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Title

Synthesis and in Vitro Antifungal Activity against Botrytis cinerea of Geranylated Phenols and Their Phenyl Acetate Derivatives.

Authors

Chávez, María I.; Soto, Mauricio; Taborga, Lautaro; Díaz, Katy; Olea, Andrés F.; Bay, Camila; Peña-Cortés, Hugo; Espinoza, Luis

Abstract

The inhibitory effects on the mycelial growth of plant pathogen Botritys cinerea have been evaluated for a series of geranylphenols substituted with one, two and three methoxy groups in the aromatic ring. The results show that the antifungal activity depends on the structure of the geranylphenols, increasing from 40% to 90% by increasing the number of methoxy groups. On the other hand, the acetylation of the -OH group induces a change of activity that depends on the number of methoxy groups. The biological activity of digeranyl derivatives is lower than that exhibited by the respective monogeranyl compound. All tested geranylphenols have been synthesized by direct coupling of geraniol and the respective phenol. The effect of solvent on yields and product distribution is discussed. For monomethoxyphenols the reaction gives better yields when acetonitrile is used as a solvent and AgNO3 is used as a secondary catalyst. However, for di- and trimethoxyphenols the reaction proceeds only in dioxane.

Subjects

PHENYLACETATES; BOTRYTIS cinerea; AROMATIC compounds; ANTISEPTICS; BOTRYTIS diseases; BOTRYTIS

Publication

International Journal of Molecular Sciences, 2015, Vol 16, Issue 8, p19130

ISSN

1661-6596

Publication type

Academic Journal

DOI

10.3390/ijms160819130

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