GB1355349A - N,n-disubstituted amino -thio- carboximidic esters and salts thereof and their use as herbicides - Google Patents

Abstract

1355349 N,N-Amino(thio)carboximidic esters SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ NV 14 Sept 1971 [16 Dec 1970] 59718/70 Heading C2C The novel N,N-disubstituted amino(thio)carboximidic esters of the Formula I wherein Y represents a halogen, alkyl, haloalkyl or alkoxy radical; n is 0 or 1-5 (when n > 1 two or more substituents Y may be the same or different); A represents a bivalent radical derived from an alkane; X represents O or S; R<SP>1</SP> is phenyl; R<SP>2</SP> is H or a hydrocarbyl group; R<SP>3</SP> is a hydrocarbyl group optionally substituted by a halogen atom or a hydroxy group or is ethyl substituted by a group of Formula II and their salts may be prepared, in the case of compounds in which R<SP>2</SP> is H, by reacting a compound of Formula II with an alcohol, mercaptan, phenol or thiophenol and an acid optionally followed by conversion of the salt into the corresponding base. Compounds in which R 2 is other than hydrogen may be prepared by alkylation of a silver derivative of N-hydrocarbylcarbonamide having the functional group -CO-NHR<SP>2</SP>. 2 - (N - benzoyl - 3,4 - dichloroanilino)propionitrile, 2-(N-benzoyl-4-chloroanilino)propionitrile, 2 - (N - benzoyl - 4 - chloro - 3 - fluoroanilino)- propionitrile and 2-(N-benzoyl-4-fluoroanilino)- propionitrile are prepared by reaction of the corresponding 2-anilinopropionitrile with benzoyl chloride. Herbicidal compositions comprise a compound of Formula I together with a carrier and/or a surface active agent and optionally together with other known herbicides or pesticides.