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The COVID-19 pandemic highlighted the need to create and study new substances with improved lipophilicity and antimicrobial properties, such as ionic liquids (ILs), with easily tunable physicochemical properties. Most ILs possess strong antibacterial effects, but ILs containing the imidazolium cation are even more effective than the positive control. Thus, in this study, three ionic liquids with 1-butyl-3-methylimidazolium cation and various carboxylate anions (phenylacetate, benzoate, and 4-methoxyphenylacetate) were synthesized and fully characterized. The interactions between the cations and anions were discussed based on the experimental density, viscosity, and electrical conductivity. From the measured electrical conductivity and viscosity, the Walden plot is constructed and ionicity of the studied ILs is discussed. The similarities and dissimilarities among the studied ILs and their physicochemical properties are analyzed by applying the hierarchical cluster analysis and in silico calculated properties. The antimicrobial activity of the studied ionic liquids is tested on two bacterial (E. coli and P. aeruginosa) and three fungi (P. verrucosum, A. flavus, and A. parasiticus) strains, finding that they showed improved antimicrobial activity compared to the individual components.
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Antiinfecciosos , Ácidos Carboxílicos , Líquidos Iónicos , Líquidos Iónicos/química , Líquidos Iónicos/farmacología , Antiinfecciosos/farmacología , Antiinfecciosos/química , Antiinfecciosos/síntesis química , Ácidos Carboxílicos/química , Ácidos Carboxílicos/farmacología , Viscosidad , Imidazoles/química , Imidazoles/farmacología , Imidazoles/síntesis química , Conductividad Eléctrica , Pruebas de Sensibilidad Microbiana , Simulación por Computador , Escherichia coli/efectos de los fármacos , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/síntesis química , COVID-19/virologíaRESUMEN
The widespread use of ionic liquids (ILs) as greener solvents in analytical sciences, especially in sample pretreatment, has focused attention on exploiting their enormous potential, not only on eliminating and improving the drawbacks faced by scientists. These ionic compounds with unique physicochemical properties can be tuned through smart synthesis, combining cations and anions, so that the compound exhibits excellent properties for its intended purpose. Ionic liquids are rightly referred to as designer solvents. Validation of a newly proposed analytical methods using ionic liquids, either in sample preparation or in further analysis, is a critical process to demonstrate that a particular analytical method is fit for purpose and provides reliable and accurate results. In addition, this article specially addressed the potential toxicity of ionic liquids with the modest goal of assisting researchers in this field by expanding their target areas.
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5-Hydroxymethylfurfural (HMF), a Maillard reaction product, can be formed when honey is subjected to heat treatment or a long storage time, becoming volatile and toxic depending on its concentration. The fact that, until today, there is no literature data on the extraction of 5-hydroxymethylfurfural (HMF) from honey using ionic liquids directed the investigation of the influence of biodegradable cholinium ionic liquids on the formation of aqueous biphasic systems and the application of these systems for the extraction of HMF from honey. The influence of anions of synthesised ionic liquids on the construction of biphasic systems in which an inorganic salt was used as a salting agent was investigated. Then, the extraction of HMF in these systems was examined, and the mechanisms of HMF extraction using ionic liquids were explained using computer simulations. Examining the effect of cholinium ionic liquids (choline chloride ([Ch][Cl]), cholinium nicotinate ([Ch][Nic]), cholinium propionate ([Ch][Prop]), and cholinium butyrate ([Ch][But])) on the formation of aqueous biphasic systems by comparing the phase diagrams, it was concluded that the ability of ionic liquids to form an aqueous biphasic system with tripotassium phosphate (K3PO4) decreases in the following order: [Ch][But] ≈ [Ch][Prop] > [Ch][Nic] > [Ch][Cl]. By applying all tested aqueous biphasic systems for the extraction of HMF from honey, an extraction efficiency of more than 89% was achieved. Complete extraction was achieved using the extraction system with [Ch][But], while the weakest ability to extract HMF was exhibited by the system with [Ch][Cl]. The mechanisms of HMF extraction using ionic liquids are explained on the basis of the optimised structures of the ionic liquid systems with HMF, together with the visualisation of non-covalent interactions, and on the basis of the calculated binding energies ΔGbin, which can be used as a good predictor of the extraction potential of newly synthesised ionic liquids.
