Chinese Journal of Organic Chemistry >
Synthesis and Herbicidal Activity of 2-Cyano-3-(2-substituted phenyoxypyridin-5-yl) Amino Acrylates Containing Substituted Phenoxyl Group
Received date: 2014-08-14
Revised date: 2014-10-10
Online published: 2014-10-16
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 20772067, 21472102).
Two series of 2-cyano-3-(2-substituted phenyoxypyridin-5-yl) amino acrylates containing phenoxyl group were synthesized as photosynthesis II (PSII) electron transport inhibitors using 2-cyano-3-(pyridin-3-yl)aminoarylates as parent compound, in order to investigate how the different phenoxyl group on the two key sites of the parent compound affects their bioactivity. The bioassay results show that both the two series compounds exhibit certain herbicidal activity, and several compounds display > 90% fresh weight inhibit rate for broadleaf weeds (Brassica campestris L) at 1.5 kg/ha after post treatment. View from the structure-activity relationship, it can be primarily speculated that the contribution of different phenoxyl group on the aminopyridinyl of the 3-position on the cyano acrylate to the herbicidal activity is equal to that of their parent groups (aminopyridinyl groups) and their selectivity is much better than that of their parent compounds. The contribution of different phenoxyl group on the ester-site to the herbicidal activity of their parent compound is insufficient.
Wang Xin , Wang Chaoqiang , Fu Cuirong , Zou Xiaomao . Synthesis and Herbicidal Activity of 2-Cyano-3-(2-substituted phenyoxypyridin-5-yl) Amino Acrylates Containing Substituted Phenoxyl Group[J]. Chinese Journal of Organic Chemistry, 2015 , 35(1) : 92 -99 . DOI: 10.6023/cjoc201408017
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