Citation: Wang Yurong, Zheng Dandan, Wang Yang, Ye Hao, Yao Wei, Ding Ying, Gu Haiying, Feng Xia, Li Ling, Dai Hong. Synthesis and Bioactivities of Novel Pyrazole Oxime Ethers Containing 1, 2, 4-Triazole Moiety[J]. Chinese Journal of Organic Chemistry, ;2019, 39(7): 2053-2061. doi: 10.6023/cjoc201902027 shu

Synthesis and Bioactivities of Novel Pyrazole Oxime Ethers Containing 1, 2, 4-Triazole Moiety

Wang Yurong ^a,† ,
Zheng Dandan ^b,† ,
Wang Yang ^b ,
Ye Hao ^b ,
Yao Wei ^b ,
Ding Ying ^b ,
Gu Haiying ^a,, ,
Feng Xia ^b ,
Li Ling ^b ,
Dai Hong ^b,c,,

a.
School of Public Health, Nantong University, Nantong 226019
b.
College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019
c.
Nantong Fengtian Chemical Industry Co. Ltd, Nantong 226005

Corresponding author: Gu Haiying, guhy99@21cn.com Dai Hong, daihong_2015@aliyun.com

^†

Received Date: 25 February 2019
Revised Date: 22 March 2019
Available Online: 2 July 2019
Fund Project: the National Natural Science Foundation of China 21475070the National Natural Science Foundation of China 21372135Project supported by the National Natural Science Foundation of China (Nos. 21874077, 21475070, 21372135), and the Science and Technology Project Fund of Nantong City (No. MS12017022-4)the Science and Technology Project Fund of Nantong City MS12017022-4the National Natural Science Foundation of China 21874077

Figures(3)

Eighteen novel pyrazole oxime ethers containing 1, 2, 4-triazole moiety were designed and synthesized according to the method of active substructure combination. Their structures were characterized by ¹H NMR, ¹³C NMR, and elemental analyses. Preliminary bioassay showed that some target compounds showed good insecticidal activities against Oriental armyworm, Aphis medicaginis and Tetranychus cinnabarinus. At the concentration of 500 μg/mL, target compounds had insecticidal activity against Oriental armyworm with 90%~100%, which were similar to the control of avermectin, four compounds showed 100% insecticidal activity against Aphis medicaginis, which were similar to imidacloprid. The lethal rate of 1- methyl-3-methyl-5-(3, 5-difluorophenoxy)-1H-pyrazole-4-carbaldehyde-O-[4-(1H-1, 2, 4-triazol-1-yl)phenylmethyl]oxime (8p) against Tetranychus cinnabarinus was 100%, which was similar to that of fenpyroximate. When the concentration was reduced to 100 μg/mL, six compounds exhibited insecticidal activity against Oriental armyworm with 90%~100%, three compounds showed insecticidal activity against Aphis medicaginis with 80%~100%, and compound 8p had acaricidal activity against Tetranychus cinnabarinus with 80%. At the concentration of 20 μg/mL, the lethal rates of two compounds against Oriental armyworm were 75% and 70%, respectively. Additionally, some compounds exhibited certain anti-tumor activity against human hepatocellular carcinoma SMMC-7721 cells.
- 1, 2, 4-triazole,
- pyrazole oxime ether,
- synthesis,
- bioactivity
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