研究简报

新型含氮杂环结构的1,1-二氯丙烯类化合物的合成及其生物活性

  • 戴红 ,
  • 葛书山 ,
  • 戴宝江 ,
  • 李钰 ,
  • 施磊 ,
  • 李阳 ,
  • 方源 ,
  • 石玉军
展开
  • a 南通大学化学化工学院 南通 226019;
    b 南通职业大学化学与生物工程学院 南通 226007

收稿日期: 2015-08-14

  修回日期: 2015-09-23

  网络出版日期: 2015-10-08

基金资助

国家自然科学基金(Nos. 21202089, 21372135)和南通市科技计划(Nos. AS2013002, AS2014011)资助项目.

Synthesis and Biological Activity of Novel 1,1-Dichloropropene Derivatives Containing N-Heterocycles

  • Dai Hong ,
  • Ge Shushan ,
  • Dai Baojiang ,
  • Li Yu ,
  • Shi Lei ,
  • Li Yang ,
  • Fang Yuan ,
  • Shi Yujun
Expand
  • a College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019;
    b School of Chemical and Biological Engineering, Nantong Vocational University, Nantong 226007

Received date: 2015-08-14

  Revised date: 2015-09-23

  Online published: 2015-10-08

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 (Nos. AS2013002, AS2014011).

摘要

为了从1,1-二氯丙烯类化合物中寻找新的活性物质, 本文采用活性基团拼接方法, 制备了一系列未见文献报道的新型含氮杂环结构的1,1-二氯丙烯衍生物. 通过1H NMR, 13C NMR和元素分析等手段对目标化合物的结构进行了验证.初步的生物活性测试结果显示, 在测试浓度为500 μg/mL时大多数目标化合物表现出良好的杀粘虫活性, 其中化合物6a, 6b, 6c, 6d, 6e, 6f, 6i, 6l, 6m6o对粘虫的杀死率均为100%. 此外, 部分目标物还表现出一定的杀蚜虫活性.

本文引用格式

戴红 , 葛书山 , 戴宝江 , 李钰 , 施磊 , 李阳 , 方源 , 石玉军 . 新型含氮杂环结构的1,1-二氯丙烯类化合物的合成及其生物活性[J]. 有机化学, 2015 , 35(12) : 2610 -2616 . DOI: 10.6023/cjoc201508015

Abstract

In search of novel 1,1-dichloropropene compounds with potent bioactivities, a series of novel 1,1-dichloropropene derivatives containing N-heterocycles were synthesized by the strategy of active substructure combination. The structures of the target compounds were confirmed by 1H NMR, 13C NMR and elemental analysis. Preliminary bioassay indicated that most of the title compounds showed good larvicidal activity against Oriental armyworm at the concentration of 500 μg/mL. For example, the inhibition rates against Oriental armyworm of compounds 6a, 6b, 6c, 6d, 6e, 6f, 6i, 6l, 6m and 6o were all 100%. Besides, some target compounds displayed certain insecticidal activity against Aphis craccivora at the concentration of 500 μg/mL.

参考文献

[1] Sakamoto, N.; Saito, S.; Hirose, T.; Suzuki, M.; Matsuo, S.; Izumi, K,; Nagatomi, T.; Ikegami, H.; Umeda, K.; Tsushima, K.; Matsuo, N. Pest Manage. Sci. 2003, 60, 25.
[2] Saito, S.; Isayama, S.; Sakamoto, N.; Umeda, K. J. Pestic. Sci. 2004, 29, 372.
[3] Isayama, S.; Saito, S.; Kuroda, K.; Umeda, K.; Kasamatsu, K. Arch. Insect Biochem. Physiol. 2005, 58, 226.
[4] Saito, S.; Ysoshioka, T.; Umeda, K. J. Pestic. Sci. 2006, 31, 335.
[5] Tian, H. K.; Shi, F. X.; Liu, T.; Ni, J. P.; Ma, H. J.; Yang, C. L. Chin. J. Pestic. Sci. 2009, 11, 421 (in Chinese). (田辉凯, 时凤霞, 刘婷, 倪珏萍, 马海军, 杨春龙, 农药学学报, 2009, 11, 421.)
[6] Wu, T. W.; Ma, H. J.; Tian, H. K.; Ni, J. P.; Yun, Z. Chin. J. Org. Chem. 2010, 30, 713 (in Chinese). (吴同文, 马海军, 田辉凯, 倪珏萍, 云志, 有机化学, 2010, 30, 713.)
[7] Feng, M. L.; Li, Y. F.; Zhu, H. J.; Ni, J. P.; Xi, B. B.; Zhao, L. Pest Manage. Sci. 2012, 68, 986.
[8] Li, J.; Wang, Z. Y.; Wu, Q. Y.; Yang, G. F. Pest Manage. Sci. 2015, 71, 694.
[9] Li, M.; Liu, C. L.; Zhang, J.; Wu, Q.; Hao, S. L.; Song, Y. Q. Pest Manage. Sci. 2013, 69, 635.
[10] Guan, A. Y.; Qin, Y. K.; Wang, J. F.; Li, B. J. Fluorine Chem. 2013, 156, 120.
[11] Zhang, A. G.; Kayser, H.; Maienfisch, P.; Casida, J. E. J. Neurochem. 2000, 75, 1294.
[12] Yokota, T.; Mikata, K.; Nagasaki, H.; Ohta, K. J. Agric. Food Chem. 2003, 51, 7066.
[13] Zhang, G. S.; Hou, G. X. Pestic. Sci. Admin. 2004, 25, 22 (in Chinese). (张国生, 侯广新, 农药科学与管理, 2004, 25, 22.)
[14] Kagabu, S.; Ishihara, R.; Hieda, Y.; Nishimura, K.; Naruse, Y. J. Agric. Food Chem. 2007, 55, 812.
[15] Shao, X. S.; Tian, Z. Z.; Li, Z.; Xu, X. Y.; Huang, Q. C.; Qian, X. H. Chin. J. Pestic. Sci. 2008, 10, 117 (in Chinese). (邵旭升, 田忠贞, 李忠, 徐晓勇, 黄青春, 钱旭红, 农药学学报, 2008, 10, 117.)
[16] Khalema, T. D. L.; Shi, D. Q. Chin. J. Org. Chem. 2010, 30, 1925 (in Chinese). (Khalema, Thandiwe D. L., 石德清, 有机化学, 2010, 30, 1925.)
[17] 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.)
[18] Maienfisch, P. L.; Huerlimann, H.; Rindlisbacher, A.; Gsell, L.; Dettwiler, H.; Haettenschwiler, J.; Sieger, E.; Walti, M. Pest Manage. Sci. 2001, 57, 165.
[19] Dai, B. J. World Pestic. 2005, 27, 46 (in Chinese). (戴宝江, 世界农药, 2005, 27, 46.)
[20] Li, Q.; Yu, H. B.; Guan, A. Y.; Liang, S. J.; Song, Y. Q.; Li, B. Chin. J. Org. Chem. 2012, 32, 1736 (in Chinese). (李琴, 于海波, 关爱莹, 梁松军, 宋玉泉, 李斌, 有机化学, 2012, 32, 1736.)
[21] Kim, H.. J.; Liu, S. Z.; Keum, Y. S.; Li, Q. X. J. Agric. Food Chem. 2003, 51, 1823.

文章导航

/