Glycine betaine-based ionic liquids and their influence on bacteria, fungi, insects and plants

Kaczmarek, Damian Krystian; Gwiazdowska, Daniela; Juś, Krzysztof; Klejdysz, Tomasz; Wojcieszak, Marta; Materna, Katarzyna; Pernak, Juliusz

doi:10.1039/d1nj00498k

Cited by 18 publications

(11 citation statements)

References 59 publications

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“…Measurements of surface tension and contact angle were carried out using a DSA 100E analyzer (Krüss, Germany, accuracy ± 0.01 mN m –1 ) at 25 °C, following a methodology described recently . Surface tension was determined by the drop shape method.…”

Section: Methodsmentioning

confidence: 99%

“…Measurements of surface tension and contact angle were carried out using a DSA 100E analyzer (Kruss, Germany, accuracy ± 0.01 mN m −1 ) at 25 °C, following a methodology described recently. 24 Surface tension was determined by the drop shape method. The method depends on the formation of an axisymmetric drop at the tip of the needle of a syringe, after which the image of the drop is acquired with a USB 3 uEye CP camera (IDS Imaging Development Systems GmbH, Obersulm, Germany) and digitized.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Sustainable Design of New Ionic Forms of Vitamin B₃ and Their Utilization as Plant Protection Agents

Stachowiak

Kaczmarek

Rzemieniecki

et al. 2022

J. Agric. Food Chem.

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This study demonstrates the utilization of naturally occurring nicotinamide (vitamin B 3 ) in the sustainable synthesis of organic salts with application potential as environmentally friendly agrochemicals. The designed ionic pairs, obtained with high yields, consisted of N-alkylnicotinamide cation and commercially available herbicidal anions: 2,4-dichlorophenoxyacetate (2,4-D) and 4-chloro-2-methylphenoxyacetate (MCPA). The study confirmed the strong influence of the length of alkyl chain in products on the physicochemical properties as well as the development of cornflower and oil-seed rape. The majority of tested salts showed significantly better herbicidal activity (by approx. 30−50%) compared to the reference herbicide. Furthermore, Nhexadecylnicotinamide 4-chloro-2-methylphenoxyacetate was significantly more effective than the commercial formulation in the dose−response test. Their negligible vaporization, multiple times lower than that of commonly used dimethylammonium salts, eliminates one of the greatest threats of currently applied plant protection agents. Additionally, the risk of product migration or bioaccumulation in the environment was assessed as extremely low.

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Section: Methodsmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Sustainable Design of New Ionic Forms of Vitamin B₃ and Their Utilization as Plant Protection Agents

Stachowiak

Kaczmarek

Rzemieniecki

et al. 2022

J. Agric. Food Chem.

Self Cite

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“…They are widely used as molecular solvents in the areas of synthesis and separation science, as media in catalysis, electrolytes, lubricants, and other task-specific materials [ 1 , 2 ]. ILs are used are not only in chemistry, physics, and materials science but, with the exploration of their biological activity, very often also in medicine, pharmacy, and agrisciences [ 3 ]. Importantly, their physicochemical properties, described as tunable and designable, need to be always properly recognized and defined.…”

Section: Introductionmentioning

confidence: 99%

Influence of Alkyl Chain Length on Thermal Properties, Structure, and Self-Diffusion Coefficients of Alkyltriethylammonium-Based Ionic Liquids

