Synthesis and evaluation as biodegradable herbicides of halogenated analogs of L-meta-tyrosine
Uloženo v:
| Název: | Synthesis and evaluation as biodegradable herbicides of halogenated analogs of L-meta-tyrosine |
|---|---|
| Autoři: | Movellan, Julie, Rocher, Françoise, Chikh, Zohra, Marivingt-Mounir, Cécile, Bonnemain, Jean-Louis, Chollet, Jean-François |
| Přispěvatelé: | Institut de chimie des milieux et matériaux de Poitiers UMR 7285 (IC2MP Poitiers ), Université de Poitiers = University of Poitiers (UP)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS), Sucres & Échanges Végétaux-Environnement Équipe du laboratoire EBI Poitiers (SEVE), Écologie et biologie des interactions UMR 7267 (EBI Poitiers ), Université de Poitiers = University of Poitiers (UP)-Centre National de la Recherche Scientifique (CNRS)-Université de Poitiers = University of Poitiers (UP)-Centre National de la Recherche Scientifique (CNRS) |
| Zdroj: | ISSN: 0944-1344. |
| Informace o vydavateli: | CCSD Springer Verlag |
| Rok vydání: | 2014 |
| Sbírka: | Université de Poitiers: Publications de nos chercheurs.ses (HAL) |
| Témata: | Halogenated analogs of L-meta-tyrosine, m-Tyrosine, Allelopathy, Allelochemicals, Herbicide, Sustainable agriculture, MESH: Biodegradation, Environmental, MESH: Festuca / metabolism, MESH: Plant Roots / growth & development, MESH: Soil, MESH: Soil Microbiology, MESH: Tyrosine / analogs & derivatives, MESH: Tyrosine / analysis, MESH: Tyrosine / metabolism, MESH: Half-Life, MESH: Halogenation, MESH: Herbicides / chemical synthesis, MESH: Herbicides / chemistry, MESH: Herbicides / toxicity, MESH: Lactuca / growth & development, MESH: Lactuca / metabolism, MESH: Plant Roots / drug effects, [CHIM.ORGA]Chemical Sciences/Organic chemistry, [SDV.BV.PEP]Life Sciences [q-bio]/Vegetal Biology/Phytopathology and phytopharmacy |
| Popis: | International audience ; l-meta-tyrosine is an herbicidal nonprotein amino acid isolated some years ago from fine fescue grasses and characterized by its almost immediate microbial degradation in soil (half-life < 24 h). Nine monohalogenated or dihalogenated analogs of this allelochemical have been obtained through a seven-step stereoselective synthesis from commercial halogenated phenols. Bioassays showed a large range of biological responses, from a growth root inhibition of lettuce seedling similar to that noted with m-tyrosine [2-amino-3-(2-chloro-5-hydroxyphenyl)propanoic acid or compound 8b] to an increase of the primary root growth concomitant with a delay of secondary root initiation [2-amino-3-[2-fluoro-5-hydroxy-3-(trifluoromethyl)phenyl]propanoic acid or compound 8h]. Compound 8b was slightly less degraded than m-tyrosine in the nonsterilized nutritive solution used for lettuce development, while the concentration of compound 8h remained unchanged for at least 2 weeks. These data indicate that it is possible to manipulate both biological properties and degradation of m-tyrosine by halogen addition. |
| Druh dokumentu: | article in journal/newspaper |
| Jazyk: | English |
| Relation: | info:eu-repo/semantics/altIdentifier/pmid/23224500; PUBMED: 23224500 |
| DOI: | 10.1007/s11356-012-1302-5 |
| Dostupnost: | https://hal.science/hal-02895216 https://hal.science/hal-02895216v1/document https://hal.science/hal-02895216v1/file/Manuscrit%20HAL.pdf https://doi.org/10.1007/s11356-012-1302-5 |
| Rights: | info:eu-repo/semantics/OpenAccess |
| Přístupové číslo: | edsbas.B19A2D48 |
| Databáze: | BASE |
Nájsť tento článok vo Web of Science | Abstrakt: | International audience ; l-meta-tyrosine is an herbicidal nonprotein amino acid isolated some years ago from fine fescue grasses and characterized by its almost immediate microbial degradation in soil (half-life < 24 h). Nine monohalogenated or dihalogenated analogs of this allelochemical have been obtained through a seven-step stereoselective synthesis from commercial halogenated phenols. Bioassays showed a large range of biological responses, from a growth root inhibition of lettuce seedling similar to that noted with m-tyrosine [2-amino-3-(2-chloro-5-hydroxyphenyl)propanoic acid or compound 8b] to an increase of the primary root growth concomitant with a delay of secondary root initiation [2-amino-3-[2-fluoro-5-hydroxy-3-(trifluoromethyl)phenyl]propanoic acid or compound 8h]. Compound 8b was slightly less degraded than m-tyrosine in the nonsterilized nutritive solution used for lettuce development, while the concentration of compound 8h remained unchanged for at least 2 weeks. These data indicate that it is possible to manipulate both biological properties and degradation of m-tyrosine by halogen addition. |
|---|---|
| DOI: | 10.1007/s11356-012-1302-5 |