title: Metabolism of strobilurins by wheat cell suspension cultures.
abstract: Strobilurin fungicides are a leading class of antifungal chemicals used today in agricultural applications. Although degradation of some strobilurin fungicides has been assessed in plant residues, little information has appeared in the literature concerning the rates of metabolism of these fungicides in plants. In this study, we explored plant metabolism of three strobilurin fungicides, azoxystrobin, kresoxim-methyl, and trifloxystrobin, using wheat cell suspension cultures. Trifloxystrobin and kresoxim-methyl were completely metabolized within 24 h, whereas the metabolism of azoxystrobin was relatively slow with half-lives up to 48 h depending on specific experimental conditions. Metabolic rates of these fungicides were affected by the amounts of compound and cells added to the media. Structural analysis of metabolites of trifloxystrobin and kresoxim-methyl by high-resolution mass spectrometry (HRMS) and nuclear magnetic resonance spectroscopy (NMR) indicated that trifloxystrobin was first demethylated followed by subsequent hydroxylation, whereas kresoxim-methyl was largely demethylated. In contrast, a number of minor metabolites of azoxystrobin were present suggesting a differential metabolism of strobilurins by wheat cells.
authors.affiliation: Discovery Research, Dow AgroSciences LLC, 9330 Zionsville Road, Indianapolis, Indiana 46268, United States. Kmyung@dow.com
authors.forename: Kyung
authors.initials: K
authors.lastname: Myung
authors.forename: Daniel A
authors.initials: DA
authors.lastname: Williams
authors.forename: Quanbo
authors.initials: Q
authors.lastname: Xiong
authors.forename: Scott
authors.initials: S
authors.lastname: Thornburgh
mesh_terms: D000085:Acetates / Q000378:metabolism; D002478:Cells, Cultured; D005231:Fatty Acids, Unsaturated / Q000378:metabolism*; D005659:Fungicides, Industrial / Q000378:metabolism*; D006868:Hydrolysis; D007097:Imines / Q000378:metabolism; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008689:Methacrylates / Q000378:metabolism; D010648:Phenylacetates / Q000378:metabolism; D011743:Pyrimidines / Q000378:metabolism; D000073739:Strobilurins; D014908:Triticum / Q000166:cytology / Q000378:metabolism*
chemical_list: D000085:Acetates; D005231:Fatty Acids, Unsaturated; D005659:Fungicides, Industrial; D007097:Imines; D008689:Methacrylates; D010648:Phenylacetates; D011743:Pyrimidines; D000073739:Strobilurins; C469328:kresoxim-methyl; C467051:trifloxystrobin; C087670:azoxystrobin