Markiewicz

Klimaszyk

Jarek

et al. 2021

IJMS

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The application of ionic liquids (ILs) has grown enormously, from their use as simple solvents, catalysts, media in separation science, or electrolytes to that as task-specific, tunable molecular machines with appropriate properties. A thorough understanding of these properties and structure–property relationships is needed to fully exploit their potential, open new directions in IL-based research and, finally, properly implement the appropriate applications. In this work, we investigated the structure–properties relationships of a series of alkyltriethylammonium bis(trifluoromethanesulfonyl)imide [TEA-R][TFSI] ionic liquids in relation to their thermal behavior, structure organization, and self-diffusion coefficients in the bulk state using DSC, FT-IR, SAXS, and NMR diffusometry techniques. The phase transition temperatures were determined, indicating alkyl chain dependency. Fourier-transformed infrared spectroscopy studies revealed the structuration of the ionic liquids along with alkyl chain elongation. SAXS experiments clearly demonstrated the existence of polar/non-polar domains. The alkyl chain length influenced the expansion of the non-polar domains, leading to the expansion between cation heads in polar regions of the structured IL. 1H NMR self-diffusion coefficients indicated that alkyl chain elongation generally caused the lowering of the self-diffusion coefficients. Moreover, we show that the diffusion of anions and cations of ILs is similar, even though they vary in their size.

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“…Then the solvent was removed and 50 mL of acetonitrile was added to dissolve the residue. Then the solution was stirred for 30 min and the remaining KCl was filtered off 25,26 . This process was repeated three times.…”

Section: Synthesismentioning

confidence: 99%

“…The CnTA halides were converted to quaternary ammonium hydroxides. Then a stoichiometric amount of salicylic acid was added into the system and a neutralization reaction took place 25,26 . Hence, the crude products of the ILs were further purified to obtain a crystal in acetonitrile.…”

Section: Fungicidal Activitymentioning

confidence: 99%

Synthesis and fungicidal activity of alkyltrimethylammonium salicylate ionic liquids

Zhao

Gao

2022

ITM Web Conf.

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Three alkyltrimethylammonium salicylates (CnTASal) with different alkyl side chains were synthesized and characterized. Solubility, surface activity, and biological activity of the ionic liquids were determined. The results of solubility and surface activity showed that the synthesized ILs are amphiphilic surface-active compounds. Five common agricultural fungi, Valsa mali, Rhizoctonia solani, Fusarium graminearum, Phytophthora capsica and Alternaria solani were tested to identify the most sensitive strain and Valsa mali was selected for the structure-activity relationship (SAR) study. The results of the study revealed that the antifungal activity of the ILs is positively related to the alkyl chains length.

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Glycine betaine-based ionic liquids and their influence on bacteria, fungi, insects and plants

Abstract: A new group of bioinspired ionic liquids (ILs) based on glycine betaine and natural or synthetic anions was synthesized. The developed synthesis methods enabled the preparation of designed salts with...

Cited by 18 publications

References 59 publications

Sustainable Design of New Ionic Forms of Vitamin B₃ and Their Utilization as Plant Protection Agents

Sustainable Design of New Ionic Forms of Vitamin B₃ and Their Utilization as Plant Protection Agents

Influence of Alkyl Chain Length on Thermal Properties, Structure, and Self-Diffusion Coefficients of Alkyltriethylammonium-Based Ionic Liquids

Synthesis and fungicidal activity of alkyltrimethylammonium salicylate ionic liquids

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Glycine betaine-based ionic liquids and their influence on bacteria, fungi, insects and plants

Abstract: A new group of bioinspired ionic liquids (ILs) based on glycine betaine and natural or synthetic anions was synthesized. The developed synthesis methods enabled the preparation of designed salts with...

Cited by 18 publications

References 59 publications

Sustainable Design of New Ionic Forms of Vitamin B3 and Their Utilization as Plant Protection Agents

Sustainable Design of New Ionic Forms of Vitamin B3 and Their Utilization as Plant Protection Agents

Influence of Alkyl Chain Length on Thermal Properties, Structure, and Self-Diffusion Coefficients of Alkyltriethylammonium-Based Ionic Liquids

Synthesis and fungicidal activity of alkyltrimethylammonium salicylate ionic liquids

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Product

Resources

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Sustainable Design of New Ionic Forms of Vitamin B₃ and Their Utilization as Plant Protection Agents

Sustainable Design of New Ionic Forms of Vitamin B₃ and Their Utilization as Plant Protection Agents