Skip to main content
SpringerLink
Log in

Haloacetic acids, phytotoxic secondary air pollutants

  • Research Article
  • Published:
Environmental Science and Pollution Research Aims and scope Submit manuscript

Abstract

Haloacetic acids are atmospheric oxidation products of airborne C2-halocarbons which are important solvents and propellants. Levels of trichloroacetate (TCA) in conifer needles from mountain ranges in Germany (Black Forest, Erzgebirge) and from two sites in Finland are compared; TCA is present in conifer needles at concentrations up to 0.7 μmol/kg, MCA up to 0.2 μmol/kg. At the Finnish sites, TCA-concentrations and branch degeneration symptoms of Scots pine are correlated. Monochloroacetate (MCA) has been determined in needle samples from Southern Germany in concentrations exceeding its phytotoxicity threshold towards photoautotrophic organisms. Data on atmospheric chloroacetate levels in Germany are also given; ambient air levels of chloroacetic acids range from about 2 pmol/m3 (TCA) to 390 pmol/m3 (MCA). TCA and dichloroacetic acid (DCA) arise from atmospheric oxidation of airborne C2-chlorocarbons, while the source of MCA is not yet known; several tentative pathways are suggested.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. K. Schott;H.J. Schumacher: Die photochemische Chlorierung und die durch Chlor sensibilisierte photochemische Oxydation von Tetrachloräthylen. Z. Physikal. Chemie49, 107–125 (1941)

    Google Scholar 

  2. B.W. Gay;P.L. Hanst;J.J. Bufalini;R.C. Noonan: Atmospheric Oxidation of Chlorinated Ethylenes. Environ. Sci. Technol.10, 58–67 (1976)

    Article  CAS  Google Scholar 

  3. E.C. Tuazon;R. Atkinson;S.M. Aschman;M.A. Goodman;A.M. Winer: Atmospheric Reactions of Chloroethenes with the OH Radical. Intern. J. Chem. Kinetics20, 241–265 (1988)

    Article  CAS  Google Scholar 

  4. International Trade Commission USA. Chem. Eng. News70 (15) 17 (1992)

    Google Scholar 

  5. P. Fabian: Halogenated Hydrocarbons in the Atmosphere. In: O. Hutzinger (Ed.), The Handbook of Environmental Chemistry, Vol 4A, Springer Berlin, 1986, pp. 23–51

  6. P. Midgley: The Production and Release to Atmosphere of Industrial Halocarbons. Ber. Bunsenges. Phys. Chem.96, 293–296 (1992)

    CAS  Google Scholar 

  7. E.O. Edney;B.W. Gay;D.J. Driscoll: Chlorine Initiated Oxidation Studies of Hydrochlorofluorocarbons: Results for HCFC-123 and HCFC-1416. J. Atmos. Chem.12, 105–120 (1991)

    Article  CAS  Google Scholar 

  8. H. Frank;W. Frank: Chlorophyll-Bleaching by Atmospheric Pollutants. Naturwissenschaften72, 139–141 (1985)

    Article  CAS  Google Scholar 

  9. R. Debus;P. Schröder: Wirkungen von Halon 1211 (Bromchlordifluormethan) auf Kresse. VDI-Berichte 745, VDI-Verlag, Düsseldorf 1989, pp. 563–572

    Google Scholar 

  10. R.A. Peters: Lethal Synthesis and Carbon-Fluorine Compounds. In: Biochemical Lesions and Lethal Synthesis, Pergamon Press, Oxford, 1963, pp. 88–130

    Google Scholar 

  11. M.P. Quick: Sodium Monochloroacetate Poisoning of Cattle and Sheep. Vet. Rec.113, 155–156 (1983)

    CAS  Google Scholar 

  12. K.C. Barrons;R.W. Hummer: Basic Herbicidal Studies with Derivatives of TCA. Agricult. Chem.6, 48–121 (1951)

    Google Scholar 

  13. H. Zöttl: Untersuchungen über die Wirkung von Trichloracetat, und anderen Halogenacetaten auf pflanzliches Gewebe. Z. Naturforschg.8b, 317–323 (1953)

