Biodegradation of the chlorophenoxy herbicide (R)-(+)-mecoprop by Alcaligenes denitrificans

Biodegradation

Volumn 8, Issue 1, 1997, Pages 43-52

  Tett, Vanessa A ^a   Willetts, Andrew J ^b   Lappin Scott, Hilary M ^b  

^a UNIVERSITY OF KENT   (United Kingdom)

^b UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

Alcaligenes denitrificans; Biodegradation; Chloroaromatic; Mecoprop (R) (+) 2(2 methyl 4 chlorophenoxy)propionic acid

Indexed keywords

ACHROMOBACTER DENITRIFICANS; ALCALIGENES; BACTERIA (MICROORGANISMS);

EID: 0030793688     PISSN: 09239820     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1008262901202     Document Type: Article

References (40)

1. Abbott MT & Udenfriend S (1974) α-Ketoglutarate-coupled dioxygenases. In: Hayaishi O (Ed) Molecular Mechanisms of Oxygen Activation (pp 167-214). Academic Press, London
2. Anonymous (1992) Produce Farmstat Survey
3. Bollag JM, Helling CS & Alexander M (1967) Metabolism of 4-chloro-2-methylphenoxyacetic acid by soil bacteria. Appl. Microbiol. 15: 1393-1398
4. _ (1968a) 2,4-D metabolism: enzymatic hydroxylation of chlorinated phenols. J. Agr. Food Chem. 16: 826-828
5. Bollag JM, Briggs GG, Dawson JE & Alexander M (1968b) 2,4-D metabolism: enzymatic degradation of chlorocatechols. J. Agr. Food Chem. 16: 829-833
6. Chaudhry GR & Chapalamadugu S (1991) Biodegradation of halogenated organic compounds. Microbiol. Rev. 55: 59-79
7. Commandeur LCM & Parsons JR (1990) Degradation of halogenated aromatic compounds. Biodegradation 1: 207-220
8. Dagley S (1987) Lessons from biodegradation. Annu. Rev. Microbiol. 41: 1-23
9. Evans WC, Smith BSW, Moss P & Fernley HN (1971a) Bacterial metabolism of 4-chlorophenoxyacetate. Biochem. J. 122: 509-517
10. Evans WC, Smith BSW, Fernley HN & Davies JI (1971b) Bacterial metabolism of 2,4-dichlorophenoxyacetate. Biochem. J. 122: 543-552
11. Fukumori F & Hausinger RP (1993) Alcaligenes eutrophus JMP134 '2,4-dichlorophenoxyacetate monooxygenase' is an α-ketoglutarate-dependent dioxygenase. J. Bacteriol. 175: 2083-2086
12. Gamar Y & Gaunt JK (1971) Bacterial metabolism of 4-chloro-2-methylphenoxyacetate (MCPA): formation of glyoxylate by side-chain cleavage. Biochem. J. 122: 527-531
13. Gaunt JK & Evans WC (1971a) Metabolism of 4-chloro-2-methylphenoxyacetate by a soil pseudomonad: Preliminary evidence for the metabolic pathway. Biochem. J. 122: 519-526
14. _ (1971b) Metabolism of 4-chloro-2-methylphenoxyacetate by a soil pseudomonad. Ring-fission, lactonizing and delactonizing enzymes. Biochem. J. 122: 533-542
15. Häggblom MM (1992) Microbial breakdown of halogenated aromatic pesticides and related compounds. FEMS Microbiol. Rev. 103: 29-72
16. Haigler BE, Nishino SF & Spain JC (1988) Degradation of 1, 2-dichlorobenzene by a Pseudomonas sp. Appl. Environ. Microbiol. 54: 294-300
17. Hegeman GD (1966) Synthesis of the enzymes of the mandelate pathway by Pseudomonas putida. J. Bacteriol. 91: 1140-1154
18. Higson FK & Focht DD (1992) Utilization of 3-chloro-2-methylbenzoic acid by Pseudomonas cepacia MB2 through the meta fission pathway. Appl. Environ. Microbiol. 58: 2501-2504
19. Kilby (1948) The bacterial oxidation of phenol to β-keto-adipic acid. Biochem. J. 43: V-VI
