Synthesis of Benzoxazinones Sulphur Analogs and Their Application as Bioherbicides: 1.4-Benzothiazinones and 1.4-Benzoxathianones for Weed Control
Eight different compounds inspired by benzoxazinones were synthesized in one simple step with easy purification. These compounds have a sulfur atom instead of the oxygen atom present in benzoxazinones. Furthermore, a new derivative obtained by a Rutkauskas–Beresnevicius reaction was synthesized. The...
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MDPI AG
2023-06-01
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| Series: | Agronomy |
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| Online Access: | https://www.mdpi.com/2073-4395/13/7/1694 |
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| author | Francisco J. R. Mejías Stefan Schwaiger Rosa M. Varela José M. G. Molinillo Nuria Chinchilla Francisco A. Macías |
| author_facet | Francisco J. R. Mejías Stefan Schwaiger Rosa M. Varela José M. G. Molinillo Nuria Chinchilla Francisco A. Macías |
| author_sort | Francisco J. R. Mejías |
| collection | DOAJ |
| description | Eight different compounds inspired by benzoxazinones were synthesized in one simple step with easy purification. These compounds have a sulfur atom instead of the oxygen atom present in benzoxazinones. Furthermore, a new derivative obtained by a Rutkauskas–Beresnevicius reaction was synthesized. These compounds were evaluated in vitro to assess their phytotoxicity in plant cells by the elongation of wheat coleoptiles. The novel compounds showed higher inhibition than benzoxazinones and the positive control, especially at higher concentrations (1000 and 300 μM). Benzoxazinones have been described as histidine deacetylase inhibitors and we therefore evaluated the effect of 1.4-benzothiazinones and 1.4-benzoxathianones against HDA6, one of the most important enzymes of the family, in silico by molecular docking and molecular dynamics. In vitro studies against <i>Echinochloa crus-galli</i>, <i>Lolium rigidum</i> and <i>Portulaca oleracea</i> weeds gave interesting results against the growth of the roots for both monocots and dicots. Specifically, the inhibition was more pronounced against dicots, as in the case of common purslane, whose inhibition at a concentration of 1000 μM was similar to that of the classical herbicide employed as a positive control. Higher inhibition was obtained when an aliphatic group was present in the C2 position of 1.4-benzothiazinones. |
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| institution | Directory Open Access Journal |
| issn | 2073-4395 |
| language | English |
| last_indexed | 2024-03-11T01:23:33Z |
| publishDate | 2023-06-01 |
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| series | Agronomy |
| spelling | doaj.art-68a0f86e8038499298c3d3bc44e623d02023-11-18T17:54:46ZengMDPI AGAgronomy2073-43952023-06-01137169410.3390/agronomy13071694Synthesis of Benzoxazinones Sulphur Analogs and Their Application as Bioherbicides: 1.4-Benzothiazinones and 1.4-Benzoxathianones for Weed ControlFrancisco J. R. Mejías0Stefan Schwaiger1Rosa M. Varela2José M. G. Molinillo3Nuria Chinchilla4Francisco A. Macías5Allelopathy Group, Department of Organic Chemistry, Institute of Biomolecules (INBIO), Campus de Excelencia Internacional (ceiA3), School of Science, University of Cadiz, 11510 Puerto Real, SpainInstitute of Pharmacy, Center for Molecular Biosciences Innsbruck (CMBI), University of Innsbruck, 6020 Innsbruck, AustriaAllelopathy Group, Department of Organic Chemistry, Institute of Biomolecules (INBIO), Campus de Excelencia Internacional (ceiA3), School of Science, University of Cadiz, 11510 Puerto Real, SpainAllelopathy Group, Department of Organic Chemistry, Institute of Biomolecules (INBIO), Campus de Excelencia Internacional (ceiA3), School of Science, University of Cadiz, 11510 Puerto Real, SpainAllelopathy Group, Department of Organic Chemistry, Institute of Biomolecules (INBIO), Campus de Excelencia Internacional (ceiA3), School of Science, University of Cadiz, 11510 Puerto Real, SpainAllelopathy Group, Department of Organic Chemistry, Institute of Biomolecules (INBIO), Campus de Excelencia Internacional (ceiA3), School of Science, University of Cadiz, 11510 Puerto Real, SpainEight different compounds inspired by benzoxazinones were synthesized in one simple step with easy purification. These compounds have a sulfur atom instead of the oxygen atom present in benzoxazinones. Furthermore, a new derivative obtained by a Rutkauskas–Beresnevicius reaction was synthesized. These compounds were evaluated in vitro to assess their phytotoxicity in plant cells by the elongation of wheat coleoptiles. The novel compounds showed higher inhibition than benzoxazinones and the positive control, especially at higher concentrations (1000 and 300 μM). Benzoxazinones have been described as histidine deacetylase inhibitors and we therefore evaluated the effect of 1.4-benzothiazinones and 1.4-benzoxathianones against HDA6, one of the most important enzymes of the family, in silico by molecular docking and molecular dynamics. In vitro studies against <i>Echinochloa crus-galli</i>, <i>Lolium rigidum</i> and <i>Portulaca oleracea</i> weeds gave interesting results against the growth of the roots for both monocots and dicots. Specifically, the inhibition was more pronounced against dicots, as in the case of common purslane, whose inhibition at a concentration of 1000 μM was similar to that of the classical herbicide employed as a positive control. Higher inhibition was obtained when an aliphatic group was present in the C2 position of 1.4-benzothiazinones.https://www.mdpi.com/2073-4395/13/7/1694benzothiazinonesbioassayweedsallelopathydocking |
| spellingShingle | Francisco J. R. Mejías Stefan Schwaiger Rosa M. Varela José M. G. Molinillo Nuria Chinchilla Francisco A. Macías Synthesis of Benzoxazinones Sulphur Analogs and Their Application as Bioherbicides: 1.4-Benzothiazinones and 1.4-Benzoxathianones for Weed Control Agronomy benzothiazinones bioassay weeds allelopathy docking |
| title | Synthesis of Benzoxazinones Sulphur Analogs and Their Application as Bioherbicides: 1.4-Benzothiazinones and 1.4-Benzoxathianones for Weed Control |
| title_full | Synthesis of Benzoxazinones Sulphur Analogs and Their Application as Bioherbicides: 1.4-Benzothiazinones and 1.4-Benzoxathianones for Weed Control |
| title_fullStr | Synthesis of Benzoxazinones Sulphur Analogs and Their Application as Bioherbicides: 1.4-Benzothiazinones and 1.4-Benzoxathianones for Weed Control |
| title_full_unstemmed | Synthesis of Benzoxazinones Sulphur Analogs and Their Application as Bioherbicides: 1.4-Benzothiazinones and 1.4-Benzoxathianones for Weed Control |
| title_short | Synthesis of Benzoxazinones Sulphur Analogs and Their Application as Bioherbicides: 1.4-Benzothiazinones and 1.4-Benzoxathianones for Weed Control |
| title_sort | synthesis of benzoxazinones sulphur analogs and their application as bioherbicides 1 4 benzothiazinones and 1 4 benzoxathianones for weed control |
| topic | benzothiazinones bioassay weeds allelopathy docking |
| url | https://www.mdpi.com/2073-4395/13/7/1694 |
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