PhytophthoraV1, Main, Exploration, bibRecord, 000544

Design, synthesis and fungicidal activity evaluation of novel pyrimidinamine derivatives containing phenyl-thiazole/oxazole moiety.

Identifieur interne : 000544 ( Main/Exploration ); précédent : 000543; suivant : 000545

Design, synthesis and fungicidal activity evaluation of novel pyrimidinamine derivatives containing phenyl-thiazole/oxazole moiety.

Source :

Bioorganic & medicinal chemistry [ 1464-3391 ] ; 2019.

RBID : pubmed:31160140

Descripteurs français

KwdFr :
- Alternaria (effets des médicaments et des substances chimiques), Antifongiques (composition chimique), Antifongiques (pharmacologie), Antifongiques (synthèse chimique), Ascomycota (effets des médicaments et des substances chimiques), Botrytis (effets des médicaments et des substances chimiques), Conception de médicament (MeSH), Fongicides industriels (composition chimique), Fongicides industriels (pharmacologie), Fongicides industriels (synthèse chimique), Gibberella (effets des médicaments et des substances chimiques), Oxazoles (composition chimique), Oxazoles (pharmacologie), Phytophthora (effets des médicaments et des substances chimiques), Pyrimidines (composition chimique), Pyrimidines (pharmacologie), Pyrimidines (synthèse chimique), Relation dose-effet des médicaments (MeSH), Relation structure-activité (MeSH), Structure moléculaire (MeSH), Tests de sensibilité microbienne (MeSH), Thiazoles (composition chimique), Thiazoles (pharmacologie), Théorie de la fonctionnelle de la densité (MeSH).
MESH :
- composition chimique : Antifongiques, Fongicides industriels, Oxazoles, Pyrimidines, Thiazoles.
- effets des médicaments et des substances chimiques : Alternaria, Ascomycota, Botrytis, Gibberella, Phytophthora.
- pharmacologie : Antifongiques, Fongicides industriels, Oxazoles, Pyrimidines, Thiazoles.
- synthèse chimique : Antifongiques, Fongicides industriels, Pyrimidines.
- Conception de médicament, Relation dose-effet des médicaments, Relation structure-activité, Structure moléculaire, Tests de sensibilité microbienne, Théorie de la fonctionnelle de la densité.

English descriptors

KwdEn :
- Alternaria (drug effects), Antifungal Agents (chemical synthesis), Antifungal Agents (chemistry), Antifungal Agents (pharmacology), Ascomycota (drug effects), Botrytis (drug effects), Density Functional Theory (MeSH), Dose-Response Relationship, Drug (MeSH), Drug Design (MeSH), Fungicides, Industrial (chemical synthesis), Fungicides, Industrial (chemistry), Fungicides, Industrial (pharmacology), Gibberella (drug effects), Microbial Sensitivity Tests (MeSH), Molecular Structure (MeSH), Oxazoles (chemistry), Oxazoles (pharmacology), Phytophthora (drug effects), Pyrimidines (chemical synthesis), Pyrimidines (chemistry), Pyrimidines (pharmacology), Structure-Activity Relationship (MeSH), Thiazoles (chemistry), Thiazoles (pharmacology).
MESH :
- chemical , chemical synthesis : Antifungal Agents, Fungicides, Industrial, Pyrimidines.
- chemical , chemistry : Antifungal Agents, Fungicides, Industrial, Oxazoles, Pyrimidines, Thiazoles.
- drug effects : Alternaria, Ascomycota, Botrytis, Gibberella, Phytophthora.
- chemical , pharmacology : Antifungal Agents, Fungicides, Industrial, Oxazoles, Pyrimidines, Thiazoles.
- Density Functional Theory, Dose-Response Relationship, Drug, Drug Design, Microbial Sensitivity Tests, Molecular Structure, Structure-Activity Relationship.

