Abstract
Aerobic degradation experiments with the racemic mixtures of mecoprop and dichlorprop revealed that activated sludge collected from the aeration tank of a municipal waste water treatment plant degraded both enantiomers of mecoprop and dichlorprop within 7 days, albeit in an enantioselective manner; the (S) enantiomers were preferentially degraded. Mecoprop, dichlorprop, and 2,4-D were completely metabolized under aerobic conditions, as shown by the 86–98% elimination of dissolved organic carbon. Under anaerobic conditions, the concentration of 2,4-D decreased exponentially with a first-order reaction rate constant of 0.24 per day and without a lag-phase. After an incubation time of 17 days, 2,4-D was completely removed. 2,4-Dichlorophenol was the main metabolite of anaerobic 2,4-D degradation; only traces of 4-chlorophenol were detected. In contrast, the chiral phenoxypropionic acid herbicides mecoprop and dichlorprop persisted under anaerobic conditions during 49 days of incubation.
Similar content being viewed by others
References
Alder AC, Siegrist H, Gujer W & Giger W (1990) Behaviour of NTA and EDTA in biological wastewater treatment. Water Res. 24: 733–742
Alexander M & Aleem MIH (1961) Effect of chemical structure on microbial decomposition of aromatic herbicides. Agric. Food Chem. 9: 44–47
Anonymous (1995) Preventol® B2, Produkt-Information. Bayer AG, Leverkusen
Ariëns EJ (1989) Racemates — an impediment in the use of drugs and agrochemicals. In: Krstulovic AM (Ed) Chiral Separations by HPLC (pp 31–68). Ellis Horwood Limited, Chichester, UK
Boyd S & Shelton DR (1984) Anaerobic biodegradation of chlorophenols in fresh an acclimated sludge. Appl. Environ. Microbiol. 47: 272–277
Buser H-R & Müller MD (1997) Conversion reactions of various phenoxyalkanoic acid herbicides in soil. 2. Elucidation of the enantiomerization process of chiral phenoxy acids from incubation in a D2O/soil system. Environ. Sci. Technol. 31: 1960–1967
Buser H-R & Müller MD (1995) Isomer and enantioselective degradation of hexachlorocyclohexane isomers in sewage sludge under anaerobic conditions. Environ. Sci. Technol. 29: 664–672
Buser H-R & Müller MD (1998) Occurrence and Transformation Reactions of Chiral and Achiral Phenoxyalkanoic Acid Herbicides in Lakes and Rivers in Switzerland. Environ. Sci. Technol. 32: 626–633
Fielding M, Barcelo D, Helweg A, Galassi S, Torstensson L, Van Zoonen P, Wolter R & Angeletti G (1992) Pesticides in ground and drinking water. E. Guyot SA, Brussels
Garrison AW, Schmitt P, Martens D & Kettrup A (1996) Enantiomeric selectivity in the environmental degradation of dichlorprop as determined by high-performance capillary electrophoresis. Environ. Sci. Technol. 30: 2449–2455
Gintautas PA, Daniel SR & Macalady DL (1992) Phenoxyalkanoic acid herbicides in municipal landfill leachates. Environ. Sci. Technol. 26: 517–521
Heron G & Christensen TH (1992) Degradation of the herbicide mecoprop in an aerobic aquifer determined by laboratory batch studies. Chemosphere 24: 547–557
Karunen P, Heinonen S & Lyli O (1978) Persistence of mecoprop in northern and southwestern Finland. Annales Universitatis Turkuensis. Ser. A. II. Biologica-Geographica-Geologica 60: 25–30
Kohler H-PE, Angst W, Giger W, Kanz C, Müller S & Suter MJ-F (1997) Environmental fate of chiral pollutants-the necessity of considering stereochemistry. Chimia 51: 947–951