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Due to their appealing physiochemical properties, particularly in the pharmaceutical industry, deep eutectic solvents (DESs) and ionic liquids (ILs) are utilized in various research fields and industries. The presented research analyzes the thermodynamic properties of a deep eutectic solvent created from natural molecules, menthol and lauric acid in a 2:1 molar ratio, and an ionic liquid based on two active pharmaceutical ingredients, benzocainium ibuprofenate. Initially, the low solubility of benzocainium ibuprofenate in water was observed, and a hydrophobic natural deep eutectic mixture of menthol:lauric acid in a 2:1 ratio was prepared to improve benzocainium ibuprofenate solubility. In order to determine the solvent properties of DESs and ILs mixtures at different temperatures and their molecular interactions to enhance the solvent performance, the apparent molar volume, limiting apparent molar expansibility, and viscosity B coefficient were estimated in temperature range from 293.15 K to 313.15 K and varying concentration of benzocainium ibuprofenate.
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The presence of emerging substances in surface water is of a great concern knowing they are the main source for community water supply needs. This study describes the development, optimization and application of an analytical method for the determination of ibuprofen in the Danube samples. Caffeine concentrations, as an indicator of human waste, were determined and maximum risk indexes for aquatic organisms were calculated. The Danube samples were collected from ten representative locations. A Solid-phase extraction was used for ibuprofen and caffeine separation and the analysis was performed by High-performance liquid chromatography method. Ibuprofen concentrations ranged (30.62-111.40) ng/L and caffeine (305.94-375.97) ng/L. Low risk on aquatic organisms was determined for ibuprofen and potential sublethal effect for caffeine was obtained. The results indicated that ibuprofen was effectively separated from other substances in the samples under defined chromatographic conditions for short period of time (4 minutes). Applied HPLC method showed good repeatability, accuracy, selectivity and robustness. Further studies including continuous monitoring of caffeine in the Danube are necessary in order to assess the real risks and possible prevention.
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Ibuprofeno , Contaminantes Químicos del Agua , Humanos , Ibuprofeno/análisis , Cromatografía Liquida/métodos , Cafeína/análisis , Organismos AcuáticosRESUMEN
The research presented in this paper aims to investigate the performance of several newly synthesized ionic liquids during 210Pb/210Bi detection in water on a liquid scintillation spectrometer Quantulus 1220 via Cherenkov counting. These experiments have been triggered by the recent reports that certain ionic liquids can act as wavelength shifters, thus significantly increasing the detection efficiency of Cherenkov radiation. The benefit of ionic liquid's addition to the analysed samples is reflected in the detection limit's decrement during 210Pb quantification, which is pertinent considering naturally low levels of 210Pb in aqueous samples. Firstly, it was discovered that ionic liquid, 1-butyl-3-methylimidazolium salicylate, is more efficient than the previously explored 2-hydroxypropylammonium salicylate. Consequently, the impact of a few other ionic liquids on Cherenkov counting efficiency with the same cation group (1-butyl-3-methylimidazolium benzoate, 1-butyl-3-methylimidazolium 3-hydroxybenzoate and 1-butyl-3-methylimidazolium 4-hydroxybenzoate) was also explored to test their potential influence. Molecular simulations have been carried out to reveal which structures of ionic liquids assure wavelength-shifting behavior. The obtained results confirmed that, among the investigated ones, only ionic liquids with the salicylate anion exhibited a wavelength shifting effect.
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Tetracainium salicylate and tetracainium ibuprofenate were synthesized as active pharmaceutical ingredient ionic liquids (API-ILs). These ILs represent a combination of a drug for local anaesthesia (tetracaine) and nonsteroidal anti-inflammatory drugs (salicylic acid and ibuprofen). After IL synthesis, spectroscopic investigations were performed using infrared and nuclear magnetic resonance spectroscopy to confirm their structures. Differential scanning calorimetry and thermogravimetric analysis determined the obtained thermal behaviour of the ionic liquids. Experimental density, viscosity, and electrical conductivity measurements were performed in a wide temperature range to understand the interactions occurring in the obtained pharmaceutically active ionic liquids. All experimental values were well-fitted by the empirical equations. According to the theoretical calculations, weaker interactions of tetracaine with ibuprofenate than with salicylate are found, ascribed to the decreasing molecular symmetry, weakened hydrogen bonding, and increasing steric hindrance of ibuprofenate's alkyl chain.
