含1,3,4-噻二唑杂环的甲氧基丙烯酸酯类化合物的合成与杀菌活性研究

Synthesis and Fungicidal Activity of the Strobilurins Containing 1,3,4-Thiodiazole Ring

以多种取代苯甲酸为原料,通过酰化、醇解、肼解、亲核加成、脱水、亲核取代等多步反应,合成了16个未见文献报道的含1,3,4-噻二唑杂环的甲氧基丙烯酸酯类化合物,其结构均通过1H NMR,IR,MS,HRMS等予以表征确认,并对所有化合物进行了离体杀菌活性测试.结果表明:对水稻立枯和棉花枯萎病菌的防效好于番茄晚疫病菌,对西瓜炭疽病菌防效显著,其中化合物5a^5c,5g,6a^6c的抑制率均高于嘧菌酯,5g在100μg/mL下抑制率为77.5%.

Sixteen novel strobilurins containing 1,3,4-thiodiazole ring were synthesized by multi-step reactions including acylation, alcoholysis, hydrazinolysis, nucleophilic addition, dehydration and nucleophilic substitution from initial substituted benzoic acid and their structures were characterized by 1H NMR, IR, MS and HRMS. The results of bioassay indicated that the fungicidal activity of title compounds is better against Rhizoctonia solani Kühn and Fusarium oxysporum than Phytophthora infestans in vitro, while remarkably higher when against Colletetrichum orbiculare. Especially, compounds 5a～5c, 5g, 6a～6c displayed higer fungicidal activities than azoxystrobin, the inhibitory rate of 5g is 77.5% at the concentration of 100 μg/mL.