C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/251, 260/249
C07D 239/28 (2006.01) A01N 47/36 (2006.01) C07D 295/194 (2006.01) C07D 403/12 (2006.01) C07D 521/00 (2006.01) C07F 7/10 (2006.01)
Patent
CA 1231337
Title HERBICIDAL SULFONAMIDES Abstract of the Disclosure Thiocarbonylsulfonylureas, useful as herbicides and growth regulants, herbicidal compositions employing these compounds and methods of applying them to soil or directly to plants have been discovered. The thiocarbonyl- sulfonylureas are of the formula: Image wherein J is Image J-1 J-2 J-3 Image J-4 J-5 J-6 Image J-7 J-8 J-9 Image J-10 J-11 J-12 w is O or S; R is H or CH3; E is a single bond or -CH2-; Q is Q2 or Q3; Q2 is - Image Q3 is - Image n is 0 or 1; W1 is 0 or S; R1 is H, C1-C4 alkyl, C1-C3 haloalkyl, Cl, Br, F, NO2, C1-C3 alkoxy, SO2NRaRb, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, CN, CO2Rc, C1-C3 haloalkoxy, C1-C3 haloalkylthio, CH2OCH3, CH2SCH3, CH2CN, NH2, NHCH3 or N(CH3)2; R2 is H, Cl, Br, C1-C4 alkyl, C1-C3 alkoxy or C1-C3 alkylthio; R3 is H, C1-C4 alkyl, C3-C4 alkenyl or phenyl; Ra is H, C1-C4 alkyl, C2-C3 cyanoalkyl or C1-C3 alkoxy; 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; R13 is C1-C4 alkyl; R14 is C1-C4 alkyl; R15 is H, C1-C6 alkyl, C2-C3 alkyl substituted with C1-C3 alkoxy or phenoxy, C3-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl, C5-C6 cycloalkenyl, C4-C7 cycloalkylalkyl, C5-C6 cycloalkyl substi- tuted with CH3 or OCH3, CH2CN, CH2CH2CN, OCH3, OC2H5, N(CH3)2, Image Image R16 is H, Cl-C6 alkyl, CH2CH=CH2, CH2CN or CH2CH2CH; or R15 and R16 may be taken together to form (CH2)3, (CH2)4, (CH2)5, (CH2)6, CH2CH=CH2CH2, CH2CH2OCH2CH2 or CH2CH2N(CH3)CH2CH2; R17 is H or CH3; R18 is H, C1-C3 alkyl, Cl, Br, OCH3 or OC2H5; R19 is H, C1-C4 alkyl, OCH3, F, Br, C1, CF3, CN, NO2, SO2CH3, SCH3 or N(CH3)2; A is Image A-1 A-2 A-3 Image A-4 A-5 A-6 Image A-7 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)alkylamino; 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)alkylamino, C3-C4 alkenyloxy, C3-C4 alkynyloxy C2-C5 alkylsul- finylalkyl, C1-C4 haloalkyl, C2-C5 alkylsul- fonylalkyl, C3-C5 cycloalkyl, C2-C4 alkynyl, C2-C5 alkylthioalkyl, Image N(OCH3)CH3; W3 and W4 are independently O or S; q is 2 or 3; Rd is H or CH3; Re is C1-C2 alkyl; Rf i8 C1-C2 alkyl; Z 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 3; Y3 is H or CH3; Z1 is CH or N; 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 W is S, then R is H, A is A-1, and Y is CH3, OCH3, OC2H5, CH2OCH3,C2H5, CF3, SCH3, OCH2CH=CH2, OCH2C?CH, OCH2CH2OCH3, CH(OCH3)2 Image b) when X is Cl, Br, F or I, then Z is CH and Y is OCH3, OC2H5, NH2, NHCH3, N(CH3)2 or OCF2H; c) when X or Y is C1 haloalkoxy, then Z is CH; d) the combined total number of carbon atoms of R15 and R16 is less than or equal to 10; e) when R15 is CH2CN or CH2CH2CN, then R16 is CH2CN or CH2CH2CN; f) when R15 is OCH3 or OC2H5, then R16 is H or CH3; g) when E is -CH2-, then n is O; h) when the total number of carbon atoms of X and Y is greater than four, then the number of car- bons of R1 is less than or equal to two, the number of carbons of R2 is less than or equal to two, and the number of carbons of Q is less than or equal to four; and i) X4 and Y4 are not simultaneously Cl.
510106
E. I. Du Pont de Nemours And Company
Mccallum Brooks & Co.
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