Herbicidal n,n-di:substd. 2-heterocyclyl:oxy-acetamide derivs. prodn. - by reaction of n,n-di:substd. 2-hydroxy- or 2-acyloxy-acetamide cpds. with heterocyclyl halide(s)

摘要

In the prodn. of N,N-disubstd.-2- heterocyclyloxy-acetamide derivs. R10-CH2-CO-NR3-(O)n-R2 (I), an N,N-disubstd.-2- (hydroxy or acyloxy) acetamide deriv. RO-CH2-CO-NR3-(O)n-R2 (II) is reacted with a heterocyclyl halide R1-Hal (III) at -10 to +110 deg. C in the presence of an acid binding agent using water as diluent, opt. in the presence of a phase-transfer catalyst. (where R1 is a 5-membered heterocycle contg. an O- or S-atom and 1-3 N-atoms, opt. substd. by halogen, CN, NO2, NH2, alkylamine, arylamino, dialkylamino, alkanamido, alkanoyl, carboxy, alkoxycarbonyl, carbamoyl, alkylamino- carbonyl, dialkylaminocarbonyl opt. substd. arylaminocarbonyl, opt. subst. aryl, opt. halo-substd. aralkyl, alkoxy, alkenyloxy, alkynyloxy, alkoxycarbonyloxy, aralkoxy, aryloxy, alkylthio, alkenylthio, alkynylthio, alkoxycarbonyl- alkylthio, aralkylthio, arylthio, alkylsulphonyl, alkyl- sulphinyl or alkyl, alkenyl, alkynyl, alkoxyalkyl, aralkoxy- alkyl, aryloxyalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, arylthioalkyl, arylsulphinylalkyl, arylsulphonylalkyl, carboxyalkyl, alkoxycarbonylalkyl, opt. substd. aminocarbonylalkyl, cyanoalkyl or cycloalkyl (opt. fused with a opt. substd. benzo or R1 is tetrazolyl opt. substd. by an opt. substd. phenyl, n is O or 1; and R2 and R3 are each alkyl, alkenyl, alkynyl, cycloalk(en)yl- aralkyl or aryl; or (when n is O) N(R2)(R3) is an opt. substd., opt. partially unsatd. and opt. benzo-fused mono- or bicycle opt. contg. further heteroatoms; Hal is F, Cl, Br or I; and R is H or -CO-Z in which Z is H, alkyl, cycloalkyl, haloalkyl, alkoxy- alkyl or aryl). Useful as herbicides. Process gives high yields. Prods. generally crystallise from reaction mixt. simplifying working up. Purity is high.