应用化学 ›› 2015, Vol. 32 ›› Issue (2): 151-157.DOI: 10.11944/j.issn.1000-0518.2015.02.140163

• 研究论文 • 上一篇    下一篇

含吡唑1,2,4-三唑噻二嗪衍生物的合成及抑菌活性

郑玉国*, 郭晴晴, 周莉, 李世杰, 余忠林, 刘翠菊, 熊香   

  1. 兴义民族师范学院 绿色化学合成技术研究所 民族药用生物资源研究与开发实验室 贵州 兴义 562400
  • 收稿日期:2014-05-06 修回日期:2014-07-21 出版日期:2015-02-10 发布日期:2015-02-10
  • 通讯作者: 郑玉国, 副教授; Tel:0859-3222483; E-mail:yuguobaolong@163.com; 研究方向:新农药的创制研究
  • 基金资助:
    贵州省教育厅自然科学研究(2010090)资助项目;贵州省高等学校教学质量与教学改革工程资助项目(黔教高发[2011]281号,[2012]426号),[2013]446号);兴义民族师范学院自然科学重点资助项目(llxyy202)

Synthesis and Biological Activity of Novel 1,2,4-Triazolothiadiazine Derivatives Containing Pyrazole Unit

ZHENG Yuguo*, GUO Qingqing, ZHOU Li, LI Shijie, YU Zhonglin, LIU Cuiju, XIONG Xiang   

  1. Institute of Green Chemistry-Synthesis Technology,Key Laboratory of Research and Development of Ethnomedicinal Biological Resources,Xingyi Normal University for Nationalities,Xingyi,Guizhou 562400,China
  • Received:2014-05-06 Revised:2014-07-21 Published:2015-02-10 Online:2015-02-10
  • Contact: Corresponding author:ZHENG Yuguo, associate professor; Tel:0859-3222483; E-mail:yuguobaolong@163.com; Research interests:design and research of novel pesticide
  • Supported by:

    Supported by Natural Science Foundation of Guizhou Province(No.2010090), the Promotion Project of Higher Education of Guizhou Province(No.[2011]278), Higher Educational Quality and Reform Project of Guizhou Province(No.[2011]281, No.[2012]426, No.[2013]446), the Natural Science Foundation of Xingyi Normal University for Nationnality(No.llxyy202)

摘要:

1-苯基-3-甲基-5-氯-4-吡唑甲醛与4-氨基-5-取代苯基-1,2,4-三唑-3-硫酮缩合生成4-(1-苯基-3-甲基-5-氯吡唑次甲亚胺基)-5-(取代苯基)-2H-1,2,4-三唑-3(4H)-硫酮,再烷基加成化为新型含吡唑基5,6-2H-1,2,4-三唑[3,4-b][1,3,4]噻二嗪衍生物。 化合物结构经1H NMR、IR以及元素分析确认。 初步生物活性测试结果表明,在100 mg/L浓度下,化合物8a(3-(2-甲基苯基)-6-(5-氯-2-甲基-4-苯基吡唑)-7-(4-硝基苯基)-5H-1,2,4-三唑[3,4-b][1,3,4]噻二嗪)对黄瓜炭疽病的抑制率达90%。

关键词: 吡唑, 三唑[3, 4-b][1, 3, 4]噻二嗪, 合成, 生物活性

Abstract:

A series of 4-(1-phenyl-3-methyl-5-chloro-1H-pyrazolelideneamino)-5-(substituted aryl)-2H-1,2,4-triazole-3(4H)-thiones was synthesized by the condensation reaction of 5-chloro-1-phenyl-3-methyl-1H-pyrazole-4-aldehyde with 4-amino-5-(substituted phenyl-2H-1,2,4-triazole-3(4H)-thione. Alkylation of compound 6 with ethyl-2-chloroacetate or 1-(chloromethyl)-4-nitrobenzene afforded 5,6-2H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine derivatives containing pyrazole unit. Their structures were confirmed by 1H NMR, IR and elemental analyses. Preliminary bioassay indicates that the anti-fungicidal activity of compound 8a(3-(2-methyphenyl)-6-(5-chloro-2-methyl-4-phenylpyrazole)-7-(4-nitrophenyl)-5H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine) to Colletotrichum lagenarium at the concentration of 100 mg/L is 90%.

Key words: pyrazo, triazolo[3, 4-b][1, 3, 4]thiadiazine, synthesis, bioactivity

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