Abstract
Flubendiamide is a ryanodine insecticide that shows a strong insecticidal activity and is relatively safe for non-target organisms. Actually only flubendiamide and its product desiodo-flubendiamide have been studied during catalytic degradation using TiO2 and ZnO. Therefore, here we tested the photocatalytic removal of flubendiamide in the presence of nitrates or humic acids. Degradation kinetics were monitored using high-performance liquid chromatography ultraviolet–visible detector. Product identification was done using a high-resolution time-of-flight mass spectrometer coupled to a gas chromatograph (GC-HRMS). Results show that the addition of humic acids at 10 mg l−1 increased the removal of flubendiamide more than five times. The addition of nitrate ions at 10 mg l−1 had no influence. The removal of flubendiamide was more than ten times faster in experiments with oxygen purging. Fourteen degradation products were identified, which can be classified into three groups: phthalimide and related phthalic acid derivatives, fluorinated species related to the second amide moiety, and advanced transformation products.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Andreozzi R, Caprio V, Insola A, Marotta R (1999) Advanced oxidation processes (AOP) for water purification and recovery. Catal Today 53(1):51–59. https://doi.org/10.1016/s0920-5861(99)00102-9
Bachman J, Patterson HH (1999) Photodecomposition of the carbamate pesticide carbofuran: kinetics and the influence of dissolved organic matter. Environ Sci Technol 33(6):874–881. https://doi.org/10.1021/es9802652
Barreiro R, Pratt JR (1992) Toxic effects of chemicals on microorganisms. Water Environ Res 64(4):632–641 (ISSN 1061–4303)
Bertilsson S, Widenfalk A (2002) Photochemical degradation of PAHs in freshwaters and their impact on bacterial growth: influence of water chemistry. Hydrobiologia 469:23–32. https://doi.org/10.1023/A:1015579628189
Braham RJ, Harris AT (2009) Review of major design and scale-up considerations for solar hotocatalytic reactors. Ind Eng Chem Res 48(19):8890–8905. https://doi.org/10.1021/ie900859z
Buddidathia R, Mohapatra S, Siddamallaiah L, Manikrao G, Shankara Hebbar S (2016) Dissipation pattern of flubendiamide residues on capsicum fruit (Capsicum annuum L.) under field and controlled environmental conditions. J Environ Sci Health B 51(1):44–51. https://doi.org/10.1080/03601234.2015.1080496
Castellote M, Bengtsson N (2011) Principles of TiO2 photocatalysis. In: Ohama Y, Van Gemert D (eds) Application of titanium dioxide photocatalysis to construction materials, 1st edn. Springer, Berlin, pp 5–9
Chen J, Hub Z, Wang D, Gao C, Ji R (2010) Photocatalytic mineralization of dimethoate in aqueous solutions using TiO2: parameters and by-products analysis. Desalination 258(1–3):28–33. https://doi.org/10.1016/j.desal.2010.03.053
Daghrir R, Drogui P, Didier R (2013) Modified TiO2 for environmental photocatalytic applications: a review. Ind Eng Chem Res 52(10):3581–3599. https://doi.org/10.1021/ie303468t
Das SK, Mukherjee I (2012) Effect of moisture and organic manure on persistence of flubendiamide in soil. Bull Environ Contam Toxicol 88:515–520. https://doi.org/10.1007/s00128-012-0551-9
European Food Safety Authority (2013) Conclusion on the peer review of the pesticide risk assessment of the active substance flubendiamide. EFSA J 11(9):3298–3360. https://doi.org/10.2903/j.efsa.2013.3298
Fenoll J, Vela N, Garrido I, Navarro G, Perez-Lucas G, Navarro S (2015) Reclamation of water polluted with flubendiamide residues by photocatalytic treatment with semiconductor oxides. Photochem Photobiol 91:1088–1094. https://doi.org/10.1111/php.12479
Hustert K, Moza PN, Kettrup A (1999) Photochemical degradation of carboxin and oxycarboxin in the presence of humic substances and soil. Chemosphere 38(14):3423–3429. https://doi.org/10.1016/S0045-6535(98)00555-4
