Designing Safer Functionalized Ionic Liquids: Monoterpene-Derived Compounds for Greener Agrochemical Development
Przemysław Pietrusiak, Barbara Pawłowska, Magdalena Bendová, Robert Biczak, Joanna Feder-Kubis
TL;DR
Researchers designed safer ionic liquids using monoterpene derivatives to reduce environmental harm in agrochemicals.
Contribution
A workflow for green-by-design criteria of ionic liquids based on phytotoxicity and physicochemical properties.
Findings
Menthol-based sulfonylimide FILs showed higher phytotoxicity than sulfonate analogues.
Linear cation FILs were more phytotoxic and had higher log KOW/BCF than cyclic ones.
Fluorinated anions increased hydrophobicity, bioaccumulation, and toxicity.
Abstract
The environmental behavior and phytotoxicity of functionalized ionic liquids (FILs) featuring imidazolium cations bearing a cyclic (−)-menthol or a linear 1-decanol-derived substituent and fluorinated anions were evaluated in a soil bioassay (Raphanus sativus). Structure–activity relationships were determined by integrating measurements (water solubility, surface tension, molecular volume) with in-silico descriptors (n-octanol–water partition coefficient, log K OW; bioconcentration factor, log BCF; asymmetry). Lipophilicity and bioaccumulation correlated with fresh-mass inhibition (EC50). More-fluorinated, larger, and charge-delocalized anions were more hydrophobic, elevating bioaccumulation and toxicity. Within menthol-based series, sulfonylimide-based FILs were more phytotoxic (EC50 74.7, 107.3 mg·kg–1 soil dry weight) than sulfonate analogues (e.g., 299.1 mg·kg–1). FILs with linear…
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Taxonomy
TopicsIonic liquids properties and applications · Lubricants and Their Additives · Plant Growth Enhancement Techniques