| 1. |
- Manrique, G., et al.
(författare)
-
Chemical Communication in Chagas Disease Vectors. Source, Identity and Potential Function of Volatiles Released by the Metasternal and Brindleys Glands of Triatoma infestans Adults
- 2006
-
Ingår i: Journal of Chemical Ecology. - : Springer. - 0098-0331 .- 1573-1561. ; 32:9, s. 2035-2052
-
Tidskriftsartikel (refereegranskat)abstract
- Compounds from the metasternal and Brindley's glands of the blood-sucking bug, Triatoma infestans, were identified by solid phase microextraction (SPME) and gas chromatography-mass spectrometry. Volatile compounds released by adult bugs during copulation or after mechanical disturbance were also characterized. Six compounds were identified and found consistently in all samples from metasternal glands. The most abundant were 3-pentanone, 2-methylbutanol, 3-pentanol, and an unidentified compound. The metasternal gland blends did not differ qualitatively between sexes. Compounds found in Brindley's glands were short chain acids, alcohols, esters, and a ketone with no qualitative differences between sexes. Isobutyric acid was the main component of this blend, and two new confirmed compounds were described as products of these glands: 2-butanone and 2-methylbutyric acid. 3-Pentanone was collected from the headspace over 33% of the copulating pairs of T. infestans. Volatiles found in the headspace of disturbed T. infestans adults included short-chain fatty acids, alcohols, esters, and ketones, with no qualitative differences between sexes. Both types of glands apparently discharge their contents after disturbance. However, most of the volatiles released by bugs after disturbance came from Brindley's glands. The locomotor activity of fourth instars increased significantly after stimulation with the odors emitted by disturbed adults, as compared with larvae stimulated by the odor of undisturbed adults or by clean air. We also studied the directional behavioral response of fifth instars to the disturbance scent in a locomotion compensator. Larvae exposed to volatiles released by disturbed adults walked away from the direction of the odor. The results suggest that this blend or part of it functions as an alarm pheromone for T. infestans. We suggest that the metasternal glands of this species are involved both in the sexual and the alarm contexts, and that the Brindley's glands probably have both alarm and defensive roles.
|
|
| 2. |
- El-Sayed, A. M., et al.
(författare)
-
Geographic variation in pheromone chemistry, antennal electrophysiology, and pheromone-mediated trap catch of North American populations of the obliquebanded leafroller
- 2003
-
Ingår i: Environmental Entomology. - 0046-225X .- 1938-2936. ; 32:3, s. 470-476
-
Tidskriftsartikel (refereegranskat)abstract
- The total and relative amounts of (Z)-11-tetradecenyl acetate (Z11-14:Ac), (E)-11-tetradecenyl acetate (E11-14:Ac), (Z)-11-tetradecen-1-ol (Z11-14:OH) and (Z)-11-tetradecenal (Z11-14:Al), and the EAG response of male antennae to these pheromone gland compounds were compared in laboratory reared Choristoneura rosaceana Harris (Lepidoptera: Tortricidae) from British Columbia, Michigan, Ontario, New York, and Quebec. A field trapping experiment was conducted in each of these locations to determine the effect of Z11-14:Al on the numbers of moths captured. The amount of each of the four pheromone-gland compounds declined successively in moths from British Columbia, Quebec, Ontario, Michigan, and New York. The relative amount of Z11-14:Ac was greatest in moths from New York and smallest in moths from Ontario, whereas the relative amount of E11-14:Ac was greatest in moths from Ontario and smallest in moths from British Columbia. Moths from Ontario, Quebec, British Columbia, Michigan, and New York contained decreasing relative amounts of Z11-14:OH and Z11-14:Al. There was a trend of increasing antenna] sensitivity to each of the four pheromone-gland compounds in moths from New York, Michigan, Ontario, Quebec, and British Columbia. The addition of 1% Z11:Al to a three compound blend of Z11-14:Ac, E11-14:Ac and Z11-14:OH (97:2:1) resulted in a >twofold increase in average trap catch in British Columbia, Ontario, and Quebec; this compound had no effect on trap catch in Michigan or New York.
|
|
| 3. |
- El-Sayed, A. M., et al.
(författare)
-
Relative attractiveness of (10E)-dodecen-1-yl acetate and (4E,10E)-dodecadien-1-yl acetate to male spotted tentiform leafminers Phyllonorycter blancardella (F.)
