Identification of new metabolic pathways in the enantioselective fungicide tebuconazole biodegradation by Bacillus sp. 3B6

• Published in: Journal of hazardous materials Vol. 351; pp. 160 - 168
• Main Authors: Youness, Mohamed, Sancelme, Martine, Combourieu, Bruno, Besse-Hoggan, Pascale
• Format: Journal Article
• Language: English
• Published: Netherlands Elsevier B.V 05-06-2018; Elsevier
• Subjects: Bacillus sp. 29B3; Chemical Sciences; Kinetics; LC–MS; Metabolites; NMR; Bacillus sp. 29B3; NMR; Kinetics; Metabolites; LC–MS
• ISSN: 0304-3894; 1873-3336
• DOI: 10.1016/j.jhazmat.2018.02.048

•Tebuconazole is biotransformed enantioselectively by Bacillus sp. 3B6.•New metabolites were identified by combining LC–MS and 1D/2D NMR.•Two hydroxylated and a dehydrated metabolites were formed.
The use of triazole fungicides in various fields ranging from agriculture to therapy, can cause long-term undesirable effects on different organisms from various environmental compartments and lead to resistance phenomena (even in humans) due to their extensive use and persistence. Their occurrence in various water bodies has increased and tebuconazole, in particular, is often detected, sometimes in high concentration. Only a few bacterial and fungal strains have been isolated and found to biotransform this fungicide, described as not easily biodegradable. Nevertheless, the knowledge of efficient degrading-strains and metabolites potentially formed could improve bioremediation process and global overview of risk assessment. Therefore, a broad screening of microorganisms, isolated from various environmental compartments or from commercially-available strain collections, allowed us to find six bacterial strains able to biotransform tebuconazole. The most efficient one was studied further: this environmental strain Bacillus sp. 3B6 biotransforms the fungicide enantioselectively (ee = 18%) into two hydroxylated metabolites, one of them being transformed in its turn to alkene by a biotic dehydration reaction. This original enantioselective pathway shows that racemic pesticides should be treated by the environmental risk assessment authorities as a mixture of two compounds because persistence, biodegradation, bioaccumulation and toxicity often show chiral dependence.