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The influence of gemini surfactants (GSs) on the charging and aggregation features of anionic sulfate modified latex (SL) particles was investigated by light scattering techniques in aqueous dispersions. The GSs of short alkyl chains (2-4-2 and 4-4-4) resembled simple inert salts and aggregated the particles by charge screening. The adsorption of GSs of longer alkyl chains (8-4-8, 12-4-12, and 12-6-12) on SL led to charge neutralization and overcharging of the particles, giving rise to destabilization and restabilization of the dispersions, respectively. The comparison of the interfacial behavior of dimeric and the corresponding monomeric surfactants revealed that the former shows a more profound influence on the colloidal stability due to the presence of double positively charged head groups and hydrophobic tails, which is favorable to enhancing both electrostatic and hydrophobic particle-GS and GS-GS interactions at the interface. The different extent of the particle-GS interactions was responsible for the variation of the GS destabilization power, following the 2-4-2 < 4-4-4 < 8-4-8 < 12-4-12 order, while the length of the GS spacer did not affect the adsorption and aggregation processes. The valence of the background salts strongly influenced the stability of the SL-GS dispersions through altering the electrostatic interactions, which was more pronounced for multivalent counterions. These findings indicate that both electrostatic and hydrophobic effects play crucial roles in the adsorption of GSs on oppositely charged particles and in the corresponding aggregation mechanism. The major interparticle forces can be adjusted by changing the structure and concentration of the GSs and inorganic electrolytes present in the systems.
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Sales (Química) , Tensoactivos , Tensoactivos/química , Sales (Química)/química , Microesferas , Coloides/química , Adsorción , AguaRESUMEN
Keeping up with cutting edge research in the field of drug delivery, the overall goal of this study was to develop innovative electrospun nanofibers loaded with ionic liquids (ILs) as active pharmaceutical ingredients (APIs). For the first time, a novel approach was examined by combining biocompatible polymer, poly (ethylene oxide) (PEO), and pharmaceutical ILs in an electrospinning process to develop nanofibers with high drug loading (up to 47%). Firstly, two well-known local anaesthetic drugs, lidocaine and procaine, were modified into ILs with the salicylate, forming lidocaine salicylate and procaine salicylate. Its dual-functional nature and increased water solubility for 4- to 10-fold depending on the drug used contribute to overcoming current hurdles encountered by APIs such as poor solubility, low bioavailability, and polymorphism of the solid-state. Nanofibers were formulated using solutions tested for density, viscosity, electrical conductivity, and small-angle X-ray scattering by varying PEO molecular weight and the PEO to IL mass ratio. Scanning electron microscopy showed the surface morphology of the obtained nanofibers, while Fourier transform infrared spectroscopy and differential scanning calorimetry confirmed IL in the nanofibers in an amorphous state. Thus, nanofibers with incorporated IL represent well-known drugs in the new form and a novel dermal application delivery system.
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Líquidos Iónicos , Nanofibras , Preparaciones Farmacéuticas , Sistemas de Liberación de Medicamentos , Solubilidad , Espectroscopía Infrarroja por Transformada de FourierRESUMEN
Ambroxol hydrochloride (AMB), used as a broncho secretolytic and an expectorant drug, is a semi-synthetic derivative of vasicine obtained from the Indian shrub Adhatoda vasica. It is a metabolic product of bromhexine. The paper provides comprehensive and detailed research on ambroxol hydrochloride, gives information on thermal stability, the mechanism of AMB degradation, and data of practical interest for optimization of formulation that contains AMB as an active compound. Investigation on pure AMB and in commercial formulation Flavamed® tablet (FT), which contains AMB as an active compound, was performed systematically using thermal and spectroscopic methods, along with a sophisticated and practical statistical approach. AMB proved to be a heat-stable and humidity-sensitive drug. For its successful formulation, special attention should be addressed to excipients since it was found that polyvinyl pyrrolidone and Mg stearate affect the thermal stability of AMB. At the same time, lactose monohydrate contributes to faster degradation of AMB and change in decomposition mechanism. It was found that the n-th order kinetic model mechanistically best describes the decomposition process of pure AMB and in Flavamed® tablets.
