Unveiling the photodegradation of tralkoxydim herbicide and its formulation in natural waters: Structural elucidation of transformation products and toxicity assessment

Pesticide degradation products (DPs), as emerging contaminants, are being detected in aquatic environments due to the widespread use of their active substances and pose potential risks to aquatic ecology and human health. However, their identification is challenging due to the many environmental con...

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Autores: Patiño-Ropero, María José, Nieto-Carmona, Juan Carlos, Cobos Escudero, María, Lamsabhi, Al Mokhtar, Alcamí, Manuel, Alonso-Prados, José Luis, Sandín España, Pilar
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2025
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/399203
Acceso en línea:http://hdl.handle.net/10261/399203
https://api.elsevier.com/content/abstract/scopus_id/105006528162
Access Level:acceso abierto
Palabra clave:Degradation products
In silico
Pesticide
QTOF-MS
Vibrio fischeri
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spelling Unveiling the photodegradation of tralkoxydim herbicide and its formulation in natural waters: Structural elucidation of transformation products and toxicity assessmentPatiño-Ropero, María JoséNieto-Carmona, Juan CarlosCobos Escudero, MaríaLamsabhi, Al MokhtarAlcamí, ManuelAlonso-Prados, José LuisSandín España, PilarDegradation productsIn silicoPesticideQTOF-MSVibrio fischeriPesticide degradation products (DPs), as emerging contaminants, are being detected in aquatic environments due to the widespread use of their active substances and pose potential risks to aquatic ecology and human health. However, their identification is challenging due to the many environmental conditions that influence their degradation processes. The photodegradation of the herbicide tralkoxydim and its formulation has been studied in ultrapure, spring and river waters and has shown rapid degradation. The photodegradation of tralkoxydim was slower in natural water and in the presence of humic acids (HA) than in ultrapure water, with half-lives of 5.1 h for river water and 1.1 h for ultrapure water. For the first time, three degradation products were identified in aquatic media using HPLC-TOF-MS/MS. These include photoisomerization, photolysis of the N-O bond of the oxime resulting in the tralkoxydim imine (major DP), and cyclization leading to tralkoxydim oxazole. Quantitative structure-activity relationship (QSAR) models were employed to approximate the potential ecotoxicological and environmental impacts of tralkoxydim and its DPs. Additionally, the toxicity of the isolated DPs was evaluated using a standard microtest bioassay with Vibrio fischeri bacteria. The results show that tralkoxydim imine and tralkoxydim oxazole exhibit high toxicity.This work has been supported by the project PRIES-CM-Y2020/EMT-6290: “Expert system for risk identification of emerging pollutants from pesticides” financed by the Comunidad de Madrid and project PID2022–139874OR-C21 of the Ministerio de Ciencia e Innovación, Spain.Peer reviewedElsevier BVComunidad de MadridAgencia Nacional de Promoción Científica y Tecnológica (Argentina)Ministerio de Ciencia e Innovación (España)Lamsabhi, Al Mokhtar [0000-0002-1509-2513]Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202520252025info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionapplication/pdfhttp://hdl.handle.net/10261/399203https://api.elsevier.com/content/abstract/scopus_id/105006528162reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE#Y2020/EMT-6290/PRIES-CMinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2022-139874OR-C21The underlying dataset has been published as supplementary material of the article in the publisher platform at DOI https://doi.org/10.1016/j.ecoenv.2025.118409https://doi.org/10.1016/j.ecoenv.2025.118409Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/3992032026-05-22T06:33:51Z
dc.title.none.fl_str_mv Unveiling the photodegradation of tralkoxydim herbicide and its formulation in natural waters: Structural elucidation of transformation products and toxicity assessment
title Unveiling the photodegradation of tralkoxydim herbicide and its formulation in natural waters: Structural elucidation of transformation products and toxicity assessment
