to 20: 1 , with B 12 being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha, and B13 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 18 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 19 is generally used in a ratio of A to B of 1 : 10,000 to 1 :2, preferably 1 :300 to 1 :5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 300 g/ha. Combination 20 is generally used in a ratio of A to B 14 of 1 :2,000 to 5: 1 , preferably 1 :60 to 2: 1 , and ratio of A to B 15 of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , with B 14 being applied at a rate of 10 to 200 g/ha, preferably 10 to 60 g/ha, and B 15 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 21 is generally used in a ratio of A to B of 1: 10,000 to 1:2, preferably 1:300 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 300 g/ha. Combination 22 is generally used in a ratio of A to B of 1: 1,000 to 50:1, preferably 1:20 to 20:1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 23 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 24 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 25 is generally used in a ratio of A to B of 1 : 1 ,000 to 5: 1 , preferably 1 : 50 to 2: 1 , with B being applied at a rate of 10 to 100 g/ha, preferably 10 to 50 g/ha. Combination 26 is generally used in a ratio of A to B of 1: 10,000 to 5: 1, preferably 1:100 to 2:1, with B being applied at a rate of 10 to 1,000 g/ha, preferably 10 to 100 g/ha. Combination 27 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1: 1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 28 is generally used in a ratio of A to B of 1 :20,000 to 1 :20, preferably 1 : 1 ,500 to 1 :50, with B being applied at a rate of 1,000 to 2,000 g/ha, preferably 1,000 to 1,500 g/ha. Combination 29 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1: 1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. f) (6S-cis)- 1 -chloro-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro- 1 ,3-dioxo- 1H- pyrτolo[l,2-c]imidazol-2(3H)-yl)phenyl]methanesulfonamide monopotassium salt (mixture partner A, generally applied at a rate of 0.1 to 50 g/ha, preferably applied at a rate of 1 to 20 g/ha) in combination with: Combination 1 is generally used in a ratio of A to B of 1:500 to 50: 1, preferably 1 : 10 to 20: 1, with B being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 2 is generally used in a ratio of A to B of 1:1,000 to 50:1, preferably 1:20 to 20: 1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 3 is generally used in a ratio of A to B 1 of 1 :500 to 50: 1 , preferably 1 :20 to 20: 1 , and ratio of A to B2 of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1 , with B 1 being applied at a rate of 1 to 50 g/ha, preferably 1 to 20 g/ha, and B2 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 4 is generally used in a ratio of A to B of 1:200 to 50: 1, preferably 1:20 to 20: 1, with B being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 5 is generally used in a ratio of A to B 3 of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , and ratio of A to B4 of 1 :200 to 50: 1 , preferably 1:20 to 20: 1, with B3 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha, and B4 being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 6 is generally used in a ratio of A to B5 of 1:1,000 to 50:1, preferably 1:20 to 20: 1 , and ratio of A to B6 of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1 , and ratio of A to B7 of 1:200 to 50:1, preferably 1:20 to 20:1, with B5 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha, and B6 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha, and B7 being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 7 is generally used in a ratio of A to B of 1:500 to 50: 1, preferably 1 : 10 to 20: 1 , with B being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 8 is generally used in a ratio of A to B8 of 1 :500 to 50: 1 , preferably 1:10 to 20: 1, and ratio of A to B9 of 1:200 to 50: 1, preferably 1:20 to 20: 1, with B8 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha, and B9 being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 9 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 10 is generally used in a ratio of A to B of 1:30,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 3,000 g/ha, preferably 100 to 500 g/ha. Combination 11 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1:100 to 2: 1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 12 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha. Combination 13 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha. Combination 14 is generally used in a ratio of A to B 10 of 1 :20,000 to 1 :2, preferably 1 :500 to 1 :5, and ratio of A to B 11 of 1 :20,000 to 1 :2, preferably 1:500 to 1:5, with B10 being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha, and B 11 being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha. Combination 15 is generally used in a ratio of A to B of 1 : 5,000 to 5: 1 , preferably 1 : 100 to 2: 1 , with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 16 is generally used in a ratio of A to B of 1 : 5, 000 to 5: 1, preferably 1:100 to 2: 1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 17 is generally used in a ratio of A to B 12 of 1:5,000 to 5: 1, preferably 1 :500 to 1 :5, and ratio of A to B 13 of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1, with B12 being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha, and B13 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 18 is generally used in a ratio of A to B of 1 :20,000 to 1 :2, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 19 is generally used in a ratio of A to B of 1 : 10,000 to 1 :2, preferably 1 :300 to 1 :5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 300 g/ha. Combination 20 is generally used in a ratio of A to B 14 of 1 :2,000 to 5: 1 , preferably 1 :60 to 2: 1 , and ratio of A to B15 of 1:1,000 to 50:1, preferably 1:20 to 20:1, with B14 being applied at a rate of 10 to 200 g/ha, preferably 10 to 60 g/ha, and B 15 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 21 is generally used in a ratio of A to B of 1: 10,000 to 1:2, preferably 1:300 to 1:5, with B being applied at a rate of 100 to 1 ,000 g/ha, preferably 100 to 300 g/ha. Combination 22 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 23 is generally used in a ratio of A to B of 1 :20,000 to 1 :2, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 24 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1: 1,000 to 1: 10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 25 is generally used in a ratio of A to B of 1:1,000 to 5:1, preferably 1:50 to 2:1, with B being applied at a rate of 10 to 100 g/ha, preferably 10 to 50 g/ha. Combination 26 is generally used in a ratio of A to B of 1:10,000 to 5:1, preferably 1:100 to 2:1, with B being applied at a rate of 10 to 1,000 g/ha, preferably 10 to 100 g/ha. Combination 27 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1: 1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 28 is generally used in a ratio of A to B of 1 :20,000 to 1 :20, preferably 1 : 1 ,500 to 1 :50, with B being applied at a rate of 1,000 to 2,000 g/ha, preferably 1,000 to 1,500 g/ha. Combination 29 is generally used in a ratio of A to B of 1 :20,000 to 1 :2, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. g) (65-cw)- 1 -chloro-N-[2-chloro-5-(6-chlorotetrahydro- 1 ,3-dioxo- 1H- pyrrolo[ 1 ,2-c]imidazol-2(3H)-yl)-4-fluorophenyl]methanesulfonamide monosodium salt (mixture partner A, generally applied at a rate of 0.1 to 50 g/ha, preferably applied at a rate of 1 to 20 g/ha) in combination with: Combination 1 is generally used in a ratio of A to B of 1:500 to 50: 1, preferably 1 : 10 to 20: 1, with B being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 2 is generally used in a ratio of A to B of 1:1,000 to 50:1, preferably 1:20 to 20: 1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 3 is generally used in a ratio of A to Bl of 1:500 to 50:1, preferably 1:20 to 20: 1 , and ratio of A to B2 of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1 , with B 1 being applied at a rate of 1 to 50 g/ha, preferably 1 to 20 g/ha, and B2 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 gha. Combination 4 is generally used in a ratio of A to B of 1:200 to 50: 1, preferably 1:20 to 20: 1, with B being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 5 is generally used in a ratio of A to B 3 of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , and ratio of A to B4 of 1 :200 to 50: 1 , preferably 1:20 to 20:1, with B3 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha, and B4 being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 6 is generally used in a ratio of A to B 5 of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20:1, and ratio of A to B6 of 1:500 to 50: 1, preferably 1:10 to 20: 1, and ratio of A to B7 of 1 :200 to 50: 1 , preferably 1 :20 to 20: 1 , with B5 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha, and B6 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha, and B7 being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 7 is generally used in a ratio of A to B of 1 :500 to 50: 1 , preferably 1 : 10 to 20: 1, with B being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 8 is generally used in a ratio of A to B8 of 1 :500 to 50: 1 , preferably 1:10 to 20: 1 , and ratio of A to B9 of 1 :200 to 50: 1 , preferably 1 :20 to 20: 1 , with B8 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha, and B9 being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 9 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 10 is generally used in a ratio of A to B of 1:30,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 3,000 g/ha, preferably 100 to 500 g/ha. Combination 11 is generally used in a ratio of A to B of 1:5,000 to 5:1, preferably 1:100 to 2:1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 12 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha. Combination 13 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha. Combination 14 is generally used in a ratio of A to B 10 of 1 :20,000 to 1 :2, preferably 1 :500 to 1 :5, and ratio of A to B 11 of 1 :20,000 to 1 :2, preferably 1:500 to 1:5, with B10 being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha, and Bl 1 being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha. Combination 15 is generally used in a ratio of A to B of 1:5,000 to 5: 1 , preferably 1:100 to 2: 1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 16 is generally used in a ratio of A to B of 1 : 5 ,000 to 5 : 1 , preferably 1 : 100 to 2: 1 , with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 17 is generally used in a ratio of A to B 12 of 1:5,000 to 5: 1, preferably 1:500 to 1:5, and ratio of A to B 13 of 1:1,000 to 50:1, preferably 1:20 to 20: 1 , with B 12 being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha, and B13 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 18 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 19 is generally used in a ratio of A to B of 1 : 10,000 to 1 :2, preferably 1 :300 to 1 :5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 300 g/ha. Combination 20 is generally used in a ratio of A to B 14 of 1 :2,000 to 5: 1 , preferably 1 :60 to 2: 1 , and ratio of A to B 15 of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , with B 14 being applied at a rate of 10 to 200 g/ha, preferably 10 to 60 g/ha, and B 15 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 21 is generally used in a ratio of A to B of 1:10,000 to 1:2, preferably 1:300 