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

doi:10.6023/cjoc201910013

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (3): 774-781.DOI: 10.6023/cjoc201910013 Previous Articles Next Articles

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^a, 郑丹丹^a, 倪亚丹^a, 李金峰^a, 周环宇^a, 胡兰萍^a, 李玲^a, 鞠剑峰^a, 陈家正^a, 李宏^b, 石玉军^a, 戴红^a,b

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 发布日期:2020-04-02
通讯作者: 胡兰萍, 鞠剑峰, 戴红 E-mail:hlp@ntu.edu.cn;ju.jf@ntu.edu.cn;daihong_2015@aliyun.com
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.

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

Zhu Yue^a, Zheng Dandan^a, Ni Yadan^a, Li Jinfeng^a, Zhou Huanyu^a, Hu Lanping^a, Li Ling^a, Ju Jianfeng^a, Chen Jiazheng^a, Li Hong^b, Shi Yujun^a, Dai Hong^a,b

a College of Chemistry and Chemical Engineering, Nantong University, Nantong, Jiangsu 226019;
b Nantong Fengtian Chemical Industry Co. Ltd, Nantong, Jiangsu 226005

Received:2019-10-11 Revised:2019-10-29 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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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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Zhu Yue, Zheng Dandan, Ni Yadan, Li Jinfeng, Zhou Huanyu, Hu Lanping, Li Ling, Ju Jianfeng, Chen Jiazheng, Li Hong, Shi Yujun, Dai Hong. Synthesis and Biological Activities of Novel Pyrazole Oxime Derivatives Bearing an Oxazole Moiety[J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 774-781.

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含取代噁唑结构的新型吡唑肟衍生物的合成与生物活性

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

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