Categorizing chlordecone potential degradation products to explore their environmental fate

• Published in: The Science of the total environment Vol. 574; pp. 781 - 795
• Main Authors: Benoit, Pierre, Mamy, Laure, Servien, Rémi, Li, Ziang, Latrille, Eric, Rossard, Virginie, Bessac, Fabienne, Patureau, Dominique, Martin-Laurent, Fabrice
• Format: Journal Article
• Language: English
• Published: Netherlands Elsevier B.V 01.01.2017
• Subjects: Biodegradation; Molecular modeling; Organochlorine pesticides; Partial least squares; ANE, Sweden, Stockholm; Biodegradation; Partial least squares; Molecular modeling; Organochlorine pesticides
• ISSN: 0048-9697; 1879-1026
• DOI: 10.1016/j.scitotenv.2016.09.094

Chlordecone (C10Cl10O; CAS number 143–50-0) has been used extensively as an organochlorine insecticide but is nowadays banned and listed on annex A in The Stockholm Convention on Persistent Organic Pollutants (POPs). Although experimental evidences of biodegradation of this compound are scarce, several dechlorination products have been proposed by Dolfing et al. (2012) using Gibbs free energy calculations to explore different potential transformation routes. We here present the results of an in silico classification (TyPol - Typology of Pollutants) of chlordecone transformation products (TPs) based on statistical analyses combining several environmental endpoints and structural molecular descriptors. Starting from the list of putative chlordecone TPs and considering available data on degradation routes of other organochlorine compounds, we used different clustering strategies to explore the potential environmental behaviour of putative chlordecone TPs from the knowledge on their molecular descriptors. The method offers the possibility to focus on TPs present in different classes and to infer their environmental fate. Thus, we have deduced some hypothetical trends for the environmental behaviour of TPs of chlordecone assuming that TPs, which were clustered away from chlordecone, would have different environmental fate and ecotoxicological impact compared to chlordecone. Our findings suggest that mono- and di-hydrochlordecone, which are TPs of chlordecone often found in contaminated soils, may have similar environmental behaviour in terms of persistence. [Display omitted] •TyPol, an in silico typology, was used to categorize 170 organochlorine molecules.•Clustering used both molecular descriptors and environmental behaviour.•Parent and transformation products represented various chemical families.•20 chlordecone putative transformation products (TPs) were categorized.•Combining two clustering allowed assessing the potential fate of chlordecone TPs.