Cleavage of the diketonitrile derivative of the herbicide isoxaflutole by extracellular fungal oxidases.
Identifieur interne : 000A79 ( Main/Curation ); précédent : 000A78; suivant : 000A80Cleavage of the diketonitrile derivative of the herbicide isoxaflutole by extracellular fungal oxidases.
Auteurs : C. Mougin [France] ; F D Boyer ; E. Caminade ; R. RamaSource :
- Journal of agricultural and food chemistry [ 0021-8561 ] ; 2000.
Descripteurs français
- KwdFr :
- MESH :
- composition chimique : Herbicides, Isoxazoles, Nitriles, Oxidoreductases.
- enzymologie : Espace extracellulaire, Phanerochaete, Polyporaceae.
- Indicateurs et réactifs.
English descriptors
- KwdEn :
- MESH :
- chemical , chemistry : Herbicides, Isoxazoles, Nitriles, Oxidoreductases.
- enzymology : Extracellular Space, Phanerochaete, Polyporaceae.
- chemical : Indicators and Reagents.
Abstract
Isoxaflutole is a herbicide activated in soils and plants to its diketonitrile derivative, the active herbicide principle. The diketonitrile derivative undergoes cleavage to the inactive benzoic acid analogue. In this paper, it is established that an oxidative mechanism implicating two successive reactions in the presence of dimethyldioxirane can chemically initiate the cleavage of the diketonitrile. It is also shown that two white rot strains, Phanerochaete chrysosporium and Trametes versicolor, are able to convert the diketonitrile to the acid when cultured in liquid media. This main metabolite amounts to 24.6 and 15.1% of initial herbicide content after 12-15 days of culture. Another polar metabolite represents <3.7% of the parent compound amount during the same period. Oxidative enzymes produced by the fungi show a time course similar to that of diketonitrile degradation. Purified laccase (EC 1. 10.3.2), in the presence of 2 mM 2, 2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) acting as a redox mediator at pH 3 supports the reaction with rates of 0.3-0.4 nmol h(-)(1) unit(-)(1).
DOI: 10.1021/jf000397q
PubMed: 11052694
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The diketonitrile derivative undergoes cleavage to the inactive benzoic acid analogue. In this paper, it is established that an oxidative mechanism implicating two successive reactions in the presence of dimethyldioxirane can chemically initiate the cleavage of the diketonitrile. It is also shown that two white rot strains, Phanerochaete chrysosporium and Trametes versicolor, are able to convert the diketonitrile to the acid when cultured in liquid media. This main metabolite amounts to 24.6 and 15.1% of initial herbicide content after 12-15 days of culture. Another polar metabolite represents <3.7% of the parent compound amount during the same period. Oxidative enzymes produced by the fungi show a time course similar to that of diketonitrile degradation. Purified laccase (EC 1. 10.3.2), in the presence of 2 mM 2, 2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) acting as a redox mediator at pH 3 supports the reaction with rates of 0.3-0.4 nmol h(-)(1) unit(-)(1).</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">11052694</PMID><DateCompleted><Year>2000</Year><Month>12</Month><Day>12</Day></DateCompleted><DateRevised><Year>2019</Year><Month>07</Month><Day>23</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0021-8561</ISSN><JournalIssue CitedMedium="Print"><Volume>48</Volume><Issue>10</Issue><PubDate><Year>2000</Year><Month>Oct</Month></PubDate></JournalIssue><Title>Journal of agricultural and food chemistry</Title><ISOAbbreviation>J Agric Food Chem</ISOAbbreviation></Journal><ArticleTitle>Cleavage of the diketonitrile derivative of the herbicide isoxaflutole by extracellular fungal oxidases.</ArticleTitle><Pagination><MedlinePgn>4529-34</MedlinePgn></Pagination><Abstract><AbstractText>Isoxaflutole is a herbicide activated in soils and plants to its diketonitrile derivative, the active herbicide principle. 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Purified laccase (EC 1. 10.3.2), in the presence of 2 mM 2, 2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) acting as a redox mediator at pH 3 supports the reaction with rates of 0.3-0.4 nmol h(-)(1) unit(-)(1).</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Mougin</LastName><ForeName>C</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>INRA, Unité de Phytopharmacie et Médiateurs Chimiques, Route de saint-Cyr, 78026 Versailles Cedex, France. mougin@versailles.inra.fr</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Boyer</LastName><ForeName>F D</ForeName><Initials>FD</Initials></Author><Author ValidYN="Y"><LastName>Caminade</LastName><ForeName>E</ForeName><Initials>E</Initials></Author><Author ValidYN="Y"><LastName>Rama</LastName><ForeName>R</ForeName><Initials>R</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Agric Food Chem</MedlineTA><NlmUniqueID>0374755</NlmUniqueID><ISSNLinking>0021-8561</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D006540">Herbicides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D007202">Indicators and Reagents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D007555">Isoxazoles</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009570">Nitriles</NameOfSubstance></Chemical><Chemical><RegistryNumber>0T9R0O0EYT</RegistryNumber><NameOfSubstance UI="C415327">isoxaflutole</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 1.-</RegistryNumber><NameOfSubstance UI="D010088">Oxidoreductases</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D005110" MajorTopicYN="N">Extracellular Space</DescriptorName><QualifierName UI="Q000201" MajorTopicYN="N">enzymology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006540" MajorTopicYN="N">Herbicides</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D007202" MajorTopicYN="N">Indicators and Reagents</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D007555" MajorTopicYN="N">Isoxazoles</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D009570" MajorTopicYN="N">Nitriles</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010088" MajorTopicYN="N">Oxidoreductases</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D020075" MajorTopicYN="N">Phanerochaete</DescriptorName><QualifierName UI="Q000201" MajorTopicYN="Y">enzymology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D011124" MajorTopicYN="N">Polyporaceae</DescriptorName><QualifierName UI="Q000201" MajorTopicYN="Y">enzymology</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2000</Year><Month>10</Month><Day>29</Day><Hour>11</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2001</Year><Month>2</Month><Day>28</Day><Hour>10</Hour><Minute>1</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2000</Year><Month>10</Month><Day>29</Day><Hour>11</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">11052694</ArticleId><ArticleId IdType="pii">jf000397q</ArticleId><ArticleId IdType="doi">10.1021/jf000397q</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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