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Iodosulfuron-Methyl-Based Herbicidal Ionic Liquids Comprising Alkyl Betainate Cation as Novel Active Ingredients with Reduced Environmental Impact and Excellent Efficacy.

ABSTRACT: A new family of bio-based herbicidal ionic liquids (HILs) has been synthesized starting from the renewable resource glycine betaine (a derivative of natural amino acids). After esterification, the obtained alkyl betainate bromides containing straight alkyl chains varying from ethyl to octadecyl were combined with a herbicidal anion from the sulfonylurea group (iodosulfuron-methyl). The melting points of the iodosulfuron-methyl-based salts were in a range from 51 to 99 °C, which allows their classification as ionic liquids (ILs). In addition, the new HILs exhibited good affinity for polar and semipolar organic solvents, such as DMSO, methanol, acetonitrile, acetone, and chloroform, while the presence of bulky organic cations reduced their solubility in water. The synthesized products turned out to be stable during storage at 25 °C for over 6 months; however, at 75 °C they underwent fast, progressive degradation and released volatile byproducts. The values of the logarithm of the octanol-water partition coefficient of ILs with alkyls longer than hexyl occurred in the "safe zone" (between 0 and 3); hence, the risk of their migration into groundwater after application or the possibility of their bioaccumulation in the environment is lower in comparison with the currently available commercial form (iodosulfuron-methyl sodium salt). Greenhouse studies confirmed a very high herbicidal efficacy for the obtained salts toward tested plants of oilseed rape, indicating that they may become an attractive replacement for the currently available sulfonylurea-based formulations.

SUBMITTER: Niemczak M

PROVIDER: S-EPMC7705962 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Iodosulfuron-Methyl-Based Herbicidal Ionic Liquids Comprising Alkyl Betainate Cation as Novel Active Ingredients with Reduced Environmental Impact and Excellent Efficacy.

Niemczak Michał M Sobiech Łukasz Ł Grzanka Monika M

Journal of agricultural and food chemistry 20201110 47

A new family of bio-based herbicidal ionic liquids (HILs) has been synthesized starting from the renewable resource glycine betaine (a derivative of natural amino acids). After esterification, the obtained alkyl betainate bromides containing straight alkyl chains varying from ethyl to octadecyl were combined with a herbicidal anion from the sulfonylurea group (iodosulfuron-methyl). The melting points of the iodosulfuron-methyl-based salts were in a range from 51 to 99 °C, which allows their clas ...[more]

PMID: 33170680

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Project description:The aim of the study was to evaluate the effect of herbicidal ionic liquids on the population changes of microorganisms used in a batch anaerobic digester. The influence of the following ionic liquids: benzalkonium (2,4-dichlorophenoxy)acetate (BA)(2,4-D), benzalkonium (4-chloro-2-methylphenoxy)acetate (BA)(MCPA), didecyldimethylammonium (2,4-dichlorophenoxy)acetate (DDA)(2,4-D), didecyldimethylammonium (4-chloro-2-methylphenoxy)acetate (DDA)(MCPA), as well as reference herbicides (4-chloro-2-methylphenoxy)acetic acid (MCPA) and (2,4-dichlorophenoxy)acetic acid (2,4-D) in the form of sodium salts on biogas production efficiency was investigated. The effective concentration (EC50) values were determined for all tested compounds. (MCPA)- was the most toxic, with an EC50 value of 38.6⁻41.2 mg/L. The EC50 for 2,4-D was 55.7⁻59.8 mg/L. The addition of the test substances resulted in changes of the population structure of the microbiota which formed the fermentation pulp. The research was based on 16S rDNA analysis with the use of the Next Generation Sequencing method and the MiSeq platform (Illumina, San Diego, CA, USA). There was a significant decrease in bacteria belonging to Firmicutes and Archaea belonging to Euryarchaeota. A significant decrease of the biodiversity of the methane fermentation microbiota was also established, which was expressed by the decrease of the operational taxonomic units (OTUs) and the value of Shannon's entropy. In order to determine the functional potential of bacterial metapopulations based on the 16SrDNAprofile, the PICRUSt(Phylogenetic Investigation of Communities by Reconstruction of Unobserved States)tool was used, which allowed to determine the gene potency of microorganisms and their ability to biodegrade the herbicides. In the framework of the conducted analysis, no key genes related to the biodegradation of MCPA or 2,4-D were found, and the observed decrease of their content in the supernatant liquid was caused by their sorption on bacterial biomass.

Project description:A comprehensive study on the phase behaviour of two sets of ionic liquids (ILs) and their interactions with water is here presented through combining experimental and theoretical approaches. The impact of the alkyl side chain length and the cation symmetry on the water solubility in the asymmetric [C N-1C1im][NTf2] and symmetric [C N-1C N-1im][NTf2] series of ILs (N up to 22), from 288.15 K to 318.15 K and at atmospheric pressure, was studied. The experimental data reveal that the solubility of water in ILs with an asymmetric cation is higher than in those with the symmetric isomer. Several trend shifts on the water solubility as a function of the alkyl side chain length were identified, namely at [C6C1im][NTf2] for asymmetric ILs and at [C4C4im][NTf2] and [C7C7im][NTf2] for the symmetric ILs. To complement the experimental data and to further investigate the molecular-level mechanisms behind the dissolution process, Density Functional Theory calculations, using the Conductor-like Screening Model for Real Solvents (COSMO-RS) and the Electrostatic potential-derived CHelpG, were performed. The COSMO-RS model is able to qualitatively predict water solubility as function of temperature and alkyl chain lengths of both symmetric and asymmetric cations. Furthermore, the model is also capable to predict the somewhat higher water solubility in the asymmetric cation, as well as the trend shift as function of alkyl chain lengths experimentally observed. Both COSMO-RS and the electrostatic potential-derived CHelpG show that the interactions of water and the IL cation take place on the IL polar region, namely on the aromatic head and adjacent methylene groups what explains the differences in water solubility observed for cations with different chain lengths. Furthermore, the CHelpG calculations for the isolated cations in the gas phase indicates that the trend shift of water solubility as function of alkyl chain lengths and the difference of water solubility in symmetric may also result from the partial positive charge distribution/contribution of the cation.

Dataset Information

Iodosulfuron-Methyl-Based Herbicidal Ionic Liquids Comprising Alkyl Betainate Cation as Novel Active Ingredients with Reduced Environmental Impact and Excellent Efficacy.

Publications

Iodosulfuron-Methyl-Based Herbicidal Ionic Liquids Comprising Alkyl Betainate Cation as Novel Active Ingredients with Reduced Environmental Impact and Excellent Efficacy.

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