Synthesis and Bioactivity of Novel 1-Methyl-3-trifluoromethyl-5-subsituent-1H-pyrazole-4-carbaldehyde-O-(4-trifluoromethylbenzoyl)oximes
- Corresponding author: He Haibing, hhb3812@163.com Shi Yujun, yjshi2015@163.com
Citation:
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,
;2015, 36(1): 185-190.
doi:
10.6023/cjoc201508028
Motoba, K.; Nishizawa, H.; Suzuki, T.; Hamaguchi, H.; Uchida, M.; Funayama, S. Pestic. Biochem. Physiol. 2000, 67, 73.
doi: 10.1006/pest.2000.2477
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.
doi: 10.1016/j.bmcl.2005.08.034
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.
doi: 10.1021/jf802489e
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.
doi: 10.1021/ja905756c
Li, Y. X.; Lin, L.; Chen, Q. Chin. J. Org. Chem. 2011, 31, 306 (in Chinese).
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).
Liang, Y.; He, H. W.; He, H. F.; Yang, Z. W. Chin. J. Org. Chem. 2012, 32, 1513 (in Chinese).
doi: 10.6023/cjoc1201041
El-Moghazy, S. M.; Barsoum, F. F.; Abdel-Rahman, H. M.; Marzouk, A. A. Med. Chem. Res. 2012, 21, 1722.
doi: 10.1007/s00044-011-9691-4
Sun, N. B.; Tong, J. Y.; Wu, H. K. Chin. J. Org. Chem. 2013, 33, 101 (in Chinese).
doi: 10.6023/cjoc201208019
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).
doi: 10.6023/cjoc201211047
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.
doi: 10.1016/j.bmcl.2013.09.076
Guo, C. P.; Peng, Q. L.; Pan, L.; Zhang, D. M.; Chen, H. R. Chin. J. Org. Chem. 2014, 34, 2505 (in Chinese).
doi: 10.6023/cjoc201407042
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.
doi: 10.1016/j.ejmech.2015.03.060
Hamaguchi, H.; Kajihara, O.; Katoh, M. J. Pestic. Sci. 1995, 20, 173.
doi: 10.1584/jpestics.20.173
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.
doi: 10.1016/j.bmc.2007.03.049
Song, H. J.; Liu, Y. X.; Xiong, L. X.; Li, Y. Q.; Yang, N.; Wang, Q. M. J. Agric. Food Chem. 2013, 61, 8730.
doi: 10.1021/jf402719z
Wang, S. L.; Shi, Y. J.; He, H. B.; Li, Y.; Li, Y.; Dai, H. Chin. Chem. Lett. 2015, 26, 672.
doi: 10.1016/j.cclet.2015.04.017
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].
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.
doi: 10.1002/ps.2014.70.issue-8
Dai, H.; Xiao, Y. S.; Li, Z.; Xu, X. Y.; Qian, X. H. Chin. Chem. Lett. 2014, 25, 1014.
doi: 10.1016/j.cclet.2014.06.011
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).
doi: 10.6023/cjoc201412032
Peng, H.; He, H. W. Chin. J. Org. Chem. 2007, 27, 502 (in Chinese).
Wang, D.; Wei, Y.; Hao, S. H. Chin. J. Org. Chem. 2015, 35, 1691 (in Chinese).
doi: 10.6023/cjoc201504008
Xu, Y.; Lei, P.; Ling, Y.; Wang, S. W.; Yang, X. L. Chin. J. Org. Chem. 2014, 34, 1118 (in Chinese).
doi: 10.6023/cjoc201401034
Lee, L. F.; Schleppnik, F. M.; Schneider, R. W.; Campbell, D. H. J. Heterocycl. Chem. 1990, 27, 243.
doi: 10.1002/jhet.v27:2
Dai, H.; Li, Y. Q.; Du, D.; Qin, X.; Zhang, X.; Yu, H. B.; Fang, J. X. J. Agric. Food Chem. 2008, 56, 10805.
doi: 10.1021/jf802429x
Dai, H.; Shen, Y. F.; Chen, J.; Chen, H. L.; Shen, Y. J. Acta Crystallogr. 2011, E67, o726.
Dai, H.; Miao, W. K.; Wu, S. S.; Qin, X.; Fang, J. X. Acta Crystallogr. 2011, E67, o775.
Hu, W. Q.; Zhu, W. G.; Chen, D. H. Chin. J. Pestic. Sci. 2007, 9, 240 (in Chinese).
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5a: Y=2-CH3C6H4O, 5b: Y=3-CH3C6H4O, 5c: Y=4-CH3C6H4O, 5d: Y=4-t-C4H9C6H4O, 5e: Y=2-CH3OC6H4O, 5f: Y=4-OCH3C6H4O, 5g: Y=C6H5O; 5h: Y=2-ClC6H4O, 5i:Y=3-ClC6H4O, 5j: Y=4-Cl-C6H4O; 5k: Y=2-BrC6H4O, 5l: Y=4-BrC6H4O, 5m: Y=2, 6-(CH3)2-C6H3O, 5n: Y=3, 4-(CH3)2C6H3O, 5o: Y=6-Cl-3-CH3C6H3O, 5p: Y=1H-benzo[d] [1,2,3] triazolyl