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Enantioselective Degradation of the Chiral Fungicides Metalaxyl and Furalaxyl by Brevibacillus brevis
Author(s) -
Sulimma Lutz,
Bullach Anke,
Kusari Souvik,
Lamshöft Marc,
Zühlke Sebastian,
Spiteller Michael
Publication year - 2013
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22158
Subject(s) - enantioselective synthesis , chemistry , metalaxyl , enantiomer , fungicide , microorganism , chromatography , degradation (telecommunications) , organic chemistry , botany , bacteria , catalysis , biology , telecommunications , computer science , genetics
For almost four decades, the chiral fungicides metalaxyl and furalaxyl have been in use in plant protection on a global scale. Both substances are distributed as racemic mixtures, yet the desirable interference in nucleic acid synthesis of harmful fungi only occurs by the (‐)‐ R ‐enantiomer. As enantioselective degradation in Scheyern (Germany) and Yaoundé (Cameroon) soils has been documented, the influence of 50 isolated microorganisms on the R/S ratio was investigated. A high‐pressure liquid chromatography method with a chiral column to separate enantiomers of metalaxyl and furalaxyl, and subsequent detection by tandem mass spectrometry, was employed. Only one of these microorganisms, a strain of Brevibacillus brevis , showed an enantioselective degradation pattern in liquid culture; the respective (‐)‐ R ‐enantiomers were preferably degraded. Moreover, (‐)‐ R ‐furalaxyl was degraded faster in cultures supplemented simultaneously with both fungicides of the same concentration. Chirality 25 : 336–340 , 2013 . © 2013 Wiley‐Liss Inc. Chirality 00:000‐000:, 2013. © 2013 Wiley Periodicals, Inc.