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  • 1
    ISSN: 1573-1561
    Keywords: Mediterranean fruit fly ; Ceratitis capitata Diptera ; Tephritidae ; attractant ; trimedlure ; stereoisomers ; enantiomers
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The most biologically active enantiomer of trimedlure, a synthetic lure attractive to male Mediterranean fruit flies, is the 1S,2S,4R enantiomer of isomer C, the fert-butyl ester of ris-4-chloro-trans-2-methylcyclohexanecarboxylic acid. We also determined that the 1R,2R,5S enantiomer of isomer A is significantly more attractive than its optical antipode. Essential differences in the current synthetic work that are critical to possible commercialization of this preparation are detailed herein.
    Type of Medium: Electronic Resource
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  • 2
    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.
    Type of Medium: Electronic Resource
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  • 3
    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.
    Type of Medium: Electronic Resource
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  • 4
    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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  • 5
    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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