新型含取代吡啶环的取代吡唑甲醛肟的合成及生物活性测定
收稿日期: 2015-06-03
修回日期: 2015-06-30
网络出版日期: 2015-07-10
基金资助
国家自然科学基金(Nos. 21202089, 21372135)和南通市科技计划(No. AS2013002)资助项目.
Synthesis and Biological Activities of Novel Substituted Pyrazole Oximes Containing Substituted Pyridine Group
Received date: 2015-06-03
Revised date: 2015-06-30
Online published: 2015-07-10
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21202089, 21372135), and the Science and Technology Project Fund of Nantong City (No. AS2013002).
戴红 , 庄辉阳 , 施磊 , 李刚 , 张海军 , 方源 , 戴宝江 . 新型含取代吡啶环的取代吡唑甲醛肟的合成及生物活性测定[J]. 有机化学, 2015 , 35(11) : 2399 -2404 . DOI: 10.6023/cjoc201506004
In order to explore novel potent pesticide from pyrazole oxime derivatives, a series of new pyrazole oxime ester compounds bearing substituted pyridine moiety were synthesized by the introduction of pyridyl backbone into the molecules of pyrazole oxime. Their structures were confirmed by 1H NMR, 13C NMR and elemental analysis. Preliminary bioassay results showed that some of the title compounds displayed certain insecticidal and acaricidal activities. For example, compound 5i exhibited insecticidal activity against Aphis craccivora with 90% mortality at the concentration of 400 μg/mL.
Key words: substituted pyridine; pyrazole oxime; synthesis; bioactivity
[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] 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.
[4] Hamaguchi, H.; Kajihara, O.; Katoh, M. J. Pestic. Sci. 1995, 20, 173.
[5] Motoba, K.; Nishizawa, H.; Suzuki, T.; Hamaguchi, H.; Uchida, M.; Funayama, S. Pestic. Biochem. Physiol. 2000, 67, 73.
[6] 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.)
[7] 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.
[8] 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.
[9] Dai, H.; Xiao, Y. S.; Li, Z.; Xu, X. Y.; Qian, X. H. Chin. Chem. Lett. 2014, 25, 1014.
[10] 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.
[11] Liu, J. B.; Tao, W. F.; Hu, Y.; Dai, H.; Fang, J. X. Chin. J. Org. Chem. 2006, 26, 1566 (in Chinese). (刘建兵, 陶伟峰, 胡燕, 戴红, 方建新, 有机化学, 2006, 26, 1566.)
[12] Ye, Z. J.; Shi, L. N.; Shao, X. S.; Xu, X. Y.; Xu, Z. P.; Li, Z. J. Agric. Food Chem. 2013, 61, 312.
[13] Lu, S. Y.; Zhuang, Y. Y.; Wu, N. B.; Feng, Y.; Cheng, J. G.; Li, Z.; Chen, J.; Yuan, J.; Xu, X. Y. J. Agric. Food Chem. 2013, 61, 10858.
[14] 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.)
[15] Lahm, G. P.; Selby, T. P.; Freudenberger, J. H.; Stevenson, T. M.; Myers, B. J.; Seburyamo, G.; Simth, B. K.; Flexner, L.; Clark, C. E.; Cordova, D. Bioorg. Med. Chem. Lett. 2005, 15, 4898.
[16] Tian, Z. Z.; Shao, X. S.; Li, Z.; Qian, X. H.; Huang, Q. C. J. Agric. Food Chem. 2007, 55, 2288.
[17] Lu, S. Y.; Shao, X. S.; Li, Z.; Xu, Z. P.; Zhao, S. S.; Wu, Y. L.; Xu, X. Y. J. Agric. Food Chem. 2012, 60, 322.
[18] 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.
[19] Xu, R. B.; Xia, R.; Luo, M.; Xu, X. Y.; Cheng, J. G.; Shao, X. S.; Li, Z. J. Agric. Food Chem. 2014, 62, 381.
[20] Mu, C.-W.; Qin, Z.-H. Modern Agrochem. 2003, 2, 1 (in Chinese). (慕长伟, 覃兆海, 现代农药, 2003, 2, 1.)
[21] 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.)
[22] 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.)
[23] Cativiela, C.; Serrano, J. L.; Zurbano, M. M. J. Org. Chem. 1995, 60, 3074. Park, M. S.; Park, H. J.; Park, K. H.; Lee, K. I. Synth. Commun. 2004, 34, 1541.
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