C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/251, 260/249
C07D 403/00 (2006.01) A01N 47/36 (2006.01) C07D 207/27 (2006.01) C07D 271/113 (2006.01) C07D 413/00 (2006.01) C07D 521/00 (2006.01)
Patent
CA 1231338
Title HERBICIDAL SULFONAMIDES Abstract of the Disclosure The invention relates to certain sulfonylurea compounds having a carbocyclic or heterocyclic ring ortho to the sulfonylurea linkage, compositions thereof and a method of their use as herbicides or plant growth regulants. The sulfonylureas have the formula: Image I wherein J is Image J-1 J-2 J-3 Image J-4 J-5 W is O or S; R is H or CH3: E1 is O, S, SO. SO2 or a single bond. Xa is CH2, CH(CH3), CH2CH2, CH2CH2CH2 or CO; E is a single bond, CH2 or O; Q is a 5- or 6-membered carbocyclic ring con- taining either one or two carbonyl groups and 0-1 endocyclic double bonds; a 5-membered heterocyclic ring, containing 2-4 atoms of carbon and 1-3 heteroatoms selected from the group consisting of 0-2 oxygen, 0-2 sulfur or 0-3 nitrogen, wherein sulfur may take the form of S, SO or SO2, and containing one or two carbonyl or sulfonyl (SO2) groups, or one carbonyl and one sulfonyl group and 0-1 endocyclic double bonds; or a 6-membered heterocyclic ring, containing 2-5 atoms of carbon and 1-3 heteroatoms selected from the group consisting of 0-2 oxygen, 0-2 sulfur or 0-3 nitrogen, wherein sulfur may take the form of S, SO or SO2, and containing one or two carbonyl or sulfonyl (SO2) groups, or one carbonyl and one sulfonyl group and 0-2 endo- cyclic double bonds: said Q value may further be optionally substituted with 1-2 substituent groups: substituents on carbon may be selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl, CH2(C2-C3 alkenyl), CH2(C2-C3 alkynyl), C2-C4 alkoxycarbonyl, CN, OH, C1-C3 alkoxy, C1-C3 alkylthio, C1-C3 alkyl- sulfinyl, C1-C3 alkylsulfonyl or C2-C4 alkyl- carbonyl; substituents on nitrogen may be selected from the group consisting of C1-C4 alkyl, C1-C4 haloalkyl, CH2(C2-C3 alkenyl), CH2(C2-C3 alkynyl), C2-C4 alkoxycarbonyl or C2-C4 alkylcarbonyl; R1 is H, C1-C3 alkyl, C1-C3 haloalkyl, halogen, nitro, C1-C3 alkoxy, SO2NRaRb, C1-C3 alkyl- thio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, CH2CN, CN, CO2RC, C1-C3 haloalkoxy, C1-C3 halo- alkylthio, C2-C4 alkoxyalkyl, C2-C4 alkylthio- alkyl, CH2N3 or NRdRe; Ra is H, C1-C4 alkyl, C2-C3 cyanoalkyl, methoxy or ethoxy; Rb is H, C1-C4 alkyl or C3-C4 alkenyl; or Ra and Rb may be taken together as -(CH2)3-, -(CH2)4-, -(CH2)5- or -CH2CH2OCH2CH2-; Rc is Cl-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, C2-C4 haloalkyl, C2-C3 cyanoalkyl. C5-C6 cycloalkyl, C4-C7 cycloalkylalkyl or C2-C4 alkoxyalkyl; Rd and Re are independently H or C1-C2 alkyl; 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, di(C1-C3 alkyl)amino or C3-C5 cycloalkyl; 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, C1-C4 haloalkyl, C2-C4 alkynyl, azido, cyano, C2-C5 alkylsulfinylalkyl, C2-C5 alkyl- sulfonylalkyl, Image Image or N(OCH3)CH3; m is 2 or 3; L1 and L2 are independently O or S; R2 is H or C1-C3 alkyl; R3 and R4 are independently C1-C3 alkyl; Z is CH, N, CCH3, CC2H5, CCl or CBr; Z1 is CH or N; 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; and Y4 is CH3, OCH3, OC2H5, or Cl; and their agriculturally suitable salts; provided that a) when Q contains 2 heteroatoms selected from 0-2 oxygen and 0-2 sulfur, said heteroatoms are not bonded directly to one another unless in the form O-SO2, and when Q contains 3 nitrogen heteroatoms, only two of these may be bonded directly together; b) 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; c) when X or Y is C1 haloalkoxy, then Z is CH; d) when J is J-2 or J-3, the substituent E1XaQ and the sulfonylurea bridge are on adjacent carbon atoms; e) when E is O, then J is J-1 and W is O; f) 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 1,3-dioxolan-2-yl; g) when the total number of carbon atoms of and Y is greater than four, then the number of carbons of R1 must be less than or equal to two, and the number of carbons of the sub- situent on Q must also be less than or equal to two; h) X4 and Y4 are not simultaneously Cl; i) when A is A-1 and J is J-1 wherein E is a single bond, Xa is CH2, CH(CH3) or CH2CH2 and Q is a 5-membered heterocyclic ring containing one endocyclic double bond or a 6-membered heterocyclic ring containing 1 or 2 endocyclic double bonds which is unsubstituted or substi- tuted by one or more C1-C4 alkyl groups then said heterocycle must contain at least one nitrogen and be bound to Xa through nitrogen;and j) when Xa is CO then E1 is a single bond.
510107
Christensen Joel R.
Rorer Morris P.
E. I. Du Pont de Nemours And Company
Mccallum Brooks & Co.
LandOfFree
Herbicidal sulfonamides 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 sulfonamides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Herbicidal sulfonamides will most certainly appreciate the feedback.
Profile ID: LFCA-PAI-O-1250286