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 300 g/ha. Combination 22 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 23 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1: 1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 24 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 25 is generally used in a ratio of A to B of 1 : 1 ,000 to 5: 1, preferably 1:50 to 2:1, with B being applied at a rate of 10 to 100 g/ha, preferably 10 to 50 g/ha. Combination 26 is generally used in a ratio of A to B of 1 : 10,000 to 5: 1 , preferably 1: 100 to 2: 1, with B being applied at a rate of 10 to 1,000 g/ha, preferably 10 to 100 g/ha. Combination 27 is generally used in a ratio of A to B of 1:20,000 to 1 :2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 28 is generally used in a ratio of A to B of 1 :20,000 to 1 :20, preferably 1 : 1 ,500 to 1 :50, with B being applied at a rate of 1,000 to 2,000 g/ha, preferably 1,000 to 1,500 g/ha. Combination 29 is generally used in a ratio of A to B of 1 :20,000 to 1:2, preferably 1: 1,000 to 1 : 10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. h) (6S-cis)- 1 -chloro-N-[2-chloro-5-(6-chlorotetrahydro- 1 ,3-dioxo- 1H- pyrrolof 1 ,2-c]imidazol-2(3H)-yl)-4-fluorophenyl]methanesulfonamide monopotassium salt (mixture partner A, generally applied at a rate of 0.1 to 50 g/ha, preferably applied at a rate of 1 to 20 g/ha) in combination with: Combination 1 is generally used in a ratio of A to B of 1:500 to 50:1, preferably 1 : 10 to 20: 1 , with B being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 2 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20:1, with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 3 is generally used in a ratio of A to Bl of 1:500 to 50: 1, preferably 1:20 to 20: 1, and ratio of A to B2 of 1:500 to 50:1, preferably 1: 10 to 20:1, with B l being applied at a rate of 1 to 50 g/ha, preferably 1 to 20 g/ha, and B2 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 4 is generally used in a ratio of A to B of 1:200 to 50:1, preferably 1:20 to 20:1, with B being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 5 is generally used in a ratio of A to B3 of 1 : 1 ,000 to 50: 1 , preferably 1 : 20 to 20: 1 , and ratio of A to B4 of 1 : 200 to 50: 1 , preferably 1:20 to 20: 1, with B3 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha, and B4 being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 6 is generally used in a ratio of A to B 5 of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20:1, and ratio of A to B6 of 1:500 to 50:1, preferably 1:10 to 20: 1, and ratio of A to B7 of 1:200 to 50:1, preferably 1:20 to 20:1, with B5 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha, and B6 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha, and B7 being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 7 is generally used in a ratio of A to B of 1:500 to 50:1, preferably 1:10 to 20: 1 , with B being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha. Combination 8 is generally used in a ratio of A to B8 of 1 :500 to 50: 1 , preferably 1: 10 to 20: 1 , and ratio of A to B9 of 1 :200 to 50: 1 , preferably 1 :20 to 20: 1 , with B8 being applied at a rate of 1 to 50 g/ha, preferably 1 to 10 g/ha, and B9 being applied at a rate of 1 to 20 g/ha, preferably 1 to 10 g/ha. Combination 9 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 10 is generally used in a ratio of A to B of 1:30,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 3,000 g/ha, preferably 100 to 500 g/ha. Combination 11 is generally used in a ratio of A to B of 1:5,000 to 5:1, preferably 1:100 to 2:1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 12 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha. Combination 13 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:500 to 1:5, with B being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha. Combination 14 is generally used in a ratio of A to B 10 of 1:20,000 to 1:2, preferably 1:500 to 1:5, and ratio of A to Bl l of 1:20,000 to 1:2, preferably 1:500 to 1:5, with B10 being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha, and Bl 1 being applied at a rate of 100 to 2,000 g/ha, preferably 100 to 500 g/ha. Combination 15 is generally used in a ratio of A to B of 1:5,000 to 5: 1, preferably 1 : 100 to 2: 1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 16 is generally used in a ratio of A to B of 1 : 5,000 to 5: 1 , preferably 1:100 to 2:1, with B being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha. Combination 17 is generally used in a ratio of A to B 12 of 1:5,000 to 5: 1, preferably 1 :500 to 1 :5, and ratio of A to B 13 of 1 : 1 ,000 to 50: 1 , preferably 1 :20 to 20: 1 , with B 12 being applied at a rate of 10 to 500 g/ha, preferably 10 to 100 g/ha, and B13 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 18 is generally used in a ratio of A to B of 1 :20,000 to 1 :2, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 19 is generally used in a ratio of A to B of 1 : 10,000 to 1 :2, preferably 1 :300 to 1 :5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 300 g/ha. Combination 20 is generally used in a ratio of A to B 14 of 1 :2,000 to 5: 1 , preferably 1 :60 to 2: 1 , and ratio of A to B15 of 1: 1,000 to 50: 1, preferably 1:20 to 20: 1, with B14 being applied at a rate of 10 to 200 g/ha, preferably 10 to 60 g/ha, and B15 being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 21 is generally used in a ratio of A to B of 1: 10,000 to 1:2, preferably 1:300 to 1:5, with B being applied at a rate of 100 to 1,000 g/ha, preferably 100 to 300 g/ha. Combination 22 is generally used in a ratio of A to B of 1 : 1 ,000 to 50: 1 , preferably 1 : 20 to 20: 1 , with B being applied at a rate of 1 to 100 g/ha, preferably 1 to 20 g/ha. Combination 23 is generally used in a ratio of A to B of 1 :20,000 to 1 :2, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 24 is generally used in a ratio of A to B of 1 :20,000 to 1:2, preferably 1: 1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 25 is generally used in a ratio of A to B of 1 : 1 ,000 to 5: 1 , preferably 1 :50 to 2: 1 , with B being applied at a rate of 10 to 100 g/ha, preferably 10 to 50 g/ha. Combination 26 is generally used in a ratio of A to B of 1:10,000 to 5:1, preferably 1:100 to 2:1, with B being applied at a rate of 10 to 1,000 g/ha, preferably 10 to 100 g/ha. Combination 27 is generally used in a ratio of A to B of 1:20,000 to 1:2, preferably 1:1,000 to 1:10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. Combination 28 is generally used in a ratio of A to B of 1 :20.000 to 1 :20, preferably 1 : 1 ,500 to 1:50, with B being applied at a rate of 1,000 to 2,000 g/ha, preferably 1,000 to 1,500 g/ha. Combination 29 is generally used in a ratio of A to B of 1 :20,000 to 1 :2, preferably 1 : 1 ,000 to 1 : 10, with B being applied at a rate of 100 to 2,000 g/ha, preferably 200 to 1,000 g/ha. 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 0.001 to 20 kg/ha with a preferred range of 0.001 to 1.0 kg/ha. One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control. 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-K for compound descriptions. The following abbreviation is used in the Index Tables which follow: CN = cyano. The abbreviation "dec" indicates that the compound appeared to decompose on melting. The abbreviation "Ex." stands for "Example" and is followed by a number indicating in which example the compound is prepared. Index Table A Index Table C CH 2 CsCH H S0 2 CH 2 C1 C(0)CH 3 S0 2 CH 2 C1 H H S0 2 CH 2 C1 Index Table F 58 Cl CQ 2 CH 3 Cl C(0)CH 3 115-118 Index Table J Cmpd Structure m.p. (°C) *See Index Table K for J H NMR data. Index Table K Cmpd No. J H NMR Data (CDC1 3 solution unless indicated otherwise) 3 2 δ 7.56 (d, IH), 7.40 (d, IH), 4.68 (m, IH), 4.66 (s, 2H), 4.29 (m, IH), 2.44 (m, 4H), 1.84 (m, 4H). 15 δ 7.83 (s, IH), 7.54 (s, IH), 6.96 (s, IH), 3.70 ( , 2H), 3.31 (quintet, IH), 2.78 (t, 2H), 2.01 (m, 4H), 1.39 (d, 6H). 18 (DMSO-d 6 ) δ 10.05 (s, IH), 7.92 (d, IH), 7.47 (d, IH), 6.96 (ddd, IH), 6.05 (dd, 2H), 3.57 (t, 2H), 2.68 (t, 2H), 1.78-1.99 (m, 4H). 19 (DMSO-d 6 ) δ 8.14 (s, IH), 7.68 (s, IH), 7.25 (dd, 2H), 6.45 (dd, 2H), 6.35 (dd, 2H), 3.56 (m, 2H), 2.69 (t, 2H), 1.89 (m, 2H), 1.81 (m, 2H). 20 δ 7.9-7.7 (m, 2H), 5.7-5.5 (m, IH), 4.7 (dd, IH), 4.5 (s, 2H), 3.4 (s, IH), 3.5-3.3 (m, 2H). 2.5-2.1 (m, 2H). 21 δ 7.62 (d, IH), 7.34 (d, IH), 7.26 (br s, IH), 5.5 (m, IH), 4.60 (dd, IH), 4.52 (s, 2H), 4.12 (m, IH), 3.62 (dd, IH), 2.64 (m, IH), 2.06 (m, IH). 24 δ 7.78 (d, IH), 7.42 (d, IH), 5.31 (dd, 2H), 4.90 (dd, 2H), 4.79 (m, 2H), 4.22 (dd, IH), 3.62 (dd, IH), 2.60 ( , IH), 2.32 (m, IH). 48 δ 7.70 (d, IH), 7.38 (d, IH), 7.08 (br s, IH), 4.56 (br s, 3H), 4.42 (dd, IH), 4.30 (d, IH), 3.52 (dd, IH), 2.36 (m, 2H). 54 δ 8.42 (d, IH), 7.18 (d, IH), 6.96 (br s, IH), 5.32 (m, IH), 4.58 (s, 2H), 4.22 (q, 2H), 4.06 (m, 3H), 2.46 (m, 2H). 55 δ 8.42 (d, IH), 7.21 (d, IH), 7.0 (br s, IH), 4.64 (t, IH), 4.60 (s, 2H), 4.58 (m, IH), 4.24 (q, 2H), 3.92 (m, 2H), 2.60 (m, 2H). 69 δ 7.65 (d, IH), 7.35 (d, IH), 4.70 (br s, IH), 4.55 (s, 3H), 4.10-4.00 (m, IH), 3.5-3.35 (m, IH), 2.6-2.5 (br d, IH), 2.1 (m, 3H). 73 (DMSO-d 6 ) δ l0.1 (br s, IH), 7.75 (m, lH), 7.4 (dd. lH), 5.1 ( , IH), 4.9 (s, 2H), 4.1-3.9 (m, 3H), 3.75 (m, IH), 2.95 (m, IH), 2.05 (m, IH), 1.9 (br d, IH), 1.2 (m, IH). a *H NMR data are in ppm downfield from tetramethylsilane. Couplings are designated by (s)-singlet, (d)-doublet, (t)-triplet, (q)-quartet, (m)-multiplet, (dd)-doublet of doublets, (ddd)-doublet of doublet of doublets, (dt)-doublet of triplets, (br s)-broad singlet. BIOLOGICAL EXAMPLES OF THE INVENTION TEST A Seeds of barnyardgrass (Echinochloa crus-gallϊ), cocklebur (Xanthium strumarium), crabgrass (Digitaria spp.), downy brome (Bromus tectorum), giant foxtail (Setariafaberii), morningglory (Ipomoea spp.), sorghum (Sorghum bicolor), velvetleaf (Abutilon theophrasti), and wild oat (Avenafatua) were planted into a sandy loam soil and treated preemergence by soil drench (PDRN), with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. At the same time, these crop and weed species were also treated postemergence sprayed to runoff (STRO), with test chemicals formulated in the samO manner. Plants ranged in height from two to eighteen cm and were in the two to three leaf stage for the postemergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately eleven days, after which 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 10 scale where 0 is no effect and 10 is complete control. A dash (-) response means no test results. Table A COMPOUND Table A COMPOUND Rate 2000 g/ha 45 50 59 68 Rate 1000 g/ha 45 50 59 68 PDRN STRO Barnyardgrass 10 10 10 9 Barnyardgrass 10 10 10 8 Cocklebur 10 10 10 10 Cocklebur 10 10 10 10 Crabgrass 10 9 10 8 Crabgrass 6 8 9 3 Downy brome 7 8 9 2 Downy brome 4 10 8 3 Giant foxtail 10 10 10 9 Giant foxtail 7 7 9 3 Morningglory 10 10 10 10 Morningglory 10 10 10 10 Sorghum 5 3 10 0 Sorghum 6 5 7 3 Velvetleaf 10 10 10 10 Velvetleaf 10 10 10 10 Wild oats 9 9 9 9 Wild oats 5 9 5 2 TEST B Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloa crus-galli), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), cocklebur (Xanthium strumarium), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria sanguinalis), downy brome (Bromus tectorum), giant foxtail (Setariafaberii), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), rape (Brassica napus), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), wild oat (Avenafatua) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from two to eighteen