C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/249, 260/251
C07D 409/12 (2006.01) A01N 47/36 (2006.01) C07D 333/34 (2006.01) C07D 333/38 (2006.01) C07D 491/044 (2006.01) C07D 521/00 (2006.01)
Patent
CA 1257262
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: Image or Image 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, Image , OSO2R7, C1-C4 haloalkyl. CN, SO2NHR21, Image , Image , 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, Image Image , Image , 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 Image . A-1 A-2 A-3 Image A-4 A-5 A-6 Image 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 alkylthio- alkyl, C2-C5 alkylsulfinylalkyl, C2-C5 alkyl- sulfonylalkyl, C1-C4 haloalkyl, C4-C5 cycloalkyl, C2-C4 alkynyl, cyano, Image , Image , Image 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 Image 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 Image , 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.
509014
E. I. Du Pont de Nemours And Company
Mccallum Brooks & Co.
LandOfFree
Herbicidal thiophenesulfonamides does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Herbicidal thiophenesulfonamides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Herbicidal thiophenesulfonamides will most certainly appreciate the feedback.
Profile ID: LFCA-PAI-O-1283151