Patent CA-1259613-A (CA)
IPC: C07D409/14
Filed: 1987-09-24
Granted: 1989-09-19
Abstract: Title HERBICIDAL ACETALS AND KETALS      Abstract of the Disclosure This invention relates to novel furan- and thiophenesulfonamides such as 3-(1,3-dioxolan-2-yl)-N-[(4-methoxy-6-methyl-1,3-5-triazin-2-yl)aminocarbonyl]-2-thiophenesulfonamide and N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-(1,3-dioxolan-2-yl)-2-thiophene-sulfonamide which are highly active pre-emergent and/or post-emergent herbicides.  More specifically, the herbicides are of the formula:       I wherein Q is                             ,           ,                or   R is H or CH3:            R1 is           ,      or      E is CH2 or a single bond: R2 is H, C1-C2 alkyl or C1: R3 is H, C1-C3 alkyl or C1-C3 alkoxy: R4 is R5 are independently C1-C2 alkyl: R6 and R7 are independently H or C1-C2 alkyl: W is O or S: W1 is O or S: Q1 and Q2 are independently O, S or NCH3:            A is             ,     ,            ,             ,          or   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, halogen. C2-C5 alkoxyalkyl, C2-C5 alkoxyalkoxy. amino, C1-C3 alkylamino, di(C1-C3)alkylamino, C3-C4, alkenyloxy, C3-C4 alkynyloxy, C2-C5 alkyl-sulfinylalkyl, C1-C4 haloalkyl, C2-C5 alkyl-sulfonylalkyl. C3-C5 cycloalkyl. C2-C4 alkynyl, C2-C5 alkylthioallsyl. C(O)R8,    ,        ,   or N(OCH3)CH3: m is 2 or 3: L1 and L2 are independently O or S: R8 is H or CH3: R9 and R10 are independently C1-C2 alkyl: R11 is C1-C3 alkyl R12 is H. F. C1, NO2. C1-C2 alkyl, C1-2 alkoxy C1-C2 alkylthio, C1-C2 alkylsulfinyl, C1-C2 alkyl-sulfonyl. di(C1-C2)alkylsulfamoyl or CO2(C1-C2 alkyl): R13 is H, C1-C2 alkyl,  C1-C2 alkoxy, C1, F or NO2; R14 is H, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 halo-alkyl, C1-C3 haloalkoxy, C1, Br, F, NO2, di(C1-C3)alkylsulfamoyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, amino, C1-C3 alkylamino, di(C1-C3)alkylamino, CH2OCH3, CH2SCH3 or CH2CN. Z is CH or N; Y1 is O or CH2; X1 is CH3, OCH3, OC2H5 or OCF2H; and Y2 is H or CH3;    X2 is CH3, C2H5 or CH2CF3; Y3 is OCH3, OC2H5, SCH3, SC2H5, OCF2H, SCF2H, CH3 or C2M5; X3 is CH3 or OCH3; Y4 is CH3, OCH3, OC2H5 or C1; and X4 is CH3, OCH3, OC2H5, CH2OCH3 or C1; and their agriculturally suitable salts; provided that a) when X is C1, F, Br, or I, then Z is CH and Y is OCH3, OC2H5, N(OCH3)CH3, NHCH3, N(CH3)2 or OCF2H; b) when Y is cyclopropyl, X is other than C1, F, Br or I; c) when R3 is C1-C3 alkoxy, then Q1 and Q2 are oxygen; d) when R3 is H or C1-C3 alkyl, then Q is Q-1 through Q-9; e) when X or Y is OCF2H, then Z is CH; f) when the total number of carbon atoms of X and Y is greater than four, then the combined number of carbons of the substituents on Q is less than or equal to ten; g) when W is S, then A is A-1, R is H, and Y is CH3, OCH3, OC2H5, CH2OCH3, C2H5, CF3, SCH3, OCH2CH=CH2, OCH2C?CH, OCH2CH2OCH3, CH(OCH3)2 or  ; h) when A is A-7 and Z is N, then R3 is C1-C3 alkoxy; i) when E is CH2, then R14 is H, CH3, OCH3, C1 or NO2 and is not in the 4-position.