Chinese Journal of Organic Chemistry >
Synthesis and Insecticidal Activities of Novel Pyrazole Amides Containing Heptafluoroisopropyl Moiety
Received date: 2017-07-20
Revised date: 2017-08-15
Online published: 2017-08-18
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. 201610304047Z) and the Science and Technology Innovation Foundation for the Graduate Students of Nantong University (No. YKC16086).
In order to find new pyrazole derivatives with potent biological activities, a series of novel pyrazole amides containing heptafluoroisopropyl moiety were prepared according to the method of active substructure combination. Their structures were characterized by 1H NMR, 13C NMR and elemental analysis. Preliminary bioassay data showed that some target compounds displayed good insecticidal activities. At the concentration of 500 μg/mL, eleven compounds had insecticidal activity against Oriental armyworm of 60%~100%. When the concentration was reduced to 100 μg/mL, three compounds showed insecticidal activity against Oriental armyworm of 60%~70%, better than that of the control tolfenpyrad.
Key words： heptafluoroisopropyl; pyrazole; synthesis; insecticidal activity
Hong Yu , Dai Hong , Ye Linyu , Zhong Sulin , Cao Xiongfei , Shi Yujun , Li Chunjian , Shi Jian , Shi Lei . Synthesis and Insecticidal Activities of Novel Pyrazole Amides Containing Heptafluoroisopropyl Moiety[J]. Chinese Journal of Organic Chemistry, 2017 , 37(11) : 3006 -3012 . DOI: 10.6023/cjoc201707022
[1] Zang, C. R.; Wang, L.; Ge, Y. L.; Ju, X. L. Chin. J. Org. Chem. 2007, 27, 1432(in Chinese). (张成仁, 王柳, 葛燕丽, 巨修练, 有机化学, 2007, 27, 1432.)
[2] Zhang, X. B.; Zhang, Z. M.; Zhang, Y. G.; Li, M. Chin. J. Org. Chem. 2009, 29, 297(in Chinese). (张小兵, 张子敏, 张玉贵, 李敏, 有机化学, 2009, 29, 297.)
[3] Kang, S.; Song, B. A.; Wu, J.; He, M.; Hu, D. Y.; Jin, L. H.; Zeng, S.; Xue, W.; Yang, S. Eur. J. Med. Chem. 2013, 67, 14.
[4] Song, H. J.; Liu, Y. X.; Xiong, L. X.; Li, Y. Q.; Yang, N.; Wang, Q. M. J. Agric. Food Chem. 2012, 60, 1470.
[5] Li, M.; Liu, R. L.; Yang, H.; Zhang, H.; Liu, C. L.; Li, Z. M. Agrochemicals 2008, 47, 874(in Chinese). (李淼, 刘若霖, 杨浩, 张弘, 刘长令, 李正名, 农药, 2008, 47, 874.)
[6] Chen, X.; Xiao, Y.; Wang, G.; Li, Z.; Xu, X. Res. Chem. Intermed. 2015, 42, 1.
[7] Tan, C, X.; Shen, D. L.; Weng, J. Q.; Ou, X. M. Chin. J. Org. Chem. 2005, 25, 1454(in Chinese). (谭成侠, 沈德隆, 翁建全, 欧晓明, 有机化学, 2005, 25, 1454.)
[8] Mu, J. X.; Shi, Y. X.; Yang, M. Y.; Sun, Z. H.; Liu, X. H.; Li, B. J.; Sun, N. B. Molecules 2016, 21, 68.
[9] Sun, N. B.; Tong, J. Y.; Wu, H. K. Chin. J. Org. Chem. 2013, 33, 101(in Chinese). (孙娜波, 童建颖, 武宏科, 有机化学, 2013, 33, 101.)
[10] Abdel-Aziz, H. A.; El-Zahabi, H. S. A.; Dawood, K. M. Eur. J. Med. Chem. 2010, 45, 2427.
