Patent CA-1231339-A (CA)
Inventor: RORER MORRIS P
IPC: C07D271/113
Filed: 1986-05-27
Granted: 1988-01-12
Abstract: Title HERBICIDAL SULFONAMIDES        Abstract of the Disclosure This invention relates to herbicidal benzene sulfonamides containing a five or six membered hetero-cyclic ring consisting of 2-3 heteroatoms and 1-2 carbonyl groups as a substituent on benzene.      The sulfonamides have the formula:       wherein J is     ,    ,  ,      ,      W is O or S;        R is H or CH3;        E is a single bond, CH2 or O:        Q is a saturated 5- or 6-membered heterocyclic ring, bonded through carbon or nitrogen, containing a carbonyl group and 2-3 hetero-atoms selected from the group consisting of 0-2 oxygen, 0-2 sulfur or 0-2 nitrogen; a 5-membered heterocyclic ring, bonded through carbon or nitrogen, containing a carbonyl group and 2-3 heteroatoms selected from the group consisting or 0-2 oxygen, 0-2 sulfur or 1-3 nitrogen and containing one endocyclic double bond; a 6-membered heterocyclic ring, bonded through carbon or nitrogen, containing a carbonyl group and 2-3 heteroatoms selected from the group consisting of 0-2 oxygen, 0-2 sulfur or 1-3 nitrogen and containing one or two endocyclic double bonds; or a 5-membered heterocyclic ring, bonded through or nitrogen, containing two adjacent carbonyl groups and 2 heteroatoms selected from the group consisting of 0-1 oxygen, 0-1 sulfur, or 1-2 nitrogen and containing one endocyclic double bond, said Q value may be substituted or unsubstituted wherein the substituent groups are selected from the group consisting of C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C3-C4 haloalkenyl, C3-C4 alknyl, C3-C4 haloalknyl, C1-C3 cyanoalkyl, C2-C4 alkoxyalky, C2-C4 alkylthioalkyl, C2-C4 alkyl-carbonyl, C3-C4 alkylcarbonylalkyl, C1-C4 alkyl substituted with OH or NH2, C2-C4 alkylamino-alkyl, C3-C4 dialkylaminoalkyl, CH2CH(OCH3)2,  , C(O)N(CH3)2, P(O)(OC1-C2 alkyl)2, P(S)(OC1-C2 alkyl)2 or C1-C2 alkyl substituted with C1-C2 alkoxycarbonyl;      R1 is H, C1-C3 alkyl, C1-C3 haloalkyl, halogen, nitro, C1-C3 alkoxy, SONRaRb, C1-C3 alkyl-thio, C1-C3 alkylsulfinyl, C1-C3 alkysul-fonyl, CH2CN, CN, CO2Rc, C1-C3 haloalkoxy, C1-C3 haloalkylthio, C2-C4 alkoxyalkyl, C2-C4 alkylthioalkyl, 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 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;          Rd and Re are independently H or C1-C2 alkyl;            A is     ,   ,     ,   ,    ,    ;     or  ;             X is H, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 halo-alkoxy, C1-C4 haloalkyl, C1-C4 haloalkylthio, C1-C4 alklthio, 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 alkoxyalky, C2-C5 alkoxyalkoxy, amino, C1-C3 alkylamino, di(C1-C3 alkyl)amino, C3-C4 alkenyloxy, C3-C4 alkynloxy, 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 C1; 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, 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 3-3, the substituent Q 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, 2 is CH or N and Y is CH3, OCH3, OC2C?CH, OCH2CH2OCH, CF3, SCH3, OCH2CH=CH2, OCH2C?CH. OCH2CH2OCH3, CH(OCH3)2 or 1,3-dioxolan-2-yl; g) when the total number of carbons of X 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 substituent on Q must be less than or equal to two: h) X4 and Y4 are not simultaneously C1; and i) when Q is bound through nitrogen and contains 2-heteroatoms and one carbonyl group, and said heteroatoms are bound through the carbonyl, then J other than J-1.