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Int. J. Mol. Sci. 2015, 16(8), 19130-19152; doi:10.3390/ijms160819130

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

1
Departamento de Química, Universidad Técnica Federico Santa María, Valparaíso 2340000, Chile
2
Instituto de Ciencias Químicas Aplicadas, Facultad de Ingeniería, Universidad Autónoma de Chile, Santiago 8910339, Chile
3
Facultad de Ingeniería, Universidad de Chile, Santiago 8370448, Chile
4
Facultad de Medicina, Hontaneda 2664, Universidad de Valparaíso, Valparaíso 2340000, Chile
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Academic Editor: Fabio Marinelli
Received: 21 July 2015 / Accepted: 10 August 2015 / Published: 14 August 2015
(This article belongs to the Section Green Chemistry)
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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. View Full-Text
Keywords: Botrytis cinerea; antifungal activity; geranylphenols; synthesis; green chemistry Botrytis cinerea; antifungal activity; geranylphenols; synthesis; green chemistry
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Chávez, M.I.; Soto, M.; Taborga, L.; Díaz, K.; Olea, A.F.; Bay, C.; Peña-Cortés, H.; Espinoza, L. Synthesis and in Vitro Antifungal Activity against Botrytis cinerea of Geranylated Phenols and Their Phenyl Acetate Derivatives. Int. J. Mol. Sci. 2015, 16, 19130-19152.

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