Bioinspired Herbicides-Ionic Liquids or Liquid Cocrystals?

Juliusz Pernak, Marek Łożyński, Damian K. Kaczmarek, Fengrui Qu, Geetha Bolla, Robin D. Rogers

Research output: Contribution to journalArticlepeer-review

Abstract

This research provides information about combinations of several amino acids, including l-proline (Pro), l-arginine (Arg), and l-histidine (His), with phenoxyacetic acid herbicides (MCPA and 2,4-D). Five amino acid ionic liquids (AAILs), one amino acid higher-melting salt (AAHMS), and two amino acid liquid cocrystals (AALCs) were obtained in high yields (>90%). The ionization of the six new structures was confirmed by NMR, IR, and molecular modeling. X-ray crystallography was used to definitively confirm the binding location of the mobile hydrogen. Furthermore, we propose a computational method for estimating the energy of specific hydrogen bond(s) in AAIL crystals based on the NBO and QTAIM hydrogen bond parameters obtained by model calculations. An in-depth analysis of the structures allowed to answer the question posed in the title, ionic liquids or liquid cocrystals? AAILs based on arginine and histidine were obtained. In contrast, combining proline with MCPA and 2,4-D led to AALCs. Finally, the compounds were analyzed to measure their herbicidal activity. These studies proved that the novel form of MCPA or 2,4-D improved its ability to control weeds compared to commercial formulations containing the same active ingredients.

Original languageEnglish
Pages (from-to)1454-1461
Number of pages8
JournalJournal of Agricultural and Food Chemistry
Volume72
Issue number3
DOIs
StatePublished - 24 Jan 2024
Externally publishedYes

Keywords

  • amino acids
  • biological activity
  • crystallography
  • herbicidal ionic liquids
  • molecular modeling

ASJC Scopus subject areas

  • General Chemistry
  • General Agricultural and Biological Sciences

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