Abstract

Diflumetorim is a member of pyrimidinamine fungicides that possess excellent antifungal activities. Nevertheless, as reported that the activity of diflumetorim to corn rust (Puccinia sorghi) was not ideal (EC₅₀ = 53.26 mg/L). Herein, a series of novel pyrimidinamine derivatives containing phenyl-thiazole/oxazole moiety were designed based on our previous study and the structural characteristics of diflumetorim, synthesized and bioassayed to discover novel fungicides with excellent antifungal activities. Among these compounds, T18 gave the optimal fungicidal activity, which respectively offers control effects with EC₅₀ values of 0.93 mg/L against P. sorghi and 1.24 mg/L against E. graminis, significantly superior to commercial fungicides diflumetorim, tebuconazole, and flusilazole. Cell cytotoxicity results suggested that compound T18 has lower toxicities than diflumetorim. Furthermore, DFT calculation indicated that the phenyl-thiazole/oxazole moiety plays an unarguable role in the improvement of activity, which will contribute to designing and developing more potent compounds in the future.

DOI: 10.1016/j.bmc.2019.05.029
PubMed: 31160140

Affiliations:

République populaire de Chine

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to stream Main, to step Corpus: 000463
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Le document en format XML

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<wicri:regionArea>College of Chemistry and Chemical Engineering, Hunan University, No. 1 Lushan Road(s), Changsha 410082, Hunan Province, People's Republic of China; National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007, Hunan Province</wicri:regionArea>
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<author><name sortKey="Yi, Haibo" sort="Yi, Haibo" uniqKey="Yi H" first="Haibo" last="Yi">Haibo Yi</name>
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<country xml:lang="fr">République populaire de Chine</country>
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<author><name sortKey="Zhang, Ning" sort="Zhang, Ning" uniqKey="Zhang N" first="Ning" last="Zhang">Ning Zhang</name>
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<author><name sortKey="Liu, Minhua" sort="Liu, Minhua" uniqKey="Liu M" first="Minhua" last="Liu">Minhua Liu</name>
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<country xml:lang="fr">République populaire de Chine</country>
<wicri:regionArea>National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007, Hunan Province, People's Republic of China; Hunan Province Key Laboratory for Agrochemicals, Changsha 410014</wicri:regionArea>
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<author><name sortKey="Huang, Lu" sort="Huang, Lu" uniqKey="Huang L" first="Lu" last="Huang">Lu Huang</name>
<affiliation wicri:level="1"><nlm:affiliation>National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007, Hunan Province, People's Republic of China; Hunan Province Key Laboratory for Agrochemicals, Changsha 410014, People's Republic of China.</nlm:affiliation>
<country xml:lang="fr">République populaire de Chine</country>
<wicri:regionArea>National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007, Hunan Province, People's Republic of China; Hunan Province Key Laboratory for Agrochemicals, Changsha 410014</wicri:regionArea>
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</author>
<author><name sortKey="Ren, Jianwei" sort="Ren, Jianwei" uniqKey="Ren J" first="Jianwei" last="Ren">Jianwei Ren</name>
<affiliation wicri:level="1"><nlm:affiliation>National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007, Hunan Province, People's Republic of China; Hunan Province Key Laboratory for Agrochemicals, Changsha 410014, People's Republic of China.</nlm:affiliation>
<country xml:lang="fr">République populaire de Chine</country>
<wicri:regionArea>National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007, Hunan Province, People's Republic of China; Hunan Province Key Laboratory for Agrochemicals, Changsha 410014</wicri:regionArea>
<wicri:noRegion>Changsha 410014</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Liu, Weidong" sort="Liu, Weidong" uniqKey="Liu W" first="Weidong" last="Liu">Weidong Liu</name>
<affiliation wicri:level="1"><nlm:affiliation>National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007, Hunan Province, People's Republic of China; Hunan Province Key Laboratory for Agrochemicals, Changsha 410014, People's Republic of China. Electronic address: weidliu@yahoo.com.</nlm:affiliation>
