Amino acid-based dicationic ionic liquids as complex crop protection agents

Kaczmarek, Damian Krystian; Gwiazdowska, Daniela; Marchwińska, Katarzyna; Klejdysz, Tomasz; Wojcieszak, Marta; Materna, Katarzyna; Pernak, J.

doi:10.1016/j.molliq.2022.119357

Cited by 9 publications

(9 citation statements)

References 57 publications

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“…Wheat wafer disks dipped in a 1% solution of IL with a didecyldimethylammonium cation demonstrated a strong deterrent activity against the granary weevil Sitophilus granarius (L.) and the confused flour beetle Tribolium confusum with a respective RI of 92.3 and 87.6% . Finally, a series of recent studies using the same bioassay with dicationic, glycine betaine-, and amino acid−based ILs recorded a very good total deterrence coefficient (150−200) on adults of the granary weevil and the confused flour beetle, as well as larvae of the khapra beetle Trogoderma granarium Everts. − …”

Section: Resultsmentioning

confidence: 86%

“…These different reactions can be explained by the chemical nature of ILs. Indeed, it appears that the biological activity of ILs could be dependent on the length of the alkyl chain, the presence of an ester group in the cation, the properties of the anion (hydrophobicity and stability) and the cation (lipophilicity), as well as the concentration used. ,,− Based on these characteristics, ILs will exhibit distinct mechanisms of interaction with cells (membrane binding, insertion, and disruption). Thus, unlike diepoxidized IL which have no ester groups, tri- and tetra-epoxidized ILs show an increase in the number of ester groups from one to two, respectively, which could be the cause of their repellent activity against the pea aphid A.…”

Section: Resultsmentioning

confidence: 99%

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Novel Aphid-Repellent Fiber Mats Based on Poly(lactic acid)-Containing Ionic Liquids

Merlini,

Lacotte,

Castro

et al. 2024

ACS Omega

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To protect crops as well as human and animal health, the development of novel repellents based on biopolymers is critical for a growing world population. Here, novel aphid-repellent electrospun mats containing epoxidized ionic liquids (ILs) covalently bonded to the carboxyl or hydroxyl groups of poly(lactic acid) (PLA) were designed to produce nonwoven mats. First, di-, tri-, and tetraepoxidized imidazolium ILs were synthesized and incorporated in different weight fractions (3, 5, and 10 wt %) into the PLA solution. Then, the effect of ILs' microstructure, thermal properties, mechanical performance, and hydrophobic behavior were investigated. It was found that the incorporation of ILs resulted in a reduction of the fiber diameters while the mechanical properties of the mats, i.e., the threedimensional fibrous porous structure, were maintained. Finally, the effect of these three ILs against the pea aphid Acyrthosiphon pisum (Harris) was evaluated for the first time, showing an attractive effect for the diepoxidized IL and a repellent effect for the tri-and tetra-epoxidized ILs. By exploiting the chemical nature of ILs, an environmentally friendly strategy can be developed to limit the need for chemical pesticides and petroleum-based polymers.

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Section: Resultsmentioning

confidence: 86%

Section: Resultsmentioning

confidence: 99%

Novel Aphid-Repellent Fiber Mats Based on Poly(lactic acid)-Containing Ionic Liquids

Merlini,

Lacotte,

Castro

et al. 2024

ACS Omega

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“…These compounds are the most commonly reported amino acid-based ILs (AAILs) that employ an imidazolium-based cation, which were first reported in 2005 . AAILs are classified as third-generation ionic liquids (ILs), and their main advantage is that the desired physical, chemical, and biological properties can be obtained through structural design …”

Section: Introductionmentioning

confidence: 99%

Bioinspired Herbicides–Ionic Liquids or Liquid Cocrystals?

Pernak,

Łożyński,

Kaczmarek

et al. 2024

J. Agric. Food Chem.

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This research provides information about combinations of several amino acids, including L-proline (Pro), L-arginine (Arg), and L-histidine (His), with phenoxyacetic acid herbicides (MCPA and 2,4-D). Five amino acid ionic liquids (AAILs), one amino acid higher-melting salt (AAHMS), and two amino acid liquid cocrystals (AALCs) were obtained in high yields (>90%). The ionization of the six new structures was confirmed by NMR, IR, and molecular modeling. X-ray crystallography was used to definitively confirm the binding location of the mobile hydrogen. Furthermore, we propose a computational method for estimating the energy of specific hydrogen bond(s) in AAIL crystals based on the NBO and QTAIM hydrogen bond parameters obtained by model calculations. An in-depth analysis of the structures allowed to answer the question posed in the title, ionic liquids or liquid cocrystals? AAILs based on arginine and histidine were obtained. In contrast, combining proline with MCPA and 2,4-D led to AALCs. Finally, the compounds were analyzed to measure their herbicidal activity. These studies proved that the novel form of MCPA or 2,4-D improved its ability to control weeds compared to commercial formulations containing the same active ingredients.

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“…The transformation of well-known compounds into their ionic forms is an effective approach for the synthesis of novel compounds with customized physicochemical properties and biological activity. This approach has previously been used to synthesize novel feeding deterrents, 7 systemic resistance inducers, 8 and plant growth stimulators. 9 Among this group of compounds, one of the ions is characterized by its biological activity, while the other functions as a complementary substance.…”

Section: ■ Introductionmentioning

confidence: 99%

Dicationic Ionic Liquids with an Indole-3-butyrate Anion – Plant Growth Stimulation and Ecotoxicological Evaluations

Kaczmarek,

Pacholak,

Burlaga

et al. 2023

ACS Sustainable Chem. Eng.

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Due to the poor water solubility of indole-3-butyric acid (IBA), adding appropriate adjuvants to this compound during application is essential. The physicochemical properties of plant growth regulators can be easily modified by transforming them into ionic liquids. In this research, IBA was converted into an anion and conjugated with a bis-ammonium cation to form novel dicationic ionic liquids (DILs). The purpose of obtaining these new DILs was to improve the biological activity and determine the effects of the modifications on the stability and persistence of soil microorganisms. The synthesis method enabled the designed DILs to be obtained with yields above 85%. The surface tension and chemical stability results indicated that these properties could be optimized by selecting appropriate cations. A solubility study indicated that the transformation of IBA into DILs improved the solubility of the active ingredient in water. Analysis of the growth-stimulating activity of the DILs on corn showed that the application of DILs significantly increased the fresh and dry cobs' weight compared to control plants. An experiment evaluating the effects of DILs on soil microorganisms showed that high concentrations of IBA anion inhibited bacterial growth and could have distorted cell metabolism. The DILs presented in this research may be potential alternatives to commercially used formulations.

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Amino acid-based dicationic ionic liquids as complex crop protection agents

Cited by 9 publications

References 57 publications

Novel Aphid-Repellent Fiber Mats Based on Poly(lactic acid)-Containing Ionic Liquids

Novel Aphid-Repellent Fiber Mats Based on Poly(lactic acid)-Containing Ionic Liquids

Bioinspired Herbicides–Ionic Liquids or Liquid Cocrystals?

Dicationic Ionic Liquids with an Indole-3-butyrate Anion – Plant Growth Stimulation and Ecotoxicological Evaluations

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