Identification and ecotoxicity of degradation products of chloroacetamide herbicides from UV-treatment of water

Science of the Total Environment

Volumn 458-460, Issue , 2013, Pages 527-534

  Souissi, Yasmine ^a   Bouchonnet, Stéphane ^a   Bourcier, Sophie ^a   Kusk, Kresten Ole ^b   Sablier, Michel ^a   Andersen, Henrik Rasmus ^b  

^a LABORATOIRE HÉTÉROÉLÉMENTS ET COORDINATION   (France)

^b TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

Chloroacetamide; Mass spectrometry; Photolysis; Photoproducts; Toxicity

Indexed keywords

CHLOROACETAMIDE HERBICIDES; CHLOROACETAMIDES; LIQUID CHROMATOGRAPHY-MASS SPECTROMETRY; PHOTODEGRADATION PRODUCTS; PHOTOPRODUCTS; PSEUDOKIRCHNERIELLA SUBCAPITATA; TRANSFORMATION REACTIONS; WATER AND WASTEWATER TREATMENTS;

DECHLORINATION; DEGRADATION; GAS CHROMATOGRAPHY; HERBICIDES; MASS SPECTROMETRY; PHOTOLYSIS; WASTEWATER TREATMENT; WEED CONTROL;

TOXICITY;

ACETOCHLOR; ALACHLOR; METOLACHLOR; ORGANOCHLORINE DERIVATIVE;

DISINFECTION; ECOTOXICOLOGY; ENVIRONMENTAL DEGRADATION; HERBICIDE; IDENTIFICATION METHOD; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PHOTOLYSIS; ULTRAVIOLET RADIATION; WATER TREATMENT;

ANIMAL EXPERIMENT; ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIZATION; DAPHNIA MAGNA; DECHLORINATION; ECOTOXICITY; HYDROXYLATION; LIQUID CHROMATOGRAPHY; MASS FRAGMENTOGRAPHY; NONHUMAN; PHOTODEGRADATION; PHOTOLYSIS; PHOTOSYNTHESIS; PRIORITY JOURNAL; PSEUDOKIRCHNERIELLA SUBCAPITATA; QUADRUPOLE MASS SPECTROMETRY; TIME OF FLIGHT MASS SPECTROMETRY; TOXICITY TESTING; ULTRAVIOLET RADIATION; VIBRIO FISCHERI; WATER TREATMENT;

ACETAMIDES; ALIIVIBRIO FISCHERI; ANIMALS; CHLOROPHYTA; CHROMATOGRAPHY, LIQUID; DAPHNIA; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HERBICIDES; HYDROXYLATION; MASS SPECTROMETRY; PHOTOLYSIS; SOLID PHASE EXTRACTION; ULTRAVIOLET RAYS; WATER POLLUTANTS, CHEMICAL; WATER PURIFICATION;

EID: 84878187722     PISSN: 00489697     EISSN: 18791026     Source Type: Journal    
DOI: 10.1016/j.scitotenv.2013.04.064     Document Type: Article

References (57)

