Synthesis and antinematodal activity of 3-n-alkylphenols.
Several 3-alkylphenols including 3-undecylphenol, which was isolated from a Sumatran rainforest plant, were synthesized to investigate their antinematodal activity against the phytopathogenic nematodes, Bursapherencus xylophilus. A three-step synthesis involving the treatment of 2-cyclohexen-1-one with the Grignard reagent, oxidation of the resulting 1-alkyl-2-cyclohexen-1-ol and subsequent aromatization of 3-alkyl-2-cyclohexen-1-one successfully afforded such phenols. Among the 3-alkylphenols, 3-nonylphenol showed the highest activity, while 3-decylphenol and 3-undecylphenol also showed high activity.
Takaishi
Kazuto
K
The Graduate School of Natural Science and Technology, Laboratory of Natural Product Chemistry, Okayama University, Japan.
Alen
Yohannes
Y
Kawazu
Kazuyoshi
K
Baba
Naomichi
N
Nakajima
Shuhei
S
D000818:Animals; D000969:Antinematodal Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009348:Nematoda; D010636:Phenols / Q000138:chemical synthesis* / Q000494:pharmacology*; D021241:Spectrometry, Mass, Electrospray Ionization; D013329:Structure-Activity Relationship
D000969:Antinematodal Agents; D007202:Indicators and Reagents; D010636:Phenols