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  • Articles  (283)
  • Lepidoptera  (283)
  • Springer  (283)
  • Blackwell Publishing Ltd
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  • 1990-1994  (283)
  • 1950-1954
  • Chemistry and Pharmacology  (269)
  • Medicine  (14)
  • Energy, Environment Protection, Nuclear Power Engineering
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  • Articles  (283)
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  • 1
    Electronic Resource
    Electronic Resource
    From model to mimic: Age-dependent unpalatability in monarch butterflies (1994)
    Springer
    Cellular and molecular life sciences 50 (1994), S. 176-181 
    Details
    ISSN: 1420-9071
    Keywords: Cardiac glycoside loss ; Danaus plexippus ; aging ; breakdown of chemical defense ; three trophic level interactions ; automimicry ; Lepidoptera ; Asclepias
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract Monarch butterflies (Danaus plexippus) are unpalatable to various vertebrate predators because their larvae sequester bitter and emetic cardiac glycosides (CGs) from milkweed plants (Asclepias spp.). Here we show that the concentration of the defensive CGs decrease as individual butterflies age, regardless of the CGs' initial amounts or specific chemical structures. Consequently, individual monarch butterflies can change from being unpalatable models to palatable mimics during their lifetime. Since monarchs breed continuously over the spring and summer in North America, freshly emerged adult butterflies may serve as noxious models for older individuals which become automimics as they age.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01984960
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  • 2
    Electronic Resource
    Electronic Resource
    Evolution of behavioral responses to sex pheromone in mutant laboratory colonies ofTrichoplusia ni (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 231-238 
    Details
    ISSN: 1573-1561
    Keywords: Trichoplusia ni ; Lepidoptera ; Noctuidae ; sex pheromone ; behavior ; evolution ; sexual selection
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Male cabbage looper moths,Trichoplusia ni, from two colonies in which all females express an abnormal sex pheromone production phenotype were evaluated in a laboratory wind tunnel for upwind flight responses to the normal and abnormal sex pheromones. The abnormal sex pheromone blend consisted of 20 times as much (Z)-9-tetradecenyl acetate and 30-fold less (Z)-5-dodecenyl acetate compared to the normal pheromone blend. Initially, these males exhibited poor behavioral responses to the abnormal sex pheromone and maximum responses to the normal pheromone blend, indicating that there was no linkage between signal production and response. After 49 generations of laboratory rearing, males from the mutant colonies maintained good responses to the normal pheromone and increased their behavioral response to the abnormal sex pheromone to the same levels as for the normal pheromone. Over the same period, normal males maintained their preference for the normal pheromone. These results indicated that evolution had occurred in mutant colonies in favor of greater male responsiveness to the abnormal sex pheromone, resulting in the broadening of the response spectrum to pheromone blend ratios. This evolution presumably resulted from a mating advantage to those males that did not discriminate against mutant-type females in the mutant colonies.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02064433
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  • 3
    Electronic Resource
    Electronic Resource
    Oviposition stimulants inBarbarea vulgaris forPieris rapae andP. napi oleracea: isolation, identification and differential activity (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 423-438 
    Details
    ISSN: 1573-1561
    Keywords: Pieris rapae ; Pieris napi oleracea ; Lepidoptera ; Pieridae ; Barbarea vulgaris ; oviposition ; stimulants ; glucosinolates ; glucobarbarin ; glucobrassicin
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The closely related butterflies,Pieris rapae andP. napi oleracea, readily laid eggs onBarbarea vulgaris in greenhouse cages. When offered a choice between cabbage andB. vulgaris, P. rapae showed no preference, butP. napi oleracea preferredB. vulgaris. Bioassays of extracts ofB. vulgaris foliage revealed the presence of oviposition deterrent(s) in l-butanol extracts as well as stimulants in the postbutanol water extracts. However, the deterrent effect was apparently outweighed by the strong stimulatory effect in the whole plants. The postbutanol water extract was preferred over an equivalent cabbage extract by both species, but more significantly in the case ofP. napi oleracea. The stimulants were isolated by open column chromatography and HPLC, and the activity was associated with three glucosinolates.P. napi oleracea was more sensitive thanP. rapae to the natural concentration of compounds1 and3, whereas both species were strongly stimulated to oviposit by natural concentrations of compound2. Compounds1 and2 were identified as (2R)-glucobarbarin and (2S)-glucobarbarin, respectively, and3 was identified as glucobrassicin, on the basis of their UV, mass, and NMR spectra. When the pure compounds were tested at the same concentrations applied to bean plants, the (2R)-glucobarbarin at 0.2 mg/plant was preferred over a standard cabbage extract by both butterfly species. However, at a dose of 0.02 mg/plant,P. rapae preferred the cabbage extract whereasP. napi oleracea still preferred the (2R)-glucobarbarin. No such difference in response of the two species to the same two concentrations of (2S)-glucobarbarin was obtained. The results indicate a distinct difference in sensitivity of these butterflies to the epimers of glucobarbarin, and the differences in behavioral responses of the two butterfly species depend to a large extent on the concentration of stimulant present.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02064448
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  • 4
    Electronic Resource
    Electronic Resource
    Cardenolides as oviposition deterrents to twoPieris species: Structure-activity relationships (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 1039-1051 
    Details
    ISSN: 1573-1561
    Keywords: Pieris rapae ; Pieris napi oleracea ; Lepidoptera ; Pieridae ; oviposition ; deterrents ; cardenolides
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Oviposition responses ofPieris rapae andP. napi oleracea to 18 cardenolides were compared under the same conditions. Effects of different concentrations of selected cardenolides were also tested. Most of the compounds were deterrent to oviposition by both insects, but to significantly different degrees.P. rapae were strongly deterred by K-strophanthoside, K-strophanthin-β, cymarin, convallatoxin, oleandrin, erysimoside, erychroside, and gitoxigenin. The most deterrent compounds forP. napi oleracea were erychroside, cymarin, erysimoside, convallatoxin, and K-strophanthoside. Strophanthidin-based glycosides were more deterrent than digitoxigenin-based ones, and the number and type of sugar substitutions can have profound effects on activity. Both similarities and contrasts were found in responses ofP. rapae andP. napi oleracea to these cardenolides. Cymarin was equally deterrent to bothPieris species at all concentrations tested. However, when compared withP. rapae, P. napi oleracea was less sensitive to most of the cardenolides.P. napi oleracea was insensitive to K-strophanthin-β and oleandrin at 0.5 × 10−4 M, which were highly deterrent toP. rapae.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02059740
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  • 5
    Electronic Resource
    Electronic Resource
    Oxime ether analogs of sex pheromone components of turnip moth (Agrotis segetum Schiffermüller) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 1063-1073 
    Details
    ISSN: 1573-1561
    Keywords: Oxime ether ; NMR data ; pheromone mimics ; ESG studies ; structure-response relationships ; turnip moth ; Agrotis segetum Schiff. ; Lepidoptera ; Noctuidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Oxime ether analogs of sex pheromone components of the turnip moth (Agrotis segetum Schiff.) were synthesized by the acidolytic opening of cyclic enol ethers withO-alkyl hydroxylamine hydrochlorides. The compounds varying in chain lengths and in the position of the C=N double bond were studied by electrophysiological single sensillum recordings (electrosen-sillography: ESG). The ESG data indicate in general reduced receptor interaction of all analogs investigated in comparison with natural pheromone components of the turnip moth. The data also show that the grade of decrease of receptor interaction depends on specific structural changes within the molecule. The results demonstrate high complementary pheromone-receptor relationships, predominantly depending on the position of the unsaturated group in the chain, whereas analogs with other structural changes are still recognized as a pheromone-like compound by the receptor.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02059743
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  • 6
    Electronic Resource
    Electronic Resource
    Absorption and release of pheromone ofEpiphyas postvittana (Lepidoptera: Tortricidae) by apple leaves (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 1825-1841 
    Details
    ISSN: 1573-1561
    Keywords: Epiphyas postvittana ; Lepidoptera ; Tortricidae ; electroantennogram ; pheromone ; dispenser ; apple ; mating ; disruption ; atmospheric concentration
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The absorption and release of the pheromone ofEpiphyas postvititana (Lepidoptera: Tortricidae),E 11–14: OAc andE,E 9, 11–14: OAc (95:5) by apple leaves was studied using electroantennograms (EAG) and sticky traps baited with pheromone-treated leaves. Leaves exposed to an airstream containing pheromone reached a constant level of pheromone release within 3 min. Release occurred over a period greater than 24 hr, following removal of leaves from the pheromone-saturated environment. Pheromone-treated leaves were effective as lures in sticky traps for at least three nights, although the average catch per night decrease logarithmically with time. In the field, pheromone was detected by EAG on leaves harvested from up to 25 cm away from a central point source of pheromone. The shape of a surface representing equal pheromone re-release from leaves around a central point source was defined by interpolation from a three-dimensional transect. Leaves harvested from 5 cm under the dispensers showed the highest pheromone release rate. Leaves downwind of the dispensers also had higher release of pheromone. In a treated orchard, significantly higher EAG measurements were recorded in the rows of trees that contained dispensers, compared to grass interrows or untreated trees. The implications of foliar pheromone adsorption and release on atmospheric concentrations and insect behavior require further investigation.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02066225
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  • 7
    Electronic Resource
    Electronic Resource
    (E)-11,13-tetradecadienal: Major sex pheromone component of the eastern blackheaded budworm,Acleris variana (Fern.) (Lepidoptera: Tortricidae) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 1-8 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Tortricidae ; Acleris variana ; sex pheromone ; (E)-11,13-tetradecadienal
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract (E)-11,13-Tetradecadienal (E11,13–14:Ald) is the major sex pheromone component of the eastern blackheaded budworm (EBB),Acleris variana (Fern.). The compound was identified in female pheromone gland extracts by coupled gas chromatographic-electroantennographic detection (GC-EAD), coupled GC-mass spectrometry in selected ion monitoring mode, and retention index calculations of candidate pheromone components.E11,13–14:Ald alone as trap bait was very attractive to male EBB. Addition of the corresponding diene alcohol or acetate or both did not enhance attraction. (Z)-11,13-Tetradecadienal in binary combination with (E)-11,13–14:Ald neither enhanced nor reduced trap catches. Increasing the amounts of pheromone from 0.01 to 10 µg increased trap catches, but increase of pheromone quantity above 100 µg proportionately reduced attraction. Stabilization of slowly polymerizingE11,13–14:Ald and development of a sustained, adequate release rate is required for pheromone-based monitoring of EBB populations.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02065986
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  • 8
    Electronic Resource
    Electronic Resource
    Pheromone differences between sibling taxaDiachrysia chrysitis (linnaeus, 1758) andD. tutti (Kostrowicki, 1961) (Lepidoptera: Noctuidae) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 91-109 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Noctuidae ; Diachrysia chrysitis ; Diachrysia tutti ; pheromones ; sibling taxa ; electroantennographic responses ; biosynthesis ; cross-attraction
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The noctuid sibling taxaDiachrysia chrysitis s. str. andD. tutti, of yet uncertain taxonomic status, have previously been shown to possess differences in morphology and to be attracted to different mixtures of the two presumed pheromone components (Z)-5-decenyl acetate and (Z)-7-decenyl acetate. TypicalD. tutti males (clearly broken forewing marking) are known to respond to a 2: 100 mixture of the two isomers, whereasD. chrysitis males (unbroken marking) are attracted to a 100: 10 mixture. We investigated female pheromone production and male electroantennographic (EAG) response inDiachrysia families raised in the laboratory from field-collected gravid females. Extracts of individual females from typicalD. tutti andD. chrysitis families were subjected to gas chromatography with simultaneous flame ionization and electroantennographic detection. All females produced mixtures of Z5- and Z7-10:OAc, but femaleD. chrysitis produced predominantly Z5-10:OAc and the antennae of their brothers responded more strongly to the Z5 peak than to the Z7-10:OAc peak, whereas the opposite was true forD. tutti families. The pheromone components were shown to be biosynthesized from hexadecanoic and tetradecanoic acid, respectively by Z11-desaturation followed by chain shortening, reduction, and acetylation. The EAG responses of males trapped with the typicalD. tutti andD. chrysitis blends, as well as with an intermediate blend, were investigated. Males trapped with theD. tutti mixture almost exclusively had a clearly broken wing marking and showed strongest EAG response to Z7-10:OAc. The intermediate blend and theD. chrysitis mixture gave more mixed catches, but with a prevalence of males with an unbroken (or almost unbroken) wing marking and with a higher mean response to Z5-10:OAc. Some males with typicalD. tutti EAG responses were attracted in the field to theD. chrysitis pheromone. In the flight tunnel someD. chrysitis males were attracted also to theD. tutti mixture. This indicates that cross attraction may take place between the two taxa under natural conditions.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02065993
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  • 9
    Electronic Resource
    Electronic Resource
    Codling moth (Cydia pomonella): Disruptants of sex pheromonal communication (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 171-181 
    Details
    ISSN: 1573-1561
    Keywords: Codling moth ; Cydia pomonella ; Lepidoptera ; Tortricidae ; communication disruption ; mating disruption ; sex pheromone ; (E,E)-8,10-dodecadien-1-ol ; (E,Z)-8,10-dodecadien-1-ol ; (Z,E)-8,10-dodecadien-1-ol ; dodecan-1-ol ; tetradecan-1-ol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract In a small section of an apple orchard, six traps were placed each in control and test areas and baited with live virgin female codling moths. Gray elastomer septa were used to dispense communication disruptants around the traps. Dyed male codling moths were released in control and test areas, and the numbers of males captured in control and test traps were compared. In 1991, linear regression curves of percent communication disruption versus logarithm of dose were obtained for three compositions: (E,E)-8,10-dodecadien-1-ol, codlemone (1); codlemone + dodecan-1-ol + tetradecan-1-ol (2); and an equilibrium mixture of the four isomers of 8,10-dodecadien-1-ol (30, (61%EE, 14%ZE, 20%EZ, and 5%ZZ). All three regressions gaver 2 values greater than 0.90. At the 95% confidence limits, slopes and intercepts of compositions 1 and 2 were equivalent, and different from that of composition 3, which produced the greatest percentages of disruption at all doses. In 1992, five treatments were compared at a single dose: 1, 3, none (4), (Z,E)-8,10-dodecadien-1-ol (5), (E,Z)-8,10-dodecadien-1-ol (6). Compositions 5 and 6 gave the greatest and similar percentages of disruption and were different from codlemone (1) and 4 (95% confidence), but not from composition 3. Communication disruption produced by composition 3 was greater than (codlemone), which was greater than 4.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02065999
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  • 10
    Electronic Resource
    Electronic Resource
    Electrophysiological and field activity of halogenated analogs of (E,E)-8,10-dodecadien-1-ol, the main pheromone component, in codling moth (Cydia pomonella L.) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 489-503 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Tortricidae ; Cydia pomonella ; codling moth ; sex pheromone ; halogenated analogs ; isosteric replacements ; EAG ; single sensillum recording ; field trapping ; structure-activity relationship ; codlemone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Pest monitoring and control of the codling moth,Cydia pomonella L., have been developed using the main pheromone component of this species, (E,E)-8,10-dodecadienol (codlemone). However, the activity of codlemone is not satisfactory for pest control by mating disruption. Thus, we have synthesized halogenated analogs of codlemone to see if they could be used as new agents for pest control of the codling moth. Their biological activity was measured by electrophysiological techniques. In EAG screening, codlemone was the most active compound. F(10,11)-codlemone [(E,E)-10,11-difluoro-8,10-dodecadienol] and Cl-codlemone [(E,E)-11-chloro-8,10-undecadienol] elicited significant EAG responses, F(10,11)-codlemone triggering responses not significantly different from responses to codlemone. EAG cross-adaptation experiments and single sensillum recordings revealed that these compounds were detected by the same receptor neuron type as codlemone. No competitive inhibition with codlemone was observed from nonactive compounds. In field trapping, F(10,11)-codlemone and Cl-codlemone were more attractive to male codling moths than codlemone itself. Possible explanations of this activity are discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02059592
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  • 11
    Electronic Resource
    Electronic Resource
    Stratospheric ozone depletion and plantinsect interactions: Effects of UVB radiation on foliage quality ofCitrus jambhiri forTrichoplusia ni (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 525-539 
    Details
    ISSN: 1573-1561
    Keywords: Citrus jambhiri ; Trichoplusia ni ; Lepidoptera ; Noctuidae ; bergapten ; furanocoumarins ; phototoxins ; plant-herbivore interactions ; psoralen ; ultraviolet-B radiation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Projected decreases in stratospheric ozone may result in increases in shortwave ultraviolet (UVB) irradiation at the earth's surface. Furanocoumarins, phototoxic compounds found inCitrus jambhiri foliage, increase in concentration when these plants are grown under enhanced UVB. Survivorship schedules ofTrichoplusia ni (Lepidoptera: Noctuidae) caterpillars reared on plants in the presence and absence of enhanced UVB regimes differ significantly; larvae develop more slowly in early life when reared on plants exposed to increased UVB. This same developmental pattern is observed whenT. ni larvae are reared on artificial diets amended with ecologically appropriate amounts of furanocoumarins. Thus, anthropogenically derived changes in stratospheric ozone and concomitant changes in UV light quality at the earth's surface may influence ecological interactions between insects and their host plants by altering secondary metabolism and hence foliage quality for herbivores.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02059595
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  • 12
    Electronic Resource
    Electronic Resource
    Oxidative responses in soybean foliage to herbivory by bean leaf beetle and three-cornered alfalfa hopper (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 639-650 
    Details
    ISSN: 1573-1561
    Keywords: Soybean ; lipoxygenase ; peroxidase ; polyphenol oxidase ; trypsin inhibitor ; ascorbate oxidase ; oxidative stress ; Lepidoptera ; Noctuidae ; Helicoverpa zea ; corn earworm ; Cerotoma trifurcata ; bean leaf beetle ; Coleoptera ; Chrysomelidae ; Spissistilus festinus ; three-cornered alfalfa hopper ; Homoptera ; Membracidae ; induced resistance ; interspecific competition
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Variation in induced responses in soybean is shown to be dependent, in part, upon herbivore species. Herbivory by the phloem-feeding three-cornered alfalfa hopper caused increases in the activities of several oxidative enzymes including lipoxygenases, peroxidases, ascorbate oxidase, and polyphenol oxidase. Bean leaf beetle defoliation caused increased lipoxygenase activity, but had little effect upon peroxidase, polyphenol oxidase, ascorbate oxidase, or trypsin inhibitor levels in either field or greenhouse studies. In one field experiment, prior herbivory by the bean leaf beetle subsequently reduced the suitability of foliage to the corn earwormHelicoverpa zea. The contribution of these findings to emerging theories of insect-plant interactions is discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02059604
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  • 13
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    Female sex pheromone components of jasmine mothPalpita unionalis (Lepidoptera: Pyralidae) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 745-751 
    Details
    ISSN: 1573-1561
    Keywords: Sex pheromone ; (E)-11-hexadecenal ; (E)-11-hexadecen-1-yl acetate ; Palpita unionalis ; Lepidoptera ; Pyralidae ; Pyrustinae ; Anisodes sp. ; Geometridae ; jasmine moth
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract (E)-11-Hexadecenal and (E)-11-hexadecen-1-yl acetate were found in abdomen tip extracts from females of the jasmine mothPalpita unionalis (Hübn). The identification was based on capillary GC analyses, mass spectrometry, and laboratory and field tests. In laboratory bioassays, both components elicited a low level of upwind flight by males. The two components when tested separately in the field were inactive, but the blend of the two components at a ratio of (3:7) was highly attractive to males. Traps baited with 1 mg of the two-component blend were competitive to traps baited with five virgin females. The addition of Z isomers components reduced male capture.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02059610
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  • 14
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    Response of male eye-spotted bud moth,Spilonota ocellana (Lepidoptera: Tortricidae), to different pheromone blends in north America and The Netherlands (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 625-630 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Tortricidae ; Spilonota ocellana ; eye-spotted bud moth ; sex pheromone ; (Z)-8-tetradecenyl acetate and (Z)-8-tetradecenyl alcohol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Response of male eye-spotted bud moth,Spilonota ocellana (Denis and Schiffermüller), to different ratios of synthetic sex pheromone components, (Z)-8-tetradecenyl acetate (Z8-14:OAc) and (Z)-8-tetradecenyl alcohol (Z8-14:OH), were compared in four North American locations and in one location in The Netherlands. In British Columbia, Nova Scotia, Michigan, and The Netherlands, a 99:1 blend ofZ8-14:OAc andZ8-14:OH captured significantly more maleS. ocellana thanZ8-14:OAc alone or binary blends containing 10–50%Z8-14:OH. In Ontario, where population sizes were low compared to the other four locations, trends in trap catches were similar, and there was no indication that maleS. ocellana responded differently to the tested pheromone blends. A 99:1 blend ofZ8-14:OAc andZ8-14:OH should be most effective in pheromone-based control programs ofS. ocellana in North America and in The Netherlands. Our results confirm earlier studies that a 99:1 blend ofZ8-14:OAc andZ8-14:OH captures significantly more maleS. ocellana thanZ8-14:OAc alone. However, our finding that a 99:1 blend ofZ8-14:OAc andZ8-14:OH is significantly more attractive than binary blends containing 10–50%Z8-14:OH differs from previous findings in Germany and Switzerland.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02059602
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  • 15
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    Identification of olfactory cues used in host-plant finding by diamondback moth,Plutella xylostella (Lepidoptera: Plutellidae) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 1407-1427 
    Details
    ISSN: 1573-1561
    Keywords: Plutella xylostella ; Lepidoptera ; Plutellidae ; Brassica ; host plant attraction ; EAG ; bioassay ; host plant location ; plant volatiles ; mustard oils ; isothiocyanates
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Olfactory attraction of female diamondback moths (Plutella xylostella) to odors of intact and homogenized host plants, as well as individual compounds characteristic of host plants, were investigated by behavioral and electrophysiological methods. Moths were attracted to odors ofBrassica juncea andB. napus seedlings in a Y-tube bioassay. Solvent fractions of homogenizedB. juncea leaves were attractive to moths whether or not isothiocyanates (IC) were present. Moths were attracted in Y-tube bioassays and to field traps baited with individual ICs. Volatiles fromB. juncea andB. napus elicited an electroantennogram (EAG) response and were attractive in the Y-tube bioassay. Allyl IC was shown to be the attractive component in homogenized plant volatiles but was found to be virtually absent from intact plant volatiles. Gas chromatographic fractionation of intact plant volatiles revealed a terpene-containing fraction to be most attractive to the moths. We were unable to isolate individual attractive compounds from this fraction. Our results suggest that certain elements of this fraction, possibly in combination, are important olfactory cues for host-plant finding by the diamondback moth with mustard oils playing an important and possibly synergistic role, particularly when plants are damaged.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02059870
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  • 16
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    Squash leaf glandular trichome volatiles: Identification and influence on behavior of female pickleworm moth [Diaphania nitidalis (Stoll.)] (Lepidoptera: Pyralidae) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 2099-2109 
    Details
    ISSN: 1573-1561
    Keywords: Cucurbitaceae ; Cucurbita pepo ; Insecta ; Lepidoptera ; Pyralidae ; Diaphania ; oviposition ; nitidalis ; pickleworm moth ; egg laying ; visitations ; stimulation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Fourteen volatile compounds occurring in leaf trichomes of yellow squash (Cucurbita pepo L. cv. Early Prolific Straightneck) were identified. These compounds accounted for 83.5% of the volatile matrix. Ubiquitous constituents of the epidermis (myristic, palmitic, and stearic acids,n-tricosane, andn-pentacosane) accounted for 73.7%; these compounds were not bioassayed. The volatileso-,m-, andp-xylene, toluene, 2-heptanone, (R)-(+)- and (S)-(−)-limonene, and germacrene D were tested for their influence on attraction and oviposition by the pickleworm moth (Diaphania nitidalis Stoll.). No single compound, except germacrene D, was attractive. (R)-(+)-Limonene and 2-heptanone were weakly repellent. Mixtures of the highly volatile fractions were as attractive as volatiles emanating from whole, intact leaves. Oviposition levels on treated artificial sites corresponded with levels of visitation. Oviposition was significantly stimulated by “whole-leaf” volatiles, and (S)-(−)-limonene caused a slight but significant reduction.
