Patent CA-1308101-C (CA)
Title: Herbicidal pyridinesulfonylureas
Inventor: LIANG PAUL HSIAO-TSENG
IPC: A01N47/36
Filed: 1987-12-03
Granted: 1992-09-29
Abstract: Title HERBICIDALPYRIDINESULFONYLUREAS            Abstract This invention relates to herbicidal pyridine-sulfonylureas, which re highly active as preemergence and postemergence herbicides, of the following:       wherein   J-l    J-2        J-3   R is H or CH3;     W is O or S;     R1 is Rf or Rg;      Rf is H, C1-C3 alkyl, C1-C3 haloalkyl, halogen, NO2, C1-C3 alkoxy, C1-C3 alkylthio or CN;  Rg is C1-C3 haloalkyl, C2-C3 alkyl, cyclopropyl, C1-C3 alkyl substituted by C1-C3 alkoxy, OH, C1-C2 alkylthio or CN, CN, W2R11, amino, C1-C3 alkylamino or C1-C3 dialkylamino;      R2 is C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C5 cycloalkylthio, C3-C5 cycloalkylsulfinyl, C3-C5 cycloalkylsulfonyl, SO2NH2, SO2NRdRe, SO2NR'7R8, SO2NR7R8, OSO2R8, SO2OR8, N3, P(Wl)(OC1-C2 alkyl)2, CN, CO2R9, CO2R'9, CH2F, CF2H, CH2Cl, CCl2H or C2-C4 haloalkyl;       R3 is C1-C4 alkylsulfinyl, C3-C5 cycloalkylthio, C3-C5 cycloalkylsulfinyl, C3-C4 cycloalkylsul-fonyl, SO2NH2, SO2NRdRe. SO2NR7R8, SO2NR'7R8, OSO2R8, SO2OR8, N3, P(W1)(OC1-C2 alkyl)2, CN, CO2R9, CO2R'9 or C1-C4 haloalkyl;       R4 is C1-C4 alkylsulfinyl, C3-C5 cycloalkylthio, C3-C5 cycloalkylsulfinyl, C3-C4 cycloalkylsul-2NH2, SO2NRdRe, S°2NR7R8' OSO R , SO2OR8, N3, P(W1)(OC1-C2 alkyl)2, CN, CO2R9  or C1-C4 haloalkyl;       R5 is C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C5 cycloalkylthio, C3-C5 cycloalkylsulfinyl, C3-C5 cycloalkylsulfonyl, SO2NH2, SO2NRdRe, SO2NR7R8, OSO2R8, SO2OR8, N3, P(W1)(OC1-C2 alkyl)2, CN, CO2R9 or C1-C4 haloalkyl;       R6 is C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C3-C4 alkenylthio, C3-C4 alkenylsulfinyl, C3-C4 alkenylsulfonyl, C3-C4 alkynylthio, C3-C4 alkynylsulfinyl, C3-C4 alkynylsulfonyl, C3-C5 cycloalkylthio, C3-C5 cycloalkylsulfinyl, C3-C5 cycloalkylsulfonyl, SO2NRdRe, SO2NR7R8, OSO2R8,  SO2OR8, N3, P(W1)(OC1-C2 alkyl)2, CN, CO2R9 or C1-C4 halo-alkyl;       R7 is H, C2-C3 cyanoalkyl, C3-C4 alkenyl or C3-C4 alkynyl;     R'7 is C1-C4 alkyl;       R8 is C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C3-C4 alkynyl, C2-C4 alkoxyalkyl or cyclo-propyl; or R7 and R8 may be taken together as -(CH2)3-, -(CH2)4-, -(CH2)5- or -CH2CH2OCH2CH2-;       R9 is CH2CH2R10, CH2CF3, C3-C4 halOalkyl, C3-C4 alkynyl, C2-C4 alkylthioalkyl, C3-C5 cycloalkyl or C4-C7 cycloalkylalkyl;       R9' i6 C1-C4 alkyl, C3-C4 alkenyl, CH2CH2Cl, CH2CH2Br, CH2CH2OCH3 or CH2CH2OC2H5;  R10 is OH, F, CN, OSO2(C1-C3 alkyl) or OSO2(C1-C3 haloalkyl);       R1l is C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 alkenyl or C3-C4 alkynyl;          W1 is O or S;          W2 is O or S;            A is                                                or X is H, C1-C4 alkyl, C1-C4 alkoxy. C2-C4 halo-alkoxy, C1-C4 haloalkyl, C2-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, C2-C4 halo-alkoxy, C2-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, C2-C5 alkylsulfinylalkyl, C2-C5 alkyl-sulfonylalkyl, C1-C4 haloalkyl, C2-C4 alkynyl, C3-C5 cycloalkyl, azido,   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;           Rd is H or C1-C2 alkyl;           Re is C1-C2 alkoxy;           Z is CH, N, CCH3, CC2H5, CCl 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 Cl;           Y4 is CH3, OCH3, OC2H5 or Cl; 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 or N(OCH3)CH3; 2) when W is S, then R is H, A is 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     ;   3)  when the total number of carbon atoms of X and Y is greater than four, then the combined number of carbons of R1, R2, R3, R4, R5 or R6 is less than or equal to six; 4)  when J is J-1 and R2 is C1-C4 alkylsulfinyl C1-C4 alkylsulfonyl, SO2NRdRe, SO2RN?R8 or CO2R?, or when J is J-2 and R3 is CF3, SO2NRdRe, SO2RN?R8, C1-C4 alkylsulfinyl or CO2R?, then Y is other than C2-C5 alkylthioalkyl, C2-C5 alkylsulfinylalkyl, C2-C5 alkylsulfonylalkyl,            or                   ;   5)  when J is J-2 or J-3 and R3 or R4 is C1-C4 alkylsulfinyl, then X and Y are other than NH2 or NHCH3; 6)  when J is J-2 and R3 is C1-C4 alkylsulfinyl or SO2NRdRe, or R7 is H, then X and Y are other than C2-C4 haloalkoxy; 7)  when J is J-5, then R7 is other than H and R6 is other than SO2NRdRe; 8)  when J is J-2 and R3 is SO2NH2 or SO2NRdRe, or R7 is H, then X is other than iodine; 9)  when J is J-2 and R7 is H or R3 is SO2NRdRe, then Y is other than C2-C4 alkynyl; 10)  X4 and Y4 are not simultaneously Cl; 11)  when J is J-1, J-2, J-3, J-4 and A is A-5, then Rf is other than H; 12)  when J is J-1 or J-2, then A is other than A-6; 13)  when J is J-1 and A is A-7, then R2 is other than C1-C4 alkysulfonyl;     14) when R2 or R3 is CO2R'9 or SO2NR'7R8, then R1 is Rg and when R2 or R3 is other than CO2R'9 or SO2NR'7R8, then R1 is Rf; and 15) when J is J-2 and R1 is adjacent to the sulfonylurea bridge, then Rg is C1-C3 haloalkyl. C2-C3 alkyl, cyclopropyl, CN, W2R11, amino, C1-C3 alkylamino or C1-C3 dialkylamino.