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Regio- and Stereochemical Study of Sex Pheromone of Pine Sawfly; <i>Diprion</i> <i>nipponica</i>

Akira TaiFaculty of Science, Himeji Institute of TechnologyKohto, Kamigori, Ako-gun, Hyogo 678-1297Emi SyounoFaculty of Science, Himeji Institute of TechnologyKohto, Kamigori, Ako-gun, Hyogo 678-1297Kazuki TanakaFaculty of Science, Himeji Institute of TechnologyKohto, Kamigori, Ako-gun, Hyogo 678-1297Morifumi FujitaFaculty of Science, Himeji Institute of TechnologyKohto, Kamigori, Ako-gun, Hyogo 678-1297Takashi SügimuraFaculty of Science, Himeji Institute of TechnologyKohto, Kamigori, Ako-gun, Hyogo 678-1297Yasutomo HigashiuraSchool of Life Science, Tokyo University of Pharmacy and Life ScienceHorinouchi, Hachiouji, Tokyo 192-0392Masashi KakizakiHideho HaraHokkaido Forestry Research InstituteKoshunai, Bibai, Hokkaido, 079-0198Tikahiko NaitoFaculty of Agriculture, Kobe UniversityRokkoudai, Nada, Kobe, 657-0013

Bulletin of the Chemical Society of Japanjournal2002en

ABI

Annotatsiya

Abstract Regio- and stereoisomers of 1,2,ω-trimethyldecyl propionate (ω = 5–9) were prepared from stereochemically pure chiral building blocks as sex pheromone candidates of a pine sawfly; Diprion nipponica. Among the synthesized candidates, (1S,2R,8S)-1,2,8-trimethyldecyl propionate was found to be the sex pheromone of D. nipponica, based on compatibility of its GC-MS data with that of the extract of females, and its significantly high pheromone activity in a field bioassay. The field bioassay of the synthesized compounds also revealed that (1S,2R,8R)-1,2,8-trimethyldecyl propionate, (1S,2R,7S)-1,2,7-trimethyldecyl propionate, and (1S,2R,6S)-1,2,6-trimethyldecyl propionate could attract male sawflies to some extent as pheromone mimics.

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Mavzular

Forest Insect Ecology and Management Insect Pheromone Research and Control Insect and Pesticide Research

Identifikatorlar

DOI: 10.1246/bcsj.75.111

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