    Google Scholar 

  14. C. Foy: The Chlorinated Aliphatic Acids. In:P.C. Kearney andD.D. Kaufmann, Degradation of Herbicides, Marcel Dekker, New York, 1969, pp. 207–254

    Google Scholar 

  15. G. Matolcsy;M. Nädasy;V. Andriska: Pesticide Chemistry. Elsevier, Amsterdam, 1988, pp. 577–580

    Google Scholar 

  16. H. Frank;J. Vital;W. Frank: Oxidation of Airborne C2-Chlorocarbons to Trichloroacetic and Dichloroacetic Acid. Fresenius Z. Anal. Chem.333, 713 (1989)

    Article  Google Scholar 

  17. G.R. Fuchs;K. Bächmann: Ionen-chromatographische Bestimmung von Chloracetat und Dichloracetat in Niederschlagswasserproben. Fresenius Z. Anal. Chem.327, 205–212 (1987)

    Article  CAS  Google Scholar 

  18. I. Renner; R. Schleyer; D. Mühlhausen: Gefährdung der Grundwasserqualität durch anthropogene organische Luftverunreinigungen. VDI-Berichte Nr.837, 705–727 (1990)

  19. A. Artho;K. Grob;P. Giger: Trichloressigsäure in Oberflächen-, Grund-, und Trinkwässern. Mitteilung Gebiete Lebensm. Hyg.82, 487–491 (1991)

    CAS  Google Scholar 

  20. H. Frank: Airborne Chlorocarbons, Photooxidants, and Forest Decline. Ambio20, 13–18 (1991)

    Google Scholar 

  21. H. Frank;H. Scholl;S. Sutinen;Y. Norokorpi: Trichloroacetic Acid in Conifer Needles in Finland. Ann. Bot. Fennici29, 263–267 (1992)

    CAS  Google Scholar 

  22. H. Frank: Photoaktivierung luftgetragener Chlorkohlenwasserstoffe. Nachr. Chem. Tech. Lab.34, 15–20 (1986)

    CAS  Google Scholar 

  23. R. Oren; K.S. Werk; J. Meyer; E.D. Schulze. In: Forest Decline and Air Pollution, Springer Berlin, 1989, pp. 24 ff

  24. G. Bringmann;R. Kühn: Comparison of the Toxicity Thresholds of Water Pollutants to Bacteria, Algae, and Protozoa in the Cell Multiplication Inhibition Test. Water Res.14, 231–241 (1980)

    Article  CAS  Google Scholar 

  25. R. Kühn;M. Pattard: Results of the Harmful Effects of Water Pollutants to Green Algae (Scenedesmus suspicatus) in the Cell Multiplication Inhibition Test. Water Res.24, 31–38 (1990)

    Article  Google Scholar 

  26. Y. Ilvessalo: Metsänarvioiminen (W. Söderström Oy, Poroo, Helsinki, 1965), p. 231

    Google Scholar 

  27. E.L. Jukola-Sulonen; K. Mikkola; M. Salemaa: The Vitality of Conifers in Finland, 1986–88. In: P. Kauppi, P. Anttilla, K. Kenttämies, Acidification in Finland, Springer Berlin, 1990, pp. 523–560

  28. H. Frank;A. Vincon;J. Reiss;H. Scholl: Trichloroacetic Acid in the Foliage of Forest Trees. J. High Resol. Chromatogr.13, 733–736 (1990)

    Article  CAS  Google Scholar 

  29. U. Hofmann;S. Holzer;C.O. Meese: Pentafluorophenyldiazoalkanes as Novel Derivatization Reagents for the Determination of Sensitive Carboxylic Acids by Gas Chromatography-Negative-Ion Mass Spectrometry. J. Chromatogr.508, 349–356 (1990)

    Article  CAS  Google Scholar 

  30. D.J. Eatough;C.L. Benner;J.M. Bayona;G. Richards;J.D. Lamb;M.L. Lee;E.A. Lewis;L.D. Hansen: Chemical Composition of Environmental Tobacco Smoke 1. Gas-Phase Acids and Bases. Environ. Sci. Technol.23, 679–687 (1989)

    Article  CAS  Google Scholar 

  31. T. Murashige;F. Skoog: A Revised Medium for Rapid Growth and Bioassays with Tobacco Tissue Cultures. Physiol. Plant.15, 473–497 (1962)