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    Attacus atlas caterpillars (Lep., Saturniidae) spray an irritant secretion from defensive glands (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 2127-2138 
    Details
    ISSN: 1573-1561
    Keywords: Attacus atlas ; biogenic amines ; chemical defense ; defensive glands of caterpillars ; histamine ; Lepidoptera ; Saturniidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The ability ofAttacus atlas caterpillars to spray a defensive secretion seems to be due to the fine structure of the integumental glands that produce it. The giant gland cells are fixed to stable cuticular rings surrounding the gland openings and tightly closed by cuticular lids. Probably by increasing hemolymph pressure, the lids are blasted off and the secretion spouts out. The fluid contains several aromatics, biogenic amines (e.g., acetylcholine, histamine), glycerol, and trehalose and exhibits tyrosinase activity. Deterrent effects of caterpillar secretion and hemolymph on predatory ants could be shown. Presumably the spraying process serves to apply the secretion to sensitive sites of vertebrate target organisms.
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    URL: http://dx.doi.org/10.1007/BF02066249
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    Induction of parasitoid attracting synomone in brussels sprouts plants by feeding ofPieris brassicae larvae: Role of mechanical damage and herbivore elicitor (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 2229-2247 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Pieridae ; Hymenoptera ; Braconidae ; cabbage ; Brussels sprouts ; behavior ; tritrophic interactions ; green-leaf volatiles ; herbivore-induced synomones ; elicitor ; caterpillar regurgitant ; Brassica oleracea ; Pieris brassicae ; Cotesia glomerata ; parasitoid ; wasp
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Induction of plant defense in response to herbivory includes the emission of synomones that attract the natural enemies of herbivores. We investigated whether mechanical damage to Brussels sprouts leaves (Brassica oleracea var.gemmifera) is sufficient to obtain attraction of the parasitoidCotesia glomerata or whether feeding byPieris brassicae caterpillars elicits the release of synomones not produced by mechanically damaged leaves. The response of the parasitoidCotesia glomerata to different types of simulated herbivory was observed. Flight-chamber dual-choice tests showed that mechanically damaged cabbage leaves were less attractive than herbivore-damaged leaves and mechanically damaged leaves treated with larval regurgitant. Chemical analysis of the headspace of undamaged, artificially damaged, caterpillar-infested, and caterpillar regurgitant-treated leaves showed that the plant responds to damage with an increased release of volatiles. Greenleaf volatiles and several terpenoids are the major components of cabbage leaf headspace. Terpenoids are emitted in analogous amounts in all treatments, including undamaged leaves. On the other hand, if the plant is infested by caterpillars or if caterpillar regurgitant is applied to damaged leaves, the emission of green-leaf volatiles is highly enhanced. Our data are in contrast with the induction of more specific synomones in other plant species, such as Lima bean and corn.
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    URL: http://dx.doi.org/10.1007/BF02033199
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  • 19
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    Different feeding and gustatory responses to ecdysone and 20-hydroxyecdysone by larvae of the silkworm,Bombyx mori (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 125-133 
    Details
    ISSN: 1573-1561
    Keywords: Bombyx mori ; Lepidoptera ; Bombiridae ; silkworm ; larvae ; ecdysone ; 20-hydroxyecdysone ; feeding behavior ; electrophysiology ; sensilla response ; chemoreceptors
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The feeding and gustatory responses to ecdysone and 20-hydroxyecdysone were investigated in the silkworm,Bombyx mori. 20-Hydroxyecdysone reduced feeding response strongly in fourth- and fifth-instar larvae, whereas ecdysone had no effect on feeding response. 20-Hydroxyecdysone stimulated the R receptor, the receptor to feeding deterrents, to a great degree. By contrast, ecdysone was much less effective for stimulating the R receptor. These results indicate that ecdysone and 20-hydroxyecdysone have different effects on feeding response due to different interactions with mouthpart chemoreceptors.
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  • 20
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    Induced resistance in soybean toHelicoverpa zea: Role of plant protein quality (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 183-198 
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    ISSN: 1573-1561
    Keywords: Induced resistance ; protein quality ; Helicoverpa zea ; soybean ; Glycine max ; protease inhibitor ; lipoxygenase ; Lepidoptera ; noctuidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Resistance in soybean toHelicoverpa zea is comprised of both constitutive and inducible factors. In this study, we investigated the induction of resistance byH. zea in both greenhouse and field studies. In a greenhouse experiment, fourth-instarH. zea growth rates were reduced by 39% after 24 hr feeding and by 27% after 48 hr when larvae fed on previously wounded V3 foliage (cv. Forrest) compared with undamaged foliage. In a field study, the weight gain by larvae was more than 52% greater when larvae fed for 72 hr on undamaged R2/R3 soybean plants (cv. Braxton) compared to those that fed on previously wounded plants. A significant component of the induced resistance is due to a decline in the nutritional quality of foliar protein following foliar damage byH. zea. Foliar protein was extracted from damaged and undamaged foliage and incorporated into artificial diets. Larval growth was reduced 26% after four days and 49% after seven days on diets containing protein from damaged plants compared to larvae feeding on foliar protein from undamaged plants. Chemical analyses of protein quality also indicated a decline in quality in damaged plants compared to unwounded plants. Increases in lipoxygenase activity (53%), lipid peroxidation products (20%), and trypsin inhibitor content (34%) were observed in protein from wounded plants. Moreover, a 5.9% loss in free amines and 19% loss in total thiols occurred in protein from wounded plants. Larval feeding causes a significant increase in foliar lipoxygenase activity that varied among genotypes. Lipoxygenase isozymes were measured at pH 5.5, pH 7.0, and pH 8.5 in V3 stage plants of Forrest, Hark, D75-1069, and PI 417061 genotypes. Lipoxygenase activity in each genotype was significantly increased after 72 hr of larval feeding at each pH level tested, with the exception of lipoxygenase isozymes at pH 5.5 in genotype PI 417061. Larval feeding on R2/R3 stage plants (field-grown cv. Braxton) for six days also increased foliar lipoxygenase activity.
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    Sex pheromone components of the spring hemlock looper,Lambdina athasaria (Walker) (Lepidoptera: Geometridae) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 2501-2511 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Geometridae ; Lambdina athasaria ; Lambdina fiscellaria fiscellaria ; Lambdina fiscellaria lugubrosa ; sex pheromone ; synergism ; 7,11-dimethylheptadecane ; 7-methylheptadecane ; 5,11-dimethylheptadecane
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Two methylated hydrocarbons, 7-methylheptadecane (7) and 7,11-dimethylheptadecane (7,11), are female sex pheromone components of the spring hemlock looper (SHL),Lambdina athasaria (Walker). Compounds extracted from female pheromone glands were identified by coupled gas chromatographic-electroantennographic detection (GC-EAD) and coupled GC-mass spectrometry (GC-MS) in selected ion monitoring mode. In field trapping experiments, (7) and (7,11) by themselves were behaviorally inactive, but in combination attracted numerous male moths. (5,11)-Dimethylheptadecane (5,11) was detected in female SHL pheromone gland extracts, but did not enhance attraction to the binary blend of (7) and (7,11). The sex pheromone of SHL is related to that of congeneric eastern hemlock looper (EHL),Lambdina fiscellaria fiscellaria (Guen.) [(5,11) and 2,5-dimethylheptadecane (2,5)] and western hemlock looper (WHL),L.f. lugubrosa (Hulst) [(5,11), (2,5) and (7)]. Specificity of the pheromonal blend, spatial separation of coseasonal EHL and WHL, and temporal separation of sympatric EHL and SHL contribute to reproductive isolation.
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    URL: http://dx.doi.org/10.1007/BF02036187
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    Sex pheromone of cranberry fruitworm,Acrobasis vaccinii riley (Lepidoptera: Pyralidae) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 3269-3279 
    Details
    ISSN: 1573-1561
    Keywords: Cranberry fruitworm ; Lepidoptera ; Pyralidae ; Acrobasis vaccinii ; sex pheromone ; (E,Z)-8,10-pentadecadien-l-ol acetate ; (E)-9-pentadecen-l-ol acetate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The following compounds and (approximate ratios) were identified in sex pheromone gland extracts of femaleAcrobasis vaccinii Riley by comparison of gas chromatography-mass spectrometric traces with those of synthetic standards: (E,Z)-, (Z,E)-, (Z,Z), and (E,E)-8, 10-pentadecadien-l-ol acetates (100:1:2:12), a dodecen-l-ol acetate (8), (Z)-8-, (Z)-9-, and (E)-9-pentadecen-l-ol acetates (3:23:4), two heptadecen-l-ol acetates (4:4), tetradecyl, pentadecyl, hexadecyl, and heptadecyl acetates (3:15:10:8), dodecan-l-ol (6), tetradecan-l-ol (5), and hexadecan-l-ol (23). The amount of (E,Z)-8, 10-pentadecadien-l-ol acetate (E8,Z10–15:Ac) in the extract was about 0.5 ng/female. Electroantennographic analysis of gas chromatographic fractions of female sex pheromone gland extract showed that the fraction containingE8,Z10–15:Ac elicited the greatest response. Alone,E8,Z10–15:Ac failed to elicit upwind flight of males in flight-tunnel tests, and traps baited with it did not catch males in field experiments. WhenE8,Z10–15:Ac was combined with (E)-9-pentadecen-l-ol acetate (100:4), male upwind flight response in flight-tunnel tests was equivalent to those obtained with extract of female sex pheromone glands (synthetic, 62%; natural, 51%), but the percent of males flying upwind that contacted the source was lower (synthetic, 47%; natural, 88%). The lower percent of source contact elicited by the synthetic pheromone could be a result of the difference in isomer ratios of 8,10–15:Ac in the natural and synthetic pheromone or could indicate that the synthetic pheromone is incomplete. Traps baited with the 100:4 combination caught large numbers of males in field experiments.
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    Role of Douglas fir (Pseudotsuga menziesii) carbohydrates in resistance to budworm (Choristoneura occidentalis) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 395-405 
    Details
    ISSN: 1573-1561
    Keywords: Douglas fir ; Pseudotsuga menziesii ; galactose ; terpenes ; sugars ; carbohydrates ; resistance ; western spruce budworm ; mortality ; Choristoneura occidentalis ; Lepidoptera ; Tortricidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The current year's growth of Douglas fir contains galactose, unusual in that this carbohydrate makes up 78.7% of the total carbohydrate fraction. An agar diet study was undertaken to determine the effects of galactose, other carbohydrates, and terpenes on western spruce budworm larval mortality, growth rate, and adult biomas production. All concentrations of the carbohydrates and terpenes tested, as well as other mineral elements not tested, were typical of the current year's foliage of Douglas fir. In experiment I, the diet containing 5.61% total carbohydrate did not significantly affect larval mortality when compared to the control diet. However, diets containing 9.45% and 15% total carbohydrate concentrations significantly increased larval mortality 64% and 96.1%, respectively, when compared to the control. Also in experiment I, terpenes alone (78.9% morality) and terpenes in combination with 9.45% and 15% total carbohydrates significantly increased larval mortality (97.2% and 100%, respectively) when compared to mortality on the control diet (44%). To determine which carbohydrate was causing the adverse effect, 6% glucose, 6% fructose, and 6% galactose were placed individually and in combination with terpenes in diets in experiment II. The 6% galactose diet significantly increased larval mortality and reduced growth rate when compared to the control, glucose, and fructose diets. Glucose resulted in 16% less larval mortality, significantly enhanced female larval growth rate and pupal weight, but did not affect male larval growth rate and pupal weight, when compared to the control. Fructose resulted in a significant decrease in larval mortality and a general trend of enhanced female and male larval growth rate and pupal weight. Larval mortality on terpenes alone was not significantly different from the control, but terpenes with 6% galactose increased larval mortality and decreased female and male growth rate and pupal weight significantly when compared to glucose-terpene and fructose-terpene diets. No significant interactions were found between carbohydrates and terpenes in either experiment.
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    Field tests of syntheticManduca sexta sex pheromone (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 579-591 
    Details
    ISSN: 1573-1561
    Keywords: Aldehydes ; formulation ; 10,12-hexadecadienal ; 10,12,14-hexadecatrienal ; moth ; Manduca sexta ; Lepidoptera ; Sphingidae ; tobacco hornworm ; trapping
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract In field experiments traps were baited with live females or with a two-, four-, or eight-component blend of the 16-carbon aldehydes previously identified as components of the sex pheromone emitted by femaleManduca sexta moths. The blends were formulated on rubber septa. Traps baited with a blend of all eight aldehydes captured moreM. sexta males than any other treatment. Septa loaded with 600 μg of the eight-component blend were attractive to males for about seven days in the field. Septa loaded with the eight-component blend and stored in a refrigerator at 4°C for a year released the conjugated diene and triene aldehydes at the same rate as freshly prepared septa and were equally attractive in the field.
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    Mating disruption of pea mothCydia nigricana F. (lepidoptera: Tortricidae) by a repellent blend of sex pheromone and attraction inhibitors (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 871-887 
    Details
    ISSN: 1573-1561
    Keywords: Sex pheromone ; attraction inhibitor ; behavioral antagonist ; mating disruption ; air permeation ; field EAG ; Cydia nigricana ; Tortricidae ; Lepidoptera ; pea moth ; (E,E)-8,10-dodecadien-1-yl acetate
    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 polyethylene dispensers at a rate of 30 g/ha and 600 dispensers/ha in a 0.6-ha pea field. The release rate ofE8,E10–12: Ac was 140 mg/ha/day after six days, and 82 mg/ha/day after 20 days. Aerial concentrations ofE8,E10–12: Ac, as measured by a portable EAG apparatus, ranged from 2 ± 2 to 7 ± 3 ng/m3. The antennal signal was high and rather constant within pea canopy, but was lower and fluctuated strongly above canopy. Initially, 〉99% isomerically pureE8,E10–12: Ac was released, and male moths were attracted to dispensers. After nine days, isomeric blend composition had equilibrated to approx. 92%E8,E10–12: Ac and 8% of the inhibitory isomersE,Z-,Z,E-, andZ8,Z10–12: Ac. Males were then repelled from the pheromone-permeated field. Traps baited with 100 µgE8,E10–12: Ac caught 258 ± 133C. nigricana males/trap in the control, but no males at all in the disruption field.
