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  • 1
    Electronic Resource
    Electronic Resource
    Tarsal secretion marks food sources in bumblebees (Hymenoptera: Apidae) (1991)
    Springer
    Chemoecology 2 (1991), S. 35-40 
    Details
    ISSN: 1423-0445
    Keywords: scent-marking ; tarsal glands ; hydrocarbons ; Insecta ; Hymenoptera ; Apidae ; Bombus terrestris
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary Scent-marking of artificial food sources by workers of the bumblebee,Bombus terrestris, was investigated. Odour marks deposited on artificial flowers were subsequently collected and chemically analysed. Alkanes and alkenes were identified as the main components. The behaviour mediating capacity of synthetic mixtures of the identified compounds was bioassayed using an artificial flower system. A mixture of alkanes and alkenes, close to natural proportions, released regular foraging behaviour. The reaction proved to be dose-dependent.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01240664
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  • 2
    Electronic Resource
    Electronic Resource
    Orientation ofRhizophagus grandis (Coleoptera: Rhizophagidae) to oxygenated monoterpenes in a species-specific predator-prey relationship (1992)
    Springer
    Chemoecology 3 (1992), S. 14-18 
    Details
    ISSN: 1423-0445
    Keywords: specificity ; predation ; long-range orientation ; windtunnel ; Coleoptera ; Rhizophagidae ; Scolytidae ; Rhizophagus grandis ; Dendroctonus micans
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary The predator,Rhizophagus grandis, is linked to its specific prey,Dendroctonus micans, by semiochemical signals regulating oviposition and long range orientation. A mixture of simple oxygenated monoterpenes [(−)—fenchone, (−)—pinocamphone, rac. camphor, terpinene-4-ol, borneol, fenchol and verbenone], identified from the frass ofD. micans has been found to be extremely active in a flight windtunnel as a long—range attractant for the predator. The mixture elicited 84 % of the response to larval frass of the prey. Excluding pinocamphone from the mixture did not influence its activity. Also, changing the absolute configurations of some of the components (fenchol, terpinene-4-ol and borneol) did not influence the predators' response. However, the addition of (−)—α-terpineol increased the attractivity of the synthetic blend to almost that of larval frass of the prey. Ecological implications of the identified semiochemicals and their use in pest management are discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01261451
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  • 3
    Electronic Resource
    Electronic Resource
    Male pheromone of swift moth,Hepialus hecta L. (Lepidoptera: Hepialidae) (1990)
    Springer
    Journal of chemical ecology 16 (1990), S. 3511-3521 
    Details
    ISSN: 1573-1561
    Keywords: Hepialus ; Lepidoptera ; Hepialidae ; swift moth ; pheromone ; dihydropyrone ; 2,9-dioxabicyclo[3.3.1] nonane ; behavior ; electrophysiology
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract (R)-6-Ethyl-2-methyl-2,3-dihydro-4H-pyran-4-one, (1R,3S,5R)-3-ethyl-1,8-dimethyl-2,9-dioxabicyclo[3.3. 1]non-7-ene, and (1R,3S,5R)-3-ethyl-1,8-dimethyl-2,9-dioxabicyclo[3.3.1]non-7-en-6-one represent the main components in the male pheromone of the swift moth,Hepialus hecta. The amounts of the three components were 40, 5, and 5 μg per male, respectively. Structure elucidation of the compounds was based on spectroscopic data as compared to synthetic reference samples. The absolute configurations were determined by gas chromatography on chiral stationary phases; optically active samples served as reference compounds. Electrophysiological and behavioral experiments with natural material and synthetic samples clearly showed the three heterocyclic compounds to act as pheromones. (E, E)-α-Farnesene represents the main component of the scent secretion of maleHepialus humuli.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00982114
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  • 4
    Electronic Resource
    Electronic Resource
    Andrena wilkella male bees discriminate between enantiomers of cephalic secretion components (1990)
    Springer
    Journal of chemical ecology 16 (1990), S. 429-441 
    Details
    ISSN: 1573-1561
    Keywords: Enantiomer discrimination ; male patrolling ; odor marking ; Hymenoptera ; Apoidea ; Andrena wilkella ; bee ; EAG ; spiroacetal ; absolute configuration ; 2,8-dimethyl-1,7-dioxaspiro[5.5]undecane
