Fate and behavior of 14C-labelled ionic compounds in a soil simulation test

Abstract

The influence of an ionic functional group on the fate and behavior of chemicals in the environment has so far not been systematically investigated. This study, therefore, examines the following three substances with high structural similarity but differing charge: non-charged 4-n-dodecylphenol[phenylring-14C(U)] (14C-DP), negatively charged 4-n-dodecylbenzenesulfonicacid[phenylring-14C(U)] sodium salt (14C-DS−) and positively charged 4-n-dodecylbenzyltrimethylammonium chloride[phenylring-14C(U)] (14C-DA+). They were investigated in a soil simulation study according to the OECD 307 test guideline by measuring the distribution of the applied radioactivity (AR) among volatile, mineralized, extractable and non-extractable residues (NER) in one soil after 0, 1, 7, 14, 49, 84 and 124 days of incubation. Extractable portions of 14C were examined by means of radio-TLC and -HPLC analyses. Microbial activity of the soil incubated with and without 14C-DP, 14C-DS− and 14C-DA+ was determined measuring the reduction of dimethylsulfoxide (DMSO) over time. After 124 days of incubation highest mineralization could be observed for 14C-DS− (64.5% AR). Except CO2, no volatile residues were formed over time. Besides the parent compounds, polar (14C-DP, 14C-DS− and 14C-DA+) and nonpolar (14C-DA+) transformation products were detected. Highest amounts of 14C were extracted using methanol and were thus potentially bioavailable for soil microorganisms. Microbial activity was markedly higher in soil incubated with 14C-DP and 14C-DS− compared to 14C-DA+ or soil without any treatment. Half-lives (DT50 k2) at 18 °C were as follows: DA+ (61.8 days) > DS− (18.2 days) > DP (10.0 days). In case of the cationic compound and its transformation products we conclude that a higher sorption affinity to soil particles leads to reduced bioavailability for microorganisms and thus reduced mineralization resulting in a higher persistence compared to anionic and non-charged organic compounds in soil. The impact of our findings on the persistence assessment of chemicals when performing OECD guideline tests in soil, water-sediment and surface water is discussed.