The antiepileptic drug carbamazepine (CBZ) is one of the most frequently detected human pharmaceuticals in wastewater effluents and biosolids. Soil is a primary environmental compartment receiving CBZ through wastewater irrigation and biosolid application. In this study, we explored the transformation of CBZ to biologically active intermediates in soil. Both (14)C labeling and liquid chromatography-tandem mass spectrometry (LC-MS/MS) were used to track transformation kinetics and identify major degradation intermediates. Through 120 days of incubation under aerobic conditions, mineralization of CBZ did not exceed 2% of the spiked rate in different soils. Amendment of biosolids further suppressed mineralization. The fraction of non-extractable (i.e., bound) residue also remained negligible (<5%). On the other hand, CBZ was transformed to a range of degradation intermediates, including 10,11-dihydro-10-hydroxycarbamazepine, carbamazepine-10,11-epoxide, acridone-N-carbaldehyde, 4-aldehyde-9-acridone, and acridine, of which acridone-N-carbaldehyde was formed in a large fraction and appeared to be recalcitrant to further degradation. Electrocyclization, ring cleavage, hydrogen shift, carbonylation, and decarbonylation contributed to CBZ transformative reactions in soil, producing biologically active products. The persistence of the parent compound and formation of incomplete intermediates suggest that CBZ has a high risk for off-site transport from soil, such as accumulation into plants and contamination of groundwater.

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Chiral insecticide paichongding (IPP) is one of the prospective substitutes for imidacloprid used in China due to its higher activity against imidacloprid-resistant insects. However, little is known about the fate of IPP in soils, including especially the different behaviors among its stereoisomers. In this study, four stereoisomers of IPP were separated and applied in flooded soils. Kinetics of mineralization, extractable residues, and bound residues showed diastereoselectivity in IPP degradation, with enantiomers (5S,7R)-IPP (IPP-SR) and (5R,7S)-IPP (IPP-RS) being more readily mineralized and preferentially bound to soils than enantiomers (5R,7R)-IPP (IPP-RR) and (5S,7S)-IPP (IPP-SS). The overall mineralization was rather limited and did not exceed 4% of the spiked rate. Concurrent to the decreases of extractable residues, the fraction of bound residues increased with time and reached about 34% of the applied radioactivity for (14)C-IPP-SR and (14)C-IPP-RS as compared to about 23% for (14)C-IPP-RR or (14)C-IPP-SS. Soil properties such as organic matter content and pH likely contributed to the variability. Relatively rapid formation of bound residue suggests that IPP may be quickly detoxified in flooded paddy soil, decreasing the potential for off-site transport such as leaching or runoff, especially for enantiomers IPP-SR and IPP-RS.