Articles

Synthesis and Study on Insecticidal Activity of New Heterocyclic Chalcone Derivatives

  • Yan Yingkun ,
  • Xu Qiao ,
  • Gao Yang ,
  • Liu Hui ,
  • Tang Xiaorong
Expand
  • a School of Science, Xinhua University, Chengdu 610039;
    b School of Food and Bioengineering, Xihua University, Chengdu 610039

Received date: 2017-12-19

  Revised date: 2018-01-31

  Online published: 2018-03-16

Abstract

Twenty one new heterocyclic chalcone derivatives were synthesized by the Claisen-Schmidt condensation and ammonolysis of acyl chloride using heterocyclic aldehyde and amino substituted acetophenone as well as acyl chloride as raw materials. The laboratorial bioassay of the insecticidal activity of the synthesized compounds was performed using Aphis craccivora and Pieris rapae as targets. The results showed that most of them had significant insecticidal activity against the two pests. Among them, the median lethal concentration (LC50) of compound 2l was 1.6 μg/mL against Aphis craccivora, whose insecticidal efficacy was superior to imidacloprid with LC50 of 1.8 μg/mL. The insecticidal efficacy of 1b, 1f, 2j and 2n was also close to imidacloprid against Aphis craccivora. The LC50 values of compounds 1f and 2m against Aphis craccivora and Pieris rapae were 6.6 μg/mL and 8.5 μg/mL, respectively and their insecticidal activity exceeded β-cypermethrin, whose LC50 was 9.2 μg/mL.

Cite this article

Yan Yingkun , Xu Qiao , Gao Yang , Liu Hui , Tang Xiaorong . Synthesis and Study on Insecticidal Activity of New Heterocyclic Chalcone Derivatives[J]. Chinese Journal of Organic Chemistry, 2018 , 38(7) : 1763 -1771 . DOI: 10.6023/cjoc201712027

References

[1] Ruan, L. L.; Fan, R. J.; Liu, X. H.; Chen, J.; Weng, J. Q. Chin. J. Org. Chem. 2015, 35, 1166 (in Chinese).
(阮铃莉, 范人杰, 刘幸海, 陈杰, 翁建全, 有机化学, 2015, 35, 1166.)
[2] Anuradha, V.; Pullela, V.; Srinivas, R.; Ranga, R. K.; Manjulatha, M. G.; Purohit, J.; Adhusudana, R. Bioorg. Med. Chem. 2006, 14, 6820.
[3] Formagio, A. S. N.; Tonin, L. T D.; Foglio, M. A.; Madjarof, C.; Carvalho. J. E. D.; Costa, W. F. D.; Cardoso, F. P.; Sarragiotto, M. H. Bioorg. Med. Chem. 2008, 16, 9660.
[4] Xe, F.; Liu, T. T.; Yang, G.; Yuan, J.; Kong, X. L.; Xu, T. M.; Tan, C. X. Chin. J. Org. Chem. 2013, 33, 2596 (in Chinese).
(谢峰, 刘婷婷, 杨果, 袁静, 孔小林, 许天明, 谭成侠, 有机化学, 2013, 33, 2596.)
[5] Babasaheb, P.; Bandgar, S. S.; Gawande, J. Bioorg. Med. Chem. 2010, 18, 2060.
[6] Rupak, K. K.; Sarma, N. R.; Jadab, C. S. J. Steroids 2013, 78, 321.
[7] Yin, B. T.; Yan, C. Y.; Peng, X. M.; Zhang, S. L.; Rasheed, S.; Geng, R. X.; Zhou, C. H. Eur. J. Med. Chem. 2014, 71, 148.
[8] Tavares, C.; Susana, J.; Alves, T. A.; Juliana C. G.; Elaine, S. F.; Cisalpino, P. S.; Adailton, J.; Giovanni, F.; Caramori, R. P.; Hugo, T. S.; Mara, E. F.; Braibante, M. G. J. Eur. J. Med. Chem. 2011, 46, 4448.
[9] Hsieh, C. T.; Hsieh, T. J.; Mohamed, E. S.; Chuang, D. W.; Tsai, Y. H.; Yen, C. T.; Wu, S. F.; Wu, Y. C.; Chang, F. R. Bioorg. Med. Chem. Lett. 2012, 22, 3912.
[10] Dai, H.; Liu, J. B.; Miao, W. K.; Wu, S. S.; Zhang, X.; Wang, T. T.; Fang, J. X. Chin. J. Org. Chem. 2011, 31, 1943 (in Chinese).
(戴红, 刘建兵, 苗文科, 吴珊珊, 张欣, 王婷婷, 方建新, 有机化学, 2011, 31, 1943.)
[11] Shang, E. C.; Liu, C. L.; Du, Y. J. Chem. Ind. Eng. Prog. 1996, 5, 11 (in Chinese).
(尚尔才, 刘长令, 杜英娟, 化工进展, 1996, 5, 11.)
[12] Yang, J. C.; Dai, R. H.; Liu, Y. P.; Wu, Q.; Liu, C. L. Chin. J. Pestic. 2011, 50, 625 (in Chinese).
(杨吉春, 戴荣华, 刘允萍, 吴娇, 刘长令, 农药, 2011, 50, 625.)
[13] Wang, Z. J.; Liu, B.; Li, Y. H.; Zhao, W. G. Chin. J. Org. Chem. 2011, 31, 317 (in Chinese).
(王振军, 刘斌, 李永红, 赵卫光, 有机化学, 2011, 31, 317.)
[14] Wang, H. S.; Zhao, W. X. Chin. J. Org. Chem. 2013, 33, 1822 (in Chinese).
(王宏社, 赵卫星, 有机化学, 2013, 33, 1822.)
[15] Sheng, G Z.; Zhang, W. Chin. J. Org. Chem. 2013, 33, 2271 (in Chinese).
(盛国柱, 张炜, 有机化学, 2013, 33, 2271.)
[16] Leroux P. J. J. Pestic. Sci. 1996, 47, 191.
[17] Smiley, R. W.; Wilkins, D. E. Klepper, E. L. Plant Dis. 1990, 74, 782.
[18] Kataria, H. R.; Verma, P. R.; Racow, G. J. Ann. Appl. Biol. 1993, 123:247.
[19] Nakagawa, Y.; Henrich, V. Bioorg. Med. Chem. Lett. 2009, 276, 6128.
[20] Xu, Z. H.; Li, J. K. Jiangsu Agric. Sci. 2015, 45, 5 (in Chinese).
(徐志红, 李俊凯, 江苏农业科学, 2015, 45, 5.)
[21] Wang, J. B.; Tan, F. R.; Wang, L. G. Acta Agric. Shanghai 2009, 25, 131(in Chinese).
(王金斌, 谭芙蓉, 王利刚, 上海农业学报. 2009, 25, 131.)
[22] Catto, A.; Motta, G.; Tajana, A.; Cazzulani, P.; Nardi, D.; Leonardi, A. J. Med. Chem. 1987, 30, 16.
[23] Karaman, I.; Gezegen, H.; Guerdere, M. B.; Dingil, A.; Ceylan, M. Chem. Biodiversity 2010, 2, 400.
[24] Zhang, Z. B. Toxicity Determination of Insecticides, Science Press, Beijing, 1988.
(张宗炳, 杀虫药剂的毒力测定, 科学出版社, 北京, 1988 (in Chinese.)

Outlines

/