Profoxydim in Focus: A Structural Examination of Herbicide Behavior in Gas and Aqueous Phases

This study investigates the chemical structure of profoxydim, focusing on its E–isomer, the main commercial form. The research aimed to determine the predominant tautomeric forms under various environmental conditions. Using proton and carbon–13 NMR spectroscopy alongside theoretical modeling, we ex...

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Autores: Cobos Escudero, María, Pla, Paula, Cervantes-Díaz, A., Alonso Prados, José Luis, Sandín España, Pilar, Alcamí, M., Lamsabhi, A. M.
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2024
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/369070
Acceso en línea:http://hdl.handle.net/10261/369070
Access Level:acceso abierto
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spelling Profoxydim in Focus: A Structural Examination of Herbicide Behavior in Gas and Aqueous PhasesCobos Escudero, MaríaPla, PaulaCervantes-Díaz, A.Alonso Prados, José LuisSandín España, PilarAlcamí, M.Lamsabhi, A. M.This study investigates the chemical structure of profoxydim, focusing on its E–isomer, the main commercial form. The research aimed to determine the predominant tautomeric forms under various environmental conditions. Using proton and carbon–13 NMR spectroscopy alongside theoretical modeling, we examined tautomers and their conformers in different solvents (MeOD, DMSO, CDCl3, benzene) to mimic gas and aqueous phases. The findings reveal that the enolic form dominates in the gas phase, while the ketonic form prevails in aqueous environments, providing key insights into the herbicide’s environmental behavior. We also observed an isomeric transition from E to Z under acidic conditions, which could affect profoxydim’s reactivity in natural environments. The theoretical calculations indicated that in acidic conditions, the E and Z forms are nearly degenerate, with the E form remaining dominant in neutral environments. Additionally, QSAR models assessed the toxicity of various tautomers, revealing significant differences that could impact bioactivity and environmental fate. This research offers crucial insights into the structural dynamics of profoxydim, contributing to cyclohexanedione chemistry and the development of more effective herbicidesThis research was funded by the projects PID2023–150717NB–I00, PDC2021–121203–I00 and PID2022–139874OR–C21 from Ministerio de Ciencia, Innovacion y Universidades in Spain and the PRIES–CM project Ref: Y2020/EMT–6290 from the Comunidad Autónoma de MadridPeer reviewedMultidisciplinary Digital Publishing InstituteMinisterio de Ciencia, Innovación y Universidades (España)Comunidad de MadridConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]2024202420242024info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionapplication/pdfhttp://hdl.handle.net/10261/369070reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/AEI//PID2023–150717NB–I00info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PDC2021-121203-I00info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2022-139874OR-C21Y2020/EMT-6290/PRIES-CMThe underlying dataset has been published as supplementary material of the article in the publisher platform at DOI https://doi.org/10.3390/molecules29184371https://doi.org/10.3390/molecules29184371Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/3690702026-05-22T06:33:51Z
dc.title.none.fl_str_mv Profoxydim in Focus: A Structural Examination of Herbicide Behavior in Gas and Aqueous Phases
title Profoxydim in Focus: A Structural Examination of Herbicide Behavior in Gas and Aqueous Phases
spellingShingle Profoxydim in Focus: A Structural Examination of Herbicide Behavior in Gas and Aqueous Phases
Cobos Escudero, María
title_short Profoxydim in Focus: A Structural Examination of Herbicide Behavior in Gas and Aqueous Phases
title_full Profoxydim in Focus: A Structural Examination of Herbicide Behavior in Gas and Aqueous Phases
title_fullStr Profoxydim in Focus: A Structural Examination of Herbicide Behavior in Gas and Aqueous Phases
title_full_unstemmed Profoxydim in Focus: A Structural Examination of Herbicide Behavior in Gas and Aqueous Phases
title_sort Profoxydim in Focus: A Structural Examination of Herbicide Behavior in Gas and Aqueous Phases
dc.creator.none.fl_str_mv Cobos Escudero, María
Pla, Paula
Cervantes-Díaz, A.
Alonso Prados, José Luis
Sandín España, Pilar
Alcamí, M.
Lamsabhi, A. M.
author Cobos Escudero, María
author_facet Cobos Escudero, María
Pla, Paula
Cervantes-Díaz, A.
Alonso Prados, José Luis
Sandín España, Pilar
Alcamí, M.
Lamsabhi, A. M.
author_role author
author2 Pla, Paula
Cervantes-Díaz, A.
Alonso Prados, José Luis
Sandín España, Pilar
Alcamí, M.
Lamsabhi, A. M.
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Ciencia, Innovación y Universidades (España)
Comunidad de Madrid
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
description This study investigates the chemical structure of profoxydim, focusing on its E–isomer, the main commercial form. The research aimed to determine the predominant tautomeric forms under various environmental conditions. Using proton and carbon–13 NMR spectroscopy alongside theoretical modeling, we examined tautomers and their conformers in different solvents (MeOD, DMSO, CDCl3, benzene) to mimic gas and aqueous phases. The findings reveal that the enolic form dominates in the gas phase, while the ketonic form prevails in aqueous environments, providing key insights into the herbicide’s environmental behavior. We also observed an isomeric transition from E to Z under acidic conditions, which could affect profoxydim’s reactivity in natural environments. The theoretical calculations indicated that in acidic conditions, the E and Z forms are nearly degenerate, with the E form remaining dominant in neutral environments. Additionally, QSAR models assessed the toxicity of various tautomers, revealing significant differences that could impact bioactivity and environmental fate. This research offers crucial insights into the structural dynamics of profoxydim, contributing to cyclohexanedione chemistry and the development of more effective herbicides
publishDate 2024
dc.date.none.fl_str_mv 2024
2024
2024
2024
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/10261/369070
url http://hdl.handle.net/10261/369070
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#
#PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/AEI//PID2023–150717NB–I00
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PDC2021-121203-I00
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2022-139874OR-C21
Y2020/EMT-6290/PRIES-CM
The underlying dataset has been published as supplementary material of the article in the publisher platform at DOI https://doi.org/10.3390/molecules29184371
https://doi.org/10.3390/molecules29184371
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 Multidisciplinary Digital Publishing Institute
publisher.none.fl_str_mv Multidisciplinary Digital Publishing Institute
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
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