spellingShingle Unveiling the photodegradation of tralkoxydim herbicide and its formulation in natural waters: Structural elucidation of transformation products and toxicity assessment
Patiño-Ropero, María José
Degradation products
In silico
Pesticide
QTOF-MS
Vibrio fischeri
title_short Unveiling the photodegradation of tralkoxydim herbicide and its formulation in natural waters: Structural elucidation of transformation products and toxicity assessment
title_full Unveiling the photodegradation of tralkoxydim herbicide and its formulation in natural waters: Structural elucidation of transformation products and toxicity assessment
title_fullStr Unveiling the photodegradation of tralkoxydim herbicide and its formulation in natural waters: Structural elucidation of transformation products and toxicity assessment
title_full_unstemmed Unveiling the photodegradation of tralkoxydim herbicide and its formulation in natural waters: Structural elucidation of transformation products and toxicity assessment
title_sort Unveiling the photodegradation of tralkoxydim herbicide and its formulation in natural waters: Structural elucidation of transformation products and toxicity assessment
dc.creator.none.fl_str_mv Patiño-Ropero, María José
Nieto-Carmona, Juan Carlos
Cobos Escudero, María
Lamsabhi, Al Mokhtar
Alcamí, Manuel
Alonso-Prados, José Luis
Sandín España, Pilar
author Patiño-Ropero, María José
author_facet Patiño-Ropero, María José
Nieto-Carmona, Juan Carlos
Cobos Escudero, María
Lamsabhi, Al Mokhtar
Alcamí, Manuel
Alonso-Prados, José Luis
Sandín España, Pilar
author_role author
author2 Nieto-Carmona, Juan Carlos
Cobos Escudero, María
Lamsabhi, Al Mokhtar
Alcamí, Manuel
Alonso-Prados, José Luis
Sandín España, Pilar
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Comunidad de Madrid
Agencia Nacional de Promoción Científica y Tecnológica (Argentina)
Ministerio de Ciencia e Innovación (España)
Lamsabhi, Al Mokhtar [0000-0002-1509-2513]
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Degradation products
In silico
Pesticide
QTOF-MS
Vibrio fischeri
topic Degradation products
In silico
Pesticide
QTOF-MS
Vibrio fischeri
description Pesticide degradation products (DPs), as emerging contaminants, are being detected in aquatic environments due to the widespread use of their active substances and pose potential risks to aquatic ecology and human health. However, their identification is challenging due to the many environmental conditions that influence their degradation processes. The photodegradation of the herbicide tralkoxydim and its formulation has been studied in ultrapure, spring and river waters and has shown rapid degradation. The photodegradation of tralkoxydim was slower in natural water and in the presence of humic acids (HA) than in ultrapure water, with half-lives of 5.1 h for river water and 1.1 h for ultrapure water. For the first time, three degradation products were identified in aquatic media using HPLC-TOF-MS/MS. These include photoisomerization, photolysis of the N-O bond of the oxime resulting in the tralkoxydim imine (major DP), and cyclization leading to tralkoxydim oxazole. Quantitative structure-activity relationship (QSAR) models were employed to approximate the potential ecotoxicological and environmental impacts of tralkoxydim and its DPs. Additionally, the toxicity of the isolated DPs was evaluated using a standard microtest bioassay with Vibrio fischeri bacteria. The results show that tralkoxydim imine and tralkoxydim oxazole exhibit high toxicity.
publishDate 2025
dc.date.none.fl_str_mv 2025
2025
2025
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Publisher's version
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/399203
https://api.elsevier.com/content/abstract/scopus_id/105006528162
url http://hdl.handle.net/10261/399203
https://api.elsevier.com/content/abstract/scopus_id/105006528162
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
Y2020/EMT-6290/PRIES-CM
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2022-139874OR-C21
The underlying dataset has been published as supplementary material of the article in the publisher platform at DOI https://doi.org/10.1016/j.ecoenv.2025.118409
https://doi.org/10.1016/j.ecoenv.2025.118409
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Elsevier BV
publisher.none.fl_str_mv Elsevier BV
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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