Synthesis and Bioactivities of Novel Pyrazole Oxime Ethers Containing Substituted Pyrazolyl Group
- Corresponding author: Shi Lei, gaohbhe2015@aliyun.com Shi Yujun, yjshi2015@163.com
Citation:
Dai Hong, Yao Wei, Sun Siyu, Li Ling, Shi Lei, Qian Hongwei, Li Chunjian, Shi Jian, Shi Yujun. Synthesis and Bioactivities of Novel Pyrazole Oxime Ethers Containing Substituted Pyrazolyl Group[J]. Chinese Journal of Organic Chemistry,
;2017, 37(12): 3155-3162.
doi:
10.6023/cjoc201708020
Li, Y.; Zhang, H. Q.; Liu, J.; Yang, X. P.; Liu, Z. J. J. Agric. Food Chem. 2006, 54, 3636.
doi: 10.1021/jf060074f
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
Hamaguchi, H.; Kajihara, O.; Katoh, M. J. Pestic. Sci. 1995, 20, 173.
doi: 10.1584/jpestics.20.173
Motoba, K.; Nishizawa, H.; Suzuki, T.; Hamaguchi, H.; Uchida, M.; Funayama, S. Pestic. Biochem. Physiol. 2000, 67, 73.
doi: 10.1006/pest.2000.2477
Park, H. J.; Lee, K.; Park, S. J.; Ahn, B.; Lee, J. C.; Cho, H. Y.; Lee, K. I. Bioorg. Med. Chem. Lett. 2005, 15, 3307.
doi: 10.1016/j.bmcl.2005.03.082
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).
Fan, W. Z.; Gu, B. Q.; Zhu, W. Q.; Zhang, Y. B. Modern Agrochem. 2005, 4, 9(in Chinese).
doi: 10.3969/j.issn.1671-5284.2005.02.002
Lahm, G. P., Selby, T. 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
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).
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).
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. 8, 56, 10160.
Hamaguchi, H.; Kajihara, O.; Katoh, M. J. Pestic. Sci. 1995, 20, 173.
doi: 10.1584/jpestics.20.173
Swanson, M. B.; Ivancic, W. A.; Saxena, A. M.; Allton, J. D.; O'Brien, G. K.; Suzuki, T.; Nishizawa, H.; Nokata, M. J. Agric. Food Chem. 1995, 43, 513.
doi: 10.1021/jf00050a048
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
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, 7.
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
Park, H. J.; Lee, K.; Park, S. J.; Ahn, B.; Lee, J. C.; Cho, H. Y.; Lee, K. I. Bioorg. Med. Chem. Lett. 2005, 15, 3307.
doi: 10.1016/j.bmcl.2005.03.082
Tanaka, A.; Terasawa, T.; Hagihara, H.; Sakuma, Y.; Ishibe, N.; Sawada, M.; Takasugi, H.; Tanaka, H. J. Med. Chem. 1998, 41, 2390.
doi: 10.1021/jm9800853
Park, M. S.; Park, H. J.; Park, K. H.; Lee, K. I. Synth. Commun. 2004, 34, 1541.
doi: 10.1081/SCC-120030741
Ma, J. A.; Huang, R. Q.; Feng, L.; Song, J.; Qiu, D. W. Chem. Res. Chin. Univ. 2003, 19, 297.
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).
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7a: R1=CH3, R2=3-CH3; 7b: R1=CH3, R2=4-CH3; 7c: R1=CH3, R2= 2-OCH3; 7d: R1=CH3, R2=4-OCH3; 7e: R1=CH3, R2=4-OCF3; 7f R1=CH3, R2=H; 7g: R1=CH3, R2=2-F; 7h: R1=CH3, R2=3-F; 7i: R1=CH3, R2=3-Cl; 7j: R1=CH3, R2=4-Cl; 7k: R1=CH3, R2=2-Br; 7l: R1=CH3, R2=4-Br; 7m: R1=CH3, R2=4-I; 7n: R1=CH3, R2=2, 3-F2; 7o: R1=CH3, R2=2, 4-Cl2; 7p: R1=4-CH3C6H4, R2=4-CH3; 7q: R1=4-CH3C6H4, R2=4-F