Synthesis and fungicidal activity of 1-(alpha-tert-butylcinnamoyl)imidazoles.
Several 1-(alpha-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 beta-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.
Manabe
Akio
A
Agricultural Chemicals Research Laboratory, Sumitomo Chemical Co. Ltd., 4-2-1 Takatsukasa, Takarazuka, Hyogo 665-8555, Japan. manabe@sc.sumitomo-chem.co.jp
Takano
Hirotaka
H
Furuzawa
Kunihiko
K
Yanagi
Kazunori
K
Hisada
Yoshio
Y
Tanaka
Shizuya
S
D001203:Ascomycota / Q000187:drug effects*; D020171:Botrytis / Q000187:drug effects*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002934:Cinnamates / Q000138:chemical synthesis* / Q000633:toxicity*; D018360:Crystallography, X-Ray; D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000633:toxicity*; D007093:Imidazoles / Q000138:chemical synthesis* / Q000633:toxicity*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010935:Plant Diseases / Q000382:microbiology*
D002934:Cinnamates; D005659:Fungicides, Industrial; D007093:Imidazoles; D007202:Indicators and Reagents