高等学校化学学报 ›› 2020, Vol. 41 ›› Issue (5): 1026-1034.doi: 10.7503/cjcu20190582

• 有机化学 • 上一篇    下一篇

1-(4-氯苯基)-2-环丙基酮肟醚的设计、 合成及杀虫活性

李康明1,陈佳1,易阳杰1,闫忠忠1,叶姣1,龙楚云2,柳爱平2,胡艾希1,*(),李建明2,*()   

  1. 1. 湖南大学化学化工学院, 长沙 410082
    2. 湖南化工研究院有限公司, 国家农药创制工程技术研究中心, 长沙 410007
  • 收稿日期:2019-11-11 出版日期:2020-05-10 发布日期:2020-01-17
  • 通讯作者: 胡艾希,李建明 E-mail:axhu@hnu.edu.cn;msouonn@126.com
  • 基金资助:
    国家自然科学基金(21572050)

Design, Synthesis and Insecticidal Activity of 1-(4-Chlorophenyl)-2-cyclopropylpropan-1-one Oxime Ether

LI Kangming1,CHEN Jia1,YI Yangjie1,YAN Zhongzhong1,YE Jiao1,LONG Chuyun2,LIU Aiping2,HU Aixi1,*(),LI Jianming2,*()   

  1. 1. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China
    2. National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007, China
  • Received:2019-11-11 Online:2020-05-10 Published:2020-01-17
  • Contact: Aixi HU,Jianming LI E-mail:axhu@hnu.edu.cn;msouonn@126.com
  • Supported by:
    † Supported by the National Natural Science Foundation of China(21572050)

摘要:

采用中间体衍生化方法, 以环唑醇中间体1-(4-氯苯基)-2-环丙基丙酮作为基本骨架, 引入肟醚活性片段, 合成了32个新的1-(4-氯苯基)-2-环丙基酮肟醚类化合物, 其化学结构经核磁共振波谱和质谱等确认. 单晶X衍射分析表明, 化合物2n属于单斜晶系, 空间群为P21/c. 生物活性筛选结果表明, 化合物1i在200 mg/L浓度下对蚜虫的致死率为78.57%; 化合物1g在200 mg/L浓度下对红蜘蛛的致死率为69.95%; 化合物1i在200和12.5 mg/L浓度下对黏虫的致死率分别为100%和85%.

关键词: 1-(4-氯苯基)-2-环丙基酮肟醚, 合成, 单晶, 杀虫活性

Abstract:

Based on the intermediate derivatization method, the active fragment of oxime ether was introduced into 1-(4-chlorophenyl)-2-cyclopropylpropan-1-one as a basic skeleton, and 32 novel compounds were designed and synthesized with the fragment of 1-(4-chlorophenyl)-2-cyclopropylpropan-1-one. Their chemical structures were confirmed by nuclear magnetic resonance spectroscopy and mass spectrometry. Single crystal X-ray diffraction of compound 2n was carried out. The result showed that compound 2n belonged to the monoclinic system and space group of 2n was P21/c. The initial screening activity showed that the mortality rate of compound 1i and 1g against aphids and red spiders were 78.57% and 69.95% at the concentration of 200 mg/L, respectiviely, while the mortality rate of compound 1i were 100% and 85% against aphids at the concentration of 200 and 12.5 mg/L, respectiviely. The results showed that compound 1i had the value of further development.

Key words: 1-(4-Chlorophenyl)-2-cyclopropylpropan-1-oneoxime ether, Synthesis, Single crystal, Insecticidal activity

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