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Diastereomers of the spiroacetal, 2,8-dimethyl-1,7-dioxaspiro [5.5]undecane, represent main components of the cephalic secretion from males of the solitary bee,Andrena wilkella. The major compound proved to be of high enantiomeric purity, showing (2S,6R,8S) configuration. Only the naturally occurring enantiomer attracted patrolling males in the field; its antipode was behaviorally inactive and in a racemic mixture did not inhibit response. The (E,Z) diastereomers were also found to be almost inactive. EAG studies gave the same result as the behavioral tests. The biological function of the spiroacetal is discussed in view of the evolution of the mating behavior inA. wilkella.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01021775
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  • 5
    Electronic Resource
    Electronic Resource
    Electrophysiological and chemical analysis of sex pheromone communication system of the mottled umber,Erannis defoliaria (Lepidoptera: Geometridae) (1990)
    Springer
    Journal of chemical ecology 16 (1990), S. 1887-1897 
    Details
    ISSN: 1573-1561
    Keywords: Erannis defoliaria (Z,Z,Z)-3,6,9-nonadecatriene ; (Z,Z)-3,9-cis-6,7-epoxy-nonadecadiene ; sex pheromone ; identification ; electroantennogram ; single sensillum ; peripheral inhibitor ; Agriopis marginaria ; Colotois pennaria ; Lepidoptera ; Geometridae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract (Z,Z,Z)-3,6,9-nonadecatriene (Z3,Z6,Z9–19Hy) and (Z,Z)-3,9-cis-6,7-epoxy-nonadecadiene (Z3,Z9-cis-6,7-epo-19Hy) were identified in pheromone gland extracts from femaleErannis defoliaria. The two components were found in a 1∶3 ratio, with the main component,Z3,Z9-cis-6,7-epo-19Hy present at an amount of about 1.5 ng per female. The components were identified by means of gas chromatography-mass spectrometry, gas chromatography-electroantennography and gas chromatography-single sensillum recordings. Single sensillum measurements on the male antenna showed two physiological types of sensilla. One type was characterized by a large spike amplitude cell responding toZ3,Z9-cis-6,7-epoxy-19Hy and a small spike amplitude cell responding toZ3,Z6,Z9–19Hy. A second type responded only with a large spike amplitude cell to the epoxide, and this cell was inhibited by the triene. Of the two pheromone components, the epoxide gave the higher response in the EAG tests. Preliminary field tests support the identification of the pheromone components. The epoxide was also found to be present in the extract of the pheromone gland ofColotois pennaria, and males ofC. pennaria andAgriopis marginaria were trapped by the mixture of the identified compounds.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01020502
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  • 6
    Electronic Resource
    Electronic Resource
    Chemistry of fruit flies: Glandular secretion ofBactrocera (Polistomimetes) visenda (Hardy) (1992)
    Springer
    Journal of chemical ecology 18 (1992), S. 2169-2176 
    Details
    ISSN: 1573-1561
    Keywords: Bactrocera visenda ; Diptera ; Tephritidae ; fruit fly ; 3-methyl-2-butenyl acetate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The major component (〉90% of volatiles) of the male rectal glandular extract of the nonpest speciesBactrocera visenda (Hardy) is 3-methyl2-butenyl acetate, with minor components being the isomeric 3-methyl-3-butenyl acetate, the homologous esters, 3-methyl-2-butenyl propanoate and 3-methyl-2-butenyl formate, along with 3-methyl-2-buten-1-ol, 3-methyl-2-butenal, and 3-methylbutyl acetate. None of these compounds has been identified previously from aBactrocera species, supporting the view thatBactrocera visenda is taxonomically distant from otherBactrocera species identified from the Australian mainland. This collection of compounds adds to the known types utilized by dipteran species and emphasizes their extensive biosynthetic capability.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00984944
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  • 7
    Electronic Resource
    Electronic Resource
    Robber bees (Lestrimelitta limao) and their host chemical and visual cues in nest defense byTrigona (Tetragonisca) angustula (Apidae: Meliponinae) (1990)
    Springer
    Journal of chemical ecology 16 (1990), S. 631-641 
    Details
    ISSN: 1573-1561
