Biotransformation of phenylurea herbicides by a soil bacterial strain, Arthrobacter sp. N2: structure, ecotoxicity and fate of diuron metabolite with soil fungi.
In order to assess the influence of the aromatic substitution on the ability of a soil bacterial strain, Arthrobacter sp. N2, to degrade phenylurea herbicides, biotransformation assays were performed in mineral medium with resting cells of this soil bacterial strain on three phenylurea herbicides (diuron, chlorotoluron and isoproturon). Each herbicide considered, led to the formation of only one metabolite detected by HPLC analysis. After isolation, the metabolites were identified by NMR and MS, as the corresponding substituted anilines. According to the Microtox test (realized on the bacterium Vibrio fischeri), these metabolites presented non-target toxicity far more important (up to 600 times higher for 4-isopropylaniline) than the parent molecule. For isoproturon and chlorotoluron, the amount of substituted anilines obtained at the end of the biotransformation was very low, whereas the biotransformation of diuron into 3,4-dichloroaniline was almost quantitative. In this last case, the degradation product accumulated in the medium. In soil, other microorganisms are present that might degrade it. So the biotransformation of 3,4-dichloroaniline was then tested with four fungal strains: Aspergillus niger, Beauveria bassiana, Cunninghamella echinulata var. elegans and Mortierella isabellina. The aniline was further transformed with all the microorganisms tested. Only one metabolite was detected by HPLC analysis and after isolation, it was identified to be 3,4-dichloroacetanilide. This acetylated compound led to biological effects less important on V. fischeri than 3,4-dichloroaniline. These results stress the importance of identifying the degradation products to assess the impact of a polluting agent. Indeed, the pollutant may undergo transformation yielding compounds more toxic than the parent molecule.
Tixier
Céline
C
Synthèse et Etude de Systèmes à Intérêt Biologique, UMR 6504, Université Blaise Pascal, 63177 Aubière, France.
Sancelme
Martine
M
Aït-Aïssa
Selim
S
Widehem
Pascale
P
Bonnemoy
Frédérique
F
Cuer
Annie
A
Truffaut
Nicole
N
Veschambre
Henri
H
D001173:Arthrobacter / Q000502:physiology*; D001711:Biotransformation; D004237:Diuron / Q000737:chemistry / Q000378:metabolism* / Q000633:toxicity; D005658:Fungi / Q000187:drug effects; D006540:Herbicides / Q000737:chemistry / Q000378:metabolism* / Q000633:toxicity; D008782:Methylurea Compounds / Q000737:chemistry / Q000378:metabolism* / Q000633:toxicity; D010671:Phenylurea Compounds / Q000737:chemistry / Q000378:metabolism* / Q000633:toxicity; D012989:Soil Pollutants / Q000378:metabolism*; D013329:Structure-Activity Relationship
D006540:Herbicides; D008782:Methylurea Compounds; D010671:Phenylurea Compounds; D012989:Soil Pollutants; C028904:isoproturon; D004237:Diuron; C007033:chlortoluron