Antifungal Application of Rosin Derivatives from Renewable Pine Resin in Crop Protection.
Identifieur interne : 000300 ( Main/Exploration ); précédent : 000299; suivant : 000301Antifungal Application of Rosin Derivatives from Renewable Pine Resin in Crop Protection.
Auteurs : Pan Tao [République populaire de Chine] ; Chengyu Wu [République populaire de Chine] ; Jin Hao [République populaire de Chine] ; Yanqing Gao [République populaire de Chine] ; Xiaohua He [République populaire de Chine] ; Jian Li [République populaire de Chine] ; Shibin Shang [République populaire de Chine] ; Zhanqian Song [République populaire de Chine] ; Jie Song [États-Unis]Source :
- Journal of agricultural and food chemistry [ 1520-5118 ] ; 2020.
Descripteurs français
- KwdFr :
- Amides (synthèse chimique), Antifongiques (composition chimique), Antifongiques (pharmacologie), Ascomycota (effets des médicaments et des substances chimiques), Deuteromycota (effets des médicaments et des substances chimiques), Découverte de médicament (MeSH), Fusarium (effets des médicaments et des substances chimiques), Phytophthora (effets des médicaments et des substances chimiques), Produits biologiques (composition chimique), Produits biologiques (pharmacologie), Protection des cultures (méthodes), Pyrazoles (composition chimique), Pyrazoles (pharmacologie), Relation structure-activité (MeSH), Résines végétales (composition chimique), Résines végétales (pharmacologie), Structure moléculaire (MeSH), Tests de sensibilité microbienne (MeSH), Thiophènes (composition chimique), Thiophènes (pharmacologie).
- MESH :
- composition chimique : Antifongiques, Produits biologiques, Pyrazoles, Résines végétales, Thiophènes.
- effets des médicaments et des substances chimiques : Ascomycota, Deuteromycota, Fusarium, Phytophthora.
- méthodes : Protection des cultures.
- pharmacologie : Antifongiques, Produits biologiques, Pyrazoles, Résines végétales, Thiophènes.
- synthèse chimique : Amides.
- Découverte de médicament, Relation structure-activité, Structure moléculaire, Tests de sensibilité microbienne.
English descriptors
- KwdEn :
- Amides (chemical synthesis), Antifungal Agents (chemistry), Antifungal Agents (pharmacology), Ascomycota (drug effects), Biological Products (chemistry), Biological Products (pharmacology), Crop Protection (methods), Drug Discovery (MeSH), Fusarium (drug effects), Microbial Sensitivity Tests (MeSH), Mitosporic Fungi (drug effects), Molecular Structure (MeSH), Phytophthora (drug effects), Pyrazoles (chemistry), Pyrazoles (pharmacology), Resins, Plant (chemistry), Resins, Plant (pharmacology), Structure-Activity Relationship (MeSH), Thiophenes (chemistry), Thiophenes (pharmacology).
- MESH :
- chemical , chemical synthesis : Amides.
- chemical , chemistry : Antifungal Agents, Biological Products, Pyrazoles, Resins, Plant, Thiophenes.
- chemical , pharmacology : Antifungal Agents, Biological Products, Pyrazoles, Resins, Plant, Thiophenes.
- drug effects : Ascomycota, Fusarium, Mitosporic Fungi, Phytophthora.
- methods : Crop Protection.
- Drug Discovery, Microbial Sensitivity Tests, Molecular Structure, Structure-Activity Relationship.
Abstract
In the current work, we synthesized two series of dehydroabietyl amide derivatives from natural product rosin and evaluated their antifungal effects on Valsa mali, Phytophthora capsici, Botrytis cinerea, Sclerotinia sclerotiorum, and Fusarium oxysporum. In vitro and in vivo antifungal activities results indicated that rosin-based amide compounds containing thiophene heterocycles had better inhibitory effects on B. cinerea. In particular, compound 5b (5-fluoro-2-thiophene dehydroabietyl amide) exhibited the excellent antifungal properties against B. cinerea with an EC50 of 0.490 mg/L, which was lower compared to the positive control penthiopyrad (0.562 mg/L). Physiological and biochemical studies showed that the primary action mechanism of compound 5b on B. cinerea changes mycelial morphology, increases cell membrane permeability, and inhibits the TCA pathway in respiratory metabolism. Furthermore, QSAR and SAR studies revealed that charge distribution of rosin-based amides derivatives have a key role in the antifungal activity through the hydrogen bonding, conjugation, and electrostatic interaction between the compounds and the receptors of the target. To sum up, this study contributes to the development of rosin-based antifungal agents with a novel structure and preferable biological activity.