1. Barbash J.E., Thelin G.P., Kolpin D.W., Gilliom R.J. Major herbicides in ground water: results from the National Water-Quality Assessment. J Environ Qual 2001, 30:831-845.
2. Battaglinand JFaW Potential toxicity of pesticides measured in midwestern streams to aquatic organisms. Water Sci Technol 2002, 45:95-103.
3. Belden J.B., Gilliom R.J., Martin J.D., Lydy M.J. Relative toxicity and occurrence patterns of pesticide mixtures in streams draining agricultural watersheds dominated by corn and soybean production. Integr Environ Assess Manag 2007, 3:90-100.
4. Böger P., Matthes B., Schmalfuß J. Towards the primary target of chloroacetamides -new findings pave the way. Pest Manag Sci 2000, 56:497-508.
5. Bonnet J.L., Bonnemoy F., Dusser M., Bohatier J. Assessment of the potential toxicity of herbicides and their degradation products to nontarget cells using two microorganisms, the bacteria Vibrio fischeri and the ciliate Tetrahymena pyriformis. Environ Toxicol 2007, 22:78-91.
6. Bouchonnet S., Kinani S., Souissi Y., Bourcier S., Sablier M., Roche P., et al. Investigation of the dissociation pathways of metolachlor, acetochlor and alachlor under electron ionization - application to the identification of ozonation products. Rapid Commun Mass Spectrom 2011, 25:93-103.
7. Bouchonnet S., Bourcier S., Souissi Y., Genty C., Sablier M., Roche P., et al. GC-MSn andLC-MS/MS couplings for the identification of degradation products resulting from the ozonation treatment of Acetochlor. J Mass Spectrom 2012, 47(4):439-452.
8. Bourcier S., Poisson C., Souissi Y., Kinani S., Bouchonnet S., Sablier M. Elucidation of the decomposition pathways of protonated and deprotonated estrone ions: application to the identification of photolysis products. Rapid Commun Mass Spectrom 2010, 24:2999-3010.
9. Boxall A.B.A., Sinclair C.J. Assessment of the environmental properties and effects of pesticide degradation products. Pesticide Behaviour in Soils and Water 2001, 78:113-118.
10. Bull R.J., Reckhow D.A., Li X., Humpage A.R., Joll C., Hrudey S.E. Potential carcinogenic hazards of non-regulated disinfection by-products: haloquinones, halo-cyclopentene and cyclohexene derivatives, N-halamines, halonitriles, and heterocyclic amines. Toxicology 2011, 286:1-19.
11. Cabaj A., Sommer R., Schoenen D. Biodosimetry: model calculations for u.v. water disinfection devices with regard to dose distributions. Water Res 1996, 30:1003-1009.
12. Cavalier T.C., Lavy T.L., Mattice J.D. Persistence of selected pesticides in ground-water samples. Ground Water 1991, 29:225-231.
13. Coffinet S., Rifai A., Genty C., Souissi Y., Bourcier S., Sablier M., et al. Characterization of the photodegradation products of metolachlor: structural elucidation, potential toxicity and persistence. J Mass Spectrom 2012, 47:1582-1593.
14. Coupe R.H., Blomquist J.D. Water-soluble pesticides in finished water of community water supplies. J Am Water Works Assn 2004, 96:56-68.
15. Dimitrov S., Koleva Y., Schultz T.W., Walker J.D., Mekenyan O. Interspecies quantitative structure-activity relationship model for aldehydes: aquatic toxicity. Environ Toxicol Chem 2004, 23:463-470.
16. Dimou A.D., Sakkas V.A., Albanis T.A. Metolachlor photodegradation study in aqueous media under natural and simulated solar irradiation. J Agric Food Chem 2005, 53:694-701.
17. Dunlap P.V. Quorum regulation of luminescence in Vibrio fischeri. J Mol Microbiol Biotechnol 1999, 1:5-12.
18. EFSA Conclusion regarding the peer review of the pesticide risk assessment of the active substance acetochlor. EFSA scientifi{ligature}c report 153 2008, EFSA, EFSA, Parma.
19. EU Council Directive 98/83/EC on the Quality of Water Intended for Human Consumption, European Union [accessed February 12, 2013]. http://ec.europa.eu/environment/water/water-drink/index_en.html.
