Degradation, transformation, and non-extractable residue formation of nitrated nonylphenol isomers in an oxic soil.

Abstract Nitrated nonylphenols (NNPs) are main metabolites of the endocrine-disrupting nonylphenols in soil, yet their fate is unknown. Here, using four NNP isomers (NNP111, NNP112, NNP65, and NNP38), the degradation pattern of NNPs was investigated in an oxic soil for 266 days. Specifically, NNP111 was 14C-labeled to facilitate investigating its degradation, transformation, and non-extractable residue (NER) formation. NNPs degradation was isomer-specific with the decreasing order of half-life: NNP111 (126 days) > NNP112 (76 days) > NNP65 (14 days) > NNP38 (8.4 days), providing direct evidence of the greater persistence of NNPs in soil than their parent NPs. At the end of the incubation, 8.5 %, 7.3 %, and 39.9 % of 14C-NNP111 was mineralized, transformed to 2-amino-NP111, and formed NERs in active soil, respectively. In contrast, NERs in sterilized soils were significantly lower, amounting to 15.1 % and 17.3 % in autoclaved and γ-irradiated soil, respectively. The majority of the NERs (>70 %) were in humin fraction, in which type I NER was the predominant (>90 %) mode for NER formation. Our results provide comprehensive knowledge on the fate of NNPs in soil, demonstrating that isomer-specific behavior, transformation products of NNPs, and NER formation should be considered when evaluating environmental fate and risks of NNPs.