Patent CA-1257262-A (CA)
Inventor: LEVITT GEORGE
IPC: C07D333/34
Filed: 1986-05-13
Granted: 1989-07-11
Abstract: Title HERBICIDAL THIOPHENESULFONAMIDES   Abstract of the Disclosure Thiophenesulfonamides useful as herbicides and plant growth regulants, herbicidal compositions contain-ing thiophnenesulfonamides, and methods of applying the compositons to areas containing undesired vegetation are described.  The thiophenesulfonamides are of the formula:               or           I                           II wherein R is H or CH3;     R1 is H, C1-C3 alkyl, C1-C3 haloalkyl, halogen, nitro, C1-C3 alkoxy, SO2NRaRb, C1-C3 alkylthio C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, CN, CO2Rc, C1-C3 haloalkoxy, C1-C3 haloalkylthio or phenyl; R'1 is H, Cl, F, Br, C1-C2 alkyl. C1-C2 alkoxy, S(O)nR'10, C1-C2 haloalkyl, CN, C2-C3 cyanoalkyl, CH2OCH3, CH2SCH3 or CH2CH2OCH3; Ra is H, C1-C4 alkyl, C2-C3 cyanoalkyl, methoxy, ethoxy or C3-C4 alkenyl; Rb is H or C1-C3 alkyl; or Ra and Rb may be taken together to form (CH2)3, (CH2)4, (CH2)5 or CH2CH2OCH2CH2; Rc is C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, C2-C4 haloalkyl, C2-C3 cyanoalkyl, cyclopropyl-methyl or C2-C4 alkoxyalkyl:           Q is ER2, NR3R4,  , OSO2R7, C1-C4 haloalkyl.            CN,  SO2NHR21,  ,  , SO2NR22NR23R24 or C1-C4 alkyl substituted with R8:       Q' is H, C1-C4 alkyl, CH2CH=CH2, CF=CFCF3, C1-C2 alkoxy, NO2, Cl, Br, SO2NR'3R'4, SO2N(OCH3)CH3, S(O)nR'5, CO2R'6, C(O)NR'7R'8, C(O)R'9 or C1-C2 alkyl substituted with F, Cl, C1-C2 alkoxy, C1-C2 alkylthio or CN: E is O, S, SO or SO2: W and W1 are independently O or S; J is O, S, NH, NCH3, CH2 or a single bond; R2 i8 C1-C6 alkyl substituted with R8, C2-C6 alkenyl substituted with R8, C3-C6 alkynyl, C3-C6 alkynyl substituted with R8, C1-C6 halo-alkyl, C2-C6 haloalkenyl or C3-C6 haloalkynyl; R3 is C1-C4 alkyl; R4 is H or C1-C4 alkyl;    R3 and R4 are independently C1-C3 alkyl; or R3 and R4 or R3 and R4 may be taken together to form (CH2)4, (CH2)5 or CH2CH2OCH2CH2; R5 and R6 are independently C1-C2 alkyl, C1-C2 alkoxy, C1-C2 alkylthio, C1-C2 alkylamino or di(C1-C2 alkyl)amino; R'5 is C1-C3 alkyl or CH2CH=CH2; R'6 is C1-C3 alkyl, CH2CH=CH2, CH2C?CH, CH2CH2Cl, CH2CH2OCH3; R7 is C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C3-C4 haloalkenyl. C3-C4 alkynyl, C3-C4 halo-alkynyl or NR19R20; R'7 is C1-C3 alkyl; R8 is OR9, S(O)nR10, CO2R10, SO2NR11R12, NR11R12, CONR11R12. C(O)R13, C(W2R14)2,      ,  , CN, SCN, SH, NO2 or N3;   R'8 is H, C1-C3 alkyl or CH2CH=CH2: R9 is H, C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, C1-C4 haloalkyl, C3-C4 haloalkenyl. C3-C4 haloalkynyl, C2-C4 alkylcarbonyl, C1-C4 alkylsulfonyl, C2-C4 alkoxyalkyl, C2-C4 alkyl-thioalkyl or C2-C4 cyanoalkyl; R'9 is H or C1-C3 alkyl: R10 is H, C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, C1-C4 haloalkyl, C3-C4 haloalkenyl, C3-C4 