Photodegradation of the Novel Fungicide Fluopyram in Aqueous Solution: Kinetics, Transformation Products, and Toxicity Evolvement

Overview

Journal Environ Sci Pollut Res Int

Publisher Springer

Specialties Environmental Health
Toxicology

Date 2016 Jun 26

PMID 27343079

Citations 6

Authors

Bizhang Dong

Jiye Hu

Affiliations

Soon will be listed here.

Abstract

The aqueous photodegradation of fluopyram was investigated under UV light (λ ≥ 200 nm) and simulated sunlight irradiation (λ ≥ 290 nm). The effect of solution pH, fulvic acids (FA), nitrate (NO3 (-)), Fe (III) ions, and titanium dioxide (TiO2) on direct photolysis of fluopyram was explored. The results showed that fluopyram photodegradation was faster in neutral solution than that in acidic and alkaline solutions. The presence of FA, NO3 (-), Fe (III), and TiO2 slightly affected the photodegradation of fluopyram under UV irradiation, whereas the photodegradation rates of fluopyram with 5 mg L(-1) Fe (III) and 500 mg L(-1) TiO2 were about 7-fold and 13-fold faster than that without Fe (III) and TiO2 under simulated sunlight irradiation, respectively. Three typical products for direct photolysis of fluopyram have been isolated and characterized by liquid chromatography tandem mass spectrometry. These products resulted from the intramolecular elimination of HCl, hydroxyl-substitution, and hydrogen extraction. Based on the identified transformation products and evolution profile, a plausible degradation pathway for the direct photolysis of fluopyram in aqueous solution was proposed. In addition, acute toxicity assays using the Vibrio fischeri bacteria test indicated that the transformation products were more toxic than the parent compound.

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References

Doll T, Frimmel F . Photocatalytic degradation of carbamazepine, clofibric acid and iomeprol with P25 and Hombikat UV100 in the presence of natural organic matter (NOM) and other organic water constituents. Water Res. 2005; 39(2-3):403-11. DOI: 10.1016/j.watres.2004.09.016. View

Ishii H, Miyamoto T, Ushio S, Kakishima M . Lack of cross-resistance to a novel succinate dehydrogenase inhibitor, fluopyram, in highly boscalid-resistant isolates of Corynespora cassiicola and Podosphaera xanthii. Pest Manag Sci. 2011; 67(4):474-82. DOI: 10.1002/ps.2092. View

Pinna M, Pusino A . Direct and indirect photolysis of two quinolinecarboxylic herbicides in aqueous systems. Chemosphere. 2011; 86(6):655-8. DOI: 10.1016/j.chemosphere.2011.11.016. View

Wei L, Shifu C, Wei Z, Sujuan Z . Titanium dioxide mediated photocatalytic degradation of methamidophos in aqueous phase. J Hazard Mater. 2008; 164(1):154-60. DOI: 10.1016/j.jhazmat.2008.07.140. View

De Miccolis Angelini R, Masiello M, Rotolo C, Pollastro S, Faretra F . Molecular characterisation and detection of resistance to succinate dehydrogenase inhibitor fungicides in Botryotinia fuckeliana (Botrytis cinerea). Pest Manag Sci. 2014; 70(12):1884-93. DOI: 10.1002/ps.3748. View

Martinez Vidal J, Plaza-Bolanos P, Romero-Gonzalez R, Frenich A . Determination of pesticide transformation products: a review of extraction and detection methods. J Chromatogr A. 2009; 1216(40):6767-88. DOI: 10.1016/j.chroma.2009.08.013. View

Kim T, Kim J, Choi K, Stenstrom M, Zoh K . Degradation mechanism and the toxicity assessment in TiO2 photocatalysis and photolysis of parathion. Chemosphere. 2005; 62(6):926-33. DOI: 10.1016/j.chemosphere.2005.05.038. View

Tercero Espinoza L, Neamtu M, Frimmel F . The effect of nitrate, Fe(III) and bicarbonate on the degradation of bisphenol A by simulated solar UV-irradiation. Water Res. 2007; 41(19):4479-87. DOI: 10.1016/j.watres.2007.06.060. View

Sinclair C, Boxall A . Assessing the ecotoxicity of pesticide transformation products. Environ Sci Technol. 2003; 37(20):4617-25. DOI: 10.1021/es030038m. View

10.

Hoff R, Meneghini L, Pizzolato T, do Carmo Ruaro Peralba M, Diaz-Cruz M, Barcelo D . Structural elucidation of sulfaquinoxaline metabolism products and their occurrence in biological samples using high-resolution Orbitrap mass spectrometry. Anal Chem. 2014; 86(11):5579-86. DOI: 10.1021/ac501132r. View

11.

Chen Y, Zhang K, Zuo Y . Direct and indirect photodegradation of estriol in the presence of humic acid, nitrate and iron complexes in water solutions. Sci Total Environ. 2013; 463-464:802-9. DOI: 10.1016/j.scitotenv.2013.06.026. View

12.

Abramovic B, Banic N, Sojic D . Degradation of thiacloprid in aqueous solution by UV and UV/H2O2 treatments. Chemosphere. 2010; 81(1):114-9. DOI: 10.1016/j.chemosphere.2010.07.016. View

13.

Tong L, Eichhorn P, Perez S, Wang Y, Barcelo D . Photodegradation of azithromycin in various aqueous systems under simulated and natural solar radiation: kinetics and identification of photoproducts. Chemosphere. 2011; 83(3):340-8. DOI: 10.1016/j.chemosphere.2010.12.025. View

14.

Lavtizar V, van Gestel C, Dolenc D, Trebse P . Chemical and photochemical degradation of chlorantraniliprole and characterization of its transformation products. Chemosphere. 2013; 95:408-14. DOI: 10.1016/j.chemosphere.2013.09.057. View

15.

Feng W, Nansheng D . Photochemistry of hydrolytic iron (III) species and photoinduced degradation of organic compounds. A minireview. Chemosphere. 2000; 41(8):1137-47. DOI: 10.1016/s0045-6535(00)00024-2. View

16.

Veloukas T, Karaoglanidis G . Biological activity of the succinate dehydrogenase inhibitor fluopyram against Botrytis cinerea and fungal baseline sensitivity. Pest Manag Sci. 2012; 68(6):858-64. DOI: 10.1002/ps.3241. View

17.

Escher B, Fenner K . Recent advances in environmental risk assessment of transformation products. Environ Sci Technol. 2011; 45(9):3835-47. DOI: 10.1021/es1030799. View

18.

Grabowska E, Reszczynska J, Zaleska A . Mechanism of phenol photodegradation in the presence of pure and modified-TiO2: A review. Water Res. 2012; 46(17):5453-5471. DOI: 10.1016/j.watres.2012.07.048. View

19.

Avetta P, Marchetti G, Minella M, Pazzi M, De Laurentiis E, Maurino V . Phototransformation pathways of the fungicide dimethomorph ((E,Z) 4-[3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]morpholine), relevant to sunlit surface waters. Sci Total Environ. 2014; 500-501:351-60. DOI: 10.1016/j.scitotenv.2014.08.067. View

20.

Xu J, Hao Z, Guo C, Zhang Y, He Y, Meng W . Photodegradation of sulfapyridine under simulated sunlight irradiation: kinetics, mechanism and toxicity evolvement. Chemosphere. 2013; 99:186-91. DOI: 10.1016/j.chemosphere.2013.10.069. View