Patent CA-1222746-A (CA)
Inventor: PASTERIS ROBERT J
IPC: A01N47/36
Filed: 1985-05-02
Granted: 1987-06-09
Abstract: Title              BA-8606B NOVEL PHENYL-SUBSTITUTED SULFONAMIDES      Abstract of the Disclosure This invention relates to novel condensed ring sulfonylureas and their use as herbicides and growth regulants.  More specifically, the sulfonylureas are of the formula:           wherein J is     n is 0 ir 1: W is 0 or 1: W1 is S W2 is O or S: R is H or CH3: R1 is H. C1-C6 alkyl, C1-C6 haloalkyl, halogen.     nitro. C1-C6 alkoxy, SO2NRaRb? C1-C6 alkyl-thio. C1-C6 alkylsulfianyl, C1-C6 alkylsul-fonyl, CN, CO2Rc. C1-C6 haloalkoxy, C1-C6 haloalkylthio, NH2, C1-C6 alkylamino, di(C1-C6 alkyl) amino, Si(CH3)2(C1-C4 alkyl). Si(CH3)2phenyl or C1-C3 alkyl substituted with C1-C3 alkoxy, C1-C3 alkylthio. C1-C3 alkylsulfinyl,C1-C3 alkylsulfonyl . SO2NRdRe, N02, CN , C02Rf, C1-C3 haloalkoxy or C1-C3 haloalkylthio; Ra is H, C1-C4 alkyl , C1-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 cycloalkyl,  C4 -C7 cycloalkylalkyl or C2-C4 alkoxyalkyl; Rd is C1-C3 alkyl: Re is H or C1-C3 alkyl;       Rf is C1-C3 alkyl R1 is H or C1-C3 ,alkyl. C1-C3 alkoxy, C1-C3 halo-alkoxy, C1-C3 haloalkyl, C1-C3 alkylthio, C1-C3 haloalkylthio, amino. C1-C3 alkylamino, di(C1-C3 alkyl)amino, halogen or N02;       R2 is H, R11, SO2R11, OR11, C(O)R11, C(O)ORR11, (C(O)2R11,(CO)NR11, C(O)NR12R18, C(O)NRA. C(S)SR11, NH2, NR12R18, OH, CN, p(O)R13R14, P(S)R13R14Si(CH3)2R15,:L or C(O)L; R3 is H or CH3; R4 is C1-C4 alkyl; R5 is H or C1-C4 alkyl; R6 is H or CH3; R7 is C1-C4 alkyl, C1 or Br:                               X  is H, C1-C4 alkyl , C1-C4 alkoxy, C1-C4 halo-alkoxy, C1-C4 haloalkyl, C1-C4 haloalkylthio, C1-C4 alkylthio, F, Cl, Br, C2-C5 alkoxyalkyl, C2-C5 alkoxyalkoxy, amino, C1-C3 alkylamino, amino, di(C1-C3 alkyl)amino or C3-C5 cyclo-alkyl; Y is H, C1-C4 alkyl, C1-C4 alkoxy, C1-C4  halo-alkoxy, C1-C4 haloalkylthio, C1-C4 alkylthio, F, Cl, Br, C2-C5 alkoxyalkyl. C2-C5 alkoxy-alkoxy. amino. C1-C3 alkylamino, di(C1-C3 alkyl)amino, C3-C4 alkenyloxy, C3-C4 alkynyl oxy, C2-C5 alkylthioalkyl, C1-C4 haloalkyl, azido, cyano,      N(OCH3)CH3; m is 2 or 3; Q1 and Q2 are independently O or S; R8 is H or C1-C3 alkyl; R9 and R10 are independently C1-C3 alkyl: Z is CH, N, CCH3, CC2H5, CCl or CBr; 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; R11 is C1-C10 alkyl, C1-C10 alkoxyalkoxyalkyl.    C2-C10 alkenyl, C2-C10 alkenylalkenyl, C2-C10 epoxyalkyl, C2-C10 alkynyl, C2-C10 alkynyl-alkynyl, C2-C10 alkynylalkenyl, C3-C6 cyclo-alkyl, C4-C7 cycloalkylalkyl or         when R11 is C3-C6 cycloalkyl or C4-C7 cyclo-alkylalkyl it may optionally be substituted by C1-C4 alkyl, 1 to 3 atoms of Cl or F or 1 Br; when R11 is C1-C10 alkyl, C2-C10 alkenyl or C2-C10 alkynyl it may optionally be substituted by one or more halogens and/or by (R17)m', where when m' is 2, the values of R17 may be identical or different; m' is 1 or 2; R12 is