研究简报

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

  • 戴红 ,
  • 庄辉阳 ,
  • 施磊 ,
  • 李刚 ,
  • 张海军 ,
  • 方源 ,
  • 戴宝江
展开
  • a 南通大学化学化工学院 南通 226019;
    b 南通南沈植保科技开发有限公司 南通 226017;
    c 南通职业大学化学与生物工程学院 南通 226007

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

  • Dai Hong ,
  • Zhuang Huiyang ,
  • Shi Lei ,
  • Li Gang ,
  • Zhang Haijun ,
  • Fang Yuan ,
  • Dai Baojiang
Expand
  • a College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019;
    b Nantong Nanshen Plant Protection Science and Technology Development Co. Ltd, Nantong 226017;
    c School of Chemical and Biological Engineering, Nantong Vocational University, Nantong 226007

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).

摘要

为了从吡唑肟类化合物中寻找新的活性物质, 利用活性亚结构拼接原理, 将取代吡啶骨架引入到吡唑肟分子结构中, 制备了一系列未见文献报道的新型含取代吡啶环结构的取代吡唑甲醛肟化合物. 通过核磁氢谱、碳谱和元素分析确证了新化合物的结构. 初步的生物活性测试结果显示, 某些标题化合物表现出一定的杀虫与杀螨活性. 其中化合物5i在浓度为400 μg/mL时对蚕豆蚜的杀死率达到90%.

本文引用格式

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

Abstract

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.

参考文献

[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.

文章导航

/