cm (one to four leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for twelve to sixteen days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table B, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result. Table B COMPOUND Rate 200 g/ha 1 2 11 15 16 17 18 19 20 21 31 32 33 34 35 36 37 47 53 58 61 62 63 65 POSTEMERGENCE Barley 2 5 3 4 4 4 1 0 4 3 3 3 4 5 4 3 5 4 3 3 3 1 1 3 Barnyardgrass 7 6 9 4 2 6 3 4 9 10 1 10 5 10 5 7 10 4 10 9 9 2 1 8 Bedstraw 6 9 8 7 5 7 6 3 9 9 10 10 9 10 10 10 10 3 9 10 - 10 - 9 Blackgrass 3 3 2 3 5 5 1 0 5 6 3 3 4 6 5 4 7 3 3 2 2 4 1 3 Chickweed 7 8 8 2 3 7 0 0 9 10 9 10 10 10 10 10 10 5 10 10 4 3 2 5 Cocklebur 9 10 10 10 7 9 7 6 10 10 10 10 10 10 10 10 10 10 10 10 10 10 5 10 Corn 3 3 9 3 3 7 2 2 3 9 2 7 3 8 3 3 6 3 4 2 6 6 1 5 Cotton 10 10 10 9 10 10 3 8 10 10 10 10 10 10 10 10 10 10 10 10 10 9 7 10 Crabgrass 2 6 7 3 6 4 3 5 3 7 4 4 3 8 3 3 2 2 1 2 4 2 1 2 Downy brome 2 3 2 3 4 4 0 0 4 4 3 2 3 5 4 3 5 3 3 2 2 1 0 3 Giant foxtail 2 6 7 5 6 6 6 5 7 8 3 3 4 6 4 3 8 2 2 2 4 2 1 3 Lambsquarter 7 10 10 9 10 9 6 7 10 10 10 10 10 10 10 10 10 9 10 10 9 6 2 10 Morningglory 7 10 10 10 10 10 7 6 10 10 10 10 10 10 10 10 10 10 10 10 10 10 4 10 Nutsedge 2 2 2 5 2 6 0 0 1 3 3 2 3 4 5 5 3 - 1 1 8 2 0 2 Rape 5 10 10 3 9 9 4 3 10 10 10 10 10 10 10 10 10 10 10 10 10 10 2 10 Rice 4 6 5 4 5 5 3 4 6 6 6 3 4 9 6 4 6 2 2 3 4 3 2 4 Sorghum 3 4 4 3 3 3 4 4 5 3 3 - - 8 7 2 2 2 2 2 3 2 1 7 Soybean 8 9 5 6 8 8 2 3 9 6 9 6 10 10 9 10 10 3 2 3 9 3 2 3 Sugar beet 9 10 10 10 9 10 4 4 10 10 10 10 10 10 10 10 10 10 10 10 10 7 3 10 Velvetleaf 10 10 10 10 10 10 6 7 10 10 10 10 10 10 10 10 10 10 10 10 10 8 4 10 Wheat 3 3 4 3 6 6 0 2 3 5 4 3 4 4 4 3 5 3 2 2 4 2 2 3 Wild buckwheat 9 10 10 9 10 10 2 3 10 10 10 10 10 10 10 10 10 10 10 10 10 1 1 10 Wild oat 1 2 3 2 3 3 0 0 4 3 3 3 3 4 3 4 7 2 3 3 1 2 1 5 Table B COMPOUND Rate 200 g/ha 1 2 11 15 16 17 18 19 20 21 31 32 33 34 35 36 37 47 53 58 61 62 63 65 PREEMERGENCE Barley 0 0 0 0 0 0 0 0 5 4 0 0 0 3 3 0 0 0 0 0 0 0 0 1 Barnyardgrass 0 4 3 3 3 4 0 0 6 7 2 3 10 10 6 5 10 0 0 0 8 0 0 1 Bedstraw 2 9 0 0 0 3 0 0 10 10 10 10 10 10 10 10 10 7 10 10 10 2 - - Blackgrass 0 1 0 0 0 0 2 0 4 3 1 5 2 9 4 1 6 0 1 0 2 0 0 0 Chickweed 0 2 2 0 0 5 0 0 9 9 10 10 10 10 10 10 10 9 9 10 10 9 0 - Cocklebur 0 3 0 0 0 0 0 0 10 10 9 10 8 10 10 10 10 1 10 10 10 0 10 10 Corn 0 0 2 0 2 0 0 0 0 2 1 0 3 4 3 2 1 0 0 0 0 0 0 0 Cotton 5 4 0 0 10 5 0 - 10 10 10 10 7 10 10 10 10 0 10 0 10 0 0 8 Crabgrass 0 6 0 2 8 3 0 0 9 5 9 2 10 10 8 2 6 2 0 0 0 0 0 0 Downy brome 0 1 0 0 0 0 2 3 3 3 3 3 2 8 5 3 5 0 0 0 0 0 0 2 Giant foxtail 1 3 0 0 2 2 0 0 9 2 4 0 8 10 6 3 7 0 0 0 0 0 0 0 Lambsquarter 10 10 10 9 10 10 10 7 10 10 10 10 10 10 10 10 10 10 10 10 10 10 - - Morningglory - 4 3 0 0 0 0 0 10 10 10 10 10 10 10 10 10 10 10 10 10 0 0 10 f Nutsedge - 8 5 0 0 0 0 0 1 0 0 0 3 4 4 10 0 - 0 0 10 0 6 1 o Rape 8 0 6 0 0 6 4 5 9 10 8 10 7 9 9 10 10 9 10 10 10 6 1 - Rice 0 3 3 0 4 3 0 0 3 1 4 1 4 9 5 2 4 0 0 0 0 0 0 0 Sorghum 0 0 0 0 0 0 0 0 2 0 0 0 3 8 2 0 1 0 0 0 0 0 0 0 Soybean 0 3 0 0 6 2 0 0 3 3 10 0 9 9 10 10 10 0 0 0 0 0 0 0 Sugar beet 9 9 10 3 0 9 6 5 10 10 10 10 10 10 10 10 10 10 10 10 10 7 2 - Velvetleaf 10 7 10 6 0 10 0 0 10 10 10 10 10 10 10 10 10 9 10 10 10 7 9 10 Wheat 0 0 0 0 0 0 0 0 3 3 0 0 3 5 6 2 3 0 2 0 0 0 0 0 Wild buckwheat 2 0 0 0 0 7 0 0 10 5 9 10 8 10 10 10 10 0 10 10 10 3 - - Wild oat 0 2 0 0 0 0 2 0 4 3 4 0 5 8 7 6 8 0 3 0 0 0 0 1 O 97/15576 201 Table B COMPOUND Rate 50 g/ha 47 48 50 51 53 58 59 61 62 63 65 6* POSTEMERGENCE Table B COMPOUND Rate 50 g/ha 47 48 50 51 53 58 59 61 62 63 65 6f PREEMERGENCE Table B COMPOUND Rate 20 g/ha 39 40 41 42 43 44 72 POSTEMERGENCE Barley 3 3 2 2 3 3 2 Barnyardgrass 10 10 10 10 8 10 1 Bedstraw 9 10 9 10 9 9 8 Blackgrass 2 1 2 1 2 2 1 Chickweed 10 10 10 10 9 10 2 Cocklebur 10 10 10 10 10 10 7 Corn 1 3 2 2 2 2 1 Cotton 10 10 10 10 10 10 10 Crabgrass 2 2 2 2 2 2 4 Downy brome 2 2 2 2 2 3 1 Giant foxtail 2 2 3 2 3 4 1 Lambsquarter 9 10 10 10 10 10 8 Morningglory 10 10 10 10 10 10 6 Nutsedge 1 - 1 1 1 2 1 Rape 10 10 10 10 10 10 2 Rice 2 2 2 2 2 3 3 Sorghum 2 2 3 2 2 2 - Soybean 2 3 2 3 3 3 3 Sugar beet 10 10 10 10 10 10 3 Velvetleaf 10 10 10 10 10 10 3 Wheat 2 3 3 3 4 3 1 Wild buckwheat 10 10 10 10 10 10 7 Wild oat 2 2 2 2 3 2 1 O 971 209 TEST C The compounds evaluated in this test were formulated in a non-phytoxic solvent mixture which included a surfactant and applied to the soil surface before plant seedlings emerged (preemergence application), to water that covered the soil surface (flood application), and to plants that were in the one-to-four leaf stage (postemergence application). A sandy loam soil was used for the preemergence and postemergence tests, while a silt loam soil was used in the flood test. Water depth was approximately 2.5 cm for the flood test and was maintained at this level for the duration of the test. Plant species in the preemergence and postemergence tests consisted of barnyardgrass (Echinochloa crus-galli), barley (Hordeum vulgare), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), cocklebur (Xanthium strumarium), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria sanguinalis), downy brome (Bromus tectorum), of barnyardgrass (Echinochloa crus-galli), barley (Hordeum vulgare), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), cocklebur (Xanthium strumarium), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria sanguinalis), downy brome (Bromus tectorum), giant foxtail (Setaria faberii), johnsongrass (Sorghum halpense), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), pigweed (Amaranthus retroflexus), rape (Brassica napus), ryegrass (Lolium multiflorum), soybean (Glycine max), speedwell (Veronica persica), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrastϊ), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avenafatua). All plant species were planted one day before application of the compound for the preemergence portion of this test. Plantings of these species were adjusted to produce plants of appropriate size for the postemergence portion of the test. Plant species in the flood test consisted of rice (Oryza sativa), umbrella sedge (Cyperus difformis), duck salad (Heteranthera limosa), barnyardgrass (Echinochloa crus-galli) and Late watergrass (Echinocloa oryzicola) grown to the 2 leaf stage for testing. All plant species were grown using normal greenhouse practices. Visual evaluations of injury expressed on treated plants, when compared to untreated controls, were recorded approximately fourteen to twenty one days after application of the test compound. Plant response this ratings, summarized in Table C, were recorded on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Table C COMPOUND Rate 62 g/ha 1 2 3 4 5 7 8 9 10 11 12 13 14 20 21 45 65 70 POSTEMERGENCE Barley Igri 35 35 35 25 30 0 20 20 30 30 40 45 45 40 35 0 30 10 Barnyard 2 20 30 25 20 15 0 0 20 40 30 10 65 0 20 35 - 0 - Barnyardgrass 60 30 35 40 50 15 10 10 0 85 60 35 50 75 100 70 50 60 Bedstraw 100 100 - 100 100 50 70 100 70 50 45 40 55 100 100 100 80 100 Blackgrass 10 35 15 25 20 10 40 20 10 15 20 30 25 10 10 70 20 70 Chickweed 100 80 10 35 90 - - 100 100 80 30 85 55 100 100 100 40 100 Cocklebur 100 90 90 100 100 100 90 100 100 100 50 60 70 100 100 100 100 100 Corn 30 15 25 35 35 15 20 20 15 50 80 35 50 35 55 10 10 40 Cotton 100 100 100 100 100 100 100 100 100 100 100 90 - 100 100 100 100 100 NJ Crabgrass 35 50 40 30 50 30 20 15 20 30 35 35 50 35 50 30 20 50 Downy Brome 30 30 20 30 10 0 30 0 0 0 20 30 25 20 0 20 0 35 Duck salad 0 0 0 0 0 0 0 40 10 0 0 0 0 0 0 - 0 - Giant foxtail 40 60 35 60 50 20 15 25 20 35 55 45 35 55 75 40 20 60 Italn. Rygrass 35 10 20 25 20 0 0 30 10 0 0 10 20 30 0 20 30 10 Johnsongrass - 30 60 60 50 20 0 25 20 60 50 50 60 40 55 35 50 65 Lambsquarter 100 100 - 100 90 70 100 80 60 100 100 100 100 100 100 100 80 100 Morningglory 90 100 90 85 90 100 100 100 100 100 70 85 50 100 100 100 100 100 Rape 90 100 65 50 80 80 30 70 60 100 90 100 100 100 100 100 100 100 Redroot Pigweed 100 100 90 100 95 70 50 30 50 100 100 100 100 100 100 100 100 100 Rice Japonica - 35 35 25 25 0 0 20 0 30 0 45 15 35 20 - 0 Soybean 50 70 40 70 60 40 30 35 35 30 35 70 40 80 40 20 50 50 Speedwell 100 90 100 - 90 100 60 70 85 - 100 100 100 100 100 100 Sugar beet 100 100 - 100 100 - - 80 70 100 100 100 100 100 100 Umbrella sedge 0 0 0 0 0 0 0 0 0 0 0 25 0 0 0 - 0 - Velvetleaf 100 100 100 100 100 100 90 100 90 100 100 100 100 100 100 100 100 100 Watergrass 2 15 30 15 15 15 - - - - 20 10 65 0 25 20 - - - Wheat 35 25 30 25 30 0 10 20 20 20 35 40 40 30 25 0 0 10 Wild buckwheat 100 95 100 100 100 70 85 90 70 85 100 95 100 100 100 100 100 100 Wild oat 30 35 35 25 25 10 40 20 40 10 35 45 40 35 30 0 30 20 π Table C COMPOUND Rate 31 g/ha 1 2 3 4 5 7 8 9 10 11 12 13 14 20 21 23 25 26 27 28 29 30 POSTEMERGENCE Barley Igri 30 35 35 25 30 0 10 10 20 30 25 40 35 40 35 30 40 20 20 10 0 25 Barnyard 2 20 30 20 20 15 0 0 0 10 25 0 50 0 15 25 20 0 20 15 10 10 10 Barnyardgrass 50 30 30 35 40 10 10 0 0 75 50 30 40 50 90 100 100 85 70 60 60 100 Bedstraw 80 100 100 50 100 40 70 50 35 - 45 40 45 100 100 100 100 90 90 45 45 70 Blackgrass 0 30 10 20 20 10 30 0 10 15 10 30 25 10 10 25 50 20 15 15 15 15 Chickweed 80 80 10 35 65 - - 90 75 70 30 30 55 100 100 100 100 70 50 40 0 90 Cocklebur 90 90 90 90 95 100 80 70 80 90 35 50 40 100 100 100 100 80 80 70 60 100 Corn 20 15 20 30 30 10 15 15 10 35 30 35 40 25 40 20 30 35 25 20 10 30 Cotton 100 100 100 100 100 100 100 100 90 100 95 90 90 100 100 100 100 100 100 90 90 100 Sugar beet 100 100 100 100 100 - - 60 60 100 100 100 100 100 100 100 100 100 100 90 80 100 Umbrella sedge 0 0 0 0 0 0 0 0 0 0 0 20 0 0 0 0 0 0 20 0 0 0 Velvetleaf 100 100 100 100 100 90 90 30 80 100 100 100 100 100 100 100 100 100 100 85 60 100 Watergrass 2 10 30 15 15 15 - - - - 10 0 50 0 20 20 35 - 25 10 10 0 10 Wheat 30 20 30 25 30 0 0 10 10 15 20 40 30 20 20 30 35 20 15 10 10 20 Wild buckwheat 85 80 100 - 100 70 40 90 60 85 95 95 95 100 100 100 100 100 95 70 65 100 Wild oat 30 35 35 25 25 0 35 0 30 10 35 45 35 35 30 25 25 15 15 10 0 25 NJ Table C COMPOUND Rate 31 g/ha 36 37 45 46 49 52 53 54 56 57 60 64 65 68 69 70 73 POSTEMERGENCE Barley Igri 20 20 0 20 30 30 35 30 25 30 20 20 20 0 30 20 0 Barnyard 2 - - - 10 - 10 0 0 0 0 - 0 0 0 0 - 0 Barnyardgrass 20 80 60 55 95 100 100 100 55 90 55 60 40 10 80 80 0 Bedstraw 100 100 100 50 50 90 85 85 100 100 50 95 70 0 100 100 Blackgrass 25 30 50 0 25 25 20 25 15 25 10 10 10 0 10 40 0 Chickweed 100 100 - 10 95 100 100 95 60 60 100 95 - 0 95 - 0 Cocklebur 100 100 100 70 100 100 100 100 80 100 100 100 100 40 100 100 20 Corn 10 10 10 20 35 30 30 20 20 75 10 15 10 10 20 60 5 Cotton 100 100 100 100 100 100 100 100 80 100 100 100 100 80 100 100 10 ■ NJ Crabgrass 10 20 20 30 30 30 50 50 60 60 20 30 15 10 30 50 0 00 Downy Brome 10 20 10 0 10 25 10 0 20 70 10 25 0 0 25 20 0 Duck salad - - - 0 - 0 0 0 0 0 - 0 0 0 0 - 0 Giant foxtail 15 25 30 20 25 35 40 50 60 70 20 20 15 0 30 75 0 Italn. Rygrass 20 20 15 0 10 20 0 0 20 40 10 20 10 0 25 30 0 Johnsongrass 10 20 25 30 50 25 50 40 50 90 10 20 40 10 50 50 10 Lambsquarter 95 100 100 70 85 100 100 100 70 100 90 95 70 85 65 80 10 Morningglory 100 100 100 100 85 100 100 100 80 100 100 100 100 35 100 100 30 Rape 100 100 100 90 95 100 100 100 95 100 100 100 100 0 100 100 0 Redroot Pigweed 100 100 100 100 90 100 90 100 90 100 100 95 80 60 90 90 15 Rice Japonica - - - 20 - 0 0 0 0 0 - 0 0 10 0 - 0 Soybean 80 60 20 40 25 50 35 50 40 - 20 40 40 30 60 60 30 Speedwell 100 100 100 100 100 100 100 100 90 100 100 95 100 0 100 100 0 Sugar beet 90 100 - 100 100 100 100 100 40 25 100 100 - 65 100 - 0 Umbrella sedge - - - 0 - 