An economical synthesis of the major sex attractant of the oak leaf roller?cis-10-tetradecenyl acetate

Hendry, Lawrence B.; Korzeniowski, Stephen H.; Hindenlang, D. M.; Kosarych, Zenyk; Mumma, R. O.; Jugovich, J.

doi:10.1007/bf00988833

Cited by 23 publications

(4 citation statements)

References 9 publications

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“…A series of (Z)-9-alkenes, i.e., (Z)-9-pentacosene, heptacosene, nonacosene and hentriacontene were respectively synthesized from 1-nonyne and corresponding bromides by acetylene coupling reactions in HMPA (Hendry et al, 1975) and the alkynes were subsequently reduced on Lindlar catalyst in 50% hexane in ethanol. The alkenes were purified by chromatography on silica gel impregnated with 10% silver nitrate, which resulted in more than 99.5% purity.…”

Section: Methodsmentioning

confidence: 99%

Direct behavioral evidence for hydrocarbons as nestmate recognition cues in Formica japonica (Hymenoptera: Formicidae)

Akino

Yamamura

Wakamura

et al. 2004

Appl. Entomol. Zool.

161

137

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Here we report direct evidence that cuticular hydrocarbons are responsible for nestmate recognition in Formica japonica distributing in Southern Honshu in Japan. Workers showed aggressive behavior against foreign workers but not against nestmates. A similar response was observed when a glass dummy was treated with isolated hydrocarbons from foreign workers or nestmates. Among the isolated hydrocarbons, ten hydrocarbon components were identified: five nalkanes and five (Z)-9-alkenes with odd number of carbons from 25 to 33, in different ratios in different colonies. When synthetic hydrocarbons blended in the same ratio as natural blends were presented to workers, they showed aggressive responses against foreign blends but paid less attention to those of nestmates. Neither n-alkane nor (Z)-9-alkene blends, however, caused aggression response in foreign workers. Thus, both n-alkanes and (Z)-9-alkenes are necessary to discriminate nestmates from foreign conspecifics.

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Section: Methodsmentioning

confidence: 99%

Direct behavioral evidence for hydrocarbons as nestmate recognition cues in Formica japonica (Hymenoptera: Formicidae)

Akino

Yamamura

Wakamura

et al. 2004

Appl. Entomol. Zool.

161

137

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“…1). Z8-140Ac and 28-tetradecenyl alcohol (28-140H) were synthesized (Hendry et al 1975) with isomeric purity >99% and >97%, respectively. Field Experiments.…”

Section: Introductionmentioning

confidence: 99%

SEX PHEROMONE COMPONENTS OF THE EYESPOTTED BUD MOTH, SPILONOTA OCELLANA (DENIS AND SCHIFFERMÜLLER) (LEPIDOPTERA: OLETHREUTIDAE)

McBrien

Gries

et al. 1991

Can Entomol

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Z8-tetradecenyl acetate (Z8-14OAc andZ8-tetradecenyl alcohol (Z8-14OH) were identified as sex pheromone components of the eyespotted bud moth, Spilonota ocellana (Denis and Schiffermüller) (Lepidoptera: Olethreutidae). Compounds were identified by gas chrornatographic-eleclroantennographic (GC-EAD) and GC-mass spectroscopic analyses and field tested in apple orchards in the Okanagan Valley, B.C. Although Z8-14OAc alone was attractive to male S. ocellana, the addition of 1–5% Z8-14OH strongly synergized its attraction. Field tests comparing the attractiveness of virgin female S. ocellana with various doses of a 99:1 blend of Z8-14OAc and Z8-14OH indicated the natural sex pheromone has only two significant components. A 99:1 blend of Z8-14OAC and Z8-14OH is suggested for monitoring and control of S. ocellana populations in British Columbia.

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“…1974). Z8-140Ac and 28-tetradecenyl alcohol (28-140H) were synthesized (Hendry et al 1975) with isomeric purity >99% and >97%, respectively. We report the identification and field testing of sex pheromone components for S. ocellana.…”

Section: Introductionmentioning

confidence: 99%

NEW RECORDS OF OTIORHYNCHUS GERMAR SPECIES IN WESTERN NORTH AMERICA (COLEOPTERA: CURCULIONIDAE)

Anderson

1991

Can Entomol

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Seventeen species of the genus Otiorhynchus are known to occur in North America (including Greenland) (O'Brien and Wibmer 1982; Wibmer and O'Brien 1989). Warner and Negley (1976) provide a key to 16 species (not including O. monticola Germar, since recorded from Greenland) and provide information on distribution and natural history. All species occurring on mainland North America are known to be introduced. Whereas some of the species have broad distributions in North America, for example O. ovatus (L.), others are known from only a few adjacent localities. Species such as O. singularis (L.) and O. sulcatus (F.) are found in both western and eastern North America but not in intervening areas. Such distributions likely represent separate introductions.

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An economical synthesis of the major sex attractant of the oak leaf roller?cis-10-tetradecenyl acetate

Cited by 23 publications

References 9 publications

Direct behavioral evidence for hydrocarbons as nestmate recognition cues in Formica japonica (Hymenoptera: Formicidae)

Direct behavioral evidence for hydrocarbons as nestmate recognition cues in Formica japonica (Hymenoptera: Formicidae)

SEX PHEROMONE COMPONENTS OF THE EYESPOTTED BUD MOTH, SPILONOTA OCELLANA (DENIS AND SCHIFFERMÜLLER) (LEPIDOPTERA: OLETHREUTIDAE)

NEW RECORDS OF OTIORHYNCHUS GERMAR SPECIES IN WESTERN NORTH AMERICA (COLEOPTERA: CURCULIONIDAE)

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