Herbicidal sulfonamides

Details Herbicidal sulfonamides Herbicidal sulfonamides

C - Chemistry, Metallurgy

07

D

260/242.5

C07D 403/12 (2006.01) A01N 47/36 (2006.01) C07D 231/18 (2006.01) C07D 303/34 (2006.01) C07D 333/34 (2006.01) C07D 409/12 (2006.01) C07D 521/00 (2006.01) C07F 7/10 (2006.01)

Patent

CA 1232273

Title HERBICIDAL SULFONAMIDES Abstract of the Disclosure This invention relates to certain sulfonylurea compounds having substitutents ortho to the sulfonylurea linkage that include 3- or 4-membered carbocyclic rings, saturated 5- or 6- membered carbocyclic rings, hetero- cyclic rings which contain 1 heteroatom selected from O, S, and NR3, alkenes, substituted alkenes, cyclo- alkenes, substituted cycloalkenes, alkynes, and substituted alkynes, agriculturally suitable compositions thereof and a method of their use as herbicides or plant growth requlants. More specifically, the compounds are of compounds are of the formula: Image I wherein Image Image L-1 L-2 Image Image L-3 L-4 Image Image L-5 L-6 Image L-7 Image L-8 L-9 Image L-10 L-11 Image L-12 L-13 R is H or CH3; W3 is O or S, n is 0 or 1: E is S(O)p or Se; p is 0, 1 or 2; R1 is H, C1-C3 alkyl, C1-C3 haloalkyl, halogen, nitro, CH2CN, CH2OCH3, CH2SCH3, CN, C1-C3 alkoxy, SO2NRIRII, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl or CO2RIII; RI is H, C1-C4 alkyl, C2-C3 cyanoalkyl, methoxy or ethoxy; RII is H; C1-C4 alkyl or C3-C4 alkenyl; or RI and RII may be taken together as -(CH2)3-, -(CH2)4-, -(CH2)5- or -CH2CH2OCH2CH2-; RIII is C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, C2-C4 haloalkyl, C2-C3 cyanoalkyl, C5-C6 cyclo- alkyl, C4-C7 cycloalkylalkyl or C2-C4 alkoxy- alkyl; R2 is C1-C3 alkyl; W is W1 or W2; W1 is C2-C8 alkenyl or C4-C7 cycloalkenyl either of which may be optionally substituted with 1-3 atoms of F, Cl or Br, OH, CN, NO2, C1-C3 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, amino, C2-C4 alkenyl, C1-C3 alkylamino, di(C1-C3 alkyl)amino, (C1-C3 alkyl- amino)sulfamoyl, di(C1-C3 alkylamino)sulfamoyl, OC(O)C1-C3 alkyl, OC(O)C1-C3 alkoxy, OSO2C1-C3 alkyl, OSO2C6H5, OSO2-4-CH3-C6H4, phenyl or phenyl substituted with halogen, CH3, OCH3, SCH3 or NO2; W2 is C2 alkynyl which may be substituted with phenyl or phenyl substituted with halogen, CH3, OCH3, SCH3 or NO2 or W2 is C3-C8 alkynyl which may be optionally substituted with 1-3 atoms of F, Cl or Br, OH, CN, NO2, C1-C3 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkyl- sulfonyl, amino, C1-C3 alkylamino, di(C1-C3 alkyl)amino, (C1-C3 alkylamino)sulfamoyl, di(C1-C3 alkylamino)sulfamoyl, OC(O)C1-C3 alkyl, OC(O)C1-C3 alkoxy- OSO2C1-C3 alkyl- OSO2C6H5, OSO2-4-CH3-C6H4, phenyl or phenyl substituted with halogen, CH3, OCH3, SCH3 or NO2; Q is a 3- or 4-membered heterocyclic ring which contains one heteroatom selected from O, S and NR3, or a 3- or 4-membered carbocyclic ring in which one carbon atom may optionally be in the form of a carbonyl group, or a fully-saturated 5- or 6-membered carbocyclic ring, and Q may be optionally substituted with 1-4 substituents selected from halogen, CN, OH, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 alkylthio, C2-C3 alkoxy- carbonyl, C1-C4 alkylsulfonyl, (C1-C4 alkyl)- aminosulfamoyl and di(C1-C4 alkyl)aminosulfamoyl; R3 is C1-C4 alkyl: R12 is H or OR14: R13 is H or C1-C4 alkyl; R14 is H, C1-C4 alkyl, C3-C4 alkenyl. C3-C4 halo- alkenyl, C3-C4 alkynyl, C3-C4 haloalkynyl, C2-C4 alkylcarbonyl, C(O)NR15R16, C1-C4 alkylsulfonyl, C2-C4 alkoxyalkyl or C2-C4 alkylthioalkyl: R15 and R16 are independently H or C1-C2 alkyl: R17 is H or C1-C4 alkyl: A is Image Image Image A-1 A-2 A-3 Image Image 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; 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, C3-C5 cycloalkyl, C2-C4 alkynyl, ?R6, Image , Image , Image or N(OCH3)CH3; m is 2 or 3; L1 and L2 are independently O or S; R4 and R5 are independently C1-C2 alkyl; R6 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; Y4 is CH3, OCH3, OC2H5 or Cl; and X4 is CH3, OCH3, OC2H5 or CH2OCH3; 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 OCF2H then Z is CH: c) when L is L-2 or L-3, then the W substituent and the sulfonylurea bridge are on adjacent carbon atoms, and when L is L-9 or L-10, then Q and the sulfonylurea bridge are on adjacent carbon atoms; d) when W1 is C3 alkenyl, then L is L-3, L-4, L-5 or L-6: e) when L is L-1, then n is 1 and W is W2: f) when L is L-1 and W2 is C2 or C3 alkynyl, said group must be substituted: g) when W1 is C3-C8 alkenyl or C4-C7 cycloalkenyl substituted with OH, then the OH substituent is not bonded directly to the olefinic group: h) when L is L-3, then the sulfonylurea bridge is bonded at the 3- or 5-position; i) when W3 is 5, then R is H, A is A-1, and Y is CH3, OCH3, OC2H5, CH2OCH3, C2H5. CF3, SCH3, OCH2CH-CH2, OCH2C?CH, OCH2CH2OCH3 or CH(OCH3)2; j) when the total number of carbon atoms of X and Y is greater than four, then the number of car- bons of R1 must be less than or equal to two and either the number of carbons of W must be less than or equal to four, or the number of carbons of Q must be less than or equal to six: k) the total number of carbon atoms of R12 and R13 must be less than or equal to four; and l) when L is L-1 through L-7 and A is A-7, then Z is CH.

496792

Affiliated with

Also associated with

Rating

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.

Rate now

Comments { 0 }

Profile ID: LFCA-PAI-O-1306646