Abstract
Combination of organoclay sorption with manganese(IV) oxide (MnO2) catalyzed catechol oxidation was studied for the removal of a dicarboximide fungicide, iprodione, from water. Iprodion in water was sorbed on didodecyldimethylammonium bromide (DDAB)-modified montmorillonite (MT) organoclay and converted into the degraded product, 3,5-dichloroaniline (DCA). The degree of sorption increased by the modification with DDAB, because of the formation of a hydrophobic region for the incorporation of iprodione and negligibly interfered by coexisting MnO2. The half-life for the degradation of irodione in water at 25 °C was 7 days, whreas it reduced to 15 min in the organoclay. The activation energy, 65.4 ± 4.8 kJ mol−1, for the first-order reaction in the aqueous solution (pH 7.0) decreased to 43.9 ± 1.8 kJ mol−1 in the organoclay, indicating the catalytic activity of the organoclay that accelerates the hydrolysis reaction of iprodione. In the coexistence of appropriate amounts of MnO2 and catechol, the degraded product, DCA, reacted with oxidized products of catechol to form a water-insoluble precipitate and was successfully eliminated from water. The results obtained in the present study strongly suggest the applicability of the combined method of organoclay sorption method and MnO2-catalyzed oxidation for the diffusion control of toxic agrochemicals.
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The data obtained in this study can serve as basic data when laying soil to prevent the spread of sprayed pesticides.
References
A. Ahmed, A. Shamsi, B. Bano, Deciphering the toxic effects of iprodione, a fungicide and malathion, an insecticide on thiol protease inhibitor isolated from yellow Indian mustard seeds. Environ. Toxicol. Pharmacol. 61, 52–60 (2018). https://doi.org/10.1016/j.etap.2018.05.019
M. Cong, S. He, J. Zhang, C. Luo, F. Zhu, Hormetic effects of mixtures of carbendazim and iprodione on the virulence of botrytis cinerea. Plant Dis. 103, 95–101 (2019). https://doi.org/10.1094/PDIS-05-18-0754-RE
Y. Wei, Y. Meng, Y. Huang, Z. Liu, K. Zhong, J. Ma, W. Zhang, Y. Li, H. Lu, Development toxicity and cardiotoxicity in zebrafish from exposure to iprodione. Chemosphere 263, 127860 (2021). https://doi.org/10.1016/j.chemosphere.2020.127860
L.E. Gray Jr., J. Ostby, J. Furr, C.J. Wolf, C. Lambright, L. Parks, D.N. Veeramachaneni, V. Wilson, M. Price, A. Hotchkiss, E. Orlando, L. Guillette, Effects of environmental antiandrogens on reproductive development in experimental animals. Hum. Reprod. Update 7, 248–264 (2001). https://doi.org/10.1093/humupd/7.3.248
P. Durand, G. Martin, A. Blondet, J. Gilleron, D. Carette, S. Janczarski, E. Christin, G. Pointis, M.H. Perrard, Effects of low doses of carbendazim or iprodione either separately or in mixture on the pubertal rat seminiferous epithelium: An ex vivo study. Toxicol. in Vitro 45, 366–373 (2017). https://doi.org/10.1016/j.tiv.2017.05.022
M. Leistra, A.M. Matser, Adsorption, transformation, and bioavailability of the fungicides carbendazim and iprodione in soil, alone and in combination. J. Environ. Sci. Health B. 39, 1–17 (2004). https://doi.org/10.1081/PFC-120027435
J. Strömqvist, N. Jarvis, Sorption, degradation and leaching of the fungicide iprodione in a golf green under Scandinavian conditions: measurements, modelling and risk assessment. Pest Manag. Sci. 61, 1168–1178 (2005). https://doi.org/10.1002/ps.1101
M. Oiwa, K. Yamaguchi, H. Hayashi, T. Saitoh, Rapid sorption of fenitrothion on didodecyldimethylammonium bromide-montmorillonite organoclay followed by the degradation into less toxic 3-methyl-4-nitrophenolate. J. Environ. Chem. Eng. 8, 104000 (2020). https://doi.org/10.1016/j.jece.2020.104000
T. Saitoh, T. Shibayama, Removal and degradation of β-lactam antibiotics in water using didodecyldimethylammonium bromide-modified montmorillonite organoclay. J. Hazard. Mater. 317, 677–685 (2016). https://doi.org/10.1016/j.jhazmat.2016.06.003
