含吡啶环的1,3,4-噁二唑衍生物的合成及生物活性研究  

Synthesis and Bioactivity of Pyridine Containing 1,3,4-Oxadiazole Derivatives

作　　者：范志金[1] 刘斌[1] 刘秀峰[1] 钟滨[1] 刘长令[1] 李正名[1] 

机构地区：[1]南开大学元素有机化学研究所,元素有机化学国家重点实验室,天津300071

出　　处：《高等学校化学学报》2004年第4期663-666,共4页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金 (批准号 3 0 2 70 883 );国家重点基础研究发展计划"九七三"项目 (批准号 :2 0 0 3CB114 40 6)资助

摘　　要：依据生物电子等排原理 ,在分子中同时引入吡啶环和 1 ,3 ,4-二唑杂环合成了 5 -( 3 -吡啶基或 4-吡啶基 ) -1 ,3 ,4-二唑 2 -硫乙酸胺类化合物 ,用 1H NMR,IR,质谱和元素分析对其结构进行了表征 .离体试验表明 ,化合物 B1— 5小麦赤霉病菌和苹果轮纹病菌的抑制率分别为 3 0 %和 42 % ,化合物 B1 -6对苹果轮纹病菌的抑制率为 3 8% .除草活性实验结果表明 ,化合物 B1 -6对油菜和稗草具有较高的抑制作用 .1,3,4-Oxadiazole containing heterocyclic compounds and pyridine containing compounds are associated with diverse biological activities of antiinflammation, antibacter and pesticide bioactivity. In order to find leading compound with an excellent fungicide activity, a series of 5-(pyridin-3′-yl- or 4′-yl-)-1,3,4 oxadiazole-2-thioacetamides were designed and synthesized according to the biological isosterism by introducing pyridine and 1,3,4-oxadiazole moiety and thioacetamide group in one molecule. The target compounds were synthesized by reaction of N-substituted chloroacetamide with 2-mercapto-5-(pyridin-3′-yl- or 4′-yl-)-1,3,4-oxadiazole which was prepared by the reaction of CS 2 and 3-pyridinoyl or 4-pyridinoyl. The structures of all compounds synthesized were determined by 1H NMR , IR, MS and elemental analysis. Bioasscay indicated that, all compounds synthesized had no fungicidal activity, some compounds such as B1-6 possessed satisfactory activity of growth inhibition against Echinochloa crusgalli and Brassica napus. Pot examination of soil treatment revealed that, fresh weight inhibition of compound B1-4 and B1-6 against Brassica napus was not obvious, however, Brassica napus had distinct symptom of phototoxicity, leaf curl and marginal scorch were observed.

关 键 词：吡啶环 1 3 4-噁二唑衍生物 合成 生物活性 生物电子等排原理 杀菌剂 

分 类 号：TQ455.47[化学工程—农药化工] O626.321[理学—有机化学]