title: Characterization of the ultraviolet-visible photoproducts of thiophanate-methyl using high performance liquid chromatography coupled with high resolution tandem mass spectrometry-Detection in grapes and tomatoes.
abstract: UV-visible irradiation of thiophanate-methyl (TM) led to the formation of nine photoproducts that were characterized by high performance liquid chromatography coupled with high resolution Fourier transform ion cyclotron resonance mass spectrometry (FTICR-MS). Although carbendazime has been reported in the literature to be the major metabolite and photoproduct of thiophanate-methyl, it was not detected in this study. However, an isomer of carbendazime referred as PP2, which was unambiguously characterized owing to CID experiments, was found in great abundance. Grape berries and cherry tomatoes treated with aqueous solutions of thiophanate-methyl were submitted to irradiation under laboratory conditions. TM and PP2 were detected in both peel and flesh of berries. The ability of TM and PP2 to pass through the fruit skin has been shown to be highly compound and matrix dependent. In vitro bioassays on Vibrio fischeri bacteria showed that the global ecotoxicity of the TM solution increases significantly with the irradiation time. PP2 should likely contribute to this ecotoxicity enhancement since in silico estimations for Daphnia magna provide a LC50 value seven times lower for PP2 than for the parent molecule.
authors.affiliation: LCM, CNRS, École Polytechnique, Université Paris-Saclay, 91128 Palaiseau, France.
authors.forename: Houda
authors.initials: H
authors.lastname: Chayata
authors.affiliation: LCM, CNRS, École Polytechnique, Université Paris-Saclay, 91128 Palaiseau, France.
authors.forename: Yannick
authors.initials: Y
authors.lastname: Lassalle
authors.affiliation: LCM, CNRS, École Polytechnique, Université Paris-Saclay, 91128 Palaiseau, France.
authors.forename: Édith
authors.initials: É
authors.lastname: Nicol
authors.affiliation: LCM, CNRS, École Polytechnique, Université Paris-Saclay, 91128 Palaiseau, France.
authors.forename: Sophia
authors.initials: S
authors.lastname: Manolikakes
authors.affiliation: LCM, CNRS, École Polytechnique, Université Paris-Saclay, 91128 Palaiseau, France.
authors.forename: Yasmine
authors.initials: Y
authors.lastname: Souissi
authors.affiliation: LCM, CNRS, École Polytechnique, Université Paris-Saclay, 91128 Palaiseau, France.
authors.forename: Sophie
authors.initials: S
authors.lastname: Bourcier
authors.affiliation: LCM, CNRS, École Polytechnique, Université Paris-Saclay, 91128 Palaiseau, France.
authors.forename: Corinne
authors.initials: C
authors.lastname: Gosmini
authors.affiliation: LCM, CNRS, École Polytechnique, Université Paris-Saclay, 91128 Palaiseau, France. Electronic address: stephane.bouchonnet@polytechnique.edu.
authors.forename: Stéphane
authors.initials: S
authors.lastname: Bouchonnet
mesh_terms: D048908:Aliivibrio fischeri / Q000187:drug effects; D000818:Animals; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D003198:Computer Simulation; D003621:Daphnia; D005638:Fruit / Q000737:chemistry; D008027:Light; D018551:Solanum lycopersicum / Q000737:chemistry*; D010782:Photolysis; D012996:Solutions; D053719:Tandem Mass Spectrometry / Q000379:methods; D013875:Thiophanate / Q000737:chemistry / Q000528:radiation effects* / Q000633:toxicity; D013997:Time Factors; D027843:Vitis / Q000737:chemistry*
chemical_list: D012996:Solutions; D013875:Thiophanate
keywords: Bioassays; Degradation products identification; Fruits; LC-HR-MS/MS; Photolysis; Thiophanate-methyl