S. Vasileiadis, E. Puglisi, E.S. Papadopoulou, G. Pertile, N. Suciu, R.A. Pappolla, M. Tourna, P.A. Karas, F. Papadimitriou, A. Kasiotakis, N. Ipsilanti, A. Ferrarini, S. Sułowicz, F. Fornasier, U. Menkissoglu-Spiroudi, G.W. Nicol, M. Trevisan, D.G. Karpouzas, Blame it on the metabolite: 3,5-Dichloroaniline rather than the parent compound is responsible for the decreasing diversity and function of soil microorganisms. Appl. Environ. Microbiol. 84, e01536-e1618 (2018). https://doi.org/10.1128/AEM.01536-18
Q. Lai, X. Sun, L. Li, D. Li, M. Wang, H. Shi, Toxicity effects of procymidone, iprodione and their metabolite of 3,5-dichloroaniline to zebrafish. Chemosphere 272, 129577 (2021). https://doi.org/10.1016/j.chemosphere.2021.129577
A. Sarker, S.-H. Lee, S.-Y. Kwak, R. Nandi, J.-E. Kim, Comparative catalytic degradation of a metabolite 3,5-dichloroaniline derived from dicarboximide fungicide by laccase and MnO2 mediators. Ecotoxicol. Environ. Saf. 196, 110561 (2020). https://doi.org/10.1016/j.ecoenv.2020.110561
M.M.B. Simón, A.D.E. Cózar, L.M.P. Díez, Spectrophotometric determination of cationic surfactants in frozen and fresh squid by ion-pair formation with Methyl Orange. Analyst 115, 337–339 (1990). https://doi.org/10.1039/AN9901500337
R.M.M. Brito, W.L.C. Vaz, Determination of the critical micelle concentration of surfactants using the fluorescent probe N-phenyl-1-naphthylamine. Anal. Biochem. 152, 250–255 (1986). https://doi.org/10.1016/0003-2697(86)90406-9
T. Saitoh, K. Taguchi, M. Hiraide, Evaluation of hydrophobic properties of sodium dodecylsulfate/γ-alumina admicelles based on fluorescence spectra of N-phenyl-1-naphthylamine. Anal. Chim. Acta 454, 203–208 (2002). https://doi.org/10.1016/S0003-2670(01)01575-6
T. Saitoh, T. Kondo, M. Hiraide, Concentration of chlorophenols in water to dialkylated cationic surfactant-silica gel admicelles. J. Chromatogr. A 1164, 40–47 (2007). https://doi.org/10.1016/j.chroma.2007.07.021
W.L. Klotz, M.R. Schure, J.P. Foley, Determination of octanol-water partition coefficients of pesticides by microemulsion electrokinetic chromatography. J. Chromatogr. A 930, 145–154 (2001). https://doi.org/10.1016/S0021-9673(01)01171-2
A. Bonnechère, V. Hanot, R. Jolie, M. Hendrickx, C. Bragard, T. Bedoret, J.V. Loco, Effect of household and industrial processing on levels of five pesticide residues and two degradation products in spinach. Food Control 25, 397–406 (2012). https://doi.org/10.1016/j.foodcont.2011.11.010
J.G. Weers, D.R. Scheuing, Structure/performance relationships in monoalkyl/dialkyl cationic surfactant mixtures. J. Colloid Interface Sci. 145, 563–580 (1991). https://doi.org/10.1016/0021-9797(91)90386-M
A. Caria, O. Regev, A. Khan, Surfactant-polymer interactions: Phase diagram and fusion of vesicle in the didodecyldimethylammonium bromide-poly(ethylene oxide)-water system. J. Colloid Interface Sci. 200, 19–30 (1998). https://doi.org/10.1006/jcis.1997.5310
Z.E. Proverbio, P.C. Schulz, J.E. Puig, Aggregation of the aqueous dodecyltrimethylammonium bromide-didodecyldimethylammonium bromide system at low concentration. Colloid Polym. Sci. 280, 1045–1052 (2002). https://doi.org/10.1007/s00396-002-0731-y
J.C. Villedieu, A. de Savignac, J.P. Calmon, Kinetics and mechanisms of hydrolysis of dicarboximide fungicides in micellar media. J. Agric. Food Chem. 43, 1948–1953 (1995). https://doi.org/10.1021/jf00055a035
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This study was supported by a JSPS KAKENHI (19J20799).
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The funding has been received from Japan Society for the Promotion of Science with Grant no. 19J20799.
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Thao, N.T.T., Oiwa, M., Hayashi, H. et al. Removal and detoxification of iprodione in water using didodecyldimethylammonium bromide-montmorillonite organoclay and manganese dioxide. ANAL. SCI. (2024). https://doi.org/10.1007/s44211-024-00576-w
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DOI: https://doi.org/10.1007/s44211-024-00576-w