The degradation of diflubenzuron and its chief metabolites in soils. Part III. Fate of 2,6‐difluorobenzoic acid

Nimmo, W. B.; Joustra, Kees D.; Willems, A. G. M.

doi:10.1002/ps.2780290106

Cited by 12 publications

(6 citation statements)

References 7 publications

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“…Additionally, III proved to be very stable, in this study, under anaerobic soil conditions, with no observed loss after 2 months of incubation. This contrasts with the results reported by Nimmo et al [27], who reported half-lives of less than 12 d for two soils under aerobic conditions. Our results indicate that III would be persistent in the aqueous environment.…”

Section: Laboratory Experimentscontrasting

confidence: 99%

Fate and disposition of diflubenzuron in rice fields

Mabury

Crosby

1996

Enviro Toxic and Chemistry

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Laboratory and field investigations were undertaken to determine the fate, disposition, and persistence of the insecticide diflubenzuron in California rice culture. Water solubility was similar in distilled/deionized water (88.8 ± 4.0 μg/L) and rice field water (92.6 ± 3.5 μg/L), while the measured Henry's law constant was 2.34 ± 0.02 × 10−1 Pa.m3/mole. Diflubenzuron was rapidly photodegraded in field water primarily to the more stable chlorophenylurea and difluorobenzoic acid; field water photolysate was equally toxic to Daphnia magna as pure insecticide solutions. Applications to experimental rice field plots resulted in rapid dissipation of diflubenzuron (half‐life 27.3 h), nonpersistent sediment residues, and significant partitioning into the surface microlayer.

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Section: Laboratory Experimentscontrasting

confidence: 99%

Fate and disposition of diflubenzuron in rice fields

Mabury

Crosby

1996

Enviro Toxic and Chemistry

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“…The fluorine substituent can thus either be removed during initial dioxygenation or during lactone formation after cleavage of the aromatic ring. Degradation of more highly fluorinated benzoates has not been studied in detail, but 2,6-difluorobenzoate, a metabolite of the insecticide diflubenzuron was found to be mineralized to CO 2 in soil [225].…”

Section: Aerobic Degradation Of Halobenzoatesmentioning

confidence: 99%

“…Diflubenzuron (1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea) was hydrolysed in soil to 4-chlorophenylurea and 2,6-difluorobenzoate [314]. 4-Chlorophenylurea was presumably converted to 4-chloroaniline and bound to soil [315], while 2,6-difluorobenzoate mineralized to CO 2 [225]. The formation of halogenated anilines by hydrolysis of halogenated acylanilides, phenylcarbamates, and phenylureas is exemplified with the herbicides propanil, linuron and chlorpropham in Fig.…”

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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“…2,6-Difluorobenzoic acid, which is a metabolite formed from fluorinated pesticides (Nimmo et al 1984;Finkelstein et al 2001), was transformed in soil as shown by a release of 14 CO 2 from 2,6-difluorobenzoic acid with a 14 C label at the C-1 position (Nimmo et al 1990). However, no information on the extent of defluorination was given.…”

Section: Polyfluorinated Compoundsmentioning

confidence: 99%

The biodegradation vs. biotransformation of fluorosubstituted aromatics

Kiel

Engesser

2015

Appl Microbiol Biotechnol

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Fluoroaromatics are widely and--in recent years--increasingly used as agrochemicals, starting materials for chemical syntheses and especially pharmaceuticals. This originates from the special properties the carbon-fluorine bond is imposing on organic molecules. Hence, fluoro-substituted compounds more and more are considered to be important potential environmental contaminants. On the other hand, the microbial potentials for their transformation and mineralization have received less attention in comparison to other haloaromatics. Due to the high electronegativity of the fluorine atom, its small size, and the extraordinary strength of the C-F bond, enzymes and mechanisms known to facilitate the degradation of chloro- or bromoarenes are not necessarily equally active with fluoroaromatics. Here, we review the literature on the microbial degradation of ring and side-chain fluorinated aromatic compounds under aerobic and anaerobic conditions, with particular emphasis being placed on the mechanisms of defluorination reactions.

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The degradation of diflubenzuron and its chief metabolites in soils. Part III. Fate of 2,6‐difluorobenzoic acid

Cited by 12 publications

References 7 publications

Fate and disposition of diflubenzuron in rice fields

Fate and disposition of diflubenzuron in rice fields

Microbial breakdown of halogenated aromatic pesticides and related compounds

The biodegradation vs. biotransformation of fluorosubstituted aromatics

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