Herbicidal ionic liquids containing double or triple anions as a new potential tool for weed control including herbicide-resistant biotypes

Marcinkowska, Katarzyna; Praczyk, T.; Niemczak, Michał; Rzemieniecki, Tomasz; Kaczmarek, Damian Krystian; Łącka, Agnieszka; Pernak, Juliusz

doi:10.1016/j.cropro.2023.106238

Cited by 3 publications

(5 citation statements)

References 35 publications

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“…HILs are developed from various well-known herbicides, including compounds such as 2,4-dichlorophenoxyacetic acid (2,4-D) [118], 4-chloro-2-methylphenoxyacetic acid (MCPA) [119,120], 2-(4-chloro-2-methylphenoxy)propanoic acid (MCPP) [121], glyphosate [120], clopyralid [122], dicamba [123,124], sulfonylurea derivatives [125,126], and so on. In the initial stages of HIL development, an "anti-crystalline engineering" approach was employed, where cations were selected to enhance salt mobility and prevent crystallization [127].…”

Section: Herbicidal Ils (Hils)mentioning

confidence: 99%

“…A new direction in HIL design involves introducing new biological functions into HILs by adding cations to create a dual-active HIL system [130]. Additionally, researchers have combined herbicidal anions with different herbicidal activities using the same cation to form a double-salt HIL (DSHIL) system with synergistic effects [125]. Recent studies have also delved into synthesizing HILs with growth regulators [131], glyphosate [132], and cinnamic acid [133] as key components.…”

Section: Herbicidal Ils (Hils)mentioning

confidence: 99%

“…The HIL with double salts is composed of compounds that form a charge-balanced system, encompassing three or more ions [136]. Since the first report of double-salt HILs in 2017, researchers have shown increasing interest in exploring this field [125,132]. Various combinations of double-salt HILs have been developed, including those based on synthetic herbicidal agents such as 4-chloro-2-methylphenoxyacetic acid [131,137,138] and dicamba [132].…”

Section: Double-salt Hilsmentioning

confidence: 99%

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Applications of Ionic Liquids in the Field of Agriculture: A Review

Wang,

Qin,

Dong

et al. 2023

Agriculture

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This review delves into the diverse applications of ionic liquids (ILs) in modern agriculture, focusing on their pivotal roles in the extraction of natural products and pesticides, as well as their substantial significance in sustainable pesticide delivery systems. The reported extraction methods include ILs and their modified materials as solvents in dispersive liquid–liquid microextraction, solid-phase dispersion, and solid-phase microextraction. The study categorizes ILs according to their utility as herbicides, microbicides, food repellents, and plant growth regulators. This review investigates the use of ILs as plant immunity inducers to elevate the systemic acquired resistance in crops, thereby augmenting their intrinsic ability to defend against plant pathogens. Furthermore, the review explores the application of ILs in pesticide delivery systems, emphasizing their ability to enhance efficacy while promoting environmental sustainability. The biodegradability and toxicity aspects of ILs are also discussed, shedding light on their potential as eco-friendly alternatives in agricultural practices. In conclusion, this comprehensive overview underscores the multifaceted contributions of ILs in agriculture, from efficient extraction methods to the development of innovative and sustainable pesticide delivery systems. As the agricultural landscape evolves towards environmentally conscious practices, the integration of ILs presents a promising avenue for enhancing productivity while minimizing ecological impact. As the agricultural industry seeks innovative and sustainable solutions, the nuanced exploration of ILs in this review highlights their potential to address multiple challenges in modern farming practices.

