Preparation and characterization of new ionic liquid forms of 2,4-DP herbicide

Niemczak, Michał; Biedziak, Agnieszka; Czerniak, Kamil; Marcinkowska, Katarzyna

doi:10.1016/j.tet.2017.11.032

Cited by 29 publications

(29 citation statements)

References 55 publications

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“…The values of the octanol‐water partition coefficient depend strictly on the concentration, therefore for this study the salts doses were equal to the doses used for studying the herbicidal activity. The obtained results were compared with the literature values for herbicidal acids,, and presented in Figure and ESI – Table S9.…”

Section: Resultsmentioning

confidence: 99%

“…The prepared ILs with acetylcholine cation are new compounds. Ionic liquids with anions: Dicamba, 2,4‐D,,, 2,4‐DP, MCPP, pelargonate (Pel) and iodosulfuron methyl (ISM) are known in the literature.…”

Section: Resultsmentioning

confidence: 99%

“…The highest value was obtained for 3 and the lowest for 6 , because this IL has the lowest surface tension and affinity of the solute for the hydrophobic surface. It was previously established that lower surface tension and contact angle may result in better herbicidal activity . Lower values of these properties allow for more efficient wetting of the leaf surface and thus easier absorption of the compound and penetration into the plant.…”

Section: Resultsmentioning

confidence: 99%

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Herbicidal Ionic Liquids Containing the Acetylcholine Cation

et al. 2019

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This study presents a new group of herbicidal ionic liquids (HILs) based on a cation occurs commonly in nature−acetylcholine. The HILs were obtained with a high yield through ion exchange between acetylcholine chloride and potassium or sodium salts of selected acids with herbicidal activity. The results of the herbicidal activity measurement against common oilseed rape (Brassica napus L.) exceeded those of the commercial products. Spray solutions of the synthesized HILs revealed high surface activity and wetting properties which further manifested as higher herbicidal activity. The reduction of surface tension and low contact angles together with the specific action of acetylcholine allowed for better penetration of synthesized HILs into plant tissues. In addition, OECD 301F tests confirmed high mineralization of the HILs. The simple transformation of commercial herbicides into acetylcholine HILs proved to be a very effective method of increasing their activity, and constitutes an interesting solution to the problem of weed infestation with the use of a substance commonly found in nature.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Herbicidal Ionic Liquids Containing the Acetylcholine Cation

et al. 2019

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“…All the HILs comprising the dicamba anion ( 1 c – 7 c ) possessed noticeably lower log K OW than HILs with MCPA anion ( 1 b – 7 b ). Owing to increasing hydrophobicity, the chain elongation induced an increase of the analyzed parameter for HILs, which is consistent with the literature . However, the most significant increase of log K OW was effected by an increase in the length of alkyl chain from butyl to octyl.…”

Section: Resultsmentioning

confidence: 99%

“…On the one hand, low K OW values have been correlated with a reduction of bioaccumulation and toxicity in fish, as well as sorption to soils and sediments . On the other hand, it was also found that higher values of log K OW (between 0.6–1.0) might be connected with the enhancement of herbicidal activity of HILs, due to their better surface activity and lipophilicity, resulting in greater spray retention, absorption, cuticle penetration and translocation of the active ingredient in the plant …”

Section: Resultsmentioning

confidence: 99%

Synthesis and Structure–Property Relationships in Herbicidal Ionic Liquids and their Double Salts

et al. 2018

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In this study, two homologous series of novel herbicidal ionic liquids (HILs) were synthesized in a simple metathesis reaction between alkyl[2‐(2‐hydroxyethoxy)ethyl]dimethylammonium bromides and alkali metal salts of 4‐chloro‐2‐methylphenoxyacetic acid (MCPA) or 3,6‐dichloro‐2‐methoxybenzoic acid (dicamba), known as popular herbicides from the class of growth regulators. These HILs were subsequently mixed to prepare double‐salt herbicidal ionic liquids (DSHILs). The DSHILs were characterized by substantially altered parameters of viscosity, refractive index, glass transition temperatures and surface activity compared to the average values expected for ideal mixtures of their individual components (HILs). Interestingly, DSHILs possessed superior physicochemical properties such as relatively low viscosity or facilitated formation of micelles, which emphasizes the complex nature of multi‐ion interactions in the microstructures of ionic liquid mixtures. The biological tests showed improved efficiency of DSHILs against tested weeds compared to the reference herbicides and parent HILs.

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A comprehensive study demonstrating the influence of the solvent composition on the phytotoxicity of compounds, as exemplified by 2,4‐D‐based ILs with a choline‐type cation

Niemczak

Stachowiak

Kaczmarek

et al. 2023

Pest Management Science

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BackgroundGrowing concern for the protection of the environment and existing ecosystems has resulted in increasing consideration of phytotoxicity tests as valid ecotoxicological indicators of the potential hazards of the use of ionic liquids (ILs) or any other chemical. The objective of this study was to gain a detailed understanding of the influence of the solvent composition of spray solutions on the phytotoxic effect of foliar application of ionic pairs with weak (choline 2,4‐dichlorophenoxyacetate, [Chol][2,4‐D]), medium (N‐hexylcholine 2,4‐dichlorophenoxyacetate, [C6Chol][2,4‐D]) and good (N‐dodecylcholine 2,4‐dichlorophenoxyacetate, [C12Chol][2,4‐D]) surface‐active properties.ResultsExperimental results unambiguously demonstrated that the biological activity of the test salt solutions, particularly [Chol][2,4‐D] and [C6Chol][2,4‐D], can be strongly affected by the addition of an organic solvent, such as methanol, ethanol, dimethylformamide (DMF) or dimethylsulfoxide (DMSO) compared to solutions in pure water. However, the observed tendency is less pronounced for the compound exhibiting good surface activity, [C12Chol][2,4‐D].ConclusionsThe collected findings show that caution is warranted in the exploitation or modification of methodologies for assessing phytotoxicity to ensure the reliable interpretation of obtained results for environmental risk assessment or building quantitative structure–activity relationship (QSAR) models. © 2023 Society of Chemical Industry.

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Preparation and characterization of new ionic liquid forms of 2,4-DP herbicide

Cited by 29 publications

References 55 publications

Herbicidal Ionic Liquids Containing the Acetylcholine Cation

Herbicidal Ionic Liquids Containing the Acetylcholine Cation

Synthesis and Structure–Property Relationships in Herbicidal Ionic Liquids and their Double Salts

A comprehensive study demonstrating the influence of the solvent composition on the phytotoxicity of compounds, as exemplified by 2,4‐D‐based ILs with a choline‐type cation

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