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

doi:10.6023/cjoc201902027

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (7): 2053-2061.DOI: 10.6023/cjoc201902027 Previous Articles Next Articles

Notes

新型含1,2,4-三唑环结构的吡唑肟醚化合物的合成及其生物活性

王誉蓉^a, 郑丹丹^b, 王杨^b, 叶浩^b, 姚炜^b, 丁颖^b, 顾海鹰^a, 冯霞^b, 李玲^b, 戴红^b,c

a 南通大学公共卫生学院南通 226019;
b 南通大学化学化工学院南通 226019;
c 南通丰田化工有限公司南通 226005

收稿日期:2019-02-25 修回日期:2019-03-22 发布日期:2019-04-08
通讯作者: 顾海鹰, 戴红 E-mail:guhy99@21cn.com;daihong_2015@aliyun.com
基金资助:
国家自然科学基金（Nos.21874077，21475070，21372135）和南通市科技计划（No.MS12017022-4）资助项目.

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

Received:2019-02-25 Revised:2019-03-22 Published:2019-04-08
Contact: 10.6023/cjoc201902027 E-mail:guhy99@21cn.com;daihong_2015@aliyun.com
Supported by:
Project 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).

1. Synthesis and Bioactivities of Novel Pyrazole Oxime Ethers Containing 1,2,4-Triazole Moiety.PDF(1016KB)

Abstract

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.

Key words: 1,2,4-triazole, pyrazole oxime ether, synthesis, bioactivity

Cite this article

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]. Chin. J. Org. Chem., 2019, 39(7): 2053-2061.

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新型含1,2,4-三唑环结构的吡唑肟醚化合物的合成及其生物活性

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

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