The degradation of diflubenzuron and its chief metabolites in soils. Part I: Hydrolytic cleavage of diflubenzuron

Nimmo, W. B.; Wilde, Pieter C. De; Verloop, A.

doi:10.1002/ps.2780150608

Cited by 24 publications

(11 citation statements)

References 9 publications

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“…Diflubenzuron showed only limited aqueous solubility; at 20ЊC the solubility in Milli-Q water was 88.8 Ϯ 4.0 g/L (n ϭ 6) and in filtered field water was 92.6 Ϯ 3.5 g/L (n ϭ 4). These results indicate that the water solubility of DFB is lower than the manufacturer's literature values and those of other researchers [17,18,19]. The method using a generator column is generally considered the most reliable for the accurate determination of water solubilities [20].…”

Section: Laboratory Experimentsmentioning

confidence: 66%

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 Experimentsmentioning

confidence: 66%

Fate and disposition of diflubenzuron in rice fields

Mabury

Crosby

1996

Enviro Toxic and Chemistry

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“…Following its initial synthesis in 1972, the environmental fate and breakdown of diflubenzuron has been extensively studied 4–11. In water, its half‐life is typically less than 8 days, with hydrolysis fastest at increased temperatures, pH and sediment contents 3.…”

Section: Introductionmentioning

confidence: 99%

Aqueous solubilities, photolysis rates and partition coefficients of benzoylphenylurea insecticides

Marsella¹,

Jaskolka²,

Mabury³

2000

Pest Manag. Sci.

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The aqueous solubilities and octanol±water partition coef®cients (K OW ) of the benzoylphenylurea (BPU) insecticides te¯ubenzuron, chlor¯uazuron,¯ufenoxuron and hexa¯umuron were determined in comparison with the more extensively studied di¯ubenzuron. Both te¯ubenzuron and hexa¯umuron were substantially less water-soluble (9.4 (AE 0.3) mg litre À1 and 16.2 (AE 0.5) mg litre À1 in water, respectively) than the value previously reported for di¯ubenzuron (89 (AE 4) mg litre À1 in water). Log K OW values for di¯ubenzuron, te¯ubenzuron, hexa¯umuron,¯ufenoxuron and chlor¯uazuron were 3.8, 5.4, 5.4, 6.2 and 6.6, respectively, as determined using reverse-phase HPLC. Photodegradation of hexa¯umuron, te¯ubenzuron and di¯ubenzuron in water indicated hexa¯umuron to be the most rapidly degraded of the three compounds at pH 7.0 (t 1/2 =8.6 (AE 0.4) h) and pH 9.0 (t 1/2 = 5 (AE 1) h); di¯ubenzuron was the slowest of the three pesticides to degrade in pH 7.0 (17 (AE 4) h) and pH 9.0 (8 (AE 2) h) buffered water. In a solar simulator using river water buffered to pH 9.0, te¯ubenzuron, hexa¯umuron and di¯ubenzuron half-lives were 20 (AE 4), 15 (AE 2) and 12 (AE 1) h, respectively; dark controls showed no loss of parent BPU over similar time periods.

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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%

“…Within 4 weeks, cleavage of the aromatic rings had occurred in 28 % of the diflubenzuron supplied, as indicated by a release of 14 CO 2 from substrate 14 C-labeled at both the fluorinated and chlorinated aromatic rings. The larger part of 14 CO 2 formation originated from the difluorophenyl ring (Nimmo et al 1984).…”

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 I: Hydrolytic cleavage of diflubenzuron

Cited by 24 publications

References 9 publications

Fate and disposition of diflubenzuron in rice fields

Fate and disposition of diflubenzuron in rice fields

Aqueous solubilities, photolysis rates and partition coefficients of benzoylphenylurea insecticides

The biodegradation vs. biotransformation of fluorosubstituted aromatics

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