Ludwig P, Gunkel W & Hühnerfuss H (1992) Chromatographic separation of the enantiomers of marine pollutants. Part 5: Enantioselective degradation of phenoxycarboxylic acid herbicides by marine microorganisms. Chemosphere 24: 1423–1429
Mikkesell MD & Boyd SA (1985) Reductice dechlorination of the pesticides 2,4-D, 2,4,5-T, and pentachlorophenol in anaerobic sludges. J. Environ. Qual. 14: 337–340
Müller MD & Buser H-R (1997) Conversion reactions of various phenoxyalkanoic acid herbicides in soil. 1. Enantiomerization and enantioselective degradation of the chiral 2-phenoxypropionic acid herbicides. Environ. Sci. Technol. 31: 1953–1959
Müller MD, Buser H-R & Rappe C (1997) Enantioselective determination of various chlordane components and metabolites using high-resoluution gas chromatography with a β-cyclodextrin derivative as chiral selector and electron-capture negative ion mass spectrometry detection. Chemosphere 34: 2407–2417
Nickel K, Suter MJ-F & Kohler H-PE (1997) Involvement of two α-ketoglutarate-dependent dioxygenases in the enantioselective degradation of (R)-and (S)-mecoprop by Sphingomonas herbicidovorans MH. J. Bacteriol. 179: 6674–6679
Simoni S, Klinke S, Zipper C, Angst W & Kohler H-PE (1996) Enantioselective metabolism of chiral 3-phenylbutyric acid, an intermediate of linear alkylbenzene degradation, by Rhodococcus rhodochrous PB1. Appl. Environ. Microbiol. 62: 749–755
Smith AE (1989) Degradation, fate, and persistence of phenoxyalkanoic acid herbicides in soil. Rev. Weed Sci. 4: 1–24
Smith AE (1985) Identification of 4-chloro-2-methylphenol as a soil degradation product of ring-labelled [14C]mecoprop. Bull. Environ. Contam. Toxicol. 34: 656–660
Standing CN, Fredrickson AG & Tsuchiya HM (1972) Batch-and continuous-culture transients for two substrate systems. Appl. Microbiol. 23: 354–359
Tett VA, Willets AJ & Lappin-Scott HM (1994) Enantioselective degradation of the herbicide mecoprop [2-(2-methyl-4-chlorophenoxy)propionic acid] by mixed and pure bacterial cultures. FEMS Microbiol. Ecol. 14: 191–200
Tett VA, Willetts AJ & Lappin-Scott HM (1997) Biodegradation of the chlorophenoxy herbicide (R)-(+)-mecoprop by Alcaligenes denitrificans. Biodegradation 8: 43–52
Worthing CR & Hance RJ (1991) The Pesticide Manual — A World Compendium. The British Crop Protection Council, Farnham, UK
Zipper C, Bunk M, Zehnder AJB & Kohler H-PE (1998) Enantioselective uptake and degradation of the chiral herbicide dichlorprop [(RS)-2-(2,4-dichlorophenoxy)propanoic acid] by Sphingomonas herbicidovorans MH. J. Bacteriol. 180: 3368–3374
Zipper C, Nickel K, Angst W & Kohler H-PE (1996) Complete microbial degradation of both enantiomers of the chiral herbicide mecoprop ((RS)-2-(4-chloro-2-methylphenoxy)propionic acid) in an enantioselective manner by Sphingomonas herbicidovorans sp. nov. Appl. Environ. Microbiol. 62: 4318–4322
Zipper C, Suter MJ-F, Haderlein SB, Gruhl M & Kohler H-PE (1998) Changes in the enantiomeric ratio of (R)-to (S)-mecoprop indicate in situ biodegradation of this chiral herbicide in a polluted aquifer. Environ. Sci. Technol. 32: 2070–2076
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Zipper, C., Bolliger, C., Fleischmann, T. et al. Fate of the herbicides mecoprop, dichlorprop, and 2,4-D in aerobic and anaerobic sewage sludge as determined by laboratory batch studies and enantiomer-specific analysis. Biodegradation 10, 271–278 (1999). https://doi.org/10.1023/A:1008396022622
Issue Date:
DOI: https://doi.org/10.1023/A:1008396022622