HERBICIDAL SULFONAMIDES

摘要

Title HERBICIDAL SULFONAMIDES This invention relates to certain sulfonylurea compounds having substitutents ortho to the sulfonylurea linkage that include 3- or 4-membered carbocyclic rings, saturated 5- or 6- membered carbocyclic rings, heterocyclic rings which contain 1 heteroatom selected from O, S, and NR3, alkenes, substituted alkenes, cycloalkenes, substituted cycloalkenes, alkynes, and substituted alkynes, agriculturally suitable compositions thereof and a method of their use as herbicides or plant growth requlants. More specifically, the compounds are of compounds are of the formula: < IMG > I wherein < IMG > < IMG > L-1 L-2 < IMG > < IMG > L-3 L-4 < IMG > < IMG > L-5 L-6 < IMG > L-7 < IMG > L-8 L-9 < IMG > L-10 L-11 < IMG > L-12 L-13 R is H or CH3; W3 is O or S, n is 0 or 1: E is S(O)p or Se; p is 0, 1 or 2; R1 is H, C1-C3 alkyl, C1-C3 haloalkyl, halogen, nitro, CH2CN, CH2OCH3, CH2SCH3, CN, C1-C3 alkoxy, SO2NRIRII, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl or CO2RIII; 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, C2-C3 cyanoalkyl, C5-C6 cycloalkyl, C4-C7 cycloalkylalkyl or C2-C4 alkoxyalkyl; R2 is C1-C3 alkyl; W is W1 or W2; W1 is C2-C8 alkenyl or C4-C7 cycloalkenyl either of which may be optionally substituted with 1-3 atoms of F, Cl or Br, OH, CN, NO2, C1-C3 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, amino, C2-C4 alkenyl, C1-C3 alkylamino, di(C1-C3 alkyl)amino, (C1-C3 alkylamino)sulfamoyl, di(C1-C3 alkylamino)sulfamoyl, OC(O)C1-C3 alkyl, OC(O)C1-C3 alkoxy, OSO2C1-C3 alkyl, OSO2C6H5, OSO2-4-CH3-C6H4, phenyl or phenyl substituted with halogen, CH3, OCH3, SCH3 or NO2; W2 is C2 alkynyl which may be substituted with phenyl or phenyl substituted with halogen, CH3, OCH3, SCH3 or NO2 or W2 is C3-C8 alkynyl which may be optionally substituted with 1-3 atoms of F, Cl or Br, OH, CN, NO2, C1-C3 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, amino, C1-C3 alkylamino, di(C1-C3 alkyl)amino, (C1-C3 alkylamino)sulfamoyl, di(C1-C3 alkylamino)sulfamoyl, OC(O)C1-C3 alkyl, OC(O)C1-C3 alkoxy- OSO2C1-C3 alkyl- OSO2C6H5, OSO2-4-CH3-C6H4, phenyl or phenyl substituted with halogen, CH3, OCH3, SCH3 or NO2; Q is a 3- or 4-membered heterocyclic ring which contains one heteroatom selected from O, S and NR3, or a 3- or 4-membered carbocyclic ring in which one carbon atom may optionally be in the form of a carbonyl group, or a fully-saturated 5- or 6-membered carbocyclic ring, and Q may be optionally substituted with 1-4 substituents selected from halogen, CN, OH, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 alkylthio, C2-C3 alkoxycarbonyl, C1-C4 alkylsulfonyl, (C1-C4 alkyl)aminosulfamoyl and di(C1-C4 alkyl)aminosulfamoyl; R3 is C1-C4 alkyl: R12 is H or OR14: R13 is H or C1-C4 alkyl; R14 is H, C1-C4 alkyl, C3-C4 alkenyl. C3-C4 halo alkenyl, C3-C4 alkynyl, C3-C4 haloalkynyl, C2-C4 alkylcarbonyl, C(O)NR15R16, C1-C4 alkylsulfonyl, C2-C4 alkoxyalkyl or C2-C4 alkylthioalkyl: R15 and R16 are independently H or C1-C2 alkyl: R17 is H or C1-C4 alkyl: A is < IMG > < IMG > < IMG > A-1 A-2 A-3 < IMG > < IMG > < IMG > A-4 A-5 A-6 < IMG > A-7 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 or di(C1-C3 alkyl)amino; Y is H, C1-C4 alkyl, C1-C4 alkoxy. C1-C4 halo 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 alkylthioalkyl, C1-C4 haloalkyl, C3-C5 cycloalkyl, C2-C4 alkynyl, ?R6, < IMG >, < IMG >, < IMG > or N(OCH3)CH3; m is 2 or 3; L1 and L2 are independently O or S; R4 and R5 are independently C1-C2 alkyl; R6 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; Y4 is CH3, OCH3, OC2H5 or Cl; and X4 is CH3, OCH3, OC2H5 or CH2OCH3; and their agriculturally suitable salts; provided that a) when X is Cl, F, Br or I, then Z is CH and Y is b) wh