0 0 0 0 0 - 0 0 0 0 - 0 Velvetleaf 100 100 100 100 100 100 100 100 90 100 100 100 100 100 100 100 20 Watergrass 2 _ _ _ ιo - - - - - - - - - - - - - Wheat 10 10 0 40 30 30 30 25 25 30 10 25 0 0 30 20 0 Wild buckwheat 100 100 90 80 100 100 100 100 100 100 100 100 100 35 95 90 0 Wild oat 10 25 0 10 20 35 0 25 30 45 10 25 10 0 25 0 0 NJ VO NJ NJ Table C COMPOUND Rate 16 g/ha 1 2 3 4 5 7 8 9 10 11 12 13 14 20 21 23 24 25 26 27 28 29 POSTEMERGENCE Barley Igri 30 35 35 25 30 0 0 10 20 20 10 40 25 30 30 30 0 35 15 15 10 0 Barnyard 2 15 30 10 15 15 0 0 0 0 25 0 0 0 0 10 20 0 0 10 10 10 10 Barnyardgrass 35 30 25 35 35 0 0 0 0 60 50 25 40 30 70 95 30 100 80 60 40 40 Bedstraw 65 85 95 50 95 40 50 30 20 0 40 35 40 90 90 100 95 100 30 40 40 40 Blackgrass 0 30 10 20 20 0 - 0 0 10 10 30 20 10 10 20 10 25 10 10 10 10 Chickweed 10 45 10 20 60 40 - 50 40 45 10 30 55 95 100 100 95 100 50 50 25 0 Cocklebur 80 90 90 80 90 70 70 60 60 80 30 50 40 100 100 100 100 100 70 80 50 50 Corn 15 10 15 25 20 10 10 10 10 20 20 25 10 25 35 20 20 20 25 20 10 10 Cotton 90 100 100 90 100 90 90 90 70 100 80 90 85 100 100 100 100 100 100 100 80 90 ■NJ Crabgrass 25 40 30 20 35 20 10 10 10 15 25 25 35 - 30 50 20 50 25 20 15 15 NJ NJ Downy Brome 20 30 10 25 0 0 0 0 0 0 10 20 15 20 0 25 0 0 10 0 0 0 Duck salad 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Giant foxtail 25 50 30 35 40 0 10 15 0 20 25 30 25 35 60 50 30 40 25 15 20 15 Italn. Rygrass 25 10 0 20 15 0 0 0 0 0 0 0 20 20 0 15 0 0 0 0 0 0 Johnsongrass - 25 40 30 30 0 0 0 10 35 20 35 25 20 25 50 20 50 30 30 20 10 Lambsquarter 65 95 100 95 85 40 40 40 30 95 - - 100 100 100 100 - 100 90 90 95 60 Morningglory 90 100 85 80 90 90 70 - 50 90 40 50 35 100 100 100 100 100 90 90 70 50 Rape 85 95 10 40 70 10 10 20 30 95 75 90 80 100 100 100 100 100 30 35 0 0 Redroot Pigweed 80 100 90 90 80 60 40 20 20 90 100 100 100 100 100 100 90 90 - 100 60 80 Rice Japonica 15 30 15 15 25 0 0 0 0 25 0 25 10 0 20 20 0 0 20 20 15 0 Soybean 30 50 35 50 35 20 25 25 25 20 10 50 25 70 35 35 35 40 25 45 25 25 Speedwell 90 90 100 100 100 70 30 0 0 0 35 80 80 100 100 100 100 100 90 80 30 0 Sugar beet 100 100 100 100 95 - - 30 60 100 100 100 100 100 100 100 100 100 100 100 40 30 Umbrella sedge 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 0 0 0 0 0 Velvetleaf 100 100 100 100 100 80 80 30 50 100 95 90 100 100 100 100 100 100 100 100 75 30 Watergrass 2 10 30 10 15 15 - - - - 10 0 45 0 0 0 20 - - 25 10 10 0 Wheat 25 15 25 25 30 0 0 0 0 10 10 40 10 10 10 25 0 25 15 10 0 0 Wild buckwheat 65 75 90 100 95 50 40 50 50 70 50 95 95 100 100 100 70 100 95 95 70 30 Wild oat 30 35 35 25 25 0 20 0 20 10 35 35 30 35 20 25 0 10 15 15 10 0 NJ NJ Table C COMPOUND Rate 16 g/ha 30 31 32 33 34 35 36 37 39 40 41 42 43 44 45 46 48 49 52 53 54 56 POSTEMERGENCE Barley Igri 25 30 20 25 30 30 20 20 15 20 10 30 15 10 0 0 0 25 30 30 30 25 Barnyard 2 0 0 0 0 0 0 - - 45 50 0 - 0 0 - 0 0 - 0 0 0 0 Barnyardgrass 90 30 50 15 10 10 10 60 100 80 80 90 75 90 50 35 40 80 100 70 95 35 Bedstraw 50 60 95 90 90 85 100 100 90 100 100 70 75 100 80 0 10 50 85 85 85 85 Blackgrass 10 10 10 10 10 20 25 25 20 30 20 25 10 10 - 0 20 10 20 20 20 10 Chickweed 85 90 100 95 95 80 100 100 100 95 100 100 95 100 - 0 45 80 95 100 95 50 Cocklebur 100 80 100 60 90 50 100 100 90 100 100 100 100 100 100 50 40 90 100 100 100 70 Corn 20 25 20 20 20 10 10 10 35 25 10 20 10 15 10 10 10 20 30 15 15 10 Cotton 100 100 100 90 100 90 100 100 100 100 100 100 100 100 100 100 80 100 100 100 100 70 Crabgrass 20 60 60 20 20 30 10 15 35 50 20 20 20 10 10 20 35 20 20 30 40 40 Downy Brome 0 0 0 10 10 0 10 20 10 30 0 10 15 100 0 0 10 0 20 10 0 10 Duck salad 0 0 0 0 0 0 - - 0 10 0 - 0 0 - 0 0 - 0 0 0 0 Giant foxtail 25 50 60 20 20 30 10 15 50 50 20 30 40 25 20 20 30 15 30 30 35 30 Italn. Rygrass 10 0 0 10 10 0 10 10 10 35 10 0 ' 10 0 10 0 10 0 10 0 0 10 Johnsongrass 10 30 10 30 40 20 0 10 30 30 20 15 30 35 0 20 - 40 25 30 30 30 Lambsquarter 95 100 100 95 95 90 80 90 100 100 100 100 100 100 100 50 0 85 100 100 100 70 Morningglory 100 90 100 90 90 90 100 100 100 100 100 100 100 100 100 100 80 70 100 100 100 70 Rape 95 70 100 95 95 70 100 100 100 100 100 100 100 100 100 80 80 - 100 100 100 75 Redroot Pigweed 80 80 100 70 80 60 100 100 100 100 100 100 100 100 100 90 40 70 100 85 100 75 Rice Japonica 0 0 0 0 0 0 - - 30 30 0 - 0 0 - 0 0 - 0 0 0 0 Soybean 40 70 35 60 50 40 0 60 - 35 25 20 30 30 10 30 30 20 50 30 40 40 Speedwell 85 95 100 75 90 90 100 100 100 100 100 100 100 100 100 35 0 85 - 100 100 Sugar beet 100 95 100 100 100 100 90 100 100 100 100 100 100 90 - 100 60 100 100 100 100 20 Umbrella sedge 0 0 0 0 0 0 - - 0 0 0 - 0 0 - 0 0 - 0 0 0 0 Velvetleaf 100 70 100 60 90 85 100 100 100 100 100 100 100 100 100 100 80 100 100 100 100 90 Watergrass 2 ιo - - - - - - - 65 50 - - - - - 0 - - - - - - Wheat 20 20 25 30 35 30 0 0 20 15 20 35 10 0 0 30 0 30 25 20 20 20 Wild buckwheat 100 80 90 90 100 95 100 100 90 100 100 95 100 90 90 70 65 95 100 100 100 95 Wild oat 25 20 25 20 10 35 0 25 20 15 10 0 10 100 0 0 15 10 30 0 20 25 • NJ NJ Table C COMPOUND Rate 8 g/ha 1 3 4 5 . 7 8 9 10 11 12 13 14 20 21 22 23 24 25 26 27 28 29 POSTEMERGENCE Barley Igri 30 30 20 30 0 0 0 10 20 10 35 20 30 10 40 30 0 35 10 10 0 0 Barnyard 2 0 10 15 10 0 0 0 0 25 0 0 0 0 0 - 15 0 0 10 10 10 10 Barnyardgrass 35 20 20 30 0 0 0 0 50 30 20 25 20 60 95 75 20 70 75 40 30 30 Bedstraw 50 50 50 80 30 20 0 20 0 40 20 0 20 - 45 100 95 85 30 40 25 40 Blackgrass 0 0 20 10 0 0 0 0 10 10 25 10 10 10 10 20 0 20 0 10 Chickweed 0 10 15 50 20 - 20 - 35 10 30 55 80 100 90 100 80 100 50 50 Cocklebur 50 80 40 85 60 70 40 60 70 20 45 25 80 100 100 100 100 100 50 70 Corn 10 10 20 15 10 10 10 10 10 15 25 10 25 25 30 15 10 10 15 15 Cotton 90 100 90 100 90 60 70 - 90 80 85 55 100 100 100 100 100 100 90 90 Crabgrass 25 30 20 30 10 10 10 10 10 20 25 30 25 30 35 50 15 35 15 20 NJ > o Downy Brome 10 10 10 0 0 0 0 0 0 0 20 10 20 0 0 10 0 0 10 0 Duck salad 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 Giant foxtail 25 25 35 30 0 5 10 0 20 15 30 15 25 40 30 40 20 30 20 10 Italn. Rygrass 20 0 10 10 '0 0 0 0 0 0 0 20 20 0 0 10 0 0 0 0 Johnsongrass - 40 20 30 0 0 0 0 10 10 25 10 10 20 40 25 15 20 20 20 Lambsquarter 60 95 95 85 40 40 20 20 95 - - 100 100 100 100 100 95 100 90 90 Morningglory 85 85 75 80 90 40 100 50 80 35 50 30 100 100 100 100 80 100 85 90 Rape 85 - 30 70 10 10 0 20 80 65 90 60 100 100 100 100 100 100 0 20 Redroot Pigweed 80 80 90 60 60 40 20 - 90 100 100 100 100 100 100 100 80 90 75 80 60 70 Rice Japonica 10 10 15 25 0 0 0 0 25 0 0 10 0 20 - 20 0 0 20 20 10 0 Soybean 25 35 40 30 20 20 20 20 20 - 50 10 70 35 50 20 25 35 20 40 15 10 Speedwell 90 70 100 - 30 - 0 0 0 30 80 - 95 100 100 - 90 100 85 70 0 0 Sugar beet 100 100 100 95 - - - 60 100 100 100 100 90 100 100 100 100 100 95 95 30 0 Umbrella sedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 Velvetleaf 100 90 100 100 80 60 0 50 100 95 90 100 100 100 100 100 100 100 100 80 30 20 Watergrass 2 10 10 10 10 - - - - 10 0 0 0 0 0 - 15 - - 20 10 10 0 Wheat 25 25 25 25 0 0 0 0 10 10 40 0 10 10 25 25 0 20 0 0 0 0 Wild buckwheat 65 90 100 95 30 30 30 40 70 25 85 90 100 100 100 - 70 100 70 70 40 10 Wild oat 25 35 20 20 0 10 0 10 10 10 35 25 30 15 50 15 0 0 10 10 0 0 NJ J Table C COMPOUND Rate 8 g/ha 30 31 32 33 34 35 36 37 39 40 41 42 43 44 45 46 48 49 52 53 54 56 POSTEMERGENCE Barley Igri 20 30 10 25 30 30 10 20 10 10 0 30 10 10 0 0 0 20 30 20 30 25 Barnyard 2 0 0 0 0 0 0 - - 35 40 0 - 0 0 - 0 0 - 0 0 0 0 Barnyardgrass 80 20 40 10 10 10 10 45 70 80 60 70 30 80 30 25 40 50 70 60 95 15 Bedstraw 50 60 - 80 60 85 100 70 90 80 100 70 40 90 60 0 0 50 50 60 80 85 Blackgrass 10 10 10 0 10 20 10 25 10 25 10 10 0 10 35 0 10 10 10 20 20 10 Chickweed 80 70 100 65 95 70 100 75 90 95 100 95 90 90 - 0 0 60 75 70 90 30 Cocklebur 100 70 100 60 70 30 100 100 90 100 100 100 100 100 100 10 30 50 100 100 100 30 Corn 10 15 15 15 15 10 5 5 20 15 10 15 5 10 5 10 0 10 20 10 10 10 Cotton 95 100 100 80 100 90 100 100 100 100 100 100 100 100 100 90 60 100 100 100 100 70 Crabgrass 15 50 40 10 20 20 10 15 30 30 15 15 20 10 10 10 20 15 20 20 30 10 ω NJ Downy Brome 0 0 0 10 10 0 0 0 10 10 0 10 10 100 0 0 0 0 10 0 0 10 Duck salad 0 0 0 0 0 0 - - 0 0 0 - 0 0 - 0 0 - 0 0 0 0 Giant foxtail 20 50 50 10 20 20 10 15 40 35 15 25 20 15 15 10 20 10 25 20 30 20 Italn. Rygrass 0 0 0 10 0 0 0 0 10 20 0 0 0 0 10 0 0 0 10 0 0 10 Johnsongrass 0 20 10 20 30 10 0 10 - 30 15 10 20 25 0 10 - 30 15 30 30 20 Lambsquarter 90 80 100 65 90 80 80 90 100 100 90 95 90 95 100 50 0 70 100 100 100 60 Morningglory 100 90 100 90 90 90 100 100 100 100 100 100 100 100 100 75 70 70 100 100 100 Rape 90 30 100 90 60 70 100 100 100 100 100 100 100 100 100 0 25 95 100 100 100 70 Redroot Pigweed 65 60 100 60 80 60 80 100 100 100 100 90 100 100 90 80 30 50 100 70 90 30 Rice Japonica 0 0 0 0 0 0 - - 25 25 0 - 0 0 - 0 0 - 0 0 0 0 Soybean 35 70 30 50 40 40 70 60 30 35 15 15 25 25 10 20 20 15 50 30 40 20 Speedwell 70 95 90 10 90 75 90 90 100 100 80 95 90 100 30 - 75 100 100 100 20 Sugar beet 100 95 100 95 100 100 90 100 100 100 100 100 100 80 - 0 10 100 100 100 100 15 Umbrella sedge 0 0 0 0 0 0 - - 0 0 0 - 0 0 - 0 0 - 0 0 0 0 Velvetleaf 100 70 100 60 70 - 100 100 100 100 100 100 100 100 100 80 70 90 100 100 100 30 Watergrass 2 10 40 40 0 Wheat 15 0 10 30 35 30 0 0 20 10 10 25 0 0 0 0 0 10 20 10 10 10 Wild buckwheat 95 80 90 75 95 90 90 100 90 100 90 95 100 90 80 30 40 80 100 100 100 95 Wild oat 25 20 10 10 0 30 0 0 10 10 5 0 10 100 0 0 0 0 30 0 0 15 sJ Table C COMPOUND Rate 8 g/ha 57 58 60 64 65 68 69 70 73 POSTEMERGENCE Barley Igri 25 0 0 0 10 Barnyard 2 0 0 - 0 0 Barnyardgrass 30 10 10 30 20 Bedstraw 95 65 20 70 40 Blackgrass 15 0 0 10 0 Chickweed 60 45 70 90 20 Cocklebur 80 100 100 90 90 Corn 20 10 5 10 5 Cotton 100 100 100 100 50 Crabgrass Downy Brome Duck salad Giant foxtail 50 15 10 15 10 Italn. Rygrass 30 0 0 0 0 Johnsongrass 60 10 0 10 0 Lambsquarter 95 80 60 85 50 Morningglory 90 100 100 100 60 Rape 60 100 90 85 100 Redroot Pigweed 100 80 90 90 60 Rice Japonica 0 0 - 0 0 Soybean 80 20 15 20 20 Speedwell 95 15 95 50 80 Sugar beet 20 55 95 100 Umbrella sedge 0 0 - 0 0 Velvetleaf 100 100 100 100 50 Watergrass .2 Wheat 25 0 0 0 0 0 25 10 0 Wild buckwheat 100 85 90 - 100 0 - 80 0 Wild oat 35 0 0 0 0 0 20 0 0 Table C COMPOUND Rate 4 g/ha 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 39 40 41 42 43 POSTEMERGENCE Barley Igri 20 40 25 0 20 0 0 0 0 Barnyard 2 10 - 15 0 0 10 10 10 10 Barnyardgrass 60 75 60 10 50 35 30 20 20 Bedstraw 40 45 95 80 85 10 10 20 10 Blackgrass 10 10 20 0 20 0 10 0 0 Chickweed 100 35 90 80 95 30 30 0 0 65 70 95 65 70 45 70 75 70 80 100 85 90 Cocklebur 100 100 100 70 100 30 60 30 30 90 50 100 40 40 20 100 100 90 100 100 100 100 Corn 15 30 10 5 10 10 5 0 0 10 15 10 10 10 10 5 5 15 10 5 10 5 Cotton 100 100 100 90 100 80 90 40 40 90 100 100 80 90 85 90 100 100 100 100 100 100 Crabgrass 25 35 35 10 30 10 10 0 10 10 35 25 10 15 15 10 15 25 30 10 10 10 ω O Downy Brome 0 0 0 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 Duck salad 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 - - 0 0 0 - 0 Giant foxtail 35 25 40 10 25 10 10 10 10 10 40 40 10 15 15 10 10 30 30 10 15 10 Italn. Rygrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 Johnsongrass 35 30 15 10 20 10 10 0 0 0 15 5 20 20 10 0 0 15 30 10 5 10 Lambsquarter 100 100 - 90 95 85 90 80 35 80 0 100 45 80 80 80 80 90 100 70 80 80 Morningglory 100 100 100 70 100 85 90 35 25 95 90 100 80 90 90 70 100 100 100 100 100 100 Rape 100 100 95 100 100 0 0 0 0 85 30 100 65 40 10 80 100 95 100 100 100 90 Redroot Pigweed 100 100 100 70 80 70 65 30 50 40 45 100 60 70 50 70 90 100 100 100 85 100 Rice Japonica 0 - 