Synthesis and Herbicidal Activity of 2-Cyano-3-(2-substituted phenyoxypyridin-5-yl) Amino Acrylates Containing Substituted Phenoxyl Group

doi:10.6023/cjoc201408017

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (1): 92-99.DOI: 10.6023/cjoc201408017 Previous Articles Next Articles

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新型含取代苯氧基的2-氰基-3-(2-取代吡啶-5-基)氨基丙烯酸酯类化合物的合成及除草活性

王鑫, 王朝强, 傅翠蓉, 邹小毛

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元素有机化学国家重点实验室天津 300071

收稿日期:2014-08-14 修回日期:2014-10-10 发布日期:2014-10-16
通讯作者: 邹小毛 E-mail:xmzou@nankai.edu.cn
基金资助:
国家自然科学基金(Nos. 20772067, 21472102)资助项目.

Synthesis and Herbicidal Activity of 2-Cyano-3-(2-substituted phenyoxypyridin-5-yl) Amino Acrylates Containing Substituted Phenoxyl Group

Wang Xin, Wang Chaoqiang, Fu Cuirong, Zou Xiaomao

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

Received:2014-08-14 Revised:2014-10-10 Published:2014-10-16
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 20772067, 21472102).

1. Synthesis and Herbicidal Activity of 2-Cyano-3-(2-substituted phenyoxypyridin-5-yl) Amino Acrylates Containing Substituted Phenoxyl Group.PDF(847KB)

Abstract

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.

Key words: inhibitors of PS II electron transport, substituted phenoxypyridinyl, 2-cyanoacrylates, herbicidal activity, structure-activity relationship

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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]. Chin. J. Org. Chem., 2015, 35(1): 92-99.

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新型含取代苯氧基的2-氰基-3-(2-取代吡啶-5-基)氨基丙烯酸酯类化合物的合成及除草活性

Synthesis and Herbicidal Activity of 2-Cyano-3-(2-substituted phenyoxypyridin-5-yl) Amino Acrylates Containing Substituted Phenoxyl Group

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