Bis(ammonium) ionic liquids with herbicidal anions

Niemczak, Michał; Giszter, Rafał; Czerniak, Kamil; Marcinkowska, Katarzyna; Walkiewicz, Filip

doi:10.1039/c4ra16151c

Cited by 41 publications

(44 citation statements)

References 28 publications

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“…Owing to the recent advances in plant protection, HILs can be tuned to display potent surface‐active properties, which contribute to the increase of the contact surface between the leaves and active ingredient and thereby to enhancement of adsorption of the herbicide into the plant. The latest studies on HILs have confirmed that the presence of amphiphilic cations in their structure might cause a substantial increase in the herbicidal activity . Therefore, surface activity parameters, such as critical micelle concentration (CMC), surface tension at the CMC ( γ CMC ), the efficiency of surface adsorption on an air–water interface (p C 20 ) and contact angle (CA) on paraffin were determined for the obtained compounds comprising a hexyl or longer alkyl substituent in the cation ( 2 b – 7 b , 2 c – 7 c , 2 d – 7 d ).…”

Section: Resultssupporting

confidence: 92%

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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Section: Resultssupporting

confidence: 92%

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

et al. 2018

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“…The thermal stability increased in the following order considered of anions: Dicamba<Pel<MCPP‐P<MCPA<2,4‐DP<2,4‐D<ISM. This dependence can be explained by the increase of nucleophilicity of the anion with which thermal stability decreases from 189 °C for 2 to 177 °C for 7 . The obtained ILs were degraded in a similar temperature range, which may indicate that the acetylcholine cation was preferentially degraded.…”

Section: Resultsmentioning

confidence: 90%

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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“…Although there are herbicides such as e.g. MCPA, against which we have not observed a phenomenon of weeds' resistance, there is a continuous need to search towards new compounds exhibiting selective or global herbicidal properties, which are also harmless for humans, animals and the whole natural environment in its broadest sense [1,6,7].…”

Section: Introductionmentioning

confidence: 99%

The Effect of Ionic Liquids With (–)-Menthol Derivative Containing a Chloride Anion to Weed

Biczak

Pawłowska

Feder‐Kubis

2017

Ecological Chemistry and Engineering S

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Weeds constitute a huge group of undesirable plants, widespread throughout the world. They represent a big problem for most farmers, who implement different methods to fight against them. Thanks to their wide occurrence, weeds however, can be an excellent indicator of the quality of soil and the whole environment where they are present. In this paper, we present the impact of four alkylimidazolium chlorides with a natural terpene component introduced into the soil: (1R,2S,5R)-(-)-menthol and alkyl substituents containing 1, 4, 9 or 12 carbon atoms, on the growth and development of selected weed species. Compounds with the highest phytotoxic activity towards gallant soldier, white goosefoot and common sorrel were chlorides with methyl and butyl substituents, while compounds with nonyl and dodecyl substituents demonstrated a weak effect on these weeds. Phytotoxicity of the salts tested was largely dependent on the applied concentration of the compound and the genetic make-up of plant species used in the experiment. This was reflected in the inhibition of plants' length and their roots, as well as changes in the content of dry matter and photosynthetic pigments.

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Bis(ammonium) ionic liquids with herbicidal anions

Abstract: The method of synthesis of the novel bis(ammonium) herbicidal ionic liquids with the cation containing two quaternary nitrogen atoms was described.

Cited by 41 publications

References 28 publications

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

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

Herbicidal Ionic Liquids Containing the Acetylcholine Cation

The Effect of Ionic Liquids With (–)-Menthol Derivative Containing a Chloride Anion to Weed

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