In Vitro Antifungal Activity and Toxicity of Dihydrocarvone-Hybrid Derivatives against <i>Monilinia fructicola</i>
Katy Díaz,
Enrique Werner,
Ximena Besoain,
Susana Flores,
Viviana Donoso,
Bastian Said,
Nelson Caro,
Ernesto Vega,
Iván Montenegro,
Alejandro Madrid
Affiliations
Katy Díaz
Departamento de Química, Universidad Técnica Federico Santa María, Av. España N° 1680, Valparaíso 2340000, Chile
Enrique Werner
Departamento de Ciencias Básicas, Campus Fernando May, Universidad del Bío-Bío, Avda. Andrés Bello 720, Casilla 447, Chillán 3780000, Chile
Ximena Besoain
Escuela de Agronomía, Pontificia Universidad Católica de Valparaíso, San Francisco s/n La Palma, Quillota 2260000, Chile
Susana Flores
Laboratorio de Productos Naturales y Síntesis Orgánica (LPNSO), Departamento de Química, Facultad de Ciencias Naturales y Exactas, Universidad de Playa Ancha, Avda. Leopoldo Carvallo 270, Playa Ancha, Valparaíso 2340000, Chile
Viviana Donoso
Laboratorio de Productos Naturales y Síntesis Orgánica (LPNSO), Departamento de Química, Facultad de Ciencias Naturales y Exactas, Universidad de Playa Ancha, Avda. Leopoldo Carvallo 270, Playa Ancha, Valparaíso 2340000, Chile
Bastian Said
Departamento de Química, Universidad Técnica Federico Santa María, Av. Santa María 6400, Santiago 7630000, Chile
Nelson Caro
Centro de Investigación Australbiotech, Universidad Santo Tomás, Avda. Ejército 146, Santiago 8320000, Chile
Ernesto Vega
Departamento Laboratorios y Estaciones Cuarentenarias, Servicio Agrícola y Ganadero, Ruta 68 # (Km. 12), Pudahuel 9020000, Chile
Iván Montenegro
Escuela de Obstetricia y Puericultura, Facultad de Medicina, Universidad de Valparaíso, Angamos 655, Reñaca 2520000, Chile
Alejandro Madrid
Laboratorio de Productos Naturales y Síntesis Orgánica (LPNSO), Departamento de Química, Facultad de Ciencias Naturales y Exactas, Universidad de Playa Ancha, Avda. Leopoldo Carvallo 270, Playa Ancha, Valparaíso 2340000, Chile
The aim of this study was to synthesize a series of novel and known dihydrocarvone-hybrid derivatives (2–9) and to evaluate mycelial growth activity of hybrid molecules against two strains of Monilinia fructicola, as well as their toxicity. Dihydrocarvone-hybrid derivatives have been synthesized under sonication conditions and characterized by FTIR, NMR, and HRMS. Antifungal efficacy against both strains of M. fructicola was determined by half maximal effective concentration (EC50) and toxicity using the brine shrimp lethality test (BSLT). Among the synthesized compounds, 7 and 8 showed the best activity against both strains of M. fructicola with EC50 values of 148.1 and 145.9 µg/mL for strain 1 and 18.1 and 15.7 µg/mL for strain 2, respectively, compared to BC 1000® (commercial organic fungicide) but lower than Mystic® 520 SC. However, these compounds showed low toxicity values, 910 and 890 µg/mL, respectively, compared to Mystic® 520 SC, which was highly toxic. Based on the results, these hybrid compounds could be considered for the development of more active, less toxic, and environmentally friendly antifungal agents against phytopathogenic fungi.