Towards the identification and synthesis of the sex pheromone of the citrus leafminer, Phyllocnistis citrella Stainton (Lepidoptera: Gracillariidae)

Parra-Pedrazzoli, Ana Lia; Cossé, Allard A.; Murata, Yasuhiro; Bento, José Maurício Simões; Vilela, Evaldo F.; Leal, Walter S.

doi:10.1590/s1519-566x2006000100003

Cited by 7 publications

(4 citation statements)

References 20 publications

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“…1). Responses of males in the olfactometer were similar to those observed for Phyllocnistis citrella (Gracillariidae) (Parra et al, 2002;Parra-Pedrazzoli et al, 2006) and suggested that the gland extracts elicit sexual attraction of males.…”

Section: Resultssupporting

confidence: 65%

Sex Pheromone of Lonomia obliqua: Daily Rhythm of Production, Identification, and Synthesis

et al. 2007

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The sex pheromone of Lonomia obliqua Walker (Lepidoptera: Saturniidae) was studied in the laboratory. All female calling occurred during the scotophase. Most females (70.6%) called first within 24 hr of eclosion. Calling varied with age of female, with older (5-to 6-day-old) females calling earlier in the scotophase and for longer durations than younger (0-to 1-day-old) females. The sex pheromone gland of 1-to 3-day-old virgin females was extracted during the calling peak. A Y-olfactometer bioassay showed significant attraction of males to a filter paper containing the female gland extract. Gas chromatographic-electroantennogram detection (GC-EAD) analysis of the extract indicated the presence of at least two possible pheromone components. Gas chromatographic-mass spectrometric analysis of the major GC-EAD-active peak indicated a hexadecenyl acetate; chemical derivatization indicated Δ11 unsaturation. Synthetic samples of (E)-and (Z)-11-hexadecenyl acetate were obtained by coupling 10-bromo-1-decanol and 1-hexyne, utilizing lithium chemistry. The comparison of the retention time of dimethyl disulfide derivatives of the natural compound, to those of synthetic chemicals, confirmed the natural compound as (E)-11-hexadecenyl acetate. The minor component was identified as the related alcohol, (E)-11-hexadecenol. The ratio of the two components in female extract was 100:35. Preliminary tests of males in a Y-olfactometer showed that their response to a mixture of the two compounds was not significantly different from that to gland extract.

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Section: Resultssupporting

confidence: 65%

Sex Pheromone of Lonomia obliqua: Daily Rhythm of Production, Identification, and Synthesis

et al. 2007

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“…The male attractivity towards females pheromone gland extracts in Y olfactometer was obtained for the citrus leafminer Phyllocnistis citrella (Lepidoptera: Gracillaridae) (Parra-Pedrazzoli et al 2006), and for Lonomia obliqua (Lepidoptera: Saturniidae) (Zarbin et al 2007a, b). Altogether, these data suggest the existence of a female-emitted sex pheromone and the single GC-EAD active component present in the gland extract is the putative sexual pheromone of the species.…”

Section: Discussionmentioning

confidence: 99%

Calling behaviour and male response towards sex pheromone of poplar moth Condylorrhiza vestigialis (Lepidoptera: Crambidae)

et al. 2008

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The calling behaviour of virgin females Condylorrhiza vestigialis Guenée, 1854 (Lepidoptera: Crambidae) and the female pheromone gland extract activity were studied under laboratory conditions. Most of the females started calling from their Wrst scotophase period after emergence. Maximum calling occurred between the seventh and tenth hours of the scotophase period. The length of the calling increased with age until the fourth scotophase, but the onset of calling time did not diVer with age. The number of calling bouts increased signiWcantly with age, but the mean duration of each calling bout (20.8 min) did not vary with age. Extracts of pheromone glands evaluated in a Y-tube olfactometer attracted signiWcantly more males than control, 70 and 30%, respectively. Gas chromatographic-electroantennogram detection (GC-EAD) analysis of these extracts indicated the presence of a single EAD-active peak, the putative sex pheromone of the species. This pheromone compound may be suitable for monitoring populations densities of C. vestigialis, and for detection of the onset of the seasonal Xight period. An eYcient pheromone is of importance also with respect to current attempts to develop new control methods for this important pest of Populus spp. in Brazil.

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“…The experiments were performed between the 4 th and 6 th hours of the scotophase, the time of day of highest pheromone release. Insects that did not choose any of the arms were excluded from statistical analysis 44,45 . Data were analyzed using a chi-square test processed on BioEstat software (version 5.0).…”

Section: Methodsmentioning

confidence: 99%

Isophorone derivatives as a new structural motif of aggregation pheromones in Curculionidae

Vidal

Moreira

Coracini

et al. 2019

Sci Rep

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The beetle Homalinotus depressus (Coleoptera: Curculionidae) is a major pest of coconuts in the Northern region of Brazil, for which environmentally friendly methods of control are desired. Behavioral responses of H. depressus to airborne volatile extracts from conspecifics suggested the presence of a male-produced aggregation pheromone. GC analyses of these extracts showed the presence of four male-specific compounds. Analytical data in combination with the synthesis of standards led to the identification of the male-released semiochemicals as epoxyisophorone (1), isophorone (2), homalinol (3), and 2-hydroxyisophorone (4), of which (3) was the major constituent. The configuration of homalinol was determined to be cis on the basis of retention times of synthetic cis and trans synthetic standards. Enantiomers of cis-homalinol were obtained in high enantiomeric excess by using biocatalysis. Their separation on a GC enantioselective column (β-Dex325®), allowed us to unambiguously determine that the absolute configuration of natural homalinol was (1R,2R,6S). Field bioassays demonstrated that both the synthetic major compound per se and mixtures of all four male-specific compounds were attractive to H. depressus.

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Towards the identification and synthesis of the sex pheromone of the citrus leafminer, Phyllocnistis citrella Stainton (Lepidoptera: Gracillariidae)

Cited by 7 publications

References 20 publications

Sex Pheromone of Lonomia obliqua: Daily Rhythm of Production, Identification, and Synthesis

Sex Pheromone of Lonomia obliqua: Daily Rhythm of Production, Identification, and Synthesis

Calling behaviour and male response towards sex pheromone of poplar moth Condylorrhiza vestigialis (Lepidoptera: Crambidae)

Isophorone derivatives as a new structural motif of aggregation pheromones in Curculionidae

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