<country xml:lang="fr">République populaire de Chine</country>
<wicri:regionArea>National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007, Hunan Province, People's Republic of China; Hunan Province Key Laboratory for Agrochemicals, Changsha 410014</wicri:regionArea>
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<author><name sortKey="Hu, Aixi" sort="Hu, Aixi" uniqKey="Hu A" first="Aixi" last="Hu">Aixi Hu</name>
<affiliation wicri:level="1"><nlm:affiliation>College of Chemistry and Chemical Engineering, Hunan University, No. 1 Lushan Road(s), Changsha 410082, Hunan Province, People's Republic of China. Electronic address: axhu@hnu.edu.cn.</nlm:affiliation>
<country xml:lang="fr">République populaire de Chine</country>
<wicri:regionArea>College of Chemistry and Chemical Engineering, Hunan University, No. 1 Lushan Road(s), Changsha 410082, Hunan Province</wicri:regionArea>
<wicri:noRegion>Hunan Province</wicri:noRegion>
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<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Alternaria (drug effects)</term>
<term>Antifungal Agents (chemical synthesis)</term>
<term>Antifungal Agents (chemistry)</term>
<term>Antifungal Agents (pharmacology)</term>
<term>Ascomycota (drug effects)</term>
<term>Botrytis (drug effects)</term>
<term>Density Functional Theory (MeSH)</term>
<term>Dose-Response Relationship, Drug (MeSH)</term>
<term>Drug Design (MeSH)</term>
<term>Fungicides, Industrial (chemical synthesis)</term>
<term>Fungicides, Industrial (chemistry)</term>
<term>Fungicides, Industrial (pharmacology)</term>
<term>Gibberella (drug effects)</term>
<term>Microbial Sensitivity Tests (MeSH)</term>
<term>Molecular Structure (MeSH)</term>
<term>Oxazoles (chemistry)</term>
<term>Oxazoles (pharmacology)</term>
<term>Phytophthora (drug effects)</term>
<term>Pyrimidines (chemical synthesis)</term>
<term>Pyrimidines (chemistry)</term>
<term>Pyrimidines (pharmacology)</term>
<term>Structure-Activity Relationship (MeSH)</term>
<term>Thiazoles (chemistry)</term>
<term>Thiazoles (pharmacology)</term>
</keywords>
<keywords scheme="KwdFr" xml:lang="fr"><term>Alternaria (effets des médicaments et des substances chimiques)</term>
<term>Antifongiques (composition chimique)</term>
<term>Antifongiques (pharmacologie)</term>
<term>Antifongiques (synthèse chimique)</term>
<term>Ascomycota (effets des médicaments et des substances chimiques)</term>
<term>Botrytis (effets des médicaments et des substances chimiques)</term>
<term>Conception de médicament (MeSH)</term>
<term>Fongicides industriels (composition chimique)</term>
<term>Fongicides industriels (pharmacologie)</term>
<term>Fongicides industriels (synthèse chimique)</term>
<term>Gibberella (effets des médicaments et des substances chimiques)</term>
<term>Oxazoles (composition chimique)</term>
<term>Oxazoles (pharmacologie)</term>
<term>Phytophthora (effets des médicaments et des substances chimiques)</term>
<term>Pyrimidines (composition chimique)</term>
<term>Pyrimidines (pharmacologie)</term>
<term>Pyrimidines (synthèse chimique)</term>
<term>Relation dose-effet des médicaments (MeSH)</term>
<term>Relation structure-activité (MeSH)</term>
<term>Structure moléculaire (MeSH)</term>
<term>Tests de sensibilité microbienne (MeSH)</term>
<term>Thiazoles (composition chimique)</term>
<term>Thiazoles (pharmacologie)</term>
<term>Théorie de la fonctionnelle de la densité (MeSH)</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antifungal Agents</term>
<term>Fungicides, Industrial</term>
<term>Pyrimidines</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antifungal Agents</term>
<term>Fungicides, Industrial</term>
<term>Oxazoles</term>
<term>Pyrimidines</term>
<term>Thiazoles</term>
</keywords>
<keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Antifongiques</term>
<term>Fongicides industriels</term>
<term>Oxazoles</term>
<term>Pyrimidines</term>
<term>Thiazoles</term>
</keywords>
<keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Alternaria</term>
<term>Ascomycota</term>
<term>Botrytis</term>
<term>Gibberella</term>
<term>Phytophthora</term>
</keywords>
<keywords scheme="MESH" qualifier="effets des médicaments et des substances chimiques" xml:lang="fr"><term>Alternaria</term>
<term>Ascomycota</term>
<term>Botrytis</term>
<term>Gibberella</term>
<term>Phytophthora</term>
</keywords>
<keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antifongiques</term>
<term>Fongicides industriels</term>
