Synthesis and Study on Insecticidal Activity of New Heterocyclic Chalcone Derivatives

doi:10.6023/cjoc201712027

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (7): 1763-1771.DOI: 10.6023/cjoc201712027 Previous Articles Next Articles

Articles

新型杂环查尔酮衍生物的合成及其杀虫活性研究

严映坤^a, 徐侨^b, 高扬^a, 刘辉^a, 唐孝荣^a

a 西华大学理学院成都 610039;
b 西华大学食品与生物工程学院成都 610039

收稿日期:2017-12-19 修回日期:2018-01-31 发布日期:2018-03-16
通讯作者: 唐孝荣 E-mail:1874790546@qq.com

Synthesis and Study on Insecticidal Activity of New Heterocyclic Chalcone Derivatives

Yan Yingkun^a, Xu Qiao^b, Gao Yang^a, Liu Hui^a, Tang Xiaorong^a

a School of Science, Xinhua University, Chengdu 610039;
b School of Food and Bioengineering, Xihua University, Chengdu 610039

Received:2017-12-19 Revised:2018-01-31 Published:2018-03-16
Contact: 10.6023/cjoc201712027 E-mail:1874790546@qq.com

1. Synthesis and Study on Insecticidal Activity of New Heterocyclic Chalcone Derivatives.PDF(2594KB)

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.

Key words: heterocyclic chalcone, insecticidal activity, Aphis craccivora, Pieris rapae

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]. Chin. J. Org. Chem., 2018, 38(7): 1763-1771.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

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.)

新型杂环查尔酮衍生物的合成及其杀虫活性研究

Synthesis and Study on Insecticidal Activity of New Heterocyclic Chalcone Derivatives

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Min Liu, Dongyan Yang, Yumei Xiao, Wangcang Su, Fenghai Zhao, Qin Zhaohai .. Synthesis and Bioactivities of 5-Nitroimino-[1,4-2H]-1,2,4-triazolines as Olefin-Imidacloprid Mimics [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2790-2799.
[2]	Zichan Zhang, Yang Sun, Sheng Hua, Baolin Xu, Min Zhang, Qin Zhao, Dandan Zheng, Yang Wang, Jianfeng Ju, Yujun Shi, Hong Dai. Synthesis and Insecticidal Activity of Novel Pyrazole Amides Containing an Isoxazole Moiety [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1435-1443.
[3]	Lei Wang, Shujing Yu, Na Yang, Baolei Wang. Studies on the Synthesis and Biological Activities of Novel Dihydroquinazolinone-Containing Caffeine Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 299-307.
[4]	Wenjuan Li, Rui Zhang, Zhihua Cai, Xiaoqiang Han, Lin He, Bin Dai. Constrution and Insecticidal Activities of Trifluoromethylated Benzocyclicsulfoximine Derivatives by [3+2] Cycloaddition Reaction of Beznyne [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2832-2839.
[5]	Shu Chen, Yingying Shao, Xinhao Fu, Qingwu Chen, Xiaohua Du, Chengxia Tan. Design, Synthesis and Insecticidal Activities of Pyridyl Thiazole Diamide Compounds [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3870-3879.
[6]	Ali Dai, Renfeng Zhang, Chuanhui Li, Lijiao Yu, Ya Wang, Jian Wu. Synthesis and Biological Activity of N-Cyano Sulfonimide Derivatives Bearing Trifluoromethyl Pyridinamide [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3633-3642.
[7]	Feng He, Shengxin Guo, Ali Dai, Renfeng Zhang, Jian Wu. Synthesis, Characterization, and Biological Activity of Novel Amide Derivatives Containing Trifluoromethylpyridine Moieties [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3303-3311.
[8]	Yangyi Yao, Chaoli Ren, Li Chen, Liangkun Zhong, Tianming Xu, Chengxia Tan. Synthesis and Insecticidal Activity of 3-Ethyl Sulfone Pyridine Substituted Aryl Triazole Compounds [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2055-2062.
[9]	Hang Liu, Shuyun Zhang, Huan Li, Yan Zhang, Zhengming Li, Baolei Wang. Synthesis and Biological Activities of Novel 8-((3,4,4-Trifluorobut-3-en-1-yl)thio)-substituted Methylxanthines and Their Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2091-2098.
[10]	Weibin Xie, Huangong Li, Xiangde Meng, Zhengming Li, Sha Zhou. Design, Synthesis and Biological Activity Study of Novel N-Phenylpyrazole Anthranilic Diamides Containing Heptafluoroisopropyl Moieties [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1722-1727.
[11]	Shuyun Zhang, Hang Liu, Lei Wang, Zhengming Li, Baolei Wang. Studies on the Synthesis, Structural Characterization and Biological Activities of Novel Caffeine Derivatives Containing Substituted-Piperazine Moiety [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 4075-4082.
[12]	Zhang Jingpeng, Yang Zhaokai, Qin Yaoguo, Yang Xinling. Design, Synthesis and Biological Activity of (E)-β-Farnesene Analogues Containing 1,2,3-Thiadiazole [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2971-2979.
[13]	Zhao Yu, Liu Xinlei, Li Yihao, Xu Leichuan, Su Yanhao, Jiang Jiazhen, Wang Ming'an. Synthesis and Unexpected Insecticidal Activity of (E)-3-(1-Imino-ethyl)-5,5-disubstituted-4-(methylamino)furan-2(5H)-one [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2547-2554.
[14]	Liang Kai, Zhou Qian, Xun Xiao, Ni Yadan, Li Jinfeng, Shi Yujun, Zhou Huanyu, Wu Xinxing, Shi Jian, Gao Lei, Dai Hong. Synthesis and Insecticidal Activities of Novel Pyrazole Amide Derivatives Containing a Thiazole Unit [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1665-1672.
[15]	Zhang Yan, Shang Junfeng, Li Huan, Liu Hang, Song Haibin, Wang Baolei, Li Zhengming. Synthesis and Biological Activities of Novel N-(2-(5-(3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-1,3,4-oxadiazol-2-yl)-4-chloro-6-methylphenyl) Amides [J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 787-793.