    Keywords: Cephalic volatiles ; kairomone ; nest defense ; Lestrimelitta limao ; Trigona (Tetragonisca) angustula ; stingless bees ; Hymenoptera ; Meliponini ; Apidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The nest of the stingless bee,Trigona (Tetragonisca) angustula, is guarded by bees positioned in the nest entrance and others hovering in front of it. Hovering guard bees track returning foragers sideways along the last 10 cm in front of the nest, but intercept and incapacitate nest intruders by clinging with mandibles to wings and legs. When attacked by the cleptobiotic stingless beeLestrimelitta limao, the colony strengthens its aerial defense with hundreds of additional hoverers. To test our hypothesis that this reaction is due to interspecific chemical communication based on kairomone effects, we presented synthetic cephalic volatiles of both species at the nest entrance and counted the number of bees leaving the nest and taking up hovering positions. We conclude that guard bees recognizeL. limao by the major terpenoids of their volatile cephalic secretions, geranial, neral (=citral) and 6-methyl-5-hepten-2-one; other components may fine-tune this recognition. The effect of chemical stimuli is not significantly enhanced by combination with a dummy ofL. limao. Guard bees, we hypothesize, respond to this kairomone by secreting a species specific alarm pheromone; a major component of this pheromone, benzaldehyde, recruits additional bees to defend the nest.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01021793
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  • 8
    Electronic Resource
    Electronic Resource
    Novel Juvenoids of the 2-(4-hydroxybenzyl)cyclohexan-1-one Series (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 502-508 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A series of insect juvenile hormone analogs (juvenoids) was synthesized and studied. The basic skeleton of these juvenoids contains three rings and a short aliphatic subunit and bears two or three chiral centers (depending on the appropriate structure; see 6-9). The chiral center located in the 1,2-diphenoxypropane subunit has the configuration (RS), (R) (a series), or (S) (b series). The juvenoids were subjected to a biological screening, the preliminary results of which are briefly described.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19940770210
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  • 9
    Electronic Resource
    Electronic Resource
    Carbamate Series of Juvenoids: Variation of the O-alkyl substituent (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 561-568 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: By changing the O-alkyl substituents of the carbamate moiety of alkyl N-{2-{4-[(2-oxocyclohexyl)methyl]phenoxy}ethyl}carbamates and subsequent transformation of the oxo group in the cyclohexyl substituent, the juvenoids 1-20 were synthesized (Scheme). The methyl (1-4), propyl (9-12), isopropyl (13-16), and prop-2-ynylcarbamates (17-20) were subjected to biological screening on several non-related insect species (Tenebrio molitor, Galleria mellonella, Dysdercus cingulatus, and Pyrrhocoris apterus). Some of the juvenoids showed high biological activity and excellent selectivity with respect to target insect species (Table 2).
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19940770218
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  • 10
    Electronic Resource
    Electronic Resource
    Chemistry of fruit flies: Nature of glandular secretion and volatile emission ofBactrocera (bactrocera) cacuminatus (Héring) (1991)
    Springer
    Journal of chemical ecology 17 (1991), S. 485-495 
    Details
    ISSN: 1573-1561
    Keywords: Bactrocera cacuminatus ; Bactrocera oleae ; Diptera ; Tephritidae ; olive fly ; spiroacetal ; ketoalcohol ; chirality
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The major component of the rectal glandular extract and volatile emission of maleBactrocera cacuminatus is racemic 1,7-dioxaspiro[5.5]undecane. l-Hydroxy-5-nonanone as its open chain form, together with 6-n-butyl-3,4-dihydro-2H-pyran are minor components. 1,7-Dioxaspiro[5.5]undecan-4-ol is present at a low level and is shown to be exclusively the diastereomer with an equatorial hydroxy group by comparison with synthesized samples of both epimers. Examination of the trifiuoroacetate by chiral gas chromatography has established the (4S,6S) stereochemistry (ca. 80% ee). The presence of 1,7-dioxaspiro[5.5]undecan-3-ol, or its isomerization product, 1,6-dioxaspiro[4.5]decan-2-ylmethanol, could not be confirmed. Trapping of the volatiles released by sexually mature male flies at dusk revealed that a number of the glandular components described above are released at mating time. Reexamination of the glandular secretion of sexually mature female olive flies (B. oleae) has failed to confirm the presence of any 1,7-dioxaspiro[5.5]undecanols, with the only volatile component (other than fatty acids) being 1,7-dioxaspiro[5.5]undecane.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00994347
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