Patent CA-1225642-A (CA)
Inventor: DUMAS DONALD J
IPC: C07D249/12
Filed: 1985-06-04
Granted: 1987-08-18
Abstract: Title             BA-8578A                 HERBICIDAL SULFONAMIDES               Abstract of the Disclosure This invention relates to certain sulfonylurea compounds having an ester group ortho to the sulfonyl-urea linkage which have been found to be excellent preemergent and postemergent herbicides or plant growth regulators.  More specifically the compounds are of the formula:                               I wherein  ,       ,      ,       ,            or    ;     W is O or S;    R is H or CH3;    R1 is C2-C5 alkyl, C4 alkenyl or C4 alkynyl substituted with one or two substituents selected from:        -OH, SH,  , ,  ,  ,  ,  ,  ,  ,  ,  ,  , -OSO2R17, -OSO2NR8R17, -OSi(R9)2R10, -S(O)nR7, -NR7R8, -OCF2H, -OCH2CH2F or  ;   provided that 1)  when R1 is disubstituted, then the two substituents are identical and are not on the same carbon atom; 2) when R1 is C2-C3 alkyl and monosubstituted, then the substituent is other than -SR7 or -SO2R7; and 3)  the carbon atom of R1 adjacent to the ester oxygen does not carry any of the above substituents and must be substituted by at least one hydrogen atom;       W1 is O or S; n is 0, 1, or 2;       R2 is H, Cl, F, Br, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 alkylthio, C1-C3 haloalkoxy, C1-C3 haloalkylthio, C1-C2 haloalkyl, or C1-C2 alkyl substituted with OCH3 or SCH3;       R3 is H, F, Cl, CH3 or OCH3;       R4 is H or CH3;       R5 is H, C1-C3 alkyl, CH2CH=CH2 or phenyl;     R6 is H or C1-C3 alkyl:  R7 is C1-C4 alkyl substituted with 0-3 atoms of F, Cl or Br, 0-2 methoxy groups or 0-1 cyano groups, C3-C4 alkenyl substituted with 0-3 atoms of F, Cl or Br, C3-C4 alkynyl or   R8 is H or C1-C2 alkyl;          R9 is C1-C2 alkyl;          R10 is  C1-C4 alkyl or C6H5;          R11 and R12 are independently H, F, Cl, Br, CH3, OCH3, SCH3, SO2CH3, NO2 or CF3;     A is  ,  ,    ,  ,  ,     , or     ;      X is CH3, OCH3, OCH2CH3, Cl, F, Br, OCF2H, CH2F, OCH2CH2F, OCH2CHF2, OCH2CF3 or CF3;    Y  is H, CH3, OCH3, OC2H5, CH2OCH3, NHCH3, N(OCH3)CH3, NH2, N(CH3)2, C2H5, CF3, SCH3, OCH2CH=CH2, OCH2C?CH, OCH2CH2OCH3,  ,    ,   ,   ,   OCF2H, SCF2H, CH2S(O)p(C1-C4 alkyl), cyclopropyl or CH2OC2H5;   m is 2 or 3; p is 0. 1 or 2:     Q1 and Q2 are independently O or S;     R13 is H or CH3;     R14 and R15 are independently C1-C2 alkyl;     R16 is H, F, Cl or CH3;     R17 is C1-C10 alkyl substituted with 0-3 atoms of F, Cl or Br, 0-2 methoxy groups or 0-1 cyano groups, C3-C10 alkenyl substituted with 0-3 atoms of F, Cl or Br, C3-C10 alkynyl substi-tuted with 0-3 atoms of F, Cl or Br, or  ;       Z is CH or N;     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;     Y3 is H or CH3;     X3 is CH3 or OCH3;     X4 is CH3, OCH3, OC2H5, CH2OCH3 or Cl; and Y4 is CH3, OCH3, OC2H5 or Cl; provided that a) when W is S, then R is H, A is   ,  and Y is CH3, OCH3, OC2H5, CH2OCH3, C2H5,  CF3, SCH3, OCH2CH=CH2, OCH2C?CH, OCH2CF3, OCH2CH2OCH3, CH(OCH3)2 or   b) when X is Cl, F or Br, then Z is CH and Y is OCH3, OC2H5, NH2,  N(OCH3)CH3, NHCH3, N(CH3)2 or OCF2H; and c) when X or Y is OCF2H, then Z is CH; and their agriculturally suitable salts.