Synthesis and herbicidal activities of 2-methylpropan-2-aminium O-methyl 1-(substituted phenoxyacetoxy)alkylphosphonates

Abstract

A series of 2-methylpropan-2-aminium O-methyl 1-(substituted phenoxyacetoxy)alkylphosphonates (5a-5o) was selectively synthesized by reacting the corresponding O,O-dimethyl 1-(substituted phenoxyacetoxy)-alkylphosphonates with an excess of 2-methylpropan-2-amine. The results of preliminary bioassays show that the title compounds exhibit moderate to good herbicidal activities against Brassica napus and Echinochloa crusgalli. Furthermore, compounds 5a-5j, which show much higher activities than compounds 5k-5o, were selected to further evaluate their post-emergence herbicidal activity at a dosage of 150 g/ha(1 ha=10000 m²). Especially, 2-methylpropan-2-aminium O-methyl 1-[2-(4-chloro-2-methylphenoxy)acetoxy]butylphosphonate(5h) shows 100% inhibitory effect on the growth of Brassica juncea and Amaranthus retroflexus, which is comparable with the commercial herbicide 2,4-dichlorophenoxy acetic acid(2,4-D).

Keywords

Herbicidal activity / Phosphonate / 2-Methylpropan-2-aminium

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