DOI: 10.1021/acs.jafc.0c00562
PubMed: 32191457
Affiliations:
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Yangling, Shaanxi 712100, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Forestry, Northwest A&F University, Yangling, Shaanxi 712100</wicri:regionArea><wicri:noRegion>Shaanxi 712100</wicri:noRegion></affiliation></author><author><name sortKey="Shang, Shibin" sort="Shang, Shibin" uniqKey="Shang S" first="Shibin" last="Shang">Shibin Shang</name><affiliation wicri:level="1"><nlm:affiliation>Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing, Jiangsu 210042, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing, Jiangsu 210042</wicri:regionArea><wicri:noRegion>Jiangsu 210042</wicri:noRegion></affiliation></author><author><name sortKey="Song, Zhanqian" sort="Song, Zhanqian" uniqKey="Song Z" first="Zhanqian" last="Song">Zhanqian Song</name><affiliation wicri:level="1"><nlm:affiliation>Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing, Jiangsu 210042, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing, Jiangsu 210042</wicri:regionArea><wicri:noRegion>Jiangsu 210042</wicri:noRegion></affiliation></author><author><name sortKey="Song, Jie" sort="Song, Jie" uniqKey="Song J" first="Jie" last="Song">Jie Song</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry and Biochemistry, University of Michigan-Flint, Flint, Michigan 48502, United States.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry and Biochemistry, University of Michigan-Flint, Flint, Michigan 48502</wicri:regionArea><wicri:noRegion>Michigan 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People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Forestry, Northwest A&F University, Yangling, Shaanxi 712100</wicri:regionArea><wicri:noRegion>Shaanxi 712100</wicri:noRegion></affiliation></author><author><name sortKey="Wu, Chengyu" sort="Wu, Chengyu" uniqKey="Wu C" first="Chengyu" last="Wu">Chengyu Wu</name><affiliation wicri:level="1"><nlm:affiliation>College of Forestry, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Forestry, Northwest A&F University, Yangling, Shaanxi 712100</wicri:regionArea><wicri:noRegion>Shaanxi 712100</wicri:noRegion></affiliation></author><author><name sortKey="Hao, Jin" sort="Hao, Jin" uniqKey="Hao J" first="Jin" last="Hao">Jin Hao</name><affiliation wicri:level="1"><nlm:affiliation>College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100</wicri:regionArea><wicri:noRegion>Shaanxi 712100</wicri:noRegion></affiliation></author><author><name sortKey="Gao, Yanqing" sort="Gao, Yanqing" uniqKey="Gao Y" first="Yanqing" last="Gao">Yanqing Gao</name><affiliation wicri:level="1"><nlm:affiliation>College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100</wicri:regionArea><wicri:noRegion>Shaanxi 712100</wicri:noRegion></affiliation></author><author><name sortKey="He, Xiaohua" sort="He, Xiaohua" uniqKey="He X" first="Xiaohua" last="He">Xiaohua He</name><affiliation wicri:level="1"><nlm:affiliation>College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100</wicri:regionArea><wicri:noRegion>Shaanxi 712100</wicri:noRegion></affiliation></author><author><name sortKey="Li, Jian" sort="Li, Jian" uniqKey="Li J" first="Jian" last="Li">Jian Li</name><affiliation wicri:level="1"><nlm:affiliation>College of Forestry, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Forestry, Northwest A&F University, Yangling, Shaanxi 712100</wicri:regionArea><wicri:noRegion>Shaanxi 712100</wicri:noRegion></affiliation></author><author><name sortKey="Shang, Shibin" sort="Shang, Shibin" uniqKey="Shang S" first="Shibin" last="Shang">Shibin Shang</name><affiliation wicri:level="1"><nlm:affiliation>Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing, Jiangsu 210042, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing, Jiangsu 210042</wicri:regionArea><wicri:noRegion>Jiangsu 210042</wicri:noRegion></affiliation></author><author><name sortKey="Song, Zhanqian" sort="Song, Zhanqian" uniqKey="Song Z" first="Zhanqian" last="Song">Zhanqian Song</name><affiliation wicri:level="1"><nlm:affiliation>Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing, Jiangsu 210042, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing, Jiangsu 210042</wicri:regionArea><wicri:noRegion>Jiangsu 210042</wicri:noRegion></affiliation></author><author><name sortKey="Song, Jie" sort="Song, Jie" uniqKey="Song J" first="Jie" last="Song">Jie Song</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry and Biochemistry, University of Michigan-Flint, Flint, Michigan 48502, United States.