Synthesis and fungicidal activity of enantiomerically pure (R)- and (S)-silicon-containing azole fungicides.
Enantiomerically pure (R)- and (S)-1-(1H-1,2,4-triazol-1-yl)-2-(4-fluorophenyl)-3-trimethylsilylpropan-2-ol 1 were prepared via an enantioselective Grignard reaction. The absolute stereochemistry of 1 was determined by X-ray analysis. In a comparison of in vitro antifungal activities of the enantiomers, the (-)-enantiomer with the R-absolute configuration was far more potent than the (+)-enantiomer.
Itoh
Hiroyuki
H
Agroscience Research Laboratories, Sankyo Agro Co., Ltd, 894, Yasu, Yasu-cho, Yasu-gun, Shiga-ken 520-2342, Japan. hiroit@yasu.sankyo.co.jp
Furukawa
Youji
Y
Tsuda
Mikio
M
Takeshiba
Hideo
H
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001393:Azoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D006038:Glyoxylates / Q000737:chemistry; D020128:Inhibitory Concentration 50; D008333:Mandelic Acids; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D012275:Oryza / Q000382:microbiology; D010935:Plant Diseases / Q000382:microbiology; D020005:Propanols / Q000737:chemistry*; D012232:Rhizoctonia / Q000187:drug effects; D012825:Silicon / Q000737:chemistry*; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
C494926:1-(1H-1,2,4-triazol-1-yl)-2-(4-fluorophenyl)-3-trimethylsilylpropan-2-ol; D000935:Antifungal Agents; D001393:Azoles; D006038:Glyoxylates; D008333:Mandelic Acids; D020005:Propanols; D014297:Trimethylsilyl Compounds; C012482:phenylglyoxylic acid; D012825:Silicon