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.
A new group of quaternary ammonium lactate based ionic liquids have been prepared and characterized. Didecyldimethylammonium (DDA) and benzalkonium (BA) D,L- and L-lactates are air-stable, hydrophilic, surface-active salts. They are very effective antibacterial and antifungal agents, especially the DDA lactates, against Streptococcus mutants and Candida albicans. Their activities are comparable or more effective than the original benzalkonium chloride. In addition, they have been shown to be good insect-feeding deterrents. However, they are poor antifungal agents for wood preservation. The toxicity of the DDA and BA lactates has also been studied and the results are presented in this paper.
Studies on the biological activity of synthesised lactones revealed high selectivity towards insect pests as well as bacterial strains. Only the halolactones exhibited significant antifeedant activity. In contrast, antibacterial activity was shown only by the lactone (8) without halogen.
Ionic liquids are effective stored product insect antifeedants. Their activity depends on the type of cation and anion. A group of ionic liquids with inorganic (nitrate, nitrite, hydrogen sulphite, dihydrogen phosphate, thiocyanate, phosphate and tripolyphosphate) and organic (propionate, citrate, sorbate, undecylate, dodecylbenzenesulfonate, acesulfamate and saccharinate) anions was synthesized. Their physicochemical properties, microbial and deterrent activity against Tribolium confusum (larvae and beetles), Sitophilus granarius (beetles) and Trogoderma granarium (larvae) were determined. Ionic liquids with a didecyldimethylammonium cation demonstrated deterrent activity, exceeding the activity of the standard, azadirachtin. The compounds proved to be very effective against pathogenic bacteria and fungi. The appropriate selection of the cation and anion allows the design of economic and effective insect antifeedants. Ionic liquids based insect antifeedants provide novel examples of promising management tools in biorational approaches to stored product pest control.
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