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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (08): 999-1006. 上一篇    下一篇

研究论文

新型氨基甲酸含氮杂环甲基酯的合成及生物活性研究

唐子龙*,a,b，刘汉文a，王晓光b，欧晓明b，唐仁和a，陈奕彬a   

  1. (a湖南科技大学化学化工学院 分子构效关系湖南省高校重点实验室 湘潭 411201)
    (b湖南化工研究院 国家农药创制工程技术研究中心 长沙 410007)
  • 收稿日期:2007-02-28 修回日期:1900-01-01 发布日期:2007-07-30
  • 通讯作者: 唐子龙*

Synthesis and Biological Activity Studies on Novel O-Cycloaminomethyl Carbamates

TANG Zi-Long*,a,b, LIU Han-Wena, WANG Xiao-Guangb, OU Xiao-Mingb
TANG Ren-Hea, CHEN Yi-Bina   

  1. (a Hunan Provincial University Key Laboratory of QSAR/QSPR, School of Chemistry and Chemical Engineering,
    Hunan University of Science and Technology, Xiangtan 411201)
    (b National Engineerin Research Center of Agrochemicals, Hunan Research Institute of Chemical Industry,
    Changsha 410007)
  • Received:2007-02-28 Revised:1900-01-01 Published:2007-07-30
  • Contact: TANG Zi-Long*

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1091

被引次数

8 | 3

常规加热或微波照射下, 含氮杂环1与多聚甲醛反应以良好的产率生成含氮杂环基甲醇3, 反应物物质的量的比、反应温度等对反应产率有影响, 微波条件下的反应时间比常规加热下大大缩短. 化合物3和异氰酸酯4在常规加热或微波照射下生成相应的氨基甲酸含氮杂环甲基酯5a～5m. 反应温度、反应物物质的量的比、反应时间、微波辐射功率等对反应产率都有一定的影响, 与常规加热相比微波条件下的反应时间大大缩短. 化合物5的结构经过IR, 1H NMR, MS, 元素分析测定, 部分化合物经过13C NMR测定. 测定了化合物5的杀虫和除草活性, 结果表明其杀虫活性较低, 除草活性高于杀虫活性, 5a, 5d, 5e和5m对苋菜和黄瓜的防除率高达100%.

关键词: 氮杂环化合物, 除草活性, 氨基甲酸酯, 杀虫活性, 合成

Under conventional heating or microwave irradiation, reactions of nitrogen-containing heterocycles 1 with paraformaldehyde gave cycloaminomethanols 3 in good yields. It was found that the ratio of reactants and reaction temperature affected the reaction yield, and the reaction time under microwave irradiation was much shorter than with the one under the conventional heating. The resulting intermediates 3 reacted easily with isocyanates 4 under conventional heating or microwave irradiation to give the corresponding O-cycloaminomethyl carbamates 5a～5m. The structure of compounds 5 was characterized with IR, 1H NMR, MS spectra and elemental analysis, and some of them were further characterized with 13C NMR. The insecticidal activity and herbicidal activity of compounds 5 showed that the insecticidal activity was quite lower than the herbicidal activity, and compounds 5a, 5d, 5e and 5m exhibited control efficacy of up to 100% against Cucumis sativm or Amaranthus sp.

Key words: insecticidal activity, carbamate, herbicidal activity, synthesis, nitrogen-containing heterocycle