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



王栋, 魏艳, 郝双红   

  1. 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
  • 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   

  1. 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).

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