Abstract
Reductive dechlorination of 2,4-dichlorophenoxyacetic acid (2,4-D) and 2,4,5-trichlorophenoxyacetic acid (2,4,5-T) was investigated in anaerobic sediments by non-adapted microorganisms and by microorganisms adapted to either 2,4- or 3,4-dichlorophenol (DCP). The rate of dechlorination of 2,4-D was increased by adaptation of sediment microorganisms to 2,4-DCP while dechlorination by sediment microorganisms adapted to 3,4-DCP displayed a lag phase similar to non-adapted sediment slurries. Both 2,4- and 3,4-DCP-adapted microorganisms produced 4-chlorophenoxyacetic acid by ortho-chlorine removal. Lag phases prior to dechlorination of the initial addition of 2,4,5-T by DCP-adapted sediment microorganisms were comparable to those from non-adapted sediment slurries. However, the rates of dechlorination increased upon subsequent additions of 2,4,5-T. Biodegradation of 2,4,5-T by sediment microorganisms adapted to 2,4- and/ or 3,4-DCP produced 2,5-D as the initial intermediate followed by 3-chlorophenol and phenol indicating a para > ortho > meta order of dechlorination. Dechlorination of 2,4,5-T, by either adapted or non-adapted sediment microorganisms, progressed without detection of 2,4,5-trichlorophenol as an intermediate.
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References
Bryant FO, Hale DD, Rogers JE (1991) Regiospecific dechlorination of pentachlorophenol by dichlorophenol-adapted microorganisms in freshwater, anaerobic sediment slurries. Appl Environ Microbiol 57:2293–2301
DeMarini DM, Brooks HG, Parkes DG (1990) Induction of prophage lambda by chlorophenols. Environ Mol Mutagen 15:1–9
DeWeerd KA, Concannon F, Suflita JM (1991) Relationship between hydrogen consumption, dehalogenation, and the reduction of sulfur oxyanion by Desulfomonile tiedjei. Appl Environ Microbiol 57:1929–1934
Don RH, Weightman AJ, Knackmuss HJ, Timmis KN (1985) Transposon mutagenesis and cloning analysis of the pathway for degradation of 2,4-dichlorophenoxyacetic acid and 3-chlorobenzoate in Alcaligenes eutrophus JMP134 (pJP4). J Bacteriol 161:85–90
Gibson SA, Suflita JM (1986) Extrapolation of biodegradation results to groundwater aquifers: reductive dehalogenation of aromatic compounds. Appl Environ Microbiol 52:681–688
Gibson SA, Suflita JM (1990) Anaerobic biodegradation of 2,4,5-trichlorophenoxyacaetic acid in samples from a methanogenic aquifer: stimulation by short-chain organic acids and alcohols. 56:1825–1832
Greer LE, Robinson JA, Shelton DR (1992) Kinetic comparison of seven strains of 2,4-dichlorophenoxyacetic acid-degrading bacteria. Appl Environ Microbiol 58:1027–1030
Griffith GD, Cole JR, Quensen III JF, Tiedje JM (1992) Specific deuteration of dichlorobenzoate during reductive dehalogenation by Desulfomonile tiedjei in D2O. Appl Environ Microbiol 58:409–411
Hale DD, Rogers JE, Wiegle J (1990) Reductive dechlorination of dichlorophenols by nonadapted and adapted microbial communities in pond sediment. Microb Ecol 20:185–196
Haugland RA, Schlemm DJ, Lyons III RP, Sferra PR, Chakrabarty AM (1990) Degradation of the chlorinated phenoxyacetate herbicides 2,4-dichlorophenoxyacetic acid and 2,4,5-trichlorophenoxyacetic acid by pure and mixed bacterial cultures. Appl Environ Microbiol 56:1357–1362
Hayes WJ Jr (1982) Herbicides. In: Pesticides studied in man. Williams and Wilkins, Baltimore, Md., pp 520–533
