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Synthesis of the DDT metabolite 2,4-dichloro-1-[2-chloro-1-(4-chlorophenyl)ethenyl]benzene (o-Cl-DDMU) and its detection in abiotic and biotic samples

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Abstract

Technical dichlorodiphenyltrichloroethane (DDT) has been used worldwide as a pesticide since the beginning of the 1940s. Due to its persistence, DDT residues are still ubiquitously distributed in the environment. Photochemical UV degradation has been shown to be a potent degradation path for DDT and most of the resulting photoproducts have been identified up to now. Nevertheless, in 2012, a new DDT metabolite, most likely formed photochemically from DDE, was detected in ray liver samples from Brazil, an area which is highly contaminated with DDT. This study includes photochemical generation, chemical synthesis and isolation of this compound which was verified to consist of both cis- and trans-2,4-dichloro-1-[2-chloro-1-(4-chlorophenyl)ethenyl]benzene. Both stereoisomers were resolved by gas chromatography on a polar capillary column and detected in more than 60 biotic (e.g. marine mammals, birds, human milk) and abiotic samples (fat deposits in kitchen hoods) from different areas all over the world. The stereoisomer distribution and concentrations (0.3–3.9% relative to corresponding 1,1-dichloro-2,2-bis(p-chlorophenyl) ethane (p,p′-DDE) levels) were determined by means of the synthesized analytical standard, indicating the widespread occurrence of this compound as an additional minor metabolite of DDT.

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Acknowledgements

The authors are thankful to Dr. Jürgen Conrad (Institute of Chemistry, Section of Bioorganic Chemistry, University of Hohenheim, Germany) for support of the NMR measurements. We gratefully acknowledge the German Academic Exchange Service (DAAD) for support of the internship of Katie Proctor within the DAAD/RISE Germany scholarship program 2016. Furthermore, we are thankful for all people who provided the samples available from previous studies. Dr. Gregor Scheiffarth from the Lower Saxony Tidelands National Park Administration (NLPV Wattenmeer) is acknowledged for providing us blubber samples from a stranded sperm whale. A special permission regarding the transportation and analysis of these samples in agreement with the Federal Act for the Protection of Nature was kindly provided by the Lower Saxony Tidelands National Park Administration.

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  1. Katie Proctor

    Present address: School of Chemistry, University of Birmingham, Edgbaston, B15 2TT, Birmingham, UK

  2. Korinna Bader

    Present address: Institute of Organic Chemistry, University of Stuttgart, Pfaffenwaldring 55, 70569, Stuttgart, Germany

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  1. Institute of Food Chemistry 170b, University of Hohenheim, Garbenstr. 28, 70599, Stuttgart, Germany

    Christoph Gallistl, Katie Proctor, Korinna Bader & Walter Vetter

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  1. Christoph Gallistl
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Correspondence to Walter Vetter.

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Gallistl, C., Proctor, K., Bader, K. et al. Synthesis of the DDT metabolite 2,4-dichloro-1-[2-chloro-1-(4-chlorophenyl)ethenyl]benzene (o-Cl-DDMU) and its detection in abiotic and biotic samples. Environ Sci Pollut Res 24, 16815–16828 (2017). https://doi.org/10.1007/s11356-017-9173-4

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