20 0 0 15 20 10 0 0 0 0 0 0 0 - - 20 25 0 - 0 Soybean 35 40 15 15 25 10 40 0 0 20 50 25 40 40 30 50 50 30 35 10 10 20 Spppdwe11 100 100 90 90 100 80 0 0 0 60 90 - 10 70 60 90 90 100 95 80 90 Sugar beet 100 100 100 95 100 90 95 0 0 100 95 100 - 100 95 80 95 100 100 100 100 100 Umbrella sedge 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 - - 0 0 0 - 0 Velvetleaf 100 100 100 90 100 100 80 20 10 100 60 100 60 70 60 100 100 100 100 100 100 100 Watergrass 2 0 - 15 - - 10 10 10 0 10 - - - - - - - 25 20 - - - Wheat 20 20 10 0 10 0 0 0 0 0 0 0 10 25 25 0 0 10 10 0 20 0 Wild buckwheat 100 100 100 - 100 70 30 25 10 95 30 90 75 80 90 70 90 90 90 90 90 90 Wild oat 10 40 15 0 0 10 0 0 0 25 20 10 10 0 0 0 0 10 10 0 0 10 TO J vo NJ *» 10 65 100 100 100 0 10 45 95 100 10 80 - 0 0 - 0 0 0 0 0 0 - 0 0 0 - 0 0 50 100 100 100 0 90 90 100 100 40 90 100 0 0 10 10 0 0 0 15 0 0 0 0 25 0 0 20 60 95 95 100 0 95 65 70 85 0 70 50 0 0 0 25 0 0 0 30 0 0 0 0 10 0 0 NJ NJ Table C COMPOUND Rate 2 g/ha 21 22 23 24 25 26 28 30 31 32 33 34 35 39 40 41 42 43 44 46 48 52 POSTEMERGENCE Barley Igri 10 35 10 0 0 0 0 10 10 0 0 20 0 0 0 0 10 0 10 0 0 20 Barnyard 2 0 - 15 0 0 10 10 0 0 0 0 0 0 10 20 0 - 0 0 0 0 0 Barnyardgrass 35 60 50 10 40 20 10 30 10 20 10 10 0 40 40 20 30 20 30 0 20 35 Bedstraw 40 40 85 80 55 0 0 30 30 75 40 40 60 75 80 40 30 - 80 0 0 10 Blackgrass 10 10 10 0 10 0 0 10 0 0 0 0 0 0 20 0 5 0 0 0 0 0 Chickweed 80 20 75 10 70 20 0 60 70 75 65 50 40 60 80 80 65 80 90 0 0 30 Cocklebur 100 80 100 70 100 - 10 40 35 90 30 20 20 90 100 90 100 90 100 0 20 100 Corn 15 25 10 0 0 0 0 0 15 10 5 10 5 10 10 5 5 5 5 0 0 10 Cotton 100 100 100 90 100 60 25 80 90 90 70 80 80 100 100 100 100 100 100 30 40 90 Crabgrass 25 30 25 5 30 10 0 10 25 15 10 15 10 20 30 0 5 0 0 0 0 20 Downy Brome 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 Duck salad 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 Giant foxtail 25 20 35 10 20 0 0 0 20 35 10 10 10 25 30 10 10 10 10 0 0 10 Italn. Rygrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 Johnsongrass 30 25 10 10 10 10 0 0 10 5 15 10 10 - 20 0 5 0 10 0 0 10 Lambsquarter 100 95 100 70 95 85 40 80 - 95 35 45 50 90 100 70 50 65 90 45 0 95 Morningglory 100 85 100 40 100 65 15 95 80 100 40 70 70 100 100 100 100 90 100 20 20 90 Rape 100 100 95 90 100 0 0 70 30 90 50 40 10 90 90 90 95 90 100 0 10 95 Redroot Pigweed 100 100 100 70 80 35 20 10 40 95 50 60 40 100 90 85 70 100 80 - 10 95 Rice Japonica 0 - 20 0 0 15 - 10 0 0 0 0 0 0 15 15 0 - 0 0 0 0 0 Soybean 25 35 15 10 20 0 0 15 40 20 30 40 25 30 30 10 5 15 15 0 0 30 Speedwell 70 90 85 10 95 70 0 30 55 80 10 55 20 100 - 60 30 80 75 0 0 0 Sugar beet 100 100 100 70 100 90 0 100 50 55 90 100 30 80 100 100 100 100 60 0 0 100 Umbrella sedge 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 Velvetleaf 100 100 100 90 100 40 10 70 40 100 20 60 20 100 100 100 100 100 100 30 30 100 Watergrass 2 0 - 10 - - 10 10 0 15 20 - - - - 0 - - Wheat 0 20 10 0 0 0 0 0 0 0 0 0 0 10 0 0 10 0 0 0 0 10 Wild buckwheat 100 95 100 55 100 45 20 90 30 85 65 75 75 80 90 80 10 80 80 0 20 80 Wild oat 10 35 10 0 0 0 0 10 10 0 0 0 0 10 0 0 0 0 10 0 0 15 •NJ COMPOUND COMPOUND 22 39 40 22 39 40 30 0 0 0 0 10 0 50 30 30 35 30 70 50 0 10 0 15 0 10 50 70 0 70 90 100 0 25 10 10 0 10 20 90 100 100 10 0 0 25 10 30 0 0 0 0 0 10 20 20 0 0 0 80 20 25 10 10 40 50 95 90 100 0 0 0 70 95 100 30 95 90 90 90 0 0 0 85 100 90 95 20 95 - 10 10 10 20 20 35 25 20 - 60 70 80 70 75 0 0 0 95 70 100 0 0 0 0 0 0 0 0 40 100 100 - 10 0 20 0 0 90 65 90 25 0 0 TEST D Seeds of barnyardgrass (Echinochloa crus-galli), bindweed (Concolculus arvensis), black nightshade (Solanum ptycanthum dunal), cassia (Cassia obtusifolia), cocklebur (Xanthium strumarium), common ragweed (Ambrosia artemisiifolia), corn (Zea mays), cotton (Gossypium hirsutam), crabgrass (Digitaria spp.), fall panicum (Panicum dichotomiflorum), giant foxtail (Setariafaberii), green foxtail (Setaria viridis), jimsonweed (Datura stramonium), johnsongrass (Sorghum halepense), lambsquarter (Chenopodium album), morningglory (Ipomoea spp.), pigweed (Amaranthus retrqflexus), prickly sida (Sida spinosa), shattercane (Sorghum vulgare), signalgrass (Brachiaria platyphylla), smartweed (Polygonum pensylvanicum), soybean (Glycine max), sunflower (Helianthus annuus), velvetleaf (Abutilon theophrasti), wild proso (Pancium miliaceum), woolly cupgrass (Eriochloa villosa), yellow foxtail (Setaria lutescens) and purple nutsedge (Cyperus rotundus) tubers were planted into a sandy loam soil. These crops and weeds were grown in the greenhouse until the plants ranged in height from two to eighteen cm (one to four leaf stage), then treated postemergence with the test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. Pots receiving preemergence treatments were planted immediatley prior to test chemical application. Pots treated in this fashion were placed in the greenhouse and maintained according to routine greenhouse procedures. Treated plants and untreated controls were maintained in the greenhouse approximately 14-21 days after application of the test compound. Visual evaluations of plant injury responses were then recorded. Plant response ratings, summarized in Table D, are reported on a 0 to 100 scale where 0 is no effect and 100 is complete control. Table D COMPOUND Rate 4 g/ha 20 21 23 25 32 POSTEMERGENCE Barnyardgrass 10 40 30 0 10 Bindweed 100 100 100 100 100 Blk Nightshade 70 100 100 100 100 Cassia 50 5 0 5 0 Cocklebur 85 100 100 100 100 Corn 5 5 10 5 10 Cotton 95 100 100 100 100 Crabgrass 5 5 0 5 0 Fall Panicum 10 10 0 5 0 Giant Foxtail 10 30 40 10 40 Green Foxtail 10 5 10 20 5 Jimsonweed 70 70 100 100 100 Johnson Grass 40 5 5 5 5 Lambsquarter 75 90 50 40 30 Morningglory 100 100 100 100 100 Nutsedge 0 0 0 0 0 Pigweed 100 100 100 70 100 Prickly Sida 100 100 100 80 100 Ragweed 70 100 100 100 100 Shattercane 20 5 20 5 30 Signalgrass 10 10 0 0 0 Smartweed 50 60 50 30 40 Soybean 40 5 0 20 0 Sunflower 20 50 80 50 70 Velvetleaf 100 100 100 100 100 Wild Proso 10 5 30 10 10 Woolly cupgrass 5 20 10 5 30 Yellow Foxtail 10 10 5 5 30 TEST E Compounds evaluated in this test were formulated in a non-phytoxic solvent mixture which included a surfactant and applied to the soil surface before plant seedlings emerged (preemergence application) and to plants that were in the one-to four leaf stage (postemergence application). A sandy loam soil was used for the preemergence test while a mixture of sandy loam soil and greenhouse potting mix in a 60:40 ratio was used for the postemergence test. Test compounds were applied within approximately one day after planting seeds for the preemergence test. Plantings of these crops and weed species were adjusted to produce plants of appropriate size for the postemergence test. All plant species were grown using normal greenhouse practices. Crop and weed species include annual bluegrass (Poa annua), black nightshade (Solanum nigra), blackgrass (Alopecurus grown using normal greenhouse practices. Crop and weed species include annual bluegrass (Poa annua), black nightshade (Solanum nigra), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), deadnettle (Lamium amplexicaule), downy brome (Bromus tectorum), field violet (Viola arvensis), galium (Galium aparine), green foxtail (Setaria viridis), jointed goatgrass (Aegilops cylindrica), kochia (Kochia scoparia), lambsquarters (Chenopodium album), littleseed canarygrass (Phalaris minor), rape (Brassica napus), redroot pigweed (Amaranthus retroflexus), Russian thistle (Salsola kali), ryegrass (Lolium multiflorum), sentless chamonile (Matricaria inodora), speedwell (Veronica persica), spring barely (Hordeum vulgare cv. 'Klages'), spring wheat (Triticum aestivum cv. 'ERA'), sugar beet (Beta vulgaris cv. VSϊ), sunflower (Helianthus annuus cv. 'Russian Giant'), Veronica hederaefolia, wild buckwheat (Polygonum convolvulus), wild mustard (Sinapis arvensis), wild oat (Avena fatua), windgrass (Apera spica-venti), winter barley (Hordeum vulgare cv. 'Igri') and winter wheat (Triticum aestivum cv. 'Talent'). Treated plants and untreated controls were maintained in a greenhouse for approximately 21 to 28 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table E, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash response (-) means no test result. Table E COMPOUND Table E COMPOUND Rate 62 g/ha 20 Rate 62 g/ha 20 POSTEMERGENCE PREEMERGENCE Annual Bluegras Blk Nightshade 100 Blackgrass (2) Chickweed 95 Blk Nightshade 100 Deadnettle 100 Chickweed 100 Field violet 75 Deadnettle 100 Galium (2) 100 Downy brome Kochia 100 Field violet 95 Lambsquarters 100 Galium (2) 100 Redroot Pigweed 100 Green foxtail Russian Thistle Jointed Goatgra Scentless Chamo Kochia 100 Speedwell 100 Lambsquarters 100 Spring Barley 30 LS Canarygrass Veronica hedera Rape Wheat (Spring) 5 Redroot Pigweed 100 Wheat (Winter) 5 Russian Thistle Wild buckwheat 100 Ryegrass Winter Barley 30 Scentless Chamo 100 Speedwell 100 Spring Barley 45 Sugar beet Sunflower Veronica hedera Wheat (Spring) 35 Wheat (Winter) 15 Wild buckwheat 100 Wild mustard Wild oat (2) Winter Barley 25 Table E COMPOUND Rate 16 g/ha 3 4 5 12 13 14 20 21 23 25 30 48 52 53 54 POSTEMERGENCE Annual Bluegras 10 10 20 Blackgrass (2) 20 20 20 - - - - - - - - - - - - Blk Nightshade 100 100 100 - 100 100 100 100 100 100 100 100 100 Chickweed 20 10 10 50 - - 100 100 100 100 30 20 100 75 100 Deadnettle 30 20 30 25 50 30 80 100 80 60 40 20 60 60 45 Downy brome _ _ _ _ _ _ _ _ 20 - - - - - - Field violet 60 60 55 70 70 55 85 100 60 100 100 15 100 100 100 Galium (2) 60 60 35 30 30 30 100 100 100 100 50 30 100 95 100 Green foxtail _ _ _ _ _ _ _ _ IQO _ _ _ _ _ _ Jointed Goatgra _ _ _ _ _ _ _ _ 3o - - - - - - Kochia 100 100 100 100 100 100 100 100 100 100 100 45 100 100 100 Lambsquarters 55 60 30 100 100 70 100 100 100 100 100 40 100 100 100 LS Canarygrass 30 20 20 - - - - - - - - - - - - Rape 75 70 60 - - - - - 100 _ _ _ _ _ _ σ » Redroot Pigweed 60 50 55 - - - 100 100 100 100 100 45 100 100 100 Russian Thistle - 100 100 100 _ _ _ _ _ _ _ _ _ Ryegrass _ _ _ _ _ _ _ _ 30 - - - - - - Scentless Chamo Speedwell Spring Barley Sugar beet Sunflower Veronica hedera Wheat (Spring) Wheat (Winter) Wild buckwheat Wild mustard Wild oat (2) Winter Barley Table E Rate 16 g/ha PREEMERGENCE Blk Nightshade Chickweed Deadnettle Field violet Galium (2) Kochia Lambsquarters Redroot Pigweed Russian Thistle Scentless Chamo Speedwell Spring Barley Veronica hedera Wheat (Spring) Wheat (Winter) Wild buckwheat Winter Barley Table E COMPOUND Rate 8 g/ha 3 4 5 12 13 14 20 21 23 25 30 32 33 34 35 43 48 49 52 53 54 55 POSTEMERGENCE Annual Bluegras ιo 10 10 - - - - - - - - - - - - - - - - - - - Blackgrass (2) 10 20 10 - - - - - - - - - - - - - - - - - - - Blk Nightshade 100 100 100 - - - 100 100 100 100 100 100 100 100 100 100 35 100 100 100 100 - Chickweed 10 10 10 - - - 85 100 100 100 20 100 100 100 60 100 20 70 100 60 100 Deadnettle 15 10 30 40 40 40 60 60 70 75 30 60 45 65 55 100 10 45 50 50 60 50 Downy brome _ _ _ _ _ _ _ _ 20 - - - - - - - - - - - - - Field violet 60 55 30 50 60 35 75 70 70 100 100 100 100 100 100 100 10 60 100 100 100 80 Galium (2) 40 35 40 40 30 40 100 100 95 100 30 100 55 100 65 100 30 50 100 95 60 70 Green foxtail _ _ _ _ _ _ _ _ 4o _ - _ - - - - - - - - - - Jointed Goatgra - - - - - - - - o - - - - - - - - - - - - - Kochia Lambsquarters LS Canarygrass Rape Redroot Pigweed Russian Thistle Ryegrass Scentless Chamo Speedwell Spring Barley Sugar beet Sunflower Veronica hedera Wheat (Spring) Wheat (Winter) Wild buckwheat Wild mustard Wild oat (2) Winter Barley Table E COMPOUND Rate 8 g/ha 20 21 25 30 31 32 52 53 54 