<term>Oxazoles</term>
<term>Pyrimidines</term>
<term>Thiazoles</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antifungal Agents</term>
<term>Fungicides, Industrial</term>
<term>Oxazoles</term>
<term>Pyrimidines</term>
<term>Thiazoles</term>
</keywords>
<keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antifongiques</term>
<term>Fongicides industriels</term>
<term>Pyrimidines</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Density Functional Theory</term>
<term>Dose-Response Relationship, Drug</term>
<term>Drug Design</term>
<term>Microbial Sensitivity Tests</term>
<term>Molecular Structure</term>
<term>Structure-Activity Relationship</term>
</keywords>
<keywords scheme="MESH" xml:lang="fr"><term>Conception de médicament</term>
<term>Relation dose-effet des médicaments</term>
<term>Relation structure-activité</term>
<term>Structure moléculaire</term>
<term>Tests de sensibilité microbienne</term>
<term>Théorie de la fonctionnelle de la densité</term>
</keywords>
</textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en">Diflumetorim is a member of pyrimidinamine fungicides that possess excellent antifungal activities. Nevertheless, as reported that the activity of diflumetorim to corn rust (Puccinia sorghi) was not ideal (EC<sub>50</sub>
 = 53.26 mg/L). Herein, a series of novel pyrimidinamine derivatives containing phenyl-thiazole/oxazole moiety were designed based on our previous study and the structural characteristics of diflumetorim, synthesized and bioassayed to discover novel fungicides with excellent antifungal activities. Among these compounds, T18 gave the optimal fungicidal activity, which respectively offers control effects with EC<sub>50</sub>
 values of 0.93 mg/L against P. sorghi and 1.24 mg/L against E. graminis, significantly superior to commercial fungicides diflumetorim, tebuconazole, and flusilazole. Cell cytotoxicity results suggested that compound T18 has lower toxicities than diflumetorim. Furthermore, DFT calculation indicated that the phenyl-thiazole/oxazole moiety plays an unarguable role in the improvement of activity, which will contribute to designing and developing more potent compounds in the future.</div>
</front>
</TEI>
<pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">31160140</PMID>
<DateCompleted><Year>2020</Year>
<Month>09</Month>
<Day>22</Day>
</DateCompleted>
<DateRevised><Year>2020</Year>
<Month>09</Month>
<Day>22</Day>
</DateRevised>
<Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1464-3391</ISSN>
<JournalIssue CitedMedium="Internet"><Volume>27</Volume>
<Issue>15</Issue>
<PubDate><Year>2019</Year>
<Month>08</Month>
<Day>01</Day>
</PubDate>
</JournalIssue>
<Title>Bioorganic & medicinal chemistry</Title>
<ISOAbbreviation>Bioorg Med Chem</ISOAbbreviation>
</Journal>
<ArticleTitle>Design, synthesis and fungicidal activity evaluation of novel pyrimidinamine derivatives containing phenyl-thiazole/oxazole moiety.</ArticleTitle>
<Pagination><MedlinePgn>3218-3228</MedlinePgn>
</Pagination>
<ELocationID EIdType="pii" ValidYN="Y">S0968-0896(19)30182-8</ELocationID>
<ELocationID EIdType="doi" ValidYN="Y">10.1016/j.bmc.2019.05.029</ELocationID>
<Abstract><AbstractText>Diflumetorim is a member of pyrimidinamine fungicides that possess excellent antifungal activities. Nevertheless, as reported that the activity of diflumetorim to corn rust (Puccinia sorghi) was not ideal (EC<sub>50</sub>
 = 53.26 mg/L). Herein, a series of novel pyrimidinamine derivatives containing phenyl-thiazole/oxazole moiety were designed based on our previous study and the structural characteristics of diflumetorim, synthesized and bioassayed to discover novel fungicides with excellent antifungal activities. Among these compounds, T18 gave the optimal fungicidal activity, which respectively offers control effects with EC<sub>50</sub>
 values of 0.93 mg/L against P. sorghi and 1.24 mg/L against E. graminis, significantly superior to commercial fungicides diflumetorim, tebuconazole, and flusilazole. Cell cytotoxicity results suggested that compound T18 has lower toxicities than diflumetorim. Furthermore, DFT calculation indicated that the phenyl-thiazole/oxazole moiety plays an unarguable role in the improvement of activity, which will contribute to designing and developing more potent compounds in the future.</AbstractText>
<CopyrightInformation>Copyright © 2019 Elsevier Ltd. All rights reserved.</CopyrightInformation>
</Abstract>
<AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Yan</LastName>
