高等学校化学学报 ›› 2020, Vol. 41 ›› Issue (4): 716-725.doi: 10.7503/cjcu20190504

• 有机化学 • 上一篇    下一篇

5-吡唑甲酰胺类衍生物的设计、 合成与生物活性

李康明1,李延赛1,易阳杰1,徐雷涛1,叶姣1,欧晓明2,李建明2,胡艾希1,*()   

  1. 1. 湖南大学化学化工学院, 长沙 410082
    2. 湖南化工研究院, 长沙 410007
  • 收稿日期:2019-09-27 出版日期:2020-04-10 发布日期:2020-02-07
  • 通讯作者: 胡艾希 E-mail:axhu@hnu.edu.cn
  • 基金资助:
    国家重点研发计划项目(2016YFD0300708)

Design, Synthesis and Biological Activity of 5-Pyrazole Carboxamides

LI Kangming1,LI Yansai1,YI Yangjie1,XU Leitao1,YE Jiao1,OU Xiaoming2,LI Jianming2,HU Aixi1,*()   

  1. 1. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China
    2. Hunan Research Institute of Chemical Industry, Changsha 410007, China
  • Received:2019-09-27 Online:2020-04-10 Published:2020-02-07
  • Contact: Aixi HU E-mail:axhu@hnu.edu.cn
  • Supported by:
    † Supported by the National Key Research & Development Program of China(2016YFD0300708)

摘要:

以2种5-吡唑甲酸为原料, 分别与噻唑胺和苯并呋喃胺发生缩合反应, 制备了23个新的5-吡唑甲酰胺类化合物; 采用核磁共振波谱和质谱等对目标化合物结构进行了表征; 对化合物B1和B3进行了量子化学计算、 前沿分子轨道及分子范德华表面静电势分析. 生物活性实验结果表明, 在500 mg/L浓度下部分化合物对黏虫和蚜虫有良好的杀虫活性, 其中化合物A1和B1对黏虫的致死率均为100%, 化合物B3, B4和C9对蚜虫的致死率分别为100%, 100%和95.54%; 在25 mg/L浓度下化合物A3对烟草赤星病菌的抑制率、 化合物C7对小麦赤霉病菌的抑制率以及化合物A1和A4对油菜菌核病菌的抑制率均大于50%.

关键词: 5-吡唑甲酰胺, 杀菌活性, 杀虫活性, 量子化学计算

Abstract:

Twenty-three novel 5-pyrazole carboxamides were prepared by condensing two kinds of 5-pyrazolecarboxylic acids with thiazolamides and benzofuranamines. The chemical structures were confirmed by nuclear magnetic resonance(NMR) and mass spectrometry, etc. Quantum chemical calculations, frontier molecular orbitals and molecular van der Waals surface electrostatic potentials were analyzed for compounds B1 and B3. Biological activity screening test results showed that some compounds had excellent Insecticidal activity against Armyworm and Aphis fabae at 500 mg/L concentration, and the lethal rate of compound A1 and B1 against Armyworm was 100%, while compound B3, B4 and C9 showed excellent inhibitory activity towards Aphis fabae with the inhibition rate of 100%, 100% and 95.54%, correspondingly. At a concentration of 25 mg/L, the growth inhibition rates of compound A3 against Alternaria alternata, compound C7 against Gibberella zeae, compounds A1 and A4 against Sclerotonia sclerotiorum were over 50%.

Key words: 5-Pyrazolecarboxamide, Bactericidal activity, Insecticidal activity, Quantum chemical calculation

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