Bacterial Desulfonation of the Ethanesulfonate Metabolite of the Chloroacetanilide Herbicide Metazachlor

Abstract

Metazachlor (R-CH 2 -Cl), a chloroacetanilide herbicide, is converted in soil to products including the ethanesulfonate metabolite (R-CH 2 -SO 3 -; BH 479-8). Nothing is known about the degradation of the ethanesulfonates of this class of herbicides. We used inocula derived from five sources for enrichment cultures to utilize R-CH 2 -SO 3 -as a sole sulfur source for the growth of microorganisms. Each culture yielded bacteria that caused the disappearance of R-CH 2 -SO 3 -and the formation of a product identified as the glycolate metabolite (R-CH 2 -OH; BH 479-1) by mass spectrometry. A pure culture, strain HL1, was isolated, and this bacterium quantitatively desulfonated R-CH 2 -SO 3 -, the sulfur being recovered in cell protein. Recovery of the organic moiety was usually about 80%. A second ethanesulfonate (R′-CH 2 -SO 3 -) and two alkylsulfonates, but not taurine, were utilized by strain HL1 as sulfur sources.

Bioavailability of water-polluting sulfonoaromatic compounds

“…Glassware was cleaned thoroughly and care taken to exclude extraneous sulfur (e.g. Laue et al 1996).…”

“…Substrates and products were determined by isocratic reversedphase high-pressure liquid chromatography (HPLC) (Laue et al 1996) or by ion-pair chromatography (Lange et al 1995) as indicated in the text; the apparatus included a diode array detector. Chromatograms were initially evaluated with wavelength settings of 215 nm for benzenesulfonates, 230 nm for the naphthalenedisulfonates, and 245 nm for the amino-naphthalenedisulfonates.…”

Thiosulfate as a metabolic product: the bacterial fermentation of taurine

“…Ammonia was determined and tentatively identified by the Berthelot reaction (Gesellschaft Deutscher Chemiker 1996), and the identity was confirmed in the specific reaction of glutamate dehydrogenase (Bergmeyer 1983). Thiosulfate was routinely determined by ion chromatography (Laue et al 1996) and tentatively identified by cochromatography; the identification was confirmed titrimetrically and turbidimetrically (Gesellschaft Deutscher Chemiker 1996). Sulfite and sulfate were determined by ion chromatography (Laue et al 1996).…”

“…Thiosulfate was routinely determined by ion chromatography (Laue et al 1996) and tentatively identified by cochromatography; the identification was confirmed titrimetrically and turbidimetrically (Gesellschaft Deutscher Chemiker 1996). Sulfite and sulfate were determined by ion chromatography (Laue et al 1996). Sulfide was determined colorimetrically (Cline 1969).…”

Assimilation of sulfur from alkyl- and arylsulfonates by Clostridium spp.

“…The aromatic sulfonates and their derivatives were determined by reversed-phase HPLC with diode array detection as described elsewhere (Laue et al 1996). 5-Bromo-4-chloro-3-indolyl-sulfate (Xsulfate) and 2,6-naphthyldisulfonate were assayed by ion-pair chromatography (Lange et al 1995).…”