<ForeName>Zhongzhong</ForeName>
<Initials>Z</Initials>
<AffiliationInfo><Affiliation>College of Chemistry and Chemical Engineering, Hunan University, No. 1 Lushan Road(s), Changsha 410082, Hunan Province, People's Republic of China; National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007, Hunan Province, People's Republic of China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Liu</LastName>
<ForeName>Aiping</ForeName>
<Initials>A</Initials>
<AffiliationInfo><Affiliation>National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007, Hunan Province, People's Republic of China; Hunan Province Key Laboratory for Agrochemicals, Changsha 410014, People's Republic of China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Ou</LastName>
<ForeName>Yingcan</ForeName>
<Initials>Y</Initials>
<AffiliationInfo><Affiliation>Schooll of Medicine, Hunan University of Chinese Medicine, Changsha 410208, People's Republic of China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Li</LastName>
<ForeName>Jianming</ForeName>
<Initials>J</Initials>
<AffiliationInfo><Affiliation>National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007, Hunan Province, People's Republic of China; Hunan Province Key Laboratory for Agrochemicals, Changsha 410014, People's Republic of China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Yi</LastName>
<ForeName>Haibo</ForeName>
<Initials>H</Initials>
<AffiliationInfo><Affiliation>College of Chemistry and Chemical Engineering, Hunan University, No. 1 Lushan Road(s), Changsha 410082, Hunan Province, People's Republic of China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Zhang</LastName>
<ForeName>Ning</ForeName>
<Initials>N</Initials>
<AffiliationInfo><Affiliation>National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007, Hunan Province, People's Republic of China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Liu</LastName>
<ForeName>Minhua</ForeName>
<Initials>M</Initials>
<AffiliationInfo><Affiliation>National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007, Hunan Province, People's Republic of China; Hunan Province Key Laboratory for Agrochemicals, Changsha 410014, People's Republic of China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Huang</LastName>
<ForeName>Lu</ForeName>
<Initials>L</Initials>
<AffiliationInfo><Affiliation>National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007, Hunan Province, People's Republic of China; Hunan Province Key Laboratory for Agrochemicals, Changsha 410014, People's Republic of China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Ren</LastName>
<ForeName>Jianwei</ForeName>
<Initials>J</Initials>
<AffiliationInfo><Affiliation>National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007, Hunan Province, People's Republic of China; Hunan Province Key Laboratory for Agrochemicals, Changsha 410014, People's Republic of China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Liu</LastName>
<ForeName>Weidong</ForeName>
<Initials>W</Initials>
<AffiliationInfo><Affiliation>National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007, Hunan Province, People's Republic of China; Hunan Province Key Laboratory for Agrochemicals, Changsha 410014, People's Republic of China. Electronic address: weidliu@yahoo.com.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Hu</LastName>
<ForeName>Aixi</ForeName>
<Initials>A</Initials>
<AffiliationInfo><Affiliation>College of Chemistry and Chemical Engineering, Hunan University, No. 1 Lushan Road(s), Changsha 410082, Hunan Province, People's Republic of China. Electronic address: axhu@hnu.edu.cn.</Affiliation>
</AffiliationInfo>
</Author>
</AuthorList>
<Language>eng</Language>
<PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType>
<PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType>
</PublicationTypeList>
<ArticleDate DateType="Electronic"><Year>2019</Year>
<Month>05</Month>
<Day>20</Day>
</ArticleDate>
</Article>
<MedlineJournalInfo><Country>England</Country>
<MedlineTA>Bioorg Med Chem</MedlineTA>
<NlmUniqueID>9413298</NlmUniqueID>
<ISSNLinking>0968-0896</ISSNLinking>
</MedlineJournalInfo>
<ChemicalList><Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D000935">Antifungal Agents</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D005659">Fungicides, Industrial</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D010080">Oxazoles</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D011743">Pyrimidines</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D013844">Thiazoles</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="D000935" MajorTopicYN="N">Antifungal Agents</DescriptorName>
<QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D001203" MajorTopicYN="N">Ascomycota</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D020171" MajorTopicYN="N">Botrytis</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D000077318" MajorTopicYN="N">Density Functional Theory</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D004305" MajorTopicYN="N">Dose-Response Relationship, Drug</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D015195" MajorTopicYN="Y">Drug Design</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D005659" MajorTopicYN="N">Fungicides, Industrial</DescriptorName>
<QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D005874" MajorTopicYN="N">Gibberella</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D008826" MajorTopicYN="N">Microbial Sensitivity Tests</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D010080" MajorTopicYN="N">Oxazoles</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D010838" MajorTopicYN="N">Phytophthora</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D011743" MajorTopicYN="N">Pyrimidines</DescriptorName>
<QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D013844" MajorTopicYN="N">Thiazoles</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName>
</MeshHeading>
</MeshHeadingList>
<KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="Y">Antifungal activities</Keyword>
<Keyword MajorTopicYN="Y">DFT calculation</Keyword>
<Keyword MajorTopicYN="Y">Diflumetorim</Keyword>
<Keyword MajorTopicYN="Y">Puccinia sorghi</Keyword>
<Keyword MajorTopicYN="Y">Pyrimidinamine</Keyword>
</KeywordList>
</MedlineCitation>
<PubmedData><History><PubMedPubDate PubStatus="received"><Year>2019</Year>
<Month>02</Month>
<Day>03</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="revised"><Year>2019</Year>
<Month>05</Month>
<Day>02</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="accepted"><Year>2019</Year>
<Month>05</Month>
<Day>18</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="pubmed"><Year>2019</Year>
<Month>6</Month>
<Day>5</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="medline"><Year>2020</Year>
<Month>9</Month>
<Day>23</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="entrez"><Year>2019</Year>
<Month>6</Month>
<Day>5</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
</History>
<PublicationStatus>ppublish</PublicationStatus>
<ArticleIdList><ArticleId IdType="pubmed">31160140</ArticleId>
<ArticleId IdType="pii">S0968-0896(19)30182-8</ArticleId>
<ArticleId IdType="doi">10.1016/j.bmc.2019.05.029</ArticleId>
</ArticleIdList>
</PubmedData>
</pubmed>
<affiliations><list><country><li>République populaire de Chine</li>
</country>
</list>
<tree><country name="République populaire de Chine"><noRegion><name sortKey="Yan, Zhongzhong" sort="Yan, Zhongzhong" uniqKey="Yan Z" first="Zhongzhong" last="Yan">Zhongzhong Yan</name>
</noRegion>
<name sortKey="Hu, Aixi" sort="Hu, Aixi" uniqKey="Hu A" first="Aixi" last="Hu">Aixi Hu</name>
<name sortKey="Huang, Lu" sort="Huang, Lu" uniqKey="Huang L" first="Lu" last="Huang">Lu Huang</name>
<name sortKey="Li, Jianming" sort="Li, Jianming" uniqKey="Li J" first="Jianming" last="Li">Jianming Li</name>
<name sortKey="Liu, Aiping" sort="Liu, Aiping" uniqKey="Liu A" first="Aiping" last="Liu">Aiping Liu</name>
<name sortKey="Liu, Minhua" sort="Liu, Minhua" uniqKey="Liu M" first="Minhua" last="Liu">Minhua Liu</name>
<name sortKey="Liu, Weidong" sort="Liu, Weidong" uniqKey="Liu W" first="Weidong" last="Liu">Weidong Liu</name>
<name sortKey="Ou, Yingcan" sort="Ou, Yingcan" uniqKey="Ou Y" first="Yingcan" last="Ou">Yingcan Ou</name>
<name sortKey="Ren, Jianwei" sort="Ren, Jianwei" uniqKey="Ren J" first="Jianwei" last="Ren">Jianwei Ren</name>
<name sortKey="Yi, Haibo" sort="Yi, Haibo" uniqKey="Yi H" first="Haibo" last="Yi">Haibo Yi</name>
<name sortKey="Zhang, Ning" sort="Zhang, Ning" uniqKey="Zhang N" first="Ning" last="Zhang">Ning Zhang</name>
</country>
</tree>
</affiliations>
</record>

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Design, synthesis and fungicidal activity evaluation of novel pyrimidinamine derivatives containing phenyl-thiazole/oxazole moiety.

Design, synthesis and fungicidal activity evaluation of novel pyrimidinamine derivatives containing phenyl-thiazole/oxazole moiety.

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