Degradation studies of dimethachlor in soils and water by UHPLC‐HRMS: putative elucidation of unknown metabolites

López‐Ruiz, Rosalía; Romero‐González, Roberto; Ortega‐Carrasco, Elisabeth; Vidal, José Luis Martı́nez; Frenich, Antonia Garrido

doi:10.1002/ps.5570

Cited by 6 publications

(8 citation statements)

References 29 publications

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“…In this study, the use of MassChemSite and WebChembase software is described for the first time as a tool for the analysis of forced degradation products. Previously, MassChemSite proved to be a valuable tool to assist late-stage functionalization (LSF) through C–H functionalization of a drug during the drug discovery process and in the elucidation of new plant metabolites. − Indeed, as a case study, MassChemSite software was applied for the data processing of the forced degradation of lansoprazole (a proton-pump inhibitor used to treat stomach and intestinal ulcers, erosive esophagitis, and Zollinger–Ellison syndrome), monitored in the following experimental conditions: acidic hydrolysis, basic hydrolysis, neutral hydrolysis, and oxidation. Later, WebChembase was employed to perform the data analysis.…”

Section: Introductionmentioning

confidence: 99%

Automatic Identification of Lansoprazole Degradants under Stress Conditions by LC-HRMS with MassChemSite and WebChembase

Bonciarelli

Desantis

Goracci

et al. 2021

J. Chem. Inf. Model.

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Stress testing is one of the most important parts of the drug development process, helping to foresee stability problems and to identify degradation products. One of the processes involving stress testing is represented by forced degradation studies, which can predict the impact of certain conditions of pH, moisture, heat, or other negative effects due to transportation or packaging issues on drug potency and purity, ensuring patient safety. Regulatory agencies have been working on a standardization of laboratory procedures since the past two decades. One of the results of those years of intensive research is the International Conference on Harmonization (ICH) guidelines, which clearly define which forced degradation studies should be performed on new drugs, which become a routine work in pharmaceutical laboratories. Since used techniques based on high-performance liquid chromatography coupled with high-resolution mass spectrometry have been developed years ago and are now mastered by pharmaceutical scientists, automation of data analysis, and thus data processing, is becoming a hot topic nowadays. In this work, we present MassChemSite and WebChembase as a tandem to automatize the routine analysis studies without missing information quality, using as a case study the degradation of lansoprazole under acidic, oxidative, basic, and neutral stress conditions.

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Section: Introductionmentioning

confidence: 99%

Automatic Identification of Lansoprazole Degradants under Stress Conditions by LC-HRMS with MassChemSite and WebChembase

Bonciarelli

Desantis

Goracci

et al. 2021

J. Chem. Inf. Model.

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“…The current European Union (EU) guidelines indicate that one plant metabolite (SYN 500003) of mandipropamid is more acutely toxic than mandipropamid (JMPR, 2008), but the confirmation of its metabolites in Chinese soil has not been documented. In addition, the identification of metabolites has often been delineated using radiolabeling (JMPR, 2008), liquid chromatography with mass spectrometry (LC-MS) (Gupta et al, 2012), and liquid chromatography with high-resolution mass spectrometry (LC-HRMS) (López-Ruiz et al, 2020). Among these techniques, LC-HRMS is the most accurate and reliable technique for the determination of a parent chemical and its metabolites because of its excellent identification capacity for known and unknown compounds (Coscollà et al, 2014;EFSA, 2012;Gómez-Pérez et al, 2014;López-Ruiz et al, 2017, 2020.…”

Section: Core Ideasmentioning

confidence: 99%

“…Among these techniques, LC-HRMS is the most accurate and reliable technique for the determination of a parent chemical and its metabolites because of its excellent identification capacity for known and unknown compounds (Coscollà et al, 2014;EFSA, 2012;Gómez-Pérez et al, 2014;López-Ruiz et al, 2017, 2020. For example, López-Ruiz et al (2020) not only monitored several known metabolites but also identified three new metabolites of dimethachlor in soil by ultra-high-performance liquid chromatography with highresolution mass spectrometry (UHPLC-HRMS). Therefore, the determination of metabolites of mandipropamid in Chinese soil using LC-HRMS is necessary.…”

Section: Core Ideasmentioning

confidence: 99%

“…For example, López‐Ruiz et al. (2020) not only monitored several known metabolites but also identified three new metabolites of dimethachlor in soil by ultra‐high‐performance liquid chromatography with high‐resolution mass spectrometry (UHPLC–HRMS). Therefore, the determination of metabolites of mandipropamid in Chinese soil using LC–HRMS is necessary.…”

