Occurrence of a nitro metabolite of a defined nonylphenol isomer in soil/sewage sludge mixtures

Uniformly [14C]-ring-labeled 4-(3,5-dimethyl-3-heptyl)phenol (353-nonylphenol) is a highly relevant isomer of the technical nonylphenol mixture. We studied the sorption, desorption, and degradation of the synthesized isomer in an agricultural sandy loam at various soil/sewage sludge ratios. Sorption of 353-nonylphenol was high and differed with the amount of suspended soil in water. log Koc values, which are used to assess the risk of nonylphenol, ranged from 3.80 to 5.75. Desorption was slow and low and resulted in constant concentrations of about 15 ng/L353-nonylphenol in water after several desorption steps. In degradation studies up to 6% of the applied 353-nonylphenol in soil was volatilized; we consider this an important source of nonylphenol in the environment. With increasing amounts of sewage sludge in the soil/sewage sludge mixtures, 353-nonylphenol was stabilized, probably because of the lack of oxygen in sludge aggregates even under oxic conditions in flow-through systems. Unexpectedly, a less-polar metabolite was detected in amounts up to 40% of the applied nonylphenol after 135 days of incubation. This novel metabolite was identified as 4-(3,5-dimethyl-3-heptyl)-2-nitrophenol. This product formation might indicate the existence of novel metabolic pathways of nonylphenol in the environment.