Chinese Journal of Organic Chemistry >
Synthesis and Herbicidal Activity of Novel Cyanoacrylates Containing Substituted Pyridyl Moiety
Received date: 2016-11-23
Revised date: 2016-12-08
Online published: 2016-10-11
Supported by
Project supported by the National Natural Science Foundation of China (No. 21372135), the Research Foundation of the Six People Peak of Jiangsu Province (No. 2013-SWYY-013) and the Science and Technology Innovation Foundation for the College Students of Jiangsu Province (No. 201610304047Z).
In order to find new cyanoacrylate lead compounds, a series of novel cyanoacrylates containing substituted pyridyl moiety were prepared by the method of active substructure combination. The structures of the target compounds were confirmed by 1H NMR, 13C NMR and elemental analyses. Preliminary bioassay data displayed that in postemergence treatment 2-cyano-3-methylthio-3-[4-(5-trifluoromethylpyridyl-2-amino)]benzylamino(2-methoxy)ethyl ester (7l) had 95% herbicidal activity against Brassica juncea at 1500 g/ha and 2-cyano-3-methylthio-3-[4-(5-trifluoromethylpyridyl-2-amino)]benzylamino-[2-(2,4-difluorophenoxy)]ethyl ester (7e), 7l and 2-cyano-3-methylthio-3-[4-(5-trifluoromethylpyridyl-2-amino)]benzylamino-(2-ethoxy)ethyl ester (7m) showed 80%, 80% and 100% herbicidal activity against Stellaria media, respectively. Additionally, 2-cyano-3-methylthio-3-[4-(5-trifluoromethylpyridyl-2-amino)]benzylamino[2-(2-fluorophenoxy)]ethyl ester (7b), 7l and 7m all exhibited 100% herbicidal activity against Chenopodium serotinum L. at 1500 g/ha.
Key words： pyridine; cyanoacrylate; synthesis; herbicidal activity
Dai Hong , Chen Jia , Hong Yu , Yuan Binying , Chen Yumeng , Shi Yujun , Ma Ruiyuan , Liang Zhipeng , Shi Jian . Synthesis and Herbicidal Activity of Novel Cyanoacrylates Containing Substituted Pyridyl Moiety[J]. Chinese Journal of Organic Chemistry, 2017 , 37(3) : 739 -745 . DOI: 10.6023/cjoc201611029
[1] Liu, X.; Huang, R. Q.; Cheng, M. R.; Zhao, Y. G.; Li, Z. G. Chem. J. Chin. Univ. 1999, 20, 1404 (in Chinese). (刘昕, 黄润秋, 程慕如, 赵毅刚, 李在国, 高等学校化学学报, 1999, 20, 1404.)
[2] Zou, X. M.; Yu, L. M.; Gao, Y.; Shi, H. L.; Fei, J.; Liu, B.; Li, H. F.; Hu, F. Z.; Yang, H. Z. Chin. J. Org. Chem. 2006, 26, 337 (in Chinese). (邹小毛, 郁丽敏, 高颍, 施欢乐, 裴江, 刘斌, 李慧芬, 胡方中, 杨华铮, 有机化学, 2006, 26, 337.)
[3] Zhang, H.; Li, X. Y.; Hu, D. Y.; Yang, S.; Fan, H. T.; Wei, X.; Song, B. A. Chin. J. Org. Chem. 2011, 31, 1419 (in Chinese). (章浩, 李向阳, 胡德禹, 杨松, 范会涛, 宋宝安, 有机化学, 2011, 31, 1419.)
[4] Zhong, S. H.; Wang, C. F.; Song, Q. X.; Fan, M. L.; Liu, B. Y.; Wei, D. M.; Liu, J. B. Chin. J. Org. Chem. 2014, 34, 2324 (in Chinese). (钟世华, 王春凤, 宋青霞, 范明亮, 刘兵玉, 危冬梅, 刘建兵, 有机化学, 2014, 34, 2324.)
[5] Wu, S. S.; Miao, W. K.; Wang, T. T.; Fang, J. X. Chin. J. Org. Chem. 2015, 35, 1484 (in Chinese). (吴珊珊, 苗文科, 王婷婷, 方建新, 有机化学, 2015, 35, 1484.)
[6] Sun, H. K.; Wang, Q. M.; Huang, R. Q.; Li, H.; Li, Y. H. J. Organomet. Chem. 2002, 655, 182.
[7] Song, B. A.; Zhang, H. P.; Wang, H.; Yang, S.; Jin, L. H.; Hu, D. Y.; Pang, L. L.; Xue, W. J. Agric. Food Chem. 2005, 53, 7886.
[8] Liu, Y. X.; Cao, B. L.; Li, Y. H.; Song, H. B.; Huang, R. Q.; Wang, Q. M. J. Agric. Food Chem. 2007, 55, 3011.
[9] Zhao, Q. Q.; Liu, S. H.; Li, Y. H.; Wang, Q. M. J. Agric. Food Chem. 2009, 57, 2849.
[10] 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.
[11] 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.)
[12] 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.)
[13] 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.)
[14] 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.)
[15] 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.)
[16] 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.
[17] Tian, Z. Z.; Shao, X. S.; Li, Z.; Qian, X. H.; Huang, Q. C. J. Agric. Food Chem. 2007, 55, 2288.
[18] 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.
[19] 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.
[20] Wang, Q. M.; Sun, H. K.; Cao, H. Y.; Cheng, M. R.; Huang, R. Q. J. Agric. Food Chem. 2003, 51, 5030.
[21] Shi, Y. J.; Li, Y.; Fang, Y.; Chen, J.; Ye, L. Y.; Ge, S. S.; Dai, H. Chin. J. Org. Chem. 2016, 36, 2472 (in Chinese).(石玉军, 李阳, 方源, 陈佳, 叶林玉, 葛书山, 戴红, 有机化学, 2016, 36, 2472.)
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