Synthesis and Herbicidal Activity of Novel Cyanoacrylates Containing Substituted Pyridyl Moiety

doi:10.6023/cjoc201611029

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (3): 739-745.DOI: 10.6023/cjoc201611029 Previous Articles Next Articles

NOTE

新型含取代吡啶结构的氰基丙烯酸酯类化合物的合成与除草活性研究

戴红^a, 陈佳^a, 洪宇^a, 袁斌颖^a, 陈雨蒙^a, 石玉军^a, 马瑞媛^a, 梁志鹏^b, 石健^b

a 南通大学化学化工学院南通 226019;
b 南通大学分析测试中心南通 226019

收稿日期:2016-11-23 修回日期:2016-12-08 发布日期:2016-10-11
通讯作者: 石玉军,E-mail:yjshi2015@163.com;石健,E-mail:gaohbhe2015@aliyun.com E-mail:yjshi2015@163.com;gaohbhe2015@aliyun.com
基金资助:
国家自然科学基金（No.21372135）、江苏省“六大人才高峰”（No.2013-SWYY-013）和江苏省大学生创新训练计划（No.201610304047Z）资助项目.

Synthesis and Herbicidal Activity of Novel Cyanoacrylates Containing Substituted Pyridyl Moiety

Dai Hong^a, Chen Jia^a, Hong Yu^a, Yuan Binying^a, Chen Yumeng^a, Shi Yujun^a, Ma Ruiyuan^a, Liang Zhipeng^b, Shi Jian^b

a College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019;
b Analysis and Testing Center, Nantong University, Nantong 226019

Received:2016-11-23 Revised:2016-12-08 Published:2016-10-11
Contact: 10.6023/cjoc201611029 E-mail:yjshi2015@163.com;gaohbhe2015@aliyun.com
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).

Abstract

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

Cite this article

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]. Chin. J. Org. Chem., 2017, 37(3): 739-745.

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新型含取代吡啶结构的氰基丙烯酸酯类化合物的合成与除草活性研究

Synthesis and Herbicidal Activity of Novel Cyanoacrylates Containing Substituted Pyridyl Moiety

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