Summary
B. sphaericus is degrading the acylamides monalide, carboxin, oxycarboxin, 2,5-dimethylfurancarboxylic acid anilide, pyracarbolid, 2-methyl-and 2-chloro-benzoic acid anilide, the N′-phenylcarbamate propham and the N′-methoxyphenylurea compounds monolinuron, linuron, metabromuron and maloran by cleaving the amide linkage, forming the corresponding anilines and acids.
The metabolites were determined qualitatively by the means of co-thinlayer- and co-gaschromatography.
A pathway for degradation of the phenylamides by B. sphaericus is proposed.
Zusammenfassung
Die Acylanilide Monalide, Carboxin, Oxycarboxin, 2,5-Dimethylfurancarbonsäureanilid, Pyracarbolid, 2-Methyl- und 2-Chlorbenzoesäureanilid, der N′-Phenylcarbaminsäureester Propham und die N-Phenylharnstoff-derivate Monolinuron, Linuron, Metobromuron und Maloran wurden durch B. sphaericus an der Amidbindung zu den entsprechenden Anilinen und Säuren gespalten.
Der qualitative Nachweis der Zwischenprodukte gelang dünnschicht- und gaschromatographisch mit Hilfe von Vergleichssubstanzen.
Für den Abbau der Phenylamide durch B. sphaericus wurde ein Abbauschema aufgestellt.
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Literatur
Bartha, R.: Biochemical transformations of anilide herbicides in soil. J. Agr. Food Chem. 16, 602–604 (1968).
Bartha, R.: Transformation of solan in soil. Weed Science 17, 471–472 (1969).
—, Pramer, D.: Metabolism of acylanilide herbicides Advanc. appl. Microbiol. 13, 317–341 (1970).
Börner, H., Burgemeister, H., Schroeder, M.: Untersuchungen über Aufnahme, Verteilung und Abbau von Harnstoffherbiziden durch Kulturpflanzen, Unkräuter und Mikroorganismen. Z. Pfl. Krankh., Pfl. Path., Pfl. Schutz 76, 385–395 (1969).
Engelhardt, G., Wallnöfer, P. R., Plapp, R.: Degradation of linuron and some other herbicides and fungicides by a linuron-inducible enzyme from Bacillus sphaericus. Appl. Microbiol. (in press).
Geissbühler, H., Haselbach, C., Aebi, H., Ebner, L.: The fate of N′-(4-chlorophenoxy)-phenyl-N,N-dimethylurea (C1983) in soils and plants. III. Breakdown in soils and plants. Weed Res. 3, 227–297 (1963).
Goldman, P., Milne, G. W. A., Pignataro, M. T.: Fluorine-containing metabolites formed from 2-fluorobenzoic acid by Pseudomonas sp. Arch. Biochem. 118, 178–184 (1967).
Kearney, P. C.: Purification and properties of an enzyme responsible for hydrolyzing phenylcarbamates. J. Agr. Food Chem. 13, 561–564 (1965).
Lanzilotta, R. P., Pramer, D.: Herbicide transformation. I. Studies with whole cells of Fusarium solani. Appl Microbiol. 19, 301–306 (1970).
Schmeling, B. von, Kulka, M.: Systemic fungicidal activity of 1,4 oxathiin-derivatives. Science 152, 659–660 (1966).
Sharabi, N. E., Bordeleau, L. M.: Biochemical decomposition of the herbicide N-(3,4-dichlorophenyl)-2-methylpentanamide and related compounds. Appl. Microbiol. 18, 369–375 (1969).
Tweedy, B. G., Loeppky, C., Ross, J. A.: Metabolism of 3-(p-bromophenyl)-1-methoxy-1-methylurea (metobromuron) by selected soil microorganisms. J. Agr. Food Chem. 18, 851–853 (1970).
Walker, N., Harris, D.: Aniline utilization by a soil Pseudomonas. J. appl. Bact. 32, 457–462 (1969).
— Metabolism of 3-chlorobenzoic acid by Azotobacter species. Soil Biol. Biochem. 2, 27–32 (1970).
Wallnöfer, P.: The decomposition of urea herbicides by Bacillus sphaericus, isolated from soil. Weed Res. 9, 333–339 (1969).
—, Bader, J.: Degradation of urea herbicides by Bacillus sphaericus cellfree extract. Appl. Microbiol. 19, 714–717 (1970).
Wallnöfer, P., Königer, M., Safe, S., Hutzinger, O.: Metabolism of the systemic fungicide 2,5-dimethyl-3-furancarboxylic acid anilide BAS 3191 by Rhizopus japonicus and related fungi. J. Agr. Food Chem. (in press).
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Wallnöfer, P., Engelhardt, G. Der Abbau von Phenylamiden durch Bacillus sphaericus . Archiv. Mikrobiol. 80, 315–323 (1971). https://doi.org/10.1007/BF00406219
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DOI: https://doi.org/10.1007/BF00406219