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

doi:10.6023/cjoc202002024

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (6): 1638-1646.DOI: 10.6023/cjoc202002024 Previous Articles Next Articles

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^a, 倪亚丹^a, 李金峰^a, 丁颖^a, 张敏^a, 王杨^a, 胡兰萍^a, 周环宇^a, 杨冰^a, 石健^b, 高磊^a, 戴红^a

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 发布日期:2020-03-11
通讯作者: 胡兰萍, 杨冰, 戴红 E-mail:hlp@ntu.edu.cn;yangbing111@ntu.edu.cn;daihong_2015@aliyun.com
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.

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

Xun Xiao^a, Ni Yadan^a, Li Jinfeng^a, Ding Ying^a, Zhang Min^a, Wang Yang^a, Hu Lanping^a, Zhou Huanyu^a, Yang Bing^a, Shi Jian^b, Gao Lei^a, Dai Hong^a

a College of Chemistry and Chemical Engineering, Nantong University, Nantong, Jiangsu 226019;
b Analysis and Testing Center, Nantong University, Nantong, Jiangsu 226019

Received:2020-02-18 Revised:2020-03-06 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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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

Cite this article

Xun Xiao, Ni Yadan, Li Jinfeng, Ding Ying, Zhang Min, Wang Yang, Hu Lanping, Zhou Huanyu, Yang Bing, Shi Jian, Gao Lei, Dai Hong. Synthesis and Bioactivities of Novel Pyrazole Oxime Derivatives Containing a N-Pyridylpyrazole Moiety[J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1638-1646.

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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

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

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