Synthesis and Herbicidal Activity of Novel N-Allyloxy/Propargyloxy Aryloxyphenoxy Propionamide Derivatives

doi:10.1007/s40242-016-5415-0

Chemical Research in Chinese Universities ›› 2016, Vol. 32 ›› Issue (2): 188-194.doi: 10.1007/s40242-016-5415-0

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Synthesis and Herbicidal Activity of Novel N-Allyloxy/Propargyloxy Aryloxyphenoxy Propionamide Derivatives

LIU Qixing¹, HUANG Mingzhi², LIU Aiping², HU Aixi³, LEI Manxiang², REN Yeguo², HUANG Lu²

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

Received:2015-10-26 Revised:2015-12-30 Online:2016-04-01 Published:2016-01-11
Contact: LIU Aiping, HU Aixi E-mail:llaappliu@sina.cn;axhu@hnu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.21272062), the Startup Foundation of China Three Gorges University(No.KJ2014B084) and the Open Foundation of Hubei Key Laboratory of Tumor Microenvironment and Immunotherapy, China(No.2015KZL09).

Abstract

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.

Key words: Aryloxyphenoxy propionamide, Allyloxy, Propargyloxy, Herbicidal activity, Crop selectivity

LIU Qixing, HUANG Mingzhi, LIU Aiping, HU Aixi, LEI Manxiang, REN Yeguo, HUANG Lu. Synthesis and Herbicidal Activity of Novel N-Allyloxy/Propargyloxy Aryloxyphenoxy Propionamide Derivatives[J]. Chemical Research in Chinese Universities, 2016, 32(2): 188-194.

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Synthesis and Herbicidal Activity of Novel N-Allyloxy/Propargyloxy Aryloxyphenoxy Propionamide Derivatives

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