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2020 , Vol. 40 >Issue 6: 1638 - 1646

DOI: https://doi.org/10.6023/cjoc202002024

研究论文

新型含N-吡啶基吡唑结构的吡唑肟类衍生物的合成与生物活性

  • 荀校 ,
  • 倪亚丹 ,
  • 李金峰 ,
  • 丁颖 ,
  • 张敏 ,
  • 王杨 ,
  • 胡兰萍 ,
  • 周环宇 ,
  • 杨冰 ,
  • 石健 ,
  • 高磊 ,
  • 戴红
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  • a 南通大学化学化工学院 江苏南通 226019;
    b 南通大学分析测试中心 江苏南通 226019

收稿日期: 2020-02-18

  修回日期: 2020-03-06

  网络出版日期: 2020-03-11

基金资助

国家自然科学基金（No.21372135）和南通市科技计划（No.MS12019060）资助项目.

收起

Synthesis and Bioactivities of Novel Pyrazole Oxime Derivatives Containing a N-Pyridylpyrazole Moiety

  • Xun Xiao ,
  • Ni Yadan ,
  • Li Jinfeng ,
  • Ding Ying ,
  • Zhang Min ,
  • Wang Yang ,
  • Hu Lanping ,
  • Zhou Huanyu ,
  • Yang Bing ,
  • Shi Jian ,
  • Gao Lei ,
  • Dai Hong
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  • a College of Chemistry and Chemical Engineering, Nantong University, Nantong, Jiangsu 226019;
    b Analysis and Testing Center, Nantong University, Nantong, Jiangsu 226019

Received date: 2020-02-18

  Revised date: 2020-03-06

  Online published: 2020-03-11

Supported by

Project supported by the National Natural Science Foundation of China (No. 21372135) and the Science and Technology Project Fund of Nantong City (No. MS12019060).

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摘要

为了探索与发现具有优良生物活性的吡唑肟类衍生物，利用活性基团拼接法，以杀螨剂唑螨酯为先导化合物，引入N-吡啶基吡唑结构单元，设计合成了20个未见文献报道的新型吡唑肟类化合物，化合物结构均经1H NMR，13C NMR和元素分析确认.生物活性初步测试结果表明，所有目标化合物在500 μg/mL浓度下对东方粘虫均呈现出100%的杀虫活性.5个化合物在100 μg/mL下对东方粘虫的杀灭活性均达100%，2个化合物在20 μg/mL下对东方粘虫仍具有40%的杀虫效果.此外，3个化合物在500 μg/mL浓度下对苜蓿蚜的致死率为40%~60%.值得注意的是，5-（2-溴苯氧基）-1，3-二甲基-1H-吡唑-4-甲醛-O-{1-（3-氯吡啶-2-基）-3-[（6-氯吡啶-3-基）甲氧基]-1H-吡唑-5-甲酰基}肟（10b）和5-（4-叔丁基苯氧基）-1，3-二甲基-1H-吡唑-4-甲醛-O-{1-（3-氯吡啶-2-基）-3-[（6-氯吡啶-3-基）甲氧基]-1H-吡唑-5-甲酰基}肟（10k）对东方粘虫的杀虫活性较为突出，可作深入的结构优化与杀虫活性探究.

关键词： N-吡啶基吡唑; 吡唑肟; 合成; 生物活性

本文引用格式

荀校 , 倪亚丹 , 李金峰 , 丁颖 , 张敏 , 王杨 , 胡兰萍 , 周环宇 , 杨冰 , 石健 , 高磊 , 戴红 . 新型含N-吡啶基吡唑结构的吡唑肟类衍生物的合成与生物活性[J]. 有机化学, 2020 , 40(6) : 1638 -1646 . DOI: 10.6023/cjoc202002024

Abstract

In search of novel pyrazole oxime compounds with potent bioactivities, twenty pyrazole oxime derivatives were synthesized by introducing N-pyridylpyrazole unit into pyrazole oxime skeleton, based on the lead of fenpyroximate. The title compounds were structurually characterized by 1H NMR, 13C NMR and elemental analysis. The preliminary bioassay showed that all the title compounds had 100% insecticidal activities against Mythimna separata Walker at 500 μg/mL. Five compounds displayed 100% mortality rate towards Mythimna separata Walker at 100 μg/mL. Two compounds both exhibited 40% mortality rate against Mythimna separata Walker at 20 μg/mL. In addition, three compounds had 40~60% insecticidal activities to Aphis medicaginis at 500 μg/mL. It is worthy of noting that 5-(2-bromophenoxy)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde-O-{1-(3-chloropyridin-2-yl)-3-[(6-chloropyridin-3-yl)methoxy]-1H-pyrazole-5-formyl}oxime (10b) and 5-(4-t-butylphen-oxy)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde-O-{1-(3-chloropyridin-2-yl)-3-[(6-chloropyridin-3-yl)methoxy]-1H-pyrazole-5-formyl}oxime (10k) which have potent insecticidal activities against Mythimna separata Walker, can be utilized in insecticide research with further optimization.

Key words： N-pyridylpyrazole; pyrazole oxime; synthesis; bioactivity

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