Kete M, Pavlica E, Fresno F, Bratina G, Lavrenčič Štangar U (2014) Highly active photocatalytic coatings prepared by a low-temperature method. Environ Sci Pollut Res 21:11238–11249. https://doi.org/10.1007/s11356-014-3077-3
Kushwaha N, Kaushik D (2016) Recent advances and future prospects of phthalimide derivatives. J Appl Pharm Sci 6(03):159–171. https://doi.org/10.7324/JAPS.2016.60330
Lebedev AT (2015) Mass spectrometry in organic chemistry. Technosfera, Moscow
Lebedev AT, Polyakova OV, Mazur DM, Artaev VB (2013) The benefits of high resolution mass spectrometry in environmental analysis. Analyst 138:6946–6953. https://doi.org/10.1039/C3AN01237A
Linsebigler AL, Lu G, Yates JT (1995) Photocatalysis on TiO2 surfaces: principles, mechanisms, and selected results. Chem Rev 95(3):735–758. https://doi.org/10.1021/cr00035a013
Masaki T (2008) Study on the mechanism of insecticidal activity through disruption of intracellular calcium homeostasis. J Pestic Sci 33(3):271–272. https://doi.org/10.1584/jpestics.a330301
Masaki T, Tohnishi M, Nishimatsu T, Tsubata K, Inoue K, Motoba K, Hirooka T (2005) Flubendiamide, a novel Ca2+ channel modulator, reveals evidence for functional cooperation between Ca2+ pumps and Ca2+ release. Mol Pharmacol 69(5):1733–1739. https://doi.org/10.1124/mol.105.020339
McLafferty FW, Turecek F (1993) Interpretation of mass spectra. University Science Books, Mill Valley
Méallier P (1999) Phototransformation of pesticides in aqueous solution. In: Boule P (ed) The handbook of environmental chemistry, Part L: environmental photochemistry, vol 2, 1st edn. Springer, Berlin, pp 241–261
Mohapatra S, Ahuja AK, Deepa M, Sharma D, Jagadish GK, Rashmi N (2010) Persistence and dissipation of flubendiamide and des-iodo flubendiamide in cabbage (Brassica oleracea Linne) and soil. Bull Environ Contam Toxicol 85(3):352–356. https://doi.org/10.1007/s00128-010-0063-4
Mohapatra S, Ahuja AK, Deepa M, Jagadish GK, Rashmi N, Sharma D (2011) Development of an analytical method for analysis of flubendiamide, des-iodo flubendiamide and study of their residue persistence in tomato and soil. Environ Sci Health B 46(1):264–271. https://doi.org/10.1080/03601234.2011.540536
Paramasivam M, Banerjee H (2012) Degradation dynamics of flubendiamide in different types of soils. Bull Environ Contam Toxicol 88:511–514. https://doi.org/10.1007/s00128-012-0552-8
Rabindranathan S, Devipriya S, Yesodharan S (2003) Photocatalytic degradation of phosphamidon on semiconductor oxides. J Hazard Mater 102(2):217–229. https://doi.org/10.1016/S0304-3894(03)00167-5
Remucal CK (2014) The role of indirect photochemical degradation in the environmental fate of pesticides: a review. Environ Sci Process Impacts 16:628–653. https://doi.org/10.1039/c3em00549f
Richard C, Canonica S (2005) Aquatic phototransformation of organic contaminants induced by coloured dissolved organic matter. In: Boule P, Bahnemann DW, Robertson PKJ (eds) Environmental photochemistry part II, the handbook of environmental chemistry, 2nd edn. Springer, Berlin, pp 299–323
Tohnishi M, Nakao H, Furuya T, Seo A, Odama H, Tsubata K, Fujioka S, Kodama S, Hirooka T, Nishimatsu T (2005) Flubendiamide, a novel insecticide highly active against Lepidopterous insect. Pests J Pestic Sci 30(4):354–360. https://doi.org/10.1584/jpestics.30.354
Acknowledgements
The authors acknowledge the financial support from the Slovenian Research Agency [research core funding No. P3-0388, Mechanisms of health protection (Mehanizmi varovanja zdravja)]. We acknowledge financial support from Scholarship of the Republic of Slovenia scheme Mobility Grant (CMEPIUS).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Bavcon Kralj, M., Divanović, H., Košenina, S. et al. Effect of humic acids, nitrate and oxygen on the photodegradation of the flubendiamide insecticide: identification of products. Environ Chem Lett 16, 591–597 (2018). https://doi.org/10.1007/s10311-017-0691-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10311-017-0691-6