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Registro Completo |
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Biblioteca(s): |
Embrapa Instrumentação. |
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Data corrente: |
05/07/2023 |
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Data da última atualização: |
05/07/2023 |
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Tipo da produção científica: |
Artigo em Periódico Indexado |
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Autoria: |
RAMOS, B.; VAZ, W. F.; DINIZ, L. F.; SANCHES NETO, F. O.; RIBEIRO, J. C. O.; CARVALHO-SILVA, V. H.; TEIXEIRA, A. C. S. C.; RIBEIRO, C.; NAPOLITANO, H. B.; CARVALHO JR, P. S. |
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Afiliação: |
CAUE RIBEIRO DE OLIVEIRA, CNPDIA. |
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Título: |
Kinetics, mechanism, and tautomerism in ametryn acid hydrolysis: From molecular structure to environmental impacts. |
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Ano de publicação: |
2023 |
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Fonte/Imprenta: |
Chemosphere, v. 324, 138278, 2023. |
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Páginas: |
1 - 10 |
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ISSN: |
0045-6535 |
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DOI: |
https://doi.org/10.1016/j.chemosphere.2023.138278 |
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Idioma: |
Inglês |
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Conteúdo: |
The excessive use of pesticides and the demand for environmentally friendly compounds have driven the focus to detailed studies of the environmental destination of these compounds. Degradation by hydrolysis of pesticides, when released into the soil, can result in the formation of metabolites with potentially adverse effects on the environment. Moving in this direction, we investigated the mechanism of acid hydrolysis of the herbicide ametryn (AMT) and predicted the toxicities of metabolites through experimental and theoretical approaches. The formation of ionized hydroxyatrazine (HA) occurs with the release of the SCH3- group and the addition of H3O+ to the triazine ring. The tautomerization reactions privileged the conversion of AMT into HA. Furthermore, the ionized HA is stabilized by an intramolecular reaction that provides the molecule in two tautomeric states. Experimentally, the hydrolysis of AMT was obtained under acidic conditions and at room temperature with HA as the main product. HA was isolated in a solid state through its crystallization as organic counterions. The mechanism of conversion of AMT to HA and the experimental investigation of the reaction kinetics allowed us to determine the dissociation of CH3SH as the rate-controlling step in the degradation process that culminates in a half-life between 7 and 24 months under typical acid soil conditions of the Brazilian Midwest ? region with strong agricultural and livestock vocation. The keto and hydroxy metabolites showed substantial thermodynamic stability and a decrease in toxicity compared to AMT. We hope that this comprehensive study will support the understanding of the degradation of s-triazine-based pesticides. MenosThe excessive use of pesticides and the demand for environmentally friendly compounds have driven the focus to detailed studies of the environmental destination of these compounds. Degradation by hydrolysis of pesticides, when released into the soil, can result in the formation of metabolites with potentially adverse effects on the environment. Moving in this direction, we investigated the mechanism of acid hydrolysis of the herbicide ametryn (AMT) and predicted the toxicities of metabolites through experimental and theoretical approaches. The formation of ionized hydroxyatrazine (HA) occurs with the release of the SCH3- group and the addition of H3O+ to the triazine ring. The tautomerization reactions privileged the conversion of AMT into HA. Furthermore, the ionized HA is stabilized by an intramolecular reaction that provides the molecule in two tautomeric states. Experimentally, the hydrolysis of AMT was obtained under acidic conditions and at room temperature with HA as the main product. HA was isolated in a solid state through its crystallization as organic counterions. The mechanism of conversion of AMT to HA and the experimental investigation of the reaction kinetics allowed us to determine the dissociation of CH3SH as the rate-controlling step in the degradation process that culminates in a half-life between 7 and 24 months under typical acid soil conditions of the Brazilian Midwest ? region with strong agricultural and livestock vocation. The keto and hydroxy metabo... Mostrar Tudo |
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Palavras-Chave: |
Conversion of AMT in HA; DFT. |
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Categoria do assunto: |
-- |
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Marc: |
LEADER 02582naa a2200289 a 4500
001 2154804
005 2023-07-05
008 2023 bl uuuu u00u1 u #d
022 $a0045-6535
024 7 $ahttps://doi.org/10.1016/j.chemosphere.2023.138278$2DOI
100 1 $aRAMOS, B.
245 $aKinetics, mechanism, and tautomerism in ametryn acid hydrolysis$bFrom molecular structure to environmental impacts.$h[electronic resource]
260 $c2023
300 $a1 - 10
520 $aThe excessive use of pesticides and the demand for environmentally friendly compounds have driven the focus to detailed studies of the environmental destination of these compounds. Degradation by hydrolysis of pesticides, when released into the soil, can result in the formation of metabolites with potentially adverse effects on the environment. Moving in this direction, we investigated the mechanism of acid hydrolysis of the herbicide ametryn (AMT) and predicted the toxicities of metabolites through experimental and theoretical approaches. The formation of ionized hydroxyatrazine (HA) occurs with the release of the SCH3- group and the addition of H3O+ to the triazine ring. The tautomerization reactions privileged the conversion of AMT into HA. Furthermore, the ionized HA is stabilized by an intramolecular reaction that provides the molecule in two tautomeric states. Experimentally, the hydrolysis of AMT was obtained under acidic conditions and at room temperature with HA as the main product. HA was isolated in a solid state through its crystallization as organic counterions. The mechanism of conversion of AMT to HA and the experimental investigation of the reaction kinetics allowed us to determine the dissociation of CH3SH as the rate-controlling step in the degradation process that culminates in a half-life between 7 and 24 months under typical acid soil conditions of the Brazilian Midwest ? region with strong agricultural and livestock vocation. The keto and hydroxy metabolites showed substantial thermodynamic stability and a decrease in toxicity compared to AMT. We hope that this comprehensive study will support the understanding of the degradation of s-triazine-based pesticides.
653 $aConversion of AMT in HA
653 $aDFT
700 1 $aVAZ, W. F.
700 1 $aDINIZ, L. F.
700 1 $aSANCHES NETO, F. O.
700 1 $aRIBEIRO, J. C. O.
700 1 $aCARVALHO-SILVA, V. H.
700 1 $aTEIXEIRA, A. C. S. C.
700 1 $aRIBEIRO, C.
700 1 $aNAPOLITANO, H. B.
700 1 $aCARVALHO JR, P. S.
773 $tChemosphere$gv. 324, 138278, 2023.
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| 2. |  | RAMOS, B.; VAZ, W. F.; DINIZ, L. F.; SANCHES NETO, F. O.; RIBEIRO, J. C. O.; CARVALHO-SILVA, V. H.; TEIXEIRA, A. C. S. C.; RIBEIRO, C.; NAPOLITANO, H. B.; CARVALHO JR, P. S. Kinetics, mechanism, and tautomerism in ametryn acid hydrolysis: From molecular structure to environmental impacts. Chemosphere, v. 324, 138278, 2023. 1 - 10| Tipo: Artigo em Periódico Indexado | Circulação/Nível: A - 1 |
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