haloalkynyl. C2-C4 alkoxyalkyl, C2-C4 alkylthioalkyl or C2-C4 cyanoalkyl; R'10 is C1-C2 alkyl: R11 is H or C1-C3 alkyl; R12 is H. C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C2-C4 alkoxyalkyl, C2-C4 alkylthio-alkyl, C2-C4 cyanoalkyl, C1-C3 alkoxy, C3-C4 alkenyl or C3-C4 alkynyl: or R11 and R12 may be taken together to form (CH2)3, (CH2)4, (CH2)5 or CH2CH2OCH2CH2; R13 is H, C1-C4 alkyl or C1-C4 haloalkyl R14 is C1-C2 alkyl: R15 is H or CH3: R16 is H, C1-C4 alkyl, C3-C4 alkenyl or C3-C4 alkynyl: R17 is C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkyl amino or di(C1-C4 alkyl)amino: R18 is F, Cl, Br, CN, CH3, OCH3, SCH3 or NO2: R19 is H, C1-C3 alkyl, C3-C4 alkenyl or C3-C4 alkynyl; or R20 i6 H or C1-C3 alkyl  or R19 and R20 may be taken together to form (CH2)4, (CH2)5 or CH2CH2OCH2CH2; R21 i6 C1-C4 alkyl, C1-C3 haloalkyl, C2-C3 cyano-alkyl, cyclopropyl, C3-C4 alkenyl, C3-C4 alkynyl, C2-C4 alkoxyalkyl or C1-C2 alkoxy: R22 is H or C1-C4 alkyl R23 is H or C1-C4 alkyl; R24 is H, C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, C1-C4 haloalkyl or phenyl which may be optionally substituted with R25; or R23 and R24 may be taken together to form (CH2)4, (CH2)5 or CH2CH2OCH2CH2: R25 is H, CH3, Cl, F, Br, NO2, CF3, CN or OCH3; m is 1 or 2: n is 0, 1 or 2: W2 and W3 are independently O or S;          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;             X' is CH3, OCH3, OCH2CH3, CH2OCH3 or OCF2H; 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, C2-C5 alkylsulfinylalkyl, C2-C5 alkyl-sulfonylalkyl, C1-C4 haloalkyl, C4-C5 cycloalkyl, C2-C4 alkynyl, cyano,  ,   ,   or N(OCH3)CH3; q is 2 or 3; L1 and L2 are independently O or S; Rd and Re are independently C1-C2 alkyl: Rf 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; X4 is CH3, OCH3, OC2H5, CH2OCH3 or Cl; and Y4 is CH3, OCH3, OC2H5 or Cl; 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 Cl haloalkoxy, then Z is CH; c) when Q is CF3, then A is A-2, A-3, A-4, A-5, A-6 or A-7;   d) when E is O or S and R9 is H, then R2 is other than CH2OR9: e) when W is S, then A is A-1. R is H and Y is CH3, OCH3, OC2H5, CH2OCH3, C2H5, CF3, SCH3, OCH2CH=CH2. OCH2C?CH, OCH2CH2OCH3. CH(OCH3)2 or   f) the total number of carbon atoms in R1 and Q    is less than or equal to 10: g) when Q is C1-C4 haloalkyl or    , then X    and Y are other than OCF2H or SCF2H; h) X4 and Y4 cannot simultaneously be Cl; i) the substituent Q and the sulfonylurea bridge are on adjacent carbon atoms: j) the total number of carbon atoms in R22, R23 and R24 is less than or equal to 10: k) when R21 is C1-C4 alkyl, C2-C3 cyanoalkyl, C1-C2 alkoxy or C3-C4 alkenyl. then X and Y are other than OCF2H or SCF2H: l) when Y is CN and R1 is H, F, Cl or CH3 then R21 is other than C1-C3 alkyl; m) Q' and the sulfonylurea bridge are on adjacent carbon atoms of the thiophene ring: and n) when X' is OCF2H then Z i6 CH.