Characterization of the Fungitoxic Activity on Botrytis cinerea of N-phenyl-driman-9-carboxamides

A total of 12 compounds were synthesized from the natural sesquiterpene (-) drimenol (compounds 4 to 15). The synthesized compounds corresponded to N-phenyl-driman-9-carboxamide derivatives, similar to some fungicides that inhibit the electron-transport chain. Their structures were characterized and...

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Autores principales: Melo, Ricardo, Armstrong, Verónica, Navarro, Freddy, Castro, Paulo, Mendoza, Leonora, Cotoras, Milena
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8623464/
https://www.ncbi.nlm.nih.gov/pubmed/34829191
http://dx.doi.org/10.3390/jof7110902
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author Melo, Ricardo
Armstrong, Verónica
Navarro, Freddy
Castro, Paulo
Mendoza, Leonora
Cotoras, Milena
author_facet Melo, Ricardo
Armstrong, Verónica
Navarro, Freddy
Castro, Paulo
Mendoza, Leonora
Cotoras, Milena
author_sort Melo, Ricardo
collection PubMed
description A total of 12 compounds were synthesized from the natural sesquiterpene (-) drimenol (compounds 4 to 15). The synthesized compounds corresponded to N-phenyl-driman-9-carboxamide derivatives, similar to some fungicides that inhibit the electron-transport chain. Their structures were characterized and confirmed by (1)H NMR, (13)C NMR spectroscopy, and mass spectrometry. Compounds 5 to 15 corresponded to novel compounds. The effect of the compounds on the mycelial growth of Botrytis cinerea was evaluated. Methoxylated and chlorinated compounds in the aromatic ring (compounds 6, 7, 12, and 13) exhibited the highest antifungal activity with IC(50) values between 0.20 and 0.26 mM. On the other hand, the effect on conidial germination of B. cinerea of one methoxylated compound (6) and one chlorinated compound (7) was analyzed, and no inhibition was observed. Additionally, compound 7 decreased 36% the rate of oxygen consumption by germinating conidia.
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spelling pubmed-86234642021-11-27 Characterization of the Fungitoxic Activity on Botrytis cinerea of N-phenyl-driman-9-carboxamides Melo, Ricardo Armstrong, Verónica Navarro, Freddy Castro, Paulo Mendoza, Leonora Cotoras, Milena J Fungi (Basel) Article A total of 12 compounds were synthesized from the natural sesquiterpene (-) drimenol (compounds 4 to 15). The synthesized compounds corresponded to N-phenyl-driman-9-carboxamide derivatives, similar to some fungicides that inhibit the electron-transport chain. Their structures were characterized and confirmed by (1)H NMR, (13)C NMR spectroscopy, and mass spectrometry. Compounds 5 to 15 corresponded to novel compounds. The effect of the compounds on the mycelial growth of Botrytis cinerea was evaluated. Methoxylated and chlorinated compounds in the aromatic ring (compounds 6, 7, 12, and 13) exhibited the highest antifungal activity with IC(50) values between 0.20 and 0.26 mM. On the other hand, the effect on conidial germination of B. cinerea of one methoxylated compound (6) and one chlorinated compound (7) was analyzed, and no inhibition was observed. Additionally, compound 7 decreased 36% the rate of oxygen consumption by germinating conidia. MDPI 2021-10-26 /pmc/articles/PMC8623464/ /pubmed/34829191 http://dx.doi.org/10.3390/jof7110902 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Melo, Ricardo
Armstrong, Verónica
Navarro, Freddy
Castro, Paulo
Mendoza, Leonora
Cotoras, Milena
Characterization of the Fungitoxic Activity on Botrytis cinerea of N-phenyl-driman-9-carboxamides
title Characterization of the Fungitoxic Activity on Botrytis cinerea of N-phenyl-driman-9-carboxamides
title_full Characterization of the Fungitoxic Activity on Botrytis cinerea of N-phenyl-driman-9-carboxamides
title_fullStr Characterization of the Fungitoxic Activity on Botrytis cinerea of N-phenyl-driman-9-carboxamides
title_full_unstemmed Characterization of the Fungitoxic Activity on Botrytis cinerea of N-phenyl-driman-9-carboxamides
title_short Characterization of the Fungitoxic Activity on Botrytis cinerea of N-phenyl-driman-9-carboxamides
title_sort characterization of the fungitoxic activity on botrytis cinerea of n-phenyl-driman-9-carboxamides
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8623464/
https://www.ncbi.nlm.nih.gov/pubmed/34829191
http://dx.doi.org/10.3390/jof7110902
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