Quaternary ammonium nonanoate-based ionic liquids as chemicals for crop protection

Ionic Liquids Derived from Vitamin C as Multifunctional Active Ingredients for Sustainable Stored-Product Management

“…A comparison of the spectra (Figures S4, S8, S12, S16, S22, S26, S30, S36 and S40) reveal that drastic changes in the chemical shifts could only be detected for the C(3) carbon atom, which is directly connected to the negatively charged oxygen atom. Therefore, this signal exhibited shifting toward lower values (shielding) from 1 ppm for oleylmethylbis(2-hydroxyethyl)ammonium ascorbate (10) to even 10 ppm for alkyltrimethylammonium ascorbates (1−3) in all the ILs analyzed. The phenomenon observed may be attributed to the alterations in the electron distribution within the ring of the ascorbate anion caused by the differences in the structures of the alkyl substituents of the cations utilized (see the optimized structures presented in the Supporting Information in Table S13).…”

“…The new products included salts containing a cation substituted with one long alkyl chain trimethyltetradecylammonium (1), hexadecyltrimethylammonium (2), trimethyloctadecylammonium (3), and behenyltrimethylammonium (4); substituted with two long alkyl chains dimethyldioctylammonium (5), didecyldimethylammonium (6), dicocodimethylammonium (7), and di(hydrogenated tallow)dimethylammonium (8); substituted with one long alkyl chain along with a benzyl group benzalkonium (9); and substituted with one long alkyl chain along with two hydroxyethyl groups oleylmethylbis(2-hydroxyethyl)ammonium (10). It is notable that the cations of salts 7, 8, and 10 contain substituents derived from natural feedstocks: coco (from coconut oil), hydrogenated tallow (from animal tallow), and oleyl (from olive oil), which are defined in Table 2.…”

“…Our previous research indicated that ILs with long alkyl chains in the cation derived from sweeteners or some natural acids, such as abietic acid, could exhibit a deterrent activity comparable to the most effective natural antifeedants, such as azadirachtin. 9,10 Bioionic liquids are a group of ILs entirely comprising renewable natural resources. 11 Their unabated popularity is related to the fact that these compounds are usually less harmful to the environment and are more readily biodegradable than the ILs obtained from synthetic substrates.…”

“…12,13 Naturally occurring L-carnitine, choline, or betaine cations are used to synthesize the majority of the bio-ILs, 14,15 while derivatives of fatty acids and carboxylic acids, such as acetic or formic acid, are often utilized as the source of the anion. 10,16,17 Bio-ILs derived from amino acids or sugars have also recently been described in the literature. 18−20 Another bioinspired approach, based on merging an ion of natural origin with the synthetic counterion, proved to possess many advantages, such as facilitating the implementation of the desired properties while reducing adverse impacts on the environment.…”

Third-generation ionic liquids with N-alkylated 1,4-diazabicyclo[2.2.2]octane cations and pelargonate anions

“…25 Deterrent ILs with a pelargonate anion have also been reported. 26 1,4-Diazabicyclo[2.2.2]octane (common name DABCO) is a bicyclic compound that belongs to the group of tertiary diamines. It is widely used as a catalyst for many reactions, both in pristine and modied forms.…”