Patent CA-1236459-A (CA)
Inventor: ARTZ STEVEN P
IPC: C07D521/00
Filed: 1986-06-05
Granted: 1988-05-10
Abstract: Title HERBICIDAL SULFONAMIDES Abstract of the Disclosure Novel compounds are useful as herbicides and plant growth regulants.  Such compounds are of the formula:                         wherein E is CH2 or a single bond; W is O or S: R is H or CH3: R1 is F. Cl, Br. NO2. C1-C4 alkyl.    C2-C4 alkenyl. C2-C4 haloalkenyl, C2-C4 alkynyl, C1-C4 haloalkyl. C1-C4 alkoxy, OCH2CH2OCH3, C1-C4 haloalkoxy, C3-C4 alkenyloxy. C2-C4 haloalkenyloxy, C3-C4 alkynyloxy.  CO2R3. CONR4R5, SO2NR4R5. SO2N(OCH3)CH3, S(O)nR6, OSO2R7, C1-C2 alkyl substituted with C1-C2 alkoxy, OH or C1-C2 alkylthio, CH2CN, C6H5  , CR8(OR9)2,             R2 is CH(R16)CN. CH(R17)SCN,          CH(R17)NR12R13, CH(R17)SeR14, CH(R17)N3,  CH(R17)NO2, CH(R17)NC,  , -C(OR18)2,  -C(SR18)2,    , .                   or N(OCH3)CH3: m is 2 or 3:    Q1 and Q2 are independently O or S; Ra is H or C1-C3 alkyl; Rb and Rc are independently C1-C3 alkyl; Z is CH, N. CCH3, CC2H5, CC1 or CBr; 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; X3 is CH3 or OCH3; Y3 is H or CH3: X4 is CH3, OCH3, OC2H5, CH2OCH3 or C1: Y4 i6 CH3, OCH3, OC2H5 or  C1; and their agriculturally suitable salts: provided that 1) when X is halogen, then Z is CH and Y is OCH3, OC2H5, NH2. NHCH3, N(CH3)2, OCF2H or N(OCH3)CH3; 2) when X or Y is C1 haloalkoxy, then Z i6 CH; 3) when W is S, then R is H, A i6 A-1, Z is CH or N, and Y is CH3, OCH3, OC2H5, CH2OCH3, C2H5, CF3, SCH3, OCH2CH=CH2, OCH2C?CH, OCH2CH2OCH3, CH(OCH3)2 or      R3 is C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl,     , CH2CH2Cl, CH2CH2F, or C1-C2 alkyl substituted with OCH3 or SCH3; R4 is C1-C3 alkyl; R5 is H or C1-C3 alkyl; R4 and R5 may be taken together to form (CH2)3 or (CH2)4; R6 is C1-C3 alkyl, CH2CH-CH2 OR CH2C?CH; R7 is C1-C3 alkyl or N(CH3)2; R8 is H, C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, CH2CH2Cl, CH2 CH2F, C1-C2 alkyl substituted with OCH3 or SHC3 and C3-C6 cycloalkyl; R9 is C1-C2 alkyl; R10 and R11 are independently C1-C2 alkyl, C1-C2 alkoxy, C1-C2 alkylthio, NHCH3 or N(CH3)2; R12 AND R13 are independently H or C1-C2 alkyl; R14 is C1-C3 alkyl; R15 is H or CH3; R16 is H, C1-C2 alkyl or F; R17 is H or C1-C2 alkyl; R18 is C1-C2 alkyl; R19 is H, Si(CH3)3 or C1-C2 alkyl; R20 is H or C1-C2 alkyl; p is 1 or 2; n is 0,1, or 2;       X is H, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, 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 haloalkoxy, C1-C4 haloalkylthio, C1-C4 alkylthio, C2-C5 alkoxyalkyl, C2-C5 alkoxy-alkoxy, amino, C1-C3 alkylamino, di(C1-C3 alkyl)amino, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C2-C5 alkylthioalkyl, C2-C5 alkyl6ulfinylalkyl, C2-C5 alkylsulfonylalkyl, C1-C4 haloalkyl, C2-C4 alkynyl, C3-C5 cycloalkyl, azido, cyano, 4)   when the total number off carbon atoms of X      and Y is greater than four, then the combined number of carbons of R1 and R2 is less than or equal to six;   5)   when R2 is C(O)R17, then R1 other than C1-C4 haloalkyl or C2 alkyl substituted with C1-C2 alkoxy or C1-C2 alkylthio, and Y is other than cyclopropyl; 6) when Y is C2-C5 alkylthioalkyl,C2-C5 alkylsulfinylalkyl or C2-C5 alkylsulfonylalkyl,then R2 is other than CH(R17)NO2, and 7) X4 and Y4 are not simultaneously C1.