furan - 3 - karboxamidderivat with fungicidal effect jemte seen to framstella them

摘要

1303844 Furan-3-carboxamide derivatives UNIROYAL Ltd 9 Feb 1970 [13 Feb 1969] 6083/70 Heading C2C Furan-3-carboxamide derivatives represented by the general formula wherein X, Y and Z are the same or different and are selected from H, amino, alkyl, substituted alkyl, alkenyl, phenyl or substituted phenyl or Y and Z together are , #-alkylene; R 1 is selected from phenyl, substituted phenyl, benzyl, biphenylyl, alkyl, alkenyl, cycloalkyl, naphthyl, pyridyl, thiazolyl, ethylene bis- or furfuryl, or R and R 1 together with the N atom to which they are attached form a morpholino group, possess good fungicidal and insecticidal properties (as described in Specification 1,302,410). The above compounds are claimed per se with the provisos that (a) R 1 is not phenyl or tolyl when simultaneously, R and Y are H, X is methyl and Z is H or methyl; (b) R 1 is not phenyl when simultaneously, R and Z are H and X and Y are methyl; (c) R 1 is not phenyl solely substituted by nitro or in combination with one or more alkyl or alkoxy substituents when simultaneously, R, X, Y and Z are H; and (d) R 1 is not methyl when simultaneously R 1 and Y are methyl groups, and X and Z are H. The compounds may be prepared (i) by reacting an -hydroxyketone of formula Y.COCH(Z)OH with an acetamide of formula X.CO.CH 2 CONHR in an inert solvent in the presence of an active Friedel-Crafts reagent or (ii) by a multi-step method involving the reaction of an -chloroketone or an -hydroxyketone with ethyl acetoacetate to produce the furan-3-carboxylate; the conversion of this to the corresponding 3-furoic acid then to the 3-furoyl chloride which may be treated with an amine in an inert solvent to form the 3-carboxamide.