Patent CA-1223009-A (CA)
Inventor: CHRISTENSEN JOEL R
IPC: C07D521/00
Filed: 1985-11-21
Granted: 1987-06-16
Abstract: Title HERBICIDAL SULFONAMIDES Abstract of the Disclosure This invention relates to herbicidally active sulfonamide compounds having a heterocyclic carbonyl group ortho to the sulfonyl bridge.  More specifically the compounds of the invention are of the formula:                         I wherein W is O or S;                                      Q is a saturated 5-  or 6-membered ring containing 1 or 2 heteroatoms selected from 0-1 oxygen, 0-1 sulfur and 0-1 nitrogen, or Q is an unsaturated or partially unsaturated 5- or 6-membered ring containing 1-3 heteroatoms selected from 0-1 sulfur. 0-1 oxygen and 0-3 nitrogen; or Q is a saturated 3- or 4-membered heterocyclic ring containing one nitrogen atom and is bonded to G through said nitrogen; and Q may be optionally substituted by 1-4 groups selected from L: G is a C1-C3 alkyl radical in which one of the carbons must be substituted with R2 and/or R3. and the remaining carbon atoms may optionally be substituted with 1 or 2 substituents selected from CH3, F and Cl; R is H or CH3: R1 is H  C1-C3 alkyl. C1-C3 haloalkyl, halo-gen, nitro. C1-C3 alkoxy, SO2NR1R11, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkyl-sulfonyl. CO2RIII, CH2OCH3, CH2SCH3, CH2CN, NH2, NHCH3 or N(CH3)2; R2 is OH. OCH3 or OC2H5; R3 is OCH3 or OC2H5; or R2 and R3 can be taken together to form a carbonyl group. or the 5- or 6-membered ring ketal or thioketal thereof: 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 cycloalkyl. C3-C7 cycloalkylalkyl or C2-C4 alkoxyalkyl:         L is C1-C4 alkyl, C1-C3 haloalkyl, halogen, C1-C3 alkoxy, C1-C3 alkylthio. C3-C4 alkenyloxy. C3-C4 alkenylthio, C1-C2 haloalkoxy or C1-C2 haloalkylthio:            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 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, C(O)R4,     or N(OCH3)CH3; m is 2 or 3: L1 and L2 are independently O or S; R5 and R6 are independently C1-C2 alkyl; R4 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 of SCH3;     Y3 is CH3, CH2CH3 of CH2CF3;     X3 is CH3 or OCH3:¦     X4 is CH3, OCH3, OC2H5, CH2OCH3 or Cl: and Y4 is CH3, OCH3 or OC2H5: and their agriculturally suitable salts; provided that a) when X is Cl, F, Br or I, then Z is CH and Y is OCH3, OCH2CH3, N(OCH3)CH3, NHCH3, N(CH3)2 or OCF2H; b) when X or Y is OCF2H, then Z is CH: c) when J i6 J-2 or J-3, then GQ and the sulfonyl-urea bridge must be on adjacent carbon atoms; d) when Q is bonded to G throuqh nitrogen, then the adjacent carbon atom of G cannot be sub-stituted with OH, F or Cl; e) when G is Cl alkyl in the form of a carbonyl group, then Q is6 other than      ,      or   ;   f) when the total number of carbon atoms of X and Y is greater than four, then the total number of carbon atoms of Rl and GQ must be less than or equal to ten; g) when W is S, then A is A-l, R is H, and Y is CH3, OCH3, OC2H5, CH2OCH3, C2H5, CF3, SCH3, OCH2CH=CH2, OCH2C?CH, OCH2CH2OCH3 or CH(OCH3)2: and h) when R3 is OCH3 or OC2H5, then R2 i6 other than OH.