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  • 11
    ISSN: 1573-1561
    Keywords: Sex pheromone ; navel orangeworm ; Amyelois transitella ; (Z,Z)-11,13-hexadecadienal ; Pyralidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A sex pheromone of the navel orangeworm,Amyelois transitella (Walker), was obtained from ether rinses of the sex pheromone gland of calling females. The pheromone was isolated by means of liquid and gas chromatography and was identified as one of four possible geometrical isomers of 11,13-hexadecadienal by means of spectroscopic and microchemical methods. Synthesis and laboratory bioassay of all four isomers revealed that only the (Z,Z) isomer was biologically active. (Z,Z)-11,13-hexadecadienal elicited quantitatively similar activation and attraction responses byA. transitella males as did the natural product.
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  • 12
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 6 (1980), S. 473-485 
    ISSN: 1573-1561
    Keywords: Synthesis ; sex pheromone ; Japanese beetle ; Popillia japonica ; (Z)- and (E)-5-(1-decenyl)dihydro-2(3H)-furanone isomers ; enantiomers of (Z)-5-(1-decenyl)dihydro-2(3H)-furanone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The stereospecific synthesis of the sex pheromone produced by the female Japanese beetle (Popillia japonica Newman), (R,Z)-5-1-decenyl)-dihydro-2(3H)-furanone, is described. The pure syntheticR,Z form is a powerful attractant for males of the species in field bioassays and was competitive in attractiveness with live females, whereas the racemicZ isomer and theS,Z enantiomer were strong inhibitors of male response. The saturated analogs of both enantiomers were also synthesized stereospecifically.
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  • 13
    ISSN: 1573-1561
    Keywords: Sex pheromone ; 6,12-dimethylpentadecan-2-one ; ketone ; banded cucumber beetle ; Diabrotica balteata ; Chrysomelidae ; Coleoptera ; attractant
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A sex pheromone produced by female banded cucumber beetle adults,Diabrotica balteata LeConte, was isolated from volatiles trapped on Porapak Q and identified as 6,12-dimethylpentadecan-2-one. The structure was elucidated by spectroscopic analyses and confirmed by synthesis. The synthesized racemic compound was equal to the purified natural pheromone in eliciting responses by banded cucumber beetle males to field traps. A doseresponse characteristic was demonstrated for the racemic material formulated on filter paper or rubber septa and placed in field traps. The absolute configuration at the C-6 and C-12 positions was not established.
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  • 14
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 16 (1990), S. 1131-1153 
    ISSN: 1573-1561
    Keywords: Conjugated triene aldehydes ; tobacco hornworm ; Lepidoptera ; Sphingidae ; spectroscopic characterization ; hexadecatrienal isomers
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Three isomeric conjugated triene aldehydes,(10E,12E,14Z)-10, 12-14-hexadecatrienal (IX), (10E,12Z,14E)-10,12,14-hexadecatrienal (XX), and (10E,12E,14E)-10,12,14-hexadecatrienal (X), two of which are components of theManduca sexta (L.) sex pheromone, have been stereoselectively synthesized and spectroscopically characterized.
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  • 15
    ISSN: 1573-1561
    Keywords: Insecta ; Diptera ; Tephritidae ; Mediterranean fruit fly ; pheromone ; attractant ; Ceratitis capitata ; ethyl-(E)-3-octenoate ; geranyl acetate ; (E,E)-α-farnesene
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Three major components, ethyi-(E)-3-octenoate, geranyl acetate, and (E,E)-α-farnesene, emitted as volatiles by laboratory-reared and wild male medflies were collected and analyzed qualitatively and quantitatively. Peak emission of these compounds occurred during the third to fifth hours of the photophase and differences were observed in the ratios of the three components emitted by male laboratory-reared and wild flies. These three compounds were synthesized, and a method was developed to formulate a synthetic blend that released the compounds in a ratio similar to that emitted by wild male medflies. Attractiveness of the blend to female medflies was demonstrated under field conditions by comparing trap catches. Black spherical traps, baited with the synthetic blend to release 1.6 male equivalents, caught significantly more females than blank traps and traps from which the blend released was 0.3, 3.2 or 6.4 male equivalents.
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  • 16
    ISSN: 1573-1561
    Keywords: Synanthedon pictipes ; Sanninoidea exitiosa ; Sesiidae ; pheromone communication disruption ; insect pheromone trapping ; peachtree borer ; lesser peachtree borer
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The sex pheromone communication of the lesser peachtree borer,Synanthedon pictipes (Grote and Robinson), and the peachtree borer,Sanninoidea exitiosa (Say), can be disrupted by permeation of the atmosphere with their respective sex pheromones, (E,Z)- and (Z,Z)-3,13-octadecadien-1-ol acetate. The two isomers seemed equally effective against both species. Disruption was greatest when the pheromone was evaporated from the tops of the peach trees; also, pheromone traps placed in the tree tops captured significantly more males than did traps placed lower in the trees. Neither the color nor the directional placement in a tree (NE, NW, SE, SW) of pheromone-baited traps influenced captures of male lesser peachtree borers.