H or C1-C4 alkyl; R13 and R14 are indepenaently C1-C4 alkyl, C1-C4 alkoxy or C1-C4 alkylthio;          R15 is C1-C10 alkyl, benzyl or       R16 is H, F, Cl, Br, CH3, OCH3, NO2, CN, SCH3, SO2CH3 or CF3; R17 is OR18, OC(O)R18, P+R9R10R15, P+(C6H5)3, OC(O)NR12R18, OSO2R18, OP(O)R13R14, P(O)R13R14 OP(S)R13R14, P(S)R13R14, OSi(CH3)2R15, Si(CH3)2R15, SR18, SOR18, SO2R18, SCN, CN, SP(O)R13R14, SP(S)R13R14, N+R12R15R18, NR12R18, NR12C(O)R18, NR12C(O)OR18, NR12C(O)NR12R18, NR12SO2R18, NR12P(O)R13R14, NR12P(S)R13R14, NO2, C(O)R18, C(O)OR18, C(O)NR12R18, SeR18, naphthyl, L,               R18 is H, C1-C10 alkyl, C1-C10 haloalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C6 cycloalkyl or   ;         R19 is H, F, Cl, Br, CH3,        or      ; and L is a 5- or 6-membered aromatic heterocycle, a 5- or 6-membered dihydroaromatic hetero-cycle or a 5- or 6-membered tetrahydroaromatic heterocycle which contains 1-4 heteroatoms selected from 0-1 oxygen atoms, 0-1 sulfur atoms, wherein sulfur may take the form of S, SO or SO2, and/of 0-4 nitrogen atoms, with the proviso that oxygen and sulfur are only linked to each other if the sulfur is in the form of SO or SO2, and these heterocycles may optionally be substituted by 1-4 CH3, 1-2 OCH3, SCH3, Cl, N(CH3)2 or CN or L is a 5- or 6-membered lactone, lactam or cycloalkanone which may optionally be substi-tuted by 1-4 CH3 groups; provided that a) when W is S, then R is H, J is J1, J2, J3 or J4; A is A-1, Z is CH or N, and Y is CH3, OCH3, OC2H5, CH2OCH3, C2H5, CF3, SCH3, OCH2CH=CH2, OCH2C?CH, OCH2CF3, OCH2CH2OCH3, CH(OCH3)2 or       b)  when X is F, Cl or Br, then Z is CH and Y is OCH3, OC2H5, NH2, NHCH3, N(CH3)2 or OCF2H; c)  when R3 is CH3, then n is O;     d) when J is J-1 or J-2 and R2 is H or C1-C4 alkyl, then R1 and R? are other than H, F, Cl, Br, CH3, OCH3, CF3, OCF2H, or SCH3 or X other than CH3, OCH3, OCH2CH3, F, Cl, Br, OCF2H, CH2Cl, CH2Br, CH2F, cyolopropyl or CF3 or Y is C3-C4 alkyl, C3-C4 alkoxy, C4 haloalkoxy, C4 haloalkylthio, C3-C5 alkoxyalkyl, C4-C5 alkoxyalkoxy, C2-C3 alkylamino, di(C2-C3 alkyl)amino, C4 alkenyl-oxy, C4 alkynyloxy, C3-C5 alkylthioalkyl, C2-C4 haloalkyl, C2-C4 alkynyl, C(O)R8 or N(OCH3)CH3; e) the total number of carbon atoms in R2 does not exceed 13; f) when X is C3-C5 cycloalkyl, then Y is CH3, CH2CH3, OCH3, OCH2CH3, CH2OCH3, OCF2H, SCF2H, OCH2CF3, CF3, OCH2CH=CH2, OCH2C?CH, NHCH3, N(CH3)2 or CH(OCH3)2; g) when R18 is H, R17 is other than SOR18, SO2R18, OSO2R18 or NR12C(O)OR18; h) when R1 or R? is para to the sulfonylurea bridge then R1 or R? are H, CH3, F, Cl, Br or OCH3; and i) when X or Y is OCH2CH2F or OCH2CHF2 then R2 is other than C5 alkyl, CH3OCH2CH2, C2H5OCH2CH2 or C1-4 alkyl substituted with 1-3 atoms of F, Cl or Br: j) when X or Y is OCH2CH2F, OCH2CHF2 or OCH2CF3 then the other is not di(C1-C3 alkyl)amino C1-C3 alkylamino or N(OCH3)CH3; k) when X or Y is OCF2H, then Z is CH; and their agriculturally suitable salts.