Notes

Synthesis and Bioactivity of Novel 1-Methyl-3-trifluoromethyl- 5-subsituent-1H-pyrazole-4-carbaldehyde- O-(4-trifluoromethylbenzoyl)oximes

  • Dai Hong ,
  • Li Hong ,
  • Jin Zhichao ,
  • Liu Wenyong ,
  • Xiao Yao ,
  • He Haibing ,
  • Wang Qingmin ,
  • Shi Yujun
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  • a College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019;
    b State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071;
    c Nantong Fengtian Chemical Industry Co. Ltd, Nantong 226005

Received date: 2015-08-29

  Revised date: 2015-10-08

  Online published: 2015-10-23

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21202089, 21372135), the Natural Science Foundation of Jiangsu Province (No. BK20140425), and the Science and Technology Project Fund of Nantong City (Nos. AS2013004, CP12013002, AS2014011).

Abstract

In order to find novel pesticide from pyrazole compounds, a series of new pyrazole derivatives carrying trifluoromethyl benzoyl oxime ester moiety were prepared. The structures of all the title compounds were determined by 1H NMR, 13C NMR, MS and elemental analysis. Preliminary bioassay displayed that most of the target compounds showed certain insecticidal activities at the concentration of 500 μg/mL. When the concentration was reduced to 200 μg/mL, compounds 5b, 5c, 5d, 5i, 5l and 5n were still active against Aphis craccivora with inhibitory values of 90%, 90%, 80%, 80%, 80% and 80%, respectively.

Cite this article

Dai Hong , Li Hong , Jin Zhichao , Liu Wenyong , Xiao Yao , He Haibing , Wang Qingmin , Shi Yujun . Synthesis and Bioactivity of Novel 1-Methyl-3-trifluoromethyl- 5-subsituent-1H-pyrazole-4-carbaldehyde- O-(4-trifluoromethylbenzoyl)oximes[J]. Chinese Journal of Organic Chemistry, 2016 , 36(1) : 185 -190 . DOI: 10.6023/cjoc201508028