[11] Miyamoto, N.; Sakai, N.; Hirayama, T.; Miwa, K.; Oguro, Y.; Oki, H. Bioorg. Med. Chem. 2013, 21, 2333.
[12] Ding, X. L.; Zhang, H. Y.; Qi, L.; Zhao, B. X.; Lian, S.; Lv, H. S. Bioorg. Med. Chem. Lett. 2009, 19, 5325.
[13] Gu, B. Q.; Zhu, W. Q.; Fan, W. Z.; Qian, H.; Liu, J. M.; Zhang, A. Q.; Shen, R. X. Mod. 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.)
[14] Fan, W. Z.; Gu, B. Q.; Zhu, W. Q.; Zhang, Y. B. Mod. 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.)
[15] Liu, J.; Xie, H. P.; Song, B. A.; Hu, D. Y.; Yang, S.; Jin, L. H. Chin. J. Org. Chem. 2010, 30, 1347(in Chinese). (刘杰, 谢化鹏, 宋宝安, 胡德禹, 杨松, 金林红, 有机化学, 2010, 30, 1347.)
[16] Loska, L.; MaKosza, M. J. Org. Chem. 2007, 72, 1354.
[17] Feng, Q.; Liu, Z. L.; Wang, M. Z.; Xiong, L. X., Gan, S. J.; Li, Z. M. Chem. J. Chin. Univ. 2011, 32, 74(in Chinese). (冯启, 刘智力, 王明忠, 熊丽霞, 于淑晶, 李正名, 高等学校化学学报, 2011, 32, 74.)
[18] Meng. D. X.; Zhou, S.; Xie, Y. T.; Zhao, L.; Xiong, L. X.; Zhou, S.; Li, Z. M. Chin. J. Org. Chem. 2017, 37, 908(in Chinese). (孟祥德, 周沙, 解永涛, 赵毓, 熊丽霞, 周莎, 李正名, 有机化学, 2017, 37, 908.)
[19] Chen, Y. W.; Wan, Y. Y.; Liu, Q. X.; Liu, J. B.; Xiong, L. X.; Yu, S. J.; Li, Z. M. Chin. J. Org. Chem. 2014, 35, 882(in Chinese). (陈有为, 万莹莹, 刘巧霞, 刘敬波, 熊丽霞, 于淑晶, 李正名, 有机化学, 2014, 35, 882.)
[20] Zhang, J.; Tang, X.; Ishaaya, I.; Cao, S.; Wu, J.; Yu, J. J. Agric. Food Chem. 2010, 58, 2736.
[21] Wang, Z. J.; Liu, B.; Li, Y. H.; Zhao, W. G. Chin. J. Org. Chem. 2011, 31, 317(in Chinese). (王振军, 刘斌, 李永红, 赵卫光, 有机化学, 2011, 31, 317.)
[22] Dai, H.; Liu, J. B.; Miao, W. K.; Wu, S. S.; Zhang, X.; Wang, T. T.; Fang, J. X. Chin. J. Org. Chem. 2011, 31, 1943(in Chinese). (戴红, 刘建兵, 苗文科, 吴珊珊, 张欣, 王婷婷, 方建新, 有机化学, 2011, 31, 1943.)
[23] Sheng, G. Z.; Zhang, W. Chin. J. Org. Chem. 2013, 33, 2271(in Chinese). (盛国柱, 张炜, 有机化学, 2013, 33, 2271.)
[24] Wei, F.; Zhao, B. X.; Huang, B.; Zhang, L.; Sun, C. H.; Dong, W. L.; Shin, D. S.; Miao, J. Y. Bioorg. Med. Chem. Lett. 2006, 16, 6342.
[25] Zhou, Z. W. M.S. Thesis, Hunan University of Science and Technology, Hunan, 2011. (周仲伟, 硕士论文, 湖南科技大学, 湖南, 2011.)
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