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    Influence of cnicin, a sesquiterpene lactone ofCentaurea maculosa (Asteraceae), on specialist and generalist insect herbivores (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 929-942 
    Details
    ISSN: 1573-1561
    Keywords: Centaurea maculosa ; sesquiterpene lactone ; cnicin ; host-plant selection ; oviposition behavior ; antifeedant ; attractant ; Spodoptera littoralis ; Agapeta zoegana ; Stenodes straminea ; Pterolonche inspersa ; Lepidoptera ; Noctuidae ; Cochylidae ; Pterolonchidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The sesquiterpene lactone cnicin was extracted fromCentaurea maculosa andCentaurea vallesiaca. We examined its effects on the ovipositional response and larval development of generalist and specialist insect herbivores associated withC. maculosa. For the oviposition trials, three plant species (C. maculosa, Achillea millefolium, andCichorium intybus), half of which were sprayed with 3% of cnicin, were exposed to the specialist mothsStenodes straminea, Agapeta zoegana, andPterolonche inspersa in field cages. All three species significantly preferredC. maculosa to other plants andP. inspersa significantly preferred cnicin-sprayed plants to untreated plants for oviposition. Tested over all species, cnicin significantly increased the number of eggs laid on a given plant. A larval diet test examined the toxicity of cnicin for larvae of the generalist noctuid mothSpodoptera littoralis. Cnicin concentrations of 3% and 6% were lethal and 1% and 0.5% seriously inhibited growth and development. The larvae of theC. maculosa specialistStenodes straminea survived at 6% cnicin, but none of the pupae hatched.Agapeta zoegana was able to survive at 1% and 3% cnicin. Both specialists had difficulties with the artificial diet, but weight increase and survival was not further reduced when cnicin was present compared with on the control diet. In conclusion, cnicin influenced host recognition by the specialist species, and larvae of the generalist did not survive on natural levels of cnicin. Growth and survival of the specialist were not influenced by cnicin but were considerably hampered on artificial diet.
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    Relative activities of glucosinolates as oviposition stimulants forPieris rapae andP. napi oleracea (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 1025-1037 
    Details
    ISSN: 1573-1561
    Keywords: Pieris rapae ; Pieris napi oleracea ; Lepidoptera ; Pieridae ; oviposition ; stimulants ; glucosinolates
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The relative activities of 10 glucosinolates in stimulating oviposition byP. rapae andP. napi oleracea were compared under the same conditions. When tested at the same concentration, the structurally different glucosinolates stimulated both butterfly species to widely varying degrees. In most cases,P. rapae was more sensitive to aromatic and indole glucosinolates than to aliphatic representatives. This species responded even less to alkyl thio and sulfinyl glucosinolates. However,P. napi oleracea responded strongly to these aliphatic and sulfur-containing members of the group, and the relative activities of aromatic and aliphatic glucosinolates did not show a clear pattern for this species.P. napi oleracea was much more sensitive to low concentrations of sinigrin than wasP. rapae. The threshold concentration for response ofP. napi oleracea to sinigrin was 10−8 M, which was 100 times lower than forP. rapae, butP. rapae was more sensitive thanP. napi oleracea to changes in glucosinolate concentrations. For bothPieris species, an optimal concentration was reached, above which the response remained constant or tended to decrease.
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    Plant-natural enemy association in the tritrophic system,Cotesia rubecula-Pieris rapae-brassiceae (cruciferae): I. Sources of infochemicals (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 1725-1734 
    Details
    ISSN: 1573-1561
    Keywords: Cotesia rubecula ; Hymenoptera ; Braconidae ; Lepidoptera ; Pieridae ; Plutellidae ; Pieris rapae ; Brassica oleracea ; Plutella xylostella ; Phaselus vulgaris ; Geranium molle ; tritrophic interactions ; infochemicals ; volatiles
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The role of airborne infochemicals in host selection by the parasitoidCotesia rubecula (Marshal) (Hymenoptera: Braconidae) was examined in a wind tunnel. To elucidate the role of volatile chemicals in attractingC. rubecula to cabbage infested by the host [Pieris rapae L. (Lepidoptera: Pieridae)], the potential sources of volatiles related toP. rapae infestation on cabbage were tested individually. The responses of females to nonhost plant species, bean and geranium, as well as to frass of a nonhost lepidopteran were also examined.C. rubecula was attracted to cabbage previously infested byP. rapae and to frass and regurgitate ofP. rapae. No attraction was observed to larvae ofP. rapae alone. Females were also attracted to mechanically damaged cabbage, cabbage previously infested byPlutella xylostella L. (Lepidoptera: Plutellidae) (a nonhost lepidopteran herbivore), and cabbage previously infested by snails (a nonhost, noninsect herbivore). Intact cabbage, bean, and geranium plants elicited no attraction. A low frequency of attraction was observed to mechanically damaged bean and geranium. Attraction was also observed to frass ofP. xylostella. Volatiles from cabbage related to damage, and volatiles from frass and regurgitate of the host seem to play an important role in guidingC. rubecula to plants infested by its host.
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    Plant-natural enemy association in the tritrophic systemCotesia rubecula-Pieris rapae-brassicaceae (cruciferae): II. Preference ofC. rubecula for landing and searching (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 1735-1748 
    Details
    ISSN: 1573-1561
    Keywords: Cotesia rubecula ; Hymenoptera ; Braconidae ; Lepidoptera ; Pieridae ; Plutellidae ; Pieris rapae ; Plutella xylostella ; Helix aspera ; Brassica oleracea ; Phaseolus vulgaris ; tritrophic interactions ; synomones ; infochemicals
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The responses of the parasitoidCotesia rubecula to differently damaged cabbages were recorded during a series of choice tests. To determine if flyingC. rubecula can discriminate differences in the blend of volatiles emitted by cabbages damaged by different causes and how plant volatiles released from a distant source affect the searching behavior ofC. rubecula once searching on a plant, wasps were presented with a choice of plants located one behind the other and separated by a distance of 15 cm. The sources of damage were: cabbage damaged by the host (Pieris rapae), by a nonhost lepidopteran herbivore (Plutella xylostella), by a nonhost, noninsect herbivore (snail), and by mechanical means. The results showed that the site of first landing and the time spent searching on the leaves was influenced by the type of damage inflicted on plants. Wasps preferred to land on cabbages damaged by host and nonhost species of Lepidoptera over those damaged by snails and mechanical means. No preference was observed for first landing between cabbages damaged by the two species of Lepidoptera or between cabbages damaged by snails and mechanical means. Cabbage damaged byP. rapae was searched most intensively, followed by cabbage damaged byP. xylostella, cabbage damaged by snails, and cabbage damaged by mechanical means.C. rubecula differentiates between the volatile blends emitted by differently damaged cabbages, and it is attracted to volatiles related to recent lepidopteran damage. Wasps searched longer on freshly damaged than on leaves with older damage.
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    Chemical composition of North American bee propolis and biological activity towards larvae of greater wax moth (Lepidoptera: Pyralidae) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 1783-1791 
    Details
    ISSN: 1573-1561
    Keywords: Galleria mellonella ; Apis mellifera ; Pyralidae ; Apidae ; Lepidoptera ; Hymenoptera ; greater wax moth ; honeybee ; propolis ; plant resins ; phenolics
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Bee propolis is a sticky amalgamation of plant resins collected by honeybees (Apis mellifera L.) and used in the hive for filling cracks and repairing combs. Propolis contains a diversity of compounds of plant origin, and is reported to have medicinal, antimicrobial, insecticidal, and phytotoxic properties. We examined the physical and chemical composition of North American samples of bee propolis from several sites in North America and tested for bioactivity against larvae of the greater wax moth (Galleria mellonella L.), a common apiary pest. The amount of methanol-extractable resin in samples from Ohio and Georgia ranged from 24% to 79% by weight. Propolis collected from hives in Ohio was more chemically diverse (over 30 compounds detected by paper chromatography) than material from south Georgia (fewer than 10 major compounds) and contained a lower proportion of methanol-insoluble beeswax. The paper chromatographic surveys revealed little variation in the chemical profile of specific hives over a six-month period and no differences between propolis from adjacent hives. Four flavonoids were identified from propolis collected in Ohio: kaempferol, galangin, 3,3′-dimethoxyquercetin and 3-methoxykaempferol. When mixed into artificial diet, fractionated propolis reduced larval growth of the greater wax moth, but not dramatically. An array of phenolics reported from propolis (caffeic acid, chrysin, ferulic acid, galangin, kaempferol, and quercetin) were bioassayed individually for effects on larvae, but none reduced larval growth at the concentrations tested, suggesting that wax moths are tolerant of some phenolics in their diet.
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    Plant-natural enemy association in tritrophic system,Cotesia rubecula-Pieris rapae-brassicaceae (Cruciferae). III: Collection and identification of plant and frass volatiles (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 1955-1967 
    Details
    ISSN: 1573-1561
    Keywords: Pieris rapae ; Lepidoptera ; Pieridae ; Plutellidae ; Plutella xylostella ; Cotesia rubecula ; Hymenoptera ; Braconidae ; Brassica oleracea capitata ; infochemicals ; plant volatiles
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract To elucidate the identity of the volatile compounds that could be involved in the searching behavior of the parasitoidCotesia rubecula Marshall (Hymenoptera: Braconidae), the volatiles released by cabbage and frass of Lepidoptera feeding on cabbage were collected and analyzed using a gas chromatograph-mass spectrometer. The volatiles emitted by intact cabbage were α-pinene, β-pinene, myrcene, 1,8-cineole,n-hexyl acetate,cis-3-hexen-1-yl acetate, and dimethyl trisulfide. Mechanical damage on an intact plant induced the release of two more compounds,trans-2-hexenal and 1-methoxy-3-methylene-2-pentanone. Current feeding by larvae ofPieris rapae L. (Pieridae) induced the plant to release all the compounds released after mechanical damage and additionally 4-methyl-3-pentenal and allyl isothiocyanate. Current feeding by larvae ofPlutella xylostella L. (Plutellidae) induced the plant to release all the compounds present after mechanical damage and additionally allyl isothiocyanate. The volatiles emitted after feeding by the lepidopterans had ceased were the same as those emitted by cabbage damaged by mechanical means. The blend of volatiles emitted by frass was comprised of plant chemicals, mainly sulfur compounds. Frass ofP. rapae emitted allyl isothiocyanate, methyl isothiocyanate, methyl propyl sulfide, dimethyl trisulfide,S-methyl methane thiosulfinate, 4-methyl-3-pentenal,trans-2-hexenal, and 2,3-dihydro-4-methyl furan. Frass ofP. xylostella emitted only dimethyl trisulfide andS-methyl methane thiosulfinate. The blend of volatiles emitted by frass is herbivore-species specific.
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    Tannin sensitivity in larvae ofMalacosoma disstria (Lepidoptera): Roles of the peritrophic envelope and midgut oxidation (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 1985-2001 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Lasiocampidae ; Malacosoma disstria ; Orgyia leucostigma ; larva ; tannin ; tannic acid ; peritrophic membrane ; oxidation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Final-instarMalacosoma disstria fed artificial diets containing tannic acid develop lethal pupal deformities. We examined some of the factors potentially underlying tannin sensitivity in this species, including the permeability of the peritrophic envelope to tannic acid and the chemical fate of tannic acid in the gut. Tannic acid does not penetrate the peritrophic envelope ofM. disstria, demonstrating that the containment of tannic acid within the endoperitrophic space is not sufficient to protect an insect herbivore from the adverse effects of ingested tannins. Ingested tannic acid undergoes extensive chemical modification in the midgut. Only 19–21 % of the high molecular weight components of the tannic acid ingested was recovered in the frass. Of two possible chemical fates of ingested tannic acid, oxidation is the predominant chemical transformation, whereas little hydrolysis occurs. Measurements of gut redox parameters showed that conditions in the midgut favor the oxidation of phenols. However, similar conditions occur in the midguts ofOrgyia leucostigma, in which no oxidation occurs. Therefore, oxidizing gut redox conditions do not necessarily lead to polyphenol oxidation in lepidopteran larvae. We conclude that the sensitivity ofM. disstria to ingested tannins is a consequence of their oxidation in the midgut.
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    Analysis, isolation and insecticidal activity of linear furanocoumarins and other coumarin derivatives fromPeucedanum (Apiaceae: Apioideae) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 2035-2054 
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    ISSN: 1573-1561
    Keywords: Apiaceae ; Peucedanum ; Lepidoptera ; Noctuidae ; Spodoptera littoralis ; HPLC ; preparative isolation ; furocoumarins ; furanocoumarins ; pyranocoumarins ; growth inhibition ; dietary utilization ; plant chemical diversity
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Peucedanum arenarium Waldst. & Kit.,P. austriacum (Jacq.) Koch,P. coriaceum Reichenb.,P. longifolium Waldst. & Kit,P. officinale L.,P. oreoselinum (L.) Moench,P. ostruthium L., andP. palustre (L.) Moench accumulate different structural types of coumarins including simple coumarins, linear furanocoumarins, linear dihydropyranocoumarins, angular dihydrofuranocoumarins and angular dihydropyranocoumarins. Linear furanocoumarins, known for various biological activities, include some well-known antifeedants, such as bergapten, isopimpinellin, and xanthotoxin. The aim of this investigation was to screen the diverse coumarins fromPeucedanum for insecticidal activity. LC was used to analyze and isolate coumarins for the bioassays. A growth inhibition bioassay with 17 derivatives, comprising all structural types fromPeucedanum, carried out withSpodoptera littoralis (Boisduval) (Lepidoptera: Noctuidae) as test organism, indicated the majority of the linear furanocoumarins and the angular dihydrofuranocoumarin athamantin as active compounds. Oxygenation of the prenyl residue of linear furanocoumarins decreased activity. Further formation of an ester with angelic acid even resulted in complete inactivity. Five active linear furanocoumarins, bergapten, isopimpinellin, xanthotoxin, isoimperatorin, and imperatorin, and two linear furanocoumarins with a substituted furan ring, peucedanin and 8-methoxypeucedanin, were compared in a dietary utilization bioassay. Relative growth rate (RGR) and relative consumption rate (RCR) divided the tested coumarins in three groups of similar activity. Isopimpinellin and peucedanin slightly decreased RGR and RCR of the treated larvae, and xanthotoxin, isoimperatorin, and 8-methoxypeucedanin heavily decreased RGR and RCR. Bergapten and imperatorin differed by the lowest RGR values and rather high RCR values. The effects caused by these two coumarins indicate specific postingestive toxicity. The results obtained in this study add to the reputation of coumarins to be an effective chemical defense, postulating that chemical diversity is a necessary trait for well-defended plants.
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    Proximity of release points of pheromone components as a factor confusing males of the spotted stem borer,Chilo partellus, approaching the trap (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 2065-2075 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Pyralidae ; Chilo partellus ; spotted stem borer ; female sex pheromone ; (Z)-11-hexadecenal ; (Z)-11-hexadecen-1-ol ; multicomponent pheromones ; signal integrity ; dispensing technique ; trap efficiency ; proximity effect
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The effect of proximity of the release points of the two pheromone components (Z)-11-hexadecenal and (Z)-11-hexadecen-1-ol of the spotted stem borer,Chilo partellus (Lepidoptera: Pyralidae) on behavior of the males and on trapping efficiency was investigated. Separating the dispensers of the two components in the trap by a mere 3 cm resulted in a threefold decrease in trap performance, compared to very close release of the components. The result is attributed to possible distortion of the pheromone signal, resulting in confused behavior ofC. partellus males in the vicinity of the trap. The ethological and practical implications of the phenomenon are discussed.
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    Sequestration of host-plant-derived flavonoids by lycaenid butterflyPolyommatus icarus (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 2523-2538 
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    ISSN: 1573-1561
    Keywords: Polyommatus icarus ; Lepidoptera ; Lycaenidae ; Coronilla varia ; Medicago sativa ; Fabaceae ; flavonoids ; sequestration ; plant-insect interactions
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Larvae of the lycaenid butterflyPolyommatus icarus were reared on inflorescences ofCoronilla varia andMedicago sativa, which are rich in flavonoids. Twelve different flavonoids (five compounds from the former and nine from the latter), including aglycones andO-glycosides of kaempferol, quercetin, and myricetin were isolated and identified by spectroscopic means. NMR and MS data for the new acylated glycoside kaempferol 3-O-6″-(3-hydroxy-3-methylglutaroyl)-β-d-glucopyranoside are reported. Comparative HPLC analysis of the respective host plants and of larvae, pupae, and imagines ofP. icarus indicated selective uptake and accumulation of kaempferol vs. quercetin and myricetin derivatives. The latter were excreted largely unchanged through the feces. Irrespective of the larval host plant kaempferol 3-O-glucoside was found as the major flavonoid in larvae, pupae, and imagines ofP. icarus, accounting for approximately 83–92% of all soluble flavonoids in adult butterflies. Within the imagines, approximately 80% of all flavonoids are stored in the wings (especially in the orange submarginal lunules), whereas the remaining 20% reside in the bodies. Feeding experiments with artificial diet demonstrated that the insects are able to form kaempferol 3-O-glucoside by glucosylation of dietary kaempferol. Possible functions of the sequestered flavonoids, especially for mate recognition ofP. icarus, are discussed.
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    Changes in pheromone titer of oblique-banded leafroller,Choristoneura rosaceana, virgin females as a function of time of day, age, and temperature (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 45-69 
    Details
    ISSN: 1573-1561
    Keywords: Pheromone titer, (Z)- and (E)-11-tetradecenyl acetate ; (Z-11-tetradecenol ; age ; time of day ; constant and fluctuating temperature ; Choristoneura rosaceana ; oblique-banded leafroller ; Lepidoptera ; Tortricidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Under a 16:8 hr light-dark photoperiod and 20†C constant temperature, the titers of (Z)-11-tetradecenyl acetate (Z11–14:Ac), (E)-11-tetradecenyl acetate (E11–14:Ac) and (Z)-11-tetradecenol (Z11–14:OH) produced by different-agedChoristoneura rosaceana virgin females varied significantly during the scotophase, with the maximum titer occurring before the onset of calling in day-0 and day-3 females, while in day-5 females the titer remained constant throughout the calling period. There was a significant decrease in the titer of all pheromone components with age, explaining the lesser attractiveness of day-5 females relative to day-0 and day-3 females observed in the field. Under a cold thermocycle simulating condition during the second flight period in the fall, the titers of all pheromone components did not vary with time of day. There was a significant decrease in the amount ofZ11–14:Ac with age but no changes occurred in the minor components. Furthermore, for any given age tested, the amount of each component produced during the period of maximal calling activity remained relatively similar at the two temperature regimes. However, as with the expression of calling behavior, pheromone production was initiated earlier at cooler than at warmer temperatures. At both temperature regimes, female age and time of day influenced the ratio of each pheromone component. These results are discussed in relation to the hypothesis that by calling earlier, less attractive older females may increase their probability of mating.
