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A total of sixty-three choline derivative-based ionic liquids in the forms of chlorides, acesulfamates, and bis(trifluoromethylsulfonyl)imides have been prepared and their physical properties (density, viscosity, solubility, and thermal stability) have been determined. Thirteen of these salts are known chlorides: precursors to the 26 water-soluble acesulfamates, 12 acesulfamates only partially miscible with water, and 12 water-insoluble imides. The crystal structures for two of the chloride salts-(2-hydroxyethyl)dimethylundecyloxymethylammonium chloride and cyclododecyloxymethyl(2-hydroxyethyl)dimethylammonium chloride-were determined. The antimicrobial (cocci, rods, and fungi) activities of the new hydrophilic acesulfamate-based ILs were measured and 12 were found to be active. The alkoxymethyl(2-hydroxyethyl)dimethylammonium acesulfamates have been shown to be insect feeding deterrents and thus open up a new generation of synthetic deterrents based on ionic liquids. The alkoxymethyl(2-decanoyloxyethyl)dimethylammonium bis(trifluoromethylsulfonyl)imides have also been shown to act as fixatives for soft tissues and can furthermore be used as substitutes for formalin and also preservatives for blood.

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The transformation of agrochemicals into herbicidal ionic liquids (HILs) has been suggested as a solution to problems associated with commercial forms of herbicides. The aim of this review was to summarize the latest progress in the field of HILs, including their synthesis as well as physicochemical and biological properties, and to address the areas that require further research in order to ensure their safe commercialization (e.g., data regarding biodegradability, toxicity, and environmental fate). The first part of the review provides an in-depth summary of the current state of knowledge regarding HILs, particularly the anions and cations used for their synthesis. The second part highlights the employed synthesis methods and elucidates their respective advantages and limitations. The third section is focused on the characterization of HILs with emphasis on the methods and factors that are significant in terms of their practical application. Subsequently, the issues associated with the biodegradation and toxic effects of HILs are discussed based on the relevant literature reports. All sections include comprehensively tabulated data in order to enable rapid comparison of utilized approaches. Finally, all the findings are critically analyzed in terms of crucial disadvantages (especially the lack of standardization), which allowed us to establish future recommendations and basic guidelines that are presented in the last section.

Three herbicidal ionic liquids (HILs)—alkyldi(2-hydroxyethyl)methylammonium (2,4-dichlorophenoxy)acetate, dialkyldimethylammonium (2,4-dichlorophenoxy)acetate, and alkyltrimethylammonium (2,4-dichlorophenoxy)acetate—were synthesized and their activity against broad-leaved weeds was investigated under field conditions. HILs as [cation][2,4-D] used in winter wheat were much more active compared to 2,4-D-dimethylammonium salt and demonstrated efficacy similar to 2,4-D 2-ethylhexyl ester. HILs exhibited desirable surface properties such as low contact angle of droplets and low surface tension. Moreover, the HILs may be safer to operators and neighboring plants due to their nonvolatile nature. HILs at 450 g ha−1 of 2,4-D did not injure wheat.

This study focused on evaluating the toxicity as well as primary and ultimate biodegradability of morpholinium herbicidal ionic liquids (HILs), which incorporated MCPA, MCPP, 2,4-D or Dicamba anions. The studied HILs were also subjected to determination of surface active properties in order to assess their influence on toxicity and biodegradability. The study was carried out with microbiota isolated from different environmental niches: sediments from river channel, garden soil, drainage trench collecting agricultural runoff stream, agricultural soil and municipal waste repository. The obtained results revealed that resistance to toxicity and biodegradation efficiency of the microbiota increased in the following order: microbiota from the waste repository > microbiota from agricultural soil ≈ microbiota from an agricultural runoff stream > microbiota from garden soil > microbiota from the river sludge. It was observed that the toxicity of HILs increased with the hydrophobicity of the cation, however the influence of the anion was more notable. The highest toxicity was observed when MCPA was used as the anion (EC50 values ranging from 60 to 190 mg L−1). The results of ultimate biodegradation tests indicated that only HILs with 2,4-D as the anion were mineralized to some extent, with slightly higher values for HILs with the 4-decyl-4-ethylmorpholinium cation (10–31 %) compared to HILs with the 4,4-didecylmorpholinium cation (9–20 %). Overall, the cations were more susceptible (41–94 %) to primary biodegradation compared to anions (0–61 %). The obtained results suggested that the surface active properties of the studied HILs may influence their toxicity and biodegradability by bacteria in different environmental niches.

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