Patent CA-1231336-A (CA)
Inventor: LEVITT GEORGE
IPC: C07D409/14
Filed: 1986-05-22
Granted: 1988-01-12
Abstract: Title HERBICIDAL o-CARBOMETHOXYSULFONYLUREAS             Abstract of the Disclosure Tetrazole-substituted benezenesulfonamides are useful as agricultural chemicals and, in particular, as growth regulants and herbicides.  The benzenesulfonamides are of the formula:             wherein J is              W is O or S:    G is O, S, SO or SO2: m is O or 1; n is O, 1 or 2;    R is H or CH3:    E is a single bond, CH2 or O:     Q is                       R1 is H, C1-C3 alkyl. C1-C3 haloalkyl, halogen, nitro, C1-C3 alkoxy, SO2NRaRb, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, CN, CO2Rc, C1-C3 haloalkoxy, C1-C3 haloalkylthio. amino, C1-C3 alkylamino, di(C1-C3 alkyl)amino or C1-C2 alkyl substituted with C1-C2 alkoxy, C1-C2 haloalkoxy. C1-C2 alkylthio, C1-C2 halo-alkylthio or CN;       R2 is H, C1-C3 alkyl, allyl or phenyl;       R3 is H, C1-C6 alkyl, C3-Cs cycloalkyl, C1-C6 halo-alkyl, CH2- (C2-C5 alkenyl), CH2 (C2-C5 halo-alkenyl), CH2-C2-C5 alkynyl), CH2(C2- C5 halo-alkynyl), C6H5 or C1-C4 alkyl substituted with C1-C2 alkoxy, C1-C2 alkylthio, C1-C2 alkyl-sulfinyl or C1-C2 alkylsulfonyl;    R4 is H. halogen. C1-CS alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 halo-alkenyl, C2-C6 alkynyl, C3-C6 haloalkynyl, C6H5, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, OCH2CH2O-(C1-C2 alkyl) or di(C1-C3 alkyl)amino;       R5 i6 H, C1-C3 alkyl or allyl;     Ra is H, C1-C4 alkyl, C2-C3 cyanoalkyl, methoxy or ethoxy;          Rb is H,C1-C4 alkyl or C3-C4 alkenyl: or Ra and Rb may be taken together as -(CH2)3-, -(CHz)4-, -(CH2)5- or -CH2CH2OCH2CH2-;   Rc is C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, C2-C4 haloalkyl, C1-C2 cyanoalkyl, C5-C6 cyclo-alkyl, C4-C7 cycloalkylalkyl or C2-C4 alkoxyalkyl;     A is                or          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 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, C2-C4 haloalkyl, C2-C4 alkynyl, azido, cyano,           or -N(OCH3)CH3;      P is 2 or 3;    L1 and L2 are independently O or S;    R6 is H or CH3;    R7 and R8 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, SCH, SC2H5, CH3 or  CH2CH3;    X3 is CH3 or OCH3;    Y3 is H or CH3;    X4 is CH3, OCH3, OC2H5, or 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; b) when X or Y is C1 haloalkoxy, then Z is CH;     c) when J is J-2, J-3 or J-4, the substituent Gm(CH2)nQ or (CH2)nQ and the sulfonylurea bridge are on adjacent ring positions; d) when J is J-4 and n is O, then Q is Q-1 or Q-2; e) when E is O, then J is J-1; 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     g) when the total number of carbon atoms in X and Y is greater than 4, then the carbon content of R1, R3, R4 and R5 must each be less than or equal to 2; h) X4 and Y4 cannot simultaneously be Cl; i) when J is J-1 and m is 0, then n is 0; and j) when n is 0 and m is 1, then Q is Q-1 or Q-2,