Citation: 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]. Chinese Journal of Organic Chemistry, ;2018, 38(12): 3318-3325. doi: 10.6023/cjoc201807048 shu

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

Corresponding author: Shen Aibao, wjmnt@ntu.edu.cn Dai Hong, daihong_2015@aliyun.com
Received Date: 26 July 2018
Revised Date: 29 August 2018
Available Online: 5 December 2018
Fund Project: 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)the Science and Technology Innovation Foundation for the College Students of Jiangsu Province 201810304016Zthe National Natural Science Foundation of China 21372135the Science and Technology Project Fund of Nantong City MS22015020the Research Foundation of the Six People Peak of Jiangsu Province 2013-SWYY-013

Figures(3)

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%.
- oxazole,
- pyrazole oxime ether,
- synthesis,
- insecticidal activity
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