Chiral current-use herbicides in Ontario streams

Environmental Science and Technology

Volumn 42, Issue 22, 2008, Pages 8452-8458

  Kurt Karakus, Perihan Binnur ^a   Bidleman, Terry F ^a   Muir, Derek C G ^a   Cagampan, Steve J ^a   Struger, John ^a   Sverko, Ed ^a   Small, Jeff M ^a   Jantunen, Liisa M ^a  

^a ENVIRONMENT CANADA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; CHIRALITY; DEGRADATION; ENANTIOMERS; FRUIT JUICES; HERBICIDES; PEST CONTROL; RIVERS; STEREOCHEMISTRY; WATERSHEDS; WEED CONTROL; AGRICULTURE; LANDFORMS;

AGRICULTURAL WATERSHEDS; CHIRAL CURRENTS; ENANTIOMER FRACTIONS; HIGHER CONCENTRATIONS; LOWER CONCENTRATIONS; MECOPROP; METOLACHLOR; ONTARIO; ROW CROPS; S/R RATIOS; STEREOSELECTIVE; STREAM WATERS; URBAN LANDS; URBAN WATERSHEDS;

LANDFORMS; HERBICIDES;

HERBICIDE; MECOPROP; METOLACHLOR;

AGRICULTURAL LAND; COMPARATIVE STUDY; DEGRADATION; HERBICIDE; STREAMWATER; WATER POLLUTION; WATERSHED;

ARTICLE; CHIRALITY; CONCENTRATION (PARAMETERS); ENANTIOMER; STEREOISOMERISM; WATER CONTAMINATION; WATERSHED;

ANIMALS; HERBICIDES; MOLECULAR STRUCTURE; RIVERS; SEASONS; STEREOISOMERISM; WATER POLLUTANTS, CHEMICAL;

CANADA; NORTH AMERICA; ONTARIO [CANADA];

AGRICULTURAL WATERSHEDS; ENANTIOMER FRACTIONS; LAND USAGE; METOLACHLORS; ONTARIO; ROW CROP; STEREO-SELECTIVE; STREAM WATER; URBAN WATERSHED;

EID: 56449124288     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es8011854     Document Type: Article

References (25)

