Synthesis and Insecticidal Activities of Novel Pyrazole Oxime Ethers Carrying 1,3,4-Oxadiazole Unit

doi:10.6023/cjoc201908006

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (1): 232-238.DOI: 10.6023/cjoc201908006 Previous Articles Next Articles

含1,3,4-噁二唑结构的新型吡唑肟醚类衍生物的合成及杀虫活性

王杨^a, 叶浩^a, 钱程^a, 姚炜^a, 李宏^b, 王凯^a, 胡兰萍^a, 李玲^a, 吴锦明^a, 戴红^a

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:2019-08-04 修回日期:2019-08-26 发布日期:2019-09-05
通讯作者: 胡兰萍, 戴红 E-mail:hlp@ntu.edu.cn;daihong_2015@aliyun.com
基金资助:
国家自然科学基金（No.21372135）、南通市科技计划（No.MS12017022-4，MS12019060）和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 Carrying 1,3,4-Oxadiazole Unit

Wang Yang^a, Ye Hao^a, Qian Cheng^a, Yao Wei^a, Li Hong^b, Wang Kai^a, Hu Lanping^a, Li Ling^a, Wu Jinming^a, Dai Hong^a

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

Received:2019-08-04 Revised:2019-08-26 Published:2019-09-05
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21372135), the Science and Technology Project Fund of Nantong City (No. MS12017022-4, MS12019060), and the Science and Technology Innovation Foundation for the College Students of Jiangsu Province (No. 201810304016Z).

1. 200232S.pdf.pdf(872KB)

Abstract

In search of novel pyrazole oxime ether derivatives with potent bioactivities, fifteen new pyrazole oxime ethers were designed and synthesized by introducing 1,3,4-oxadiazole moiety into the C-4 position of pyrazole based on the structure of fenpyroximate. Their structures were confirmed by ¹H NMR, ¹³C NMR and elemental analysis. Preliminary bioassay data showed that some title compounds possessed good insecticidal activities against Oriental armyworm or Aphis medicaginis at the concentration of 500 and 100 μg/mL. At 100 μg/mL, compounds 10a, 10e, 10f and 10j displayed 100% mortality rate against Oriental armyworm, and compounds 10g, 10j and 10l showed insecticidal activity against Aphis medicaginis with 100%. In addition, compound 10l had 100% mortality rate against Tetranychus cinnabarinus at 500 μg/mL.

Key words: 1,3,4-oxadiazole, pyrazole oxime ether, synthesis, insecticidal activity

