Serveur d'exploration Phytophthora

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Discovery of Methyl (5 Z)-[2-(2,4,5-Trioxopyrrolidin-3-ylidene)-4-oxo-1,3-thiazolidin-5-ylidene]acetates as Antifungal Agents against Potato Diseases.

Identifieur interne : 000796 ( Main/Exploration ); précédent : 000795; suivant : 000797

Discovery of Methyl (5 Z)-[2-(2,4,5-Trioxopyrrolidin-3-ylidene)-4-oxo-1,3-thiazolidin-5-ylidene]acetates as Antifungal Agents against Potato Diseases.

Auteurs : Konstantin L. Obydennov [Russie] ; Liliya A. Khamidullina [Russie] ; Alexey N. Galushchinskiy [Russie] ; Svetlana A. Shatunova [Russie] ; Mariya F. Kosterina [Russie] ; Tatiana A. Kalinina [Russie] ; Zhijin Fan ; Tatiana V. Glukhareva [Russie] ; Yuri Yu Morzherin [Russie]

Source :

RBID : pubmed:29807429

Descripteurs français

English descriptors

Abstract

Synthesis, isomerism, and fungicidal activity against potato diseases of new (5 Z)-[2-(2,4,5-trioxopyrrolidin-3-ylidene)-4-oxo-1,3-thiazolidin-5-ylidene]acetate derivatives with 1,3-thiazolidine-4-one and pyrrolidine-2,3,5-trione moieties linked by an exocyclic C═C bond were described. Their structures were clearly confirmed by spectroscopic and spectrometric data (Fourier transform infrared spectroscopy, 1H and 13C nuclear magnetic resonance, and mass spectrometry), elemental analysis, and X-ray diffraction crystallography. A bioassay for antifungal activity in vitro against Phytophthora infestans, Fusariun solani, Alternaria solani, Rhizoctonia solani, and Colletotrichum coccodes demonstrated that 2,4,5-trioxopyrrolidin-1,3-thiazolidine derivatives exhibited a relatively broad spectrum of antifungal activity. One of the compounds showed considerable activity against all of the strains; in the case of F. solani, P. infestans, and A. solani, it possesses comparable or better fungicidal efficacy than the positive control Consento. Consequently, this compound is a promising fungicidal candidate for plant protection.

