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2020 , Vol. 40 >Issue 3: 774 - 781

DOI: https://doi.org/10.6023/cjoc201910013

研究简报

含取代噁唑结构的新型吡唑肟衍生物的合成与生物活性

  • 朱玥 ,
  • 郑丹丹 ,
  • 倪亚丹 ,
  • 李金峰 ,
  • 周环宇 ,
  • 胡兰萍 ,
  • 李玲 ,
  • 鞠剑峰 ,
  • 陈家正 ,
  • 李宏 ,
  • 石玉军 ,
  • 戴红
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  • a 南通大学化学化工学院 南通 226019;
    b 南通丰田化工有限公司 南通 226005

收稿日期: 2019-10-11

  修回日期: 2019-10-29

  网络出版日期: 2020-04-02

基金资助

国家自然科学基金（Nos.21372135，21802075）、江苏省自然科学基金（No.BK20160413）、南通市科技计划（Nos.MS12017022-4，JC2018118，MS12019060）资助项目.

收起

Synthesis and Biological Activities of Novel Pyrazole Oxime Derivatives Bearing an Oxazole Moiety

  • Zhu Yue ,
  • Zheng Dandan ,
  • Ni Yadan ,
  • Li Jinfeng ,
  • Zhou Huanyu ,
  • Hu Lanping ,
  • Li Ling ,
  • Ju Jianfeng ,
  • Chen Jiazheng ,
  • Li Hong ,
  • Shi Yujun ,
  • Dai Hong
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  • a College of Chemistry and Chemical Engineering, Nantong University, Nantong, Jiangsu 226019;
    b Nantong Fengtian Chemical Industry Co. Ltd, Nantong, Jiangsu 226005

Received date: 2019-10-11

  Revised date: 2019-10-29

  Online published: 2020-04-02

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21372135, 21802075), the Natural Science Foundation of Jiangsu Province (No. BK20160413), and the Science and Technology Project Fund of Nantong City (Nos. MS12017022-4, JC2018118, MS12019060).

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摘要

为了发现具有良好生物活性的吡唑肟化合物，以唑螨酯为先导化合物，在吡唑肟中引入取代噁唑结构，设计并制备了20个未见文献报道的新型吡唑肟衍生物，利用1H NMR，13C NMR和元素分析确证了目标产物的结构.生物活性测试结果显示，部分目标化合物在500和100 μg/mL浓度下对粘虫或蚜虫表现出优良的杀虫活性，其中5-（3-氟苯氧基）-1，3-二甲基-1H-吡唑-4-甲酰基-O-{[5-（4-氯苯基）噁唑-2-基]甲基}肟（9j）、5-（4-氟苯氧基）-1，3-二甲基-1H-吡唑-4-甲酰基-O-{[5-（4-氯苯基）噁唑-2-基]甲基}肟（9k）、5-（4-叔丁基苯氧基）-1，3-二甲基-1H-吡唑-4-甲酰基-O-{[5-（4-氯苯基）噁唑-2-基]甲基}肟（9r）和5-（4-甲氧基苯氧基）-1，3-二甲基-1H-吡唑-4-甲酰基-O-{[5-（4-氯苯基）噁唑-2-基]甲基}肟（9s）在浓度为100 μg/mL时对粘虫的防治效果均达100%，5-（4-溴苯氧基）-1，3-二甲基-1H-吡唑-4-甲酰基-O-{[5-（4-氟苯基）噁唑-2-基]甲基}肟（9g）和9s在浓度为100 μg/mL时对蚜虫的杀灭活性均为100%.此外，化合物9s在500 μg/mL时对朱砂叶螨的防治效果为70%.

关键词： 噁唑; 吡唑肟; 合成; 生物活性

本文引用格式

朱玥 , 郑丹丹 , 倪亚丹 , 李金峰 , 周环宇 , 胡兰萍 , 李玲 , 鞠剑峰 , 陈家正 , 李宏 , 石玉军 , 戴红 . 含取代噁唑结构的新型吡唑肟衍生物的合成与生物活性[J]. 有机化学, 2020 , 40(3) : 774 -781 . DOI: 10.6023/cjoc201910013

Abstract

In search of novel pyrazole oximes with good biological activities, twenty pyrazole oxime compounds were prepared by introducing an oxazole unit into pyrazole oxime based on the structure of fenpyroximate. The structures of the target compounds were confirmed by 1H NMR, 13C NMR and elemental analysis. Preliminary bioassay displayed that some target compounds had wonderful insecticidal activities against Oriental armyworm or Aphis medicaginis at the concentrations of 500 and 100 μg/mL. At the concentration of 100 μg/mL, 5-(3-fluorophenoxy)-1,3-dimethyl-1H-pyrazole-4-formyl-O-((5-(4-chlo-rophenyl)oxazol-2-yl)methyl)oxime (9j), 5-(4-fluorophenoxy)-1,3-dimethyl-1H-pyrazole-4-formyl-O-((5-(4-chlorophenyl)-oxazol-2-yl)methyl)oxime (9k), 5-(4-t-butylphenoxy)-1,3-dimethyl-1H-pyrazole-4-formyl-O-((5-(4-chlorophenyl)oxazol-2-yl)methyl)oxime (9r) and 5-(4-methoxyphenoxy)-1,3-dimethyl-1H-pyrazole-4-formyl-O-((5-(4-chlorophenyl)oxazol-2-yl)me-thyl)oxime (9s) showed 100% mortality rate against Oriental armyworm, and 5-(4-bromophenoxy)-1,3-dimethyl-1H-pyra-zole-4-formyl-O-((5-(4-fluorophenyl)oxazol-2-yl)methyl)oxime (9g) and 9s exhibited 100% insecticidal property against Aphis medicaginis. Additionally, compound 9s possessed 70% insecticidal activity against Tetranychus cinnabarinus at 500 μg/mL.

Key words： oxazole; pyrazole oxime; synthesis; biological activity

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