Cite this article

Wang Yang, Ye Hao, Qian Cheng, Yao Wei, Li Hong, Wang Kai, Hu Lanping, Li Ling, Wu Jinming, Dai Hong. Synthesis and Insecticidal Activities of Novel Pyrazole Oxime Ethers Carrying 1,3,4-Oxadiazole Unit[J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 232-238.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Li, Y.; Zhang, H. Q.; Liu, J.; Yang, X. P.; Liu, Z. J. J. Agric. Food Chem. 2006, 54, 3636.
[2] Dai, H.; Li, H.; Jin. Z. C.; Liu, W. Y.; Xiao, Y.; He, H. B.; Wang, Q. M.; Shi, Y. J. Chin. J. Org. Chem. 2016, 36, 185(in Chinese). (戴红, 李宏, 金智超, 刘文永, 肖瑶, 何海兵, 汪清民, 石玉军, 有机化学, 2016, 36, 185.)
[3] Liu, X. H.; Zhao, W.; Shen, Z. H.; Xing, J. H.; Yuan, J.; Yang, G.; Xu, T. M.; Peng, W. L. Bioorg. Med. Chem. Lett. 2016, 26, 3626.
[4] Zhai, Z. W.; Wang, Q.; Shen, Z. H.; Tan, C. X.; Weng, J. Q.; Liu, X. H. Chin. J. Org. Chem. 2017, 37, 232(in Chinese). (翟志文, 汪乔, 沈钟华, 谭成侠, 翁建全, 刘幸海, 有机化学, 2017, 37, 232.)
[5] Liu, X. H.; Zhao, W.; Shen, Z. H.; Xing, J. H.; Xu, T. M.; Peng, W. L. Eur. J. Med. Chem. 2017, 125, 881.
[6] Huang, Q. C.; Qian, X. H.; Song, G. H.; Cao, S. Pest Manage. Sci. 2003, 59, 933.
[7] Wang, B. L.; Li, Z. M.; Li, Y. H.; Wang, S. H. Chem. J. Chin. Univ. 2008, 29, 90(in Chinese). (王宝雷, 李正名, 李永红, 王素华, 高等学校化学学报, 2008, 29, 90.)
[8] Ruan, L. L.; Fan, R. J.; Liu, X. H.; Chen, J.; Weng, J. Q. Chin. J. Org. Chem. 2015, 35, 1166(in Chinese). (阮铃莉, 范人杰, 刘幸海, 陈杰, 翁建全, 有机化学, 2015, 35, 1166.)
[9] Formagio, A. S. N.; Tonin, L. T. D.; Foglio, M. A.; Madjarof, C.; Carvalho. J. E. D.; Costa, W. F. D.; Cardoso, F. P.; Sarragiotto, M. H. Bioorg. Med. Chem. 2008, 16, 9660.
[10] Shi, Y. J.; Ye, L. Y.; Zhong, S. L.; Cao, X. F.; Dai, H.; Hong, Y.; Li, C. J.; Shi, J.; Wu, J. M. Chin. J. Org. Chem. 2017, 37, 1844(in Chinese). (石玉军, 叶林玉, 仲苏林, 曹雄飞, 戴红, 洪宇, 李春建, 石健, 吴锦明, 有机化学, 2017, 37, 1844.)
[11] Zheng, X. M.; Zhong, L.; Wang, Y. L.; Chen, W. D.; Huang, Q. C.; Liu, C. X.; Song, G. H. J. Fluorine Chem. 2003, 123, 163.
[12] Shi, Y. J.; Li, Y.; Fang, Y.; Chen, J.; Ye, L. Y.; Ge, S. S.; Dai, H. Chin. J. Org. Chem. 2016, 36, 2472(in Chinese). (石玉军, 李阳, 方源, 陈佳, 叶林玉, 葛书山, 戴红, 有机化学, 2016, 36, 2472.)
[13] Li, Y.; Zhang, H. Q.; Liu, J.; Yang, X. P.; Liu, Z. J. J. Agric. Food Chem. 2006, 54, 3636.
[14] Ouyang, G. P.; Cai, X. J.; Chen, Z.; Song, B. A.; Bhadury, P. S.; Yang, S.; Jin, L. H.; Xue, W.; Hu, D. Y.; Zeng, S. J. Agric. Food Chem. 2008, 56, 10160.
[15] Dai, H.; Ge, S. S.; Guo, J.; Chen, S.; Huang, M. L.; Yang. J. Y.; Sun, S. Y.; Ling, Y.; Shi, Y. J. Eur. J. Med. Chem. 2018, 143, 1066.
[16] Hamaguchi, H.; Kajihara, O.; Katoh, M. J. Pestic. Sci. 1995, 20, 173.
[17] Fu, C. R.; Peng, J.; Ning, Y.; Liu, M.; Shan, P. C.; Liu, J.; Li, Y. Q.; Hu, F. Z.; Zhu, Y. Q.; Yang, H. Z.; Zou, X. M. Pest. Manage. Sci. 2014, 70, 1207.
[18] Wang, S. L.; Shi, Y. J.; He, H. B.; Li, Y.; Li, Y.; Dai, H. Chin. Chem. Lett. 2015, 26, 672.
