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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (2): 356-360. 上一篇    

研究简报

N-(取代对三氟甲基苯基)-N'-(1,3,5-三取代)吡唑-4-羰基硫脲的合成与生物活性

杜海堂*,a,b，杜海军c，欧阳贵平d   

  1. (a天津大学理学院化学系 天津 300072)
    (b贵阳学院生物与环境工程系 贵阳 550005)
    (c贵州民族学院化学与环境科学学院 贵阳 550025)
    （d贵州大学精细化工开发中心 贵阳 550025)
  • 收稿日期:2007-04-05 修回日期:2007-08-16 发布日期:2008-02-01
  • 通讯作者: 杜海堂

Synthesis and Biological Activity of N-(Substituted-p-trifluoromethyl-phenyl)-N'-(1,3,5-trisubstitutedpyrazol-4-yl-carbonyl)thioureas

DU Hai-Tang*,a,b,DU Hai-Junc,OUYANG Gui-Pingd   

  1. (a Department of Chemistry, College of Sciences, Tianjin Universty, Tianjin 300072)
    (b Department of Biology and Environment Technology, Guiyang Col-lege, Guiyang 550005)
    (c School of Chemistry and Environment Science, Guizhou University for Nationalites, Guiyang 550025)
    (d Research and Development Center of Fine Chemicals, Guizhou University, Guiyang 550025)
  • Received:2007-04-05 Revised:2007-08-16 Published:2008-02-01
  • Contact: DU Hai-Tang

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为了寻找高效低毒的农药, 从3-甲基-1-取代苯基-5-吡唑酮出发, 经过几步反应得到5-氯-3-甲基-1-取代苯基-4-吡唑羰基异硫氰酸酯. 5-氯-3-甲基-1-取代苯基-4-吡唑羰基异硫氰酸酯分别与对三氟甲基苯胺和2,6-二氯-4-三氟甲基苯胺反应得到10个未见文献报道的N-(取代对三氟甲基苯基)-N'-(1,3,5-三取代)吡唑-4-羰基硫脲类化合物, 其结构经元素分析, IR, 1H NMR确证. 初步生物活性测试结果表明部分化合物有一定的杀菌活性.

关键词: 吡唑羰基硫脲, 对三氟甲基苯胺, 杀菌活性, 合成

In order to search for pesticides with high biological activity and low toxicity, 5-chloro-3-methyl-1-(p-substituted phenyl)pyrazole-4-carbonyl isothiocyanate was first obtained by a series of reactions starting from 3-methyl-1-(p-substituted phenyl)pyrazol-5-one, and then 5-chloro-3-methyl-1- (p-substituted phenyl)pyrazole-4-carbonyl isothiocyanate reacted with respec-tive p-trifluoromethylaniline and 2,6-dichloro-4-trifluoromethylaniline to yield ten new N-(substituted-p-trifluoromethylphenyl)-N'-(1,3, 5-trisubstituted pyra-zol-4-yl-carbonyl)thiourea derivatives 5a～5e and 6a～6e. Their struc-tures were characterized by IR, 1H NMR spectra and elemental analysis. Preliminary bioassays indicated that some compounds had fungicidal activity.

Key words: p-trifluoromethylaniline, pyrazolecarbonylthiourea, fungicidal activity, synthesis