Comparison of the effect of ionic liquids containing hexafluorophosphate and trifluoroacetate anions on the inhibition of growth and oxidative stress in spring barley and common radish

Abstract

Ionic liquids are a group of chemical compounds with chemical properties that are of great interest to various fields of science and industry. However, commercial use of these substances raises concern because they may threaten the natural ecosystems. The present study used 2 types of (-)-menthol-containing imidazolium chiral ionic liquids: 1-[(1R,2S,5R)-(-)-menthoxymethyl]-3-methylimidazolium hexafluorophosphate [Im-Men][PF ] and 1-[(1R,2S,5R)-(-)-menthoxymethyl]-3-methylimidazolium trifluoroacetate [Im-Men][CF CO ]. The effects of these compounds on growth and development of spring barley (Hordeum vulgare) and common radish (Raphanus sativus L. subvar. radicula Pers.) were investigated. The present study demonstrated that chiral ionic liquids produced a relatively high phytotoxicity, by shortening the plants' lengths and roots, thus causing a decline in the experimental plants' fresh weights. The investigated ionic liquids also led to a reduction in photosynthetic pigment levels, changes in hydrogen peroxide and malondialdehyde content, and changes in the activities of superoxide dismutase, catalase, and peroxidase in both plants. Changes in these enzymes were used to indicate oxidative stress levels in spring barley and common radish. It was demonstrated that imidazolium ionic liquid-induced phytotoxicity depended largely on the type of anion. The liquid [Im-Men][PF ] exhibited higher toxicity toward spring barley and common radish seedlings. Common radish was more resistant to chiral ionic liquids. Environ Toxicol Chem 2017;36:2167-2177. © 2017 SETAC.

Ionic Liquids as Environmental Pollutants—Analysis of the Effect of Tetrabutylammonium Chloride on the Growth and Development of Wheat and Cucumber

“…As shown in previous own studies [ 22 , 23 ], not all ILs show an effect on seed germination. The direction of the effect of ILs on germination depends largely on the type of ILs.…”

The need to change the approach to the safe use of herbicides by developing chiral and environmentally friendly formulations: a series of enantioselective (R)- and (S)-phenylethylammonium chloroacetates

“…There are literature reports suggesting that the enantioselective toxicity of chiral, herbicidal ILs depends on their concentration, species tested and the anion type. 41 The highest enantioselectivity is observed in the case of MCA, where the (R)-enantiomer exhibits 9-times higher toxicity towards A. fischeri than the corresponding (S)-enantiomer.…”

“…The differences in results obtained for both species resulted from the dissimilarities in the root systems of monocotyledonous and dicotyledonous plants, which could lead to different sensitivities when being exposed to chemicals. 41,44 Based on the literature reports, (R)-enantiomers are generally more toxic than (S)-enantiomers towards vascular plants, while the reverse is true for microalgae. 2 In this work, the authors proved that (R)enantiomers generally inhibited more the antioxidant enzyme activity in vascular plants, whereas the opposite was generally true for phytoplankton.…”

An Overview on Phytotoxic Perspective of Ionic Liquids and Deep Eutectic Solvents: The Role of Chemical Structure in the Phytotoxicity

“…Among the tested ILs, [C 4 mim][NTf 2 ] was found as more toxic than others. Two ILs containing 1‐[(1R,2S,5R)‐(‐)‐menthoxymethyl] imidazolium ([Im‐Men]) cation and PF 4 and trifluoroacetate (CF 3 CO 2 ) anions for phytotoxic effect on spring barley and common radish were studied 79. These ILs are also known as chiral ILs.…”