[19] Dai, H.; Yao, W.; Sun, S. Y.; Li, L.; Shi, L.; Qian, H. W.; Li, C. J.; Shi, J.; Shi, Y. J. Chin. J. Org. Chem. 2017, 37, 3155(in Chinese). (戴红, 姚炜, 孙思宇, 李玲, 施磊, 钱宏炜, 李春建, 石健, 石玉军, 有机化学, 2017, 37, 3155.)
[20] Dai, H.; Ge, S. S.; Li, G.; Chen, J.; Shi, Y. J.; Ye, L. Y.; Ling, Y. Bioorg. Med. Chem. Lett. 2016, 26, 4504.
[21] Dai, H.; Ye, L. Y.; Li, Y.; Fang, Y.; Shi, Y. J.; Liang, Z. P.; Shi, J. Chin. J. Org. Chem. 2017, 37, 1020(in Chinese). (戴红, 叶林玉, 李阳, 方源, 石玉军, 梁志鹏, 石健, 有机化学, 2017, 37, 1020.)
[22] Dai, H.; Yao, W.; Du, X. C.; Wang, X. L.; Wu, J. M.; Chen, Q. W.; Li, C. J.; Shi, J.; Zhang, H. J. Chin. J. Org. Chem. 2017, 37, 3267(in Chinese). (戴红, 姚炜, 杜显超, 王祥龙, 吴锦明, 陈庆文, 李春建, 石健, 张海军, 有机化学, 2017, 37, 3267.)
[23] Zhou, Q.; Zheng, D. D.; Shi, Y. J.; Yao, W.; Qian, H. W.; Ding, Y.; Wei, Z. H.; Shen, A. B.; Feng, X.; Shi, J.; Dai, H. Chin. J. Org. Chem. 2018, 38, 3318(in Chinese). (周钱, 郑丹丹, 石玉军, 姚炜, 钱宏炜, 丁颖, 魏中昊, 沈爱宝, 冯霞, 石健, 戴红, 有机化学, 2018, 38, 3318.)
[24] Dai, H.; Yao, W.; Ye, L. Y.; Fang, Y.; Shi, Y. J.; Song, C.; Li, C. J.; Shi, J. Chin. J. Org. Chem. 2017, 37, 2165(in Chinese). (戴红, 姚炜, 叶林玉, 方源, 石玉军, 宋婵, 李春建, 石健, 有机化学, 2017, 37, 2165.)
[25] Dai, H.; Huang, M. L.; Ge, S. S.; Sun, S. Y.; Shen, A. B.; Cheng, X. Y.; Li, C. J.; Shi, J. Chin. J. Org. Chem. 2017, 37, 3289(in Chinese). (戴红, 黄美岭, 葛书山, 孙思宇, 沈爱宝, 成晓燕, 李春建, 石健, 有机化学, 2017, 37, 3289.)
[26] Tanaka, A.; Terasawa, T.; Hagihara, H.; Sakuma, Y.; Ishibe, N.; Sawada, M.; Takasugi, H.; Tanaka, H. J. Med. Chem. 1998, 41, 2390.
[27] Park, H. J.; Lee, K.; Park, S. J.; Ahn, B.; Lee, J. C.; Cho, H. Y.; Lee, K. I. Bioorg. Med. Chem. Lett. 2005, 15, 3307.
[28] Dai, H.; Chen, J.; Li, H.; Dai, B. J.; He, H. B.; Fang, Y.; Shi, Y. J. Molecules 2016, 21, 276.

含1,3,4-噁二唑结构的新型吡唑肟醚类衍生物的合成及杀虫活性

Synthesis and Insecticidal Activities of Novel Pyrazole Oxime Ethers Carrying 1,3,4-Oxadiazole Unit

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[2]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[3]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[4]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[5]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[6]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[7]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[8]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[9]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[10]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[11]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[12]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[13]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.
[14]	Ran Zhou, Chunmei Yuan, Tao Zhang, Piao Mao, Yi Liu, Kaini Meng, Hui Xin, Wei Xue. Design, Synthesis and Bioactivity of Chalcone Derivative Containing Quinazolinone [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3196-3209.
[15]	Ruixia Cao, Yuping Jia. Synthesis and Biological Activity of Novel Pyrrolo[2,3-d]pyrimidine Derivatives Containing Coumarin [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3304-3311.