- 2004
-
Ingår i: Journal of Chemical Ecology. - : Springer. - 0098-0331 .- 1573-1561. ; 30:9, s. 1827-1838
-
Tidskriftsartikel (refereegranskat)abstract
- The antennae of male spotted tentiform leafminers, Phyllonorycter blancardella, from Ontario, Canada, exhibited similar electroantennogram responses when stimulated with E10-12:Ac or E4,E10-12:Ac. In field trapping experiments, E10-12:Ac was two-fold or more attractive than E4, E10-12:Ac, and E4,E10-12:Ac did not enhance the attractiveness of E10-12:Ac. E4,E10-12:Ac has not been identified in the pheromone of P. blancardella and it is hypothesized that the structural similarity of this compound and E10-12:Ac, the major pheromone compound of this species, may be responsible for the electrophysiological and behavioral responses to E4,E10-12:Ac. The possible reasons for the disparity between the results of our field trapping experiments and those carried out in Nova Scotia, Canada, and Massachusetts, USA., where E4,E10-12:Ac was found to be two to four times more attractive to P. blancardella than E10-12:Ac, are discussed.
|
|
| 4. |
|
|
| 5. |
- Baeckstroem, P., et al.
(författare)
-
Convenient Method for the Synthesis of Lineatin, a Pheromone Component of Trypodendron-Lineatum
- 1991
-
Ingår i: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 56:10, s. 3358-3362
-
Tidskriftsartikel (refereegranskat)abstract
- Synthesis of racemic lineatin (1), a pheromone component of Trypodendron lineatum, is described. Condensation of 5-methyl-5-hexen-2-one (2) and triethyl phosphonoacetate with LiN(SiMe3)2 gave esters 3, which upon hydrolysis gave acids 4a-f. The bicyclo[3.2.0] ring compounds 5 and 6 were obtained via an intramolecular [2 + 2] addition by refluxing underivatized carboxylic acids 4a-f with NaOAc and Ac2O. Compound 5 was isomerized to the thermodynamically more stable isomer 6 using a Pd/C catalyst activated with hydrogen. Reduction of 6 with LiAlH4 gave the endo and exo isomers 7a and 7b (4:1). Isolation of the alcohol 7a followed by acetylation gave 8. Subsequent oxidation with OsO4 and methylmorpholine N-oxide gave diol 9. Cleavage of 9 with H5IO6 in diethyl ether gave keto aldehyde 10, which was converted to keto acetal 11. Treatment of 11 with MeMgBr followed by acidic workup gave 1. The overall efficiency is approximately 20%.
|
|
| 6. |
|
|
| 7. |
- Blute, I, et al.
(författare)
-
Phase behaviour of alkyl glycerol ether surfactants
- 1998
-
Ingår i: Tenside Surfactants Detergents. - 0932-3414 .- 2195-8564. ; 35, s. 207-212
-
Tidskriftsartikel (refereegranskat)abstract
- In this paper the phase behaviour and physical properties of a series of alkyl (C6, C8, C12 and iso-C8) monoglycerol ethers and 2-hydroxyalkyl (C6, C8, C12) monoglycerol ethers are presented. The binary phase diagram for the surfactants shows very little dependence on temperature. It is shown that as the alkyl chain length increases the tendency to form lamellar liquid crystalline phases increases. The branched alkyl chain shows no formation of lamellar phase even at high concentrations of surfactant. The differences in phase behaviour between the surfactants is attributed to the variation in the critical packing parameter (CPP) of the surfactants. The presence of an additional hydroxyl group in the alkyl chain causes a temperature independent solubility behaviour. Ternary phase diagrams were prepared using dodecane as the oil phase. Hexyl glycerol ether was the only of the alkyl glycerol ethers which was sufficiently water soluble to determine the surface tension and CMC. The CMC was determined to 15 mM (and surface tension to 26 mN m-1).
|
|
| 8. |
- Bohman, Björn, et al.