    Article  CAS  Google Scholar 

  32. „Water Quality — Fresh Water Algal Growth Inhibition Test withScenedesmus suspicatus andSelenastrum capricornutum“, International Standard ISO/DIS 8692, Geneva, Switzerland (1989)

  33. H. Scholl: Ph. D. Thesis, University of Tübingen, 1993

  34. Daten zur Umwelt 1990/91, Umweltbundesamt, Schmidt, Berlin, 1992, pp. 164–179

  35. P.N.P. Chow: Adsorption and Dissipation of TCA by Wheat and Oats. Weed Sci.18, 492–496 (1970)

    CAS  Google Scholar 

  36. H. Kramer;H. Gussone;R. Schober: Waldwachstumslehre. Paul Parey, Hamburg, 1988, p. 23

    Google Scholar 

  37. W. Frank;H.J.C. Neves;H. Frank: Levels of Airborne Halocarbons at Urban and Mountain Forest Sites in Germany and at the Atlantic Coast. Chemosphere23, 609–626 (1991)

    Article  CAS  Google Scholar 

  38. B.J. Finlayson-Pitts;J.N. Pitts: Atmospheric Chemistry. Wiley & Sons, New York, 1986, p. 1026

    Google Scholar 

  39. R. Prinn;D. Cunnold;R. Rasmussen;P. Simmonds;F. Alyea;A. Crawford;P. Fraser;R. Rosen: Atmospheric Trends in Methylchloroform and the Global Average for the Hydroxyl Radical. Science238, 945–950 (1987)

    Article  CAS  Google Scholar 

  40. H.B. Singh;J.F. Kasting: Chlorine-Hydrocarbon Photochemistry in the Marine Troposphere and Lower Stratosphere. Atmos. Chem.7, 261–285 (1988)

    Article  CAS  Google Scholar 

  41. P. Herbert; P. Carbonnier; L. Rivolta; M. Servais; F. van Mensch; I. Campbell: The Occurrence of Chlorinated Solvents in the Environment. Chem. Ind.1986, 861–869

  42. T.M. Vogel;P.L. McCarty: Biotransformation of Tetrachloroethylene to Trichloroethylene, Dichloroethylene, Vinylchloride, and Carbon Dioxide under Methanogenic Conditions. Appl. Environ. Microbiol.49, 1080–1983 (1985)

    CAS  Google Scholar 

  43. M. Trevisan;C. Montepiani;L. Ragozza;C. Bartoletti;E. Ioanilli;A.A. Del Re: Pesticides in Rainfall and Air in Italy. Environ. Pollution80, 31–39 (1993)

    Article  CAS  Google Scholar 

  44. F. Wania;D. Mackay: Global Fractionation and Cold Condensation of Low Volatility Organochlorine Compounds in Polar Regions. Ambio22, 10–18 (1993)

    Google Scholar 

  45. S. Juuti;A. Hirvonen;J. Tarhanen;J.M. Holopainen;J. Ruuskanen: Trichloroacetic Acid in Pine Needles in the Vicinity of a Pulp Mill. Chemosphere26, 1859–1868 (1993)

    Article  Google Scholar 

  46. Beilstein, Handbuch der Organischen Chemie, Volume 2, Springer Berlin; (1920) pp. 194 ff; E1 (1928) pp. 87 ff; E2 (1942) pp. 187 ff.

  47. T. Ashenden;T. Mansfield: Influence of Wind Speed on the Sensitivity of Ryegrass to SO2. J. Experimental Botany28, 729–735 (1977)

    Article  CAS  Google Scholar 

  48. A.J. Haagen-Smit: Chemistry and Physiology of Los Angeles Smog. Industr. Eng. Chem.44, 1342–1348 (1954)

    Article  Google Scholar 

  49. H. Frank: Waldschäden durch Photooxidantien? Nachr. Chem. Tech. Lab.32, 298–305 (1984)

    CAS  Google Scholar 

  50. O. Meinander; P. Paatero: Application of Singular Value Decomposition to High Resolution Spectrometry for Forest Damage Detection. Contribution to the Conference on Environmetrics, 17–21 Aug. 1992