PREEMERGENCE Blk Nightshade 90 50 20 20 0 30 50 60 50 Chickweed 35 30 75 25 30 70 30 20 30 Deadnettle 10 0 10 20 20 60 10 20 50 Field violet 0 20 10 0 30 20 0 0 30 Galium (2) 80 65 60 40 10 50 100 60 50 Kochia 90 100 30 10 20 20 0 0 Lambsquarters 100 90 100 50 70 30 100 100 100 Redroot Pigweed 100 90 100 100 70 30 100 70 100 Russian Thistle - 10 30 30 35 50 20 75 Scentless Chamo - 75 30 70 70 90 70 Speedwell 70 50 - - - Spring Barley 0 0 0 0 0 0 0 10 Veronica hedera - 75 0 70 40 - 65 75 Wheat (Spring) 0 0 0 10 0 0 10 0 0 Wheat (Winter) 0 0 0 0 0 0 20 0 0 Wild buckwheat 85 50 55 - 10 30 50 30 50 Winter Barley 0 10 20 20 0 0 25 0 10 NJ Table E COMPOUND Rate 2 g/ha 20 21 23 25 31 32 33 34 35 43 49 52 54 55 POSTEMERGENCE Annual Bluegras _ _ _ _ _ _ _ _ _ - _ - _ - Blackgrass (2) _ _ _ _ _ _ _ _ _ - - - _ - Blk Nightshade 100 100 100 100 60 100 100 100 70 100 60 100 100 80 Chickweed 30 75 100 65 20 50 30 50 30 60 20 Deadnettle 40 65 40 40 40 30 45 55 40 40 30 50 50 30 Downy brome _ _ 5 _ _ _ _ _ _ _ _ _ _ _ Field violet 35 40 50 75 70 100 65 100 100 100 30 50 70 50 Galium (2) 30 100 65 50 30 45 25 60 30 30 20 50 70 50 Green foxtail _ _ 2 5 _ _ _ _ _ _ _ _ _ _ _ Jointed Goatgra - _ ιo - - - - - - - - - - - Kochia 100 100 100 70 40 70 70 70 65 100 40 100 100 50 Lambsquarters 100 100 75 75 60 100 60 70 60 100 50 100 90 30 LS Canarygrass - - - - - - - - - - - - - - Rape - - 100 _ _ _ _ _ - - - - _ _ Redroot Pigweed 100 100 100 100 100 100 100 100 100 100 30 100 100 Russian Thistle - - - ιoo 70 100 100 100 100 100 50 Ryegrass - - 10 - - - - - - - - - - - Scentless Chamo 30 55 70 50 50 60 50 30 30 65 30 50 60 60 Speedwell 55 100 60 - - - - - - - - 100 60 60 Spring Barley 15 5 10 10 10 10 10 10 15 10 10 5 5 0 Sugar beet - - 100 _ _ _ _ _ _ _ _ _ _ _ Sunflower - _ 50 - - - - - - - - - - - Veronica hedera - - - 60 50 50 60 50 50 60 10 Wheat (Spring) 20 5 10 5 10 10 10 20 10 10 5 5 5 5 Wheat (Winter) 15 5 10 10 10 10 10 10 10 10 0 5 5 0 Wild buckwheat 100 100 100 100 55 100 30 65 70 100 50 100 100 60 Wild mustard _ _ _ _ _ _ _ _ _ _ _ _ _ _ Wild oat (2) - - 10 - - - - - - - - - - - Winter Barley 20 10 10 10 10 10 20 20 20 10 10 5 5 0 Table E COMPOUND Rate 1 g/ha 25 31 32 52 54 55 POSTEMERGENCE Annual Bluegras - - - - - - Blackgrass (2) Blk Nightshade 100 60 100 100 100 30 Chickweed 50 10 50 Deadnettle 30 30 30 20 50 30 Downy brome _ _ _ _ _ _ Field violet 70 50 65 50 60 30 Galium (2) 30 50 20 40 50 50 Green foxtail _ _ _ _ _ _ Jointed Goatgra - - - - - - Kochia 75 35 100 80 70 40 Lambsquarters 70 60 60 70 90 20 LS Canarygrass _ _ _ _ _ _ Rape _ _ _ _ _ _ Redroot Pigweed 100 100 100 100 100 30 Russian Thistle 100 70 75 Ryegrass _ _ _ _ _ _ Scentless Chamo 30 55 55 50 - 20 Speedwell - - - 50 50 50 Spring Barley 5 5 5 5 0 0 Sugar beet _ _ _ _ _ _ Sunflower _ _ _ _ _ _ Veronica hedera - 30 50 Wheat (Spring) 5 5 10 5 5 5 Wheat (Winter) 5 5 2 5 0 0 Wild buckwheat 100 45 55 20 60 50 Wild mustard _ _ _ _ _ _ Wild oat (2) _ _ _ _ _ _ Winter Barley 10 10 10 5 0 0 TEST F Compounds evaluated in this test were formulated in a non-phytoxic solvent mixture which included a surfactant and applied to the soil surface before plant seedlings emerged (preemergence application) and to plants that were grown for various periods of time before treatment (postemergence application). A sandy loam soil was used for the preemergence test while a mixture of sandy loam soil and greenhouse potting mix in a 60:40 ratio was used for the postemergence test. Test compounds were applied within approximately one day after planting seeds for the preemergence test. Plantings of these crops and weed species were adjusted to produce plants of appropriate size for the postemergence test. All plant species were grown using normal greenhouse practices. Crop and weed species include annual bluegrass (Poa annua), black nightshade (Solanum nigra), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), deadnettle (Lamium amplexicaule), downy brome (Bromus tectorum), field violet (Viola arvensis), galium (Galium aparine), green foxtail (Setaria viridis), jointed goatgrass (Aegilops cylindrica), kochia (Kochia scoparia), lambsquarters (Chenopodium album), littleseed canarygrass (Phalaris minor), rape (Brassica napus), redroot pigweed (Amaranthus retroflexus), Russian thistle (Salsola kali), ryegrass (Lolium multiflorum), sentless chamonile (Matricaria inodora), speedwell (Veronica persica), spring barely (Hordeum vulgare cv. 'Klages'), spring wheat (Triticum aestivum cv. 'ERA'), sugar beet (Beta vulgaris cv. 'US1'), sunflower (Helianthus annuus cv. 'Russian Giant'), Veronica hederaefolia, wild buckwheat (Polygonum convolvulus), wild mustard (Sinapis arvensis), wild oat (A vena fatua), windgrass (Apera spica-venti), winter barley (Hordeum vulgare cv. 'Igri') and winter wheat (Triticum aestivum cv. 'Talent'). Treated plants and untreated controls were maintained in a greenhouse for approximately 21 to 28 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table F, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash response (-) means no test result. Table F COMPOUND Rate 17 g/ha 21 22 23 25 30 32 39 40 48 52 53 54 60 64 69 71 POSTEMERGENCE Arrowleaw Sida 100 100 100 85 35 100 100 100 20 100 90 100 70 - 10 10 Barnyardgrass 40 35 30 25 10 15 65 65 5 25 20 55 55 85 40 10 Cocklebur 100 100 100 100 - 100 100 100 0 100 100 100 100 100 100 15 Common Ragweed 100 100 100 100 100 100 100 100 15 100 100 100 70 100 85 35 Corn 20 25 20 10 10 15 15 15 0 15 10 10 15 20 20 5 Cotton 100 100 100 100 100 100 100 100 65 100 100 100 100 100 100 100 Estrn Blknight 100 100 90 100 75 100 100 100 0 100 100 100 100 100 100 35 Fall Panicum 40 35 30 10 10 60 35 35 10 10 10 15 20 20 5 5 Field Bindweed 100 100 100 100 100 100 100 100 20 100 100 100 100 100 100 25 FI Beggarweed 100 100 50 70 75 70 90 85 15 70 80 70 60 80 15 35 Giant Foxtail 45 30 25 20 5 20 30 35 5 25 15 25 25 25 10 10 «_ Hairy Beggartic 100 100 100 65 85 100 100 100 5 100 100 100 100 100 100 20 > Ivyleaw Mrnglry 100 100 100 75 35 100 100 100 25 75 100 100 100 100 100 10 Johnsongrass 30 30 25 20 10 15 30 35 5 10 10 15 15 10 10 0 Ladysthumb 100 90 90 50 55 100 100 100 0 60 45 35 80 20 40 15 Lambsquarters 95 85 100 90 90 100 100 100 15 100 - - 70 95 50 55 Large Crabgrass 20 25 15 15 10 15 30 35 10 20 15 20 15 50 10 10 Purple Nutsedge 65 30 0 0 0 10 0 0 0 0 0 0 0 0 0 0 Redroot Pigweed 100 100 100 100 100 100 - - 75 100 100 100 100 100 90 100 Soybean 45 50 - 50 30 15 45 50 5 35 40 25 20 50 60 5 Surinam Grass 25 35 15 25 5 15 25 30 10 20 20 25 40 25 10 10 Velvetleaf 100 100 100 100 100 100 100 100 15 100 100 100 90 100 100 25 Wild Poinsettia 100 100 100 100 80 100 100 100 10 100 100 100 100 100 100 60 Table F COMPOUND Rate 17 g/ha 21 22 23 25 30 32 39 40 48 52 53 54 71 PREEMERGENCE Arrowleaw Sida 100 100 100 65 50 90 100 100 0 100 100 100 0 Barnyardgrass 10 0 0 0 0 10 0 0 0 0 5 10 0 Cocklebur 100 0 - 100 25 60 100 100 0 100 45 50 0 Common Ragweed 100 40 70 100 75 100 100 100 5 100 100 100 0 Corn 0 10 0 0 0 10 0 0 0 0 0 0 0 Cotton 100 50 100 15 35 75 100 100 0 100 45 100 0 Estrn Blknight - 100 100 100 - - 10 100 100 100 55 Fall Panicum 0 30 10 0 0 0 40 15 0 0 0 0 10 Field Bindweed 100 - - 100 70 100 100 100 0 100 100 100 0 Fl Beggarweed 0 - - 100 25 10 100 100 0 100 100 100 0 Giant Foxtail 35 20 0 0 0 0 25 10 0 0 0 0 0 ^ Hairy Beggartic 100 - 100 70 100 85 100 100 0 60 90 100 0 ω Ivyleaw Mrnglry 90 10 100 100 50 100 55 30 0 100 100 100 0 Johnsongrass 0 0 0 0 0 0 0 0 0 0 0 - 0 Ladysthumb - - - 50 0 0 75 100 0 50 0 100 0 Lambsquarters 100 100 100 100 100 100 - - 0 100 100 100 35 Large Crabgrass 20 60 0 0 0 10 15 10 0 0 0 5 0 Purple Nutsedge - - - 0 0 0 0 0 0 0 0 0 0 Redroot Pigweed 100 100 100 100 75 100 100 100 0 100 100 100 10 Soybean 20 0 0 0 0 10 0 0 0 - 5 10 0 Surinam Grass 10 15 0 0 0 0 10 10 0 0 0 0 0 Velvetleaf 100 100 100 100 90 100 100 100 0 100 100 100 0 Wild Poinsettia 100 - 55 45 35 100 100 100 0 80 80 100 20 30 32 39 40 48 52 53 54 60 64 69 71 20 100 95 100 0 35 85 95 50 0 0 0 10 35 40 0 15 10 15 50 60 30 0 10 100 100 100 0 100 90 100 80 100 75 10 Common Ragweed 100 100 100 100 100 100 100 100 10 100 100 100 70 100 75 20 Corn 15 15 15 10 5 15 15 15 0 10 10 5 10 20 20 5 Cotton 100 100 100 100 95 100 100 100 30 100 100 100 80 100 95 45 Estrn Blknight 100 100 85 90 65 100 100 100 0 100 100 100 70 100 100 25 Fall Panicum 20 20 15 5 10 55 25 20 5 10 10 10 20 10 5 5 Field Bindweed 100 100 100 100 90 100 100 100 0 100 100 100 45 100 100 10 Fl Beggarweed 100 100 50 65 65 - 75 75 10 65 50 60 60 65 10 25 Giant Foxtail 25 20 10 10 0 20 20 20 0 15 10 15 20 15 10 0 ^ Hairy Beggartic 100 95 100 55 50 100 100 100 0 100 95 100 75 100 65 0 ^ Ivyleaw Mrnglry 100 100 100 65 20 100 100 100 10 70 100 100 85 100 50 0 Johnsongrass 25 25 15 15 10 10 25 25 0 0 10 10 10 10 10 0 Ladysthu b 75 65 45 35 40 100 70 100 0 45 40 20 70 80 40 10 Lambsquarters 80 85 100 90 80 80 100 100 10 100 - - 65 95 30 40 Large Crabgrass 15 15 5 15 10 15 15 20 5 15 10 15 10 20 10 5 Purple Nutsedge 45 20 0 0 0 10 0 0 0 0 0 0 0 0 0 0 Redroot Pigweed 100 100 100 100 100 100 - - 45 100 100 100 75 100 75 35 Soybean 40 45 30 40 10 15 35 35 5 30 35 20 - 30 50 5 Surinam Grass 20 30 10 20 0 15 15 25 0 15 15 15 30 5 10 0 Velvetleaf 100 100 100 100 60 100 100 100 0 100 100 100 65 100 100 0 Wild Poinsettia 100 100 100 100 70 100 100 100 0 100 100 100 100 100 100 45 Table F COMPOUND Rate 4 g/ha 21 22 23 25 30 32 39 40 48 52 53 54 60 64 69 71 POSTEMERGENCE Arrowleaw Sida 75 55 20 25 10 60 90 75 0 25 55 90 50 0 0 0 Barnyardgrass 20 20 10 10 0 10 20 20 0 0 10 15 45 10 10 0 Cocklebur 100 100 100 100 25 85 100 100 0 90 80 100 75 100 75 0 Common Ragweed 100 95 100 100 50 100 100 100 0 100 100 100 60 20 0 0 Corn 10 10 15 5 5 10 10 10 0 10 5 5 10 10 15 0 Cotton 100 100 100 100 95 100 100 100 25 100 100 100 75 90 80 35 Estrn Blknight 100 100 80 85 30 100 100 100 0 80 95 95 60 100 80 10 Fall Panicum 10 15 5 5 5 40 15 10 0 0 5 5 15 5 5 0 Field Bindweed 100 100 100 100 45 100 100 100 0 100 55 100 40 95 90 0 FI Beggarweed 60 100 30 45 30 50 70 60 0 60 30 35 50 55 10 0 Giant Foxtail 20 15 5 10 0 15 15 15 0 10 10 10 15 5 5 0 ^ Hairy Beggartic 100 60 100 40 25 80 95 100 0 65 75 100 70 100 65 0 < Ivyleaw Mrnglry 100 100 100 50 15 100 100 100 0 25 60 100 85 100 75 0 Johnsongrass 10 15 10 10 5 10 15 20 0 0 5 5 10 5 10 0 Ladysthumb 50 - 45 30 25 25 40 60 0 30 30 20 70 20 40 5 Lambsquarters 60 75 100 85 70 70 100 100 5 70 - - 60 80 20 20 Large Crabgrass 10 10 5 10 5 15 10 15 0 10 5 10 10 20 10 5 Purple Nutsedge 15 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Redroot Pigweed 100 100 100 100 40 100 - - 10 100 100 100 75 100 50 15 Soybean 35 35 25 30 0 10 25 30 0 20 10 15 15 30 50 0 Surinam Grass 15 25 5 15 0 15 10 20 0 10 10 10 20 5 10 0 Velvetleaf 100 100 100 60 35 100 100 100 0 100 100 100 45 100 100 0 Wild Poinsettia 100 100 100 100 25 100 100 100 0 90 100 100 100 100 100 0 to OO 280 O 971 281 282 TEST G Seeds, tubers, or plant parts of alexandergrass (Brachiaria plantaginea), bermudagrass (Cynodon dactylon), broadleaf signalgrass (Brachiaria plantyphylla), common purslane (Portulaca oleracea), common ragweed (Ambrosia elatior), cotton (Gossypium hirsutum), dallisgrass (Paspalum dilatatum), goosegrass (Eleusine indica), guineagrass (Panicum maximum), itchgrass (Rottboellia exaltata), Johnson grass (Sorghum halepense), large crabgrass (Digitaria sanguinalis), peanuts (Arachis hypogaea), pitted morningglory (Ipomoea lacunosa), purple nutsedge (Cyperus rotundus), sandbur (Cenchrus echinatus), sourgrass (Trichachne insularis), and Surinam grass (Brachiaria decumbens) were planted into greenhouse pots or flats containing