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  • 1
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 14 (1988), S. 1003-1021 
    ISSN: 1573-1561
    Keywords: Haloacetate ; pheromone analog ; catabolic protein ; EAG ; Plutella xylostella ; Lepidoptera ; Yponomeutidae ; inhibition
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A series of mono-, di-, and trihalogenated acetate analogs of Zl 1–16: Ac were prepared and examined for electrophysiological activity in antennae of males of the diamondback moth,Plutella xylostella. In addition, two potential affinity labels, a diazoacetate (Dza) and a trifluoromethyl ketone (Tfp), were evaluated for EAG activity. The Z11–16∶Ac showed the highest activity in EAG assays, followed by the fluorinated acetates, but other halo-acetates were essentially inactive. The polar diazoacetate and the trifluoromethyl ketone were also very weak EAG stimulants. The effects of these analogs on the hydrolysis of [3H]Z11–16∶Ac to [3H]Z11–16∶OH by antennal esterases was also examined. The three fluorinated acetates showed the greatest activity as inhibitors in competition assays, with rank order F2Ac 〉 F3Ac 〉 FAc 〉 Ac 〉 Cl2Ac 〉 ClAc 〉 Dza 〉 Br2Ac 〉 BrAc 〉 Tfp 〉 I 〉 Cl3Ac 〉 Br3Ac 〉 OH. The relative polarities of the haloacetates, as determined by TLC mobility, are in the order mono- 〉 di- 〉 trihalo, but F, Cl, Br, and I all confer similar polarities within a substitution group. Thus, the steric size appears to be the predominant parameter affecting the interactions of the haloacetate analogs with both receptor and catabolic proteins inP. xylostella males.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Springer
    Biotechnology letters 15 (1993), S. 1139-1144 
    ISSN: 1573-6776
    Source: Springer Online Journal Archives 1860-2000
    Topics: Process Engineering, Biotechnology, Nutrition Technology
    Notes: Summary The investigation of enzyme mediated hydrolysis of the respective cis- and trans-2-(4-methoxybenzyl)-1-cyclohexyl acetates has been provided using several lipases. A comparison of results obtained has been summarized in this paper.
    Type of Medium: Electronic Resource
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  • 3
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The two-step alkylation of phenyl prop-2-enyl sulfone (1) with protected ω-bromoalkanols and 1-iodoalkanes (→3; see Scheme 1) followed by a Pd-catalyzed desulfonylation with LiBH4 affords a 96:4 mixture of vinylbranched, protected alcohols and corresponding ethylidene-branched isomers (see Scheme 2; 4 and 5, respectively). By utilizing the large difference in reactivity of mono- and trisubstituted C=C bonds towards singlet oxygen, the ethylidene derivatives are easily removed from the mixture by photo-oxygenation. The vinyl-branched compounds are inert to this reaction and can be conveniently isolated in highly pure form (99.5%) and ca. 45% overall yield.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
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  • 4
    ISSN: 1573-1561
    Keywords: Sex pheromone ; (E,E)-8,10-dodecadien-1-ol acetate ; antagonist ; inhibitor ; mating disruption ; behavioral observations ; field EAG ; Cydia nigricana ; Tortricidae ; Lepidoptera
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Synthetic sex pheromone of the pea mothCydia nigricana. (E,E)-8,10-dodecadien-1-yl acetate (E8,E10–12 : Ac), was applied in a 3-ha pea field at a rate of 17 g/ha, in two different dispenser formulations. Aerial concentrations within pea canopy, as determined by a field electroantennogram (EAG) apparatus, were 2 and 3 ng/m3 in the two dispenser treatments. The validity of the EAG measurements was corroborated by sampling of field air, followed by gas chromatographic quantification ofE8,E10–12 : Ac. Males were attracted to fresh dispensers releasingE8,E10–12 : Ac plus less than 2% of the antagonisticE, Z; Z, E; andZ, Z isomers. Two days after placement, the proportion of these isomers had increased to 6%. Males were then no longer attracted to the dispensers, but were observed to fly out of the treated field. Male attraction to calling females was almost entirely suppressed, and attraction to traps baited with synthetic pheromone was significantly reduced. Larval infestation in the pheromone-treated field was 2%, compared to 36% in a control field.
    Type of Medium: Electronic Resource
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