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Biodegradation of the Pyrethroid Pesticide Esfenvalerate by Marine-Derived Fungi

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Abstract

Esfenvalerate biodegradation by marine-derived fungi is reported here. Esfenvalerate (S,S-fenvalerate) and its main metabolites [3-phenoxybenzaldehyde (PBAld), 3-phenoxybenzoic acid (PBAc), 3-phenoxybenzyl alcohol (PBAlc), and 2-(4-chlorophenyl)-3-methylbutyric acid (CLAc)] were quantitatively analyzed by a validated method in triplicate experiments. All the strains (Penicillium raistrickii CBMAI 931, Aspergillus sydowii CBMAI 935, Cladosporium sp. CBMAI 1237, Microsphaeropsis sp. CBMAI 1675, Acremonium sp. CBMAI 1676, Westerdykella sp. CBMAI 1679, and Cladosporium sp. CBMAI 1678) were able to degrade esfenvalerate, however, with different efficiencies. Initially, 100 mg L−1 esfenvalerate (Sumidan 150SC) was added to each culture in 3 % malt liquid medium. Residual esfenvalerate (64.8–95.2 mg L−1) and the concentrations of PBAc (0.5–7.4 mg L−1), ClAc (0.1–7.5 mg L−1), and PBAlc (0.2 mg L−1) were determined after 14 days. In experiments after 7, 14, 21, and 28 days of biodegradation with the three most efficient strains, increasing concentrations of the toxic compounds PBAc (2.7–16.6 mg L−1, after 28 days) and CLAc (6.6–13.4 mg L−1, after 28 days) were observed. A biodegradation pathway was proposed, based on HPLC-ToF results. The biodegradation pathway includes PBAld, PBAc, PBAlc, ClAc, 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile, 3-(hydroxyphenoxy)benzoic acid, and methyl 3-phenoxy benzoate. Marine-derived fungi were able to biodegrade esfenvalerate in a commercial formulation and showed their potential for future bioremediation studies in contaminated soils and water bodies.

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Acknowledgments

W. G. Birolli and N. Alvarenga thank CNPq and FAPESP for their scholarships, respectively. A. L. M. Porto is grateful to the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq, grant no. 558062/2009-1) and Fundação de Amparo a Pesquisa do Estado de São Paulo (FAPESP, grant no. 2012/19934-0) for financial support. The authors express their gratitude to Roberto G. S. Berlinck (IQSC-USP, São Carlos, SP, Brazil) for providing the marine microorganisms, Timothy Roberts, who reviewed the English language of this paper, IHARABRAS S.A. for supplying the technical grade esfenvalerate and the commercial insecticide SUMIDAN 150SC, and the Chromatography Group (Instituto de Química de São Carlos—USP), including Guilherme M. Titato, for the LC-MS analysis (FAPESP, grant no. 2004/09498-2).

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  1. Laboratório de Química Orgânica e Biocatálise, Instituto de Química de São Carlos, Universidade de São Paulo, Av. João Dagnone, 1100, Ed. Química Ambiental, J. Santa Angelina, 13563-120, São Carlos, SP, Brazil

    Willian G. Birolli, Natália Alvarenga & André L. M. Porto

  2. Departamento de Ecologia e Biologia Evolutiva, Universidade Federal de São Carlos, Via Washington Luís, Km 235, 13565-905, São Carlos, SP, Brazil

    Mirna H. R. Seleghim

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  1. Willian G. Birolli
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  4. André L. M. Porto
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Correspondence to André L. M. Porto.

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I would like to declare on behalf of my co-authors that the work described was an original research that has not been published previously and neither is under consideration for publication elsewhere (partly or in full). No data, text, or theories by others are presented as if they were the author’s own. This article does not contain any studies with human participants or animals performed by any of the authors.

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Birolli, W.G., Alvarenga, N., Seleghim, M.H.R. et al. Biodegradation of the Pyrethroid Pesticide Esfenvalerate by Marine-Derived Fungi. Mar Biotechnol 18, 511–520 (2016). https://doi.org/10.1007/s10126-016-9710-z

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