有机化学 ›› 2019, Vol. 39 ›› Issue (5): 1489-1496.DOI: 10.6023/cjoc201810025 上一篇    下一篇

研究简报

新型N-取代苯基-2-吡唑基烟酰胺类化合物的合成及其生物活性

尚俊峰, 刘巧霞, 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:2018-10-19 修回日期:2018-12-03 出版日期:2019-05-25 发布日期:2019-01-18
  • 通讯作者: 王宝雷, 李正名 E-mail:nkwbl@nankai.edu.cn;nkzml@vip.163.com
  • 基金资助:

    国家重点研发计划(Nos.2017YFD0200505,2018YFD0200100)、国家自然科学基金(No.21772103)和天津市自然科学基金(No.17JCYBJC19900)资助项目.

Synthesis and Biological Activities of Novel N-Substitutedphenyl-2-pyrazolylnicotinamides

Shang Junfeng, Liu Qiaoxia, Wang Baolei, Li Zhengming   

  1. State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Enginneering(Tianjin), College of Chemistry, Nankai University, Tianjin 300071
  • Received:2018-10-19 Revised:2018-12-03 Online:2019-05-25 Published:2019-01-18
  • Contact: 10.6023/cjoc201810025 E-mail:nkwbl@nankai.edu.cn;nkzml@vip.163.com
  • Supported by:

    Project supported by the National Key Research and Development Program of China (Nos. 2017YFD0200505, 2018YFD0200100), the National Natural Science Foundation of China (No. 21772103) and the Natural Science Foundation of Tianjin City (No. 17JCYBJC19900).

基于含吡啶基吡唑的邻甲酰氨基苯甲酰胺类农药分子结构,采用“酰基移位”的策略,以2-氯-3-氰基吡啶和4-溴吡唑或3,5-二甲基吡唑为起始原料,简便合成了14个结构新颖的N-取代苯基-2-吡唑基烟酰胺类目标化合物.通过1H NMR、13C NMR和HRMS对新化合物进行了结构表征.初步生物活性测试结果表明,目标化合物在200 mg/L浓度下大多具有明显的杀虫活性,其中N-[4-氯-2-(乙氨基甲酰基)-6-甲基苯基]-2-(3,5-二甲基-1H-吡唑-1-基)烟酰胺(Il)对东方粘虫(Mythimna separata Walker)具有70%的致死率;部分化合物在50 mg/L浓度下对苹果轮纹病菌(Physalospora piricola)和番茄早疫病菌(Alternaria solani Sorauer)表现出较好的杀菌活性,其中2-(4-溴-1H-吡唑-1-基)-N-[2-(环丙氨基甲酰基)-4-碘-6-甲基苯基]烟酰胺(If)和2-(4-溴-1H-吡唑-1-基)-N-[4-氯-2-(乙氨基甲酰基)-6-甲基苯基]烟酰胺(Ih)对苹果轮纹病菌的抑制率分别达到62.9%和54.3%,2-(4-溴-1H-吡唑-1-基)-N-[4-氯-2-(正丙氨基甲酰基)苯基]烟酰胺(Id)对番茄早疫病菌具有54.5%的抑制率.研究结果为今后新型2-吡唑基烟酰胺类衍生物的深入研究提供了重要参考信息.

关键词: 2-吡唑基烟酰胺, 合成, 杀虫活性, 杀菌活性

Based on the agrochemical structure of anthranilic diamides, fourteen novel N-substitutedphenyl-2-pyrazolyl- nicotinamides were conveniently synthesized with 2-chloro-3-cyanopyridine and 4-bromopyrazole or 3,5-dimethylpyrazole as starting materials, via an "acyl transposing" design strategy. Their structures were characterized by 1H NMR, 13C NMR and HRMS. The preliminary bioassay tests indicated that most of these compounds exhibited obvious insecticidal activity at the test concentration of 200 mg/L, among which N-(4-chloro-2-(ethylcarbamoyl)-6-methylphenyl)-2-(3,5-dimethyl-1H-pyra- zol-1-yl)nicotinamide (Il) possessed a 70% mortality rate against Mythimna separata Walker; some of the compounds displayed favorable fungicidal activities at 50 mg/L towards Physalospora piricola and Alternaria solani Sorauer, especially 2-(4-bromo-1H-pyrazol-1-yl)-N-(2-(cyclopropylcarbamoyl)-4-iodo-6-methylphenyl)nicotinamide (If) and 2-(4-bromo-1H- pyrazol-1-yl)-N-(4-chloro-2-(ethylcarbamoyl)-6-methylphenyl)nicotinamide (Ih) against Physalospora piricola, and 2-(4- bromo-1H-pyrazol-1-yl)-N-(4-chloro-2-(propylcarbamoyl)phenyl)nicotinamide (Id) against Alternaria solani Sorauer had growth inhibitory rates of 62.9%, 54.3% and 54.5%, respectively. These research results provide important reference for the further study of novel 2-pyrazolylnicotinamide derivatives.

Key words: 2-pyrazolylnicotinamides, synthesis, insecticidal activity, fungicidal activity