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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (06): 1016-1023. 上一篇    下一篇

研究论文

N-多氟烷基取代和葡萄糖基取代的1,2,4-三唑-5-硫酮类席夫碱的合成及其杀虫活性

尹凯a，蒋历辉b，周后相a，黄勇a， 向建南*,a   

  1. (a湖南大学化学化工学院 长沙 410082)
    (b中南大学化学化工学院 长沙 410083)
  • 收稿日期:2007-09-19 修回日期:2007-11-05 发布日期:2008-06-26
  • 通讯作者: 向建南

Synthesis and Insecticidal Activity of 1-Perfluoroalkyl-substituted or Glucopyranosyl-substituted 4,5-Dihydro-1,2,4-triazole-5-thione Schiff Base

YIN Kaia, JIANG Li-Huib, ZHOU Hou-Xianga, HUANG Yonga, XIANG Jian-Nan*,a   

  1. (a College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082)
    (b College of Chemistry and Chemical Engineering, Central South University, Changsha 410083)
  • Received:2007-09-19 Revised:2007-11-05 Published:2008-06-26
  • Contact: XIANG Jian-Nan

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为改善三唑类化合物的生物活性, 以3-苯基-4-氨基-1,2,4-三唑-5-硫酮为原料, 将其与芳香醛在冰醋酸体系中反应, 得到3-苯基-4-芳基亚甲氨基-1,2,4-三唑-5-硫酮类席夫碱(4a～4i). 在此基础上, 化合物4a～4i分别与多氟烷基碘代烷和溴代乙酰基葡萄糖反应合成了一系列1,2,4-三唑-5-硫酮类席夫碱的多氟烷基取代物5a～5r和葡萄糖基取代物6a～6d, 并用1H NMR, 19F NMR, IR和MS谱以及元素分析表征了它们的结构. 初步生物活性测试结果表明, 部分目标化合物具有明显的杀虫活性.

关键词: 多氟烷基, 杀虫活性, 葡萄糖基, 合成, 1,2,4-三唑

To improve their biological activities of triazole derivatives, 3-phenyl-4-(benzylideneamino)- 4,5-dihydro-1,2,4-triazole-5-thione Schiff bases (4a～4i) were synthesized by the reaction of 3-phenyl- 4-amino-4,5-dihydro-1,2,4-triazole-5-thione with aromatic aldehydes in glacial acetic acid medium. On the basis of these Schiff bases, a series of 1-perfluoroalkyl-substituted or gly-copyranosyl-substituted 4,5-dihydro- 1,2,4-triazole-5-thione Schiff bases (5a～5r, 6a～6d) were synthesized by the reaction of the Schiff bases with perfluoroalkyl iodides or 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide and confirmed by 1H NMR, 19F NMR, IR, MS techniques and elemental analysis. The results of preliminary bioassay showed that some title compounds possessed obvious insecticidal activity.

Key words: glucopyranosyl, insecticidal activity, 1,2,4-triazole, synthesis, perfluoroalkyl