2-多氟烷基取代和葡萄糖基取代的2,4-二氢-1,2,4-三唑-3-硫酮类席夫碱的合成及其杀虫活性  

Synthesis and Insecticidal Activity of 2-Perfluoroalkyl-substituted or Glucopyranosyl-substituted 2,4-Dihydro-1,2,4-triazole-3-thione Schiff Base

作　　者：尹凯[1] 蒋历辉[2] 周后相[1] 黄勇[1] 向建南[1] 

机构地区：[1]湖南大学化学化工学院,长沙410082 [2]中南大学化学化工学院,长沙410083

出　　处：《有机化学》2008年第6期1016-1023,共8页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No20472018);高等学校博士学科点专项科研基金(No20060532022)资助项目

摘　　要：为改善三唑类化合物的生物活性,以5-苯基-4-氨基-1,2,4-三唑-3-硫酮为原料,将其与芳香醛在冰醋酸体系中反应,得到5-苯基-4-芳基亚甲氨基-1,2,4-三唑-3-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2,4-二氢-1,2,4-三唑-3-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1HNMR,19FNMR,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.To improve their biological activities of triazole derivatives, 5-phenyl-4-（benzylideneamino）- 2,4-dihydro-1,2,4-triazole-3-thione Schiff bases （4a～4i） were synthesized by the reaction of 5-phenyl- 4-amino-2,4-dihydro-1,2,4-triazole-3-thione with aromatic aldehydes in glacial acetic acid medium. On the basis of these Schiff bases, a series of 1-perfluoroalkyl-substituted or glycopyranosyl-substituted 2,4-dihydro- 1,2,4-triazole-3-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.

关 键 词：多氟烷基 葡萄糖基 1 2 4-三唑 合成 杀虫活性 

分 类 号：TQ450.21[化学工程—农药化工]