Biodegradation of the insecticide N,N-diethyl-m-toluamide by fungi: Identification and toxicity of metabolites

Department of Environmental Science and Engineering, Gwangju Institute of Science and Technology, Gwangju, 500-712, Korea.
Archives of Environmental Contamination and Toxicology (Impact Factor: 1.96). 05/2005; 48(3):323-8. DOI: 10.1007/s00244-004-0029-9
Source: PubMed

ABSTRACT Fungi (Cunninghamella elegans ATCC 9245, Mucor ramannianus R-56, Aspergillus niger VKMF-1119, and Phanerochaete chrysosporium BKMF-1767) were tested to elucidate the biologic fate of the topical insect repellent N,N-diethyl-m-toluamide (DEET). The elution profile obtained from analysis by high-pressure liquid chromatography equipped with a reverse-phase C-18 column, showed that three peaks occurred after incubation of C. elegans, with which 1 mM DEET was combined as a final concentration. The peaks were not detected in the control experiments with either DEET alone or tested fungus alone. The metabolites produced by C. elegans exhibited a molecular mass of 207 with a fragment ion (m/z) at 135, a molecular mass of 179 with an m/z at 135, and a molecular mass of 163 with an m/z at 119, all of which correspond to N,N-diethyl-m-toluamide-N-oxide, N-ethyl-m-toluamide-N-oxide, and N-ethyl-m-toluamide, respectively. M. ramannianus R-56 also produced N, N-diethyl-m-toluamide-N-oxide and N-ethyl-m-toluamide but did not produce N-ethyl-m-toluamide-N-oxide. For the biologic toxicity test with DEET and its metabolites, the freshwater zooplankton Daphnia magna was used. The biologic sensitivity in decreasing order was DEET > N-ethyl-m-toluamide > N,N-diethyl-m-toluamide-N-oxide. Although DEET and its fungal metabolites showed relatively low mortality compared with other insecticides, the toxicity was increased at longer exposure periods. These are the first reports of the metabolism of DEET by fungi and of the biologic toxicity of DEET and its fungal metabolites to the freshwater zooplankton D. magna.

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    • "N,N-diethyl-3-methylbenzamide (DEET) is still considered the best available product, repelling a wide variety of insects, ticks, and mites [8]. Though DEET is not expected to bioaccumulate, the amounts present in the environment have been shown to be toxic to some species of zooplankton and fish [9] [10]. In humans, the repellent may cause insomnia, mood disturbances, impaired cognitive functions, seizures, toxic encephalopathy, and allergic reactions [11] [12] [13]. "
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    Journal of Parasitology Research 02/2014; 2014:434506. DOI:10.1155/2014/434506
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    • "It may bioaccumulate – increasing in concentrations in the bodies of hosts as it moves up the foodchain. As thousands of backcountry sojourners spray repellent onto their clothes even now, so molecules of DEET drift into streams and lakes, permeating small organisms in the water and perhaps gathering in Sierra fish (Seo et al. 2005). What will the chemical do to them? "
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    • "The filtrate was evaporated with a rotary evaporator (Eyela, Japan) under a vacuum. The residue was dissolved in 1 ml methanol and filtered using polyvinylidene difluoride syringe filters for HPLC analysis (Seo et al. 2005). Purification was carried out with preparative HPLC. "
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