Synthesis and Insecticidal Activities of Novel Pyrazole Amide Derivatives Containing a Thiazole Unit

doi:10.6023/cjoc202001029

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (6): 1665-1672.DOI: 10.6023/cjoc202001029 Previous Articles Next Articles

含噻唑环结构的新型吡唑酰胺类化合物的合成与杀虫活性研究

梁凯^a, 周钱^a, 荀校^a, 倪亚丹^a, 李金峰^a, 石玉军^a, 周环宇^a, 吴新星^a, 石健^b, 高磊^a, 戴红^a

a 南通大学化学化工学院江苏南通 226019;
b 南通大学分析测试中心江苏南通 226019

收稿日期:2020-01-22 修回日期:2020-02-25 发布日期:2020-03-04
通讯作者: 石玉军, 吴新星, 戴红 E-mail:yjshi2015@163.com;wuxinxng@163.com;daihong_2015@aliyun.com
基金资助:
国家自然科学基金（Nos.21372135）、南通市科技计划（No.MS12019060）和南通大学高层次人才（No.03083031）资助项目.

Synthesis and Insecticidal Activities of Novel Pyrazole Amide Derivatives Containing a Thiazole Unit

Liang Kai^a, Zhou Qian^a, Xun Xiao^a, Ni Yadan^a, Li Jinfeng^a, Shi Yujun^a, Zhou Huanyu^a, Wu Xinxing^a, Shi Jian^b, Gao Lei^a, Dai Hong^a

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

Received:2020-01-22 Revised:2020-02-25 Published:2020-03-04
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21372135), the Science and Technology Project Fund of Nantong City (No. MS12019060) and the Program of High-level Talents of Nantong University (No. 03083031).

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Abstract

In search of novel pyrazole amide compounds possessing good biological activities, a series of pyrazole amides were synthesized by introducing thiazole unit into pyrazole ring via amido bond, based on the lead of tebufenpyrad. The title compounds were structurually confirmed by ¹H NMR, ¹³C NMR and elemental analysis. Preliminary bioassay displayed that all the title compounds exhibited 100% insecticidal activities against Oriental armyworm at 500 μg/mL. At the concentration of 500 μg/mL, seven compounds showed 70%~100% mortality rate against Aphis medicaginis. In addition, three compounds had 40%~50% insecticidal activity against Tetranychus cinnabarinus at 500 μg/mL.

Key words: thiazole, pyrazole amide, synthesis, insecticidal activity

Cite this article

Liang Kai, Zhou Qian, Xun Xiao, Ni Yadan, Li Jinfeng, Shi Yujun, Zhou Huanyu, Wu Xinxing, Shi Jian, Gao Lei, Dai Hong. Synthesis and Insecticidal Activities of Novel Pyrazole Amide Derivatives Containing a Thiazole Unit[J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1665-1672.