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry and Biochemistry, University of Michigan-Flint, Flint, Michigan 48502</wicri:regionArea><wicri:noRegion>Michigan 48502</wicri:noRegion></affiliation></author></analytic><series><title level="j">Journal of agricultural and food chemistry</title><idno type="eISSN">1520-5118</idno><imprint><date when="2020" type="published">2020</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Amides (chemical synthesis)</term><term>Antifungal Agents (chemistry)</term><term>Antifungal Agents (pharmacology)</term><term>Ascomycota (drug effects)</term><term>Biological Products (chemistry)</term><term>Biological Products (pharmacology)</term><term>Crop Protection (methods)</term><term>Drug Discovery (MeSH)</term><term>Fusarium (drug effects)</term><term>Microbial Sensitivity Tests (MeSH)</term><term>Mitosporic Fungi (drug effects)</term><term>Molecular Structure (MeSH)</term><term>Phytophthora (drug effects)</term><term>Pyrazoles (chemistry)</term><term>Pyrazoles (pharmacology)</term><term>Resins, Plant (chemistry)</term><term>Resins, Plant (pharmacology)</term><term>Structure-Activity Relationship (MeSH)</term><term>Thiophenes (chemistry)</term><term>Thiophenes (pharmacology)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Amides (synthèse chimique)</term><term>Antifongiques (composition chimique)</term><term>Antifongiques (pharmacologie)</term><term>Ascomycota (effets des médicaments et des substances chimiques)</term><term>Deuteromycota (effets des médicaments et des substances chimiques)</term><term>Découverte de médicament (MeSH)</term><term>Fusarium (effets des médicaments et des substances chimiques)</term><term>Phytophthora (effets des médicaments et des substances chimiques)</term><term>Produits biologiques (composition chimique)</term><term>Produits biologiques (pharmacologie)</term><term>Protection des cultures (méthodes)</term><term>Pyrazoles (composition chimique)</term><term>Pyrazoles (pharmacologie)</term><term>Relation structure-activité (MeSH)</term><term>Résines végétales (composition chimique)</term><term>Résines végétales (pharmacologie)</term><term>Structure moléculaire (MeSH)</term><term>Tests de sensibilité microbienne (MeSH)</term><term>Thiophènes (composition chimique)</term><term>Thiophènes (pharmacologie)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Amides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antifungal Agents</term><term>Biological Products</term><term>Pyrazoles</term><term>Resins, Plant</term><term>Thiophenes</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antifungal Agents</term><term>Biological Products</term><term>Pyrazoles</term><term>Resins, Plant</term><term>Thiophenes</term></keywords><keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Antifongiques</term><term>Produits biologiques</term><term>Pyrazoles</term><term>Résines végétales</term><term>Thiophènes</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Ascomycota</term><term>Fusarium</term><term>Mitosporic Fungi</term><term>Phytophthora</term></keywords><keywords scheme="MESH" qualifier="effets des médicaments et des substances chimiques" xml:lang="fr"><term>Ascomycota</term><term>Deuteromycota</term><term>Fusarium</term><term>Phytophthora</term></keywords><keywords scheme="MESH" qualifier="methods" xml:lang="en"><term>Crop Protection</term></keywords><keywords scheme="MESH" qualifier="méthodes" xml:lang="fr"><term>Protection des cultures</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antifongiques</term><term>Produits biologiques</term><term>Pyrazoles</term><term>Résines végétales</term><term>Thiophènes</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Amides</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Drug Discovery</term><term>Microbial Sensitivity Tests</term><term>Molecular Structure</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Découverte de médicament</term><term>Relation structure-activité</term><term>Structure moléculaire</term><term>Tests de sensibilité microbienne</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">In the current work, we synthesized two series of dehydroabietyl amide derivatives from natural product rosin and evaluated their antifungal effects on <i>Valsa mali</i>, <i>Phytophthora capsici</i>, <i>Botrytis cinerea</i>, <i>Sclerotinia sclerotiorum</i>, and <i>Fusarium oxysporum</i>. <i>In vitro</i> and <i>in vivo</i> antifungal activities results