Synthesis and In Vitro Growth Inhibition of 2-Allylphenol Derivatives Against <i>Phythopthora cinnamomi</i> Rands
<i>Phytophthora cinnamomi</i> 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 considerat...
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| Format: | Article |
| Language: | English |
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MDPI AG
2019-11-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/22/4196 |
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| author | Andrés F. Olea Luis Espinoza Claudia Sedan Mario Thomas Rolando Martínez Marco Mellado Héctor Carrasco Katy Díaz |
| author_facet | Andrés F. Olea Luis Espinoza Claudia Sedan Mario Thomas Rolando Martínez Marco Mellado Héctor Carrasco Katy Díaz |
| author_sort | Andrés F. Olea |
| collection | DOAJ |
| description | <i>Phytophthora cinnamomi</i> 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 <i>P. cinnamomi</i> with EC<sub>50</sub> as low as 10.0 µg/mL. This level of activity is similar to that exhibited by <i>METALAXYL MZ 58 WP</i>, a commonly-used commercial fungicide; therefore, these compounds might be of agricultural interest due to their potential use as fungicides against <i>P. cinnamomi</i>. 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. |
| first_indexed | 2024-12-22T04:10:20Z |
| format | Article |
| id | doaj.art-48e2fc371b0740ed9299d62789dfa437 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-22T04:10:20Z |
| publishDate | 2019-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-48e2fc371b0740ed9299d62789dfa4372022-12-21T18:39:32ZengMDPI AGMolecules1420-30492019-11-012422419610.3390/molecules24224196molecules24224196Synthesis and In Vitro Growth Inhibition of 2-Allylphenol Derivatives Against <i>Phythopthora cinnamomi</i> RandsAndrés F. Olea0Luis Espinoza1Claudia Sedan2Mario Thomas3Rolando Martínez4Marco Mellado5Héctor Carrasco6Katy Díaz7Instituto de Ciencias Químicas Aplicadas, Facultad de Ingeniería, Universidad Autónoma de Chile, El Llano Subercaseaux 2801, Santiago CP 8900000, ChileDepartamento de Química, Universidad Técnica Federico Santa María, Avenida España 1680, Valparaíso CP 2340000, ChileDepartamento de Ciencias Químicas, Facultad de Ciencias Exactas, Universidad Andrés Bello, Quillota 910, Viña del Mar CP 2520000, ChileDepartamento de Ciencias Químicas, Facultad de Ciencias Exactas, Universidad Andrés Bello, Quillota 910, Viña del Mar CP 2520000, ChileDepartamento de Ciencias Químicas, Facultad de Ciencias Exactas, Universidad Andrés Bello, Quillota 910, Viña del Mar CP 2520000, ChileInstituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Avenida Universidad 330, Curauma, Valparaíso CP 2340000, ChileInstituto de Ciencias Químicas Aplicadas, Facultad de Ingeniería, Universidad Autónoma de Chile, El Llano Subercaseaux 2801, Santiago CP 8900000, ChileDepartamento de Química, Universidad Técnica Federico Santa María, Avenida España 1680, Valparaíso CP 2340000, Chile<i>Phytophthora cinnamomi</i> 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 <i>P. cinnamomi</i> with EC<sub>50</sub> as low as 10.0 µg/mL. This level of activity is similar to that exhibited by <i>METALAXYL MZ 58 WP</i>, a commonly-used commercial fungicide; therefore, these compounds might be of agricultural interest due to their potential use as fungicides against <i>P. cinnamomi</i>. 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.https://www.mdpi.com/1420-3049/24/22/4196pest control<i>phytophthora cinnamomi</i>fungicide2-allylphenolstructure–activity relationship |
| spellingShingle | Andrés F. Olea Luis Espinoza Claudia Sedan Mario Thomas Rolando Martínez Marco Mellado Héctor Carrasco Katy Díaz Synthesis and In Vitro Growth Inhibition of 2-Allylphenol Derivatives Against <i>Phythopthora cinnamomi</i> Rands Molecules pest control <i>phytophthora cinnamomi</i> fungicide 2-allylphenol structure–activity relationship |
| title | Synthesis and In Vitro Growth Inhibition of 2-Allylphenol Derivatives Against <i>Phythopthora cinnamomi</i> Rands |
| title_full | Synthesis and In Vitro Growth Inhibition of 2-Allylphenol Derivatives Against <i>Phythopthora cinnamomi</i> Rands |
| title_fullStr | Synthesis and In Vitro Growth Inhibition of 2-Allylphenol Derivatives Against <i>Phythopthora cinnamomi</i> Rands |
| title_full_unstemmed | Synthesis and In Vitro Growth Inhibition of 2-Allylphenol Derivatives Against <i>Phythopthora cinnamomi</i> Rands |
| title_short | Synthesis and In Vitro Growth Inhibition of 2-Allylphenol Derivatives Against <i>Phythopthora cinnamomi</i> Rands |
| title_sort | synthesis and in vitro growth inhibition of 2 allylphenol derivatives against i phythopthora cinnamomi i rands |
| topic | pest control <i>phytophthora cinnamomi</i> fungicide 2-allylphenol structure–activity relationship |
| url | https://www.mdpi.com/1420-3049/24/22/4196 |
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