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    Effect of temperature on biosynthesis of sex pheromone components in potato tuberworm moth,Phthorimaea operculella (Lepidoptera: Gelechiidae) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 2733-2741 
    Details
    ISSN: 1573-1561
    Keywords: Sex pheromone ; pheromone components ratio ; (E,Z,Z)-4,7,10-tridecatrienyl acetate ; (E,Z)-4,7-tridecadienyl acetate ; rearing temperature ; Lepidoptera ; Gelechiidae ; potato tuberworm moth ; Phthorimaea operculella
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Rearing temperature modified the sex pheromone component ratio in the potato tuberworm moth,Phthorimaea operculella. This phenomenon seemed to be induced with ambient temperature by differences in timing and speed of biosynthesis between two pheromone components. (E,Z,Z)-4,7,10-Tridecatrienyl acetate (triene) was mainly synthesized during the pupal period, while most of (E,Z)-4,7-tridecadienyl acetate (diene) was synthesized during a short period just after emergence. Therefore, the ratio of triene in a newly emerging adult was relatively high at all temperatures although the amount of triene was relatively low at 35°C. On the other hand, the synthetic rate of accumulation of diene was clearly modified by ambient temperature. Biosynthesis of diene at 15°C was very low in the first two days and high in the third day. Consequently, a titer of the diene component at 15°C became approximately equivalent to that at 25°C one day later.
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    Stereochemical inversion of pyrrolizidine alkaloids byMechanitis polymnia (Lepidoptera: Nymphalidae: Ithomiinae): Specificity and evolutionary significance (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 2883-2899 
    Details
    ISSN: 1573-1561
    Keywords: Pyrrolizidine alkaloids ; Lepidoptera ; Nymphalidae ; Ithomiinae ; Mechanitis polymnia ; stereochemical inversion ; epimerization ; evolution of PA acquisition
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Pyrrolizidine alkaloids (PAs), acquired by adults or larvae of Danainae and Ithomiinae butterflies and Arctiidae moths from plants, protect these lepidopterans against predators and are biosynthetic precursors of male sex pheromones. The investigation of PAs in many species of wild-caught adults of Ithomiinae showed lycopsamine (1) [(7R)-OH, (2′S)-OH, (3′S)-OH] as the main alkaloid. In incorporation experiments, PA-free (freshly emerged) adults of the ithomiineMechanitis polymnia were fed seven PAs: lycopsamine and four of its known natural stereoisomers—indicine (2) [(7R)-OH, (2′R)-OH, (3′S)-OH], intermedine (3) [(7R)-OH, (2′S)-OH, (3′R)-OH], rinderine (4) [(7S)-OH, (2′S)-OH, (3′R)-OH], and echinatine (5) [(7S)-OH, (2′S)-OH, (3′S)-OH], and two PAs without the 7-OH: supinine (6) [(2′S)-OH, (3′R)-OH] and amabiline (7) [(2′S)-OH, (3′S)-OH]. Males epimerized PAs 3, 4, and 5 mainly to lycopsamine (1). Females fed these same three PAs changed a smaller proportion to lycopsamine; their lesser capacity to modify PAs corresponds to their normal acquisition of already transformed PAs from males during mating rather than through visits of adults to plant sources of PAs. The alkaloids1 and2, both 7R and 3′S, were incorporated without or with minimum change by males and females. Feeding experiments with6 and7 (males only) showed an inversion at the 3′ center of6 and no change in7. The inversion from 7S to 7R (probably via oxyreduction) may be closely related to the evolution of acquisition of PAs by butterflies and moths. Two hypotheses are discussed: (1) The ancestral butterflies are probably adapted to tolerate, assimilate, and use (7R)-PAs (most common in plants; all widespread 1,2-unsaturated macrocyclic PA diesters show this configuration). The development of (7R)-PA receptors in the butterflies could lead to a specialization on this configuration in two ways: to help find PA plants and to utilize these components in sexual chemical communication. A later appearance of (7S)-PAs in plants could have selected an enzymatic system for the inversion of this chiral center in order to continue producing (7R)-PA-derived pheromones. (2) The inversion would be due to the evolution of a enzyme system specialized in the transport of (7R)-PAs to the integument; the failure of this system to carry (7S)-PAs led to an enzymatic system to invert them to transportable (7R)-PAs. In this case, the 7R configuration is an effect and not a cause of (7R)-PA-derived pheromones. In both hypotheses, the partial inversion of the 3′-asymmetric center, when the butterfly was fed intermedine (3), rinderine (4), and supinine (6), could be fortuitous due to the conformation of the molecule and/or the enzymatic system.
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    Effects of host plant,Gossypium hirsutum L., on sexual attraction of cabbage looper moths,Trichoplusia ni (Hübner) (Lepidoptera: Noctuidae) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 2959-2974 
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    ISSN: 1573-1561
    Keywords: Cabbage looper ; Trichoplusia ni ; Lepidoptera ; Noctuidae ; pheromone ; kairomone ; attractants ; host finding ; (S)-(+)-linalool
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Unmated female or male cabbage looper moths,Trichoplusia ni (Hübner), were attracted more often in a flight tunnel to a cage with moths of the opposite sex and a bouquet of cotton foliage. Increased sexual attractiveness of females with plants may be a result of stimulation of pheromone release in response to plant odor, since more males were attracted when odor of cotton foliage was passed over females than when odor of females was passed over cotton foliage before venting into the flight tunnel. Increased sexual attractiveness of males with plants is due in part to host odor enhancement of female attraction to male pheromone, since more females were attracted to synthetic male pheromone (a blend of enantiomers of linalool and isomers of cresol) and a cotton leaf extract than were attracted to male pheromone alone. A short synthesis procedure was developed for (S)-(+)-linalool, the major component of the male sex pheromone, isolated from hair pencils, used in these tests.
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    Moth responses to selectively fluorinated sex pheromone analogs (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 2705-2719 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Pyralidae ; Ostrinia nubilalis ; 11-tetradecenyl acetate ; (Z)-14-fluoro-11-tetradecenyl acetate ; (Z)-14,14,14,-trifluoro-11-tetradecenyl acetate ; pheromone analogs ; fluorinated analogs
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Partially fluorinated analogs of the European corn borer (Ostrinia nubilalis) female sex pheromone, 11-tetradecenyl acetate (97:3Z:E), having mono- and trifluorsubstitutions at the terminal carbon of the pheromone chain, mimicked the biological activity of the pheromone, while analogs with fluorine at either side of the double bond and a pentafluoro analog were essentially inactive. Comparison of the pheromonal activity of these analogs with the previously reported activity of similarly fluorinated pheromones in five other species of moths revealed an unpredictable relationship between fluorine substitution pattern and pheromone-mimicking activity. Fluorine substitution patterns that rendered pheromonal analogs biologically inactive in the European corn borer had no detrimental influence upon pheromonal activity in other species and the converse was also true. This is evidence that the relative importance of electronic qualities of sites within a pheromone molecule differ from species to species. Furthermore, it indicates that the biochemical components (pheromone receptor proteins, binding proteins, and enzymes) that make up moth olfactory chemosensory systems must also vary structurally from species to species, despite the fact that they are involved in olfactory sensing of compounds having very similar chemical structure.
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    Chiral esters: Sex pheromone of the bagworm,Oiketicus kirbyi (Lepidoptera: Psychidae) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 3083-3096 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Psychidae ; Oiketicus kirbyi ; bagworm ; sex pheromone ; pheromone chirality ; 1-methylbutyl octanoate ; 1-methylbutyl non-anoate ; 1-methylbutyl decanoate ; 1-methylbutyl dodecanoate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Gas chromatographic-electroantennographic detection (GC-EAD) analyses of pheromone extract of female bagworms,Oiketicus kirbyi (Guilding), revealed five EAD-active compounds. Retention index calculations, GC-mass spectrometry in both full-scan and selected-ion monitoring modes and GC-EAD analyses of authentic standards identified the compounds as 1-methylbutyl octanoate (MBO), 1-methylbutyl nonanoate (MBN), 1-methylbutyl decanoate (MBD), 1-methylpentyl decanoate (MPD), and 1-methylbutyl dodecanoate (MBDD). Of these five chiral esters, MBD was most abundant in extracts and elicited the strongest antennal response. In field experiments in Costa Rica, (R)-MBD attractedO. kirbyi males, whereas (S)-MBD in combination with (R)-MBD inhibited response.R but notS enantiomers of MBO, MBN, and MBDD strongly synergized attraction to (R)-MBD. (S)-MBO and (S)-MBDD were inactive, whereas (S)-MBN was inhibitory. (R)-, (S)- and racemic MPD were inactive. Blends of (R)-MBD in ternary combination with either (R)-MBO and (R)-MBN or (R)-MBN and (R)-MBDD were as attractive as the five-ester blend. Five- and four-ester blends were equally attractive, suggesting redundancy of pheromone components for attraction of males. The multiple sex pheromone component blend of chiral esters inO. kirbyi may have evolved to maintain species-specific communication in bagworm communities of tropical Americas.
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    Potential role of lipoxygenases in defense against insect herbivory (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 651-666 
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    ISSN: 1573-1561
    Keywords: Helicoverpa zea ; Lepidoptera ; Noctuidae ; lipoxygenase ; lipid peroxidation ; resistance ; herbivory ; soybean ; tomato ; cotton ; oxidative stress ; induced defense
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The potential role of the plant enzyme lipoxygenase in host resistance against the corn earwormHelicoverpa zea was examined. Lipoxygenase is present in most of the common host plants ofH. zea, with highest activity in the leguminous hosts such as soybean and redbean. Treatment of dietary proteins with linoleic acid and lipoxygenase significantly reduced the nutritive quality of soybean protein and soy foliar protein. Larval growth was reduced from 24 to 63% depending upon treatment. Feeding byH. zea on soybean plants caused damage-induced increases in foliar lipoxygenase and lipid peroxidation products. Larvae feeding on previously wounded plant tissue demonstrated decreased growth rates compared to larvae feeding on unwounded tissue. Midgut epithelium from larvae feeding on wounded tissues showed evidence of oxidative damage as indicated by significant increases in lipid peroxidation products and losses in free primary amines. The potential role of oxidative and nutritional stress as a plant defensive response to herbivory is discussed.
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    Nature and role of sexual pheromones emitted by males ofAcrolepiopsis assectella (LEP.) (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 1571-1581 
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    ISSN: 1573-1561
    Keywords: Male sex pheromone ; n-alkanes ; leek moth ; Lepidoptera ; Acrolepiidae ; hair-pencils ; gas chromatography-mass spectrometry ; gas chromatography-FT-IR ; female arrestant ; acceptance posture
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Seven compounds that do not exist in the extracts from legs of males have been isolated in the hair-pencil extracts of maleAcrolepiopsis assectella. By combining techniques of GC-MS and GC-FT-IR, six of these compounds have been identified. They are sixn-alkanes: hexadecane (C16), heptadecane (C17), octadecane (C18), nonadecane (C19), eicosane (C20), and heneicosane (C21). Twelven-alkanes of the homologous series, from the C14–C25 compounds were presented to virgin females, mated females, and males. At the end of the scotophase, four of then-alkanes (C16, C17, C19, C21) present in the hair-pencil extract induced the virgin females to adopt the acceptance posture after having induced the virgin females to remain stationary. The two othern-alkanes (C18 and C20) present in the extract have less effect on the females similar to then-alkanes not present in the males. The blends tested do not seem to indicate any synergy between the most active compounds. The threen-alkanes with an odd number of carbons and the C16 compound would thus be the principle components of the male pheromone ofA. assectella. As well as their role of female aphrodisiac, they tend to make males and fertilized females flee.
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    Differential toxicity of juglone (5-hydroxy-1,4-naphthoquinone) and related naphthoquinones to saturniid moths (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 1631-1641 
    Details
    ISSN: 1573-1561
    Keywords: 1,4-Naphthoquinone ; allelochemical toxicity ; detoxification ; plant-insect interaction ; Lepidoptera ; Saturniidae ; Actias luna ; Callosamia promethea ; juglone ; plumbagin ; menadione ; lawsone ; quinones
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The preferred hosts of the saturniid mothActias luna include members of the Juglandaceae, whose foliage contain the toxin juglone (5-hydroxy-1,4-naphthoquinone). The performance ofActias luna andCallosamia promethea was compared when fourth-instar larvae of each were fed birch foliage, a mutually acceptable food plant, or birth supplemented with 0.05% (w/w) juglone.A. luna fed juglone exhibited no changes in developmental time or mortality compared to a diet without juglone. In contrast, juglone-supplemented diets, when fed toC. promethea, caused negative growth rate, and a 3.6-fold decrease in consumption rate. The performance ofA. luna also was compared on birch and walnut; larvae developed and grew more rapidly on an all-walnut vs. an all-birch diet. To examine the effect of 1,4-naphthoquinone structure onA. luna survival, first instars were fed on birch supplemented with varying concentrations of juglone (J), menadione (M), plumbagin (P), or lawsone (L). In diets supplemented at 0.05% (w/w), none of the compounds produced effects significantly different from controls. In diets supplemented at 0.5% (w/w), the treatments produced significant toxic effects in the order P〉M=L〉J for mortality, and P〉L〉M=J for increased developmental time. Late-instarA. luna are clearly resistant to juglone compared toC. promethea, and early-instarA. luna are resistant to several related 1,4-naphthoquinones. These results suggest a chemical basis for host choice among saturniids. In addition, the luna-walnut system may be a valuable model for studying quinone detoxication.
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    Plant response to eggs vs. Host marking pheromone as factors inhibiting oviposition byPieris brassicae (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 1657-1665 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Pieridae ; Pieris brassicae ; Host Marking Pheromone ; Cruciferae ; Brassica oleracea ; induction ; oviposition deterrency
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Pieris brassicae L. butterflies secrete miriamides onto their eggs. These avenanthramide alkaloids are strong oviposition deterrents when sprayed onto a cabbage leaf. However, these compounds could not be detected in cabbage leaves from which egg batches had been removed two days after deposition and that still showed oviposition deterrency. It was concluded that the miriamides were not directly responsible for the avoidance by females of occupied leaves while searching for an oviposition site. Evidence was obtained that cabbage leaves themselves produce oviposition deterrents in response to egg batches. Fractions containing potent oviposition deterrents could be isolated from surface extracts of leaves from which previously laid egg batches had been removed. The term host marking pheromone that was used previously is not applicable in this case.
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    Hormonal control of pheromone responsiveness in the male black cutwormAgrotis ipsilon (1993)
    Springer
    Cellular and molecular life sciences 49 (1993), S. 721-724 
    Details
    ISSN: 1420-9071
    Keywords: Lepidoptera ; Noctuidae ; Agrotis ipsilon ; black cutworm ; juvenile hormone ; allatectomy ; pheromone reception ; sexual behaviour ; tenoxycarb ; KK-42
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract In Lepidoptera, reproduction is linked to chemical communication between conspecific partners. When exposed to the female sex pheromone, males respond by exhibiting typical sexual behaviour which leads to mating. Here we show that presence of the juvenile hormone producing gland (corpora allata) of the male black cutworm,Agrotis ipsilon, is necessary for pheromone responsiveness. Allatectomized males do not show any sexual behaviour, although their antennal olfactory system is functional. Allatectomized males implanted with active corpora allata recover full pheromone receptivity. It is suggested that reproductive processes are synchronized in males and females through endocrine control; timing of the mating activity could serve as an adaptive strategy linked to the migratory behaviour of this species.
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    Tangential medulla neurons in the mothManduca sexta. Structure and responses to optomotor stimuli (1993)
    Springer
    Journal of comparative physiology 173 (1993), S. 783-799 
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    ISSN: 1432-1351
    Keywords: Insect vision ; Lepidoptera ; Medulla neurons ; Optomotor stimulation ; Direction selectivity
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract InManduca sexta, large tangential cells connect the medulla via the lobula valley (LoV) tract to the midbrain and the contralateral medulla. Tract neurons have been stained and recorded to determine their responses to optomotor stimulation. Neurons in the LoV-tract comprise a physiologically and anatomically heterogeneous population: 1. Motion insensitive medulla tangential (Mt) neurons arise from cell bodies in the ventral rind. Heterolateral cells arborize massively in both medullae and one or both halves of the midbrain. Mt-neurons respond to changes in light intensity. Physiological and anatomical evidence argues for their monocularity and transmission from the medulla on the side of the soma to the central brain and the contralateral medulla. 2. Motion sensitive neurons with cell bodies behind the protocerebral bridge connect the midbrain to the ipsior contralateral medulla. Direction-selective responses are characterized by excitation to motion in the preferred and inhibition in the opposite direction with maxima either in a horizontal or vertical direction. Peak values appear at contrast frequencies of appr. 3/s. The results suggest that these neurons are binocular and relay information from the midbrain to the medulla. They have been labelled as centrifugal medulla tangential (cMt) neurons. The possible roles for tract neurons in visually guided behaviour are discussed.
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    Inter-specific avoidance of egg-associated semiochemicals in four tortricids (1993)
    Springer
    Cellular and molecular life sciences 49 (1993), S. 998-1001 
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    ISSN: 1420-9071
    Keywords: Lepidoptera ; Tortricidae ; synomone ; pheromone ; behavior ; oviposition ; Lobesia botrana ; Cydia pomonella ; Cydia molesta ; Eupoecilia ambiguella ; fatty acids ; esters of fatty acids
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract Oviposition of four tortricid pests of vineyards (the European grapevine moth and the grape berry moth) and fruit orchards (the codling moth and the oriental fruit moth) is deterred by a blend of straight chain fatty acids and esters of fatty acids that have been identified in the eggs of one of them: the European grapevine moth (EGVM)Lobesia botrana. This is the first evidence of inter-specific recognition of an egg-like signal in moths. We demonstrate that oviposition site selection is influenced by population density, avoidance of deterrent being most important when females are isolated. Inter-specific egg recognition might be an important phenomenon, especially in species competing for a common food resource. We propose the term ‘oviposition regulating synomone’ for molecules and blends that affect the inter-specific spacing of eggs.
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    Propheromones derived from codlemone (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 1-9 
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    ISSN: 1573-1561
    Keywords: Insect pheromones ; C. pomonella ; C. nigricana ; Lepidoptera ; Tortricidae ; propheromone ; codlemone ; conjugated dienes ; pheromone protection ; pheromone release
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Tricarbonyl [(8,9,10,11-η-8,10-dodecadien-l-ol] iron and the corresponding acetate prepared from 8,10-dodecadien-1-ol or its acetate, comprise the protected double-bond system of the molecule. After coming in contact with ambient oxygen, the iron complexes in question slowly release the corresponding pheromones of, for example, the codling moth,Cydia pomonella, and the pea moth,Cydia nigricana in highE,E purity and amounts that are sufficient for pest monitoring. A simple dispenser for propheromone application is proposed. Results of release rates in laboratory conditions and field trials are given.
