Comparison of concentrations and stereoisomer ratios of mecoprop, dichlorprop and metolachlor in Ontario streams, 2006-2007 vs. 2003-2004

Environmental Pollution

Volumn 158, Issue 5, 2010, Pages 1842-1849

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

^a ENVIRONMENT CANADA   (Canada)

Author keywords

Enantiomers; Herbicides; Ontario; Pesticides; Stereoisomers; Streamwater

Indexed keywords

ENANTIOMER FRACTIONS; ENANTIOSELECTIVE DEGRADATION; INTERCONVERSIONS; LAKE ONTARIO; LOW CONCENTRATIONS; MEDIAN CONCENTRATION; METOLACHLOR CONCENTRATIONS; METOLACHLORS; ONTARIO; ORDERS OF MAGNITUDE; STEREO-SELECTIVE; STEREOISOMERS; STREAM WATER;

CHIRALITY; DEGRADATION; ENANTIOMERS; HERBICIDES; HYDRAULICS; STEREOCHEMISTRY; WEED CONTROL;

CONCENTRATION (PROCESS);

DICHLORPROP; HERBICIDE; MECOPROP; METOLACHLOR; SURFACE WATER;

CONCENTRATION (COMPOSITION); HERBICIDE; PESTICIDE; STREAMWATER; WATER QUALITY;

ARTICLE; CANADA; CHEMICAL COMPOSITION; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; ENANTIOMER; LAKE; RACEMIC MIXTURE; STEREOCHEMISTRY; STEREOISOMERISM; STREAM (RIVER); WATER ANALYSIS; WATER QUALITY;

2,4-DICHLOROPHENOXYACETIC ACID; 2-METHYL-4-CHLOROPHENOXYACETIC ACID; ACETAMIDES; ENVIRONMENTAL MONITORING; HERBICIDES; ONTARIO; RIVERS; STEREOISOMERISM; WATER POLLUTANTS, CHEMICAL;

GREAT LAKES [NORTH AMERICA]; LAKE ONTARIO;

EID: 77950296299     PISSN: 02697491     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.envpol.2009.11.003     Document Type: Article

References (32)

