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 | Acesso ao texto completo restrito à biblioteca da Embrapa Instrumentação. Para informações adicionais entre em contato com cnpdia.biblioteca@embrapa.br. |
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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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Embrapa Instrumentação (CNPDIA) |
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Registro Completo
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Biblioteca(s): |
Embrapa Gado de Corte. |
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Data corrente: |
10/07/1998 |
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Data da última atualização: |
10/07/1998 |
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Autoria: |
CHAKRABORTY, S.; PERROT, R.; CHARCHAR, M. J. D`A.; FERNANDES, C. D.; KELEMU, S. |
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Afiliação: |
CSIRO. Tropical Agriculture (Queensland, Australia). |
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Título: |
Biodiversity, epidemiology and virulence of Colletotrichum gloeosporioides. II. Genetic and pathogenic diversity in isolates of Colletotrichum gloeosporioides from eight species of Stylosanthes. |
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Ano de publicação: |
1997 |
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Fonte/Imprenta: |
Tropical Grasslands, Brisbane, v.31, n.5, p.393-401, Nov. 1997. |
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Idioma: |
Inglês |
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Notas: |
CNPGC. |
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Conteúdo: |
This work provides information on genetic and pathogenic variation in isolates of Collectotrichum gloeosporioides which cause anthracnose disease in many species of the tropical pasture legume, Stylosanthes. Isolates collected from species other than S. guianensis mainly from the centre of host-pathogen diversity in South America were studied using Random Amplified Polymorphic DNA (RAPD) markers and differential virulence on a set of host differentials. A phenetic analysis of 90 isolates using RAPD markers showed a wide genetic diversity in the pathogen population. The genetic variation in the Australian population was very limited compared with that at the centre of diversity. A similar situation was detected for pathogenic variation in 69 isolates from Brazil, many of which showed higher severity on Australian cultivars and accessions. These include accessions and cultivars which are highly resistant to the Australian races of the pathogen. However, pathogenic diversity in the Brazilian population of C. gloeosporioides was only partly characterised due to the limited number of host differentials used in this study. Attention needs to focus on the development and use of a more extensive range of host differentials. There was no strong relationship between genetic and virulence markers. Consequently, pathogenicity tests need to be conducted to answer the more practical questions such as the risk to current commercial cultivars from markers will damaging races. Use of molecular be useful to understand better the movement of pathogen populations between geographically isolated regions. Isolates used in this work have come mainly from regions where S. capitata and S. guianensis are endemic. Further isolate sampling from regions representing the native range of commercial species such as S. scabra and S. hamata will be necessary for a more comprehensive understating of this diversity. MenosThis work provides information on genetic and pathogenic variation in isolates of Collectotrichum gloeosporioides which cause anthracnose disease in many species of the tropical pasture legume, Stylosanthes. Isolates collected from species other than S. guianensis mainly from the centre of host-pathogen diversity in South America were studied using Random Amplified Polymorphic DNA (RAPD) markers and differential virulence on a set of host differentials. A phenetic analysis of 90 isolates using RAPD markers showed a wide genetic diversity in the pathogen population. The genetic variation in the Australian population was very limited compared with that at the centre of diversity. A similar situation was detected for pathogenic variation in 69 isolates from Brazil, many of which showed higher severity on Australian cultivars and accessions. These include accessions and cultivars which are highly resistant to the Australian races of the pathogen. However, pathogenic diversity in the Brazilian population of C. gloeosporioides was only partly characterised due to the limited number of host differentials used in this study. Attention needs to focus on the development and use of a more extensive range of host differentials. There was no strong relationship between genetic and virulence markers. Consequently, pathogenicity tests need to be conducted to answer the more practical questions such as the risk to current commercial cultivars from markers will damaging races. Use of molecul... Mostrar Tudo |
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Palavras-Chave: |
Anthracnosis; Brasil; Colletotricum gloeosporioides. |
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Thesagro: |
Antracnose; Epidemiologia; Estilosante; Marcador Genético; Patogenicidade; Stylosanthes Guianensis; Stylosanthes Macrocephala; Stylosanthes Scabra; Variação Genética. |
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Thesaurus NAL: |
Australia; Brazil; Colombia; epidemiology; genetic markers; genetic variation; pathogenicity; Stylosanthes capitata; Stylosanthes hamata. |
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Categoria do assunto: |
-- |
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Marc: |
LEADER 03220naa a2200433 a 4500
001 1317327
005 1998-07-10
008 1997 bl uuuu u00u1 u #d
100 1 $aCHAKRABORTY, S.
245 $aBiodiversity, epidemiology and virulence of Colletotrichum gloeosporioides. II. Genetic and pathogenic diversity in isolates of Colletotrichum gloeosporioides from eight species of Stylosanthes.
260 $c1997
500 $aCNPGC.
520 $aThis work provides information on genetic and pathogenic variation in isolates of Collectotrichum gloeosporioides which cause anthracnose disease in many species of the tropical pasture legume, Stylosanthes. Isolates collected from species other than S. guianensis mainly from the centre of host-pathogen diversity in South America were studied using Random Amplified Polymorphic DNA (RAPD) markers and differential virulence on a set of host differentials. A phenetic analysis of 90 isolates using RAPD markers showed a wide genetic diversity in the pathogen population. The genetic variation in the Australian population was very limited compared with that at the centre of diversity. A similar situation was detected for pathogenic variation in 69 isolates from Brazil, many of which showed higher severity on Australian cultivars and accessions. These include accessions and cultivars which are highly resistant to the Australian races of the pathogen. However, pathogenic diversity in the Brazilian population of C. gloeosporioides was only partly characterised due to the limited number of host differentials used in this study. Attention needs to focus on the development and use of a more extensive range of host differentials. There was no strong relationship between genetic and virulence markers. Consequently, pathogenicity tests need to be conducted to answer the more practical questions such as the risk to current commercial cultivars from markers will damaging races. Use of molecular be useful to understand better the movement of pathogen populations between geographically isolated regions. Isolates used in this work have come mainly from regions where S. capitata and S. guianensis are endemic. Further isolate sampling from regions representing the native range of commercial species such as S. scabra and S. hamata will be necessary for a more comprehensive understating of this diversity.
650 $aAustralia
650 $aBrazil
650 $aColombia
650 $aepidemiology
650 $agenetic markers
650 $agenetic variation
650 $apathogenicity
650 $aStylosanthes capitata
650 $aStylosanthes hamata
650 $aAntracnose
650 $aEpidemiologia
650 $aEstilosante
650 $aMarcador Genético
650 $aPatogenicidade
650 $aStylosanthes Guianensis
650 $aStylosanthes Macrocephala
650 $aStylosanthes Scabra
650 $aVariação Genética
653 $aAnthracnosis
653 $aBrasil
653 $aColletotricum gloeosporioides
700 1 $aPERROT, R.
700 1 $aCHARCHAR, M. J. D`A.
700 1 $aFERNANDES, C. D.
700 1 $aKELEMU, S.
773 $tTropical Grasslands, Brisbane$gv.31, n.5, p.393-401, Nov. 1997.
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