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Synthesis and Herbicidal Activity of Novel N-Allyloxy/Propargyloxy Aryloxyphenoxy Propionamide Derivatives
Authors:LIU Qixing  HUANG Mingzhi  LIU Aiping  HU Aixi  LEI Manxiang  REN Yeguo  HUANG Lu
Affiliation:1. College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, P. R. China;
2. National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007, P. R. China;
3. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China
Abstract:A series of novel N-allyloxy/propargyloxy aryloxyphenoxy propionamide compounds was designed and prepared. The structures of the synthesized compounds were confirmed by means of 1H NMR, 13C NMR, LC-MS, elemental analysis and IR. The bioassay results indicate that when against Digitaria sanguinalis and Echinochloa crus-galli, (R)-N-(propargyloxy)-2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanamide(1m)(IC50=6.8 and 6.5 g/hm2, respectively) and (R)-N-(allyloxy)-2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanamide(1r)(IC50=7.4 and 6.0 g/hm2, respectively) are much more effective than commercial aryloxyphenoxypropionic ester herbicide clodinafop-propargyl(IC50=46.5 and 14.6 g/hm2, respectively). The results of crop selectivity show that compounds 1m and 1r are safe to soybean, rape and cotton and can be used as herbicides for soybean, rape and cotton crop.
Keywords:Aryloxyphenoxy propionamide  Allyloxy  Propargyloxy  Herbicidal activity  Crop selectivity  
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