Microbial Degradation of Isopropyl-N-3-Chlorophenylcarbamate and 2-Chloroethyl-N-3-Chlorophenylcarbamate

Kaufman, Donald D.; Kearney, Philip C.

doi:10.1128/aem.13.3.443-446.1965

Cited by 72 publications

(21 citation statements)

References 10 publications

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“…Hydrolysis of the herbicide Swep (methyl-N-(3,4-dichlorophenyl)-carbamate) to 3,4-dichloroaniline was observed in soil [305]. Several bacterial strains were isolated by Kaufman and Kearney [306] that degraded the herbicides isopropyl-N-3-chlorophenylcarbamate (chioropropham, CIPC) and 2-chloroethyl-N-3chlorophenylcarbamate (CEPC) with formation of 3-chloroaniline.…”

Section: Hydrolysis Of Phenylamidesmentioning

confidence: 99%

Microbial breakdown of halogenated aromatic pesticides and related compounds

Häggblom

1992

FEMS Microbiology Letters

363

132

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Considerable progress has been made in the last few years in understanding the mechanisms of microbial degradation of halogenated aromatic compounds. Much is already known about the degradation mechanisms under aerobic conditions, and metabolism under anaerobiosis has lately received increasing attention. The removal of the halogen substituent is a key step in degradation of halogenated aromatics. This may occur as an initial step via reductive, hydrolytic or oxygenolytic mechanisms, or after cleavage of the aromatic ring at a later stage of metabolism. In addition to degradation, several biotransformation reactions, such as methylation and polymerization, may take place and produce more toxic or recalcitrant metabolites. Studies with pure bacterial and fungal cultures have given detailed information on the biodegradation pathways of several halogenated aromatic compounds. Several of the key enzymes have been purified or studied in cell extracts, and there is an increasing understanding of the organization and regulation of the genes involved in haloaromatic degradation. This review will focus on the biodegradation and biotransformation pathways that have been established for halogenated phenols, phenoxyalkanoic acids, benzoic acids, benzenes, anilines and structurally related halogenated aromatic pesticides. There is a growing interest in developing microbiological methods for clean‐up of soil and water contaminated with halogenated aromatic compounds.

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Section: Hydrolysis Of Phenylamidesmentioning

confidence: 99%

Microbial breakdown of halogenated aromatic pesticides and related compounds

Häggblom

1992

FEMS Microbiology Letters

363

132

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“…Because of its resistance to hydrolysis and oxidation, bacterial degradation is the dominant elimination pathway in the environment (Wolfe et al 1978). It leads to the formation of the toxic intermediate 3-chloroaniline which can be mineralized further (Kaufman and Kearney 1965).…”

Section: Introductionmentioning

confidence: 99%

Spatial heterogeneity in degradation characteristics and microbial community composition of pesticide biopurification systems

et al. 2015

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“…Adaptation by soil micro-organisms to herbicides such tbat subsequent applicatioas are degraded more rapidly has been demonstrated for various pbenoxyalkanoic compounds (Audus, 1951;Brownbridge, 1956;Walker, 1957;Kirkland & Fryer, 1966;Kirkland, 1967), for endotbal (Horowitz, 1966), for aminotriazole (Riepma, 1962), for dalapon (Tbiegs, 1955;Leasure, 1964) and for chlorpropham (Kaufman & Kearney, 1965). Audus (1951) and Brownbridge (1956) (see Audus, 1964), have demonstrated that such enriched soils with enhanced capacity to degrade a particular phenoxy herbicide may also show increased activity against related compounds.…”

Section: Introductionmentioning

confidence: 99%

Degradation of Several Herbicides in a Soil Previously Treated With McPa

Kirkland

Fryer

1972

Weed Research

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Summary. Soil which had received nine previous field treatments of MGPA (33 kg/ha) at intervals of about 6 months, and which had become able to detoxify MCPA more rapidly than untreated control soil, was able to degrade MCPB with equal facility. In contrast, the disappearance rates of phytotoxic residues of dichlorprop (2‐(2,4‐dichloro‐phenoxy)propionic acid), mecoprop (2‐(4‐chloro‐2‐methylphenoxy)propionic acid), fenoprop (2‐(2,4,5‐trichlorophcnoxy)propionic acid) and dicamba (2‐methoxy‐3,6‐dichlorobcnzoic acid), as determined with a bioassay technique, were unaffected by previous treatments of the soil with MCPA. Indirect evidence from these studies suggests that β‐oxidation of MCPB to MCPA did not occur to any significant extent either in the soil to which the roots of the indicator plant were exposed or in the roots themselves. Dégradation de quelques herbicides dans un sol préddenvnent traté avec le MCPA Résumé. Un sol ayant reçu 9 traitements au MGPA (3,3 kg/ha) à des intervalles d'environ 6 mois et qui est devenu capable de dégrader le MCPA plus rapidement qu'un téntoin non traité, s'est montré capable de diégrader le MGPB avec la mêmefacilité. En revanehe, les taux de disparition de résidus toxiques déterminés par des testsbiologiques, du dichlorprop (acide 2‐(2,4‐dichlorophenoxy)propionique), du mécoprop(acide 2‐(4‐chloro‐2‐méthylphénoxy)propionique), du fénoprop (acide 2‐(2,4,5‐trichlorophénoxy)propionique) et du dicamba (acide 2‐méthoxy‐3,6‐dichlorobenzoique) n'ont pas été affectés par les traitements antérieurs avec le MCPA. Comme conclusion indirecte de ces travaux il est suggéré que la β‐oxydation du MGPB en MCPA ne se produit pas à un dcgré significatif dans le sol où les racines desplantes servant d'indicateurs sont plongées, pas plus que dans les racincs elles‐mêmes. Abbau von verschiedenen Herbiziden in einem vorher mit MCPA behandelten Boden Zusammenfassung. Boden, der auf dem Feld in Abstanden von sechs Monaten neunmal mit MGPA (3,3 kg/ha) behandelt wurde und dadurch in der Lage war, MGPA schneiler umzuwandeln als der unbchandelte Kon troll boden, konnte MCPB gleichermassen abbauen. Mit Hilfe von Biotests wurde ermittelt, dass vorausgehende Behandlungen des Bodens mit MCPA dagegen keinen Einfiuss auf die Abbaurate phytotoxischer Rückstände von Dichlorprop (2‐(2,4‐Dichlor‐phenoxy)‐propionsäurc), Mecoprop(2‐(4‐Ghlor‐2‐methyl‐phenoxy)‐propionsäure), Fenoprop (2‐(2,4,5‐Trichlorphenoxy)‐propionsaure) und Dicamba (3,6‐Dichlor‐2‐methoxy‐benzoesaure) hatten. Die Ergebnisse lassen darauf schliessen, dass der β‐Oxidation von MCPB zu MGPA weder im Boden, dem die Wurzein der Testpflanzen ausgesetzt waren, noch in den Wurzeln selbst Bedeutung zukam.

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Microbial Degradation of Isopropyl-N-3-Chlorophenylcarbamate and 2-Chloroethyl-N-3-Chlorophenylcarbamate

Cited by 72 publications

References 10 publications

Microbial breakdown of halogenated aromatic pesticides and related compounds

Microbial breakdown of halogenated aromatic pesticides and related compounds

Spatial heterogeneity in degradation characteristics and microbial community composition of pesticide biopurification systems

Degradation of Several Herbicides in a Soil Previously Treated With McPa

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