HERBICIDAL THIOPHENESULFONAMIDES

摘要

Title HERBICIDAL THIOPHENESULFONAMIDES Thiophenesulfonamides useful as herbicides and plant growth regulants, herbicidal compositions containing 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, cyclopropylmethyl 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 haloalkyl, 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 haloalkynyl 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 alkylthioalkyl 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 alkylthioalkyl, 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 . A-1 A-2 A-3 A-4 A-5 A-6 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; 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 alkylthioalkyl, C2-C5 alkylsulfinylalkyl, C2-C5 alkylsulfonylalkyl, C1-C4 haloalkyl, C4-C5 cycloalkyl, C2-C4 alkynyl, cyano,