Patent CA-1230334-A (CA)
Inventor: PASTERIS ROBERT J
IPC: C07D231/54
Filed: 1986-03-06
Granted: 1987-12-15
Abstract: Title             BA-8619A HERBICIDAL SULFONAMIDES Abstract of the Disclosure Benzenesulfonamide compounds having the following formula, and having herbicidal utility, are disclosed:                         wherein W is O or s:      Q is     G is CH2 , CH2CH2, O, S, NH, NCH3 or CH=CH; G1 is CH2, CH2CH2 or CH=CH; J is CH2, C=O, S(O)m, O, NH, NCH3, CHOH, CHOCH3, CH(CH3) or C(CH3)OH;    J1 is CH2, C=O or SO2; n and n1 are independently 0 or 1; m is 0, 1 or 2; E is a bridge of 3 or 4 atoms containing 0 to 2 heteroatoms selected from the group consisting of oxygen, sulfur or nitrogen, wherein 1 atom of sulfur may take the form of SO or SO2, said bridge also containing 1 to 4 atoms of carbon wherein 1 atom of carbon may take the form of C=O, said bridge together with two attachment sites forming a non-aromatic heterocyclic or carbocyclic ring optionally substituted by 1 to 3 substituent groups selected from the group L, or E is a bridge of 3 or 4 atoms containing 0-1 heteroatoms of oxygen or sulfur and 0-3 heteroatoms of nigrogen, said bridge also containing 0-4 atoms of carbon, said bridge together with two attachment sites forming an aromatic heterocyclic or carbocyclic ring optionally substituted by 1 to 3 substituents selected from the group L, with the proviso that when E contains two oxygen atoms or two sulfur atoms said atoms must be separated by at least one atom of carbon and that oxygen and sulfur are only linked to each other if the sulfur is in the form of SO or SO2; L is C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C8 alkoxyalkoxy, halogen, N(CH3)2, cyano, nitro, phenyl or phenyl sub-stituted with C1-C3 alkyl, C1-C3 haloalkyl, halogen, NO2, C1-C3 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl or C1-C3 alkylsulfonyl; R is H or CH3; R1 is H, C1-C3 alkyl, C1-C3 haloalkyl, halogen, nitro, C1-C3 alkoxy, SO2NRIRII, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, CO2RIII or NRaRb;       RI is H, C1-C4 alkyl, C2-C3 cyanoalkyl, methoxy or ethoxy; RII is H, C1-C4 alkyl or C3-C4 alkenyl; or RI and RII may be taken together as -(CH2)3-, -(CH2)4-, -(CH2)5- or -CH2CH2OCH2CH2-; RIII is C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, C2-C4 haloalkyl, C1-C3 cyanoalkyl, C5-C6 cyclo-alkyl, C4-C7 cycloalkylalkyl or C2-C4 alkoxy-alkyl;     Ra and Rb are independently H or C1-C2 alkyl;     A is         X is H, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 haloalkyl, C1-C4 haloalkylthio, C1-C4 alkyl-thio, halogen, C2-C5 alkoxyalkyl, C2-C5 alkoxy-alkoxy, amino, C1-C3 alkylamino or di(C1-C3 alkyl)amino; Y is H, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, 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, C1-C4 haloalkyl, C3-C5 cycloalkyl, C2-C4 alkynyl, N(OCH3)CH3,   or      ; p is 2 or 3; L1 and L2 are independently O or S; R2 and R3 are independently C1-C2 alkyl;     R4 is H or CH3; Z is CH or N; Y1 is O or CH2; X1 is CH3, OCH3, OC2H5 or OCF2H;   Y2 is H or CH3; X2 is CH3, OCH3 or SCH3; Y3 is CH3, CH2CH3 or CH2CF3;   X3 is CH3 or OCH3; X4 is CH3, OCH3, OC2H5, CH2OCH3 or C1; and Y4 is CH3, OCH3, OC2H5 or C1; and their agriculturally suitable salts; provided that a) when X is C1, F, Br or I, then Z is CH and Y is OCH3, OC2H5, N(OCH3)CH3, NHCH3, N(CH3)2 or OCF2H; b) when X or Y is OCF2H, then Z is CH; c) n and n1 cannot simultaneously be O; d) when G or G1 is CH2CH2 or CH=CH, then n is O; e) when Q is Q1 and n is 1, then E must contain at least one heteroatom selected from oxygen, sulfur or nitrogen; and f) when W is S, then A is A-1, R is H, and Y is CH3, OCH3, OC2H5, CH2OCH3, C2H5, CF3, SCH3, OCH2CH=CH2, OCH2C?CH, OCH2CH2OCH3, CH(OCH3)2 or    .           Examples of such compounds are N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-1,4-dihydro-3-methyl-4-oxo-1-phenyl-indeno[1,2-C]-pyrazole-5-sulfonamide and N-[1,4-dihydro-3-methyl-4-oxo-1-phenyl-indeno[1,2-C]pyrazole-5-sulfonamide.