Structural elucidation of metolachlor photoproducts by liquid chromatography/high-resolution tandem mass spectrometry

Nicol, Édith; Genty, Christophe; Bouchonnet, Stéphane; Bourcier, Sophie

doi:10.1002/rcm.7382

Cited by 8 publications

(4 citation statements)

References 22 publications

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“…Metolachlor belongs to the chloroacetanilide herbicides, which are very common to find when analyzing water samples. This herbicide was banned in 2006 [54]; when introduced to the market, it was sold as a product containing the enantiomer pair (R and S). It was developed for the control of grasses and weeds and is recorded to have been used on at least 70 crops [58].…”

Section: Slightly Hazardous Pesticidesmentioning

confidence: 99%

Microbiology and Biochemistry of Pesticides Biodegradation

Guerrero Ramírez,

Ibarra Muñoz,

Balagurusamy

et al. 2023

IJMS

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Pesticides are chemicals used in agriculture, forestry, and, to some extent, public health. As effective as they can be, due to the limited biodegradability and toxicity of some of them, they can also have negative environmental and health impacts. Pesticide biodegradation is important because it can help mitigate the negative effects of pesticides. Many types of microorganisms, including bacteria, fungi, and algae, can degrade pesticides; microorganisms are able to bioremediate pesticides using diverse metabolic pathways where enzymatic degradation plays a crucial role in achieving chemical transformation of the pesticides. The growing concern about the environmental and health impacts of pesticides is pushing the industry of these products to develop more sustainable alternatives, such as high biodegradable chemicals. The degradative properties of microorganisms could be fully exploited using the advances in genetic engineering and biotechnology, paving the way for more effective bioremediation strategies, new technologies, and novel applications. The purpose of the current review is to discuss the microorganisms that have demonstrated their capacity to degrade pesticides and those categorized by the World Health Organization as important for the impact they may have on human health. A comprehensive list of microorganisms is presented, and some metabolic pathways and enzymes for pesticide degradation and the genetics behind this process are discussed. Due to the high number of microorganisms known to be capable of degrading pesticides and the low number of metabolic pathways that are fully described for this purpose, more research must be conducted in this field, and more enzymes and genes are yet to be discovered with the possibility of finding more efficient metabolic pathways for pesticide biodegradation.

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Section: Slightly Hazardous Pesticidesmentioning

confidence: 99%

Microbiology and Biochemistry of Pesticides Biodegradation

Guerrero Ramírez,

Ibarra Muñoz,

Balagurusamy

et al. 2023

IJMS

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“…Non-biological photodecomposition and oxidation of MC, on the other side, lead to many species which have been also identified in surface waters [5][6][7][8][9][10][11][12][13][14][15][16]. Given its possible high environmental impact due to its extended use, numerous experimental studies have been performed on the photocatalytic oxidation under diverse environmental conditions, examining the nature and toxicity of the photoproducts [17,[18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33]. It is well established that sunlight irradiation causes the cleavage of the C-Cl bond.…”

Section: Introductionmentioning

confidence: 99%

Kinetics and thermodynamics of the hydroxylation products in the photodegradation of the herbicide Metolachlor

Salta

Kosmas

Ventura

2020

Pure and Applied Chemistry

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Electronic structure calculations have been performed to determine the thermochemistry and kinetics of the reaction between OH and the radicals of the S enantiomer of the herbicide Metolachlor, 2-chloro-N-(2-methyl-6-ethylphenyl)-N(2-methoxy-1-methylethyl) acetamide (MC), produced by photoinduced breaking of the C–Cl bond. Both density functional and ab initio composite methods were employed to calculate the structure of reactants, intermediates, transition states and products, in gas phase and in aqueous solution. The expected relative abundance of each product was calculated and compared to the experimentally observed concentrations. It is shown that a combination of thermodynamic and kinetic characteristics interplay to produce the expected theoretical abundances, which turn out to be in agreement with the experimentally observed distribution of products.

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“…The most basic interpretation of mass spectral data compares neutral mass losses to the parent ion, to build up the molecule by deduction. 22 This method works well for small compounds, but as the molecules grow larger, the number of variations with similar structures becomes too vast to isolate a single compound by chromatography. Thus, most commonly, fragmentation spectra are compared to a spectral library for known compounds.…”

Section: ■ Introductionmentioning

confidence: 99%

Omics Forecasting: Predictive Calculations Permit the Rapid Interpretation of High-Resolution Mass Spectral Data from Complex Mixtures

Cave

Parker

Lebrilla

et al. 2019

J. Agric. Food Chem.

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For some complex mixtures, chromatographic techniques are insufficient to separate the large numbers of compounds present. In addition, these mixtures often contain compounds with similar or identical molecular masses and shared fragmentation transitions. Advancements in mass spectrometry have provided more and more detailed molecular profiles with significant increases in resolution. This has led to a capacity to distinguish a very large number of compounds in complex mixtures, providing overwhelming data sets. The approach of calculating molecular formulas from a mass list has become more and more problematic as the number of signals has increased exponentially, to the point that it has become impossible to manually interpret the thousands of mass signals. The current approach is to calculate a list of possible formulas that fall within a specific mass error of the observed signal. Then, one must look for possible structures that can be derived from each entry on the list of formulas. However, an alternative approach is to anticipate the possible structures of a particular set of compounds, such as red wine pigments, and then compare the ion signals against a predicted list. To that end, starting with known wine pigment types, we have generated a set of expected wine pigment variants based on known derivatives of condensed tannin oligomers, anthocyanins, and fermentation products. After the ability to distinguish compounds by mass spectrometry was accounted for, over 1 million results were generated consisting of known and anticipated wine pigments. A comparison with a small sample of wine phenolic fractions show a large number of matches, suggesting that this approach may be helpful.

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Structural elucidation of metolachlor photoproducts by liquid chromatography/high-resolution tandem mass spectrometry

Cited by 8 publications

References 22 publications

Microbiology and Biochemistry of Pesticides Biodegradation

Microbiology and Biochemistry of Pesticides Biodegradation

Kinetics and thermodynamics of the hydroxylation products in the photodegradation of the herbicide Metolachlor

Omics Forecasting: Predictive Calculations Permit the Rapid Interpretation of High-Resolution Mass Spectral Data from Complex Mixtures

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