Synthesis and Insecticidal Activities of Novel Pyrazole Oxime Ethers Containing an Oxazole Moiety

doi:10.6023/cjoc201807048

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (12): 3318-3325.DOI: 10.6023/cjoc201807048 Previous Articles Next Articles

Notes

新型含噁唑环结构的吡唑肟醚类化合物的合成与杀虫活性研究

周钱^a, 郑丹丹^a, 石玉军^a, 姚炜^a, 钱宏炜^a, 丁颖^a, 魏中昊^a, 沈爱宝^a, 冯霞^a, 石健^b, 戴红^a

a 南通大学化学化工学院南通 226019;
b 南通大学分析测试中心南通 226019

收稿日期:2018-07-26 修回日期:2018-08-29 发布日期:2018-09-05
通讯作者: 沈爱宝, 戴红 E-mail:wjmnt@ntu.edu.cn;daihong_2015@aliyun.com
基金资助:
国家自然科学基金（No.21372135）、江苏省"六大人才高峰"（No.2013-SWYY-013）、南通市科技计划（No.MS22015020）和江苏省大学生创新训练计划（No.201810304016Z）资助项目

Synthesis and Insecticidal Activities of Novel Pyrazole Oxime Ethers Containing an Oxazole Moiety

Zhou Qian^a, Zheng Dandan^a, Shi Yujun^a, Yao Wei^a, Qian Hongwei^a, Ding Ying^a, Wei Zhonghao^a, Shen Aibao^a, Feng Xia^a, Shi Jian^b, Dai Hong^a

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

Received:2018-07-26 Revised:2018-08-29 Published:2018-09-05
Contact: 10.6023/cjoc201807048 E-mail:wjmnt@ntu.edu.cn;daihong_2015@aliyun.com
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21372135), the Research Foundation of the Six People Peak of Jiangsu Province (No. 2013-SWYY-013), and the Science and Technology Project Fund of Nantong City (No. MS22015020) and the Science and Technology Innovation Foundation for the College Students of Jiangsu Province (No. 201810304016Z).

1. Synthesis and Insecticidal Activities of Novel Pyrazole Oxime Ethers Containing an Oxazole Moiety.PDF(863KB)

Abstract

In order to find new pyrazole oxime ether derivatives with potent bioactivities, fifteen novel pyrazole oxime ethers containing an oxazole moiety were designed and prepared according to the method of active substructure combination. Their structures were confirmed through ¹H NMR, ¹³C NMR, and elemental analysis. Preliminary bioassay showed that most of the title compounds displayed wonderful insecticidal activities against Oriental armyworm, Aphis medicaginis and Tetranychus cinnabarinus. At the concentration of 500 μg/mL, ten compounds exhibited acaricidal activity against Tetranychus cinnabarinus with over 80%, especially four compounds indicated comparable insecticidal activity against Tetranychus cinnabarinus to that of the control of fenpyroximate, the lethal rates of nine compounds against Aphis medicaginis were all 100%, which were near to that of imidacloprid, and the lethal rates of fourteen compounds against Oriental armyworm were all 100%, which were similar to that of pyridalyl. At the concentration of 100 μg/mL, the lethal rates of three compounds against Tetranychus cinnabarinus were all 60%, and the lethal rates of two compounds against Aphis medicaginis were 90% and 100%. When the concentration was reduced to 20 μg/mL, compound 1,3-dimethyl-5-(4-methylphenoxy)-1H-pyrazole-4-carbaldehyde-O-[4-(oxazol-5-yl)phenylmethyl]oxime (7i) still had insecticidal activity against Aphis medicaginis with 60%.

Key words: oxazole, pyrazole oxime ether, synthesis, insecticidal activity

Cite this article

Zhou Qian, Zheng Dandan, Shi Yujun, Yao Wei, Qian Hongwei, Ding Ying, Wei Zhonghao, Shen Aibao, Feng Xia, Shi Jian, Dai Hong. Synthesis and Insecticidal Activities of Novel Pyrazole Oxime Ethers Containing an Oxazole Moiety[J]. Chin. J. Org. Chem., 2018, 38(12): 3318-3325.

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新型含噁唑环结构的吡唑肟醚类化合物的合成与杀虫活性研究

Synthesis and Insecticidal Activities of Novel Pyrazole Oxime Ethers Containing an Oxazole Moiety

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