Enantioselective biodegradation of mecoprop in aerobic and anaerobic microcosms

Natural attenuation of mecoprop has been studied by determining changes in enantiomeric fraction in different redox environments down gradient from a landfill in the Lincolnshire limestone. Such changes could be due to differential metabolism of the enantiomers, or enantiomeric inversion. In order to confirm the processes occurring in the field, microcosm experiments were undertaken using limestone acclimatised in different redox zones. No biodegradation was observed in the methanogenic, sulphate-reducing or iron-reducing microcosms. In the nitrate-reducing microcosm (S)-mecoprop did not degrade but (R)-mecoprop degraded with zero order kinetics at 0.65 mg l(-1)day(-1) to produce a stoichiometric equivalent amount of 4-chloro-2-methylphenol. This metabolite only degraded when the (R)-mecoprop disappeared. In aerobic conditions (S)- and (R)-mecoprop degraded with zero order kinetics at rates of 1.90 and 1.32 mg l(-1)day(-1) respectively. The addition of nitrate to dormant iron-reducing microcosms devoid of nitrate stimulated anaerobic degradation of (R)-mecoprop after a lag period of about 20 days and was associated with the production of 4-chloro-2-methylphenol. Nitrate addition to sulphate-reducing/methanogenic microcosms did not stimulate mecoprop degradation. However, the added nitrate was completely utilised in oxidising sulphide to sulphate. There was no evidence for enantiomeric inversion. The study reveals new evidence for fast enantioselective degradation of (R)-mecoprop under nitrate-reducing conditions.