有机化学 ›› 2014, Vol. 34 ›› Issue (9): 1800-1805.DOI: 10.6023/cjoc201403026 上一篇    下一篇

研究论文

3,5-二取代的异噁唑啉类衍生物的合成及杀菌活性研究

宁国慧a, 赵温涛a, 边强b, 唐向阳a   

  1. a 天津大学理学院化学系, 天津 300072;
    b 南开大学国家农药工程研究中心, 天津 300071
  • 收稿日期:2014-03-11 修回日期:2014-04-19 发布日期:2014-05-07
  • 通讯作者: 唐向阳 E-mail:txy@tju.edu.cn
  • 基金资助:

    国家自然科学青年基金(No. 21205086)资助项目.

Synthesis and Fungicidal Activity of Some 3,5-Disubstituted Isoxazoline Derivatives

Ning Guohuia, Zhao Wentaoa, Bian Qiangb, Tang Xiangyanga   

  1. a Department of Chemistry, Tianjin University, Tianjin 300072;
    b National Pesticide Engineering Research Center, Nankai University, Tianjin 300071
  • Received:2014-03-11 Revised:2014-04-19 Published:2014-05-07
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21205086).

取代苯甲醛与盐酸羟胺反应生成取代苯甲醛肟,经氯代得到相应的氯代苯甲醛肟,再和N-乙烯基吡咯烷酮、2-乙烯基吡啶、4-乙烯基吡啶等进行1,3-偶极环加成反应,合成了15个未见报道的异噁唑啉类化合物. 其结构经过1H NMR,13C NMR及高分辨质谱表征. 初步的生物活性测试结果表明,目标化合物3b对黄瓜灰霉表现出了很好的防效,化合物3c对番茄早疫、花生褐斑和油菜菌核表现出了很好的防效,化合物3e~3o对花生褐斑、苹果轮纹、番茄早疫、小麦赤霉、辣椒疫霉、油菜菌核、水稻纹枯等7种真菌具有很好的防效,表现出了广谱的抑菌活性.

关键词: 1,3-偶极环加成, 异噁唑啉, 合成, 结构表征, 杀菌活性

Various substituted benzaldehydes reacted with hydroxylamine hydrochloride, followed by the chlorination with N-chlorosuccinimide (NCS), to form the corresponding chlorobenzaldehyde oximes, which then underwent the 1,3-dipolar cycloaddition reaction with N-vinylpyrrolidone, N-vinylpyridine and 4-vinylpyridine, respectively, to generate fifteen novel compounds containing isoxazoline ring. All the title compounds have been characterized by 1H NMR, 13C NMR, and HRMS. Preliminary biological activity tests in vitro indicated that compounds 3e~3o displayed excellent fungicidal activity against C. arachidicola, P. piricola, A. solani, F. graminearum, P. capsici, S. sclerotiorum, and R. solani in the test concentration, compound 3b displayed excellent fungicidal activity against B. cinerea, and compound 3c displayed excellent fungicidal activity against A. solani, C. arachidicola and S. Sclerotiorum.

Key words: 1,3-dipolar cycloaddition, isoxazoline, synthesis, structure characterization, fungicidal activity