indicated that rosin-based amide compounds containing thiophene heterocycles had better inhibitory effects on <i>B. cinerea</i>. In particular, compound <b>5b</b> (5-fluoro-2-thiophene dehydroabietyl amide) exhibited the excellent antifungal properties against <i>B. cinerea</i> with an EC<sub>50</sub> of 0.490 mg/L, which was lower compared to the positive control penthiopyrad (0.562 mg/L). Physiological and biochemical studies showed that the primary action mechanism of compound <b>5b</b> on <i>B. cinerea</i> changes mycelial morphology, increases cell membrane permeability, and inhibits the TCA pathway in respiratory metabolism. Furthermore, QSAR and SAR studies revealed that charge distribution of rosin-based amides derivatives have a key role in the antifungal activity through the hydrogen bonding, conjugation, and electrostatic interaction between the compounds and the receptors of the target. To sum up, this study contributes to the development of rosin-based antifungal agents with a novel structure and preferable biological activity.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">32191457</PMID><DateCompleted><Year>2020</Year><Month>11</Month><Day>10</Day></DateCompleted><DateRevised><Year>2020</Year><Month>11</Month><Day>10</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-5118</ISSN><JournalIssue CitedMedium="Internet"><Volume>68</Volume><Issue>14</Issue><PubDate><Year>2020</Year><Month>Apr</Month><Day>08</Day></PubDate></JournalIssue><Title>Journal of agricultural and food chemistry</Title><ISOAbbreviation>J Agric Food Chem</ISOAbbreviation></Journal><ArticleTitle>Antifungal Application of Rosin Derivatives from Renewable Pine Resin in Crop Protection.</ArticleTitle><Pagination><MedlinePgn>4144-4154</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/acs.jafc.0c00562</ELocationID><Abstract><AbstractText>In the current work, we synthesized two series of dehydroabietyl amide derivatives from natural product rosin and evaluated their antifungal effects on <i>Valsa mali</i>, <i>Phytophthora capsici</i>, <i>Botrytis cinerea</i>, <i>Sclerotinia sclerotiorum</i>, and <i>Fusarium oxysporum</i>. <i>In vitro</i> and <i>in vivo</i> antifungal activities results indicated that rosin-based amide compounds containing thiophene heterocycles had better inhibitory effects on <i>B. cinerea</i>. In particular, compound <b>5b</b> (5-fluoro-2-thiophene dehydroabietyl amide) exhibited the excellent antifungal properties against <i>B. cinerea</i> with an EC<sub>50</sub> of 0.490 mg/L, which was lower compared to the positive control penthiopyrad (0.562 mg/L). Physiological and biochemical studies showed that the primary action mechanism of compound <b>5b</b> on <i>B. cinerea</i> changes mycelial morphology, increases cell membrane permeability, and inhibits the TCA pathway in respiratory metabolism. Furthermore, QSAR and SAR studies revealed that charge distribution of rosin-based amides derivatives have a key role in the antifungal activity through the hydrogen bonding, conjugation, and electrostatic interaction between the compounds and the receptors of the target. To sum up, this study contributes to the development of rosin-based antifungal agents with a novel structure and preferable biological activity.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Tao</LastName><ForeName>Pan</ForeName><Initials>P</Initials><AffiliationInfo><Affiliation>College of Forestry, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Wu</LastName><ForeName>Chengyu</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>College of Forestry, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Hao</LastName><ForeName>Jin</ForeName><Initials>J</Initials><AffiliationInfo><Affiliation>College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Gao</LastName><ForeName>Yanqing</ForeName><Initials>Y</Initials><AffiliationInfo><Affiliation>College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>He</LastName><ForeName>Xiaohua</ForeName><Initials>X</Initials><AffiliationInfo><Affiliation>College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Li</LastName><ForeName>Jian</ForeName><Initials>J</Initials><Identifier Source="ORCID">http://orcid.org/0000-0002-7378-8658</Identifier><AffiliationInfo><Affiliation>College of Forestry, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Shang</LastName><ForeName>Shibin</ForeName><Initials>S</Initials><Identifier Source="ORCID">http://orcid.org/0000-0002-8665-769X</Identifier><AffiliationInfo><Affiliation>Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing, Jiangsu 210042, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Song</LastName><ForeName>Zhanqian</ForeName><Initials>Z</Initials><AffiliationInfo><Affiliation>Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing, Jiangsu 210042, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Song</LastName><ForeName>Jie</ForeName><Initials>J</Initials><AffiliationInfo><Affiliation>Department of Chemistry and Biochemistry, University of Michigan-Flint, Flint, Michigan 48502, United States.