Herbicidal sulfonamides

Details Herbicidal sulfonamides Herbicidal sulfonamides

C - Chemistry, Metallurgy

07

D

260/249, 260/251

C07D 409/12 (2006.01) A01N 47/36 (2006.01) C07D 333/54 (2006.01) C07D 335/06 (2006.01) C07D 521/00 (2006.01) C07F 7/08 (2006.01) C07F 7/10 (2006.01)

Patent

CA 1234812

Title BA-8639A HERBICIDAL SULFONAMIDES Abstract of the Disclosure This invention relates to herbicidally active sulfonylurea compounds, agriculturally suitable composi- tions thereof and their method of use as herbicides or plant growth regulants. The sulfonylurea compounds are of the formula: Image I wherein J is Image , Image , Image , J-1 J-2 J-3 Image , Image , Image , J-4 J-5 J-6 Image , Image , Image , J-7 J-8 J-9 Image J-10 J-11 J-12 or Image ; J-13 n is 0 or 1; W is O or S; Q is O, S, SO or SO2: R is H or CH3: R1 is H or CH3; R2 is H or C1-C3 alkyl; R3 is H or CH3: R4 is C3-C6 cycloalkyl, C5-C6 cycloalkenyl. Image , Si(CH3)2(C1-C4 alkyl). Si(CH3)2(C2-C4 alkenyl), Si(CH3)2(C1-C3 alkoxy), Image , P(O)(CH3)2. P(O)(OCH3)2, CN, C1-C4 alkylcarbonyl, C3-C4 cycloalkylcarbonyl, NR9R10 or C1-C2 alkyl sub- stituted with C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C2-C3 alkenyloxy, C2-C3 haloalkenyloxy, C1-C3 alkylthio, C1-C3 halo- alkylthio, C1-C3 alkylsulfinyl. C1-C3 alkyl- sulfonyl, C1-C3 haloalkylsulfinyl, C1-C3 halo- alkylsulfonyl. Si(CH3)2(C1-C4 alkyl), NO2. CN, C1-C2 alkylcarbonyl, OH, NR9R10. CO2(C1-C3 alkyl). SCN, P(O)(OCH3)2 or SO2NR11R12: R5 is H or C1-C2 alkyl; R6 is H or CH3: R7 is H or CH3; R8 is H, F, Cl, Br, CH3, OCH3 or SCH3; Rg is H or C1-C3 alkyl; R10 is H or C1-C3 alkyl; or R9 and R10 may be taken together to form (CH2)4, (CH2)5 or CH2CH2OCH2CH2; R11 and R12 are independently H or C1-C3 alkyl: R13 is H, C1-C3 alkyl, Cl or Br: R14 is H, CH3, Cl or Br; A is Image , Image , Image , A-1 A-2 A-3 Image , Image , Image , A-4 A-5 A-6 or Image ; A-7 X is H, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 halo- alkoxy, C1-C4 haloalkyl, C1-C4 haloalkylthio, C1-C4 alkylthio, halogen, C2-C5 alkoxyalkyl. C2-C5 alkoxyalkoxy, amino. C1-C3 alkylamino. di(C1-C3 alkyl)amino or C3-C5 cycloalkyl; Y is H, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 halo- alkoxy, C1-C4 haloalkylthio, C1-C4 alkylthio. C2-C5 alkoxyalkyl, C2-C5 alkoxyalkoxy, amino. C1-C3 alkylamino, di(C1-C3 alkyl)amino, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C2-C5 alkylthio- alkyl, C2-C5 alkylsulfinylalkyl, C2-C5 alkyl- sulfonylalkyl, C1-C4 haloalkyl, C2-C4 alkynyl, azido, cyano, ?Ra, Image , Image or N(OCH3)CH3; m is 2 or 3; Q1 and Q2 are independently O or S; Ra is H or C1-C3 alkyl; Rb and Rc are independently C1-C3 alkyl; Z is CH, N, CCH3, CC2H5, CCl or CBr: Y1 is O or CH2; X1 is CH3, OCH3, OC2H5 or OCF2H; X2 is CH3, C2H5 or CH2CF3; Y2 is OCH3, OC2H5, SCH3, SC2H5, CH3 or CH2CH3; X3 is CH3 or OCH3; Y3 is H or CH3: X4 is CH3, OCH3, OC2H5, CH2OCH3 or Cl; Y4 is CH3, OCH3, OC2H5 or Cl; and Z1 is CH or N; and their agriculturally suitable salts; provided that a) when X is Cl, F, Br or I, then Z is CH and Y is OCH3, OC2H5, N(OCH3)CH3, NHCH3, N(CH3)2 or OCF2H; and b) when X or Y is C1 haloalkoxy, then Z is CH; c) when W is S, then R is H, A is A-1, Z is CH or N, and Y is CH3, OCH3, OC2H5, CH2OCH3, C2H5, CF3, SCH3, OCH2CH=CH2, OCH2C?CH, OCH2CH2OCH3, CH(OCH3)2 or Image ; d) when R1 is CH3, then n is O; e) when J is J-6, then R1 and R2 are not both H; f) when the total number of carbons of X and Y is greater than four, then the number of carbons of R4 must be less than or equal to three; g) X4 and Y4 may not simultaneously be Cl; and h) when J is J-12, then R4 is other than C1-C4 alkylcarbonyl.

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