Synthesis and in Vitro Antifungal Activity against Botrytis cinerea of Geranylated Phenols and Their Phenyl Acetate Derivatives.
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.
Departamento de Química, Universidad Técnica Federico Santa María, Valparaíso 2340000, Chile. maria.chavez@usm.cl.
María I
MI
Chávez
Departamento de Química, Universidad Técnica Federico Santa María, Valparaíso 2340000, Chile. mauricio.sotoc.13@sansano.usm.cl.
Mauricio
M
Soto
Departamento de Química, Universidad Técnica Federico Santa María, Valparaíso 2340000, Chile. lautaro.taborga@usm.cl.
Lautaro
L
Taborga
Departamento de Química, Universidad Técnica Federico Santa María, Valparaíso 2340000, Chile. katy.diaz@usm.cl.
Katy
K
Díaz
Instituto de Ciencias Químicas Aplicadas, Facultad de Ingeniería, Universidad Autónoma de Chile, Santiago 8910339, Chile. andres.olea@uautonoma.cl.
Andrés F
AF
Olea
Facultad de Ingeniería, Universidad de Chile, Santiago 8370448, Chile. camila.bay.ch@gmail.com.
Camila
C
Bay
Facultad de Medicina, Hontaneda 2664, Universidad de Valparaíso, Valparaíso 2340000, Chile. hugo.pena@uv.cl.
Hugo
H
Peña-Cortés
Departamento de Química, Universidad Técnica Federico Santa María, Valparaíso 2340000, Chile. luis.espinozac@usm.cl.
Luis
L
Espinoza
D000085:Acetates / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D000080462:Acyclic Monoterpenes; D020171:Botrytis / Q000187:drug effects* / Q000254:growth & development*; D005659:Fungicides, Industrial / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D055772:Green Chemistry Technology; D025282:Mycelium / Q000187:drug effects / Q000254:growth & development; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013729:Terpenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology
D000085:Acetates; D000080462:Acyclic Monoterpenes; D005659:Fungicides, Industrial; D010636:Phenols; D013729:Terpenes; C570634:phenyl acetate; C007836:geraniol
Botrytis cinerea; antifungal activity; geranylphenols; green chemistry; synthesis