Synthesis and Fungicidal Activity of 1-(α-tert-Butylcinnamoyl)imidazoles

Several 1-(α-tert-butylcinnamoyl)imidazoles were prepared to examine their fungicidal activity. The (Z)-4-chlorocinnamoyl derivative was prepared from (anti)-2-tert-butyl-3-(4-chlorophenyl)-3-hydroxypropanoic acid by treating with 1,1′-carbonyldiimidazole and a subsequent β-elimination reaction at a...

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Bibliographic Details
Published in:Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2002-10, Vol.66 (10), p.2243-2246
Main Authors: MANABE, Akio, TAKANO, Hirotaka, FURUZAWA, Kunihiko, YANAGI, Kazunori, HISADA, Yoshio, TANAKA, Shizuya
Format: Article
Language:English
Subjects:
1-cinnamoylimidazole
Ascomycota - drug effects
azole fungicide
Biological and medical sciences
Botrytis - drug effects
Chemical Phenomena
Chemistry, Physical
Cinnamates - chemical synthesis
Cinnamates - toxicity
Crystallography, X-Ray
Fundamental and applied biological sciences. Psychology
fungicidal activity
Fungicides, Industrial - chemical synthesis
Fungicides, Industrial - toxicity
geometrical isomer
Imidazoles - chemical synthesis
Imidazoles - toxicity
Indicators and Reagents
Magnetic Resonance Spectroscopy
Models, Molecular
Plant Diseases - microbiology
β-elimination reaction
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Summary:Several 1-(α-tert-butylcinnamoyl)imidazoles were prepared to examine their fungicidal activity. The (Z)-4-chlorocinnamoyl derivative was prepared from (anti)-2-tert-butyl-3-(4-chlorophenyl)-3-hydroxypropanoic acid by treating with 1,1′-carbonyldiimidazole and a subsequent β-elimination reaction at an elevated temperature. The (Z)-isomer of the 4-chlorocinnamoyl derivative showed good fungicidal activity against Erysiphe graminis and Botrytis cinerea in pot tests, whereas the corresponding (E)-isomer derived from the (Z)-isomer through photoisomerization was much less active.
ISSN:0916-8451
1347-6947
DOI:10.1271/bbb.66.2243