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Antifungal Application of Rosin Derivatives from Renewable Pine Resin in Crop Protection.
- Source :
-
Journal of agricultural and food chemistry [J Agric Food Chem] 2020 Apr 08; Vol. 68 (14), pp. 4144-4154. Date of Electronic Publication: 2020 Mar 25. - Publication Year :
- 2020
-
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 EC <subscript>50</subscript> 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.
- Subjects :
- Antifungal Agents pharmacology
Ascomycota drug effects
Biological Products pharmacology
Drug Discovery
Fusarium drug effects
Microbial Sensitivity Tests
Mitosporic Fungi drug effects
Molecular Structure
Phytophthora drug effects
Pyrazoles chemistry
Pyrazoles pharmacology
Resins, Plant pharmacology
Structure-Activity Relationship
Thiophenes chemistry
Thiophenes pharmacology
Amides chemical synthesis
Antifungal Agents chemistry
Biological Products chemistry
Crop Protection methods
Resins, Plant chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1520-5118
- Volume :
- 68
- Issue :
- 14
- Database :
- MEDLINE
- Journal :
- Journal of agricultural and food chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 32191457
- Full Text :
- https://doi.org/10.1021/acs.jafc.0c00562