C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/249, 260/251
C07D 401/04 (2006.01) A01N 47/36 (2006.01) C07D 491/044 (2006.01) C07D 521/00 (2006.01)
Patent
CA 1308101
Title HERBICIDALPYRIDINESULFONYLUREAS Abstract This invention relates to herbicidal pyridine- sulfonylureas, which re highly active as preemergence and postemergence herbicides, of the following: Image wherein Image J-l J-2 J-3 Image J-4 J-5 R is H or CH3; W is O or S; R1 is Rf or Rg; Rf is H, C1-C3 alkyl, C1-C3 haloalkyl, halogen, NO2, C1-C3 alkoxy, C1-C3 alkylthio or CN; Rg is C1-C3 haloalkyl, C2-C3 alkyl, cyclopropyl, C1-C3 alkyl substituted by C1-C3 alkoxy, OH, C1-C2 alkylthio or CN, CN, W2R11, amino, C1-C3 alkylamino or C1-C3 dialkylamino; R2 is C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C5 cycloalkylthio, C3-C5 cycloalkylsulfinyl, C3-C5 cycloalkylsulfonyl, SO2NH2, SO2NRdRe, SO2NR'7R8, SO2NR7R8, OSO2R8, SO2OR8, N3, P(Wl)(OC1-C2 alkyl)2, CN, CO2R9, CO2R'9, CH2F, CF2H, CH2Cl, CCl2H or C2-C4 haloalkyl; R3 is C1-C4 alkylsulfinyl, C3-C5 cycloalkylthio, C3-C5 cycloalkylsulfinyl, C3-C4 cycloalkylsul- fonyl, SO2NH2, SO2NRdRe. SO2NR7R8, SO2NR'7R8, OSO2R8, SO2OR8, N3, P(W1)(OC1-C2 alkyl)2, CN, CO2R9, CO2R'9 or C1-C4 haloalkyl; R4 is C1-C4 alkylsulfinyl, C3-C5 cycloalkylthio, C3-C5 cycloalkylsulfinyl, C3-C4 cycloalkylsul- 2NH2, SO2NRdRe, S°2NR7R8' OSO R , SO2OR8, N3, P(W1)(OC1-C2 alkyl)2, CN, CO2R9 or C1-C4 haloalkyl; R5 is C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C5 cycloalkylthio, C3-C5 cycloalkylsulfinyl, C3-C5 cycloalkylsulfonyl, SO2NH2, SO2NRdRe, SO2NR7R8, OSO2R8, SO2OR8, N3, P(W1)(OC1-C2 alkyl)2, CN, CO2R9 or C1-C4 haloalkyl; R6 is C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C3-C4 alkenylthio, C3-C4 alkenylsulfinyl, C3-C4 alkenylsulfonyl, C3-C4 alkynylthio, C3-C4 alkynylsulfinyl, C3-C4 alkynylsulfonyl, C3-C5 cycloalkylthio, C3-C5 cycloalkylsulfinyl, C3-C5 cycloalkylsulfonyl, SO2NRdRe, SO2NR7R8, OSO2R8, SO2OR8, N3, P(W1)(OC1-C2 alkyl)2, CN, CO2R9 or C1-C4 halo- alkyl; R7 is H, C2-C3 cyanoalkyl, C3-C4 alkenyl or C3-C4 alkynyl; R'7 is C1-C4 alkyl; R8 is C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C3-C4 alkynyl, C2-C4 alkoxyalkyl or cyclo- propyl; or R7 and R8 may be taken together as -(CH2)3-, -(CH2)4-, -(CH2)5- or -CH2CH2OCH2CH2-; R9 is CH2CH2R10, CH2CF3, C3-C4 halOalkyl, C3-C4 alkynyl, C2-C4 alkylthioalkyl, C3-C5 cycloalkyl or C4-C7 cycloalkylalkyl; R9' i6 C1-C4 alkyl, C3-C4 alkenyl, CH2CH2Cl, CH2CH2Br, CH2CH2OCH3 or CH2CH2OC2H5; R10 is OH, F, CN, OSO2(C1-C3 alkyl) or OSO2(C1-C3 haloalkyl); R1l is C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 alkenyl or C3-C4 alkynyl; W1 is O or S; W2 is O or S; A is Image A-1 A-2 A-3 A-4 Image or A-5 A-6 A-7 X is H, C1-C4 alkyl, C1-C4 alkoxy. C2-C4 halo- alkoxy, C1-C4 haloalkyl, C2-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, C2-C4 halo- alkoxy, C2-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, C2-C5 alkylsulfinylalkyl, C2-C5 alkyl- sulfonylalkyl, C1-C4 haloalkyl, C2-C4 alkynyl, C3-C5 cycloalkyl, azido, Image N(OCH3)CH3; m is 2 or 3; Q1 and Q2 are independently O or S; Ra is H or C1-C3 alkyl; Rb and Rc are independently C1-C3 alkyl; Rd is H or C1-C2 alkyl; Re is C1-C2 alkoxy; 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; X4 is CH3, OCH3, OC2H5, CH2OCH3 or Cl; Y4 is CH3, OCH3, OC2H5 or Cl; and their agriculturally suitable salts; provided that 1) when X is halogen, then Z is CH and Y is OCH3, OC2H5, NH2, NHCH3, N(CH3)2 or N(OCH3)CH3; 2) 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, OCH2CH2OCH3, CH(OCH3)2 or Image ; 3) when the total number of carbon atoms of X and Y is greater than four, then the combined number of carbons of R1, R2, R3, R4, R5 or R6 is less than or equal to six; 4) when J is J-1 and R2 is C1-C4 alkylsulfinyl C1-C4 alkylsulfonyl, SO2NRdRe, SO2RN?R8 or CO2R?, or when J is J-2 and R3 is CF3, SO2NRdRe, SO2RN?R8, C1-C4 alkylsulfinyl or CO2R?, then Y is other than C2-C5 alkylthioalkyl, C2-C5 alkylsulfinylalkyl, C2-C5 alkylsulfonylalkyl, Image or Image ; 5) when J is J-2 or J-3 and R3 or R4 is C1-C4 alkylsulfinyl, then X and Y are other than NH2 or NHCH3; 6) when J is J-2 and R3 is C1-C4 alkylsulfinyl or SO2NRdRe, or R7 is H, then X and Y are other than C2-C4 haloalkoxy; 7) when J is J-5, then R7 is other than H and R6 is other than SO2NRdRe; 8) when J is J-2 and R3 is SO2NH2 or SO2NRdRe, or R7 is H, then X is other than iodine; 9) when J is J-2 and R7 is H or R3 is SO2NRdRe, then Y is other than C2-C4 alkynyl; 10) X4 and Y4 are not simultaneously Cl; 11) when J is J-1, J-2, J-3, J-4 and A is A-5, then Rf is other than H; 12) when J is J-1 or J-2, then A is other than A-6; 13) when J is J-1 and A is A-7, then R2 is other than C1-C4 alkysulfonyl; 14) when R2 or R3 is CO2R'9 or SO2NR'7R8, then R1 is Rg and when R2 or R3 is other than CO2R'9 or SO2NR'7R8, then R1 is Rf; and 15) when J is J-2 and R1 is adjacent to the sulfonylurea bridge, then Rg is C1-C3 haloalkyl. C2-C3 alkyl, cyclopropyl, CN, W2R11, amino, C1-C3 alkylamino or C1-C3 dialkylamino.
553474
E. I. Du Pont de Nemours And Company
Sim & Mcburney
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