Patent CA-1230119-A (CA)
Inventor: HILLEMANN CRAIG L
IPC: A01N47/36
Filed: 1986-11-13
Granted: 1987-12-08
Abstract: TITLE ABSTRACT OF THE DISCLOSURE The invention relates to certain herbicidal sulfonamides, agriculturally suitable compositions thereof and a method for their use as a general or selective preemergent or postemergent herbicide or as a plant growth regulant.       Especially preferred for usage in paddy rice crop because of its selectivity to rice, especially Japonica rice or paddy rice, and activity against undesired plant growth is the compound of Formula I where R1 is ethyl, R2 is difluoromethoxy, X and Y are methoxy and Z is CH as shown below:               or            I                  II wherein R is H or CH3: R1 is C1-C3 alkyl, C3-C4 alkoxyalkyl, C2-C4 halo-alkyl, C3-C4 alkenyl or C3-C4 alkynyl: R2 is C2-C6 alkoxy, C3-C6 cycloalkoxy. C4-C6 cycloalkylalkoxy, C1-C6 haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C3-C6 alkynyl-oxy, C3-C6 haloalkynyloxy, C2-C4 alkoxyalkoxy-C2-C4 haloalkoxyalkoxy, C2-C4 alkylthioalkoxy, C2-C4 haloalkylthioalkoxy, C2-C4 alkylsulfinyl-alkoxy, C2-C4 haloalkylsulfinylalkoxy, C2-C4 alkylsulfonylalkoxy, C2-C4 haloalkylsulfonyl-alkoxy, C2-C4 cyanoalkoxy, OCH2C(O)CH3, OCH2CH2C(O)CH3, C2-C4 aminoalkoxy, C1-C8 alkylthio, C3-C6 cycloalkylthio, C4-C6 cyclo-alkylalkylthio, C1-C8 haloalkylthio, C2-C6 alkenylthio, C2-C6 haloalkenylthio, C3-C6 alkynylthio, C3-C6 haloalkynylthio, C2-C4 alkoxyalkylthio, C2-C4 haloalkoxyalkylthio, C2-C4 alkylthioalkylthio, C2-C4 haloalkylthio-alkylthio, C2-C4 cyanoalkylthio, SCH2C(O)CH3, SCH2CH2C(O)CH3, C2-C4 aminoalkylthio, SC6H5, SCH2C6H5, C1-C8 alkylsulfinyl, C3-C6 cycloalkyl-sulfinyl, C4-C6 cycloalkylalkylsulfinyl, C1-C8 haloalkylsulfinyl, C2-C6 alkenylsulfinyl, C2-C6 haloalkenylsulfinyl, C3-C6 alkynylsulfinyl, C3-C6 haloalkynylsulfinyl, C2-C4 alkoxyalkylsulfinyl, C2-C4 haloalkoxyalkylsulfinyl, C2-C4 cyanoalkyl-sulfinyl, S(O)CH2C(O)CH3, S(O)CH2CH2C(O)CH3, C2-C4 aminoalkylsulfinyl, C2-C8 alkylsulfonyl, C3-C6 cycloalkylsulfonyl, C4-C6 cycloalkyl-alkylsulfonyl, C1-C8 haloalkylsulfonyl, C2-C6 alkenylsulfonyl, C2-C6 haloalkenylsulfonyl, C3-C6 alkynylsulfonyl, C3-C6 haloalkynylsul-fonyl, C2-C4 alkoxyalkylsulfonyl, C2-C4 halo-alkoxyalkylsulfonyl, C2-C4 cyanoalkylsulfonyl. SO2CH2C(O)CH3, SO2CH2CH2C(O)CH3, C2-C4 amino-alkylsulfonyl, CH2F, CHF2, CH2Cl, CHCl2, CH2Br, CHBr2, C2-C6 alkyl substituted with 1-3 atoms of F, Cl or Br, C2-C6 alkenyl. C2-C6 halo-alkenyl, C?CH, C2-C6 haloalkynyl, OC(O)C1-C4 alkyl, CH2C(O)NRaRb, NHCH3, NRbRc or C1-C4 alkyl substituted with C1-C4, alkoxy, C3-C4 cyclo-alkoxy, cyclopropylmethoxy, C1-C4 haloalkoxy, C2-C4  alkenyloxy, C2-C4 haloalkenyloxy, C3-C4 alkynyloxy, C3-C4 haloalkynyloxy, C2-C4 alkoxy-alkoxy, C2-C4 aminoalkoxy, C1-C4 alkylcarbonyl-oxy, C1-C4 haloalkylcarbonyloxy, C1-C4 carbamoyl-oxy, Cl-C4 alkoxycarbonyloxy, OH, OP(O)(OC1-C2 alkyl)2, C1-C4 alkylsulfonyloxy, C1-C2 halo-alkylsulfonyloxy. OSi(CH3)3, OSi(CH3)2C(CH3)3, C1-C4 alkylthio, C3-C4 cycloalkylthio, cyclo-propylmethylthio, C1-C4 haloalkylthio, C2-C4 alkenylthio, C2-C4 haloalkenylthio, C3-C4 alkynylthio, C3-C4 haloalkynylthio, C2-C4 alkoxyalkylthio, C2-C4 aminoalkylthio, SH, SP(O)(OC1-C2 alkyl)2, C1-C4 