Chinese Journal of Organic Chemistry >
Synthesis and Herbicidal Activity of 2-Ethoxyethyl-2-cyano-3-(1-(4- (substitued phenoxy)phenyl)ethylamino) Alkenates
Received date: 2014-08-12
Revised date: 2014-10-08
Online published: 2014-10-13
Supported by
Project supported by the National “Twelfth Five-Year” Plan for Science & Technology (No. 2011BAE06B03-12).
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
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]. Chinese Journal of Organic Chemistry, 2015 , 35(1) : 109 -120 . DOI: 10.6023/cjoc201408012
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