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2020</Year><Month>03</Month><Day>25</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="D000577">Amides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000935">Antifungal Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D001688">Biological Products</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D011720">Pyrazoles</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D012116">Resins, Plant</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D013876">Thiophenes</NameOfSubstance></Chemical><Chemical><RegistryNumber>FAT7900E5H</RegistryNumber><NameOfSubstance UI="C539106">penthiopyrad</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000577" MajorTopicYN="N">Amides</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D000935" MajorTopicYN="N">Antifungal Agents</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D001203" MajorTopicYN="N">Ascomycota</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D001688" MajorTopicYN="N">Biological Products</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D000069601" MajorTopicYN="N">Crop Protection</DescriptorName><QualifierName UI="Q000379" MajorTopicYN="Y">methods</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D055808" MajorTopicYN="N">Drug Discovery</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D005670" MajorTopicYN="N">Fusarium</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D008826" MajorTopicYN="N">Microbial Sensitivity Tests</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D003904" MajorTopicYN="N">Mitosporic Fungi</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D010838" MajorTopicYN="N">Phytophthora</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D011720" MajorTopicYN="N">Pyrazoles</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D012116" MajorTopicYN="N">Resins, Plant</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D013876" MajorTopicYN="N">Thiophenes</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">QSAR</Keyword><Keyword MajorTopicYN="N">action mechanism</Keyword><Keyword MajorTopicYN="N">amide</Keyword><Keyword MajorTopicYN="N">antifungal activity</Keyword><Keyword MajorTopicYN="N">rosin</Keyword><Keyword MajorTopicYN="N">thiophene heterocycle</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2020</Year><Month>3</Month><Day>20</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2020</Year><Month>11</Month><Day>11</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2020</Year><Month>3</Month><Day>20</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">32191457</ArticleId><ArticleId IdType="doi">10.1021/acs.jafc.0c00562</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>République populaire de Chine</li><li>États-Unis</li></country></list><tree><country name="République populaire de Chine"><noRegion><name sortKey="Tao, Pan" sort="Tao, Pan" uniqKey="Tao P" first="Pan" last="Tao">Pan Tao</name></noRegion><name sortKey="Gao, Yanqing" sort="Gao, Yanqing" uniqKey="Gao Y" first="Yanqing" last="Gao">Yanqing Gao</name><name sortKey="Hao, Jin" sort="Hao, Jin" uniqKey="Hao J" first="Jin" last="Hao">Jin Hao</name><name sortKey="He, Xiaohua" sort="He, Xiaohua" uniqKey="He X" first="Xiaohua" last="He">Xiaohua He</name><name sortKey="Li, Jian" sort="Li, Jian" uniqKey="Li J" first="Jian" last="Li">Jian Li</name><name sortKey="Shang, Shibin" sort="Shang, Shibin" uniqKey="Shang S" first="Shibin" last="Shang">Shibin Shang</name><name sortKey="Song, Zhanqian" sort="Song, Zhanqian" uniqKey="Song Z" first="Zhanqian" last="Song">Zhanqian Song</name><name sortKey="Wu, Chengyu" sort="Wu, Chengyu" uniqKey="Wu C" first="Chengyu" last="Wu">Chengyu Wu</name></country><country name="États-Unis"><noRegion><name sortKey="Song, Jie" sort="Song, Jie" uniqKey="Song J" first="Jie" last="Song">Jie Song</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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