20. Fairchild J.F., Ruessler D.S., Haverland P.S., Carlson A.R. Comparative sensitivity of Selenastrum capricornutum and Lemna minor to sixteen herbicides. Arch Environ Contam Toxicol 1997, 32:353-357.
21. Fairchild J.F., Ruessler D.S., Carlson A.R. Comparative sensitivity of five species of macrophytes and six species of algae to atrazine, metribuzin, alachlor, and metolachlor. Environ Toxicol Chem 1998, 17:1830-1834.
22. Fatta-Kassinos D., Meric S., Nikolaou A. Pharmaceutical residues in environmental waters and wastewater: current state of knowledge and future research. Anal Bioanal Chem 2011, 399:251-275.
23. Fatta-Kassinos D., Vasquez M.I., Kümmerer K. Transformation products of pharmaceuticals in surface waters and wastewater formed during photolysis and advanced oxidation processes - degradation, elucidation of byproducts and assessment of their biological potency. Chemosphere 2011, 85:693-709.
24. Friedman C.L., Lemley A.T., Hay A. Degradation of chloroacetanilide herbicides by anodic fenton treatment. J Agric Food Chem 2006, 54:2640-2651.
25. Gascuel-Odoux C., Aurousseau P., Cordier M.-O., Durand P., Garcia F., Masson V., et al. A decision-oriented model to evaluate the effect of land use and agricultural management on herbicide contamination in stream water. Environ Modell Softw 2009, 24:1433-1446.
26. Hansen K.M.S., Andersen H.R. Energy effectiveness of direct UV and UV/H2O2 treatment of estrogenic chemicals in biologically treated sewage. Int J Photoenergy 2012, 2012:9.
27. Hijnen W.A.M., Beerendonk E.F., Medema G.J. Inactivation credit of UV radiation for viruses, bacteria and protozoan (oo)cysts in water: a review. Water Res 2006, 40:3-22.
28. Hladik M.L., Bouwer E.J., Roberts A.L. Occurrence and treatment of neutral chloroacetamide degradates in midwestern US drinking water. Abstr Pap Am Chem Soc 2005, 229:U69-U.
29. Hladik M.L., Hsiao J.J., Roberts A.L. Are neutral chloroacetamide herbicide degradates of potential environmental concern? Analysis and occurrence in the upper Chesapeake Bay. Environ Sci Technol 2005, 39:6561-6574.
30. Hladik M.L., Bouwer E.J., Roberts A.L. Neutral degradates of chloroacetamide herbicides: occurrence in drinking water and removal during conventional water treatment. Water Res 2008, 42:4905-4914.
31. Hollender J., Zimmermann S.G., Koepke S., Krauss M., McArdell C.S., Ort C., Singer H., Von Gunten U., Siegrist H. Elimination of organic micropollutants in a municipal wastewater treatment plant upgraded with a full-scale post-ozonation followed by sand filtration. Environ Sci Technol 2009, 43(20):7862-7869.
32. Horvat A.J.M., Babić S., Pavlović D.M., Ašperger D., Pelko S., Kaštelan-Macan M., et al. Analysis, occurrence and fate of anthelmintics and their transformation products in the environment. TrAC Trends Anal Chem 2012, 31:61-84.
33. ISO11348-3 Water quality -- determination of the inhibitory effect of water samples on the light emission of Vibrio fischeri (Luminescent bacteria test) -- Part 3: Method using freeze-dried bacteria 1998, International Organization for Standardization, Switzerland.
34. ISO6341 Water quality -- determination of the inhibition of the mobility of Daphnia magna Straus (Cladocera, Crustacea) -- acute toxicity test 1996, International Organization for Standardization.
35. ISO8692 Water quality -- Freshwater algal growth inhibition test with unicellular green algae 2004, International Organisation for Standardisation, Switzerland.
36. Kiely T., Donaldson D., Grube A. Pesticide industry sales and usage: 2000 and 2001 market estimates 2002, U.S. Environmental Protection Agency (USEPA), Washington, DC.
