Patent CA-1232274-A (CA)
Inventor: CHRISTENSEN JOEL R
IPC: C07D521/00
Filed: 1986-06-03
Granted: 1988-02-02
Abstract: Title HERBICIDAL SULFONAMIDES                Abstract of the Disclosure This invention relates to certain sulfonylurea compounds having a ring structure, which is attached ortho to the sulfonyl bridge through a double bond, agricultural compositions thereof and a method of their use as general preemergence and/or postemergence herbicides or plant growth regulants.  The sulfonylurea compounds have the formula:       I   wherein J is                  R is H or CH3;  W is O or S;    R1 is H, C1-C3 alkyl, C1-C3 haloalkyl, halogen, nitro,  C1-C3 alkoxy, SO2NRaRb, C1-3 alkyl-thio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, CO2Rc, amino, C1-C3 alkylamino, di(C1-C3)alkyl-amino, CH2OCH3, CH2SCH3 or CH2CN;  Ra is H, C1-C4 alkyl, C2-C3 cyanoalkyl, OCH3 or OC2H5;     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;       R2 is H, C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, phenyl, phenyl substituted with Cl, NO2, CH3 or OCH3, C1-C3 alkoxycarbonyl, C1-C3 alkylsulfonyl or di(C1-C2)alkylamino sulfamoyl;       Q is     n is 0, 1 or 2;       R3 is H, C1-C4 alkyl, C1 or Br;       R10 is H or C1-C4 alkyl;       E is a bridge of 4 or 5 atoms, which may be substituted or unsubstituted, containing 0-2 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen, and also con-taining 2-5 carbon atoms, said bridge together with one carbon attachment site forming a partially saturated or a fully unsaturated, nonaromatic 5- or 6-membered carbocyclic or heterocyclic ring, with the proviso that when E contains two atoms of oxygen or sulfur, they must be separated by at least one atom of carbon, and that oxygen if the sulfur are only linked to each other if the sulfur is in the form SO or SO2; in the bridging group E, sulfur may take the form of S, SO or SO2 carbonyl, thiocarbonyl or the cyclic 5- and 6-membered ketals thereof; when one of the bridging atoms is a substituted carbon, the substituents on said carbon includes H, C1-C4 alkyl, C1-C4 alkoxy, halogen or C1-C4 halo-alkoxy; when the bridging atom is a nitrogen, the substituent on said nitrogen includes H, C1-C4 allkyl, C1-C4 haloalkyl, C1-C4 alkoxy-alkyl, C2-C4 cyanoalkyl, C3-C4 alkenyl or C3-C4 alkynyl;     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 alkoxyalkoxy, amino, C1-C3 alkylamino or di(C1-C3)alkyl-amino;      Y  is H, C1-C4 alkyl 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)alkylamino, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C2-C5 alkylsulfinylalkyl, C1-C4 haloalkyl, C2-C5 alkylsulfonylalkyl, C3-C5 cyckialkyl, C2-C4 alkynyl, C2-C5 alkylthioalkyl,   or N(OCH3)CH3;   W1  and W2 are independently O or S; m  is 2 or 3;   Rd  is H or CH3;   Re  is C1-C2 alkyl;   Rf  is C1-C2 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, OCF2H, SCF2H, CH3 or CH2CH3;   X3  is CH3 or OCH3;   Y3  is H or CH3;   X4  is CH3, OCH3, OC2H5, CH2OCH3 or Cl;   Y4  is CH3, OCH3, OC2H5 or Cl; and their agriculturally suitable salts; provided that a)  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, OHC2CH2OCH3, CH(OCH3)2 or     b)  when X is Cl, Br, F or I, then Z is CH and Y is OCH3, OC2H5, NH2, NHCH3, N(CH3)2, OCF2H or N(OCH3)CH3;     c) when X or Y is C1 haloalkoxy. then Z is CH; d) when the bridging group E contains a thicoar-bonyl substituent, said thiocarbonyl carbon must be bonded to a nitrogen atom: e) when J is J-2 or J-3, the substituent Q and the sulfonylurea bridge are on adjacent carbon atoms;   f) when the total number of carbon atoms in X and Y is greater than 4, then the total num-ber of carbon atoms in R1, R2 and Q is less than or equal to 10: and g)  X4 and Y4 are not simultaneously C1.