1. Åberg B. In: Wain R.L., and Wightman F. (Eds). The Chemistry and Mode of Action of Plant Growth Substances (1956), Butterworth Scientific Publications, London 102
2. Aboul Eish M.Y.Z., and Wells M.J.M. Monitoring stereoselective degradation of metolachlor in a constructed wetland: use of statistically valid enantiomeric and diastereomeric fractions as opposed to ratios. J. Chromatogr. Sci. 46 (2008) 269-275
3. Blaser H.-U. The chiral switch of (S)-metolachlor: a personal account of an industrial odyssey in asymmetric catalysis. Adv. Synth. Catal. 344 (2002) 17-31
4. Brimble, S., Bacchus, P., Caux P.-Y., 2005. 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.
5. Buerge I.J., Poiger T., Müller M.D., and Buser H.-R. Enantioselective degradation of metalaxyl in soils: chiral preference changes with soil pH. Environ. Sci. Technol. 37 (2003) 2668-2674
6. Buser H.-R., Hany R., Müller M.D., Poiger T., and Rentsch D. Comment on the influence of the chemical environment on metolachlor conformations. J. Agric. Food Chem. 2000 48 (2000) 4448-4449
7. Buser H.-R., Poiger T., and 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. 34 (2000) 2690-2696
8. Buser H.-R., and Müller M.D. Environmental behavior of acetamide pesticide stereoisomers. 1. Stereo- and enantioselective determination using chiral high-resolution gas chromatography and chiral high-performance liquid chromatography. Environ. Sci. Technol. 29 (1995) 2023-2030
9. 2O/soil system. Environ. Sci. Technol. 31 (1997) 1960-1967
10. Buser H.-R., and Müller M.D. Occurrence and transformation reactions of chiral and achiral phenoxyalkanoic acid herbicides in lakes and rivers in Switzerland. Environ. Sci. Technol. 32 (1998) 626-633
11. Buser H.-R., Müller M.D., Poiger T., and Palmer M.E. Environmental behavior of the chiral acetamide pesticide metalaxyl: enantioselective degradation and chiral stability in soil. Environ. Sci. Technol. 36 (2002) 221-226
12. CCME (Canadian Council of Ministers of the Environment)., 1991. 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. [Updated and reprinted with minor revisions and editorial changes in Canadian environmental quality guidelines, Chapter 4, CCME, 1999, Winnipeg].
13. Garrison A.W., Schmitt P., and Kettrup A. Enantiomeric selectivity in the environmental degradation of dichlorprop as determined by high-performance capillary electrophoresis. Environ. Sci. Technol. 30 (1996) 2449-2455
14. Garrison A.W. Probing the enantioselectivity of chiral pesticides. Environ. Sci. Technol. 40 (2006) 16-23
15. Grabusky, J., Martin, P.A., Struger, J., 2004. Pesticides in Ontario: A critical assessment of potential toxicity of urban use products to wildlife, with consideration for endocrine disruption. Volume 3. Phenoxy herbicides, chlorothalonil and chlorpyrifos. Technical report series #410, Environment Canada, Canadian Wildlife Service, Environmental Conservation Branch, Ontario Region.
16. Hegeman W.J.M., and Laane R.W.P.M. Enantiomeric enrichment of chiral pesticides in the environment. Rev. Environ. Contam. Toxicol. 173 (2002) 85-116
17. Jayasundera S., Schmidt W., Hapeman C.J., and Torrents A. Influence of the chemical environment on metolachlor conformations. J. Agric. Food Chem. 47 (1999) 4435-4442
18. Jayasundera S., Schmidt W., Hapeman C.J., and Torrents A. Rebuttal on: influence of the chemical environment on metolachlor conformations. J. Agric. Food Chem. 48 (2000) 4450-4451 2000
19. Krause A., Hancoc W.G., Minard R.D., Freyer A.J., Honeycutt R.C., LeBaron H.M., Paulson D.L., Liu S.Y., and Bollag J.M. Microbial transformation of herbicide metolachlor by a soil actinomycete. J. Agric. Food Chem. 33 (1985) 584-589
20. Kurt-Karakus P.B., Bidleman T.F., Muir D.C.G., Cagampan S.J., Struger J., Sverko E., Small J.M., and Jantunen L.M. Chiral current-use herbicides in Ontario streams. Environ. Sci. Technol. 42 (2008) 8452-8458
21. Liu S.Y., Freyer A.J., and Bollag J.M. Microbial dechlorination of the herbicide metolachlor. J. Agric. Food Chem. 39 (1991) 631-636
22. Loos M.A. Phenoxyalkanoic acids. In: Kearney P.C., and Kaufman D.D. (Eds). Herbicides: Chemistry, Degradation and Mode of Action vol. 1 (1975), Marcel Dekker Inc., New York 2-101
23. McGahen L.L., and Tiedje J.M. Metabolism of two new acylanilide herbicides, Antor herbicide (H-22234) and Dual (metolachlor) by the soil fungus Chaetomium globosum. J. Agric. Food Chem. 26 (1978) 414-419
24. McGee B., Berges H., and Callow K. Survey of Pesticide Use in Ontario, 2003. Estimates of Pesticides Used on Field Crops, Fruit and Vegetable Crops, and Other Agricultural Crops (2004), Ontario Ministry of Agriculture and Food, Guelph, ON. 0-7743-9959-7
25. Monkiedje A., Zuehlke S., Maniepi S.J.N., and Spiteller M. Elimination of racemic and enantioenriched metalaxyl based fungicides under tropical conditions in the field. Chemosphere 69 (2007) 655-663
26. Müller M.D., and Buser H.-R. Environmental behavior of acetamide pesticide stereoisomers. 2. Stereo- and enantioselective degradation in sewage sludge and soil. Environ. Sci. Technol. 29 (1995) 2031-2037
27. Müller M.D., and 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. 31 (1997) 1953-1959
28. Nickel K., Suter M.J.-F., and Kohler H.-P.E. Involvement of two alpha-keto-glutarate dependent dioxygenases in enantioselective degradation of (R)- and (S)-mecoprop by Sphingomonas herbicidovorans MH.J. Bacteriol 179 (1997) 6674-6679
29. PMRA (Pest Management Regulatory Agency). Reevaluation Decision Document. Mecoprop RRD2004-09 (May 2004), Pest Management Regulatory Agency, Ottawa
30. Polcaro C.M., Berti A., Mannina L., Marra C., Sinibaldi M., and Viel S. Chiral HPLC resolution of neutral pesticides. J. Liquid Chrom. Relat. Tech. 27 (2004) 49-61
31. Saxena A., Zhang R., and Bollag J.M. Microorganisms capable of metabolizing the herbicide metolachlor. Appl. Environ. Microbiol. 53 (1987) 390-396
32. Zipper C., Bolliger C., Fleischmann T., Suter M.J.-F., Angst W., Müller M.D., and Kohler H.-P.E. Fate of the herbicide mecoprop, dichlorprop and 2,4-D in aerobic and anaerobic sewage sludge as determined by laboratory batch studies and enantiomer-specific analysis. Biodegradation 10 (1999) 271-278