20. Kilpi S (1980) Degradation of some phenoxy acid herbicides by mixed cultures of bacteria from soil treated with 2-(2-methyl-4-chloro)phenoxypropionic acid. Microbial Ecol. 6: 261-270
21. Lindholm L, Backström V & Kilpi S (1982) Degradation of mecoprop in soil. Acta Agr. Scandinavica 32: 429-432
22. Loos MA, Roberts RN & Alexander M (1967a) Phenols as intermediates in the decomposition of phenoxyacetates by an Arthrobacter sp. Canadian J. Microbiol. 13: 679-690
23. _ (1967b) Formation of 2,4-dichlorophenol and 2,4-dichloroanisole from 2,4-dichlorophenoxyacetate by Arthrobacter sp. Canadian J. Microbiol. 13: 691-699
24. Loos MA (1975) Phenoxyalkanoic acids. In: Kearney PC & Kaufman DD (Eds) Herbicides: Their Chemistry, Degradation and Mode of Action, Vol 1 (pp 34-57). Marcel Dekker, New York
25. MacRae IC, Alexander M & Rovira AD (1963) The decomposition of 4-(2, 4-dichlorophenoxy)butyric acid by Flavobacterium sp. J. Gen. Microbiol. 32: 69-76
26. Oh K & Tuovinen OH (1991a) Bacterial degradation of phenoxy herbicide mixtures 2,4-D and MCPP. Bull. Environ. Contam. Toxicol. 47: 1-8
27. _ (1991b) Detection and identification of substituted phenols as intermediates of concurrent bacterial degradation of the phenoxy herbicides MCPP and 2,4-D. Microbiol. Lett. 79: 141-146
28. _ (1994) Biodegradation of the phenoxy herbicides MCPP and 2,4-D in fixed-film column reactors. Int. Biodet. Biodeg. 33: 93-99
29. Ornston LN & Stanier RY (1966) The conversion of catechol and protocatechuate to β-ketoadipate by Pseudomonasputida. J. Biol. Chem. 241: 3776-3785
30. Pandell AJ (1976) Enzyme-like aromatic oxidations. Metalcatalysed peracetic acid oxidation of phenol and catechol to cis, cis muconic acid. J. Org. Chem. 41: 3992-3996
31. Pieper DH, Stadlerfritzsche K, Engesser KH, Knackmuss HJ (1993) Metabolism of 2-chloro-4-methylphenoxyacetate by Alcaligenes eutrophus JMP-134. Arch. Microbiol. 160: 169-178
32. Sandmann E & Loos MA (1988) Aromatic metabolism of a 2,4-D degrading Arthrobacter sp. Canadian J. Microbiol. 34: 125-130
33. Schlömann M (1994) Evolution of chlorocatechol catabolic pathways. Biodegradation 5: 301-321
34. Sinton GL, Fan LT, Erickson LE & Lee SM (1986) Biodegradation of 2,4-D and related xenobiotic compounds. Enzyme Microbial Technol. 8: 395-403
35. Stanier RY, Palleroni NJ & Doudoroff M (1966) The aerobic pseudomonads: a taxonomic study. J. Gen. Microbiol. 43: 159-271
36. Tett VA, Willetts AJ & Lappin-Scott HM (1994) Enantioselective degradation of the herbicide mecoprop [2-(2-methyl-4-chlorophenoxy)propionic acid] by mixed and pure bacterial cultures. FEMS Microbiol. Ecol. 14: 191-200
37. Tiedje JM & Alexander M (1969) Enzymatic cleavage of the ether bond of 2,4-dichlorophenoxyacetate. J. Agr. Food Chem. 17: 1080-1084
38. Tiedje JM, Duxbury JM, Alexander M & Dawson JE (1969) 2,4-D metabolism: pathway of degradation of chlorocatechols by Arthrobacter sp. J. Agr. Food Chem. 17: 1021-1026
39. Worsey MJ & Williams PA (1975) Metabolism of toluene and xylenes by Pseudomonas putida (arvilla) mt-2: evidence for a new function of the TOL plasmid. J. Bacteriol. 124: 7-13
40. Worthing CR & Walker SB (1991) The Pesticide Manual: A World Compendium. BCPC Publications, Bracknell, UK