Karns JS, Kilbane JJ, Duttagupta S, Chakrabarty AM (1983) Metabolism of halophenols by 2,4,5-trichlorophenoxyacetic acid-degrading Pseudomonas cepacia. Appl Environ Microbiol 44:1176–1181
Keith LH, Telliard WA (1979) Priority pollutants I — a perspective. Environ Sci Technol 13:416–423
Kelly MP, Hallberg KB, Tuovinen OH (1989) Biological degradation of 2,4-dichlorophenoxyacetic acid: chloride mass balance in stirred tank reactors. Appl Environ Microbiol 55:2717–2719
Kilbane JJ, Chatterjee DK, Karns JS, Kellogg ST, Chakrabarty AM (1982) Biodegradation of 2,4,5-trichlorophenoxyacetic acid by a pure culture of Pseudomonas cepacia. Appl Environ Microbiol 44:72–78
Kuhn EP, Suflita JM (1989) Dehalogenation of pesticides by anaerobic microorganisms in soils and groundwater — a review. In: Sawhney BL, Brown K (eds) Reactions and movement of organic chemicals in soil. Soil Sci Soc Am Special Publication no. 22, pp 111–180
Leahy JG, Colwell RR (1990) Microbial degradation of hydrocarbons in the environment. Microbiol Rev 54:305–315
Lee MD, Thomas JM, Borden RC, Bedient PB, Ward CH (1988) Biorestoration of aquifers contaminated with organic compounds. Crit Rev Environ Control 18:29–89
Madsen T, Aamand J (1992) Anaerobic transformation and toxicity of trichlorophenols in a stable enrichment culture. Appl Environ Microbiol 58:557–561
Mikesell MD, Boyd SA (1985) Reductive dechlorination of the pesticides 2,4-D and 2,4,5-T and pentachlorophenol in anaerobic sludges. J Environ Qual 14:337–340
Neilson JW, Josephson KL, Pillai SD, Pepper IL (1992) Polymerase chain reaction and gene probe detection of the 2,4-dichlorophenoxyacetic acid degradation plasmid, pJP4. Appl Environ Microbiol 58:1271–1275
Niles L, Vogel TM (1991) Identification of the proton source for the microbial reductive dechlorination of 2,3,4,5,6-pentachlorobiphenyl. Appl Environ Microbiol 57:2771–2774
Pemberton JM, Corney B, Don RH (1979) Evolution and spread of pesticide degrading ability among soil microorganisms. In: Timmis KN, Puhler A (eds) Plasmids of medical, environmental and commercial importance. Elsevier/North-Holland Publishing Co., Amsterdam, pp 287–299
Short KA, Doyle JD, King RJ, Seidler RJ, Stotzky G, Olsen RH (1991) Effects of 2,4-dichlorophenol, a metabolite of a genetically engineered bacterium, and 2,4-dichlorophenoxyacetate on some microorganism-mediated ecological processes in soil. Appl Environ Microbiol 57:412–418
Stormo KE, Crawford RL (1992) Preparation of encapsulated microbial cells for environmental applications. Appl Environ Microbiol 58:727–730
Struijs J, Rogers JE (1989) Reductive dehalogenation of dichloroanilines by anaerobic microorganisms in fresh and dichlorophenol-acclimated pond sediment. Appl Environ Microbiol 55:2527–2531
Suflita JM, Stout J, Tiedje JM (1984) Dechlorination of (2,4,5-trichlorophenoxy)acetic acid by anaerobic microorganisms. J Agric Food Chem 32:218–221
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Bryant, F.O. Biodegradation of 2,4-dichlorophenoxyacetic acid and 2,4,5-trichlorophenoxyacetic acid by dichlorophenol-adapted microorganisms from freshwater, anaerobic sediments. Appl Microbiol Biotechnol 38, 276–281 (1992). https://doi.org/10.1007/BF00174483
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DOI: https://doi.org/10.1007/BF00174483