Synthesis and fungicidal activity of ethyl 2-cyano-3-substituted amino-3-(2-methylphenyl)propenoate

11 novel Z-ethyl 2-cyano-3-substituted amino-3-(2-methylphenyl)propenoate were synthesized through three steps: the first one involved reaction of ethyl cyanoacetate with 2-methylbenzoylchloride to yield ethyl E-2-cyano-3-hydroxy-3- (2-methylphenyl)propenoate, which then reacted with phosphoroxychloride in the presence of triethylamine to afford a mixture of ethyl E- and Z-3-chloro-2-cyano-3-(2-methylphenyl)propenoate, and finally treatment of this mixture with ammomia or primary amines gave the title compounds. Their structures were confirmed by MS and ¹H NMR spectra. Biological activity evaluation showed that some of them exhibited fungicidal activities.