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    Effect of rearing temperature on pheromone component ratio in potato tuberworm moth,Phthorimaea operculella, (Lepidoptera: Gelechiidae) (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 71-81 
    Details
    ISSN: 1573-1561
    Keywords: Sex pheromone ; pheromone components ratio ; (E,Z,Z)-4,7,10-tridecatrienyl acetate ; (E,Z)-4,7-tridecadienyl acetate ; rearing temperature ; Lepidoptera ; Gelechiidae ; potato tuberworm moth ; Phthorimaea operculella
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The ratio of two components in the sex pheromone of the potato tuberworm moth,Phthorimaea operculella, was influenced by the rearing temperature. The percentage of the (E,Z,Z)-4,7,10-tridecatrienyl acetate dropped as the rearing temperature was raised. The total amount of the pheromone did not change parallel with the change of ratio. The critical period sensitive to temperature seemed to be the pupal stage. Temperature in the larval stage may also influence the ratio slightly. The biological significance of the phenomenon was also discussed.
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    Relative importance of infochemicals from first and second trophic level in long-range host location by the larval parasitoidCotesia glomerata (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 47-59 
    Details
    ISSN: 1573-1561
    Keywords: Hymenoptera ; Braconidae ; Lepidoptera ; Pieridae ; Cruciferae ; tritrophic interactions ; foraging behavior ; host-habitat location ; herbivoreinduced synomones ; flight chamber ; infochemicals
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Recently parasitoids were hypothesized to encounter a reliability-detectability problem relating to chemical stimuli from the first and second trophic level, when searching for hosts. The relative role of infochemicals originating from the host,Pieris brassicae (second trophic level), and its food plant, cabbage (first trophic level), have been investigated with respect to long-range host location by the larval parasitoidCotesia glomerata. Flight-chamber dual choice tests showed that uninfested cabbage plants are least attractive to female wasps. Host larvae and their feces were more attractive than clean plants but far less attractive than artificially damaged and herbivore-damaged plants. The plant-host complex, with host larvae actively feeding on the plant, was the most attractive odor source for the parasitoids. The data indicate that one of the solutionsC. glomerata uses to solve the reliability-detectability problem is to respond to infochemicals that are emitted from herbivore-damaged plants. Whether these infochemicals are herbivore-induced synomones that are produced by the plant remains to be demonstrated. Infochemicals emitted by the herbivore or its by-products are of little importance in the foraging behavior ofC. glomerata.
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    Diterpene resin acids: Major active principles in tall oil against Variegated cutworm,Peridroma saucia (Lepidoptera: Noctuidae) (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 1075-1084 
    Details
    ISSN: 1573-1561
    Keywords: Tall oil ; resin acids ; abietic acid ; dehydroabietic acid ; isopimaric acid ; Peridroma saucia ; Lepidoptera ; Noctuidae ; variegated cutworm ; bioactivity ; natural insecticide
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Tall oil, a by-product of the kraft process for pulping softwood, has been shown to have insecticidal properties. In the present study, the active principles in tall oil against the variegated cutworm,Peridroma saucia Hübner, were investigated. GC-MS analysis showed that abietic, dehydroabietic, and isopimaric acids were major resin acid components of crude tall oil and depitched tall oil. When crude tall oil samples of differing resin acid composition were incorporated into artificial diet at a concentration of 2.0% fresh weight, they suppressed larval growth by 45–60% compared to controls. This suppression was significantly (P≤0.05) correlated with the equivalent contents of abietic, dehydroabietic, isopimaric, and total resin acids. These results were also evident from a diet choice test, showing that the second-instar larvae obviously selected diets with low levels of resin acids when different diets were randomly arranged in a Petri dish. Bioassays with pure resin acids (abietic, dehydroabietic, and isopimaric acids) demonstrated that all individual chemicals have similar bioactivity against this insect. Comparison of the bioactivities of depitched tall oil and an equivalent mixture of pure resin acids in thePeridroma chronic growth bioassay indicated that pure resin acids and depitched tall oil share a common mode of action to this insect. This study confirms that resin acids are major active principles in tall oil against the variegated cutworm, but other chemicals likely also contribute to the bioactivity of tall oil.
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    Host recognition by entomopathogenic nematodes: Behavioral response to contact with host feces (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 1219-1231 
    Details
    ISSN: 1573-1561
    Keywords: Host recognition behavior ; entomopathogenic nematodes ; feces ; Spodoptera exigua ; Lepidoptera ; Noctuidae ; Popillia japonica ; Coleoptera ; Scarabaeidae ; Blattella germanica ; Blatteria ; BlattellidaeAcheata domesticus ; Orthoptera ; Gryllidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Host recognition by entomopathogenic nematodes may occur through contact with insects' excretory products, cuticle, or gut contents. We analyzed the behavioral responses of four species of entomopathogenic nematodes during contact with feces of natural or experimental hosts. Host recognition by nematodes was manifested in alterations in the frequency and/or duration of one or more search parameters including forward crawling, headwaving, body-waving, stopping, backward crawling, head-rubbing, and headthrusting.Heterorhabditis bacteriophora andSteinernema glaseri showed behavioral responses to contact with feces of their natural hosts,Spodoptera exigua (Lepidoptera) andPopillia japonica (Coleoptera), and to the experimental hosts,Acheata domesticus (Orthoptera) andBlatella germanica (Blatteria).Steinernema carpocapsae responded only toB. germanica feces, whereas5. scapterisci did not significantly respond to any of the insect species. During contact with cockroach feces, all nematodes, exceptS. scapterisci, showed avoidance behavior. We suggest that ammonia present in cockroach feces is inhibitory to nematodes. Specific host recognition by entomopathogenic nematodes may be an important mechanism to maintain host affinities.
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    Effects of nitrogen and Douglas-fir allelochemicals on development of the gypsy moth,Lymantria dispar (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 1245-1263 
    Details
    ISSN: 1573-1561
    Keywords: Artificial diet ; herbivory ; nitrogen ; Lymantria dispar ; Lepidoptera ; Lymantriidae ; monoterpenes ; nutritional ecology ; phenolics ; Pseudotsuga menziesii
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Two experiments were conducted to examine the influence of foliar nitrogen, terpenes, and phenolics of Douglas-fir on the development of gypsy moth larvae. In the first experiment, foliar concentrations of nitrogen and allelochemicals were manipulated by fertilizing 3-year-old potted seedlings with 0 or 200 ppm nitrogen. Concentrations of foliar nitrogen (0.33–2.38%) were negatively correlated with the phenolics (15.8–24.4 mg/g). Sixth-instar larvae previously reared on current-year Douglas-fir needles were allowed to feed on these seedlings. Pupal weights (312.8–995.6 mg) were positively correlated with levels of foliar nitrogen, negatively correlated with amounts of foliar phenolics, and uncorrelated with terpene concentrations. In the second experiment, terpene and phenolic extracts from Douglas-fir foliage were incorporated at natural levels into artificial diets with high and low levels of protein nitrogen. Neonate larvae grew faster and were larger on the high nitrogen control diet (4.1–4.5%), however, fourth instars performed better on the control diet with low nitrogen levels (2.5–2.7%). Foliar terpenes incorporated into diet had little effect on neonate fitness, but may induce subtle physiological changes in later instar larvae. Phenolics, alone or in combination with terpenes, excessively suppressed growth and survival, with no individuals living through the fourth instar, regardless of the nitrogen level. Incorporating foliar phenolic extracts into artificial diet caused unnatural levels of toxicity and failed to clarify the effects of Douglas-fir phenolics on gypsy moth fitness. Foliar nitrogen is a key factor influencing gypsy moth development on Douglas fir, but may be mitigated to some degree by phenolics.
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    Cardenolides fromErysimum cheiranthoides: Feeding deterrents toPieris rapae larvae (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 1355-1369 
    Details
    ISSN: 1573-1561
    Keywords: Pieris rapae ; Erysimum cheiranthoides ; feeding deterrents ; cardenolides ; digitoxigenin 3-O-β-D-glucoside ; glucodigigulomethyloside ; glucodigifucoside ; erychroside ; cheirotoxin ; strophanthidin glycosides ; digitoxigenin glycosides ; Lepidoptera ; Pyridae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Larvae of the cabbage butterfly,Pieris rapae, refuse to feed on the wild mustard,Erysimum cheiranthoides, due to the presence of alcoholextractable deterrents. The active components were extracted inton-BuOH, and this extract was separated into four fractions (I–IV) by reverse-phase HPLC. Fractions III and IV retained the feeding deterrent activity. The activity of fraction III was found to be due to the cardenolide diglycosides 1 and 2, which were previously reported as oviposition deterrents for gravidP. rapae butterflies. Three active compounds were isolated from fraction IV by column chromatography on silica gel followed by reverse-phase HPLC. These compounds were identified as a monoglycoside, digitoxigenin 3-O-β-D-glucoside (4), and two diglycosides, glucodigigulomethyloside (5) and glucodigifucoside (6). An additional cardenolide isolated from fraction II was identified as cheirotoxin (7). All compounds were identified by UV, NMR (1H and13C), and mass spectrometry, as well as hydrolysis experiments. The feeding deterrent activity of these compounds was compared with that of related commercially available chemicals and other compounds isolated fromE. cheiranthoides.
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    2-hydroxy-4,7-dimethoxy-1,4-benzoxazin-3-one (N-O-Me-DIMBOA), a possible toxic factor in corn to the southwestern corn borer (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 531-542 
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    ISSN: 1573-1561
    Keywords: Corn ; Zea mays (L.) ; southwestern bora borer ; Diatraea grandiosella ; Dyar ; Lepidoptera ; Pyralidae ; feeding resistance ; 2-hydroxy-4,7-dimethoxy-1,4-benzoxazin-3-one ; N-O-Me-DIMBOA
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The southwestern corn borer (SWCB),Diatraea grandiosella Dyar, is a major pest of corn,Zea mays L., in the southern United States. The damage to corn is caused primarily by larval feeding on leaf, ear, and stem tissues. In this study, 2-hydroxy-4,7-dimethoxy-1,4-benzoxazin-3-one (N-O-Me-DIMBOA) was identified by MS and NMR as present in corn whorl surface waxes. This compound has evidently not been isolated previously, but its glucoside has been reported in corn, wheat, andCoix lachryma. It is present in the waxes in a higher concentration than DIMBOA (2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one) and 6-MBOA (6-methoxybenzoxazolinone). It was toxic to the SWCB in a stress diet, but it was less toxic to this insect than 6-MBOA when incorporated in the standard rearing diet. Nevertheless, it may have some role in the resistance of corn to the SWCB because the total surface wax content is higher in resistant lines than in susceptible lines.
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    Pyrrolizidine alkaloids in the arctiid mothHyalurga syma (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 669-679 
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    ISSN: 1573-1561
    Keywords: Pyrrolizidine alkaloids ; alkaloid sequestration ; alkaloid transformation ; Boraginaceae ; Heliotropium transalpinum, Heliotropium peruvianum ; Lepidoptera ; Arctiidae ; Pericopinae ; Hyalurga syma ; chemical defense ; Araneidae ; Nephila clavipes ; orb-weaving spider
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The arctiid mothHyalurga syma (subfamily Pericopinae) sequesters pyrrolizidine alkaloids (PAs) from its larval food plantHeliotropium transalpinum (Boraginaceae). Colorimetric quantification of total PAs in the larvae, pupae, and adults ofHyalurga revealed mean values of about 286–445μg per individual (1.4–2.6% of dry weight). The PA mixtures found in the moth and its larval food plant were evaluated by GC-MS. Food-piant leaves were found to contain the diastereoisomeric retronecine esters indicine (IIIa), intermedine (IIIb), and lycopsamine (IIIc), and the heliotridine ester rinderine (IIId) only as minor constituents, whereas 3′-acetylrinderine (IVc) (68% of total PAs) and the respective 3′-acetyl esters of indicine (IVa) and intermedine (IVb) (both 17%) were the major alkaloids. Supinine (IIa) is detectable in traces only. The PA mixtures in eggs, larvae, pupae, and imagines ofHyalurga were identical: indicine, intermedine, and lycopsamine accompanied by considerable amounts of supinine and amabiline or coromandalinine (IIb/IIc) were the major components. Only larvae were found to store small quantities of a 3′-acetyl derivative. Rinderine and its 3′-acetyl ester were never found in the insects. Low concentrations of the arctiidspecific PA callimorphine (I) were present in larvae, pupae, and imagines. The differences in the PA patterns of the insects and their larval food plant suggest thatHyalurga is capable of modifying plant-derived PAs by inversion of the 7-OH configuration (conversion of the necine base heliotridine into retronecine), and perhaps the inversion of the 3′-OH [conversion of (+)-trachelanthic acid into (−)-viridifloric acid], although the possibility of a selective sequestration of the respective retronecine esters cannot be excluded. Some trials with the orb-weaving spiderNephila clavipes, a common neotropical predator, showed that both freshly emerged and field-caught adults ofHyalurga syma are liberated unharmed by the spider. The liberation could be related to the presence of PAs in the moths.
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    Structure-activity correlations among analogs of the currant clearwing moth pheromone (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 735-750 
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    ISSN: 1573-1561
    Keywords: Pheromone analogs ; (E,Z)-2,13-octadecadien-1-yl acetate ; EAG ; gas chromatography ; vapor pressure ; currant clearwing moth ; Synanthedon tipuliformis Clerk ; Lepidoptera ; Sesiidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Eleven analogs of (E,Z)-2,13-octadecadien-1-yl acetate1, a main pheromone component of the currant clearwing moth,Synanthedon tipuliformis Clerk (Lepidoptera: Sesiidae) were synthesized and tested for their biological activities by electroantennography (EAG). To correct the EAG data for differences in volatility of the analogs, their vapor pressures were estimated by a gas chromatographic method. All structural changes in the parent molecule were found to reduce the biological activity to various degrees. The most active analog tested was the carbamate12, whose activity was almost comparable to that of the pheromone component1. Structure-activity correlations showed that hydrophobic, steric, and electronic effects of chain terminal groups might be responsible for variations in biological activity of the conformationally unchanged (E,Z)-2,13-analogs
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    Trail and arena marking by caterpillars ofArchips cerasivoranus (lepidoptera: Tortricidae) (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 1479-1489 
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    ISSN: 1573-1561
    Keywords: Archips cerasivoranus ; Yponomeuta cagnagella ; trail following ; silk ; trail pheromone ; Lepidoptera ; Tortricidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The activity ofArchips cerasivoranus caterpillars is largely limited to their colonial silk web and trails. Silk pulled directly from the spinnerets of caterpillars and wound onto paper strips to form artificial trails elicited locomotion from the larvae. Trails made from extracts of silk and silk glands also elicited locomotion. These and other observations reported here indicate that the caterpillars are responsive to a water-soluble pheromone that is a component of the silk strand. Marker pheromones appear not to be secreted from other regions of the body, as has been reported for some other trail-following caterpillars.
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    Electrophysiological and behavioral responses of turnip moth males,Agrotis segetum to fluorinated pheromone analogs (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 143-157 
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    ISSN: 1573-1561
    Keywords: Agrotis segetum ; Lepidoptera ; Noctuidae ; (Z)-5-decenyl acetate ; fluorinated analogs ; behavioral activity ; electrophysiological activity ; flight tunnel ; single sensillum recording ; field test ; lipophobicity ; lipid solubility ; structure-activity analysis ; pheromone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The electrophysiological and behavioral responses of maleAgrotis segetum to fluorinated analogs of (Z)-5-decenyl acetate (Z5-10∶OAc) were investigated. The single sensillum recordings showed that 4,4-difluoro-(Z)-5-decenyl acetate (4,4-F2), 7,7-difluoro-(Z)-5-decenyl acetate (7,7-F2), 10,10,10-trifluoro-(Z)-5-decenyl acetate (10,10,10-F3) and 7,7,8,8-tetrafluoro-(Z)-5-decenyl acetate (7,7,8,8-F4) were each 100-fold less active than the natural Z5-10 ∶ OAc, whereas the 7,7,8,8,9,9,10,10,10-nonafluoro-(Z)-5-decenyl acetate (F9) analog was essentially inactive. A mixture of Z5-10 ∶ OAc, Z7-12 ∶ OAc, and Z9-14 ∶ OAc on a filter paper dispenser was as attractive as female gland extracts when tested in a flight tunnel. With Z5-10∶OAc omitted, the two-component mixture elicited a significantly lower male response. Four analogs, 7,7-F2, 10,10,10-F3, 7,7,8,8-F4, and F9, were added separately to the two-component mixture to replace Z5-10∶OAc. The responses elicited by the mixtures containing the 7,7-F2, 10,10,10-F3, and 7,7,8,8-F4 analogs did not differ significantly from that of the natural three-component mixture and the two-component mixture, whereas the mixture containing F9 elicited a significantly lower male response, as low as the response to the two-component mixture. In a field test the mixtures containing 10,10,10-F3 and 7,7,8,8-F4 were significantly more active than the two-component mixture, but still less active than the natural three-component mixture. It appears that field tests provided greater discrimination among pheromone analogs in assessing their behavioral activity than the flight-tunnel test did. Structure-activity analyses demonstrate the importance of the lipophilic interaction between the terminal alkyl chain and the receptor site for the activity of the stimulus. The lipophobicity of the fluorinated analogs impedes a productive receptor interaction.
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    Constituents of wing gland and abdominal hair pencil secretions of male African sugarcane borer,Eldana saccharina walker (Lepidoptera: Pyralidae) (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 2255-2277 
    Details
    ISSN: 1573-1561
    Keywords: Eldana saccharina ; Lepidoptera ; Pyralidae ; exocrine secretions ; sex pheromone ; aggregation pheromone ; electroantennograms ; electroantennographic detection ; NMR
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract In addition totrans-3,7-dimethyl-6-octen-4-olide (eldanolide), vanillin, and 4-hydroxybenzaldehyde, identified by French workers in the wing gland and abdominal hair pencil secretions of the male African sugarcane borer,Eldana saccharina, we have, in an earlier note, reported the presence of several other terpenoid, aromatic, and unbranched-chain compounds such as, (Z)-3,7-dimethylocta-2,6-dienoic acid, 6,10,14-trimethyl-2-pentadecanol, 4-hydroxy-3-methoxybenzyl alcohol, 1-octadecane thiol, 16-hexadecanolide, and 18-octadecanolide in these secretions. In the present paper experimental details and spectral evidence supporting the identification of these compounds, as well as the identification of (Z)-9-hexadecenal and cw-3,7-di-methyl-6-octen-4-olide (cis-eldanolide), are reported. Using electroantennography it was found that male and female antennae reacted approximately equally strongly to both secretions. This result was confirmed in analyses of the secretions using coupled gas chromatography-electroantennography and it was found that male as well as female antennae responded to eldanolide. Vanillin, substituted phenols related to vanillin, and some oxygenated monoterpenes elicited weak responses in male and female antennae. In some analyses 6,10,14-trimethyl-2-pentadecanol, present in the secretions of the insect, gave a strong antennal response. The results obtained in dynamic and static headspace determinations showed that several of the organic compounds present in the glandular secretions are released in detectable quantities and are present in widely varying quantitative ratios in the effluvia of individual calling male moths.
