Patent CA-1231338-A (CA)
Inventor: CHRISTENSEN JOEL R
IPC: A01N47/36
Filed: 1986-05-27
Granted: 1988-01-12
Abstract: 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:       I wherein J is                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                   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,        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.