Patent CA-1232273-A (CA)
Inventor: HAY JAMES V
IPC: C07D231/18
Filed: 1985-12-03
Granted: 1988-02-02
Abstract: Title HERBICIDAL SULFONAMIDES Abstract of the Disclosure 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, hetero-cyclic rings which contain 1 heteroatom selected from O, S, and NR3, alkenes, substituted alkenes, cyclo-alkenes, 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:                         I wherein                                         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 cyclo-alkyl, C4-C7 cycloalkylalkyl or C2-C4 alkoxy-alkyl;       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 alkyl-amino)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 alkyl-sulfonyl, 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 alkoxy-carbonyl, 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                                    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 alkylthio-alkyl, C1-C4 haloalkyl, C3-C5 cycloalkyl, C2-C4 alkynyl, ?R6,  ,  ,   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 OCH3, OC2H5. N(OCH3)CH3, NHCH3, N(CH3)2 or OCF2H; b) when X or Y is OCF2H then Z is CH: c) when L is L-2 or L-3, then the W substituent and the sulfonylurea bridge are on adjacent carbon atoms, and when L is L-9 or L-10, then Q and the sulfonylurea bridge are on adjacent carbon atoms; d) when W1 is C3 alkenyl, then L is L-3, L-4, L-5 or L-6: e) when L is L-1, then n is 1 and W is W2: f) when L is L-1 and W2 is C2 or C3 alkynyl, said group must be substituted: g) when W1 is C3-C8 alkenyl or C4-C7 cycloalkenyl substituted with OH, then the OH substituent is not bonded directly to the olefinic group: h) when L is L-3, then the sulfonylurea bridge is bonded at the 3- or 5-position; i) when W3 is 5, then R is H, A is A-1, and Y is CH3, OCH3, OC2H5, CH2OCH3, C2H5. CF3, SCH3, OCH2CH-CH2, OCH2C?CH, OCH2CH2OCH3 or CH(OCH3)2; j) when the total number of carbon atoms of X and Y is greater than four, then the number of car-bons of R1 must be less than or equal to two and either the number of carbons of W must be less than or equal to four, or the number of carbons of Q must be less than or equal to six: k) the total number of carbon atoms of R12 and R13 must be less than or equal to four; and l) when L is  L-1 through L-7 and A is A-7, then Z is CH.