高等学校化学学报 ›› 2004, Vol. 25 ›› Issue (4): 663.

• 研究论文 • 上一篇    下一篇

含吡啶环的1,3,4-噁二唑衍生物的合成及生物活性研究

范志金, 刘斌, 刘秀峰, 钟滨, 刘长令, 李正名   

  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
  • 收稿日期:2003-03-07 出版日期:2004-04-24 发布日期:2004-04-24
  • 通讯作者: 范志金(1968年出生),男,博士,副教授,主要从事农药化学和农药生物学方面的研究.E-mail:fanzj@nanka.iedu.cn E-mail:fanzj@nanka.iedu.cn
  • 基金资助:

    国家自然科学基金(批准号30270883);国家重点基础研究发展计划“九七三”项目(批准号:2003CB114406)资助

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

FAN Zhi-Jin, LIU Bin, LIU Xiu-Feng, ZHONG Bin, LIU Chang-Ling, LI Zheng-Ming   

  1. State Key Laboratory of Elemento Organic Chemistry, Institute of Elemento Organic Chemistry, Nankai University, Tianjin 300071, China
  • Received:2003-03-07 Online:2004-04-24 Published:2004-04-24

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-噁二唑杂环合成了5-(3-吡啶基或4-吡啶基)-1,3,4-噁二唑2-硫乙酸胺类化合物,用1HNMR,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30%和42%,化合物B1-6对苹果轮纹病菌的抑制率为38%.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.

关键词: 1, 3, 4-噁二唑, N-取代氯乙酰胺, 吡啶, 生物活性

Abstract: 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 CS2 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.

Key words: 1,3,4-Oxadiazole, N-substituted chloroacetamide, Pyridine, Bioactivity

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