  51. F. Zabel: Atmospheric Degradation of Volatile Halocarbons. Toxicol. Environ. Chem. 1993, in press

  52. M.B. Chenoweth: Monofluoroacetic Acid and Related Compounds. Pharmacol. Rev.1, 383–424 (1949)

    Google Scholar 

  53. J.S.C. Marais: Monofluoroacetic Acid. The Toxic Principle of „Gifblaar“Dichapethalum Cymosum. J. Vet. Sci. Animal Ind.20, 67–73 (1944)

    CAS  Google Scholar 

  54. G. Bringmann;R. Kühn: Grenzwerte der Schadwirkung wassergefährdender Stoffe gegen Blaualgen (Microcystis aeruginosa) und Grünalgen (Scenedesmus quadricauda) im Zellvermehrungshemmtest. Vom Wasser50, 45–60 (1978)

    CAS  Google Scholar 

  55. J.L. Hilton;J.S. Ard;L.L. Jansen;W.A. Gentner: The Pantothenate-Synthesizing Enzyme, a Metabolie Site in the Herbicidal Action of Chlorinated Aliphatic Acids. Weeds7, 381–396 (1959)

    Article  CAS  Google Scholar 

  56. B.E. Juniper: The Effect of Pre-Emergent Treatment of Peas with Trichloroacetic Acid on the Submicroscopic Structure of the Leaf Surface. New Phytologist58, 1–5 (1959)

    Article  Google Scholar 

  57. R. Schell; U. Kristen: Trichloressigsäure begünstigt Pilzinfektionen von Fichtennadeln. InW. Michaelis and J. Bauch (Eds.): Luftverunreinigungen und Waldschäden am Standort „Postturm“, Forstamt Farchau/Ratzeburg. GKSS-Research Center Geesthacht,1992, pp. 353–363

  58. S. Tietz;S. Schneider;J. Gill;A. Wild: PEPC-Aktivität, Biochemischer Indikator für den Schädigungsgrad bei Fichten. UWSF-Z. Umweltchem. Ökotox.3, 206–209 (1991)

    Article  Google Scholar 

  59. E.D. Schulze; O.L. Lange; R. Oren: Forest Decline and Air Pollution, Springer Berlin 1989, p. 193–207

  60. G. Eriksson;S. Jensen;H. Kylin;W. Strachan: The Pine Needle as a Monitor of Atmospheric Pollution. Nature341, 42–44 (1989)

    Article  CAS  Google Scholar 

  61. A. Reischl; M. Reissinger; O. Hutzinger: Organic Micropollutants and Plants. In:E.D. Schulze, O.L. Lange; R. Oren: Forest Decline and Air Pollution, Springer Berlin 1989, p. 193–207

  62. H. Geyer;I. Scheunert;F. Korte: The Effect of Organic Environmental Chemicals on the Growth of the AlgaeScenedesmus Subspicatus: A Contribution to Environmental Biology. Chemosphere14, 1355–1369 (1985)

    Article  CAS  Google Scholar 

  63. M. Hinkel;A. Reischl;K.-W. Schramm;F. Trautner;M. Reis-Singer;O. Hutzinger: Concentration Levels of Nitrated Phenols in Conifer Needles. Chemosphere18, 2433–2439 (1989)

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute for Toxicology, University of Tübingen, Wilhelmstraße 56, D-72074, Tübingen, Germany

    Hartmut Frank, Harald Scholl & Dirk Renschen

  2. Laboratoire de Biologie Végétale Appliquée, Université Louis Pasteur, 3, rue de l’Argonne, F-67000, Strasbourg, France

    Benoît Rether & Abdelkrim Laouedj

  3. Finnish Forest Research Institute, Rovaniemi Research Station, P. O. Box 16, FIN-96301, Rovaniemi, Finland

    Yrjö Norokorpi

Authors
  1. Hartmut Frank
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Harald Scholl
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Dirk Renschen
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Benoît Rether
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Abdelkrim Laouedj
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Yrjö Norokorpi
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Frank, H., Scholl, H., Renschen, D. et al. Haloacetic acids, phytotoxic secondary air pollutants. Environ. Sci. & Pollut. Res. 1, 4–14 (1994). https://doi.org/10.1007/BF02986917

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02986917

Keywords

Search

Navigation