Herbicidal sulfonamides

Details Herbicidal sulfonamides Herbicidal sulfonamides

C - Chemistry, Metallurgy

07

D

260/251, 260/249

C07D 403/12 (2006.01) A01N 47/36 (2006.01) C07D 231/14 (2006.01) C07D 307/88 (2006.01) C07D 409/12 (2006.01) C07D 521/00 (2006.01)

Patent

CA 1221693

Title HERBICIDAL SULFONAMIDES Abstract of the Disclosure Pyrazole sulfonylureas are useful as pre- and post- emergence herbicides. Typical of this group is 3-[[(4,6- dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyylmethyl]- 1,5-dimethyl-1H-pyrazole-4-carboxylic acid, ethyl ester. Compounds of the invention are of the following formula: Image wherein Image J-1 J-2 J-3 Image J-4 J-5 J-6 Image J-7 J-8 J-9 Image J-10 J-11 R is H or CH3; R1 is H. C1-C3 LKYL, CO2R15, SO2NR16R17 or SO2R18; R2 is H or CH3; R3 is H or CH3; R4 is H or CH3; R5 is H, CH3, C1, Br, CO2R15, C(O)NR16Rl7, SO2NRl6R17,SO2N(OCH3)CH3, SO2R18 or NO2; R6 is H, C1-C3 alkyl. CO2R15. SO2NR16R17 or SO2R18; R7 is H or CH3; R8 is CO2R15, C(O)NR16R17, SO2NR16R17, SO2N(OCH3)CH3, SO2R18 or NO2; R9 is H, C1-C3 alkyl or phenyl; R10 is CO2R15. C(O)NR16R17, SO2NR16R17, SO2N(OCH3)CH3, SO2R18 or NO2; Rll is H or CH3; R12 is H, CO2R15, C(O)NR16R17, SO2NR16R17, SO2N(OCH3)CH3, SO2R18 or NO2; R13 is H. CO2R15, C(O)NR16R17, SO2NR16R17, SO2N(OCH3)CH3, SO2R18 or NO2; R14 is H or CH3; R15 is C1-C2 alkyl; R16 is H or C1-C2 alkyl; R17 is H or C1-C2 alkyl; R18 is C1-C2 alkyl; R19 is H. CH3, C1. Br, NO2, C1-C2 alkylthio or C1-C2 alkylsulfonyl; Image A-1 A-2 A-3 A-4 Image A-5 A-6 X is CH3, OCH3. Cl, Br. OCH2CF3 or OCHF2: Y is C1-C3 alkyl, CH2F, cyclopropyl, C?CH. OCH3, OC2H5, CH2OCH3, NH2. NHCH3, N(CH)2, OCH2CH2F, CF3, SCH3, OCH2CH=CH2, OCH2C?CH, OCH2CH20CH3, CR(OCH3)2, Image CR(OCH2CH3)2 or OCF2H: Z is CH or N: X1 is CH3, OCH3, OC2H5, or OCF2H; Y1 is O or CH2; X2 is CH3, C2H5 or CH2CF3; Y2 is OCH3, OC2H5, SCH3, SC2H5, SCH3 OCF2H, SCF2H, CH3 or CH2CH3; X3 is CH3 or OCH3; Y3 is H or CH3; provided that 1) when X is Cl or Br, then Z is CH and Y is OCH3, OC2H5, NHCH3, N(CH3)2 or OCF2H; 2) R5 and R6 are not simultaneous1y H; 3) when R6 is other than H or C1-C3 alkyl, then R5 must be H; 4) R12 and R13 are not simultaneous1y H; 5) when R12 is other than H, then R13 must be H; and 6) when X or Y is OCF2H, then Z is CH. 7) R5 and R19 are not simultaneously H; and 8) when J is J-8 or J-ll then R5 is other than H.

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