Synthesis and Herbicidal Activities of 2-Cyanoacrylates with 4-(6-Chloropyridin-3-yl)methoxy-benzylamine Moieties

doi:10.6023/cjoc201412025

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (7): 1484-1492.DOI: 10.6023/cjoc201412025 Previous Articles Next Articles

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含吡啶甲基苯基醚结构的氰基丙烯酸酯类化合物的合成及除草活性研究

吴姗姗^a,b, 苗文科^a,c, 王婷婷^a, 方建新^a

a 南开大学元素有机化学国家重点实验室天津 300071;
b 国家知识产权局专利局专利审查协作江苏中心苏州 215011;
c 南开大学功能高分子材料教育部重点实验室天津 300071

收稿日期:2014-12-15 修回日期:2015-03-14 发布日期:2015-03-19
通讯作者: 苗文科, 方建新 E-mail:miaowenke@mail.nankai.edu.cn
基金资助:
国家自然科学基金(No. 20772068)资助项目.

Synthesis and Herbicidal Activities of 2-Cyanoacrylates with 4-(6-Chloropyridin-3-yl)methoxy-benzylamine Moieties

Wu Shanshan^a,b, Miao Wenke^a,c, Wang Tingting^a, Fang Jianxin^a

a State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071;
b Patent Examination Cooperation JiangSu Center of The Patent Office, Sipo, Suzhou 215011;
c Key Laboratory of Functional Polymer Materials of Ministry of Education, Nankai University, Tianjin 300071

Received:2014-12-15 Revised:2015-03-14 Published:2015-03-19
Supported by:
Project supported by the National Natural Science Foundation of China (No. 20772068).

1. Synthesis and Herbicidal Activities of 2-Cyanoacrylates with 4-(6-Chloropyridin-3-yl)methoxy-benzylamine Moieties.PDF(1823KB)

Abstract

Two series of 2-cyanoacrylates containing 4-(6-chloropyridin-3-yl)methoxy-benzylamine moieties were synthesized as herbicides using 2-cyano-3-(pyridine-3-yl)aminoacrylates as precursor compound. The structures were confirmed by ¹H NMR, ¹³C NMR, Elemental Analysis or High-Resolution Mass spectrometry (HRMS). The herbicidal activity tests showed that most of the target compounds had good inhibition towards dicotyledonous weeds. Compounds 13e and 13g showed 100% herbicidal activity at the dose of 375g/ha against rape, and compound 13e showed 100% herbicidal activity against rape even at the dose of 187.5 g/ha. From the structure-activity relationship study, it can be primarily concluded that both the contributions of the electronic and steric effects of the phenyl group are very important to the herbicidal activity.

Key words: 2-cyanocarylates, 4-(6-chloropyridin-3-yl)methoxy-benzylamine, herbicidal activity, structure-activity relationship

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Wu Shanshan, Miao Wenke, Wang Tingting, Fang Jianxin. Synthesis and Herbicidal Activities of 2-Cyanoacrylates with 4-(6-Chloropyridin-3-yl)methoxy-benzylamine Moieties[J]. Chin. J. Org. Chem., 2015, 35(7): 1484-1492.

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含吡啶甲基苯基醚结构的氰基丙烯酸酯类化合物的合成及除草活性研究

Synthesis and Herbicidal Activities of 2-Cyanoacrylates with 4-(6-Chloropyridin-3-yl)methoxy-benzylamine Moieties

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