有机化学 ›› 2019, Vol. 39 ›› Issue (3): 861-866.DOI: 10.6023/cjoc201808033 上一篇    下一篇

研究简报

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).

N-吡啶基吡唑甲酸乙酯、取代邻氨基苯甲酸为原料,经由还原、氧化、亲核加成、缩合、重氮化等多步反应,合成了一系列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)-酮类目标化合物.初步生物活性测试结果表明,该系列化合物大多具有一定的杀虫活性,其中一个化合物在200 mg·L-1浓度下对东方粘虫(Mythimna separata Walker)具有70%的致死率;部分化合物表现出显著的抑菌活性,有两个化合物在50 mg·L-1浓度下对苹果轮纹病菌(Physalospora piricola)具有92.3%的抑制率,可作为新型抑菌先导结构,为后续的深入研究提供重要参考.

关键词: N-吡啶基吡唑衍生物, 苯并三嗪酮, 杀虫活性, 抑菌活性, 构效关系

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