Identification and formation pattern of metabolites of cyazofamid by soil fungus Cunninghamella elegans
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This study was performed to investigate the formation of microbial metabolites from cyazofamid by the soil fungus Cunninghamella elegans. The incubation of cyazofamid with C. elegans was conducted for 10 days. Cyazofamid disappeared after 7 days of incubation, producing three metabolites. Metabolites identified by liquid chromatography–tandem mass spectrometry were 4-chloro-5-(4-(hydroxymethyl)phenyl)-imidazole-2-carbonitrile (CHCN), 4-(4-chloro-2-cyanoimidazole-5-yl)benzoic acid (CCBA) and 4-chloro-2-cyano-5-(4-(hydroxymethyl)phenyl)N,N-dimethyl-1H-imidazole-1-sulfonamide (CCHS). A new metabolite, CCHS, was further confirmed by 1H-13C HSQC (heteronuclear single-quantum correlation) using nuclear magnetic resonance. As a possible metabolic pathway, cyazofamid could be oxidized to CCHS, degraded to CHCN and further oxidized to CCBA. The metabolic system of C. elegans would be a powerful tool for predicting and identifying phase I metabolites that could be formed in mammalian systems.
KeywordsCunninghamella elegans Cyazofamid Liquid chromatography–tandem mass spectrometry Metabolite Nuclear magnetic resonance
- Evaluation Report Cyazofamid (2004) Food safety commission pesticides experts committee. https://www.fsc.go.jp/english/evaluationreports/pesticide/cyazofamid_fullreport.pdf
- Pestcide Fact Sheet Cyazofamid (2004). United States Environmental Protection Agency. http://www.epa.gov/pesticides/chem_search/reg_actions/registration/fs_PC-085651_01-Sep-04.pdf
- Tomlin C (2009) The pesticide manual: a world compendium, 15th edn. British Crop Protection Council, AltonGoogle Scholar
- Tseng SH et al (2009) Analysis of 81 pesticides and metabolite residues in fruits and vegetables by diatomaceous earth column extraction and LC/MS/MS determination. J Food Drug Anal 17:319–332Google Scholar