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 239/42 (2006.01) C07D 251/12 (2006.01) C07D 521/00 (2006.01)
Patent
CA 1225643
1 - 6 Title BA-8590A HERBICAL ACETYLENIC PYRIMIDINES AND TRIAZINES Abstract of the Disclosure This invention relates to sulfonylureas derived from acetylenic pyrimidines and triazines, useful as pre- and postemergence herbicides. More specifically the sulfonylureas are of the formula: Image L wherein W1 is O or S; R is H or CH3; L is : Image , Image , Image , L-1 L-2 L-3 Image , Image , Image , L-4 L-5 L-6 Image Image , L-7 L-8 Image , Image , Image , L-9 L-10 L-11 2 - 6 Image , Image , Image , L-12 L-13 L-14 Image , Image , L-15 L-16 Image , Image , L-17 L-18 Image or Image ; L-19 L-20 R1 is OCH2CH2OCH3, CO2R17, SO2NR18R19, SO2N(OCH3)CH3, OSO2R20, WCF3, WCHF2, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C2 alkyl substituted with OCH3 or OCH2CH3, C6H 5, C3-C4 alkynyl, CH=CHCF3, CH=CHBr, or Q; 3 - 6 Q is Image , Image , Image , Image , Image , Q-1 Q-2 Q-3 Q-4 Q-5 Image , Image , Image , Image , Image , Q-6 Q-7 Q-8 Q-9 Q-10 Image , Image , Image , Image , Image , Image , Q-11 Q-12 Q-13 Q-14 Q-15 Q-16 Image , Image , Image , or Image ; Q-17 Q-18 Q-19 Q-20 R2 is H, F, Cl, Br, CF3, C1-C2 alkyl, C1-C2 alkoxy, C1-C2 alkylthio, C2-C3 alkoxyalkyl, C2-C3 alkyl- thioalkyl or OCF2H; R3 is H, CH3, OCH3, F, Cl, Br, SO2N(CH3)2, OSO2CH3 or S(O)nCH3; R4 is CH3, CH2CH3, OCH3, OCH2CH3, F, Cl, Br, SO2NR18R19, SO2N(OCH3)CH3, S(O)nR21, C3-C4 alkenyloxy, CH2OCH3 or CH2OCH2CH3; R5 is C1-C3 alkyl, F, Cl, Br, NO2, CO2R17, SO2NR18R19, SO2N(OCH3) or S(O)nR21; R6 is Cl, NO2, CO2CH3, CO2CH2CH3, SO2N(CH3)2, OSO2CH3, SO2CH3, SO2CH2CH3, OCH3 or OCH2CH3; R7 is H, CH3 or CH2CH3; R8 is H, CH3 or CH2CH3; 4-6 R9 is H or CH3; R10 is H or CH3; R11 is H or CH3; R12 is H, C1-C5 alkyl, C2-C3 alkoxycarbonyl, C2-C3 alkylcarbonyl, C1-C3 alkyl substituted by 1-3 halogens selected from 0-3 F, 0-3 Cl or 0-1 Br, C2-C4 alkyl substituted by OCH3, C3-C4 alkenyl, C3-C4 alkynyl or benzyl; R13 is H or C1-C3 alkyl; R14 is H or CH3; R15 is C1-C3 alkyl, F, Cl, Br, NO2, CO2R17 SO2NR18R19, SO2R21 or OCF2H; R16 is H, CO2CH3, CO2CH3CH3, SO2CH3 or SO2CH2CH3; R17 is C1-C4 alkyl, CH2CH2OCH3, CH2CH2Cl or CH2CH=CH2; R18 is H or C1-C3 alkyl; R19 is C1-C3 alkyl; R20 is C1-c3 alkyl or N(CH3)2; R21 is C1-C3 alkyl or CH2CH=CH2; R22 is H or C1-C3 alkyl; R23 is H or Cl; R24 is H or Cl; R25 is H or CH3; m is 0 or 1; n is 0 or 2; Q1 is 0, S, SO2 or NR14; Q2 is 0 or S; Q3 is S or NR22; W is 0, S or SO2: A is Image Image Image A-1 A-2 A-3 5-6 Image Image or A-4 A-5 X is H, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 halo- alkyl, C1-C3 haloalkoxy, C2-C4 alkoxyalkoxy, C1-C3 alkylamino, di(C1-C2 alkyl)amino, amino or cyclopropyl; Y is H, C1-C5 alkyl, Br, I, phenyl optionally substituted with CH3, OCH3, halogen, NO2, CF3 or SCH3, or C1-C3 alkyl substituted with OH, OCH3, OC2H5 or F; Z is CH or N; X1 is H or CH3; Y1 is 0 or CH2; X2 is CH3, CH2CH3 or CH2CF3; and Y2 is H or CH3; and their agriculturally suitable salts; provided that i) the total number of carbon atoms of R18 and R19 is less than or equal to four; ii) when m is 1, the R9 is H; iii) when L is L-17, then R13 and R14 are not simultaneously H; iv) when L is L-18, then R15, is adjacent to the sulfonylurea bridge SO2NHC(W1)N(R)A; v) when L is L-8 and Q1 is NR14, then m is 1; vi) when A is A-5 and L is L-1, L-2, L-3, L-4, L-5, L-6 or L-7 the X1 is H; vii) when the total number of carbon atoms of X and Y is greater than four, then the combined 6-6 number of carbons of the substituents on L is less than or equal to four; and (viii) when L is L-8, L-9, L-11, L-12, or L-17 and R is C -C alkoxyalkyl or C -C alkyl- thioalkyl, then Y is other than H or C -C alkyl.
488111
E. I. Du Pont de Nemours And Company
Mccallum Brooks & Co.
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