Chinese Journal of Organic Chemistry >
Synthesis and Biological Activities of Novel Pyrazole Amide Derivatives Containing Substituted Pyridyl Group
Received date: 2018-06-20
Revised date: 2018-07-19
Online published: 2018-08-14
Supported by
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), the Science and Technology Project Fund of Nantong City (No. MS22015020), the Science and Technology Innovation Foundation for the College Students of Jiangsu Province (No. 201810304016Z) and the Science Foudation of Nantong University Xinglin College (No. 2016K130).
In order to find novel pyrazole amides having potent bioactivities, a series of novel pyrazole amide compounds carrying substituted pyridyl moiety were designed and synthesized according to the method of active substructure combination. The preliminary bioassay data showed that some title compounds displayed good insecticidal activities. At the concentration of 500 μg/mL, ten compounds exhibited insecticidal activity against Oriental armyworm with 60%~100%, and one compound indicated insecticidal activity against Aphis medicaginis with 100%. When the concentration was reduced to 100 μg/mL, two compounds still showed insecticidal activity against Oriental armyworm with 70%~100%, which were better than that of the control tolfenpyrad. Additionally, one compound displayed 50% insecticidal activity against Oriental armyworm at the concentration of 20 μg/mL.
Key words: pyridine; pyrazole amide; synthesis; bioactivity
Shi Yujun , Zhou Qian , Wang Yang , Qian Hongwei , Ye Linyu , Feng Xia , Chen Hui , Li Yating , Dai Hong , Wei Zhonghao , Wu Jinming . Synthesis and Biological Activities of Novel Pyrazole Amide Derivatives Containing Substituted Pyridyl Group[J]. Chinese Journal of Organic Chemistry, 2018 , 38(9) : 2450 -2457 . DOI: 10.6023/cjoc201806030
[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, Y. Q.; Du, D.; Qin, X.; Zhang, X.; Yu, H. B.; Fang, J. X. J. Agric. Food Chem. 2008, 56, 10805.
[3] Dai, H.; Zhuang. H. Y.; Shi, L.; Li, G.; Zhang, H. J.; Fang, Y.; Dai, B. J. Chin. J. Org. Chem. 2015, 35, 2399(in Chinese). (戴红, 庄辉阳, 施磊, 李刚, 张海军, 方源, 戴宝江, 有机化学, 2015, 35, 2399.)
[4] 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.)
[5] Shi, J. J.; Ren, G. H.; Wu, N. J.; Liu, X. H.; Xu. T. M.; Tan, C. X. Chin. J. Org. Chem. 2017, 37, 2131(in Chinese). (史建俊, 任贵华, 吴宁捷, 刘幸海, 许天明, 谭成侠, 有机化学, 2017, 37, 2131.)
[6] 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.
[7] Liu, X. H.; Zhao, W.; Shen, Z. H.; Xing, J. H.; Xu, T. M.; Peng, W. L. Eur. J. Med. Chem. 2017, 125, 881.
[8] 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.
[9] Liu, T. T.; Ni, Y.; Zhong, L. K.; Huang, H. Y.; Hu. W. Q.; Xu. T. M.; Tan, C. X. Chin. J. Org. Chem. 2015, 35, 422(in Chinese). (刘婷婷, 倪芸, 钟良坤, 黄红英, 胡伟群, 许天明, 谭成侠, 有机化学, 2015, 35, 422.)
[10] Pirol, S. C.; Caliskan, B.; Durmaz, I.; Atalay, R.; Banoglu, E. Eur. J. Med. Chem. 2014, 87, 140.
[11] 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.)
[12] Fan, W. Z.; Gu, B. Q.; Zhu, W. Q.; Zhang, Y. B. Modern Agro-chem. 2005, 4, 9(in Chinese). (范文政, 顾保权, 朱伟清, 张一宾, 现代农药, 2005, 4, 9.)
[13] Song, H. J.; Liu, Y. X.; Xiong, L. X.; Li, Y. Q.; Yang, N.; Wang, Q. M. J. Agric. Food Chem. 2013, 61, 8730.
