Synthesis and antinematodal activity of 3-n-alkylphenols

Kazuto Takaishi; Yohannes Alen; Kazuyoshi Kawazu; Naomichi Baba; Shuhei Nakajima

doi:10.1271/bbb.68.2398

Synthesis and antinematodal activity of 3-n-alkylphenols

Kazuto Takaishi, Yohannes Alen, Kazuyoshi Kawazu, Naomichi Baba, Shuhei Nakajima

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	2398-2400
Number of pages	3
Journal	Bioscience, Biotechnology and Biochemistry
Volume	68
Issue number	11
DOIs	https://doi.org/10.1271/bbb.68.2398
Publication status	Published - Nov 2004

Keywords

3-alkylphenols
3-nonylphenol
3-undecylphenol
Antinematodal activity
Bursapherencus xylophilus

ASJC Scopus subject areas

Biotechnology
Analytical Chemistry
Biochemistry
Applied Microbiology and Biotechnology
Molecular Biology
Organic Chemistry

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10.1271/bbb.68.2398

Cite this

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title = "Synthesis and antinematodal activity of 3-n-alkylphenols",

abstract = "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.",

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author = "Kazuto Takaishi and Yohannes Alen and Kazuyoshi Kawazu and Naomichi Baba and Shuhei Nakajima",

year = "2004",

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T1 - Synthesis and antinematodal activity of 3-n-alkylphenols

AU - Takaishi, Kazuto

AU - Alen, Yohannes

AU - Kawazu, Kazuyoshi

AU - Baba, Naomichi

AU - Nakajima, Shuhei

PY - 2004/11

Y1 - 2004/11

N2 - 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.

AB - 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.

KW - 3-alkylphenols

KW - 3-nonylphenol

KW - 3-undecylphenol

KW - Antinematodal activity

KW - Bursapherencus xylophilus

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ER -

Synthesis and antinematodal activity of 3-n-alkylphenols

Abstract

Keywords

ASJC Scopus subject areas

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