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The present work focuses on modifying a local anaesthetic drug procaine into an ionic liquid and evaluating the resulting thermal behaviour and structural changes. Counter ions, salicylate, ibuprofenate, and docusate, were chosen due to different hydrogen-bonding abilities, molecular size, charge distribution, and functional groups. After synthesis of procaine salicylate, procaine ibuprofenate, and procaine docusate, spectroscopic investigations were performed using infrared (IR) and nuclear magnetic resonance (NMR) spectroscopy to confirm proton transfer. Differential scanning calorimetry (DSC) and thermogravimetric (TG) analysis were used to determine the obtained ionic liquids' thermal behaviour. Experimental measurements of density, viscosity, and electrical conductivity were performed to get insight into the interactions occurring in the obtained ionic liquids. The viscosity and electrical conductivity data were analysed using the Vogel-Fulcher-Tammann (VFT) equation, while thermal expansion coefficients were calculated from measured density data. The obtained results found that the synthesised procaine salicylate and procaine docusate an ionic liquid's behaviours, including weak intermolecular forces, while procaine ibuprofenate showed more liquid co-crystal behaviour due to the absence of proton transfer for ibuprofen. In a theoretical phase of the investigation, the density functional theory (DFT) and molecular dynamics (MD) calculations were conducted. The obtained descriptors and radial distribution functions were used to analyse the interactions between ions of synthesised ionic liquids. In addition, solubility determination results proved that procaine transformation into procaine salicylate and procaine ibuprofenate ionic liquids enhanced its solubility in water, while procaine docusate reduces procaine solubility.
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Líquidos Iónicos , Aniones , Enlace de Hidrógeno , Iones , ProcaínaRESUMEN
The possibility to prevent nutrition-related diseases that include scavenge of free radicals and to block chain reactions is very important and significant for human well-being. The aim of this study was to analyse different basil extracts, determine the relationship between total phenolic/flavonoid content and antioxidant activity in order to optimize its application in industry. The extraction involved different solvents (ethanol, methanol and water), extraction time (10 and 30 min and 24, 48 and 72 h), plant fragmentation level (0.3 and 2 mm) and the presence or absence of light. Antioxidant activity was investigated by applying spectrophotometric method and measuring the total phenolic and flavonoid content and DPPH radical scavenging activity. The content of total phenolics varied from 5.2 to 185.6 mg of gallic acid equivalents per gram of a dry extract and flavonoids ranged from 0.2 to 35.0 mg of quercetin per gram of a dry extract. All extracts presented a scavenging capacity and IC50 values of DPPH radical inhibition ranged from 0.04 to 12.99 µg/ml. The evaluation of experimental data for eighty basil extracts was performed by chemometric analysis showing good correlation between yield and total phenolic compounds, as well as flavonoid content and inhibition of the DPPH radical.
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Ocimum basilicum , Antioxidantes , Flavonoides , Fenoles , Extractos Vegetales/farmacologíaRESUMEN
The analytical performance of sensitive and cost-effective electrochemical sensors based on ionic liquids (ILs) with the bis(trifluoromethylsulfonyl)imide anion, [NTf2]-, and the imidazolium cation with different alkyl chain lengths for electrochemical oxidation of verapamil (VER) was investigated. 1-Ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([EMIM][NTf2]), 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([BMIM][NTf2]) and 1-hexyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([HMIM][NTf2]) were studied as possible materials for modification of a carbon paste electrode (CPE) for trace-level determination of VER. The experimental parameters including selection of the working electrode, the pH of working media, and the amount of CPE modifiers were investigated. Among them, the [EMIM][NTf2]-CPE with 4.3 wt% of IL was selected as the most appropriate for the square wave voltammetric (SWV) determination of VER at pH 5.0. Cyclic voltammetric studies showed that the electrochemical oxidation of VER was adsorption controlled. Consequently, the square wave adsorptive stripping voltammetric (SW-AdSV) parameters were optimized with Eacc = -0.4 V and tacc = 180 s as the most suitable for accumulation of VER on the electrode surface. The electroanalytical performance of the [EMIM][NTf2]-CPE was further improved by its in situ electrochemical modification with ß-cyclodextrin (ß-CD) and the linear concentration range of VER was from 0.006 to 0.129 µg mL-1; the relative standard deviation did not exceed 0.7%, and the evaluated limit of detection in model solution was 0.002 µg mL-1. The ß-CD/[EMIM][NTf2]-CPE showed adequate selectivity towards VER in the presence of inorganic ions and interferents usually found in human urine. The proposed sensor was successfully applied for VER determination in a spiked human urine sample and pharmaceutical formulation with good repeatability and recovery.
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Ciclodextrinas , Líquidos Iónicos , beta-Ciclodextrinas , Carbono , Composición de Medicamentos , Electrodos , Humanos , VerapamiloRESUMEN
Possible application of a novel ionic liquid 3-methylpiridinium salicylate (3-MPS) in Liquid Scintillation Counting measurements has been explored. Its addition to several radionuclides' aqueous solutions shown a significant influence on 210Pb Cherenkov spectra, 210Pb and 226Ra gross alpha/beta spectra, even on 3H spectra appearance. 3-MPS manifested both wavelength shifting and scintillating effect, indicating that 3-MPS or other ionic liquids of similar structure soon might be implemented into the common LSC practise as an alternative to the commercial LSC cocktails.
