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 : 000797Discovery 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 :
- Journal of agricultural and food chemistry [ 1520-5118 ] ; 2018.
Descripteurs français
- KwdFr :
- Alternaria (effets des médicaments et des substances chimiques), Découverte de médicament (MeSH), Fongicides industriels (composition chimique), Fongicides industriels (pharmacologie), Fongicides industriels (synthèse chimique), Maladies des plantes (microbiologie), Maladies des plantes (prévention et contrôle), Phytophthora infestans (effets des médicaments et des substances chimiques), Rhizoctonia (effets des médicaments et des substances chimiques), Solanum tuberosum (microbiologie).
- MESH :
- composition chimique : Fongicides industriels.
- effets des médicaments et des substances chimiques : Alternaria, Phytophthora infestans, Rhizoctonia.
- microbiologie : Maladies des plantes, Solanum tuberosum.
- pharmacologie : Fongicides industriels.
- prévention et contrôle : Maladies des plantes.
- synthèse chimique : Fongicides industriels.
- Découverte de médicament.
English descriptors
- KwdEn :
- Alternaria (drug effects), Drug Discovery (MeSH), Fungicides, Industrial (chemical synthesis), Fungicides, Industrial (chemistry), Fungicides, Industrial (pharmacology), Phytophthora infestans (drug effects), Plant Diseases (microbiology), Plant Diseases (prevention & control), Rhizoctonia (drug effects), Solanum tuberosum (microbiology).
- MESH :
- chemical , chemical synthesis : Fungicides, Industrial.
- chemical , chemistry : Fungicides, Industrial.
- drug effects : Alternaria, Phytophthora infestans, Rhizoctonia.
- microbiology : Plant Diseases, Solanum tuberosum.
- chemical , pharmacology : Fungicides, Industrial.
- prevention & control : Plant Diseases.
- Drug Discovery.
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
Affiliations:
Links toward previous steps (curation, corpus...)
Le document en format XML
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<term>Fungicides, Industrial (pharmacology)</term>
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<front><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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<Month>07</Month>
<Day>17</Day>
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<Month>07</Month>
<Day>17</Day>
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<Issue>24</Issue>
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<Month>Jun</Month>
<Day>20</Day>
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<Title>Journal of agricultural and food chemistry</Title>
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<ArticleTitle>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.</ArticleTitle>
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<Abstract><AbstractText>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.</AbstractText>
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<AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Obydennov</LastName>
<ForeName>Konstantin L</ForeName>
<Initials>KL</Initials>
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<AffiliationInfo><Affiliation>Ural Federal University , 19 Mira Street , Ekaterinburg 620002 , Russia.</Affiliation>
</AffiliationInfo>
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<Author ValidYN="Y"><LastName>Khamidullina</LastName>
<ForeName>Liliya A</ForeName>
<Initials>LA</Initials>
<AffiliationInfo><Affiliation>Ural Federal University , 19 Mira Street , Ekaterinburg 620002 , Russia.</Affiliation>
</AffiliationInfo>
<AffiliationInfo><Affiliation>Postovsky Institute of Organic Synthesis , Ural Branch of the Russian Academy of Sciences (UB RAS) , 22 Sofia Kovalevskaya Street , Ekaterinburg 620990 , Russia.</Affiliation>
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<Author ValidYN="Y"><LastName>Galushchinskiy</LastName>
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<Initials>AN</Initials>
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</AffiliationInfo>
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<ForeName>Svetlana A</ForeName>
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</AffiliationInfo>
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<Author ValidYN="Y"><LastName>Kosterina</LastName>
<ForeName>Mariya F</ForeName>
<Initials>MF</Initials>
<AffiliationInfo><Affiliation>Ural Federal University , 19 Mira Street , Ekaterinburg 620002 , Russia.</Affiliation>
</AffiliationInfo>
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<Author ValidYN="Y"><LastName>Kalinina</LastName>
<ForeName>Tatiana A</ForeName>
<Initials>TA</Initials>
<AffiliationInfo><Affiliation>Ural Federal University , 19 Mira Street , Ekaterinburg 620002 , Russia.</Affiliation>
</AffiliationInfo>
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<Author ValidYN="Y"><LastName>Fan</LastName>
<ForeName>Zhijin</ForeName>
<Initials>Z</Initials>
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<Author ValidYN="Y"><LastName>Glukhareva</LastName>
<ForeName>Tatiana V</ForeName>
<Initials>TV</Initials>
<AffiliationInfo><Affiliation>Ural Federal University , 19 Mira Street , Ekaterinburg 620002 , Russia.</Affiliation>
</AffiliationInfo>
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<Author ValidYN="Y"><LastName>Morzherin</LastName>
<ForeName>Yuri Yu</ForeName>
<Initials>YY</Initials>
<Identifier Source="ORCID">http://orcid.org/0000-0002-1333-6676</Identifier>
<AffiliationInfo><Affiliation>Ural Federal University , 19 Mira Street , Ekaterinburg 620002 , Russia.</Affiliation>
</AffiliationInfo>
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</AuthorList>
<Language>eng</Language>
<PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType>
</PublicationTypeList>
<ArticleDate DateType="Electronic"><Year>2018</Year>
<Month>06</Month>
<Day>07</Day>
</ArticleDate>
</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="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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