References

[1] Motoba, K.; Nishizawa, H.; Suzuki, T.; Hamaguchi, H.; Uchida, M.; Funayama, S. Pestic. Biochem. Physiol. 2000, 67, 73.
[2] Lahm, G. P., Selby, T. P.; Lahm, G. P., Freudenberger, J. H.; Stevenson, T. M.; Myers, B. J.; Seburyamo, G.; Smith, B. K.; Flexner, L.; Clark, C. E.; Cordova, D. Bioorg. Med. Chem. Lett. 2005, 15, 4898.
[3] 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.
[4] Zhao, P. L.; Wang, L.; Zhu, X. L.; Huang, X. Q.; Zhan, C. G.; Wu, J. W.; Yang, G. F. J. Am. Chem. Soc. 2010, 132, 185.
[5] Li, Y. X.; Lin, L.; Chen, Q. Chin. J. Org. Chem. 2011, 31, 306 (in Chinese). (李元祥, 林龙, 陈琼, 有机化学, 2011, 31, 306.)
[6] Dai, H.; Liu, J. B.; Miao, W. K.; Wu, S. S.; Qin, X.; Zhang, X.; Wang, T. T.; Fang, J. X. Chin. J. Org. Chem. 2011, 31, 1662 (in Chinese). (戴红, 刘建兵, 苗文科, 吴珊珊, 秦雪, 张欣, 王婷婷, 方建新, 有机化学, 2011, 31, 1662.)
[7] Liang, Y.; He, H. W.; He, H. F.; Yang, Z. W. Chin. J. Org. Chem. 2012, 32, 1513 (in Chinese). (梁英, 贺红武, 何海峰, 杨自文, 有机化学, 2012, 32, 1513.)
[8] El-Moghazy, S. M.; Barsoum, F. F.; Abdel-Rahman, H. M.; Marzouk, A. A. Med. Chem. Res. 2012, 21, 1722.
[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] Dai, H.; Yu, H. B.; Liu, J. B.; Qin, X.; Wang, T. T.; Zhang, X.; Qin, Z. F.; Fang, J. X. Chin. J. Org. Chem. 2013, 33, 1104 (in Chinese). (戴红, 于海波, 刘建兵, 秦雪, 王婷婷, 张欣, 秦振芳, 方建新, 有机化学, 2013, 33, 1104.)
[11] Selby, T. P.; Lahm, G. P.; Stevenson, T. M.; Hughes, K. A.; Cordova, D.; Annan, I. B.; Barry, J. D.; Benner, E. A.; Currie, M. J.; Pahutski, T. F. Bioorg. Med. Chem. Lett. 2013, 23, 6341.
[12] Guo, C. P.; Peng, Q. L.; Pan, L.; Zhang, D. M.; Chen, H. R. Chin. J. Org. Chem. 2014, 34, 2505 (in Chinese). (国翠平, 彭群龙, 潘龙, 张冬梅, 陈河如, 有机化学, 2014, 34, 2505.)
[13] Xiong, L.; Zhu, X. L.; Shen, Y. Q.; Wishwa, W. K. W. M.; Li, K.; Yang, G. F. Eur. J. Med. Chem. 2015, 95, 424.
[14] Hamaguchi, H.; Kajihara, O.; Katoh, M. J. Pestic. Sci. 1995, 20, 173.
[15] Chen, L.; Ou, X. M.; Mao, C. H.; Shang, J.; Huang, R. Q.; Bi, F. C.; Wang, Q. M. Bioorg. Med. Chem. 2007, 15, 3678.
[16] Song, H. J.; Liu, Y. X.; Xiong, L. X.; Li, Y. Q.; Yang, N.; Wang, Q. M. J. Agric. Food Chem. 2013, 61, 8730.
[17] Wang, S. L.; Shi, Y. J.; He, H. B.; Li, Y.; Li, Y.; Dai, H. Chin. Chem. Lett. 2015, 26, 672.
[18] Liu, C. L.; Liu, X. N.; Zhang, H.; Lei, X.; Liu, W. C.; Zhang, L. X.; Li, B.; Man, Y.; Hu, X. Z.; Li, Z. C. CN 1188764, 2000 [Chem. Abstr. 2000, 132, 176977].
[19] 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.
[20] Dai, H.; Xiao, Y. S.; Li, Z.; Xu, X. Y.; Qian, X. H. Chin. Chem. Lett. 2014, 25, 1014.
[21] Lü, Q.; Lu, X. T.; Dai, M.; Liu, S. M.; Zhu, W. H.; Du, P.; Lü, L. Chin. J. Org. Chem. 2015, 35, 1260 (in Chinese). (吕强, 芦昕婷, 戴明, 刘世梦, 朱为宏, 杜葩, 吕龙, 有机化学, 2015, 35, 1260.)
[22] Peng, H.; He, H. W. Chin. J. Org. Chem. 2007, 27, 502 (in Chinese). (彭浩, 贺红武, 有机化学, 2007, 27, 502.)
[23] Wang, D.; Wei, Y.; Hao, S. H. Chin. J. Org. Chem. 2015, 35, 1691 (in Chinese). (王栋, 魏艳, 郝双红, 有机化学, 2015, 35, 1691.)
[24] Xu, Y.; Lei, P.; Ling, Y.; Wang, S. W.; Yang, X. L. Chin. J. Org. Chem. 2014, 34, 1118 (in Chinese). (徐炎, 雷鹏, 凌云, 王圣文, 杨新玲, 有机化学, 2014, 34, 1118.)
[25] Lee, L. F.; Schleppnik, F. M.; Schneider, R. W.; Campbell, D. H. J. Heterocycl. Chem. 1990, 27, 243.
[26] Dai, H.; Li, Y. Q.; Du, D.; Qin, X.; Zhang, X.; Yu, H. B.; Fang, J. X. J. Agric. Food Chem. 2008, 56, 10805.
[27] Dai, H.; Shen, Y. F.; Chen, J.; Chen, H. L.; Shen, Y. J. Acta Crystallogr. 2011, E67, o726.
[28] Dai, H.; Miao, W. K.; Wu, S. S.; Qin, X.; Fang, J. X. Acta Crystallogr. 2011, E67, o775.
[29] Hu, W. Q.; Zhu, W. G.; Chen, D. H. Chin. J. Pestic. Sci. 2007, 9, 240 (in Chinese). (胡伟群, 朱卫刚, 陈定花, 农药学学报, 2007, 9, 240.)

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