DOI: 10.1021/acs.jafc.8b02151
PubMed: 29807429


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Le document en format XML

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<term>Fungicides, Industrial (chemistry)</term>
<term>Fungicides, Industrial (pharmacology)</term>
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<term>Fongicides industriels (synthèse chimique)</term>
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<term>Maladies des plantes (prévention et contrôle)</term>
<term>Phytophthora infestans (effets des médicaments et des substances chimiques)</term>
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<div type="abstract" xml:lang="en">Synthesis, isomerism, and fungicidal activity against potato diseases of new (5 Z)-[2-(2,4,5-trioxopyrrolidin-3-ylidene)-4-oxo-1,3-thiazolidin-5-ylidene]acetate derivatives with 1,3-thiazolidine-4-one and pyrrolidine-2,3,5-trione moieties linked by an exocyclic C═C bond were described. Their structures were clearly confirmed by spectroscopic and spectrometric data (Fourier transform infrared spectroscopy,
<sup>1</sup>
H and
<sup>13</sup>
C nuclear magnetic resonance, and mass spectrometry), elemental analysis, and X-ray diffraction crystallography. A bioassay for antifungal activity in vitro against Phytophthora infestans, Fusariun solani, Alternaria solani, Rhizoctonia solani, and Colletotrichum coccodes demonstrated that 2,4,5-trioxopyrrolidin-1,3-thiazolidine derivatives exhibited a relatively broad spectrum of antifungal activity. One of the compounds showed considerable activity against all of the strains; in the case of F. solani, P. infestans, and A. solani, it possesses comparable or better fungicidal efficacy than the positive control Consento. Consequently, this compound is a promising fungicidal candidate for plant protection.</div>
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<sup>1</sup>
H and
<sup>13</sup>
C nuclear magnetic resonance, and mass spectrometry), elemental analysis, and X-ray diffraction crystallography. A bioassay for antifungal activity in vitro against Phytophthora infestans, Fusariun solani, Alternaria solani, Rhizoctonia solani, and Colletotrichum coccodes demonstrated that 2,4,5-trioxopyrrolidin-1,3-thiazolidine derivatives exhibited a relatively broad spectrum of antifungal activity. One of the compounds showed considerable activity against all of the strains; in the case of F. solani, P. infestans, and A. solani, it possesses comparable or better fungicidal efficacy than the positive control Consento. Consequently, this compound is a promising fungicidal candidate for plant protection.</AbstractText>
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<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="D005659">Fungicides, Industrial</NameOfSubstance>
</Chemical>
</ChemicalList>
<CitationSubset>IM</CitationSubset>
<MeshHeadingList>
<MeshHeading>
<DescriptorName UI="D000528" MajorTopicYN="N">Alternaria</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D055808" MajorTopicYN="N">Drug Discovery</DescriptorName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D005659" MajorTopicYN="N">Fungicides, Industrial</DescriptorName>
<QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D055750" MajorTopicYN="N">Phytophthora infestans</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D010935" MajorTopicYN="N">Plant Diseases</DescriptorName>
<QualifierName UI="Q000382" MajorTopicYN="Y">microbiology</QualifierName>
<QualifierName UI="Q000517" MajorTopicYN="N">prevention & control</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D012232" MajorTopicYN="N">Rhizoctonia</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D011198" MajorTopicYN="N">Solanum tuberosum</DescriptorName>
<QualifierName UI="Q000382" MajorTopicYN="Y">microbiology</QualifierName>
</MeshHeading>
</MeshHeadingList>
<KeywordList Owner="NOTNLM">
<Keyword MajorTopicYN="N">Alternaria solani</Keyword>
<Keyword MajorTopicYN="N">Colletotrichum coccodes</Keyword>
<Keyword MajorTopicYN="N">Fusariun solani</Keyword>
<Keyword MajorTopicYN="N">Phytophthora infestans</Keyword>
<Keyword MajorTopicYN="N">Rhizoctonia solani</Keyword>
<Keyword MajorTopicYN="N">antifungal activity</Keyword>
<Keyword MajorTopicYN="N">heterocyclic assembly</Keyword>
<Keyword MajorTopicYN="N">potato diseases</Keyword>
<Keyword MajorTopicYN="N">pyrrolidine</Keyword>
<Keyword MajorTopicYN="N">thiazolidine</Keyword>
</KeywordList>
</MedlineCitation>
<PubmedData>
<History>
<PubMedPubDate PubStatus="pubmed">
<Year>2018</Year>
<Month>5</Month>
<Day>29</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="medline">
<Year>2018</Year>
<Month>7</Month>
<Day>18</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="entrez">
<Year>2018</Year>
<Month>5</Month>
<Day>30</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
</History>
<PublicationStatus>ppublish</PublicationStatus>
<ArticleIdList>
<ArticleId IdType="pubmed">29807429</ArticleId>
<ArticleId IdType="doi">10.1021/acs.jafc.8b02151</ArticleId>
</ArticleIdList>
</PubmedData>
</pubmed>
<affiliations>
<list>
<country>
<li>Russie</li>
</country>
</list>
<tree>
<noCountry>
<name sortKey="Fan, Zhijin" sort="Fan, Zhijin" uniqKey="Fan Z" first="Zhijin" last="Fan">Zhijin Fan</name>
</noCountry>
<country name="Russie">
<noRegion>
<name sortKey="Obydennov, Konstantin L" sort="Obydennov, Konstantin L" uniqKey="Obydennov K" first="Konstantin L" last="Obydennov">Konstantin L. Obydennov</name>
</noRegion>
<name sortKey="Galushchinskiy, Alexey N" sort="Galushchinskiy, Alexey N" uniqKey="Galushchinskiy A" first="Alexey N" last="Galushchinskiy">Alexey N. Galushchinskiy</name>
<name sortKey="Glukhareva, Tatiana V" sort="Glukhareva, Tatiana V" uniqKey="Glukhareva T" first="Tatiana V" last="Glukhareva">Tatiana V. Glukhareva</name>
<name sortKey="Kalinina, Tatiana A" sort="Kalinina, Tatiana A" uniqKey="Kalinina T" first="Tatiana A" last="Kalinina">Tatiana A. Kalinina</name>
<name sortKey="Khamidullina, Liliya A" sort="Khamidullina, Liliya A" uniqKey="Khamidullina L" first="Liliya A" last="Khamidullina">Liliya A. Khamidullina</name>
<name sortKey="Khamidullina, Liliya A" sort="Khamidullina, Liliya A" uniqKey="Khamidullina L" first="Liliya A" last="Khamidullina">Liliya A. Khamidullina</name>
<name sortKey="Kosterina, Mariya F" sort="Kosterina, Mariya F" uniqKey="Kosterina M" first="Mariya F" last="Kosterina">Mariya F. Kosterina</name>
<name sortKey="Morzherin, Yuri Yu" sort="Morzherin, Yuri Yu" uniqKey="Morzherin Y" first="Yuri Yu" last="Morzherin">Yuri Yu Morzherin</name>
<name sortKey="Shatunova, Svetlana A" sort="Shatunova, Svetlana A" uniqKey="Shatunova S" first="Svetlana A" last="Shatunova">Svetlana A. Shatunova</name>
</country>
</tree>
</affiliations>
</record>

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