Synthesis and herbicidal activity of novel N-allyloxy/propargyloxy aryloxyphenoxy propionamide derivatives

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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