Synthesis of Epoxyoxirenes: Phytotoxic Activity and Enzymatic Target Identification
Chemical control is key to minimizing agricultural losses, driving the search for more efficient and selective herbicides. This study reports the synthesis of epoxyoxirenes, their phytotoxic evaluation, and an <i>in silico</i> analysis to identify the protein target of the most active co...
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MDPI AG
2025-06-01
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| author | Kamylla C. F. de Faria Elson S. Alvarenga Denilson F. Oliveira Vitor C. Baia Armin F. Isenmann |
| author_facet | Kamylla C. F. de Faria Elson S. Alvarenga Denilson F. Oliveira Vitor C. Baia Armin F. Isenmann |
| author_sort | Kamylla C. F. de Faria |
| collection | DOAJ |
| description | Chemical control is key to minimizing agricultural losses, driving the search for more efficient and selective herbicides. This study reports the synthesis of epoxyoxirenes, their phytotoxic evaluation, and an <i>in silico</i> analysis to identify the protein target of the most active compound in plants. Compounds 2–19 were tested on <i>Lactuca sativa</i> spp., <i>Allium cepa</i> spp., <i>Cucumis sativus</i> spp., <i>Triticum aestivum</i>, and <i>Bidens pilosa</i>. The synthetic route began with anhydride <b>1</b>, obtained via a Diels–Alder reaction between maleic anhydride and furan (91% yield). Anhydride <b>1</b> was converted into amides <b>2</b>–<b>7</b> through reactions with aromatic amines (>92% yields), followed by cyclization to imides <b>8</b>–<b>13</b> (60–83% yields), and subsequent epoxidation to afford epoxides <b>14</b>–<b>19</b> (62–98% yields). All the compounds interfered with seedling development, with compounds <b>2</b>–<b>7</b> showing the greatest phytotoxicity to <i>B. pilosa</i> at concentrations of 500 μM and 1000 μM. An <i>in silico</i> analysis suggested plant tubulin as a potential protein target for the most active compounds. These findings highlight epoxyoxirenes as promising scaffolds for novel herbicide development and support further investigation into their mechanism of action. |
| format | Article |
| id | doaj-art-af309a52fb334c9fb719112d005ef7cb |
| institution | DOAJ |
| issn | 2223-7747 |
| language | English |
| publishDate | 2025-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Plants |
| spelling | doaj-art-af309a52fb334c9fb719112d005ef7cb2025-08-20T03:16:56ZengMDPI AGPlants2223-77472025-06-011413193310.3390/plants14131933Synthesis of Epoxyoxirenes: Phytotoxic Activity and Enzymatic Target IdentificationKamylla C. F. de Faria0Elson S. Alvarenga1Denilson F. Oliveira2Vitor C. Baia3Armin F. Isenmann4Department of Chemistry, Universidade Federal de Viçosa, Viçosa 36570-900, MG, BrazilDepartment of Chemistry, Universidade Federal de Viçosa, Viçosa 36570-900, MG, BrazilDepartment of Chemistry, Universidade Federal de Lavras, Lavras 37203-202, MG, BrazilDepartment of Chemistry, Universidade Federal de Viçosa, Viçosa 36570-900, MG, BrazilDepartment of Metallurgy and Chemistry, Centro Federal de Educação Tecnológica de Minas Gerais, Timoteo 35180-008, MG, BrazilChemical control is key to minimizing agricultural losses, driving the search for more efficient and selective herbicides. This study reports the synthesis of epoxyoxirenes, their phytotoxic evaluation, and an <i>in silico</i> analysis to identify the protein target of the most active compound in plants. Compounds 2–19 were tested on <i>Lactuca sativa</i> spp., <i>Allium cepa</i> spp., <i>Cucumis sativus</i> spp., <i>Triticum aestivum</i>, and <i>Bidens pilosa</i>. The synthetic route began with anhydride <b>1</b>, obtained via a Diels–Alder reaction between maleic anhydride and furan (91% yield). Anhydride <b>1</b> was converted into amides <b>2</b>–<b>7</b> through reactions with aromatic amines (>92% yields), followed by cyclization to imides <b>8</b>–<b>13</b> (60–83% yields), and subsequent epoxidation to afford epoxides <b>14</b>–<b>19</b> (62–98% yields). All the compounds interfered with seedling development, with compounds <b>2</b>–<b>7</b> showing the greatest phytotoxicity to <i>B. pilosa</i> at concentrations of 500 μM and 1000 μM. An <i>in silico</i> analysis suggested plant tubulin as a potential protein target for the most active compounds. These findings highlight epoxyoxirenes as promising scaffolds for novel herbicide development and support further investigation into their mechanism of action.https://www.mdpi.com/2223-7747/14/13/1933epoxyoxirenesherbicidesphytotoxicityDiels–Alder reaction<i>in silico</i>protein target |
| spellingShingle | Kamylla C. F. de Faria Elson S. Alvarenga Denilson F. Oliveira Vitor C. Baia Armin F. Isenmann Synthesis of Epoxyoxirenes: Phytotoxic Activity and Enzymatic Target Identification Plants epoxyoxirenes herbicides phytotoxicity Diels–Alder reaction <i>in silico</i> protein target |
| title | Synthesis of Epoxyoxirenes: Phytotoxic Activity and Enzymatic Target Identification |
| title_full | Synthesis of Epoxyoxirenes: Phytotoxic Activity and Enzymatic Target Identification |
| title_fullStr | Synthesis of Epoxyoxirenes: Phytotoxic Activity and Enzymatic Target Identification |
| title_full_unstemmed | Synthesis of Epoxyoxirenes: Phytotoxic Activity and Enzymatic Target Identification |
| title_short | Synthesis of Epoxyoxirenes: Phytotoxic Activity and Enzymatic Target Identification |
| title_sort | synthesis of epoxyoxirenes phytotoxic activity and enzymatic target identification |
| topic | epoxyoxirenes herbicides phytotoxicity Diels–Alder reaction <i>in silico</i> protein target |
| url | https://www.mdpi.com/2223-7747/14/13/1933 |
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