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Photodegradation of carbendazim sensitized by aromatic ketones.

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Photodegradation of carbendazim sensitized by aromatic ketones.

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dc.contributor.author Jornet Olivé, Mª Dolors es_ES
dc.contributor.author Castillo López, Mª Ángeles es_ES
dc.contributor.author Sabater Marco, Consuelo es_ES
dc.contributor.author Tormos Faus, Rosa Esperanza es_ES
dc.contributor.author Miranda Alonso, Miguel Ángel es_ES
dc.date.accessioned 2017-03-27T10:49:34Z
dc.date.available 2017-03-27T10:49:34Z
dc.date.issued 2013-03-15
dc.identifier.issn 1010-6030
dc.identifier.uri http://hdl.handle.net/10251/79100
dc.description.abstract Carbendazim (1) is a benzimidazole extensively used as post-harvest fungicide on fruits and vegetables. The aim of the present work is to study the photodegradation of I sensitized by aromatic ketones, with special attention to mechanistic aspects and to the possible detoxification associated with photochemical treatment. Laser flash photolysis (LPF) lambda(exc) = 355 nm of xanthone (XA) and anthraquinone (AQ) was performed in MeCN solutions, in the presence of 1. A new transient absorbing at lambda(max) 500 and 320 nm was obtained and assigned to the semioxidized radical cation 1(+center dot). An exergonic thermodynamics for electron transfer quenching was confirmed by means of the Rehm-Weller equation. The same species was observed by direct LFP of 1 at 266 nm in polar solvents. Conversely, when a deoxygenated solution of 1 was submitted to LFP in cyclohexane the transient spectrum presented a band with maximum at 380 nm; it was assigned to the triplet excited state ((3)1*) on the basis of energy transfer to oxygen and beta-carotene. The photodegradation of 1 was achieved using XA and AQ as electron acceptors in a solar-simulator, in aerated aqueous medium; the reaction was faster with XA. Formation of a new photoproduct was initially observed; its structure was assigned as carbendazim N-C5 dimer (2). A balance of the total organic carbon (TOC) after prolonged irradiation indicated that mineralization does not occur to a significant extent, pointing to oxidative fragmentation of 1 and 2 to give a variety of low molecular weight products. To check whether the observed photodegradation of 1 results in a decreased toxicity, biological assays were performed using an established model based on the inhibition of mobility of Daphnia magna. The results demonstrate that photodegradation leads to a diminished toxicity, indicating that the photoproducts are less toxic than the parent compound. (C) 2013 Elsevier B.V. All rights reserved. es_ES
dc.description.sponsorship Financial support from the MICINN (Grant: CTQ2010-19909) and the Generalitat Valenciana (Prometeo Program) is gratefully acknowledged. en_EN
dc.language Inglés es_ES
dc.publisher Elsevier es_ES
dc.relation MICINN [CTQ2010-19909] es_ES
dc.relation.ispartof Journal of Photochemistry and Photobiology A: Chemistry es_ES
dc.rights Reconocimiento - No comercial - Sin obra derivada (by-nc-nd) es_ES
dc.subject Carbendazim es_ES
dc.subject Photocatalytic degradation es_ES
dc.subject Toxicity es_ES
dc.subject Daphnia magna es_ES
dc.subject Environmental es_ES
dc.subject.classification MICROBIOLOGIA es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.subject.classification BIOQUIMICA Y BIOLOGIA MOLECULAR es_ES
dc.title Photodegradation of carbendazim sensitized by aromatic ketones. es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1016/j.jphotochem.2013.02.004
dc.rights.accessRights Abierto es_ES
dc.contributor.affiliation Universitat Politècnica de València. Escuela Técnica Superior de Ingenieros Industriales - Escola Tècnica Superior d'Enginyers Industrials es_ES
dc.contributor.affiliation Universitat Politècnica de València. Escuela Técnica Superior de Ingeniería Agronómica y del Medio Natural - Escola Tècnica Superior d'Enginyeria Agronòmica i del Medi Natural es_ES
dc.description.bibliographicCitation Jornet Olivé, MD.; Castillo López, MÁ.; Sabater Marco, C.; Tormos Faus, RE.; Miranda Alonso, MÁ. (2013). Photodegradation of carbendazim sensitized by aromatic ketones. Journal of Photochemistry and Photobiology A: Chemistry. 256:36-41. doi:10.1016/j.jphotochem.2013.02.004 es_ES
dc.description.accrualMethod Senia es_ES
dc.relation.publisherversion http://dx.doi.org/10.1016/j.jphotochem.2013.02.004 es_ES
dc.description.upvformatpinicio 36 es_ES
dc.description.upvformatpfin 41 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 256 es_ES
dc.relation.senia 253415 es_ES


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