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“Sweet” ionic liquids comprising the acesulfame anion – synthesis, physicochemical properties and antifeedant activity towards stored product insects
New Journal of Chemistry ( IF 3.3 ) Pub Date : 2020-04-06 , DOI: 10.1039/c9nj06005g
Witold Stachowiak 1, 2, 3, 4 , Tomasz Rzemieniecki 1, 2, 3, 4 , Tomasz Klejdysz 4, 5, 6 , Juliusz Pernak 1, 2, 3, 4 , Michał Niemczak 1, 2, 3, 4
Affiliation  

Ionic liquids (ILs) are known to be useful as agrochemicals; however, their activity strongly depends on the structure of the selected cations and anions. This study is focused on the utilization of acesulfame K, a sweetener commonly used in the food industry, in the synthesis of ILs, their characterization and their application as feeding deterrents (antifeedants) against stored product insects. A new homologous series of “sweet” ILs containing cations functionalized with a diglycol [2-(2-hydroxyethoxy)ethyl] group and an acesulfame anion were obtained with high yields under mild conditions via a two-step process. Subsequently, the influence of the length of the alkyl chain (ranging from ethyl to hexadecyl) in the cations of the functionalized ILs on their various physicochemical properties (phase transitions, thermal stability, density, viscosity, refractive index, solubility and octanol–water partition coefficient) was thoroughly evaluated. The octanol–water partition coefficient values indicate low potential of the obtained products for bioaccumulation in the environment and for leaching into groundwater. Additionally, the synthesized ILs were examined in terms of their antifeedant activity towards widespread stored product pests: the granary weevil, rice weevil, confused flour beetle and khapra beetle. All the obtained ILs exhibited biological activity, and the highest efficacy against tested insects was demonstrated by products comprising long alkyls (tetradecyl and hexadecyl). Additionally, it was established that these ILs were also characterized by the highest octanol–water partition coefficient values. The obtained “sweet” ILs with “designer” physicochemical properties and promising biological activity results exhibit potential for use in the storage of crop protection products.

中文翻译:

包含乙酰磺胺酸阴离子的“甜”离子液体–合成,理化性质和对储藏产品昆虫的拒食活性

已知离子液体(ILs)可用作农药。但是,它们的活性在很大程度上取决于所选阳离子和阴离子的结构。这项研究的重点是在食品合成物质的合成中使用乙酰磺胺酸钾(一种在食品工业中常用的甜味剂),它们的表征以及它们作为对储存的产品昆虫的摄食威慑剂(抗饲料)的用途。在温和的条件下,通过温和的条件,可以高收率获得新的同源系列“甜” IL,它们包含被二甘醇[2-(2-羟基乙氧基)乙基]和乙酰磺胺酸阴离子官能化的阳离子一个两步过程。随后,官能化IL的阳离子中烷基链长度(从乙基到十六烷基)对其各种理化性质(相变,热稳定性,密度,粘度,折射率,溶解度和辛醇-水分配)的影响系数)进行了彻底评估。辛醇-水分配系数值表明,所获得的产品在环境中生物富集和渗入地下水中的潜力很低。此外,还根据合成ILs对广泛储存的产品有害生物的拒食活性进行了检查:粮象鼻虫,水稻象鼻虫,糊涂的甲虫和khapra甲虫。所有获得的IL均具有生物学活性,包含长烷基(十四烷基和十六烷基)的产品证明了对被测昆虫的最高功效。此外,已确定这些IL的特征还在于最高的辛醇-水分配系数值。所获得的具有“设计者”理化特性和有希望的生物活性结果的“甜” IL展示出了用于储存农作物保护产品的潜力。
更新日期:2020-04-24
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