Synthesis and Herbicidal Activities of 2-Methylpropan-2-Aminium Methyl 1-(Substituted Phenoxyacetoxy) Alkylphosphonates

Abstract

A series of 2-methylpropan-2-aminium methyl 1-(substituted phenoxyacetoxy) alkylphosphonates were selectively synthesized by reacting the corresponding dimethyl 1-(substitutedphenoxyacetoxy)alkylphosphonates with an excess of 2-methylpropan-2-amine. All the title compounds were identified by IR, ¹H NMR, and ³¹P NMR, some of them were further analyzed by ¹⁹F NMR and ¹³C NMR. Their herbicidal activity was investigated and the results showed that most of the demethylated aminium salts exhibited notable herbicidal activities against Brassica napus L. and Echinochloa crusgalli.

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GRAPHICAL ABSTRACT

Keywords:

• Synthesis
• herbicidal activity
• phosphonate
• 2-Methylpropan-2-aminium

Acknowledgments

This work was supported by the National Basic Research Program of China (2010CB126100), the National Key Technologies R & D Program of China (No. 2011BAE06B03), and the National Natural Science Foundation of China (No. 21172090 and No. 21002037). The research was supported in part by the PCSIRT (No. IRT0953).