Synthesis and Herbicidal Activity of 2-Ethoxyethyl-2-cyano-3-(1-(4- (substitued phenoxy)phenyl)ethylamino) Alkenates

doi:10.6023/cjoc201408012

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (1): 109-120.DOI: 10.6023/cjoc201408012 Previous Articles Next Articles

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2-氰基-3-[1-(4-取代苯氧基苯基)乙胺基]烯酸乙氧乙酯的合成及除草活性

杨晓兵, 毕常芬, 胡方中, 狄红静, 程心心, 李丹, 阚晓丽, 马嘉雪, 邹小毛

南开大学元素有机化学国家重点实验室南开大学元素有机化学研究所天津化学化工协同创新中心天津 300071

收稿日期:2014-08-12 修回日期:2014-10-08 发布日期:2014-10-13
通讯作者: 胡方中 E-mail:fzhu@nankai.edu.cn
基金资助:
国家“十二五”科技支撑计划(No. 2011BAE06B03-12)资助项目.

Synthesis and Herbicidal Activity of 2-Ethoxyethyl-2-cyano-3-(1-(4- (substitued phenoxy)phenyl)ethylamino) Alkenates

Yang Xiaobing, Bi Changfen, Hu Fangzhong, Di Hongjing, Cheng Xinxin, Li Dan, Kan Xiaoli, Ma Jiaxue, Zou Xiaomao

State Key Laboratory and Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071

Received:2014-08-12 Revised:2014-10-08 Published:2014-10-13
Supported by:
Project supported by the National “Twelfth Five-Year” Plan for Science & Technology (No. 2011BAE06B03-12).

1. Synthesis and Herbicidal Activity of 2-Ethoxyethyl-2-cyano-3-(1-(4- (substitued phenoxy)phenyl)ethylamino) Alkenates.PDF(3444KB)

Abstract

Key intermediates, 1-(4-substitutedphenoxyphenyl)ethanamines (9), which were prepared from starting material substituted phenols 4 and p-fluoroacetophenone (5), were condensed with 2-ethoxyethyl 2-cyano-3-ethoxypent-2-enoate (1) or 2-ethoxyethyl-2-cyano-3,3-bis(methylthio)acrylate (2) or 2-ethoxyethyl-3-chloro-2-cyano-4,4,4-trifluorobut-2-enoate (3), giving three series of 2-ethoxyethyl 2-cyano-3-(1-(substitued phenoxyphenyl)ethylamino) alkenates (10, 11 and 12). All of the new compounds have been characterized by ¹H NMR, ¹³C NMR, ¹⁹F NMR, IR and HRMS. The herbicidal activities of the title compounds were tested, which indicated that some of the title compounds showed 100% inhibition against Brassica campestris and Amaranthus retroflexus L. at a dose of 93.75 g/ha.

Key words: 2-cyanoalkenates, phenoxyphenyl ethylamine, synthesis, herbicidal activity

Cite this article

Yang Xiaobing, Bi Changfen, Hu Fangzhong, Di Hongjing, Cheng Xinxin, Li Dan, Kan Xiaoli, Ma Jiaxue, Zou Xiaomao. Synthesis and Herbicidal Activity of 2-Ethoxyethyl-2-cyano-3-(1-(4- (substitued phenoxy)phenyl)ethylamino) Alkenates[J]. Chin. J. Org. Chem., 2015, 35(1): 109-120.

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2-氰基-3-[1-(4-取代苯氧基苯基)乙胺基]烯酸乙氧乙酯的合成及除草活性

Synthesis and Herbicidal Activity of 2-Ethoxyethyl-2-cyano-3-(1-(4- (substitued phenoxy)phenyl)ethylamino) Alkenates

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