(författare)
-
Practical one-pot stereospecific preparation of vicinal and 1,3-diols
- 2017
-
Ingår i: Tetrahedron Letters. - : Elsevier. - 0040-4039 .- 1359-8562. ; 58:1, s. 75-77
-
Tidskriftsartikel (refereegranskat)abstract
- A facile one-pot synthesis providing vicinal diols and 1,3-diols in >95% stereoisomeric purity from commercially available enantiopure hydroxy esters has been developed. The esters were reduced with DIBALH and alkylated in situ with 4-pentenylmagnesium bromide, which after workup generated the title diols as diastereomeric pairs. These pairs were easily separated by preparative chromatography, affording products with retained stereoisomeric purity from the starting materials. This method represents an expedient preparation of many common natural products, such as cerambycid beetle pheromones and intermediates towards bicyclic acetal bark beetle pheromones. (C) 2016 Elsevier Ltd. All rights reserved.
|
|
| 9. |
- Borg-Karlson, Anna-Karin, et al.
(författare)
-
Antifeedants in the feces of the pine weevil Hylobius abietis : Identification and biological activity
- 2006
-
Ingår i: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 0098-0331 .- 1573-1561. ; 32:5, s. 943-957
-
Tidskriftsartikel (refereegranskat)abstract
- Egg-laying females of the pine weevil, Hylobius abietis (L.), regularly deposit feces adjacent to each egg. Egg cavities are gnawed in the bark of roots of recently dead conifer trees. After egg deposition, the cavity is sealed by feces and a plug of bark fragments. Root bark containing egg cavities with feces is avoided as food by pine weevils, which indicates the presence of natural antifeedants. Here we present the first results of the isolation and chemical analyses of antifeedant compounds in the feces of H. abietis. In feeding bioassays, methanol extracts of the feces revealed strong antifeedant properties. Methanol extracts were fractionated by medium-pressure liquid chromatography and the antifeedant effects were mainly found in the fractions of highest polarity. Volatile compounds in the active fractions were identified by gas chromatography-mass spectrometry (GC-MS) and the nonvolatile compounds were characterized by pyrolysis-GC-MS. Based on mass spectra, a number of compounds with various chemical structures were selected to be tested for their antifeedant properties. Antifeedant effects were found among compounds apparently originating from lignin: e.g., a methylanisol, guaiacol, veratrol, dihydroxybenzenes, and dihydroconiferyl alcohol. A weak effect by fatty acid derivatives was found. The types of naturally occurring antifeedant compounds identified in this study may become useful for the protection of planted conifer seedlings against damage by H. abietis.
|
|
| 10. |
- Brown, Robert L., et al.
(författare)
-
Invasive Vespula Wasps Utilize Kairomones to Exploit Honeydew Produced by Sooty Scale Insects, Ultracoelostoma.
- 2015
-
Ingår i: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 0098-0331 .- 1573-1561. ; 41:11, s. 1018-1027
-
Tidskriftsartikel (refereegranskat)abstract
- Vespula wasps are widely distributed invasive alien species that are able to reach high population densities in the 1.2 M ha of beech forests (Fuscospora spp.) of New Zealand's South Island. These endemic temperate forests have an abundance of carbohydrate-rich honeydew produced by native scale insects (Ultracoelostoma spp.). A characteristic aroma is associated with the honeydew in beech forests, which we hypothesized is the signal used by wasps to harvest the vast resources previously exploited by birds and other insects. Volatile collections were taken of black beech tree trunks with honeydew and sooty mold present, and analyzed with a gas chromatograph-mass spectrometer. Eleven compounds (benzaldehyde, benzyl alcohol, 2-phenylethyl acetate, 2-phenylethanol, phenylacetaldehyde, methyl 2-phenylacetate, ethyl 2-phenylacetate, methyl salicylate, n-octanol, octan-3-ol, and 1-octen-3-ol) were positively identified from the headspace, and were shown to elicit an electrophysiological response from Vespula vulgaris worker antennae by using electroantennography (EAG). Field trials with delta traps individually baited with these compounds confirmed wasp attraction to 8 of the 11 compounds tested, with 2-phenylethyl acetate, methyl salicylate, and octan-3-ol capturing the same numbers of wasps as the control. In later trials, attraction to a 1:1 blend of benzaldehyde and n-octanol was significantly higher (45 %) than to any other treatment. Many of the chemicals identified are known to be associated with fermenting sugars, or with fungal aroma. Benzaldehyde and n-octanol are common compounds produced by many different species in nature. The ability to respond to generic signals emanating from sugar resources is likely to contribute to the success of V. vulgaris as an invasive species.
|
|
