C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/259, 260/249
C07D 239/28 (2006.01) A01N 47/36 (2006.01) C07D 251/12 (2006.01) C07D 521/00 (2006.01)
Patent
CA 1225642
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: Image I wherein Image , Image , Image J-1 J-2 J-3 Image , Image , Image J-4 J-5 J-6 Image or Image ; J-7 J-8 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, Image , Image , Image , Image , Image , Image , Image , Image , Image , Image , Image , -OSO2R17, -OSO2NR8R17, -OSi(R9)2R10, -S(O)nR7, -NR7R8, -OCF2H, -OCH2CH2F or Image ; 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 Image 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 Image , Image , Image , Image , A-1 A-2 A-3 A-4 Image , Image , or Image ; A-5 A-6 A-7 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, Image , Image , Image , Image , 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 Image ; 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 Image , and Y is CH3, OCH3, OC2H5, CH2OCH3, C2H5, CF3, SCH3, OCH2CH=CH2, OCH2C?CH, OCH2CF3, OCH2CH2OCH3, CH(OCH3)2 or Image 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.
483127
E. I. Du Pont de Nemours And Company
Mccallum Brooks & Co.
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