Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (3): 861-866.DOI: 10.6023/cjoc201808033 Previous Articles     Next Articles

Notes

3-(((3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基)亚甲基)氨基)取代苯并[d][1,2,3]三嗪-4(3H)-酮类化合物的合成及生物活性

张燕, 朱洪伟, 尚俊峰, 王宝雷, 李正名   

  1. 南开大学化学学院 元素有机化学国家重点实验室 化学化工协同创新中心(天津) 天津 300071
  • 收稿日期:2018-08-28 修回日期:2018-10-22 出版日期:2019-03-25 发布日期:2018-11-12
  • 通讯作者: 王宝雷, 李正名 E-mail:nkwbl@nankai.edu.cn;nkzml@vip.163.com
  • 基金资助:

    天津市自然科学基金(No.17JCYBJC19900)、国家重点研发计划(No.2017YFD0200505)和国家自然科学基金(No.21772103)资助项目.

Synthesis and Biological Activities of Novel 3-(((3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl) methylene) amino)-substituted-benzo[d] [1,2,3]triazin-4(3H)-ones

Zhang Yan, Zhu Hongwei, Shang Junfeng, Wang Baolei, Li Zhengming   

  1. Collaborative Innovation Center of Chemical Science and Enginneering(Tianjin), State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071
  • Received:2018-08-28 Revised:2018-10-22 Online:2019-03-25 Published:2018-11-12
  • Contact: 10.6023/cjoc201808033 E-mail:nkwbl@nankai.edu.cn;nkzml@vip.163.com
  • Supported by:

    Project supported by the Natural Science Foundation of Tianjin City (No. 17JCYBJC19900), the National Key Research and Development Program of China (No. 2017YFD0200505), and the National Natural Science Foundation of China (No. 21772103).

A series of 3-(((3-bromo-1-(3-chloropyridin-2-yl) -1H-pyrazol-5-yl) methylene) amino) substituted-benzo[d] [1,2,3]-triazin-4(3H) -ones were synthesized successfully with ethyl N-pyridylpyrazole carboxylate and substituted aminobenzoic acids as starting materials, via multi-step reactions of reduction, oxidation, nucleophilic addition, condensation and diazotization. The preliminary bioassay tests indicated that most of these compounds have certain insecticidal activities, among which one compound showed a mortality rate of 70% towards Mythimna separata Walker at the test concentration of 200 mg·L-1, some compounds exhibited favorable fungicidal activities at 50 mg·L-1, particularly two compounds which possessed 92.3% growth inhibitory rate against Physalospora piricola, could be used as new fungicidal leading structures for further investigations on this type of compounds.

Key words: N-pyridylpyrazole derivatives, benzotriazinone, insecticidal activity, fungicidal activity, structure-activity relationship