新型含取代噁二唑结构的吡唑肟类化合物的合成与生物活性研究
收稿日期: 2018-02-08
修回日期: 2018-03-01
网络出版日期: 2018-03-29
基金资助
南通市科技计划(No.MS22015020)和江苏省大学生创新训练计划(No.201710304048)资助项目.
Synthesis and Biological Activities of Novel Pyrazole Oximes Containing Substituted Oxadiazole Moiety
Received date: 2018-02-08
Revised date: 2018-03-01
Online published: 2018-03-29
Supported by
Project supported by the Science and Technology Project Fund of Nantong City (No. MS22015020) and the Science and Technology Innovation Foundation for the College Students of Jiangsu Province (No. 201710304048).
戴红 , 丁颖 , 杜显超 , 姚炜 , 陈庆文 , 王祥龙 , 仲苏林 , 曹雄飞 , 石玉军 . 新型含取代噁二唑结构的吡唑肟类化合物的合成与生物活性研究[J]. 有机化学, 2018 , 38(7) : 1755 -1762 . DOI: 10.6023/cjoc201802015
In order to find novel pyrazole oximes with good bioactivities, a series of novel pyrazole oxime derivatives containing substituted oxadiazole moiety were designed and synthesized according to the method of active substructure combination. Their structures were confirmed by 1H NMR, 13C NMR and elemental analysis. Preliminary bioassay data indicated that some title compounds showed good insecticidal activities. At the concentration of 500 μg/mL, 9 compounds possessed insecticidal activity against Oriental armyworm with 80%~100%. When the concentration was lowered to 100 μg/mL, 3 compounds still displayed significant insecticidal activity against Oriental armyworm with 70%, 60% and 70%. Additionally, one compound had 60% insecticidal activity against Aphis medicaginis at 500 μg/mL.
Key words: oxadiazole; pyrazole oxime; synthesis; biological activity
[1] Li, Y.; Zhang, H. Q.; Liu, J.; Yang, X. P.; Liu, Z. J. J. Agric. Food Chem. 2006, 54, 3636.
[2] Dai, H.; Zhuang. H. Y.; Shi, L.; Li, G.; Zhang, H. J.; Fang, Y.; Dai, B. J. Chin. J. Org. Chem. 2015, 35, 2399 (in Chinese).
(戴红, 庄辉阳, 施磊, 李刚, 张海军, 方源, 戴宝江, 有机化学, 2015, 35, 2399.)
[3] Dai, H.; Li, H.; Jin. Z. C.; Liu, W. Y.; Xiao, Y.; He, H. B.; Wang, Q. M.; Shi, Y. J. Chin. J. Org. Chem. 2016, 36, 185 (in Chinese).
(戴红, 李宏, 金智超, 刘文永, 肖瑶, 何海兵, 汪清民, 石玉军, 有机化学, 2016, 36, 185.)
[4] Motoba, K.; Nishizawa, H.; Suzuki, T.; Hamaguchi, H.; Uchida, M.; Funayama, S. Pestic. Biochem. Physiol. 2000, 67, 73.
[5] 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.
[6] 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.
[7] Ouyang, G. P.; Chen, Z.; Cai, X. J.; Song, B. A.; Bhadury, P. S.; Yang, S.; Jin, L. H.; Xue, W.; Hu, D. Y.; Zeng, S. Bioorg. Med. Chem. 2008, 16, 9699.
[8] Wang, S. L.; Shi, Y. J.; He, H. B.; Li, Y.; Li, Y.; Dai, H. Chin. Chem. Lett. 2015, 26, 672.
[9] Hamaguchi, H.; Kajihara, O.; Katoh, M. J. Pestic. Sci. 1995, 20, 173.
[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] Dai, H.; Xiao, Y. S.; Li, Z.; Xu, X. Y.; Qian, X. H. Chin. Chem. Lett. 2014, 25, 1014.
[12] Dai, H.; Chen, J.; Li, H.; Dai, B. J.; He, H. B.; Fang, Y.; Shi, Y. J. Molecules 2016, 21, 276.
[13] Huang, Q. C.; Qian, X. H.; Song, G. H.; Cao, S. Pest Manage. Sci. 2003, 59, 933.
[14] 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.
[15] 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.)
[16] Shi, Y. J.; Ye, L. Y.; Zhong, S. L.; Cao, X. F.; Dai, H.; Hong, Y.; Li, C. J.; Shi, J.; Wu, J. M. Chin. J. Org. Chem. 2017, 37, 1844 (in Chinese).
(石玉军, 叶林玉, 仲苏林, 曹雄飞, 戴红, 洪宇, 李春建, 石健, 吴锦明, 有机化学, 2017, 37, 1844.)
[17] Suzuki, J.; Okamura, D.; Gushikawa, T.; Hirai, K.; Ando, T. J. Pestic. Sci. 2011, 36, 392.
[18] Liu, A. C.; Feng, J. L.; He, X. L.; Chen, L.; Zou, X. D. Chin. J. Pestic. 2014, 53, 561 (in Chinese).
(刘安昌, 冯佳丽, 贺晓露, 陈露, 邹晓东, 农药, 2014, 53, 561.)
[19] Li, Y. H.; Zhu, H. J.; Chen, K.; Liu, R.; Khallaf, A.; Zhang, X. N.; Ni, J. P. Org. Biomol. Chem. 2013, 11, 3979.
[20] Liu, Q.; Zhu, R.; Gao, S.; Ma, S. H.; Tang, H. J.; Yang, J. J.; Diao, Y. M.; Wang, H. L.; Zhu, H. J. Pest Manage. Sci. 2017, 73, 917.
[21] Zhao, Q. Q.; Liu, S. H.; Li, Y. H.; Wang, Q. M. J. Agric. Food Chem. 2009, 57, 2849.
[22] Park, M. S.; Park, H. J.; Park, K. H.; Lee, K. I. Synth. Commun. 2004, 34, 1541.
[23] Dai, H.; Ge, S. S.; Li, G.; Chen, J.; Shi, Y. J.; Ye, L. Y.; Ling, Y. Bioorg. Med. Chem. Lett. 2016, 26, 4504.
[24] Dai, H.; Ye, L. Y.; Zhuang, H. Y.; Dai, B. J.; Fang, Y.; Shi, Y. J. Molecules 2015, 20, 21870.
/
| 〈 |
|
〉 |