Synthesis of Mixed Phosphonate Esters and Amino Acid-Based Phosphonamidates, and Their Screening as Herbicides

Author:

Backx Simon1ORCID,Desmedt Willem23ORCID,Dejaegere Andreas1ORCID,Simoens Andreas1,Van de Poel Jef1,Krasowska Dorota1ORCID,Audenaert Kris2ORCID,Stevens Christian V.1ORCID,Mangelinckx Sven1ORCID

Affiliation:

1. SynBioC Research Group, Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium

2. Laboratory of Applied Mycology and Phenomics, Department of Plants and Crops, Faculty of Bioscience Engineering, Ghent University, Valentin Vaerwyckweg 1, 9000 Ghent, Belgium

3. Plant Sciences Unit, Flanders Research Institute for Agriculture, Fisheries and Food (ILVO), Burg. van Gansberghelaan 96, 9820 Merelbeke, Belgium

Abstract

While organophosphorus chemistry is gaining attention in a variety of fields, the synthesis of the phosphorus derivatives of amino acids remains a challenging task. Previously reported methods require the deprotonation of the nucleophile, complex reagents or hydrolysis of the phosphonate ester. In this paper, we demonstrate how to avoid these issues by employing phosphonylaminium salts for the synthesis of novel mixed n-alkylphosphonate diesters or amino acid-derived n-alkylphosphonamidates. We successfully applied this methodology for the synthesis of novel N-acyl homoserine lactone analogues with varying alkyl chains and ester groups in the phosphorus moiety. Finally, we developed a rapid, quantitative and high-throughput bioassay to screen a selection of these compounds for their herbicidal activity. Together, these results will aid future research in phosphorus chemistry, agrochemistry and the synthesis of bioactive targets.

Funder

BOF-BAS

Hercules Foundation

Publisher

MDPI AG

Cited by 1 articles. 订阅此论文施引文献 订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献

1. Study of Amino Acid-Derived 3-Acyltetramic Acids as Herbicidal Agents;Journal of Agricultural and Food Chemistry;2024-09-03

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