Abstract
This work enabled the identification of major transformation products (TPs) of thiabendazole (TBZ) during the Fenton process. TBZ is a benzimidazole fungicide widely used around the world to prevent and/or treat a wide range of fruit and vegetable pathogens. The degradation of the parent molecule and the identification of the main TPs were carried out in demineralized water. The TPs were monitored and identified by liquid chromatography-quadrupole time-of-flight mass spectrometry (LC-QTOF-MS/MS). Up to 12 TPs were tentatively identified. Most of them were eliminated after 15 min of treatment time and originated from numerous hydroxylations undergone by the aromatic ring during the initial stages of the process.
Similar content being viewed by others
References
Köck-Schulmeyer M, Villagrasa M, de Alda ML, Céspedes-Sánchez R, Ventura F, Barceló D (2013) Occurrence and behavior of pesticides in wastewater treatment plants and their environmental impact. Sci Total Environ 458–460:466–476
Peréz JAS, Carra I, Sirtori C, Agüera A, Esteban B (2014) Fate of thiabendazole through the treatment of a simulated agro-food industrial effluent by combined MBR/Fenton processes at μg/L scale. Water Res 51:55–63
Veneziano A, Vacca G, Arana S, de Simone F, Rastrelli L (2004) Determination of carbendazim, thiabendazole and thiophanate-methyl in banana (Musa acuminata) samples imported to Italy. Food Chem 87:383–386
Castillo LE, Ruepert C, Solis E (2000) Pesticide residues in the aquatic environment of banana plantation: areas in the north Atlantic zone of Costa Rica. Environ Toxicol Chem 19:1942–1950
Müller C, David L, Chiş V, Pînzaru SC (2014) Detection of thiabendazole applied on citrus fruits and bananas using surface enhanced Raman scattering. Food Chem 145:814–820
Ito Y, Ikai Y, Oka H, Hayakawa J, Kagami T (1998) Application of ion-exchange cartridge clean-up in food analysis: I. Simultaneous determination of thiabendazole and imazalil in citrus fruit and banana using high-performance liquid chromatography with ultraviolet detection. J Chromatogr A 810:81–87
Cuadros S, Manresa MÀ, Font J, Bautista ME, Puig R, Marsal A (2012) Alternative fungicides for the leather industry: application in various processes. J Soc Leath Tech Ch 96:225–233
Karas PA, Perruchon C, Exarhou K, Ehaliotis C, Karpouzas DG (2011) Potential for bioremediation of agro-industrial effluents with high loads of pesticides by selected fungi. Biodegradation 22:215–228
Bernabeu A, Vercher RF, Santos-Juanes L, Simón PJ, Lardín C, Martínez MA, Vicente JA, González R, Llosá C, Arques A, Amat AM (2011) Solar photocatalysis as a tertiary treatment to remove emerging pollutants from wastewater treatment plant effluents. Catal Today 161:235–240
Sievers M (2011) Advanced oxidation processes. Treatise on Water Science 4:377–408
Klamerth N, Malato S, Agüera A, Fernández-Alba A (2013) Photo-Fenton and modified photo-Fenton at neutral pH for the treatment of emerging contaminants in wastewater treatment plant effluents: a comparison. Water Res 47:833–840
Klamerth N, Rizzo L, Malato S, Maldonado MI, Agüera A, Fernández-Alba AR (2010) Degradation of fifteen emerging contaminants at μgL−1 initial concentrations by mild solar photo-Fenton in MWTP effluents. Water Res 44:545–554
Klamerth N, Malato S, Maldonado MI, Agüera A, Fernández-Alba A (2011) Modified photo-Fenton for degradation of emerging contaminants in municipal wastewater effluents. Catal Today 161:241–246
Trovó AG, Nogueira RFP, Agüera A, Fernandez-Alba AR, Sirtori C, Malato S (2009) Degradation of sulfamethoxazole in water by solar photo-Fenton. Chemical and toxicological evaluation. Water Res 43:3922–3931
Fatta-Kassinos D, Kalavrouziotis IK, Koukoulakis PH, Vasquez MI (2011) The risks associated with wastewater reuse and xenobiotics in the agroecological environment. Sci Total Environ 409:3555–3563
Sirtori C, Agüera A, Gernjak W, Malato S (2010) Effect of water-matrix composition on Trimethoprim solar photodegradation kinetics and pathways. Water Res 44:2735–2744
Agüera A, Bueno MJM, Fernández-Alba AR (2013) New trends in the analytical determination of emerging contaminants and their transformation products in environmental waters. Environ Sci Pollut R 20:3496–3515
Lam MW, Mabury SA (2005) Photodegradation of the pharmaceuticals atorvastatin, carbamazepine, levofloxacin, and sulfamethoxazole in natural waters. Aquat Sci 67:177–188
Malato S, Albanis T, Piedra L, Agüera A, Hernando D, Fernández-Alba A (2003) In: Ferrer I, Thurman EM (eds) Liquid chromatography/ mass spectrometry, MS/MS and time-of-flight MS analysis of emerging contaminants. American Chemical Society, Washington
Agüera A, Gómez-Ramos MM, Fernandez-Alba AR (2012) In: Fernandez-Alba AR (ed) TOF-MS within food and environmental analysis. Elsevier, Amsterdam
Watkins DAM (1976) Photolysis of thiabendazole. Chemosphere 5:77–78
Moza PN, Murthy NBK, Hustert K, Raghu K, Kettrup A (1996) Photolysis of thiabendazole in aqueous solution and in the presence of fulvic and humic acids. Chemosphere 33:1915–1920
Calza P, Baudino S, Aigotti R, Baiocchi C, Pelizzetti E (2003) Ion trap tandem mass spectrometric identification of thiabendazole phototransformation products on titanium dioxide. J Chromatogr A 984:59–66
Nogueira RFP, Oliveira MC, Paterlini WC (2005) Simple and fast spectrophotometric determination of H2O2 in photo-Fenton reactions using metavanadate. Talanta 66:86–91
Ikehata K, El-Din MG (2006) Aqueous pesticide degradation by hydrogen peroxide/ultraviolet irradiation and Fenton-type advanced oxidation processes: a review. J Environ Eng Sci 5:81–135
Pignatello JJ, Oliveros E, MacKay A (2006) Advanced oxidation processes for organic contaminant destruction based on the Fenton reaction and related chemistry. Crit Rev Env Sci Technol 36:1–84
Ji Y, Zhou L, Ferronato C, Salvador A, Yang X (2013) Degradation of sunscreen agent 2-phenylbenzimidazole-5-sulfonic acid by TiO2 photocatalysis: kinetics, photoproducts and comparison to structurally related compounds. Appl Catal B 140–141:457–467
Fujitani T, Yoneyama M, Ogata A, Ueta T, Mori K, Ichikawa H (1991) New metabolites of thiabendazole and the metabolism of thiabendazole by mouse embryo in vivo and in vitro. Food Chem Toxicol 29:265–274
Acknowledgments
This research was supported by the Ministry of Economy and Competitiveness (FOTOREG, CTQ 2010-20740-C03-01/PPQ and CTQ 2010-20740-C03-03/PPQ) and the European Regional Development Fund (ERDF). Irene Carra would like to acknowledge the Ministry of Education, Culture and Sport for her FPU scholarship (AP2010-3218).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Sirtori, C., Agüera, A., Carra, I. et al. Identification and monitoring of thiabendazole transformation products in water during Fenton degradation by LC-QTOF-MS. Anal Bioanal Chem 406, 5323–5337 (2014). https://doi.org/10.1007/s00216-014-7942-1
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00216-014-7942-1