37. Kock M., Farre M., Martinez E., Gajda-Schrantz K., Ginebreda A., Navarro A., et al. Integrated ecotoxicological and chemical approach for the assessment of pesticide pollution in the Ebro River delta (Spain). J Hydrol 2010, 383:73-82.
38. Konstantinou I., Hela D., Albanis T. The status of pesticide pollution in surface waters (rivers and lakes) of Greece. Part I. Review on occurrence and levels. Environ Pollut 2006, 141(3):555-570. (ISSN 0269-7491).
39. Kosjek T., Heath E. Applications of mass spectrometry to identifying pharmaceutical transformation products in water treatment. TrAC Trends Anal Chem 2008, 27:807-820.
40. Kosjek T., Andersen H.R., Kompare B., Ledin A., Heath E. Fate of carbamazepine during water treatment. Environ Sci Technol 2009, 43:6256-6261.
41. Lewis S.E., Brodie J.E., Bainbridge Z.T., Rohde K.W., Davis A.M., Masters B.L., et al. Herbicides: a new threat to the Great Barrier Reef. Environ Pollut 2009, 157:2470-2484.
42. Li X.Y., Su Z.C., Li X., Zhang C.G., Zhang H.W. Assessing the effects of acetochlor on soil fungal communities by DGGE and clone library analysis. Ecotoxicology 2010, 19:1111-1116.
43. Matthes B., Boger P. Chloroacetamides affect the plasma membrane. Z Naturforsch, C: Biosci 2002, 57:843-852.
44. Mestankova H., Escher B., Schirmer K., von Gunten U., Canonica S. Evolution of algal toxicity during (photo)oxidative degradation of diuron. Aquat Toxicol 2011, 101:466-473.
45. Osano O., Admiraal W., Klamer H.J.C., Pastor D., Bleeker E.A.J. Comparative toxic and genotoxic effects of chloroacetanilides, formamidines and their degradation products on Vibrio fischeri and Chironomus riparius. Environ Pollut 2002, 119:195-202.
46. Reichenberger S., Bach M., Skitschak A., Frede H.-G. Mitigation strategies to reduce pesticide inputs into ground- and surface water and their effectiveness; a review. Sci Total Environ 2007, 384:1-35.
47. Richardson S.D. Disinfection by-products and other emerging contaminants in drinking water. TrAC Trends Anal Chem 2003, 22:666-684.
48. Richardson S.D. Environmental mass spectrometry: emerging contaminants and current issues. Anal Chem 2008, 80:4373-4402.
49. Richardson S.D., Plewa M.J., Wagner E.D., Schoeny R., DeMarini D.M. Occurrence, genotoxicity, and carcinogenicity of regulated and emerging disinfection by-products in drinking water: a review and roadmap for research. Mutat Res Rev Mutat Res 2007, 636:178-242.
50. Rocha C., Pappas E.A., C-h Huang Determination of trace triazine and chloroacetamide herbicides in tile-fed drainage ditch water using solid-phase microextraction coupled with GC-MS. Environ Pollut 2008, 152:239-244.
51. Shijin R. Phenol mechanism of toxic action classification and prediction: a decision tree approach. Toxicol Lett 2003, 144:313-323.
52. Souissi Y., Bourcier S., Bouchonnet S., Genty C., Sablier M. Estrone direct photolysis: by-product identification using LC-Q-TOF. Chemosphere 2011, 87(2):185-193.
53. Susan D.R. Disinfection by-products and other emerging contaminants in drinking water. TrAC Trends Anal Chem 2003, 22:666-684.
54. Ternes T.A., Meisenheimer M., McDowell D., Sacher F., Brauch H.J., Gulde B.H., et al. Removal of pharmaceuticals during drinking water treatment. Environ Sci Technol 2002, 36:3855-3863.
55. USEPA Final Contaminant Candidate List 3 Chemicals: Identifying the Universe. U.S. Environmental Protection Agency Available from:, [Available from: http://www.epa.gov/safewater/ccl/ccl3.html#chemical].
56. Virág D., Naár Z., Kiss A. Microbial toxicity of pesticide derivatives produced with UV-photodegradation. Bull Environ Contam Toxicol 2007, 79:356-359.
57. Wei J., Ye B., Wang W., Yang L., Tao J., Hang Z. Spatial and temporal evaluations of disinfection by-products in drinking water distribution systems in Beijing, China. Sci Total Environ 2010, 408:4600-4606.