alkylsulfinyl, C3-C4 cycloalkylsulfonyl, cyclopropylmethylsul-finyl. C1-C4 haloalkylsulfinyl, C2-C4 alkenyl-sulfinyl, C2-C4 haloalkenylsulfinyl, C3-C4 alkynylsulfinyl. C3-C4 haloalkynylsulfinyl, C2-C4 alkoxyalkylsulfinyl, C2-C4 aminoalkyl-sulfinyl, C1-C4 alkylsulfonyl, C3-C4 cyclo-alkylsulfonyl, cyclopropylmethylsulfonyl, C1-C4 haloalkylsulfonyl, C2-C4 alkenylsulfonyl. C2-C4 haloalkenylsulfonyl, C3-C4 alkynylsulfonyl, C3-C4 haloalkynylsulfonyl. C2-C4 alkoxyalkyl-sulfonyl or C2-C4 aminoalkylsulfonyl: R? is C1-C3 alkyl, cyclopropyl, C1-C3 alkoxy, C1-C3 alkylthio,  C1-C3 alkylsulfinyl, C1-C3 alkyl sulfonyl, allyloxy, allylthio, allylsulfinyl, allylsulfonyl, propargyloxy, propargylthio, propargylsulfinyl, propargylsulfonyl, C1-C3 haloalkoxy, C1-C3 alkyl substituted with 1-3 atoms of F or Cl, C1-C2 alkyl substituted with C1-C2 alkoxy, C1-C2 haloalkoxy. C1-C2 alkylthio, C1-C2 haloalkylthio, C1-C2 alkyl-sulfinyl, C1-C2 haloalkylsulfinyl, C1-C2 alkylsulfonyl, C1-C2 haloalkysulfonyl, OH or OC(O)C1-C2 alkyl, C1-C2 alkoxy substituted with Cl-C2 alkoxy, C1-C2 haloalkoxy, C1-C2 alkylthlo, C1-C2 haloalkylthio, C1-C2 alkyl-sulfinyl, C1-C2 haloalkylsulfinyl C1-C2 alkylsulfonyl, C1-C2 haloalkylsulfonyl or CN, OCH2CH2NH2, OCH2CH2NHCH3, OCH2CH2N(CH3)2.     C1-C2 alkylthio substituted by C1-C2 alkoxy, C1-C2 haloalkoxy, C1-C2 alkylthio, C1-C2 haloalkylthio or CN, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkyl-sulfonyl, C2-C3 alkenyl, C?CH, NR?R? or OC(O)C1-C2 alkyl: Ra and Rb are independently H or C1-C3 alkyl: Rc is C2-C4 alkyl, cyclopropylmethyl, C2-C4 cyano-alkyl, CH2C(O)CH3, CH2CH2C(O)CH3, C1-C4 halo-alkyl, C3-C4 alkenyl, C3-C4 haloalkenyl, C3-C4 alkynl, C3-C4 haloalkynyl, C1-C4 alkyl substi-tuted with C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, OH, NH2, NHCH3 or N(CH3)2: R? is H or C1-C2 alkyl: R? is H, C1-C2 alkyl or C1-C2 haloalkyl: Y' is CH3, OCH3 or OCF2H: X  is CH3, OCH3, OC2H5, Cl or Br: Y  is C1-C2 alkyl, C1-C2 alkoxy, OCH2CH2F, OCH2CHF2, OCH2CF3, NHCH3 or N(CH3)2; and Z  is CH or N: and their agriculturally suitable salts: provided that 1) when X is Cl or Br, then Z is CH and Y is C1-C2 alkoxy, NHCH3 or N(CH3)2: and 2) when R2 is SCH3, then R is H, R1 is CH3, X is OCH3, Y is OCH3 and Z is CH. 3) when R1 is C1-C3 alkyl then R2 is other than C2-C6 alkoxy, C1-C8 alkylthio, C1-C8 alkylsulfinyl, C2-C8 alkylsulfonyl, C3-C6 alkenyloxy, C3-C6 alkynyloxy, C3-C6 alkenylthio, C3-C6 alkenylsulfinyl, C3-C6 alkenylsulfonyl, C3-C6 alkynylthio, C3-C6 alkynylsulfinyl, C3-C6 alkynylsulfonyl, OCH2CH2OCH3, OCH2CH2SCH3, OCH2CH2S(O)CH3, OCH2CH2SO2CH3, C2-C6 alkyl substituted with 1-3 atoms of F, Cl or Br, CH2F, CHF2, C1-C4 alkyl substituted with C1-C2 alkoxy, C1-C2 alkylthio, C1-C2 alkylsulfinyl or C1-C2 alkylsulfonyl, OCF2H, OCH2CH2F, OCH2CHF2, OCH2CF3, OCH2CH2Cl, S-cyclohexyl, S-C6H5 or SCH2C6H5; 4) when R1 is C1-C3 alkyl then R2 is other than C1-C3 alkyl, cyclopropyl, C1-C3 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, allyloxy, allylthio, allylsulfinyl, allylsulfonyl, propargyloxy, propargylthio, propargylsulfinyl, propargylsulfonyl, OCF2H, OCH2CH2F, OCH2CHF2, OCH2CF3, OCH2CH2Cl, or C1-C3 alkyl substituted with 1-3 atoms of F or Cl, or C1-C2 alkyl substituted with OCH3 or SCH3?