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- Title
Stereoselective Degradation and Microbial Epimerization of.
- Authors
Li, Zhaoyang; Li, Qiaoling; Zhao, Jiahe; Wang, Weixiao
- Abstract
ABSTRACT is a widely used triazole fungicide and consists of four stereoisomers with 1R,2S, 1S,2R, 1R,2R, and 1S,2S configurations. The trans-enantiomeric pair ( 1R,2S-isomer and 1S,2R-isomer) is also called triadimenol-A and the cis-enantiomeric pair ( 1R,2R-isomer and 1S,2S-isomer) triadimenol-B. In this study, the stereoselective degradation and chiral stability of in two soils were investigated in details. The dissipation of technical , a 6:1 mixture of triadimenol-A and triadimenol-B, showed significant epimerization from triadimenol-A to triadimenol-B occurred along with the dissipation process. The degradation exhibited some stereoselectivity, resulting in a concentration order of 1S,2S > 1R,2R > 1R,2S > 1S,2R or 1S,2S > 1R,2R > 1S,2R > 1R,2S at the end of the 100 days incubation for Baoding soil or Wuhan soil, respectively. Further incubation of triadimenol-B revealed no epimerization, i.e. triadimenol-B was configurationally stable in soil, and 1R,2R-triadimenol degraded slightly slower in the former part and slightly faster in the later part of the incubation than 1S,2S-triadimenol. Moreover, by incubation of enantiopure 1S,2R-triadimenol and 1R,2S-triadimenol, the results documented the epimerization for each enantiomer occurred at both C-1 and C-2 positions. Finally, the present work also documented that the enantiomerization reaction for all the four stereoisomers was nearly negligible in the soils. Chirality 25:355-360:, 2013. © 2013 Wiley Periodicals, Inc.
- Subjects
EPIMERIZATION; TRIAZOLES; STEREOSELECTIVE reactions; STEREOISOMERS; TRIADIMEFON; ENERGY dissipation
- Publication
Chirality, 2013, Vol 25, Issue 6, p355
- ISSN
0899-0042
- Publication type
Article
- DOI
10.1002/chir.22175