Synthesis and Herbicidal Activity of N-Acyl-N-(m-fluoro-benzyl)-6-amino-coumarin

doi:10.6023/cjoc201504008

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (8): 1691-1699.DOI: 10.6023/cjoc201504008 Previous Articles Next Articles

ARTICLE

N-酰基-N-间氟苄基-6-氨基香豆素的合成及除草活性

王栋, 魏艳, 郝双红

青岛农业大学化学与药学院山东省农业仿生应用工程技术研究中心青岛 266109

收稿日期:2015-04-07 修回日期:2015-04-22 发布日期:2015-04-27
通讯作者: 郝双红 E-mail:doublered74@sina.com
基金资助:
国家自然科学基金(No. 31471808)、青岛市科技计划基础研究(No. 12-1-4-5-(9)-jch)资助项目.

Synthesis and Herbicidal Activity of N-Acyl-N-(m-fluoro-benzyl)-6-amino-coumarin

Wang Dong, Wei Yan, Hao Shuanghong

College of Chemistry & Pharmacy, Research Center of Agro-bionic Engineering & Technology of Shandong Province, Qingdao Agricultural University, Qingdao 266109

Received:2015-04-07 Revised:2015-04-22 Published:2015-04-27
Supported by:
Project supported by the National Natural Science Foundation of China (No. 31471808) and the Science and Technology Basic Research Project of Qingdao City (No. 12-1-4-5-(9)-jch).

1. Synthesis and Herbicidal Activity of N-Acyl-N-(m-fluoro-benzyl)-6-amino-coumarin.PDF(1802KB)

Abstract

Based on the structure of lead compound N-(m-fluoro-benzyl)-6-amino-coumarin, a series of novel N-acyl-N-(m-fluoro-benzyl)-6-amino-coumarins were designed and synthesized through the principle of bioactive substructure combination. Their structures were characterized by ¹H NMR, ESI-MS and elemental analysis. N-trifluoroacetyl substituted compound d5 was further confirmed by X-ray single crystal diffraction. The herbicidal activities of synthesized compounds were evaluated as well. The results indicated that compounds substituted respectively by N-chloracetyl, N-bromoacetyl, N-trifluoroacetyl and N-(2,4-dichlorophenoxyacetyl) compounds d2, d3, d5 and d17 exhibited marked inhibition against the roots and stems of Amaranthus retroflexus with inhibitory rates above 75% at 100 mg/L, more active than acetochlor EC. In post-emergence treatment experiment, compounds d3 and d17 substituted respectively by N-bromoacetyl and N-(2,4-dichlorophenoxyacetyl) showed more than 76% inhibition against A. retroflexus and other dicotyledons at 1500 g/ha in greenhouse. Compound d17 is safe to monocotyledonous crops wheat, corn and rice at 1500 g a.i./hm².

Key words: N-acyl-N-(m-fluoro-benzyl)-6-amino coumarin derivatives, synthesis, herbicidal activity, crop safety

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Wang Dong, Wei Yan, Hao Shuanghong. Synthesis and Herbicidal Activity of N-Acyl-N-(m-fluoro-benzyl)-6-amino-coumarin[J]. Chin. J. Org. Chem., 2015, 35(8): 1691-1699.

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N-酰基-N-间氟苄基-6-氨基香豆素的合成及除草活性

Synthesis and Herbicidal Activity of N-Acyl-N-(m-fluoro-benzyl)-6-amino-coumarin

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