Plant and soil enantioselective biodegradation of racemic phenoxyalkanoic herbicides

Chirality

Volumn 11, Issue 4, 1999, Pages 330-337

  Schneiderheinze, J M ^a   Armstrong, D W ^a   Berthod, A ^a  

^a MISSOURI UNIVERSITY OF SCIENCE AND TECHNOLOGY   (United States)

Author keywords

Chirobiotic T; Column switching; Enantioselective chromatography; Kinetics; Teicoplanin

Indexed keywords

ALKOXYBENZENE DERIVATIVE; HERBICIDE; TEICOPLANIN;

ARTICLE; BIODEGRADATION; CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; CHIRALITY; EXTRACTION; GRASS; OPTICAL ROTATION; PRIORITY JOURNAL; RACEMIC MIXTURE; SOIL MICROFLORA; STEREOCHEMISTRY;

2,4-DICHLOROPHENOXYACETIC ACID; 2-METHYL-4-CHLOROPHENOXYACETIC ACID; BIODEGRADATION, ENVIRONMENTAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HERBICIDES; MOLECULAR STRUCTURE; PLANTAGO; PLANTS, MEDICINAL; POACEAE; SOIL; STEREOISOMERISM;

EID: 0032951332     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1999)11:4<330::AID-CHIR12>3.0.CO;2-G     Document Type: Article

References (29)

1. Armstrong DW, Reid GL III, Hilton ML, Chang C-D. Relevance of enantiomeric separations in environmental science. Environ Pollut 1993;79:51-58.
2. Ariëns EJ. Racemates - an impediment in the use of drugs and agrochemicals. In: Krstulovic AM, editor. Chiral separations by HPLC. Chichester: Ellis Horwood; 1989. p 31-68.
3. Sugavanam B. Diastereoisomers and enantiomers of paclobutrazol: their preparation and biological activity. Pestic Sci 1984;15:296-302.
4. DeCamp WH. The FDA perspective on the development of stereoisomers. Chirality 1989;1:2-6.
5. Mueller SR, Berg M, Ulrich MM. Atrazine and its primary metabolites in Swiss lakes: input characteristics and long-term behavior in the water column. Environ Sci Technol 1997;31:2104-2113.
6. Ohsaki Y, Matsueda T, Kurokawa Y. Distribution of polychlorinated dibenzo-p-dioxinz, polychlorinated dibenzofurans, and non-ortho polychlorinated biphenyls in river and offshore sediment. Environ Pollut 1997;96:79-88.
7. Brown LM, Blair A Gibson R, Everett GD, Cantor KP, Schuman LM, Burmeister LF, Van Lier SF, Dick F. Pesticide exposures and other atricultural risk factors for leukemia among men in Iowa and Minnesota USA. Cancer Res 1990;50:6585-6591.
8. Loos MA. Phenoxyalkanoic acids. In: Kearney PC, Kaufman DD, editors. Herbicides: chemistry, degradation, and mode of action. Vol. 1. New York: Marcel Dekker Inc., 1975. p 2-101.
9. Szmedra P. Banning 2,4-D and the phenoxy herbicides: potential economic impact Weed Sci 1997;45:592-598.
10. Aberg B. In: Wain RL, Wightman F, editors. The chemistry and mode of action of plant growth substances. London: Butterworth Scientific Publications; 1956. p 102.
11. Bollag J-M, Briggs GG, Dawson JE, Alexander M. 2,4-D metabolism. J Agric Food Chem 1968;16:829-832.
12. Feung C-S, Hamilton RH, Mumma RO. Metabolism of 2,4-dichlorophenoxy acid. V. Identification of metabolites in soybean callus tissue cultures. J Agric Food Chem 1973;21:637-640.
13. Feung C-S, Hamilton RH, Mumma RO. Metabolism of 2,4-dichlorophenoxy acid. VII. Comparison of metabolites from five species of plant callus tissue cultures. J Agric Food Chem 1975;23:373-376.
14. Bristol DW, Ghanuni AM, Oleson AE. Metabolism of 2,4-dichlorophenoxyacetic acid by wheat cell suspension cultures. J Agric Food Chem 1977;25:1308-1314.
15. Thompson DG, Stephenson GR, Solomon KR, Skepasts AV. Persistence of (2,4-dichlorophenoxy)acetic acid and 2-(2,4-dichlorophenoxy)-propionic acid in agricultural and forest soils of northern and southern Ontario. J Agric Food Chem 1984;32:578-581.
16. Tett VA, Willetts AJ, Lappin-Scott HM. Enantioselective degradation of the herbicide mecoprop [2-(2-methyl-4-chlorophenoxy) propionic acid] by mixed and pure bacterial cultures. Fed Eur Microbiol Soc Microbiol Ecol 1994;14:191-200.
17. Tett VA, Willetts AJ, Lappin-Scott HM. Biodegradation of the chlorophenoxy herbicide (R)-(+)-mecoprop by Alcaligenes denitrificans. Biodegradation 1997;8:43-52.
18. Bärenwald G, Schneider B, Schütte H-R. Metabolism of the herbicide 2-(2,4-dichlorophenoxy)-propionic acid (dichlorprop) in barley (Hordeum vulgare) Z Naturforsch 1987;42c:486-490.
19. Goedicke H-J, Banasiak U. Fate and metabolism of dichlorprop in cereals and field grass. Arch Environ Contam Toxicol 1988;17:81-85.
20. Bärenwald G, Schneider B, Schütte H-R. Comparative investigations on the metabolism of the herbicide 2-(2,4-dichlorophenoxy)-propionic acid in plants and cultured cells of tomato. Z Naturforsch 1989;44c: 233-236.
21. Faller J, Hühnerfuss H, König WA, Ludwig P. Do marine bacteria degrade α-BHC stereoselectively? Environ Sci Technol 1991;25:676-678.
22. Faller J, Hühnerfuss H, König WA, Ludwig P. Gas chromatographic separation of the enantiomers of marine organic pollutants: distribution of α-HCH in the North Sea. Mar Pollut Bull 1991;22:82-86.
23. Garrison AW, Schnitt P, Martens D, Kettrup A. Enantiomeric selectivity in the environmental degradation of dichlorprop as determined by high-performance capillary electrophoresis. Environ Sci Technol 1996; 30:2449-2455.
24. Ludwig P, Gunkel W, Hühnerfuss H. Chromatographic separation of the enantiomers of marine pollutants. Part 5: enantioselective degradation of phenoxycarboxylic acid herbicides by marine microorganisms. Chemosphere 1992;24:1423-1429.
25. Maples M, Kapila S, Armstrong DW. Enantioselective determination of pesticide residues in environmental matrices by dual column gas chromatography. J Chromatogr A 1998. Submitted.
26. Armstrong DW, Liu Y, Yu T. LC/GC 1998. Submitted.
27. Müller MD, 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.
28. Weber K, Kreuzig R, Bahadir M. On enantioselective separation of phenoxypropionates using permethylated β-cyclodextrin HPLC and GC columns. Chemosphere 1997;35:13-20.
29. [Anonymous]. FDA's policy statement for the development of new stereoisomeric drugs. Chirality 1992;4:338-340.