- Azole compounds, their production and use
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PCT No. PCT/JP96/00325 Sec. 371 Date Oct. 17, 1996 Sec. 102(e) Date Oct. 17, 1996 PCT Filed Feb. 15, 1996 PCT Pub. No. WO96/25410 PCT Pub. Date Aug. 20, 1996The present invention provides an azole compound represented by the formula (I): wherein Ar is an
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- Optically active antifungal azoles. VI. Synthesis and antifungal activity of N-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl) propyl]-N′-(4-substituted phenyl)-3(2H,4H)-1,2,4-triazolones and 5(1H,4H)-tetrazolones
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A new series of optically active antifungal azoles, N-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl) propyl]-N′-(4-substituted phenyl)-3(2H,4H)-1,2,4-triazolones (1,2) and 5(1H,4H)-tetrazolones (3), were prepared from the triflate derivative of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (13) by an SN2 displacement reaction with the union of an azolone (17-19) and subsequent ring-opening reaction with 1H-1,2,4-triazole. The optically active oxiranylethanol 13 was synthesized from methyl (R)-lactate in a stereocontrolled manner. The azolones 1-3 prepared showed potent antifungal activities in vitro and in vivo.
- Kitazaki, Tomoyuki,Tamura, Norikazu,Tasaka, Akihiro,Matsushita, Yoshihiro,Hayashi, Ryogo,Okonogi, Kenji,Itoh, Katsumi
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p. 314 - 327
(2007/10/03)
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- Optically active tetrazole compounds, and fungicidal compositions thereof
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An optically active azole compound of the formula (I): STR1 wherein R1 and R2 are independently a hydrogen atom, a halogen atom, a haloalkyl group, a haloalkoxy group or an optionally substituted nitrogen-containing heterocyclic group; R3 is a hydrogen atom or an acyl group; Q is CH or N; --NA is a nitrogen-containing aromatic five-membered heterocyclic group having at least two adjacent nitrogen atoms as the ring-constituting atoms which may be substituted, or an aromatic condensed heterocyclic group having two or more nitrogen atoms as the ring-constituting atoms which may be substituted; and (R) shows that the carbon atom marked with (R) has R-configuration; provided that either of R1 and R2 is an optionally substituted nitrogen-containing heterocyclic group when --NA is an 1H-1,2,4-triazol-1-yl group, or a salt thereof, which is useful as an antifungal agent.
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