有机化学 ›› 2021, Vol. 41 ›› Issue (5): 2055-2062.DOI: 10.6023/cjoc202009042 上一篇    下一篇

研究论文

含芳基三氮唑结构的3-乙砜基吡啶类化合物的合成及杀虫活性研究

姚阳意a, 任朝丽a, 陈丽a, 钟良坤a,b, 许天明b,*(), 谭成侠a,*()   

  1. a 浙江工业大学化学工程学院 杭州 310014
    b 浙江省化工研究院有限公司 杭州 310023
  • 收稿日期:2020-09-18 修回日期:2020-12-14 发布日期:2021-02-22
  • 通讯作者: 许天明, 谭成侠
  • 基金资助:
    2011绿色农药协同创新中心(KYY-ZX-20170007)

Synthesis and Insecticidal Activity of 3-Ethyl Sulfone Pyridine Substituted Aryl Triazole Compounds

Yangyi Yaoa, Chaoli Rena, Li Chena, Liangkun Zhonga,b, Tianming Xub,*(), Chengxia Tana,*()   

  1. a College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014
    b Zhejiang Research Institute of Chemical Industry. Ltd., Hangzhou 310023
  • Received:2020-09-18 Revised:2020-12-14 Published:2021-02-22
  • Contact: Tianming Xu, Chengxia Tan
  • About author:
    * Corresponding authors. E-mail: ;
  • Supported by:
    Collaborative Innovation Center of 2011 Green Pesticide(KYY-ZX-20170007)

以3,6-二氯吡啶-2-羧酸为起始原料, 依据活性亚结构拼接原理, 设计合成了结构新颖的含芳基三氮唑结构的3-乙砜基吡啶类化合物, 所有目标化合物均经1H NMR, 13C NMR和HRMS结构表征. 初步杀虫活性测试结果表明, 在500 mg/L浓度下, 目标化合物均对玉米粘虫(Mythimna separata walker)表现出良好的致死活性, 2-(3-(2,6-二氟苯基)-1-甲基-1H-1,2,4-三唑-5-基)-3-(乙基磺酰基)-6-(吡咯烷-1-基)吡啶(9c), N-(仲丁基)-6-(3-(2,6-二氟苯基)-1-甲基- 1H-1,2,4-三唑-5-基)-5-(乙基磺酰基)吡啶-2-胺(9g), 6-(3-(2,6-二氟苯基)-1-甲基-1H-1,2,4-三唑-5-基)-5-(乙基磺酰基)-N-异丁基吡啶-2-胺(9h)在100 mg/L时, 致死率仍达到80%.

关键词: 乙砜基, 三氮唑, 吡啶, 合成, 杀虫活性

According to the principle of active substructure splicing, novel 3-ethyl sulfone pyridine substituted aryl triazole compounds were designed and synthesized using 3,6-dichloropyridine-2-carboxylic acid as primary material. All the compounds were characterized by 1H NMR, 13C NMR and HRMS spectra. The preliminary bioassay indicated that most title compounds exhibited relatively high insecticidal activity against Mythimna separata walker at 500 mg/L. Especially 2-(3-(2,6-difluorophenyl)-1-methyl-1H-1,2,4-triazol-5-yl)-3-(ethylsulfonyl)-6-(pyrrolidin-1-yl)pyridine (9c), N-(sec-butyl)-6- (3-(2,6-difluorophenyl)-1-methyl-1H-1,2,4-triazol-5-yl)-5-(ethylsulfonyl)pyridin-2-amine (9g), 6-(3-(2,6-difluorophenyl)-1- methyl-1H-1,2,4-triazol-5-yl)-5-(ethylsulfonyl)-N-isobutylpyridin-2-amine (9h) exhibited mortality 80% against M. separate at 100 mg/L.

Key words: ethylsulfone, triazole, pyridine, synthesis, insecticidal activity