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    Diel rhythms of calling behavior and pheromone production of oriental tobacco budworm moth,Helicoverpa assulta (Lepidoptera: Noctuidae) (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 2953-2963 
    Details
    ISSN: 1573-1561
    Keywords: Helicoverpa assulta ; sex pheromone ; calling ; diel periodicity ; Lepidoptera ; Noctuidae ; (Z)-9-hexadecenal ; hexadecanal ; (Z)-11-hexadecenal ; (Z)-9-hexadecenyl acetate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Both calling behavior and titer of (Z)-9-hexadecenal (Z9-16: Al), the major sex pheromone component ofHelicoverpa assulta, in pheromone glands showed distinct diel periodicity, and these two were synchronous. Calling was most actively performed and the pheromone titer reached a maximum from 2 to 6 h after lights-off. During photophase, no calling was shown and only a relatively small amount of Z9-16:A1 was detected. However, there was a time lag of a few days between peak calling activity and maximum pheromone titer. The pheromone titer was maximal from age 1 day to age 5 days and thereafter decreased while calling was most actively performed after age 3 days. Titers of three minor components, hexadecenal, (Z)-11-hexadecenal, and (Z)-9-hexadecenyl acetate, showed similar daily fluctuation patterns to that of Z9-16:Al, but relative to the titer of Z9-16:Al, the titer of the two aldehyde components remained relatively constant whereas that ofZ9-16:Ac increased in the late scotophase.
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    Sex pheromone catabolism in the redbanded leafroller moth (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 751-762 
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    ISSN: 1573-1561
    Keywords: Lepidoptera ; Tortricidae ; Argyrotaenia velutinana ; tritiated pheromone ; 11-tetradecenyl acetate ; sensory biochemistry ; catabolism
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Tritium-labeled components of the red-banded leaf-roller female sex pheromone, (Z)- and (E)-[11,12-3H2]-11-tetradecenyl acetate (57 Ci/mmol), applied to antennae of males and females were degraded causing formation of tritiated 11-tetradecenol, 11-tetradecenoic acid, and water. Results indicate that the catabolic pathway involves acetate hydrolysis, oxidation of alcohol to fatty acid, and degradation of the acid viaβ-oxidation. Both geometric isomers were degraded equally well by males but degradation proceeded comparatively less rapidly with female antennae. It is surmised that under natural conditions of olfactory sensing, sex pheromone impinging upon the moth's antennae is probably subject to a similar catabolic fate.
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    (6Z,9Z-3R,4S)-Epoxy-heptadecadiene: major sex pheromone component of the larch looper,Semiothisa sexmaculata (Packard) (Lepidoptera: Geometridae) (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 843-850 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Geometridae ; Semiothisa ; S. sexmaculata ; S. marmorata ; S. neptaria ; sex pheromone ; sex attractant ; enantiomer ; (3Z,6Z,9Z)-heptadecatriene ; (6Z,9Z-3R,4S)-epoxy-heptadecadiene ; (6Z,9Z-3S,4R)-epoxy-heptadecadiene
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Gas chromatographic-electroantennographic analysis (GC-EAD) of female larch looper,Semiothisa sexmaculata (Packard), gland extracts revealed two EAD-active compounds. Retention index calculations, GC-mass spectroscopy in selected ion monitoring mode, and GC-EAD analysis of authentic standards identified the compounds as (3Z,6Z,9Z)-heptadecatriene (3Z,6Z,9Z-17∶H) and (6Z,9Z)-cis-3,4-epoxy-heptadecadiene (6Z,9Z-cis-3,4-epoxy-17∶H). Chirality determination of the monoepoxydiene in gland extracts was impeded by small quantities, but field experiments indicated that maleS. sexmaculata were most strongly attracted to enantiomerically enriched 6Z,9Z-3R,4S-epoxy-17∶H (69% ee), while maleS. neptaria (Guenée) responded well to various blends of theR,S- and S,R-epoxide enantiomers. Binary combinations of theR,S-epoxide enantiomer with 3Z,6Z,9Z-17∶H significantly inhibited response by maleS. sexmaculata, but strongly enhanced attraction of sympatric maleS. marmorata Ferguson. Enantiomerically enriched 6Z,9Z-3R,4S-epoxy-17∶H can be used as a trap bait to monitor populations of the larch-defoliatingS. sexmaculata. Whether 6Z,9Z-3R,4S-epoxy-17∶H serves as single component sex pheromone inS. sexmaculata or small amounts of 6Z,9Z-3S,4R-epoxy-17∶H synergize or suppress optimal attraction, will be tested as chirally pure monoepoxydienes become available.
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    Structure-activity relationships for analogs of (+)-(E)-endo-Β-bergamoten-12-oic acid, an oviposition stimulant ofHelicoverpa zea (Boddie) (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 11-27 
    Details
    ISSN: 1573-1561
    Keywords: Oviposition ; insect chemoreception ; corn earworm ; Helicoverpa zea ; Lepidoptera ; Noctuidae ; Lycopersicon hirsutum ; host-plant selection ; sesquiterpenes ; carboxylic acids
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Β-Bergamotenoic acid, a compound previously shown to stimulate oviposition inH. zea, was converted into a set of bicyclic analogs and tested with a set of acyclic side chain analogs to ascertain the molecular structure that maximizes insect behavioral response. While changes in the bicyclic ring elicited no variation in response, alteration in the side chain structure ofΒ-bergamotenoic acid resulted in significant changes in moth preference. Free rotation about the C-C bond proximal to the carboxylic acid group appears to be an important structural factor, since saturation of the side chain double bond significantly increased activity. The carboxylic acid group seems to be required for strong oviposition stimulation, since analogs lacking the carboxylic acid group exhibited no significant oviposition activity. Oviposition preference ofH. zea was also influenced by the length of the hydrocarbon chain to which the carboxylic acid is attached. While hexanoic acid was found inactive, the ovipositional preference for the heptanoic and octanoic acids was greatest for the one 8-carbon tested. This and other work suggest that carboxylic acids of specific chain lengths influence the oviposition behavior of bothHelicoverpa andHeliothis species and may be associated with host-plant selection. The potential use of this information in designing integrated pest management strategies for control ofH. zea is discussed.
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    Effect of relative humidity conditions on responsiveness of European corn borer (Ostrinia nubilalis) males to female sex pheromone in a wind tunnel (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 61-69 
    Details
    ISSN: 1573-1561
    Keywords: European corn borer ; Ostrinia nubilalis ; Lepidoptera ; Pyralidae ; male responsiveness ; relative humidity ; wind tunnel
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The responsiveness pf 3-day-old European corn borer males to three concentrations of 97∶3 Z∶E 11-tetradecenyl acetate, the female sex pheromone, was studied over a range of relative humidities (43–100%) in a wind tunnel. The proportion of males taking flight and reaching the source decreased, while the proportion exhibiting in-flight arrestment of upwind progress increased under high humidity conditions at all three concentrations of pheromone tested. The relationships between relative humidity and these behaviors were best described by polynomial equations.
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    Effects of α-Terthienyl on the midgut detoxification enzymes of the European corn borer,Ostrinia nubilalis (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 2047-2054 
    Details
    ISSN: 1573-1561
    Keywords: Ostrinia nubilalis ; European corn borer ; Pyralideae ; Lepidoptera ; cytochrome P-450 ; cytochrome b5 ; cytochromec reductase ; glutathioneS-transferase ; α-terthienyl ; phototoxin
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The biochemical basis for the tolerance of the European corn borer,Ostrinia nubilalis, to the phototoxinα-terthienyl was investigated by measuring the midgut polysubstrate monooxygenases and glutathioneS-transferase activities.α-Terthienyl administered in the diet to the corn borers increased the level of cytochromeb 5, NADH-cytochromec reductase,O-demethylase, and glutathioneS-transferase activities. The induced detoxification enzyme activities should enable the corn borer to metabolizeα-terthienyl more efficiently and therefore render the corn borer highly tolerant toα-terthienyl.
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    Chemical and ultrastructural analysis of corn cuticular lipids and their effect on feeding by fall armyworm larvae (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 2055-2074 
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    ISSN: 1573-1561
    Keywords: Spodoptera frugiperda ; Lepidoptera ; Noctuidae ; Zea mays ; scanning electron microscopy ; cuticular lipids ; host-plant resistance
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The cuticular lipid composition of lower and upper leaves of five genotypes of field-grown corn,Zea mays L., was determined by combined gas chromatography-mass spectrometry. Surface lipids of the upper leaves had a higher proportion ofn-alkanes (45–52%) than the lower leaves, while the lower leaves had higher percentages of fatty alcohols (12–18%) than the upper leaves. Scanning electron microscopy showed that the upper leaves of two corn genotypes, MpSWCB-4 and Cacahuacintle X's, had a smooth amorphous appearance, while the lower leaves had a dense array of wax crystals.Spodoptera frugiperda (J.E. Smith) larvae weighed more and developed more rapidly when they were reared on diet containing corn foliage from which the cuticular lipids had been removed than when they were fed untreated foliage. However, growth was not inhibited when larvae were fed diet containing the cuticular lipid extracts or individual cuticular lipid components.
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    C18 Dienes as attractants for eighteen clearwing (Sesiidae), tineid (Tineidae), and choreutid (Choreutidae) moth species (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 799-813 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Sesiidae ; Tineidae ; Choreutidae ; (E2,Z13)-octadecadien-1-ol/acetate ; 3,13-octadecadien-1-ol/acetate ; isomers ; stereoselective synthesis ; sex attractants ; inhibitors ; field trapping
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract By screening singly and binary mixed 2,13- and 3,13-octadecadien-yl acetates and alcohols (2,13- and 3,13-18: Ac/OH)in Lithuania, Armenia, Azerbaijan, Turkmenistan, Ukraine, and the far east of Russia, sex attractants were discovered for 12 Sesiidae, four Tineidae, and one Choreutidae moth species. Males ofSesia yezoensis andBembecia puella as well asNemapogon flavifrons were attracted by mixture ofZ3,Z13-18:Ac/OH in a ratio of 9∶1,Pyropteron sp. n. by the same mixture (ratio 1∶9),Bembecia romanovi andB. zuwandica byZ3,Z13-18:Ac andE3,Z13-18:Ac (9∶1),Synanthedon caucasicum by the same mixture in the opposite ratio (1∶9),B. scopigera by 23,213-18:Ac andE2,Z13-18:OH in a ratio 9∶1,Synasphecia triannuliformis byZ3,Z13-18:OH andE3,Z13-18:OH (9∶1),Similipepsis takizawai andArchimeessia sp. n. by E3,Z13-18:OH andE2,Z13-18:Ac (1∶1),Prochoreutis sechestediana by a mixture ofE3,Z13-18:Ac plusE2,Z13-18:OH (1∶),Microsphecia brosiformis by E3,Z13-18:Ac,Synanthedon conopiformis by the analogous alcohol,Synanthedon scoliaeformis andNemaxera betulinella byE2,Z13-18:Ac,Triaxomera fulvimitrella byZ3,Z13-18:Ac. An analogous alcohol component is essential for the attraction ofB. ichneumoniformis males. Inhibitors forB. romanovi, B. scopigera andB. zuwandica attraction were discovered. Preliminary data on attractants for six other species as well as on the diurnal rhythm of sexual activity of three species are presented. A new method for the stereoselective synthesis of 3,13–18:Ac/OH andE2,Z13-18:Ac/OH is described.
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    Oviposition stimulants for the black swallowtail butterfly: Identification of electrophysiologically active compounds in carrot volatiles (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 919-937 
    Details
    ISSN: 1573-1561
    Keywords: Papilio polyxenes ; Papilionidae ; Lepidoptera ; Daucus carota ; Apiaceae ; host-plant selection ; oviposition behavior ; electroantennogram ; combined GC-EAG ; plant volatiles ; sabinene hydrate ; 4-terpineol ; bomyl acetate ; (Z)-3-hexenyl acetate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Headspace volatiles were collected from undamaged foliage of carrot,Daucus carota, a host-plant species of the black swallowtail butterfly,Papilio polyxenes. The volatiles were fractionated over silica on an open column, and the fractions were tested in behavioral assays withP. polyxenes females in laboratory experiments. The polar fractions, as well as the total mixture of volatiles, increased the landing frequency and the number of eggs laid on model plants with leaves bearing contact-oviposition stimulants. The nonpolar fraction, containing the most abundant compounds in carrot odor, was not stimulatory. Gas Chromatographic (GC) separation of the fractions was coupled with electroantennogram (EAG) recordings to identify the compounds perceived byP. polyxenes females. The EAG activity corresponded to the behavioral activity of the fractions. None of the nonpolar compounds, identified as various monoterpenes, evoked a major EAG response, but several constituents of the polar fractions elicited high EAG responses. Sabinene hydrate (both stereoisomers), 4-terpineol, bomyl acetate, and (Z)-3-hexenyl acetate were identified by GC-MS as active compounds.
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    Quantification of insect growth and its use in screening of naturally occurring insect control agents (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 1109-1118 
    Details
    ISSN: 1573-1561
    Keywords: Bioassay ; tobacco budworm ; Heliothis virescens ; beet armyworm ; Spodoptera exigua ; Lepidoptera ; Noctuidae ; insect growth inhibitors ; allelochemicals ; quassinoids ; chaparrin ; chaparrinone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract In studies of the effects of allelochemicals or other factors on the development of different insect species, comparison of growth-inhibiting activities is difficult using the parameters currently employed. We introduce two new parameters, growth index (GI) and relative growth index (RGI), which can unify the quantification of insect development. This quantification can also eliminate the effects of different growth characteristics due to the genetic differences between insect species. By measuring growth-inhibiting effects of two phytochemicals, chaparrin and chaparrinone, on the tobacco budworm,Heliothis virescens, and the beet armyworm,Spodoptera exigua, bioassay procedures and GI and RGI calculations are demonstrated.
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    Chirality of 5,11-dimethylheptadecane, the major sex pheromone component of the hemlock looper,Lambdina fiscellaria (Lepidoptera: Geometridae) (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 1057-1062 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Geometridae ; eastern hemlock looper ; western hemlock looper ; sex pheromone ; pheromone chirality ; dimethylated hydrocarbons ; field trapping ; electrophysiological recordings ; (5R, 11S)-5 ; 11-di-methylheptadecane ; (55,11R-5 ; 11-dimethylheptadecane ; (5R, 11R-5 ; 11-di-methylheptadecane ; (5S,11S)-5 ; 11-dimethyIheptadecane
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Of the four possible stereoisomers of 5,11-dimethylheptadecane, the major sex pheromone component of the eastern hemlock looper (EHL),Lambdina fiscellaria fiscellaria Guen., and the western hemlock looper (WHL),Lambdina fiscellaria lugubrosa Hulst, (5R,11S)-5,11-dimethylheptadecane was the only stereoisomer eliciting electrophysiological responses by male EHL and WHL antennae. In field bioassays with EHL and WHL populations, traps baited with (5R,11S)-5, 11-dimethylheptadecane caught as many males as did traps baited with all four stereoisomers combined or a synthetic mixture of 5,11-dimethylheptadecanes. Catches in traps baited with the other three stereoisomers did not significantly differ from those in the unbaited control traps. We conclude that male antennae lack chemoreceptors for the other three stereoisomers of 5,11-dimethylheptadecane and hypothesize that only (5R,115)-5,11-dimethylheptadecane is produced by female EHLs and WHLs.
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    Chemical correlates of α-tocopherol (Vitamin E) alteredMalacosoma disstria herbivory inFraxinus pennsylvanica var.Subintegerrinia, green ash (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 1205-1217 
    Details
    ISSN: 1573-1561
    Keywords: α-Tocopherol ; vitamin E ; elicitor ; alterable resistance ; antiherbivory ; ash tree ; Malacosoma disstria ; forest tent caterpillar ; Lepidoptera ; Lasiocampidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The antioxidant α-tocopherol (vitamin E), applied in a basal trunk band to the green ash tree,Fraxinus pennsylvanica var.subintergerrinia, elicited an alteration of foliar feeding byMalacosoma disstria larvae (Lepidoptera: Lasiocampidae). The bioassayed effects were dependent on the dosage of elicitor, the time after elicitation, and the position in the tree. Leaves for chemical analysis were collected from trees receiving two dosages and at two intervals after elicitation. Compounds in the ethyl acetate extractables from the ash tree leaves were separated by TLC and HPLC. TLC separations showed differences in the nonhydrolyzed extractables attributable to elicitor dosage and time after elicitation. TLC-resolved differences were also evident among acid-hydrolyzed samples. HPLC-resolved profiles revealed eight peaks in the nonhydrolyzed extractables that were quantitatively negatively correlated with larval feeding preference between elicited versus control foliage on at least one of the two sampling dates. Results from this study and other investigations reported in the literature indicate that the antioxidantα-tocopherol (vitamin E) can function as an environmental-stress elicitor of alterable defensive chemistry in green ash and other plants.
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    3,13-Dimethylheptadecane: Major sex pheromone component of the western false hemlock looper,Nepytia freemani Munroe (Lepidoptera: Geometridae) (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 1501-1510 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Geometridae ; sex pheromone ; 3,13-dimethylheptadecane ; 3,13-dimethylhexadecane ; 3, 13-dimethyloctadecane ; 5,13-dimethylheptadecane ; 3,11 -dimethylhexadecane ; 3, 11-dimethylpentadecane
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract 3,13-Dimethylheptadecane (3,13-dime-17Hy) is the major sex pheromone component of the western false hemlock looper (WFHL),Nepytia freemani Munroe. It was identified in extracts of female pheromone glands by coupled gas chromatographic-electroantennographic detection (GC-EAD) and coupled GC-mass spectroscopy (GC-MS). Traps baited with 100μg of 3,13-dime-17Hy attracted large numbers of male WFHL. Of five additional candidate pheromone dimethylated hydrocarbons, only 3,13-dimethylhexadecane attracted male WFHL. However, neither 3,13-dime-16Hy nor the other four compounds enhanced attraction to 3,13-dime-17Hy when tested in binary or ternary combination at respective ratios of 100∶10, 100∶1, or 100∶1∶1. Identification of the complete WFHL sex pheromone requires structural elucidation of all 12 EAD-active components in gland extracts, determination of their chirality, and field testing of antennally active isomers in appropriate combinations and ratios. Stereoisomeric 3,13-dime-17Hy as trap bait may already be used to monitor WFHL populations.
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    Determination of release rates of pheromone dispensers by air sampling with C-18 bonded silica (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 2513-2519 
    Details
    ISSN: 1573-1561
    Keywords: Sex pheromone ; release rate ; pheromone dispenser ; mating disruption ; Lobesia botrana ; Cydia pomonella ; Lepidoptera ; Tortricidae ; (E,E)-8,10-dodecadien-l-ol ; (E,Z)-7,9-dodecadienyl acetate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Release rates of pheromones from commercial dispensers for mating disruption inLobesia botrana andCydia pomonella have been measured by sampling an air stream with C-18 bonded silica (Sep-Pak cartridges) followed by extraction and gas chromatographic analysis. The flow chamber is made from inexpensive materials that can be replaced when contaminated. The results correspond with those obtained by gravimetry; the method supplies additional information on the composition of the airborne material.