Section: Introductionmentioning

confidence: 99%

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Enantioselective environmental behavior of the chiral fungicide mandipropamid in four types of Chinese soil

Han

Chen

Liu

et al. 2021

Soil Science Soc of Amer J

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Enantioselective degradation behavior of mandipropamid, and factors affecting its degradation and metabolites in four types of Chinese soil were investigated in this work. The results showed that the enantiomeric selectivity values ranged from 0.025 to 0.170, indicating that enantioselectivity was found in the degradation process of the racemate in all of the soil samples and that the R-(−)-enantiomer was preferentially degraded. The degradation compounds formed faster in native alkaline soils (half-lives = 35.5-39.80 d) than in native acidic soils (half-lives = 51.3-77.90 d). The half-lives of the R-(−)-enantiomer and S-(+)-enantiomer were 35.5-73.7 and 37.5-77.9 d, 66.6-97.6 and 70.0-103.5 d, and 52.5-110.0 and 66.0-144.4 d in the fourtypes of soil under native, sterilized, and organic matter-removed conditions, respectively, which indicated that mandipropamid degradation can be attributed to microbial activity and the organic matter content in the soil. Furthermore, the half-lives of the R-(−)-enantiomer and S-(+)-enantiomer decreased 1.07-1.95 and 1.08-1.79 times with each 10˚C increase in incubation temperature, and the half-lives of the R-(−)-enantiomer and S-(+)-enantiomer decreased 1.09-1.43 and 1.06-1.50 times with increasing moisture content. However, the incubation temperature and soil moisture did not change the enantioselectivity. Mandipropamid enantiomers were observed to be configurationally stable in the selected soil, and no interconversion was found during the incubation of enantiopure R-(−)-mandipropamid or S-(+)-mandipropamid in native or sterilized soil. During the degradation process, four major metabolites were detected. In comprehensive consideration of the environmental behavior, the enantioselective degradation results should be considered to more accurately assess the risk of this chiral pesticide in a real environment.

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“…The half-life of dimethachlor in soil is between 2 and 16 days 11 . However, in specific soil type and conditions half-life may be longer than 50 days 12 . Its effect on soil microorganisms is less studied in comparison with other chloroacetamide herbicides such as metolachlor or acetochlor.…”

Section: Introductionmentioning

confidence: 99%

Changes in soil microbial community and activity caused by application of dimethachlor and linuron

Medo

Maková

Medová

et al. 2021

Sci Rep

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Soil microorganisms and their activities are essential for maintaining soil health and fertility. Microorganisms can be negatively affected by application of herbicides. Although effects of herbicides on microorganisms are widely studied, there is a lack of information for chloroacetamide herbicide dimethachlor. Thus, dimethachlor and well known linuron were applied to silty-loam luvisol and their effects on microorganisms were evaluated during112 days long laboratory assay. Dimethachlor and linuron were applied in doses 1.0 kg ha−1 and 0.8 kg ha−1 corresponding to 3.33 mg kg−1 and 2.66 mg kg−1 respectively. Also 100-fold doses were used for magnification of impacts. Linuron in 100-fold dose caused minor increase of respiration, temporal increase of soil microbial biomass, decrease of soil dehydrogenase activity, and altered microbial community. Dimethachlor in 100-fold dose significantly increased respiration; microbial biomass and decreased soil enzymatic activities. Microbial composition changed significantly, Proteobacteria abundance, particularly Pseudomonas and Achromobacter genera increased from 7 to 28th day. In-silico prediction of microbial gene expression by PICRUSt2 software revealed increased expression of genes related to xenobiotic degradation pathways. Evaluated characteristics of microbial community and activity were not affected by herbicides in recommended doses and the responsible use of both herbicides will not harm soil microbial community.

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Degradation studies of dimethachlor in soils and water by UHPLC‐HRMS: putative elucidation of unknown metabolites

Cited by 6 publications

References 29 publications

Automatic Identification of Lansoprazole Degradants under Stress Conditions by LC-HRMS with MassChemSite and WebChembase

Automatic Identification of Lansoprazole Degradants under Stress Conditions by LC-HRMS with MassChemSite and WebChembase

Enantioselective environmental behavior of the chiral fungicide mandipropamid in four types of Chinese soil

Changes in soil microbial community and activity caused by application of dimethachlor and linuron

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