Penipratynolene, a novel nematicide from penicillium bilaiae Chalabuda.
New acetylenic nematicidal compound, penipratynolene (1), methy (2'R)-4-(2'-hydroxy-3'-butynoxy)benzoate, together with two known compounds, 6-methoxycarbonylpicolinic acid (2) and 2,6-pyridinedicarboxylic acid (3), were isolated from the culture filtrate of Penicillium bilaiae Chalabuda. The structures of 1-3 were established by spectroscopic methods. The absolute configuration of 1 was confirmed by using a modified version of Mosher's method. Compounds 1-3 showed nematicidal activity of 77%, 52%, and 98%, respectively, by a bioassay at 300 mg/l with the root-lesion nematode Pratylenchus penetrans.
Nakahara
Satoshi
S
Department of Biological and Environmental Chemistry, Faculty of Agriculture, Tottori University, Tottori-shi, Japan.
Kusano
Miyako
M
Fujioka
Shozo
S
Shimada
Atsumi
A
Kimura
Yasuo
Y
D000480:Alkynes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D000818:Animals; D000969:Antinematodal Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D001565:Benzoates / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D004353:Drug Evaluation, Preclinical; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010407:Penicillium / Q000737:chemistry* / Q000378:metabolism; D013237:Stereoisomerism; D014431:Tylenchoidea / Q000187:drug effects
D000480:Alkynes; D000969:Antinematodal Agents; D001565:Benzoates; C492602:methyl 4-(2'-hydroxy-3'-butynoxy)benzoate