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[1] Prakash, T. B.; Reddy, G. D.; Padmaja, A.; Padmavathi, V. Eur. J. Med. Chem. 2014, 82, 347.
[2] Guan, A. Y.; Qin, Y. K.; Wang, J. F.; Li, B. J. Fluorine Chem. 2013, 156, 120.
[3] Li, G. Y.; Qian, X. H.; Cui, J. N.; Huang, Q. C.; Zhang, R.; Guan, H. J. Agric. Food Chem. 2006, 54, 125.
[4] Ohnmacht, S. A.; Ciancimino, C.; Vignaroli, G.; Gunaratnam, M.; Neidle, S. Bioorg. Med. Chem. Lett. 2013, 23, 5351.
[5] 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.
[6] Liu, X. H.; Zhao, W.; Shen, Z. H.; Xing, J. H.; Xu, T. M.; Peng, W. L. Eur. J. Med. Chem. 2017, 125, 881.
[7] Shi, J. J.; Ren, G. H.; Wu, N. J.; Weng, J. Q.; Xu, T. M.; Liu, X. H.; Tan, C. X. Chin. Chem. Lett. 2017, 28, 1727.
[8] Wang, B. L.; Zhu, H. W.; Li, Z. M.; Wang, L. Z.; Zhang, X.; Xiong, L. X.; Song, H. B. Pest Manage. Sci. 2018, 74, 726.
[9] Yu, H. B.; Qin, Z. F.; Dai, H.; Zhang, X.; Qin, X.; Wang, T. T.; Fang, J. X. J. Agric. Food Chem. 2008, 56, 11356.
[10] Wang, H. L.; Ruan, L. L.; Chen, Y.; Liu, X. H.; Weng, J. Q. Chin. J. Org. Chem. 2015, 34, 419(in Chinese). (王海林, 阮铃莉, 陈勇, 刘幸海, 翁建全, 有机化学, 2015, 34, 419.)
[11] Pember, S. O.; Mejia, G. L.; Price, T. J.; Pasteris, R. J. Bioorg. Med. Chem. Lett. 2016, 26, 2965.
[12] Mabkhot, Y. N.; Alharbi, M. M.; Al-Showiman, S. S.; Ghabbour, H. A.; Kheder, H. A.; Soliman, S. M.; Frey, W. Chem. Cent. J. 2018, 12, 56.
[13] Althagafi, I.; El-Metwaly, N.; Farahaly, T. A. Molecules 2019, 24, 1741.
[14] Maienfisch, P. L.; Huerlimann, H.; Rindlisbacher, A.; Gsell, L.; Dettwiler, H.; Haettenschwiler, J.; Sieger, E.; Walti, M. Pest Manage. Sci. 2001, 57, 165.
[15] Cao, S. W.; Liu, A. P.; Liu, W. D.; Liu, X. P.; Ren, Y. G.; Pei, H.; Huang, L.; Zheng, X.; Huang, M. Z.; Wu, D. X. J. Heterocycl. Chem. 2017, 54, 3395.
[16] Ding, C. R.; Pan, Y. Y.; Yin, X.; Tan, C. X.; Zhang, G. F. Chin. J. Org. Chem. 2019, 39, 836(in Chinese). (丁成荣, 潘亚运, 殷许, 谭成侠, 张国富, 有机化学, 2019, 39, 836.)
[17] Ding, C. R.; Pan, Y. Y.; Yin, X.; Tan, C. X. Chin. J. Org. Chem. 2019, 39, 2099(in Chinese). (丁成荣, 潘亚运, 殷许, 谭成侠, 有机化学, 2019, 39, 2099.)
[18] Dai, H.; Li, G.; Chen, J.; Shi, Y. J.; Ge, S. S.; Fan, C. G.; He, H. B. Bioorg. Med. Chem. Lett. 2016, 26, 3818.
[19] Dai, H.; Chen, J.; Li, G.; Ge, S. S.; Shi, Y. J.; Fang, Y.; Ling, Y. Bioorg. Med. Chem. Lett. 2017, 27, 950.
[20] Monicka, J. C.; James, C. J. Mol. Struct. 2014, 1075, 335.
[21] Fulcher, J. M.; Wayment, D. G.; White, Jr, P. M.; Webber III, C. L.; J. Agric. Food Chem. 2014, 62, 2141.
[22] 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.
[23] Gu, B. Q.; Zhu, W. Q.; Fan, W. Z.; Qian, H.; Liu, J. M.; Zhang, A. Q.; Shen, R. X. Modern Agrochem. 2002, 1, 9(in Chinese). (顾保权, 朱伟清, 范文政, 钱虹, 刘建梅, 张爱庆, 沈荣仙, 现代农药, 2002, 1, 9.)
[24] Fan, W. Z.; Gu, B. Q.; Zhu, W. Q.; Zhang, Y. B. Modern Agrochem. 2005, 4, 9(in Chinese). (范文政, 顾保权, 朱伟清, 张一宾, 现代农药, 2005, 4, 9.)
[25] Hughes, K. A.; Lahm, G. P.; Selby, T. P.; Stevenson, T. M. WO 2004067528, 2004[Chem. Abstr. 2004, 141, 190786].
[26] Hamaguchi, H.; Kajihara, O.; Katoh, M. J. Pestic. Sci. 1995, 20, 173.
[27] Yang, Z. B.; Hu, D. Y.; Zeng, S.; Song, B. A. Bioorg. Med. Chem. Lett. 2016, 26, 1161.
[28] Zhao, W.; Shen, Z. H.; Xu, T. M.; Peng, W. L.; Liu, X. H. J. Heterocycl. Chem. 2017, 54,1751.
[29] Cheng, L.; Shen, Z. H.; Xu, T. M.; Tan, C. X.; Weng, J. Q.; Han, L.; Peng, W. L.; Liu, X. H. J. Heterocycl. Chem. 2018, 55, 946.
[30] Lima, L. M. A.; Barreiro, E. J. Curr. Med. Chem. 2005, 12, 23.
[31] Romagnoli, R.; Baraldi, P. G.; Salvador, M. K.; Preti, D.; Tabrizi, M. A.; Brancale, A.; Fu, X. H.; Li, J.; Zhang, S. Z.; Hamel, E.; Bortolozzi, R.; Basso, G.; Viola, G. J. Med. Chem. 2012, 55, 475.
[32] Wang, Q. M.; Li, H.; Li, Y. H.; Huang, R. Q. J. Agric. Food Chem. 2004, 52, 1918.
[33] Liu, Y. X.; Wei, D. G.; Zhu, Y. R.; Liu, S. H.; Zhang, Y. L.; Zhao, Q. Q.; Cai, B. L.; Li, Y. H.; Song, H. B.; Liu, Y.; Wang, Y.; Huang, R. Q.; Wang, Q. M. J. Agric. Food Chem. 2008, 56, 204.
[34] Dai, H.; Li, Y. Q.; Du, D.; Qin, X.; Zhang, X.; Yu, H. B.; Fang, J. X. J. Agric. Food Chem. 2008, 56, 10805.
[35] Yang, Y. Z.; Lin, D. Y.; Fu, C. R.; Zou, X. M. Chin. J. Org. Chem. 2015, 35, 100(in Chinese). (杨亚喆, 林大勇, 傅翠蓉, 邹小毛, 有机化学, 2015, 35, 100.)
[36] Wang, B. L.; Zhu, H. W.; Ma, Y.; Xiong, L. X.; Li, Y. Q.; Zhao, Y.; Zhang, J. F.; Chen, Y. W.; Zhou, S.; Li, Z. M. J. Agric. Food Chem. 2013, 61, 5483.
[37] Dai, H.; Yao, W.; Fang, Y.; Sun, S. Y.; Shi, Y. J.; Chen, J.; Jiang, G. Q.; Shi, J. Molecules 2017, 22, 2000.
[38] 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.)
[39] Shao, L.; Zhou, X.; Zhang, Q.; Liu, J. B.; Jin, Z.; Fang, J. X. Synth. Commun. 2007, 37, 199.

含噻唑环结构的新型吡唑酰胺类化合物的合成与杀虫活性研究

Synthesis and Insecticidal Activities of Novel Pyrazole Amide Derivatives Containing a Thiazole Unit

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