2-氰基-3-取代氨基-3-(2-甲基苯基)丙烯酸乙酯的合成和杀菌活性

Synthesis and Fungicidal Activity of Ethyl 2-Cyano-3-substituted Amino-3-(2-methylphenyl)propenoate

2-甲基苯甲酰氯与氰乙酸乙酯反应得到2-氰基-3-羟基-3-(2-甲基苯基)丙烯酸乙酯,经氯化得到2-氰基-3-氯-3-(2-甲基苯基)丙烯酸乙酯,再用三乙胺处理合成了11个2-氰基-3-取代氨基-3-(2-甲基苯基)丙烯酸乙酯类目标化合物.生物活性研究表明这类新化合物具有良好的杀菌活性.

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.