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Buerge I.J.,Swiss Federal Research Station Agroscope | Muller M.D.,Swiss Federal Research Station Agroscope | Poiger T.,Swiss Federal Research Station Agroscope
Environmental Science and Technology | Year: 2013

Beflubutamid is a chiral soil herbicide currently marketed as racemate against dicotyledonous weeds in cereals. Biotests have shown that (-)-beflubutamid is at least 1000× more active than (+)-beflubutamid. Potential substitution of the racemate by (-)-beflubutamid should therefore be further considered. Here, we investigated the degradation behavior in soils and formation and degradation of two chiral metabolites. Laboratory incubation experiments were performed with an alkaline and an acidic soil. The compounds were analyzed by enantioselective GC-MS. Degradation rate constants were determined by kinetic modeling. In the alkaline soil, degradation of beflubutamid was slightly enantioselective, with slower degradation of the herbicidally active (-)-enantiomer. In the acidic soil, however, both enantiomers were degraded at similar rates. In contrast, degradation of a phenoxybutanamide metabolite was highly enantioselective. Chiral stability of beflubutamid and its metabolites was studied in separate incubations with the pure enantiomers in the same soils. In these experiments, (-)-beflubutamid was not converted to the nonactive (+)-enantiomer and vice versa. Significant enantiomerization was, however, observed for the major metabolite, a phenoxybutanoic acid. With regard to biological activity and behavior in soils, enantiopure (-)-beflubutamid definitively has the potential to substitute for the racemic herbicide. © 2012 American Chemical Society. Source


Buerge I.J.,Swiss Federal Research Station Agroscope | Keller M.,Swiss Federal Research Station Agroscope | Buser H.-R.,Swiss Federal Research Station Agroscope | Muller M.D.,Swiss Federal Research Station Agroscope | Poiger T.,Swiss Federal Research Station Agroscope
Environmental Science and Technology | Year: 2011

Artificial sweeteners are consumed in substantial quantities as sugar substitutes and were previously shown to be ubiquitously present in the aquatic environment. The sweetener saccharin is also registered as additive in piglet feed. Saccharin fed to piglets was largely excreted and, consequently, found in liquid manure at concentrations up to 12 mg/L, where it was stable during 2 months of storage. Saccharin may thus end up in soils in considerable quantities with manure. Furthermore, other studies showed that saccharin is a soil metabolite of certain sulfonylurea herbicides. Sweeteners may also get into soils via irrigation with wastewater-polluted surface water, fertilization with sewage sludge (1-43 μg/L), or through leaky sewers. In soil incubation experiments, cyclamate, saccharin, acesulfame, and sucralose were degraded with half-lives of 0.4-6 d, 3-12 d, 3-49 d, and 8-124 d, respectively. The relative importance of entry pathways to soils was compared and degradation and leaching to groundwater were evaluated with computer simulations. The data suggest that detection of saccharin in groundwater (observed concentrations, up to 0.26 μg/L) is most likely due to application of manure. However, elevated concentrations of acesulfame in groundwater (up to 5 μg/L) may result primarily from infiltration of wastewater-polluted surface water through stream beds. © 2011 American Chemical Society. Source


Buerge I.J.,Swiss Federal Research Station Agroscope | Bachli A.,Swiss Federal Research Station Agroscope | De Joffrey J.-P.,Swiss Federal Research Station Agroscope | Muller M.D.,Swiss Federal Research Station Agroscope | And 2 more authors.
Environmental Science and Technology | Year: 2013

For many chiral pesticides, little information is available on the properties and fate of individual stereoisomers. A basic data set would, first of all, include stereoisomer-specific analytical methods and data on the biological activity of stereoisomers. The herbicide beflubutamid, which acts as an inhibitor of carotenoid biosynthesis, is currently marketed as racemate against dicotyledonous weeds in cereals. Here, we present analytical methods for enantiomer separation of beflubutamid and two metabolites based on chiral HPLC. These methods were used to assign the optical rotation and to prepare milligram quantities of the pure enantiomers for further characterization with respect to herbicidal activity. In addition, sensitive analytical methods were developed for enantiomer separation and quantification of beflubutamid and its metabolites at trace level, using chiral GC-MS. In miniaturized biotests with garden cress, (-)-beflubutamid showed at least 1000× higher herbicidal activity (EC50, 0.50 μM) than (+)-beflubutamid, as determined by analysis of chlorophyll a in 5-day-old leaves. The agricultural use of enantiopure (-)-beflubutamid rather than the racemic compound may therefore be advantageous from an environmental perspective. In further biotests, the (+)-enantiomer of the phenoxybutanoic acid metabolite showed effects on root growth, possibly via an auxin-type mode of action, but at 100× higher concentrations than the structurally related herbicide (+)-mecoprop. © 2012 American Chemical Society. Source

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