1. Brimble, S.; Bacchus, P.; Caux P.-Y. Pesticide Utilization in Canada: A compilation of current sales and use data;Environment Canada GoC Cat. No. En4-56/2005E-PDF; ISBN 0-662-42085-3; 2005.
2. Struger, J.; Fletcher, T. Occurrence of lawn care and agricultural pesticides in the Don River and Humber River watersheds (1998-2002). J. Great Lakes Res. 2007, 33, 887-905.
3. Zaruk, D.; Alaee, M.; Sverko, E.; Comba, M. Occurrence of triazine herbicides and metolachlor in the Niagara River and other major tributaries draining into Lake Ontario. Anal. Chim. Acta 1998, 376, 113-117.
4. CCME (Canadian Council of Ministers of the Environment). Appendix IX- A protocol for the derivation of water quality guidelines for the protection of aquatic life. In Canadian Water Quality Guidelines, Canadian Council of Resource and Environment Ministers, 1987; Prepared by the Task Force on Water Quality Guidelines.
5. [Updated and reprinted with minor revisions and editorial changes in Canadian environmental quality guidelines, Chapter 4, Canadian Council of Ministers of the Environment, 1999, Winnipeg].
6. Williams, A. Opportunities for chiral pesticides. Pest. Sci. 1996, 46, 3.
7. GarrisonA. W. Probing the enantioselectivity of chiral pesticides. Environ. Sci. Technol. 2006, 4016-23.
8. 2O/soil system. Environ. Sci. Technol. 1997, 31 (7), 1960-1967.
9. Müller, M. D.; Buser, H.-R. Conversion reactions of various phenoxyalkanoic acid herbicides in soil. 1. Enantiomerization and enantioselective degradation of the chiral 2-phenoxypropionic acid herbicides. Environ. Sci. Technol. 1997, 31, 1953-1959.
10. Magrans, J.; Alonzo-Prados, J.; Garcia-Baudin, J. Importance of considering pesticide stereoisomerism: proposal of a scheme to apply Directive 91/414/EEC framework to pesticide active substances manufactured as isomer mixtures. Chemosphere 2002, 49, 461-469.
11. Loos, M. A. Phenoxyalkanoic Acids. In Herbicides: Chemistry, Degradation and Mode of Action; Kearney, D. D.; Kaufman, P. C. Eds.; Marcel Dekker Inc.: New York, 1975; Vol. 1, pp2-101.
12. Buser, H.-R.; Poiger, T.; Müller, M. D. Changed enantiomer composition of metolachlor in surface water following the introduction of the enantiomerically enriched product to the market. Environ. Sci. Technol. 2000, 34 (13), 2690-2696.
13. Heron, G.; Christensen, T. H. Degradation of the herbicide mecoprop in an aerobic aquifer determined by laboratory batch studies. Chemosphere 1992, 24 (5), 547-557.
14. Saari, R. E.; Hogan, D. A.; Hausinger, R. P. Stereospecific degradation of the phenoxypropionate herbicide dichlorprop. J. Mol. Catal. B 1999, 6, 421-428.
15. Garrison, A. W.; Schmitt, Ph.; Kettrup, A. Enantiomeric selectivity in the environmental degradation of dichlorprop as determined by high-performance capillary electroforesis. Environ. Sci. Technol. 1996, 30 (8), 2449-2455.
16. Ludwig, P.; Gunkel, W.; Huhnerfuss, H. Chromatographic separation of the enantiomers of marine pollutants. Part 5: enantioselective degradation of phenoxy carboxylic acid herbicides by marine microorganisms. Chemosphere 1992, 24 (10), 1423-1429.
17. Romero, E.; Matallo, M. B.; Pena, A.; Sanchez-Rasero, F.; Schmitt-Kopplin, Ph.; Dios, G. Dissipation of racemic mecoprop and dichlorprop and their pure R-enantiomers in three calcareous soils with and without peat addition. Environ. Pollut. 2001, 111, 209-215.
18. Tett, V. A.; Willets, A. J.; Lappin-Scott, H. M. Enantioselective degradation of the herbicide mecoprop [2-(2-methyl-4-chlorophenoxy)propionic acid] by mixed and pure bacterial cultures. FEMS Microbiol. Ecol. 1994, 14, 191-200.
19. Zipper, C.; Suter, M.J.-F.; Haderlein, S. B.; Gruhl, M.; Kohler, H.-P.E. 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. 1998, 32, 2070-2076.
20. Buerge, I. J.; Poiger, T.; Müller, M. D.; Buser, H.-R. Enantioselective degradation of metalaxyl in soils: chiral preference changes with soil pH. Environ. Sci. Technol. 2003, 37, 2668-2674.
21. Müller, M. D.; Buser, H.-R. Environmental behavior of acetamide pesticide stereoisomers. 2. Stereo- and enantioselective degradation in sewage sludge and soil. Environ. Sci. Technol. 1995, 29, 2031-2037.
22. Buser, H.-R.; Müller, M. D. Occurrence of chiral and achiral phenoxyalkanoic acid herbicides in lakes and rivers in Switzerland. Environ. Sci. Technol. 1998, 32, 626-633.
23. Lee, H. B.; Peart, T. E.; Carron, J. M.; Tse, H. Chemical derivatization analysis of pesticide residues. Part XI. An improved method for the determination and confirmation of acidic herbicides in water. J. Assoc. Off. Anal. Chem. 1991, 74 (5), 835-842.
24. Polcaro, C. M.; Berti, A.; Mannina, L.; Marra, C.; Sinibaldi, M.; Viel, S. Chiral HPLC resolution of neutral pesticides. J. Liquid Chrom. Rel. Technol. 2004, 27 (1), 49-61.
25. PMRA (Pest Management Regulatory Agency). Reevaluation decision document, 2004, Mecoprop RRD2004-09; Pest Management Regulatory Agency: Ottawa, May 2004.