title: Biotransformation of Dimethenamid-P by the basidiomycete Irpex consors.
abstract: Twenty-nine basidiomycetes were screened in surface and liquid cultures for their capability to biotransform the chloroacetamide herbicide Dimethenamid-P (DMTA-P). The basidiomycete Irpex consors converted 70% of the herbicide (0.5 g L-1DMTA-P) in liquid cultures within 6 days, applying a minimal medium under non-ligninolytic conditions. Nine transformation products of DMTA-P were identified by liquid chromatography-mass spectrometry analysis of the culture supernatants. The four main metabolites were isolated and subjected to GC-MS analysis and NMR spectroscopy. The analyses revealed that the thiophene ring was oxidized at three different positions. Metabolite M1 was identified as the S-oxide, which was isolable and relatively stable at room temperature. In metabolite M2, one methyl substituent of the thiophene ring was hydroxylated. The two metabolites M3A and M3B were diastereomers, but fully separated by HPLC. Here, oxidation of the aromatic CH carbon resulted in prototropic rearrangement to an αβ-unsaturated thiolactone. None of the three major metabolites of DMTA-P has been described before.
authors.affiliation: Institute of Food Chemistry and Food Biotechnology, Justus Liebig University Giessen, Heinrich-Buff Ring 17, 35392 Giessen, Germany.
authors.forename: Adrian
authors.initials: A
authors.lastname: Imami
authors.affiliation: Institute of Food Chemistry and Food Biotechnology, Justus Liebig University Giessen, Heinrich-Buff Ring 17, 35392 Giessen, Germany.
authors.forename: Nicolai
authors.initials: N
authors.lastname: Herold
authors.affiliation: Institute of Food Chemistry and Food Biotechnology, Justus Liebig University Giessen, Heinrich-Buff Ring 17, 35392 Giessen, Germany.
authors.forename: Astrid
authors.initials: A
authors.lastname: Spielmeyer
authors.affiliation: Institute of Organic Chemistry, Justus Liebig University Giessen, Heinrich-Buff Ring 17, 35392 Giessen, Germany.
authors.forename: Heike
authors.initials: H
authors.lastname: Hausmann
authors.affiliation: BASF SE, 67056 Ludwigshafen, Germany.
authors.forename: Reinhard
authors.initials: R
authors.lastname: Dötzer
authors.affiliation: BASF SE, 67056 Ludwigshafen, Germany.
authors.forename: Henning N
authors.initials: HN
authors.lastname: Behnken
authors.affiliation: BASF SE, 67056 Ludwigshafen, Germany.
authors.forename: Sabine
authors.initials: S
authors.lastname: Leonhardt
authors.affiliation: BASF SE, 67056 Ludwigshafen, Germany.
authors.forename: Andrea
authors.initials: A
authors.lastname: Weil
authors.affiliation: BASF SE, 67056 Ludwigshafen, Germany.
authors.forename: Sebastian
authors.initials: S
authors.lastname: Schoof
authors.affiliation: Institute of Food Chemistry and Food Biotechnology, Justus Liebig University Giessen, Heinrich-Buff Ring 17, 35392 Giessen, Germany. Electronic address: holger.zorn@uni-giessen.de.
authors.forename: Holger
authors.initials: H
authors.lastname: Zorn
mesh_terms: D000083:Acetanilides / Q000378:metabolism*; D001487:Basidiomycota / Q000254:growth & development / Q000378:metabolism*; D001711:Biotransformation; D002250:Carbon Radioisotopes / Q000032:analysis*; D002851:Chromatography, High Pressure Liquid; D008401:Gas Chromatography-Mass Spectrometry; D013058:Mass Spectrometry; D010084:Oxidation-Reduction; D013876:Thiophenes / Q000032:analysis
chemical_list: D000083:Acetanilides; D002250:Carbon Radioisotopes; D013876:Thiophenes; C120861:dimethenamid
keywords: Basidiomycete; Biotransformation; Dimethenamid-P; Irpex consors; Metabolite analysis; Thiophene S-oxide