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

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.

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

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.