[14] Zhou, Y. Y.; Wang, B. L.; Di, F. J.; Xiong, L. X.; Yang, N.; Li, Y. Q.; Li, Y. X.; Li, Z. M. Bioorg. Med. Chem. Lett. 2014, 24, 2295.
[15] 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.
[16] Dai, H.; Shi, L.; Zhang, H. J.; Li, Y. Q.; Fang, J. X.; Shi, Y. J. Chin. J. Org. Chem. 2012, 32, 1060(in Chinese). (戴红, 施磊, 张海军, 李永强, 方建新, 石玉军, 有机化学, 2012, 32, 1060.)
[17] Wang, X.; Wang, C. Q.; Fu, C. R.; Zou, X. M. Chin. J. Org. Chem. 2015, 35, 92(in Chinese). (王鑫, 王朝强, 傅翠蓉, 邹小毛, 有机化学, 2015, 35, 92.)
[18] Dai, H.; Chen, J.; Hong, Y.; Yuan, B. Y.; Fan, C. G.; Ma, R. Y.; Liang, Z. P.; Shi, J. Chin. J. Org. Chem. 2017, 37, 1542(in Chinese). (戴红, 陈佳, 洪宇, 袁斌颖, 范崇光, 马瑞媛, 梁志鹏, 石健, 有机化学, 2017, 37, 1542.)
[19] Sakamoto, N.; Saito, S.; Hirose, T.; Suzuki, M.; Matsuo, S.; Izumi, K,; Nagatomi, T.; Ikegami, H.; Umeda, K.; Tsushima, K.; Matsuo, N. Pest Manage. Sci. 2003, 60, 25.
[20] Saito, S.; Ysoshioka, T.; Umeda, K. J. Pestic. Sci. 2006, 31, 335.
[21] Yu, F. Q.; Huang, Y. S.; Su, Z.; Wu, E. M.; Wang, W.; Yu, C. R. Chin. J. Pestic. 2013, 52, 753(in Chinese). (于福强, 黄耀师, 苏州, 武恩明, 王微, 于春睿, 农药, 2013, 52, 753.)
[22] Yu, F. Q.; Guan, A. Y.; Liu, C. L.; Sun, X. F.; Xie, Y.; Wang, M. A. Bioorg. Med. Chem. 2016, 24, 342.
[23] 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.)
[24] Liu, X. H.; Wang, Q.; Sun, Z. H.; Wedge, D. E.; Becnel, J. J.; Estep, A. S.; Tan, C. X. Weng, J. Q. Pest Manage. Sci. 2017, 73, 953.
[25] Shi, J. J.; Ren, G. H.; Dai, Z. M.; Wu, N, J.; Weng, J. Q.; Xu, T. M.; Liu, X. H.; Tan, C. X. Lett. Drug Des. Discovery 2018, 15, 15.
[26] Chen, L.; Shen, Z. H.; Xu, T. M.; Tan, C. X.; Weng, J. Q.; Han, L.; Peng. W. L.; Xiu, X. H. J. Heterocycl. Chem. 2018, 55, 946.
[27] 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.)
[28] Hong, Y.; Dai, H.; Ye, L. Y.; Zhong, S. L.; Cao, X. F.; Shi, Y. J.; Li, C. J.; Shi, J.; Shi, L. Chin. J. Org. Chem. 2017, 37, 3006(in Chinese). (洪宇, 戴红, 叶林玉, 仲苏林, 曹雄飞, 石玉军, 李春建, 石健, 施磊, 有机化学, 2017, 37, 3006.)
[29] Dai, H.; Chen, J.; Li, H.; Dai, B. J.; He, H. B.; Fang, Y.; Shi, Y. J. Molecules 2016, 21, 276.
[30] Liu, C. L.; Wang, L. Z.; Lan, J.; Sun, X. F.; Sun, Q.; Zhang, J. B. CN 103081916, 2013[Chem. Abstr. 2013, 158, 724382].
/
〈 |
|
〉 |