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One hundred honey samples of different floral origin (acacia, sunflower, meadow, and forest) collected from nine European countries (Serbia, Albania, Croatia, Montenegro, Romania, Bulgaria, Bosnia and Herzegovina, North Macedonia and Hungary) were analysed for various physicochemical, sensory, antioxidant and antibacterial parameters. The relative antioxidant capacity index and relative antibacterial index were calculated, integrated and expressed as a new property - Power of Honey, intended to be used to predict the health potential of a honey based on its antioxidant and antibacterial activities. Free acidity and colour coordinates L* and a* were chosen for building an artificial neural network model for the prediction of honey health potential. These were chosen based on the obtained correlations between the investigated parameters and in light of the simplicity of the analysis. This model successfully predicted the Power of Honey with a gained coefficient of determination of 0.856. Forest honey samples exhibited the highest Power of Honey. This novel approach should make it possible for honey producers to predict the honey health potential of a particular honey based on a quick and simple analysis.
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The increasing application of various surfactants nowadays, may lead to the contamination of the natural environment and represent potential threat to terrestrial higher plants. In this article, the effect of 13 surfactants, with dodecyl alkyl chain and various aromatic (imidazolium, pyridinium, thiazolium) and aliphatic (guanidinium, ammonium, thiosemicarbazidium) polar heads, on germination, development and growth of wheat and cucumber was investigated. The study aimed to prove how changes in lipophilicity of surfactants and their various structural modifications (existence of the aliphatic or aromatic polar group, the introduction of oxygen and sulfur) influence toxicity towards investigated plants. The calculated lipophilic parameter (AlogP) is shown to be a useful parameter for predicting potential toxicity of the compound. The strategy of using surfactants with aliphatic polar heads instead of aromatic prove to be a promising strategy in reducing harmful effect, as well as the introduction of polar groups in the structure of cation. From all investigated compounds, surfactants with imidazolium polar head displayed the most harmful effect towards wheat and cucumber. The cucumber seeds were more sensitive to the addition of surfactants comparing to wheat. All obtained experimental results were additionally investigated using computational methods, simulating the transport of surfactants through a lipid bilayer. The influence of cation tendency to fit in lipid bilayer structure was correlated with toxicity. For the first time, it is concluded that cation ability to mimic the structure of bilayer have less harmful effect on plant development.
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Cucumis sativus/efectos de los fármacos , Imidazoles/toxicidad , Compuestos de Piridinio/toxicidad , Tensoactivos/toxicidad , Triticum/efectos de los fármacos , Cationes , Membrana Celular/química , Membrana Celular/efectos de los fármacos , Cucumis sativus/crecimiento & desarrollo , Germinación/efectos de los fármacos , Imidazoles/química , Membrana Dobles de Lípidos/química , Simulación de Dinámica Molecular , Compuestos de Piridinio/química , Compuestos de Piridinio/farmacología , Plantones/efectos de los fármacos , Plantones/crecimiento & desarrollo , Semillas/efectos de los fármacos , Semillas/crecimiento & desarrollo , Relación Estructura-Actividad , Tensoactivos/química , Triticum/crecimiento & desarrolloRESUMEN
The purpose of this paper was to examine the density, viscosity and electrical conductivity at different temperatures, as well as the thermal stability and structural properties of previously reported ionic liquids based on active pharmaceutical ingredients. Lidocaine-based ionic liquids, with ibuprofen and salicylate as counterion, were prepared first. Their structures were confirmed by infrared, mass and 1H and 13C nuclear magnetic resonance spectroscopy. The Newtonian behaviour of lidocaine ibuprofenate was confirmed from viscosity measurement results, while it was impossible to determine for lidocaine salicylate. The interactions and structures of the studied ionic liquids were analyzed based on the measured density values, viscosity, electrical conductivity, and calculated values of thermal expansion coefficients and activation energy of viscous flow. From a theoretical aspect, DFT and MD calculations were performed. The obtained descriptors and radial distribution, as well as structural functions, were used to understand the structural organization of the synthesized ionic liquids.