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Section: Herbicidal Ils (Hils)mentioning

confidence: 99%

Section: Herbicidal Ils (Hils)mentioning

confidence: 99%

Section: Double-salt Hilsmentioning

confidence: 99%

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Applications of Ionic Liquids in the Field of Agriculture: A Review

Wang,

Qin,

Dong

et al. 2023

Agriculture

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“…16 HILs have been shown to integrate combinations of different herbicides into a single molecule, enhance herbicidal efficacy, and reduce the risk of weed resistance; this single compound exhibits various modes of action because it contains several herbicidal anions with different mechanisms of action. 17,18 To obtain new herbicides based on amino acids [L-proline (Pro), L-arginine (Arg), and L-histidine (His)] and selected phenoxyacetic acids [(4-chlor-2-methylphenoxy)acetic acid (MCPA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], the synthesis conditions had to be selected, and the resulting structures had to be analyzed in detail. The materials prepared were comprehensively characterized and tested with an emphasis on their structure and biocompatibility.…”

Section: ■ Introductionmentioning

confidence: 99%

“…HILs are known to contain one herbicide in an anionic form and a second herbicide that is incorporated into the cation structure . HILs have been shown to integrate combinations of different herbicides into a single molecule, enhance herbicidal efficacy, and reduce the risk of weed resistance; this single compound exhibits various modes of action because it contains several herbicidal anions with different mechanisms of action. , …”

Section: Introductionmentioning

confidence: 99%

Bioinspired Herbicides–Ionic Liquids or Liquid Cocrystals?

Pernak,

Łożyński,

Kaczmarek

et al. 2024

J. Agric. Food Chem.

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This research provides information about combinations of several amino acids, including L-proline (Pro), L-arginine (Arg), and L-histidine (His), with phenoxyacetic acid herbicides (MCPA and 2,4-D). Five amino acid ionic liquids (AAILs), one amino acid higher-melting salt (AAHMS), and two amino acid liquid cocrystals (AALCs) were obtained in high yields (>90%). The ionization of the six new structures was confirmed by NMR, IR, and molecular modeling. X-ray crystallography was used to definitively confirm the binding location of the mobile hydrogen. Furthermore, we propose a computational method for estimating the energy of specific hydrogen bond(s) in AAIL crystals based on the NBO and QTAIM hydrogen bond parameters obtained by model calculations. An in-depth analysis of the structures allowed to answer the question posed in the title, ionic liquids or liquid cocrystals? AAILs based on arginine and histidine were obtained. In contrast, combining proline with MCPA and 2,4-D led to AALCs. Finally, the compounds were analyzed to measure their herbicidal activity. These studies proved that the novel form of MCPA or 2,4-D improved its ability to control weeds compared to commercial formulations containing the same active ingredients.

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Comparative analysis of bacterial populations in sulfonylurea-sensitive and -resistant weeds: insights into community composition and catabolic gene dynamics

Homa,

Wilms,

Marcinkowska

et al. 2024

Environ Sci Pollut Res

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This study aimed to compare the impact of iodosulfuron-methyl-sodium and an iodosulfuron-based herbicidal ionic liquid (HIL) on the microbiomes constituting the epiphytes and endophytes of cornflower (Centaurea cyanus L.). The experiment involved biotypes of cornflower susceptible and resistant to acetolactate synthase inhibition, examining potential bacterial involvement in sulfonylurea herbicide detoxification. We focused on microbial communities present on the surface and in the plant tissues of roots and shoots. The research included the synthesis and physicochemical analysis of a novel HIL, evaluation of shifts in bacterial community composition, analysis of the presence of catabolic genes associated with sulfonylurea herbicide degradation and determination of their abundance in all experimental variants. Overall, for the susceptible biotype, the biodiversity of the root microbiome was higher compared to shoot microbiome; however, both decreased notably after herbicide or HIL applications. The herbicide-resistant biotype showed lower degree of biodiversity changes, but shifts in community composition occurred, particularly in case of HIL treatment. Graphical Abstract

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Herbicidal ionic liquids containing double or triple anions as a new potential tool for weed control including herbicide-resistant biotypes

Cited by 3 publications

References 35 publications

Applications of Ionic Liquids in the Field of Agriculture: A Review

Applications of Ionic Liquids in the Field of Agriculture: A Review

Bioinspired Herbicides–Ionic Liquids or Liquid Cocrystals?

Comparative analysis of bacterial populations in sulfonylurea-sensitive and -resistant weeds: insights into community composition and catabolic gene dynamics

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