Triadimenol 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 triadimenol in two soils were investigated in details. The dissipation of technical triadimenol, 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.

中文翻译：

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土壤中三甲烯醇的立体选择性降解和微生物差聚。

三唑醇是一种广泛使用的三唑类杀菌剂，由四个具有1R，2S，1S，2R，1R，2R和1S，2S构型的立体异构体组成。反式对映异构体对（1R，2S异构体和1S，2R异构体）也称为三二甲酚A和顺式对映异构体对（1R，2R异构体和1S，2S-异构体）三苯甲酚-B. 在这项研究中，详细研究了三土三醇在两种土壤中的立体选择性降解和手性稳定性。工业级三苯甲酚的消散，即三苯甲酚A和三苯二酚B的6：1混合物，在消散过程中发生了从三苯甲酚A到三苯二酚B的显着差向异构。降解表现出一定的立体选择性，导致浓度顺序为1S，2S  >  1R，2R  >  1R，2S  >  1S，2R或1S，2S  >  1R，2R  >  1S，2R  >  1R，2S在保定土壤或武汉土壤分别培养100天后结束。进一步对triadimenol-B的孵育未显示差向异构，即triadimenol-B在土壤中的形态稳定，并且1R，2R- triadimenol的降解速度比1S，2S- triadimenol稍慢一些，而在后半部分则稍快一些。此外，通过孵育对映体纯1S，2R-三苯二酚和1R，2S-三苯二酚，结果记录了每个对映异构体的差向异构化均发生在C-1和C-2位置。最后，本工作还证明了所有四种立体异构体的对映异构化反应在土壤中几乎可以忽略不计。手征性25：355-360 :, 2013.©2013 Wiley Periodicals，Inc.