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The fungal genus Alternaria Nees 1816 includes the most prevalent pathogenic species that can cause crop diseases such as blight, black spot, and dark leaf spot. In accordance with the aim of developing modern sustainable approaches in agriculture for the replacement of synthetic and toxic substances with environmentally friendly alternatives, the objective of this study was to examine the in vitro antifungal activities of 18 newly synthesized ionic liquids (ILs) against three Alternaria strains: A. padwickii, A. dauci and A. linicola. The antifungal activities of the ILs were estimated via a microdilution method to establish minimal inhibitory concentration (MIC) and minimal fungicidal concentration (MFC) values. The results confirmed that 17 of the 18 ILs showed strain specificity, including good antifungal activity toward Alternaria strains, with MIC and MFC values in the range of 0.04 to 0.43 mol dm-3. The strongest antifungal effects toward all analyzed Alternaria strains were displayed by the compounds with long alkyl chains: [omim][Cl] (MIC/MFC: 0.042 mol dm-3), [dmim][Cl] (MIC/MFC: 0.043 mol dm-3), [ddmim][Cl] (MIC/MFC: 0.053 mol dm-3), [ddTSC][Br] (MIC/MFC: 0.053 mol dm-3), and [Allyl-mim][Cl] (MIC/MFC: 0.054 mol dm-3). The introduction of oxygen as a hydroxyl group resulted in less-pronounced toxicity towards Alternaria compared to the introduction of an ether group, while the contribution of the hydroxyl group was shown to be a more determining factor than the prolongation of the side-chain, resulting in overall fungicidal activity decrease. Our results indicate the possibility that the most effective ILs ([Allyl-mim][Cl], [omim][Cl], [dmim][Cl], [ddmim][Cl], [bTSC][Br], [hTSC][Br], [oTSC][Br], [dTSC][Br], and [ddTSC][Br]) could be applied to the control of plant diseases caused by Alternaria species, based on their potential as an environmentally friendly crop protection approach. Since salts based on TSC cations are significantly cheaper to synthesize, stable under mild conditions, and environmentally friendly after degradation, thiosemicarbazidium-based ILs can be a suitable replacement for commercially available imidazolium ILs.
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The purpose of the present study was to examine the effectiveness of 23 different synthesized ionic liquids (ILs) on Fusarium culmorum and Fusarium oxysporum growth rate. The strategy of IL synthesis was a structural modification of ionic liquids through changing the polarity of imidazolium and pycolinium cations and replacing halide anions with well known antifungal anions (cinnamate, caffeate and mandelate). The findings clearly suggest that the type of alkyl chain on the cation is the most determining factor for IL toxicity. In order to examine how IL structure affects their toxicity towards Fusarium genus, lipophilic descriptor A log P is calculated from density functional theory and correlated with Fusarium growth rate. All these results demonstrate the high level of the interdependency of lipophilicity and toxicity for investigated ILs towards the Fusarium genus. The data collected in this research suggest that the inhibitory influence of ILs is more pronounced in the case of F. oxysporum.
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In this work, new protic ionic liquids (PILs) with 1-ammonium-2-propanol cation and nine different anions: formate (For), acetate (Ac), lactate (Lac), trifluoroacetate (TFA), chloroacetate (ClA), trichloroacetate (TClA), 3-chloropropionate (3-ClP), 4-chlorobutyrate (4-ClB) and mandelate (Man) were prepared in order to study their antimicrobial activity and possible application for fungi and bacteria removal from deteriorated paper heritage. Ten filamentous fungal strains isolated from specific pigmented area of the damaged books: Trichoderma sp., Cladosporium sp., Penicillium sp.(1-3), Penicillium citrinum, Aspergillus sp.(1,2), Aspergillus flavus, Fusarium graminearum, eight Gram positive and Gram negative ATCC bacterial strains: B. subtilis (6633), S. aureus (6538), E. faecalis (19433), K. rhizophila (9341), E. coli (11229), S. enteritidis (13076), P. mirabilis (12453), P. aeruginosa (15692) and two yeast Candida strains: Candida albicans (ATCC 10231) and Candida albicans (L) were used in this study. The results indicated that antimicrobial activity of selected ionic liquids is significantly affected by the size and specific functional groups in the anion structure. These facts opened the possibility for molecular design of new ionic liquids with strong inhibition properties against the specific bacterial, mould and yeast strains. The significant antimicrobial properties observed in this research suggest that studied PILs may have potential applications in the paper art and artefact cleaning and conservation replacing thus, conventional solvents and organic substances that are toxic for humans and environment.