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Article

Synthesis and In Vitro Growth Inhibition of 2-Allylphenol Derivatives Against Phythopthora cinnamomi Rands

1
Instituto de Ciencias Químicas Aplicadas, Facultad de Ingeniería, Universidad Autónoma de Chile, El Llano Subercaseaux 2801, Santiago CP 8900000, Chile
2
Departamento de Química, Universidad Técnica Federico Santa María, Avenida España 1680, Valparaíso CP 2340000, Chile
3
Departamento de Ciencias Químicas, Facultad de Ciencias Exactas, Universidad Andrés Bello, Quillota 910, Viña del Mar CP 2520000, Chile
4
Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Avenida Universidad 330, Curauma, Valparaíso CP 2340000, Chile
*
Authors to whom correspondence should be addressed.
Molecules 2019, 24(22), 4196; https://doi.org/10.3390/molecules24224196
Received: 3 October 2019 / Revised: 11 November 2019 / Accepted: 16 November 2019 / Published: 19 November 2019
Phytophthora cinnamomi is a phytopathogen that causes extensive damage in different crops, and therefore, produces important economic losses all around the world. Chemical fungicides are a key factor for the control of this disease. However, ecological and environmental considerations, as well as the appearance of strains that are resistant to commercial fungicides, have prompted the quest for new antifungal agents which are of low ecological impact. In this work, a series of new 2-allylphenol derivatives was synthesized, and their structures were confirmed by FT-IR, NMR, and MS. Some of the synthesized compounds, more specifically nitro derivatives, exhibit strong growth inhibition of P. cinnamomi with EC50 as low as 10.0 µg/mL. This level of activity is similar to that exhibited by METALAXYL MZ 58 WP, a commonly-used commercial fungicide; therefore, these compounds might be of agricultural interest due to their potential use as fungicides against P. cinnamomi. The results indicate that this activity depends on the chemical structures of the 2-allylphenol derivatives, and that it is strongly enhanced in molecules where nitro and hydroxyl groups adopt a -para configuration. These effects are discussed in terms of the electronic distribution of the aromatic ring induced by substituent groups. View Full-Text
Keywords: pest control; Phytophthora cinnamomi; fungicide; 2-allylphenol; structure–activity relationship pest control; Phytophthora cinnamomi; fungicide; 2-allylphenol; structure–activity relationship
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MDPI and ACS Style

Olea, A.F.; Espinoza, L.; Sedan, C.; Thomas, M.; Martínez, R.; Mellado, M.; Carrasco, H.; Díaz, K. Synthesis and In Vitro Growth Inhibition of 2-Allylphenol Derivatives Against Phythopthora cinnamomi Rands. Molecules 2019, 24, 4196. https://doi.org/10.3390/molecules24224196

AMA Style

Olea AF, Espinoza L, Sedan C, Thomas M, Martínez R, Mellado M, Carrasco H, Díaz K. Synthesis and In Vitro Growth Inhibition of 2-Allylphenol Derivatives Against Phythopthora cinnamomi Rands. Molecules. 2019; 24(22):4196. https://doi.org/10.3390/molecules24224196

Chicago/Turabian Style

Olea, Andrés F., Luis Espinoza, Claudia Sedan, Mario Thomas, Rolando Martínez, Marco Mellado, Héctor Carrasco, and Katy Díaz. 2019. "Synthesis and In Vitro Growth Inhibition of 2-Allylphenol Derivatives Against Phythopthora cinnamomi Rands" Molecules 24, no. 22: 4196. https://doi.org/10.3390/molecules24224196

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