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    Interactions amongHeliothis virescens larvae, cotton condensed tannin and the CryIA(c) δ-endotoxin ofBacillus thuringiensis (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 2485-2499 
    Details
    ISSN: 1573-1561
    Keywords: Bacillus thuringiensis subsp.kurstaki strain HD-73 ; insecticidal proteins ; cotton condensed tannin ; Heliothis virescens ; Lepidoptera ; Noctuidae ; relative growth rate ; relative consumption rate ; bioassays ; Gossypium hirsutum ; tritrophic interactions
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The potential interactions among a plant-produced allelochemical, a phytophagous insect, and an endotoxin produced byBacillus thuringiensis were investigated using purified cotton condensed tannins, the CryIA(c)δ-endotoxin fromB. thuringiensis subsp.kurstaki strain HD-73, and larvae ofHeliothis virescens. Purified condensed tannin from cotton fed to neonateH. virescens reduced feeding and mortality caused by insecticidal crystals ofB. thuringiensis. In fifth instars, tannin reduced relative growth rate (RGR), relative consumption rate (RCR), but antagonized the effects of the crystalδ-endotoxin. Tannin did not deter feeding of fifth instars in choice tests with cellulose-ester disks. Masking tannin from interacting with the dietary ingredients of artificial diets and crystal protein by encapsulation in alginate gel suggested that tannin adversely affected feeding after ingestion.These results suggest that insect control tactics that employδ-endotoxins in microbial insecticides and transgenic cotton plants may not be compatible when used in conjunction with plants containing high tannin concentrations.
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    URL: http://dx.doi.org/10.1007/BF00980685
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    Evidence for a multicomponent sex pheromone inEriborus terebrans (Gravenhorst) (HYM.: Ichneumonidae), a larval parasitoid of the European corn borer (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 2563-2576 
    Details
    ISSN: 1573-1561
    Keywords: Sex pheromone ; multicomponent pheromone ; parasitoid ; bioassay ; Hymenoptera ; Ichneumonidae ; Eriborus terebrans ; Lepidoptera ; Pyralidae ; Ostrinia nubilalis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Sex pheromone activity ofEriborus terebrans (Gravenhorst) (Hymenoptera: Ichneumonidae) was recovered from acetone rinses of flasks that previously contained females. The acetone flask rinses elicited the following male responses: upwind anemotaxis, casting, hovering, landing, wingfanning, and mating attempts with other nearby males. Activity of the acetone flask rinse lasted up to four days on a glass substrate. Polar component and nonpolar components were demonstrated in the acetone flask rinse. The polar component elicited male behavioral responses similar to those by the acetone flask rinse, although retention of males at the pheromone source and the period of wing-fanning were of shorter duration. Chromatography data and chemical derivatization indicated that the polar component had the properties of a carboxylic acid with an additional oxygen-containing functional group. The non-polar component acted as a synergist since it was inactive alone but increased male behavioral responses when added to the polar component. Florisil open column chromatography suggested that the nonpolar component was a hydrocarbon(s).
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    Chirality of synergistic sex pheromone components of the western hemlock looperLambdina fiscellaria lugubrosa (HULST) (Lepidoptera: Geometridae) (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 2547-2561 
    Details
    ISSN: 1573-1561
    Keywords: Sex pheromone ; enantiomer ; Lepidoptera ; Geometridae ; western hemlock looper ; (5R)-2,5-dimethylheptadecane ; (5S)-2,5-dimethylheptadecane ; (7R)-7-methylheptadecane ; (7S)-7-methylheptadecane ; chirality
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Bakers' yeast reduction of (2E)-3-(2′-furanyl)-2-methyl-2-propenal yielded the synthetic intermediate, (2S)-3-(2′-furanyl)-2-methylpropanol, of high chiral purity (〉97% ee) for the synthesis of the enantiomers of 2,5-dimethylheptadecane and 7-methylheptadecane, two synergistic sex pheromone components of the western hemlock looper (WHL),Lambdina fiscellaria lugubrosa Hulst. In electrophysiological bioassays, (7S)- but not (7R)-7-methylheptadecane elicited strong antennal responses by male WHL antennae. In field trapping experiments, addition of (7S)- but not (7R)-7-methylheptadecane to (5R,11S)-5,11-dimethylheptadecane, the major sex pheromone component of WHL, increased attraction. Attraction to (5R,11S)-5,11-dimethylheptadecane in combination with (7S)-7-methyiheptadecane was further enhanced by the addition of (5S)- but not (5R)-2,5-dimethylheptadecane. Similarly, attraction to (5R,11S)-5,11-dimethylheptadecane combined with (5S)-2,5-dimethylheptadecane increased when 7S- but not (7R)-7-methylheptadecane was added as a third component. We conclude that (7S)-7-methylheptadecane and (5S)-2,5-dimethylheptadecane are the synergistic sex pheromone components of WHL. The synthetic methodology described is applicable to the synthesis of chiral methyl-branched pheromones in other orders of the Insecta, particularly Coleoptera, Diptera and Orthoptera.
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    Species discrimination in five species of winter-flying geometrids (Lepidoptera) based on chirality of semiochemicals and flight season (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 2721-2735 
    Details
    ISSN: 1573-1561
    Keywords: Chirality ; enantiomers ; sex pheromones ; (3Z,9Z)-(6R,7S)-epoxynonadecadiene ; (3Z,9Z)-(6S,7R)-epoxynonadecadiene ; (6Z,9Z)-(3S,4R)-epoxynonadecadiene ; Colotois pennaria ; Erannis defoliaria ; Agriopis aurantiaria ; A. marginaria ; A. leucophearia ; Lepidoptera ; Geometridae ; electroantennogram ; field trapping
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Enantiomer separation of (6Z,9Z)-cis-3,4-epoxynonadecadiene and (3Z,9Z)-cis-6,7-epoxynonadecadiene could be achieved using chiral high-resolution gas chromatography and a cyclodextrin-bond column. (3Z,9Z)-(6R,7S)-Epoxynonadecadiene was identified from ovipositor extracts ofColotois pen-Naria, while inErannis defoliaria the 6S,7R-enantiomer was found. In field trapping tests pure synthetic enantiomers caught only conspecific males of these species. (3Z,6Z,9Z)-Nonadecatriene was found in both species, while the presence of (3Z,6Z,9Z)-heneicosatriene was indicated inC. Pennaria only. A 10∶10∶3 blend of (3Z,9Z)-(6R,7S)-epoxynonadecadiene, (3Z,6Z,9Z)-heneicosatriene, and (3Z,6Z,9Z)-nonadecatriene was found to be optimal for catchingC. Pennaria, whileE. Defoliaria males were optimally caught by a 1∶1 mixture of (3Z,9Z)-(6S,7R)-epoxynonadecadiene and (3Z,6Z,9Z)-nona-decatriene. (6Z,9Z)-(3S,4R)-Epoxynonadecadiene was identified from ovipositor extracts ofAgriopis (Erannis) aurantiaria. In field tests the pure enantiomer proved to be a highly specific sex attractant for both the late autumn/early winter flyingA. Aurantiaria and the late winter/early spring flyingA. Leucophearia. Males ofAgriopis marginaria, which fly in late winter/early spring, were attracted to (3Z,9Z)-(6S,7R)-epoxynonadecadiene. The addition of (3Z,6Z,9Z)-nonadecatriene to theS,R-enantiomer increased captures. Optimal catches were recorded with a 10∶3 epoxide-hydrocarbon blend. Enantiomer specificity in all species was confirmed in EAG measurements.
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    Developmental inhibition ofSpodoptera litura (Fab.) larvae by a novel caffeoylquinic acid from the wild groundnut,Arachis paraguariensis (Chod et Hassl.) (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 2917-2933 
    Details
    ISSN: 1573-1561
    Keywords: Spodoptera litura ; Lepidoptera ; Noctuidae ; Arachis paraguariensis ; wild groundnuts ; caffeoylquinic acids ; resistance ; rutin ; quercetin ; phenolics ; growth inhibition ; Arachis hypogaea
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A novel compound, 1-caffeoyl-4-deoxyquinic acid (1-CdQA) has been identified along with 3-caffeoylquinic acid (3-CQA) and 5-caffeoylquinic acid (5-CQA) (syn. chlorogenic acid) in the foliage ofArachis paraguariensis, a wild species of groundnut that is highly resistant to attack by the larvae ofSpodoptera litura. When neonate larvae were fed on diets treated with 3-CQA or 1-CdQA, their development was severely inhibited compared to larvae on untreated diets, and the effects were similar in nature and magnitude to those observed for larvae feeding on diets treated with 5-CQA, rutin, and quercetin. The effects of all the compounds were dose related, and their optimal concentration was approximately 3 mM, which corresponds to the total foliar concentration of both caffeoylquinic acids and quercetin diglycosides inA. paraguariensis. After 24 h, the development of third stadium larvae feeding on diets treated with 5-CQA, rutin and 1-CdQA was promoted compared to larvae on control diets, but after 96 hr larvae feeding on treated diets had gained significantly less weight than those on the control diets. 1-CdQA, 3-CQA, and quercetin dyglycosides (previously identified in the foliage ofA. paraguariensis) are considered to be valuable components in resistance of groundnuts toS. litura and may provide useful genetic markers in future breeding for resistance to this pest.
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    Sugar beet crown borer,Hulstia undulatella (Clemens) 1: Identification and field tests of female sex pheromone gland components (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 433-440 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Pyralidae ; Phycitinae ; Hulstia undulatella ; sex pheromone ; (Z)-9-tetradecen-1-ol acetate ; (Z)-9-tetradecen-1-ol ; (Z)-11-hexa-decen-1-ol acetate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Electroantennogram profiles of saturated and monounsaturated 12-, 14-, and 16-carbon acetates, and 12- and 14-carbon alcohols implicated (Z)-9-tetradecen-1-ol acetate (Z9-14: Ac) as a component of the female sex pheromone ofHulstia undulatella (Clemens). Gas chromatography-mass spectrometric analysis of extract of the female sex pheromone glands showed the presence of Z9-14:Ac (8.5 ng/female), (Z)-9-tetradecen-1-ol (Z9-14:OH), and (Z)-11-hexadecen-1-ol acetate (Z11-16:Ac) in a ratio of 100∶4∶21, respectively. In tests in sugar beet fields, Z9-14:Ac alone produced some trap catch. Addition of Z9-14: OH did not increase catch while addition of Z11-16:Ac eliminated catch, but addition of both Z9-14:OH and Z11-16: Ac increased catch sevenfold. A combination of Z9-14: OH and Z11-16: Ac without Z9-14: Ac did not produce trap catch. A lure of 200 μg Z9-14:Ac+16 μg Z9-14:OH+42 μg Z11-16:Ac is suggested for use in monitoring traps.
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    Trail following and recruitment: Response of eastern tent caterpillarMalacosoma americanum to 5β-cholestane-3,24-dione and 5β-cholestan-3-one (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 449-457 
    Details
    ISSN: 1573-1561
    Keywords: 5β-Cholestane-3 ; 24-dione ; 5β-cholestan-3-one ; trail following ; recruitment ; eastern tent caterpillar ; Malacosoma americanum ; Lepidoptera ; Lasiocampidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Studies were conducted to determine the relative effectiveness of 5β-cholestane-3,24-dione (diketone) and 5β-cholestan-3-one (monoketone) in eliciting trail following from eastern tent caterpillars,Malacosoma americanum. In Y maze tests, trails prepared from the monoketone were followed preferentially over diketone trails, even when the diketone trail was several orders of magnitude stronger. Under field conditions, colonies readily abandoned well-developed trail systems in favor of artificial trails that were established with the monoketone. Other tests in which the caterpillars selected trails prepared from the monoketone (but not the diketone) more often than their own recruitment trails indicate that the monoketone constitutes the chemical basis of recruitment communication in this insect. The study also shows that tent caterpillars are highly sensitive to small differences in the amount of monoketone in a trail and can distinguish between new and aged trails prepared from the compound.
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    Enantiomers of methyl substituted analogs of (Z)-5-decenyl acetate as probes for the chirality and complementarity of its receptor inAgrotis segetum 1: Synthesis and structure-activity relationships (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 459-484 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Noctuidae ; Agrotis segetum ; (Z)-5-decenyl acetate ; pheromone analog ; methyl substitution ; structure-activity ; single-sensillum recordings ; receptor interaction ; conformational analysis ; molecular mechanics ; enantiomers ; chirality
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The enantiomers of analogs of (Z)-5-decenyl acetate, a pheromone component ofAgrotis segetum, substituted by a methyl group in the 2, 3, 4, 7, and 8 positions and dimethyl substituted in the 4,7 positions, have been synthesized and studied by an electrophysiological single-cell technique and by molecular mechanics calculations. The results demonstrate that the electrophysiological activity as well as the ability of the (Z)-5-decenyl acetate receptor to differentiate between enantiomers depends on the position of the methyl substituent. For analogs methyl substituted in the 2, 4, or 8 position, no differences in the activities of the enantiomers could be observed. In contrast, the enantiomers of the 3- and 7-methyl analogs display a significant difference in the activities, theR-enantiomers being more active than theS-enantiomers. From an analysis of the structure-activity results of the enantiomers of the 4,7-dimethyl-substituted analogs, the chiral sense of the alkylchain of the natural pheromone component on binding to its receptor could be deduced.
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    Pheromone-mediated responses of male cabbage looper moths,Trichoplusia ni, following various exposures to sex pheromone or (Z)-7-dodecenol (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 503-515 
    Details
    ISSN: 1573-1561
    Keywords: Trichoplusia ni ; Lepidoptera ; Noctuidae ; sex pheromone ; behavioral inhibitor ; (Z)-7-dodecenol ; wind tunnel ; habituation ; adaptation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Prolonged preexposure (three days) of maleTrichoplusia ni to its six-component sex pheromone blend or its major pheromone component, (Z)-7-dodecenyl acetate, reduced subsequent upwind flight responses to a pheromone source. Preexposure to (Z)-7-dodecenol increased upwind flight responses to a pheromone source combined with (Z)-7-dodecenol. The impact of long-term preexposures was moderate when compared to the more immediate effects of background noise. When (Z)-7-dodecenyl acetate was presented as background noise, all maleT. ni failed to respond to a plume of the full pheromone blend. However, most moths succeeded in locking on to the pheromone plume and contacting the pheromone source in the presence of the five minor pheromone components as background noise. When (Z)-7-dodecenol was released as background noise the response rate to a pheromone source containing (Z)-7-dodecenol was increased dramatically. This indicates that males became adapted to (Z)-7-dodecenol while responding to the pheromone source. The results of this study indicate that both long-term preexposure treatments and immediate exposure to background noise can limit the ability of maleT. ni to respond to sex pheromone sources.
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    Fall armyworm sensitivity to flavone: Limited role of constitutive and induced detoxifying enzyme activity (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 645-667 
    Details
    ISSN: 1573-1561
    Keywords: Detoxification ; Spodoptera frugiperda ; Lepidoptera ; Noctuidae ; flavone ; induction ; polysubstrate monooxygenase ; glutathione transferase ; general esterase ; synergism
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract We used inhibition and induction of detoxifying enzymes to determine whether these enzymes allow a generalist species (Spodoptera frugiperda; fall armyworms) to cope with ingestion of the flavonoid, flavone. Flavone induces polysubstrate monooxygenases (PSMO), general esterases (GE), and glutathioneS-transferases (GST) inS. frugiperda, yet this species is affected deleteriously by low dietary concentrations of this allelochemical. First, in a series of experiments, larvae were fed artificial diets containing increasing concentrations of flavone, either alone or with known inhibitors of either PSMO, GE, or GST enzymes. In an additional treatment, flavone and inhibitors of all three enzyme systems were administered in diets simultaneously. PSMO and GE activities were reduced in vivo by their respective inhibitors, whereas that of GST was induced or unchanged. Significant synergism of flavone's growth-reducing activity occurred at the highest concentration tested (0.125% fresh mass, fm) when the PSMO inhibitor, piperonyl butoxide, or the GST inhibitor, diethyl maleate, was added to the diet, and at 0.08% fm flavone, when combined with the GE inhibitor, tri-tolyl phosphate. In many cases, however, the additive effect (i.e., reduction in growth owing to flavone alone + inhibitor alone) was greater than the synergistic effect, and no synergism occurred in the treatment with the three inhibitors combined. In the second approach, caterpillars were preexposed to a concentration of flavone (0.02% fm) that induced these enzymes ca. 1.5- to 2.5-fold, prior to switching larvae to a diet containing a higher (growth-reducing) flavone concentration (0.125% fm). The relative growth rates (RGR) of induced larvae were significantly greater (14%) than those of the uninduced larvae on the 0.125% fm flavone diet. Additionally, in two of the three experiments, relative consumption rate (RCR) was significantly greater (7–24%) in induced compared with uninduced larvae. The variable responses to inhibitor treatment and the relatively small benefit of enzyme induction suggest that these enzyme systems have minimal impact on the detoxification of flavone inS. frugiperda, even though this allelochemical induces enzyme activity and has been reported to be metabolized in vitro.
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    Iridoid glycoside sequestration byThessalia leanira (Lepidoptera: Nymphalidae) feeding onCastilleja integra (Scrophulariaceae) (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 1155-1166 
    Details
    ISSN: 1573-1561
    Keywords: Thessalia leanira fulvia ; Chlosyne leanira fulvia ; Lepidoptera ; Nymphalidae ; Castilleja integra ; Scrophulariaceae ; iridoid glycosides ; sequestration ; herbivory
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A small population of a polyvoltine checkerspot butterfly,Thessalia leanira fulvia (also known asChlosyne leanira ssp.fulvia), was found to useCastilleja integra as a larval food plant at a localized site (Burnt Mill) southwest of Pueblo, Colorado. Field-captured adult butterflies contained the major iridoid glycosides (catalpol and macfadienoside) of theCastilleja. The content of a third iridoid glycoside, methyl shanzhiside, was also relatively high in the collected butterflies even though most individualCastilleja plants at Burnt Mill contained little or no methyl shanzhiside. Only a few plants, restricted to a small area, did contain appreciable methyl shanzhiside. Most of the plants that lacked the ester methyl shanzhiside contained shanzhiside, the corresponding free carboxylic acid.Thessalia larvae did not normally methylate the acid to produce methyl shanzhiside. Larvae that stopped feeding at an early instar, but yet survived several weeks, did contain major amounts of methyl shanzhiside. It is suggested that only larvae that overwinter or otherwise enter diapause convert shanzhiside to methyl shanzhiside. TheCastilleja food plant also contained iridoids other than catalpol and macfadienoside, sometimes in major amounts, but these were never found in larvae, pupae, or butterflies.
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    Potential role of ascorbate oxidase as a plant defense protein against insect herbivory (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 1553-1568 
    Details
    ISSN: 1573-1561
    Keywords: Ascorbic acid ; ascorbate oxidase ; plant resistance ; plant defense ; oxidative stress ; Helicoverpa zea ; Lepidoptera ; Noctuidae ; cotton ; tomato ; soybean
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Ascorbic acid is essential for both nutritive and antioxidant functions in phytophagous insects; however, maintaining sufficient quantities of reduced ascorbate may be problematical for them. In this investigation, we show that the plant enzyme ascorbate oxidase retains activity in the digestive system of the herbivoreHelicoverpa zea. High levels of the enzyme are present in several host plants ofH. zea, including cotton, tomato, soybean, crimson clover, and vetch. The enzyme oxidizesL-ascorbic acid to dehydro-L-ascorbic acid, a potentially toxic product. The oxidation of ascorbic acid also produces active oxygen species such as the highly reactive hydroxyl radical. The nutritional quality of protein for larvalH. zea was significantly reduced by treatment with ascorbate and ascorbate oxidase. Oxidative damage to the protein was indicated by decreased lysine content, increased carbonyl formation, and the occurrence of protein fragmentation and polymerization. Furthermore, the oxidative loss of ascorbate in the herbivore's digestive system prevents ascorbate from functioning as an important antioxidant against a plethora of dietary prooxidants.
