A bacterial strain able to transform iprodione was isolated from a fast iprodione-degrading soil by enrichment procedures. Transformation was detected through 3,5-dichloroaniline production as measured by a rapid colorimetric method. The strain, MA6, was tentatively identified as an Arthrobacter sp. When it was incubated with MA6 in a minimum mineral medium (pH 6.5), iprodione (8.8 mol/liter) was transformed into two major metabolites that were identified by high-performance liquid chromatography analysis: 3,5-dichlorophenylcarboximide (metabolite 1) and (3,5-dichlorophenylurea)acetic acid (metabolite 2), which was produced after ring cleavage of the former product. These products were synthesized in the laboratory and compared with metabolites 1 and 2 which were formed during iprodione degradation. Small quantities of 3,5-dichloroaniline also appeared in the bacterial culture but did not substantially increase between the first and second days of incubation. In contrast, in the sterile control medium, iprodione was spontaneously transformed into hydantoic acid and an iprodione isomer. Chemical and biological transformations of iprodione seem to occur through two different pathways. One biological degradation pathway is proposed.
Three bacterial strains were isolated from soils adapted to iprodione and identified as Pseudomonas fluorescens, Pseudomonas sp. and Pseudomonas paucimobilis. The first two strains transformed iprodione to N‐(3,5‐dichlorophenyl)‐2,4‐dioxoimidazolidine (II) and under restrictive conditions to 3,5‐dichlorophenylurea acetic acid (III); the latter subsequently degraded II to III and III to 3,5‐dichloroaniline (3,5‐D). We constructed bacterial combinations consisting of Pseudomonas paucimobilis plus one of the iprodione degraders and showed that these combinations transformed iprodione into 3,5‐D. It is known that 3,5‐D was the major metabolite found in adapted soils, suggesting that such a bacterial combination might be responsible for degrading iprodione into 3,5‐D in adapted soils. Plasmids could only be isolated in Pseudomonas fluorescens but we did not investigate if one of these was involved in the ability to degrade iprodione.
Two mixed bacterial cultures were isolated from a French soil adapted to the dicarboximide fungicide vinclozolin. The vinclozolin was transformed by the mixed bacterial cultures according to two degradation pathways: (a) the formation of 2-[[(3,5-dichlorophenyl)carbamoyl]oxy]-2-methyl-3-butenoic acid and then 3,5-dichloroaniline or (b) the formation of 3‘,5‘-dichloro-2-hydroxy-2-methylbut-3-enanilide and then 3,5-dichloroaniline. The structure of 2-[[(3,5-dichlorophenyl)carbamoyl]oxy]-2-methyl-3-butenoic acid was unambiguously established by 1H and 13C 2-D NMR analysis. A bacterial strain isolated from soil that degrades this compound was identified as a strain of Corynebacterium sp. Attempts to obtain pure vinclozolin-degrading strains via 3‘,5‘-dichloro-2-hydroxy-2-methylbut-3-enanilide were unsuccessful. Keywords: Vinclozolin; fungicide-degrading bacteria; chemical transformation
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