greenhouse planting medium. Plant species were grown in separate pots or individual compartments. Preemergence applications were made within one day of planting the seed or plant part. Postemergence applications were applied when the plants were in the two to four leaf stage (three to twenty cm). Test chemicals were formulated in a non-phytotoxic solvent mixture which included a surfactant and applied preemergence and postemergence to the plants. Untreated control plants and treated plants were placed in the greenhouse and visually evaluated for injury 13 to 21 days after herbicide application. Plant response ratings, summarized in Table G, are based on a 0 to 100 scale where 0 is no injury and 100 is complete control. A dash (-) response means no test result. Table G Table G COMPOUND Rate 250 g/ha Rate 250 g/ha 21 23 52 57 POSTEMERGENCE PREEMERGENCE Alexandergrass Alexandergrass 65 0 0 0 Bermudagrass Bermudagrass 50 0 0 0 Brdlf Sgnlgrass Brdlf Sgnlgrass 100 70 60 0 Cmn Purslane Cmn Purslane 100 100 100 100 Cmn Ragweed Cmn Ragweed 100 100 100 Cotton Cotton 100 100 100 0 Dallisgrass Dallisgrass 65 30 10 0 Goosegrass Goosegrass 98 40 20 0 Guineagrass Guineagrass 0 0 25 0 Itchgrass Itchgrass 35 - 0 0 Johnson grass Johnson grass 65 0 0 0 Large Crabgrass Large Crabgrass 40 0 0 0 Peanuts Peanuts' 10 20 10 20 Pit Morninglory Pit Morninglory 100 100 100 40 Purple Nutsedge Purple Nutsedge 60 60 60 0 Sandbur Sandbur 100 35 25 60 Sourgrass Sourgrass 100 100 70 0 Sugarcane Sugarcane Surinam grass 30 20 Surinam grass 70 65 65 0 Table G COMPOUND Rate 125 g/ha 57 PREEMERGENCE Alexandergrass 0 Bermudagrass 0 Brdlf Sgnlgrass 0 Cmn Purslane 100 Cmn Ragweed 0 Cotton 0 Dallisgrass 0 Goosegrass 0 Guineagrass 0 Itchgrass 0 Johnson grass 0 Large Crabgrass 0 Peanuts 0 Pit Morninglory 0 Purple Nutsedge 0 Sandbur 0 Sourgrass 0 Sugarcane Surinam grass 0 Table G COMPOUND Table G COMPOUND Rate 35 g/ha 21 Rate 35 g/ha 21 POSTEMERGENCE PREEMERGENCE Alexandergrass Alexandergrass Bermudagrass Bermudagrass Brdlf Sgnlgrass Brdlf Sgnlgrass Cmn Purslane Cmn Purslane Cmn Ragweed Cmn Ragweed Cotton Cotton Dallisgrass Dallisgrass Goosegrass Goosegrass Guineagrass Guineagrass Itchgrass Itchgrass Johnson grass Johnson grass Large Crabgrass Large Crabgrass Peanuts 15 Peanuts 40 Pit Morninglory Pit Morninglory Purple Nutsedge Purple Nutsedge Sandbur Sandbur Sourgrass Sourgrass Sugarcane 15 Sugarcane 10 Surinam grass Surinam grass O 97/1 287 Table G COMPOUND Rate 32 g/ha 57 PREEMERGENCE Alexandergrass 0 Bermudagrass 0 Brdlf Sgnlgrass 0 Cmn Purslane 0 Cmn Ragweed 0 Cotton 0 Dallisgrass 0 Goosegrass 0 Guineagrass 0 Itchgrass 0 Johnson grass 0 Large Crabgrass 0 Peanuts 30 Pit Morninglory 40 Pit Morninglory 0 Purple Nutsedge 0 Purple Nutsedge 0 Sandbur Sandbur 0 Sourgrass 0 Sourgrass 0 Sugarcane Sugarcane Surinam grass 0 Surinam grass 0 288 Table G COMPOUND Table G COMPOUND Rate 17.5 g/ha 21 Rate 17.5 g/ha 21 POSTEMERGENCE PREEMERGENCE Alexandergrass Alexandergrass Bermudagrass Bermudagrass Brdlf Sgnlgrass Brdlf Sgnlgrass Cmn Purslane Cmn Purslane Cmn Ragweed Cmn Ragweed Cotton Cotton Dallisgrass Dallisgrass Goosegrass Goosegrass Guineagrass Guineagrass Itchgrass Itchgrass Johnson grass Johnson grass Large Crabgrass Large Crabgrass Peanuts 10 Peanuts 30 Pit Morninglory Pit Morninglory Purple Nutsedge Purple Nutsedge Sandbur Sandbur Sourgrass Sourgrass Sugarcane 65 Sugarcane 20 Surinam grass Surinam grass 292 Table G COMPOUND Table G COMPOUND Rate 2 g/ha 21 Rate 2 g/ha 21 POSTEMERGENCE PREEMERGENCE Alexandergrass Alexandergrass Bermudagrass Bermudagrass Brdlf Sgnlgrass Brdlf Sgnlgrass Cmn Purslane Cmn Purslane Cmn Ragweed Cmn Ragweed Cotton Cotton Dallisgrass Dallisgrass Goosegrass Goosegrass Guineagrass Guineagrass Itchgrass Itchgrass Johnson grass Johnson grass Large Crabgrass Large Crabgrass Peanuts 15 Peanuts 20 Pit Morninglory Pit Morninglory Purple Nutsedge Purple Nutsedge Sandbur Sandbur Sourgrass Sourgrass Sugarcane 5 Sugarcane 0 Surinam grass Surinam grass TEST H Compounds evaluated in this test were formulated in a non-phytoxic solvent mixture which included a surfactant and applied to the soil surface before plant seedlings emerged (preemergence application) and to plants that were grown for various periods of time before treatment (postemergence application). A sandy loam soil was used for the preemergence test while a mixture of sandy loam soil and greenhouse potting mix in a 60:40 ratio was used for the postemergence test. Test compounds were applied within approximately one day after planting seeds for the preemergence test, and 13 days after the last postemergence planting. Plantings of these crops and weed species were adjusted to produce plants of appropriate size for the postemergence test. All plant species were grown using normal greenhouse practices. Crop and weed species include Acanthospermum hispidum, alexandergrass (Brachiaria plantaginea), american black nightshade (Solanum americanum), apple-of-Peru (Nicandra physaloides), arrowleaf sida (Sida rhombifolia), brazilian sicklepod (Cassia tora Brazilian), brazilian signalgrass (Brachiaria decumbens), capim-colchao (Digitaria horizontalis), cristalina soybean (Glycine max Cristalina), florida beggarweed (Desmodium purpureum), hairy beggarticks (Bidens pilosa), slender amaranth (Amaranthus viridis), southern sandur (Cenchrus echinatus), tall morningglory (Ipomoea purpurea), tropical spiderwort (Commelina benghalensis), W20 Soybean (Glycine max W20), W4-4 Soybean (Glycine max W4-4) and wild pointsettia (Eupohorbia heterophylla). Treated plants and untreated controls were maintained in a greenhouse for approximately 13 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table H, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash response (-) means no test result. 294 Table H COMPOUND Table H COMPOUND Rate 35 g/ha 21 Rate 35 g/ha 21 POSTEMERGENCE PREEMERGENCE Acanthospermum 100 Acanthospermum 100 Alexandergrass 20 Alexandergrass 5 Apple-of-Peru 70 Apple-of-Peru 100 Arrowleaf Sida 100 Arrowleaf Sida 100 B. Signalgrass 10 B. Signalgrass 30 Bl. Nightshade 100 Bl. Nightshade 100 Braz Sicklepod 40 Braz Sicklepod 75 Capi -Colch 5 Capim-Colch 10 Crist. Soybean 60 Crist. Soybean 10 Fl . Beggarweed 100 Fl. Beggarweed 100 H. Beggarticks 100 H. Beggarticks 100 Morningglory 100 Morningglory 100 SI. Amaranth 85 SI. Amaranth 100 Southern Sandur 10 Southern Sandur 75 Tr. Spiderwort 100 Tr. Spiderwort 100 Wld Pointsettia 100 Wld Pointsettia 100 W20 Soybean 35 W20 Soybean 5 W4-4 Soybean 35 W4-4 Soybean 5 Table H Rate 17 g/ha POSTEMERGENCE Acanthospermum Alexandergrass Apple-of-Peru Arrowleaf Sida B. Signalgrass Bl . Nightshade Braz Sicklepod Capim-Colch Crist. Soybean Fl . Beggarweed H. Beggarticks Morningglory SI . Amaranth Southern Sandur Tr. Spiderwort Wld Pointsettia W20 Soybean W4-4 Soybean Table H Table H COMPOUND Rate 8 g/ha Rate 8 g/ha 21 POSTEMERGENCE PREEMERGENCE Acanthospermum Acanthospermum 100 Alexandergrass Alexandergrass 5 Apple-of-Peru Apple-of-Peru 100 Arrowleaf Sida Arrowleaf Sida 100 B. Signalgrass B. Signalgrass 20 Bl. Nightshade Bl. Nightshade 100 Braz Sicklepod Braz Sicklepod 15 Capim-Colch Capim-Colch 5 Crist. Soybean Crist. Soybean 0 Fl . Beggarweed Fl . Beggarweed 100 H. Beggarticks H. Beggarticks 100 Morningglory Morningglory 90 SI. Amaranth SI. Amaranth 100 Southern Sandur Southern Sandur 10 Tr. Spiderwort Tr. Spiderwort 70 Wld Pointsettia Wld Pointsettia 100 W20 Soybean W20 Soybean 5 W4-4 Soybean W4-4 Soybean 5 Table H Table H COMPOUND Rate 4 g/ha Rate 4 g/ha 21 POSTEMERGENCE PREEMERGENCE Acanthospermum Acanthospermum 100 Alexandergrass Alexandergrass 0 Apple-of-Peru Apple-of-Peru 55 Arrowleaf Sida Arrowleaf Sida 0 B. Signalgrass B. Signalgrass 20 Bl. Nightshade Bl. Nightshade 100 Braz Sicklepod Braz Sicklepod 10 Capim-Colch Capim-Colch 0 Crist. Soybean Crist. Soybean 0 Fl. Beggarweed Fl . Beggarweed 100 H. Beggarticks H. Beggarticks 75 Morningglory Morningglory 85 SI. Amaranth SI. Amaranth 100 Southern Sandur Southern Sandur 5 Tr. Spiderwort Tr. Spiderwort 60 Wld Pointsettia Wld Pointsettia 100 W20 Soybean W20 Soybean 5 W4-4 Soybean W4-4 Soybean 5 Table H Rate 2 g/ha POSTEMERGENCE Acanthospermum Alexandergrass Apple-of-Peru Arrowleaf Sida B. Signalgrass Bl . Nightshade Braz Sicklepod Capim-Colch Crist. Soybean Fl. Beggarweed H. Beggarticks Morningglory SI . Amaranth Southern Sandur Tr. Spiderwort Wld Pointsettia W20 Soybean W4-4 Soybean TEST I Compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture and applied to the surface of the water which was contained in each pot. Individual containers of barnyardgrass (Echinochloa oryzicola), small flower umbrella sedge (Cyperus difformus), common falsepimpernel (Lindernia procumbens), monochoria (Monochoria vaginalis) and bulrush (Scirpus juncoides) were seeded and allowed to grow until the 1.5 to 2.5 leaf stage of development. A Sultama clay loam soil was used for this propagation. Japonica rice (Oryza sativa) was transplanted at 0 and 2 cm depth five days before application of the test compound to the water surface. An early and late stage of each weed species was treated, the stage of development being related to the concurrent planting of Scirpus juncoides which was then treated at the 1.5 (early) and the 2.5 (late) leaf stage. Treated plants and untreated controls were maintained under greenhouse conditions for twenty to thirty days at which time treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table I, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash response (-) indicated that no test result was recorded. Table I COMPOUND Table I COMPOUND Rate 250 g/ha 11 13 21 Rate 125 g/ha 11 13 21 Flood Saita soi Flood Saita soi barnyard early barnyard late C. difformis ea C. difformis la Japoni rice Ocm Japoni rice 2cm L. procumben ea L. procumben la M. vaginalis ea M. vaginalis la S. juncoides 1. S. juncoides 2. Table I Rate 64 g/ha Flood Saita soi barnyard early barnyard late C. difformis ea C. difformis la Japoni rice Ocm Japoni rice 2cm L. procumben ea L. procumben la M. vaginalis ea M. vaginalis la S. juncoides 1. S. juncoides 2. TEST J Plastic pots were partially filled with silt loam soil. The soil was then saturated with water. Rice (Oryza sativa) seed or seedlings at the 2.0 to 3.5 leaf stage; seeds, tubers or plant parts selected from barnyardgrass (Echinochloa crus-galli), common waterplantain (Alisma plantago-aquatica), ducksalad (Heteranthera limosa), early watergrass (Echinochloa oryzoides), gooseweed (Sphenoclea zeylanica), junglerice (Echinochloa colonum), late watergrass (Echinochloa oryzicola), monochoria (Monochoria vaginalis), redstem (Ammania species), rice flatsedge (Cyperus iria), ricefield bulrush (Scirpus mucronatus), smallflower flatsedge (Cyperus difformis), tighthead sprangletop (Leptochloa fasicularis) and water-clover (Marsilea quadrifolia) into this soil. Plantings and waterings of these crops and weed species were adjusted to produce plants of appropriate size for the test. At the two leaf stage, water levels were raised to 3 cm above the soil surface and maintained at this level throughout the test. Chemical treatments were formulated in a non-phytotoxic solvent mixture which included a surfactant and applied directly to the paddy water, by pipette, or to the plant foliage, by an air-pressure assisted, calibrated belt-conveyer spray system. Treated plants and controls were maintained in a greenhouse for approximately 21 days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table J, are reported on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Table J COMPOUND Rate 750 g/ha 21 25 39 40 PD/TA barnyardgrass ducksalad 0 60 early watergras gooseweed 90 100 85 85 junglerice late watergrass monochoria 55 60 60 55 redstem 0 0 30 20 rice flatsedge 75 75 80 90 ricefield bulru 60 60 60 35 smallflower fla 0 0 0 30 tighthead spran 0 60 0 40 water-clover 85 20 45 50 A. plantago-aqu 100 100 98 100 2 LF direct see 15 20 10 35 2 LF transp. in 10 15 10 25 Table J COMPOUND Rate 375 g/ha 21 25 39 40 PD/TA barnyardgrass ducksalad 20 early watergras gooseweed 80 45 90 85 junglerice late watergrass monochoria 40 40 25 40 redstem 0 0 0 10 rice flatsedge 35 30 70 15 ricefield bulru 40 15 65 35 smallflower fla 0 0 0 0 tighthead spran 0 0 0 0 water-clover 40 10 20 10 A. plantago-aqu 90 45 100 85 2 LF direct see 15 10 10 20 2 LF transp. in 10 10 10 20 Table J COMPOUND Rate 125 g/ha 12 21 PD/TA barnyardgrass 15 15 ducksalad 80 40 early watergras 45 gooseweed junglerice 40 late watergrass 20 30 monochoria redstem 75 55 rice flatsedge 85 85 ricefield bulru smallflower fla 95 60 tighthead spran 40 45 water-clover A. plantago-aqu 2 LF direct see 20 15 2 LF transp. in 20 0