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  • 17
    ISSN: 1573-1561
    Keywords: carpenterworm moth ; Prionoxystus robiniae ; (Z,E)-3,5-tetradecadien-1-ol acetate ; pheromone ; electroantennogram
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Electroantennogram analyses of female gland extract and of male antennal responses to synthetic standards suggested that (Z,E)-3,5-tetradecadien-1-ol acetate is a pheromone component for the carpenterworm moth,Prionoxystus robiniae (Peck). The four 3,5-geometrical isomers were synthesized and bioassayed in the laboratory and the field in 1972, 1973, and 1974. TheZ,E isomer was found to be active in the laboratory and a good attractant in the field. The synthesis of theZ,E isomer also produced considerable quantities of theE,E isomer, which is difficult to remove completely. TheE,E isomer does not inhibit the response of males to theZ,E isomer when it is present in amounts up to 20% of theZ,E isomer. The addition of a keeper, a volatility modifier, or an antioxidant prolonged the activity of the attractant for as much as 43 days. (Z,E)-3,5-Tetradecadien-1-ol acetate may be a natural pheromone, but it has not been chemically defined from female extract. There is EAG evidence that a second pheromonal component may be present. The attractant nevertheless provides a tool for population survey, behavioral studies, evaluation of economic impact, and possibly control.
    Type of Medium: Electronic Resource
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  • 18
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 21 (1995), S. 69-79 
    ISSN: 1573-1561
    Keywords: Insecta ; Ceratitus capitata ; medfly ; trimedlure ; enantiomer ; attractant ; lure ; SAR ; VdW ; Chem-X
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract tert-Butyl 4- (and 5-) chloro-trans-2-methylcyclohexane-1-carboxylate (TML), a mixture of four majortrans and four minorcis isomers, is used as an attractant for detecting and monitoring the male Mediterranean fruit fly (medfly),Ceratitis capitata (Wiedemann). The eight isomers (racemic mixtures) were isolated by HPLC, and their relative attractiveness in the field was determined. A quantitative structure-activity relationship (QSAR) was proposed that related a molecular measurement (Å3) of the TML structure to male medfly captures. More recently, thetrans-TML enantiomers were synthesized in sufficient quantities for field testing. This paper reports the computer-aided molecular modeling, via Chem-X, of thetrans-TML enantiomers and the staggered and superimposed fitting with the most attractive isomer, (1S,2S,4R)-TML-C, to determine common volumes and surface areas from Van der Waals (VdW) maps. Observations of structure-activity relationships (SAR) are reported for the staggered fittings.
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  • 19
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 5 (1979), S. 941-953 
    ISSN: 1573-1561
    Keywords: White peach scale ; Pseudaulacaspis pentagona ; pheromone ; attractant ; microtechniques ; enantiomer ; isomers ; (R,Z)-3 ; 9-dimethyl-6-isopropenyl-3 ; 9-decadien-1-ol propionate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Micro techniques were used to obtain spectroscopic and degradative information from less than 5μg of the sex attractant of female white peach scale,Pseudaulascaspis pentagons (Targioni-Tozzetti) isolated from airborne collections. The pheromone was identified as (Z)-3,9-dimethyl-6-isopropenyl-3,9-decadien-1-ol propionate. Both enantiomers of theZ isomer and also the enantiomers of theE isomer were prepared from (R)-or (S)-limonene. Bioassays of material with minimum enantiomeric purity of 95% showed that at extreme dilution only theR,Z isomer attracted male white peach scale; however activity of theS,Z enantiomer could not be completely excluded.
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  • 20
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 6 (1980), S. 271-284 
    ISSN: 1573-1561
    Keywords: Sex pheromone ; attractants ; (E,Z)-3,13-octadecadien-1-ol acetate ; (Z,Z)-3,13-octadecadien-1-ol acetate ; lesser peachtree borer ; Synanthedon pictipes ; peachtree borer ; Synanthedon exitiosa ; 3,13-octadecadien-1-ol isomers ; homopropargylic acetal cleavage ; stereochemistry of dissolving metal reductions
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The sex pheromones produced by females of the lesser peachtree borer,Synanthedon pictipes (Grote and Robinson), and the peachtree borer,Synanthedon exitiosa (Say), (E,Z)- and (Z,Z)-3,13-octadecadien-1-ol acetate, respectively, were synthesized from 1,8-dichlorooctane, lithium acetylide, and ethylene oxide. In the course of the synthesis a new carbon-oxygen cleavage reaction of homopropargylic acetals was found, and the stereochemistry of the dissolving metal reductions of acetylenic alcohols was investigated.
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