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    Aristolochic acids fromThottea spp. (Aristolochiaceae) and the osmeterial secretions of Thottea-feeding troidine swallowtail larvae (Papilionidae) (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 1587-1594 
    Details
    ISSN: 1573-1561
    Keywords: Aristolochic acid ; Aristolochiaceae ; Thottea ; osmeteria ; swallowtail butterfly ; Papilionidae ; Troides ; Pachliopta ; Lepidoptera ; defense
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Two aristolochiaceous plants in the genusThottea were shown to contain aristolochic acids. Larvae of two Malaysian troidine swallowtail butterflies,Troides (Troides) amphrysus andPachliopta (Losaria) neptunus, that fed onThottea leaves were found to sequester corresponding aristolochic acid analogs in the osmeterial glands.
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    Defensive secretion of two notodontid caterpillars (Schizura unicornis, S. badia) (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 2089-2104 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Notodontidae ; Schizura ; defensive secretion ; formic acid ; 2-tridecanone ; (5)-2-tridecanol ; 2-tridecyl formate ; 2-pentadecanone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The cervical gland secretion of larvae ofSchizura unicornis andS. badia (Lepidoptera: Notodontidae) contains formic acid, acetic acid, and a mixture of lipophilic compounds, including 2-alkanones, 2-alkanols, and formates of the alkanols. InS. unicornis, the secretion also contains severalω-monounsaturated analogs of the alcohols, ketones, and formates. The absolute configuration of two of the alcohols (2-tridecanol and 2-pentadecanol) was established asS in both species. The larvae spray their secretion when physically disturbed, aiming it accurately in the direction of the offending agent.
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    Toxicity of linear furanocoumarins toSpodoptera exigua: Evidence for antagonistic interactions (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 2473-2484 
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    ISSN: 1573-1561
    Keywords: Spodoptera exigua ; Lepidoptera ; Noctuidae ; psoralen ; 5-methoxypsoralen ; 8-methoxypsoralen ; furanocoumarins ; antagonistic toxicity ; plant-insect interactions ; Apium prostratum
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The linear furanocoumarins psoralen, bergapten, and xanthotoxin were tested for toxicity to the beet armywormSpodoptera exigua (Hübner) under short ultraviolet (UVB) radiation. Increased dietary concentrations of each furanocoumarin significantly decreased insect larval weight, extended generation time, and induced higher mortality. Xanthotoxin was the most toxic, followed by psoralen and bergapten. Combining psoralen with bergapten, xanthotoxin, or both resulted in significantly antagonistic effects on insect mortality. The combination of bergapten and xanthotoxin, however, produced additive effects. The implications of these observations forS. exigua resistance in the wild plant accession ofApium prostratum and the enigma the findings represent for plant-insect relationships are discussed.
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    URL: http://dx.doi.org/10.1007/BF00980684
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  • 91
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    Responses of maxillary sensilla styloconica inBombyx mori to glucosides fromOsmunda japonica, a nonhost plant (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 2501-2512 
    Details
    ISSN: 1573-1561
    Keywords: Bombyx mori ; Lepidoptera ; Bombicidae ; Noctuidae ; Spodoptera litura ; sensilla styloconica ; royal fern ; Osmunda japonica ; electrophysiological response
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract We isolated glucosides from the royal fern,Osmunda japonica, which elicit a deterrent response in larvae ofBombyx mori. These compounds were absent in taro (Colocasia antiquorum) and castor-oil plant (Ricinus communis) leaves and did not evoke responses of sensory cells in the lateral and medial sensilla styloconica ofSpodoptera litura. This glucoside extract of the royal fern leaves stimulates receptors generally associated with deterrent. It is also possible that this compound may act as a behavioral deterrent, and from actual feeding tests, it is suggested that this compound may prevent feeding in some monophagous insects, such asBombyx mori. The deterrent glucoside possesses a noncyclic aglycon.
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    URL: http://dx.doi.org/10.1007/BF00980686
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  • 92
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    Xanthine toxicity to caterpillars synergized by allopurinol, a xanthine dehydrogenase/oxidase inhibitor (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 2635-2650 
    Details
    ISSN: 1573-1561
    Keywords: Allelochemical ; allopurinol ; Anticarsia gemmatalis ; detoxification ; dose-response ; consumption rate ; food utilization ; Lepidoptera ; Noctuidae ; purine ; Spodoptera frugiperda ; synergism ; uric acid ; xanthine
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Xanthine (2,6-dioxypurine), which occurs in certain legumes and other plants, was fed in artificial diet to larvae of two noctuid moth species, a legume specialist,Anticarsia gemmatalis, and a generalist,Spodoptera frugiperda. In addition, diets either lacked or contained allopurinol (4-hydroxypyrazolo(3,4-d)-pyrimidine), an inhibitor of xanthine dehydrogenase and oxidase, enzymes that convert xanthine to uric acid. Xanthine alone (up to 2% fresh mass, fm) had little deleterious effect on either species, whereas allopurinol alone (up to 1% fm) had moderate but significant effects, increasing mortality, slowing development, and reducing insect biomass. At 0.5% fm allopurinol, the decrease in biomass-relative growth rate (RGR) was associated with reductions in the efficiency of conversion to biomass of digested food (ECD; both species) and in the biomass-relative consumption rate (RCR;A. gemmatalis). In addition, pupae of each species from allopurinol-fed larvae had increased water retention (i.e., lower percentage dry mass) compared with insects consuming control diet. When fed diet containing both compounds (1% fm xanthin+0.5% fm allopurinol), noA. gemmatalis and only 40% ofS. frugiperda larvae reached the prepupal stage; additionally for the latter species, there was a substantial slowing of growth and reductions in final biomass, RGR, RCR, and ECD. These results indicate a synergistic interaction, in which the effects of xanthine and allopurinol combined in the diet were significantly greater than the additive effects of each compound tested separately. Presumably, the inhibition of xanthine dehydrogenase by allopurinol prevented the absorbed xanthine from being converted to uric acid and excreted. In addition, this study expands the phenomenon of phytochemical detoxification by insects to include xanthine dehydrogenase, an enzyme generally not considered within this context.
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    URL: http://dx.doi.org/10.1007/BF00980697
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  • 93
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    Sex pheromone components of the fruit-tree leaf roller,Archips argyrospilus (Walker) (Lepidoptera: Tortricidae), in British Columbia (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 2855-2864 
    Details
    ISSN: 1573-1561
    Keywords: Archips argyrospilus ; fruit-tree leaf roller ; Lepidoptera ; Tortricidae ; sex pheromone ; (11Z)-tetradecen-1-ol acetate ; (11E)-tetradecen-1-ol acetate ; (9Z)-tetradecen-1-ol acetate ; dodecan-1-ol acetate ; (11Z)-tetradecen-1-ol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract In field experiments in the Okanagan Valley, British Columbia, the pheromone blend of (11Z)-tetradecen-1-ol acetate (Z11-14:OAc), (11E)-tetradecen-1-ol acetate (E 11-14:OAc), (9Z)-tetradecen-1-ol acetate (Z9-14:OAc) and dodecan-1-ol acetate (12: OAc) at a 100∶64∶2∶1 ratio (western FTLR blend) attracted significantly more male fruit-tree leaf roller (FTLR),Archips argyrospilus (Walker), than did the previously reported four-component blend and modifications thereof. Addition of (11Z)-tetradecen-1-ol (Z11-14:OH) to the western FTLR blend in a ratio of 4% relative toZ11-14: OAc further significantly enhanced attraction. Compounds were identified and their ratio determined by coupled gas chromatographic-electroantennographic (GC-EAD) and coupled GC-mass spectrometric analyses of female FTLR pheromone gland extracts and by retention index calculations of candidate pheromone components. Determination and use of geographically specific pheromonal blends may be required for optimal, semiochemical-based biorational control of FTLR and other lepidopteran orchard pests.
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    URL: http://dx.doi.org/10.1007/BF00980587
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  • 94
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    Induction of cytochrome P-450 activities by nicotine in the tobacco hornworm,Manduca sexta (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 2903-2916 
    Details
    ISSN: 1573-1561
    Keywords: Cytochrome P-450 ; induction ; nicotine ; Manduca sexta ; Lepidoptera ; Sphingidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The induction by dietary nicotine of a series of cytochrome P-450 enzyme activities was investigated in early fifth-instarManduca sexta larvae. At a low nicotine concentration in the diet (0.1 %), three of 12 midgut microsomal enzyme activities were significantly increased. At a higher concentration (0.75%) commonly found in plants of the genusNicotiana, nine of 12 activities were induced by 1.4- to 10.0-fold. Total cytochrome P-450, P-450 reductase activity, and midgut microsomal metabolism of nicotine were also increased by feeding 0.75% nicotine. Nicotine was metabolized by midgut microsomes to nicotine-1-N-oxide and cotinine-N-oxide. Fat body microsomal nicotine metabolism was low and unaffected by dietary nicotine. Isolated nerve cords were able to metabolize nicotine in vitro but this metabolism was not inducible by dietary nicotine. Nicotine-fed fifth-instarM. sexta larvae showed an increased tolerance to subsequent nicotine injection when compared to larvae fed a control diet. These results support the idea that induction of midgut cytochrome P-450-related metabolism is an adaptation ofManduca sexta to dietary nicotine.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00980591
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  • 95
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    A chemical basis for differential acceptance ofErysimum cheiranthoides by twoPieris species (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 195-210 
    Details
    ISSN: 1573-1561
    Keywords: Pieris rapae ; Pieris napi oleracea ; Lepidoptera ; Pieridae ; Erysimum cheiranthoides ; oviposition ; stimulants ; deterrents ; glucosinolates ; glucoiberin ; glucocheirolin ; cardenolides
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Wormseed mustard,Erysimum cheiranthoides, is unacceptable as a host for the cabbage butterfly,Pieris rapae. However, it is preferred for oviposition byPieris napi oleracea in the greenhouse. Isolation and identification of the oviposition stimulants toP. napi oleracea were accomplished by C18 open-column chromatography, TLC, ion-exchange chromatography, HPLC, UV, and NMR spectroscopy. Glucoiberin and glucocheirolin were identified as the most active stimulants. The extracted glucoiberin was as stimulatory as glucocheirolin, although its concentration in theErysimum plants was about 10 times lower than that of glucocheirolin. These glucosinolates were only weak stimulants toP. rapae. Furthermore,P. rapae was strongly deterred by the cardenolides, erysimoside and erychroside, fromE. cheiranthoides, andP. napi oleracea was less sensitive to these compounds. No other deterrent toP. napi oleracea was detected in this plant species. The results explain the differential acceptance ofE. cheiranthoides by these twoPieris species.
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    URL: http://dx.doi.org/10.1007/BF00993689
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  • 96
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    Influence of foliar glucosinolates in oilseed rape and mustard on feeding and growth of the bertha armyworm,Mamestra configurata Walker (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 249-266 
    Details
    ISSN: 1573-1561
    Keywords: Brassica campestris ; B. juncea ; B. napus ; Bertha armyworm ; canola ; glucosinolate ; insect-plant interactions ; isothiocyanate ; Mamestra configurata ; Lepidoptera ; Noctuidae ; mustard ; Sinapis alba ; thiocyanate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The relationship between host plant glucosinolate profile and feeding and growth of the Bertha armyworm,Mamestra configurata Walker was investigated using eight cultivated rape and mustard varieties. Mean larval weights of neonates reared on intact rosette-stage plants were significantly different on the different species in the orderBrassica juncea 〈Sinapis alba 〈B. napus 〈B. campestris. WhileB. juncea was least preferred,S. alba was significantly more attractive to neonate larvae in choice tests. Relative consumption and growth rates of fourth-instar larvae were also reduced onB. juncea foliage. Other differences were dependent on the plant growth stage. Neonate preference was not correlated to total glucosinolate levels, but rather to the concentrations of isothiocyanate-releasing glucosinolates. However, the relationship between consumption and glucosinolate levels was inconsistent. Relative growth rate was negatively correlated to total glucosinolate content for stage 3 and 4 foliage—mainly due to the concentration of isothiocyanatereleasing glucosinolates. The relative importance of isothiocyanate-releasing glucosinolates was verified by rearing neonates on meridic diets containing equimolar concentrations of sinigrin, its metabolite, allyl isothiocyanate, and indole-3-carbinol, metabolite of 3-indolylmethyl glucosinolate. Sinigrin and allyl isothiocyanate in the diet produced virtually identical negative weight vs. concentration regression lines. No such dose-response effect was observed with indole-3-carbinol. The data suggest that foliar isothiocyanate-releasing glucosinolates may provide some degree of plant protection from polyphagous insects.
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    URL: http://dx.doi.org/10.1007/BF00993693
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  • 97
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    Arrestant responses of southwestern corn borer larvae to free amino acids: Structure-activity relationships (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 301-311 
    Details
    ISSN: 1573-1561
    Keywords: Southwestern corn borer ; Diatraea grandiosella Dyar ; Lepidoptera ; Pyralidae ; corn ; Zea mays L. ; plant-insect interaction ; amino acids ; sugars ; herbivory ; feeding resistance
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The leaf-feeding resistance of corn or maizeZea mays L. to the southwestern corn borer, SWCB,Diatraea grandiosella Dyar has been attributed at least in part to decreased protein, increased crude fiber, and increased hemicellulose in the whorls of resistant genotypes. In this study, individual amino acids and sugars were evaluated as arrestants, with the objective of identifying those that gave weak or negative responses. Several structure-activity relationships were identified. Larvae responded to three-carbonn alkyl alpha amino acids more than to two-, four-, five-, and six-carbon compounds. Amino acids with terminal isopropyl functions gave decreased responses relative to theirn-alkyl counterparts. Dicarboxylic acids and their amides gave the lowest responses of all classes of amino acids. The normally occurring basic amino acids were all good arrestants. The guanido [HN:C(NH2)NH-] function was somewhat important to an arrestant response, as was the number of methylenes between the alpha and omega amino functions of diaminon-alkyl amino acids. Hydroxy amino acids were generally good arrestants unless the hydroxyl was located on a ring system. The two sugars present in expressed corn whorl juice, glucose and fructose, gave poor responses. However, two other sugars, mannose and arabinose, whose C-2 hydroxyls are conformationally in the axial position, were strongly arrestant. Formulated amino acid mixtures based on their content in whorl juice were as strong arrestants as whorl juice. However, the relative contributions of amino acids and sugars that are weak arrestants to the resistance of corn to SWCB larvae is uncertain because amino acid analyses did not reveal significantly higher contents of these amino acids in the whorl juices of resistant lines.
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    URL: http://dx.doi.org/10.1007/BF00993697
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  • 98
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    Detoxication activity in the gypsy moth: Effects of host CO2 and NO 3 − availability (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 357-367 
    Details
    ISSN: 1573-1561
    Keywords: Carbonyl reductase ; carbon dioxide ; cytochrome P-450 monooxygenase ; detoxication enzymes ; esterase ; global change ; glutathione transferase ; gypsy moth ; Lymantria dispar ; Lepidoptera ; Lymantriidae ; nitrate ; phytochemistry ; resource availability
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract We investigated the effects of host species and resource (carbon dioxide, nitrate) availability on activity of detoxication enzymes in the gypsy moth,Lymantria dispar. Larvae were fed foliage from quaking aspen or sugar maple grown under ambient or elevated atmospheric CO2, with low or high soil NO 3 − availability. Enzyme solutions were prepared from larval midguts and assayed for activity of cytochrome P-450 monooxygenase, esterase, glutathione transferase, and carbonyl reductase enzymes. Activity of each enzyme system was influenced by larval host species, CO2 or NO 3 − availability, or an interaction of factors. Activity of all but glutathione transferases was highest in larvae reared on aspen. Elevated atmospheric CO2 promoted all but transferase activity in larvae reared on aspen, but had little if any impact on enzyme activities of larvae reared on maple. High NO 3 − availability enhanced activity of most enzyme systems in gypsy moths fed high CO2 foliage, but the effect was less consistent for insects fed ambient CO2 foliage. This research shows that gypsy moths respond biochemically not only to interspecific differences in host chemistry, but also to resource-mediated, intraspecific changes in host chemistry. Such responses are likely to be important for the dynamics of plantinsect interactions as they occur now and as they will be altered by global atmospheric changes in the future.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00993701
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  • 99
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    Source of sex pheromone of the egg-larval parasitoid,Ascogaster reticulatus Watanabe (Hymenoptera: Braconidae) (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 963-969 
    Details
    ISSN: 1573-1561
    Keywords: Sex pheromone gland ; mating behavior ; Ascogaster reticulatus ; Hymenoptera ; Braconidae ; egg-larval parasitoid ; Adoxophyes sp. ; Lepidoptera ; Tortricidae ; tibia
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A sex pheromone ofAscogaster reticulatus Watanabe (Hymenoptera: Braconidae), identified as (Z)-9-hexadecenal, elicits males' antennal matesearching behavior. In order to localize the source of sex pheromone production, each body part was separated and extracted with hexane and then subjected to 9-cm Petri dish bioassay. The highest activity was found in thorax extract. Among legs, wings, and thorax, legs have the highest activity. Among fore, middle, and hind legs, hind legs have the highest activity. Among coxa and trochanter, femur, tibia, and tarsus, tibia has the highest activity. From these results, the presence of a tibial sex pheromone gland was suggested.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00992531
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  • 100
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    Sex pheromone of the western hemlock looper,Lambdina fiscellaria lugubrosa (Hulst) (Lepidoptera: Geometridae) (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 1009-1019 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Geometridae ; Lambdina fiscellaria fiscellaria ; Lambdina fiscellaria lugubrosa ; sex pheromone ; 5,11-dimethylheptadecane ; 2,5-dimethylheptadecane ; 7-methylheptadecane ; 5-methylheptadecane
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The sex pheromone of the western hemlock looper (WHL),Lambdina fiscellaria lugubrosa (Hulst), comprises three methylated hydrocarbons: 5,11-dimethylheptadecane (5,11), 2,5-dimethylheptadecane (2,5), and 7-methylheptadecane (7). Compounds extracted from female pheromone glands were identified by coupled gas chromatographic-electroantennographic (GC-EAD) analysis and coupled GC-mass spectroscopy in selected ion monitoring mode. In trapping experiments, (5,11) alone attracted male moths, but addition of either (7) or (2,5) significantly enhanced attraction. (5,11) combined with both (7) and (2,5) was significantly most attractive. (5,11) and (2,5) are also sex pheromone components of the eastern hemlock looper (EHL),Lambdina fiscellaria fiscellaria (Guen.). Although (7) is produced by the EHL, it is a pheromone component only in the WHL. It constitutes the first behaviorally active monomethyl-branched hydrocarbon to be found in a geometrid and is a novel lepidopteran sex pheromone component. The different 2- versus 3-component sex pheromone supports taxonomic division of EHL and WHL.
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    URL: http://dx.doi.org/10.1007/BF00992534
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