Claims: CLAIMS What is claimed is: 1. A compound selected from Formula I, N-oxides and agriculturally suitable salts thereof, I wherein X is H. F or Cl; Y is F, Cl, Br, cyano, nitro, C1-C3 haloalkyl, C j ^ alkoxy, C r C 3 haloalkoxy or C(S)ΝH 2 ; R 1 is H, C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C3-C6 haloalkynyl, C 2 -Cg alkoxyalkyl, C -Cg haloalkoxy alkyl, formyl, C 2 -C 2 o alkylcarbonyl, C4-C7 cycloalkylcarbonyl, C 2 -Cg haloalkylcarbonyl, C 2 -Cg alkoxycarbonyl, C3-C6 alkoxyalkylcarbonyl, C 2 -C6 haloalkoxycarbonyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C7 cycloalkylalkyl, C 4 -C 7 halocycloalkylalkyl, S(O) 2 R 2 , C(O)SR 3 , C(O)NR 4 R 5 or benzoyl; R 2 is C r C 6 alkoxy, C r C 6 haloalkoxy, C r C 6 haloalkyl, C 3 -C 6 cylcloalkyl, C 3 -C 6 halocycloalkyl, C 2 -C 6 alkoxyalkyl, C -C 6 haloalkoxyalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 6 alkoxyalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 2 -C 6 cyanoalkyl, C r C 6 nitroalkyl, (CH 2 ) p -OR 6 , CH=CH(CH 2 ) q -OR 6 , C_-C(CH 2 )~-OR 6 , C 2 -C 6 alkylthioalkyl, C 2 -C 6 alkylsulfinylalkyl, C 2 -C 6 alkylsulfonylalkyl, C3-C8 alkoxycarbonylalkyl, C 3 -Cg alkylcarbonyloxyalkyl or oxiranyl optionally substituted with 1-3 CJ-C3 alkyl; R 3 is H, C1-C2 alkyl or C j -C3 haloalkyl; or R 3 is phenyl optionally substituted with C j -C3 alkyl, 1-3 halogen, 4-5 fluorine, 1-2 nitro, C1-C3 alkoxy or CF 3 ; R 4 is H, C1-C3 alkyl or Cj-C3 haloalkyl; or R 4 is phenyl optionally substituted with C1-C3 alkyl, 1-3 halogen, 4-5 fluorine, 1-2 nitro, C1-C3 alkoxy or CF3; R 5 is C r C 3 alkyl or C r C 3 haloalkyl; or R 4 and R 5 are taken together as -CH-CH 2 -, -CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 CH2- or -CH 2 CH 2 OCH 2 CH 2 -; 305 R 6 is C r C 3 alkylsulfonyl, C r C 3 haloalkylsulfonyl or P(=O)(OR 7 )(OR 8 ); or R 6 is phenylsulfonyl optionally substituted with C j -Cg alkyl, 1-3 halogen, 4-5 fluorine, C C^ alkoxy, CF 3 or C 2 -C4 alkylcarbonyl; R 7 and R 8 are each independently H, C j -C3 alkyl or CJ-C3 haloalkyl; J is J-12 306 J-17 J-18 J-19 wherein the dashed line in J-l, J-5, J-6, J-18, and J-19 indicates that the left-hand ring contains only single bonds or one bond in the ring is a carbon-carbon double bond; m and n are each independently 0, 1, 2 or 3, provided that m + n is 2 or 3; alkyl) Z is o, S, S(O), S(O)2, N(C r C 4 alkyl) or Z* is CR9R23, o, S, S(O), each R 9 is independently H, C alkyl, halogen, hydroxy, C j -Cg alkoxy, C C 6 haloalkyl, C j -Cg haloalkoxy, C -C alkylcarbonyloxy or C -Cg haloalkylcarbonyloxy; each R 10 is independently H, C j -Cg alkyl, hydroxy or halogen; or when R 9 and R 10 are bonded to adjacent carbon atoms they can be taken together CH 2 JP A QI with the carbons to which they are attached to form optionally substituted with at least one member selected from 1-2 halogen and 1-2 C r C 3 alkyl; each R 1 is independently H, C Cg alkyl, C2~C 6 alkenyl, C j -Cg haloalkyl or C 2 -Cg alkoxyalkyl; Rl 2 is H, halogen, C r C 6 alkyl, C 3 -C 6 alkenyl, C r C 6 haloalkyl or C 2 -C 6 alkoxyalkyl; Rl 3 is H, C 1 -C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -Cg haloalkynyl, HC(=O), C 2 -C 5 alkylcarbonyl or N(R π ) 2 ; Rl 4 is C r C 6 alkyl, C r C 6 alkylthio, C r C 6 haloalkyl or N(CH 3 ) 2 ; W is N or CR 15 ; R 15 is H, C Cg alkyl or halogen; or R 15 is phenyl optionally substituted with Ci-Cg alkyl, 1-3 halogen, 4-5 fluorine, C Cg alkoxy or CF3; R 16 is C r C 6 alkyl, halogen or C r C 6 haloalkyl; R and R !8 are each independently H, C r C 6 alkyl or C r C 6 haloalkyl; Rl9 and R 20 are each independently C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -Cg haloalkenyl, C3-C alkynyl or C 3 -Cg haloalkynyl; R 2] is H, halogen, cyano, C1-C3 alkoxy or C1-C3 haloalkoxy; R 22 is Cj-Cg alkyl or Cj-Cg haloalkyl; or R 22 is phenyl optionally substituted with Cj-C alkyl, 1-3 halogen, 4-5 fluorine, 1-2 nitro, C j -Cg alkoxy or CF 3 ; R 23 is C1-C3 alkyl, hydroxy or halogen; R 24 is cyano or C(Q)R 25 ; R 25 is OR 26 or NR 27 R 28 ; R 26 is C r C 6 alkyl or C r C 6 haloalkyl; each R 27 is independently H or C j -Cg alkyl; R 28 is H, C r C 6 alkyl, C r C 6 alkoxy or NR 27 R 29 ; or R 27 and R 28 can be taken together as -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 CH 2 - or -CH 2 CH 2 OCH 2 CH 2 -; R 29 is H, C r C 3 alkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 alkoxycarbonyl or C r C 3 alkylsulfonyl; Q is independently O or S; Ql is O or S; p is 1, 2 or 3; and q is O, 1, 2 or 3; provided that, (a) when J is J-5, X is F, Y is Cl, R* is H, Q is O, R 9 and Rl° are H, Z 1 is O, n is 2, and m is 1, then R 2 is other than CF 3 ; (b) when J is J-6, X is F, Y is Cl, R l is H, Q is O, R 9 and R l ° are H, Z is CHCl or CHBr, n is 1, and m is 1, then R 2 is other than CF3; (c) when J is J-8, X is F, Y is Cl, Rl is H, R and R !8 are H, Q is O, R 9 and Rl° are H, Z is CH 2 , and (m+n) is 2 or 3, then R 2 is other than CF 3 ; (d) when J is J-8, X is F, Y is Cl, Rl is H, R 17 and R 18 are H, Q is O, R 9 and Rl° are H, Z is O, n is 1, and m is 2, then R 2 is other than CF 3 ; and (e) when J is J- 11 , X is F, Y is Cl, Rl is H, R 2i is Cl, R 9 and Rl° are H, Z , is CH 2 , and (m+n) is 3, then R 2 is other than CF3. 2. A compound of Claim 1 wherein: X is F or Cl; Y is F. Cl orBr; R 1 is H, C r C 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C r C 6 haloalkyl, C 2 -C 6 alkoxyalkyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkoxyalkylcarbonyl, C 2 -Cg alkylcarbonyl, C -Cg alkoxycarbonyl, S(O) 2 R 2 or C(O)NR 4 R 5 ; R 2 is C r C 6 alkoxy, C r C 6 haloalkoxy, C r C 6 haloalkyl, C 3 -C 6 cylcloalkyl, C 3 -Cg halocycloalkyl, C 2 -C 6 alkoxyalkyl or C 2 -C 6 haloalkoxy alkyl; J is J-5, J-6, J-l l, J-17 or J-19; Z is CR 9 Ri°, O, S or N(C r C 4 alkyl); each R 9 is independently H, halogen or C j -Cg haloalkoxy; each Rl° is independently H, hydroxy or halogen; each Q is O; Zl is CR9R 23 , O, S or N(C r C 4 alkyl); and R 23 is halogen. 3. A compound of Claim 2 wherein: Y is F or Cl; Rl is H, C r C 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C r C 6 haloalkyl, C 2 -C 6 alkoxyalkyl, C 3 -C 6 haloalkenyl, C 2 -C 6 alkylcarbonyl or C 2 -Cg alkoxycarbonyl; R 2 is C r Cg haloalkoxy, C r C 6 haloalkyl, C 3 -C 6 halocycloalkyl, C 2 -C 6 alkoxyalkyl or C 2 -Cg haloalkoxyalkyl; Z is CR 9 Rl0 O r O; and Z is CR 9 R 23 or O. 4. A compound of Claim 2 wherein: J is J-19; Rl is H, C r C 6 alkyl, C 3 -C 6 alkenyl, C 3 -Cg alkynyl, C 2 -C 6 alkoxyalkyl, C 2 -Cg alkylcarbonyl or C 2 -Cg alkoxycarbonyl; R 2 is C j -Cg haloalkyl; R9 is H; Rl° is hydroxy or halogen; Z is CR 9 Rl°; n is 1; and m is 1. 5. A compound of Claim 3 wherein: J is J-6; and Z is CR 9 Rl°. 6. The compound of Claim 5 which is selected from the group: a) (6S-cw)-l-chloro-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro-l,3-dioxo-lH- ρyrrolo[ 1 ,2-c]imidazol-2(3H)-yl)phenyl]methanesulfona_nide; b) (65-ci_)-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro- 1 ,3-dioxo- 1H- pyrrolo[ 1 ,2-c]imidazol-2(3H)-yl)phenyl]-N- [(chloromethyl)sulfonyl]acetamide; c) (6S-c is)- 1 -chloro-N-[2-chloro-5-(6-chlorotetrahydro- 1 ,3-dioxo- 1 H- pyrrolo[ 1 ,2-c]imidazol-2(3H)-yl)-4-fluorophenyl]methanesulfonamide; d) (65-cw)-N-[2-chloro-5-(6-chlorotetrahydro- 1 ,3-dioxo- lH-pyrrolo[ 1 ,2- c]i_mda_:ol-2(3--)-yl)-4-fluorophenyl)-N-[(cUoromemyl)sulfonyl]acetarriide; e) (6S-c _ , )-l-chloro-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro-l,3-dioxo-lH- pyrrolof 1 ,2-c]imidazol-2(3H)-yl)phenyl]methanesulfonamide monosodium salt; f) (6S-cis)- 1 -chloro-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro- 1 ,3-dioxo- 1H- pyrrolof 1 ,2-c]imidazol-2(3--)-yl)phenyl]meΛanesulfonamide monopotassium salt; g) (6S-cis)- l-chloro-N-[2-chloro-5-(6-chlorotetrahydro- 1 ,3-dioxo- 1H- pyrτolo[ 1 ,2-c]inιidazol-2(3H)-yl)-4-fluorophenyl]methanesulfonamide monosodium salt; and h) (6S-cis )- 1 -chloro-N-[2-chloro-5-(6-chlorotetrahydro- 1 ,3-dioxo- 1H- pyrrolo [ 1 ,2-c] iidazol-2(3H)-yl)-4-fluorophenyl]methanesulfonamide monopotassium salt. 7. A mixture comprising a herbicidally effective amount of a compound of Claim 6 with a herbicidally effective amount of one or more compounds selected from rimsulfuron, thifensulfuron-methyl, chlorimuron-ethyl, nicosulfuron, prosulfuron, primsulfuron, atrazine, terbuthylazine, dicamba, 2,4-D, bomoxynil, pyridate, sulcotrione, glufosinate, glyphosate, glyphosate-trimesium, fluthiacet-methyl, quizalofop-p-ethyl, bentazone, clopyralid, flumetsulam, halosulfuron, sethoxydim, flumiclorac-pentyl, imozamox, acetachlor, alachlor, dimethenamid, isoxaflutole, metolachlor, metribuzin, pendimethalin, thiafluimid, clethodim, fluazifop-p-butyl, haloxyfop, imazethapyr, imazaquin, lactofen, acifluorfen-sodium, oxasulfuron, imazameth, tribenuron-methyl, metsulfuron-methyl, chlorsulfuron, triasulfuron, bromoxynil, MCPA, fluroxypyr, fenoxaprop, fenchlorazole, diclofop, tralkoxydim, clodinafop, cloquintocet-mexyl, imazamethabenz, sulfosulfuron, difenzoquat, propanil, triallate, trifluralin, paraquat, diallate, linuron, diflufenican, cyanazine, neburon, terbutryn, prosulfocarb, isoproturon, chlortoluron, methabenzthiazuron, metoxuron, simazine, ioxynil, mecoprop, metosulam, fluroglycophen-ethyl, flamprop-M-isopropyl, and benzoylpropethyl. 8. A herbicidal composition comprising a herbicidally effective amount of a compound of Claim 1 and at least one of a surfactant, a solid diluent or a liquid diluent. 9. A herbicidal composition comprising a herbicidally effective amount of a mixture of Claim 7 and at least one of a surfactant, a solid diluent or a liquid diluent. 10. 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. 11. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a mixture of Claim 7.

Inventors: ADAMS EDWARD JOHN, DRAUZ KARLHEINZ, HONG WONPYO, KAMIREDDY BALREDDY, PETERSEN WALLACE CHRISTIAN, SCHAFER MATTHIAS, WECKBECKER CHRISTOPH, ADAMS, EDWARD, JOHN, DRAUZ, KARLHEINZ, HONG, WONPYO, KAMIREDDY, BALREDDY, PETERSEN, WALLACE, CHRISTIAN, SCHAFER, MATTHIAS, WECKBECKER, CHRISTOPH
Applicants: ADAMS EDWARD JOHN, DRAUZ KARLHEINZ, DU PONT, HONG WONPYO, KAMIREDDY BALREDDY, PETERSEN WALLACE CHRISTIAN, SCHAFER MATTHIAS, WECKBECKER CHRISTOPH, ADAMS, EDWARD, JOHN, DRAUZ, KARLHEINZ, E.I. DU PONT DE NEMOURS AND COMPANY, HONG, WONPYO, KAMIREDDY, BALREDDY, PETERSEN, WALLACE, CHRISTIAN, SCHAFER, MATTHIAS, WECKBECKER, CHRISTOPH
Application year: 1996
Main classification: C07D487
IPC codes: A01N41, A01N43, A01N47, C07D207, C07D209, C07D231, C07D239, C07D251, C07D261, C07D263, C07D271, C07D471, C07D487