Microbial degradation of several acetamide, acylanilide, carbamate, toluidine and urea pesticides

Kaufman, Donald D.; Blake, J. P.

doi:10.1016/0038-0717(73)90077-1

Cited by 88 publications

(38 citation statements)

References 17 publications

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“…For incubation experiments, mycelium from an agar plate (1 cm 2 ) was transferred to a 500-ml Erlenmeyer flask with 100 ml of Sabouraud glucose broth containing 40 g of D-glucose and 10 g of peptone of casein (Merck) per liter. After growth for 72 h at 30°C and 180 rpm on a rotary shaker, 5 ml of homogenized mycelium (homogenized three times for 2 s each time at 3,000 U/min in an IKA UltraTurrax homogenizer [Janke & Kunkel, Stauffen, Germany]) was used to inoculate 500-ml shake flasks containing 100 ml of a mineral salts medium (MM) (20) and 1 g of D-glucose as a carbon source. The slurry was cultivated as before for another 72 h. Glucose-grown cells were harvested by centrifugation (at 6000 ϫ g for 5 min) and washed twice with sterile MM.…”

Section: Methodsmentioning

confidence: 99%

Biotransformation of Biphenyl by Paecilomyces lilacinus and Characterization of Ring Cleavage Products

Gesell

Hammer

Specht

et al. 2001

Appl Environ Microbiol

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We examined the pathway by which the fungicide biphenyl is metabolized in the imperfect fungus Paecilomyces lilacinus. The initial oxidation yielded the three monohydroxylated biphenyls. Further hydroxylation occurred on the first and the second aromatic ring systems, resulting in the formation of five di-and trihydroxylated metabolites. The fungus could cleave the aromatic structures, resulting in the transformation of biphenyl via ortho-substituted dihydroxybiphenyl to six-ring fission products. All compounds were characterized by gas chromatography-mass spectroscopy and proton nuclear magnetic resonance spectroscopy. These compounds include 2-hydroxy-4-phenylmuconic acid and 2-hydroxy-4-(4-hydroxyphenyl)-muconic acid, which were produced from 3,4-dihydroxybiphenyl and further transformed to the corresponding lactones 4-phenyl-2-pyrone-6-carboxylic acid and 4-(4-hydroxyphenyl)-2-pyrone-6-carboxylic acid, which accumulated in large amounts. Two additional ring cleavage products were identified as (5-oxo-3-phenyl-2,5-dihydrofuran-2-yl)-acetic acid and [5-oxo-3-(4-hydroxyphenyl)-2,5-dihydrofuran-2-yl]-acetic acid. We found that P. lilacinus has a high transformation capacity for biphenyl, which could explain this organism's tolerance to this fungicide.

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Section: Methodsmentioning

confidence: 99%

Biotransformation of Biphenyl by Paecilomyces lilacinus and Characterization of Ring Cleavage Products

Gesell

Hammer

Specht

et al. 2001

Appl Environ Microbiol

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“…The technique used was similar to that of Snyder and Godfrey (1961). Each Warburg flask held about 30 mg dry wt of mycelium in 4 ml of Kaufman nutrient solution (Kaufman and Blake, 1973) and 50 mg/1 paraquat or diquat containing i /^iCi (2.2 x 10^ d.p.m.) of labelled herbicide with 0.3 ml 6 N H2SO4 in the side arm.…”

Section: Release Of ^^Cojf^om Diquat and Paraquatmentioning

confidence: 99%

The Breakdown of Paraquat and Diquat by Soil Fungi

Smith¹,

Lyon²,

Sahid³

1976

New Phytologist

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SUMMARYMucor hiemalis, Zygorhynchus heterogamous, Aspergillus niger and Penicillium frequentans were incubated in media containing either [methyl-^''^C] paraquat or [ethylene-^'^C] diquat. Aspergillus niger liberated ^''^002 from both herbicides and Penicillium frequentans only from paraquat. Mucor hiemalis and Zygorhynchus heterogamous were unable to release ^''^C02 from either. Those species able to degrade paraquat or diquat have correspondingly low intracellular levels of the herbicides and are able to tolerate high concentrations in the medium. By contrast, species unable to break them down are characterized by high intracellular levels and by their inability to grow at low concentrations. Tolerance to these herbicides appears to be the result of an ability to degrade them.

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“…Chloroanilines are widely used in the production of dyes, drugs and herbicides (Kearney & Kaufmann, 1969Latorre et al, 1984), and are also common metabolites of the microbial degradation of various phenylurea, acylanilide and phenylcarbamate herbicides (Bartha, 1968;Bartha & Pramer, 1970;Kaufman & Blake, 1973;Wallnofer, 1969). Environmental problems may arise from rather high concentrations of free chloroanilines as critical components of industrial effluents; these are generated by co-metabolic transformations, e.g.…”

Section: Introductionmentioning

confidence: 99%

Characterization of a soil-derived bacterial consortium degrading 4-chloroaniline

2003

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A bacterial consortium comprising four different species was isolated from an Indonesian agricultural soil using a mixture of aniline and 4-chloroaniline (4CA) as principal carbon sources. The four species were identified as Chryseobacterium indologenes SB1, Comamonas testosteroni SB2, Pseudomonas corrugata SB4 and Stenotrophomonas maltophilia SB5. Growth studies on aniline and 4CA as single and mixed substrates demonstrated that the bacteria preferred to grow on and utilize aniline rather than 4CA, although both compounds were eventually depleted from the culture supernatant. However, despite 100 % disappearance of the parent substrates, the degradation of 4CA was always characterized by incomplete dechlorination and 4-chlorocatechol accumulation. This result suggests that further degradation of 4-chlorocatechol may be the rate-limiting step in the metabolism of 4CA by the bacterial consortium. HPLC-UV analysis showed that 4-chlorocatechol was further degraded via an ortho-cleavage pathway by the bacterial consortium. This hypothesis was supported by the results from enzyme assays of the crude cell extract of the consortium revealing catechol 1,2-dioxygenase activity which converted catechol and 4-chlorocatechol to cis,cis-muconic acid and 3-chloro-cis,cis-muconic acid respectively. However, the enzyme had a much higher conversion rate for catechol [156 U (g protein)], indicating preference for non-chlorinated substrates. Members of the bacterial consortium were also characterized individually. All isolates were able to assimilate aniline. P. corrugata SB4 was able to grow on 4CA solely, while S. maltophilia SB5 was able to grow on 4-chlorocatechol. These results suggest that the degradation of 4CA in the presence of aniline by the bacterial consortium was a result of interspecies interactions.

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Microbial degradation of several acetamide, acylanilide, carbamate, toluidine and urea pesticides

Cited by 88 publications

References 17 publications

Biotransformation of Biphenyl by Paecilomyces lilacinus and Characterization of Ring Cleavage Products

Biotransformation of Biphenyl by Paecilomyces lilacinus and Characterization of Ring Cleavage Products

The Breakdown of Paraquat and Diquat by Soil Fungi

Characterization of a soil-derived bacterial consortium degrading 4-chloroaniline

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