Identification of sex pheromone components ofSpodoptera sunia Guenée (Lepidoptera: Noctuidae)

Moths belonging to the speciesSpodoptera sunia have been recognized as a new pest of cotton in Central America. By means of electro-physiologic investigations, solid sample injection gas chromatography, and combined gas chromatography-mass spectrometry, (Z)-9-tetradecenyl acetate, (9Z,12E)-9,12-tetradecadienyl acetate, (Z)-9-tetradecen-1-ol, and (Z)-11-hexadecenyl acetate, in a ratio of 10053120, were identified in the pheromone gland of female insects. These substances should serve as a base for the development of a pheromone-monitoring system for this lepidopteran pest.Pheromones, 60. Pheromones 59: Bestmann, HJ., Attygalle, A.B., Brosche, T., Erler, J., Platz, H., Schwarz, J., Vostrowsky, O., Wu Cai-Hong, Kaissling, K.E. and Chen Te-Ming. 1987. Z.Naturforsch. 42c:631–636.     

Behavioral activity of optical isomers of 5,9-dimethylheptadecane,the sex pheromone ofLeucoptera scitella L. (Lepidoptera: Lyonetidae)

Among the pure stereoisomers of 5,9-dimethylheptadecane, a previously identified sex pheromone component ofLeucoptera scitella L., only theS,S isomer yielded trap captures in the field. The addition of the other stereoisomers had no effect on cathes. The addition of low percentages of racemic 5,9-dimethylhexadecane, a previously identified minor component in the sex pheromone, did not influence trap catches or alter behavior of males approaching an attractant source in the field.     

Temporal patterns of sex pheromone titers and release rates inHolomelina lamae (Lepidoptera: Arctiidae)

Six hydrocarbon components (2-methylhexadecane,n-heptadecane, 2-methylheptadecane, 2-methyloctadecane,n-nonadecane, and 2-methylnonadecane) were identified in sex-pheromone gland extracts and in airborne collections ofHolomelina lamae. Low variability in the ratio of components among individuals indicates tight regulation of blend composition. Minor changes were evident in the quantity and ratio of the blend as a function of time of day. Based on gland extracts, the total quantity of the six components increased from day 1 (X = 6299 ng) to day 4 (X = 7498 ng) and subsequently decreased. No significant correlations were found between total gland contents and wet or dry weights of moths. Emission rates ofH. lamae females were determined from pheromone adsorbed onto Porapak Q. Quantities released peaked shortly after the onset of calling and decreased rapidly as calling continued. Peak release rates ranged from 13 to 350 ng/10 min, and from 37 to 835 ng/60 min. Noncalling females did not emit detectable quantities of pheromone. Based on release rates and the rate of pulsation of the abdominal tip, the average amount released per pulse is not constant. The mean ratio of components released (0.787.45 84.802.842.591.53) was not very different from the ratio of components in gland extracts of 2-day-old females (0.704.1990.12 1.651.911.42). We propose that the blend is atomized rather than volatilized from the gland, thus retaining nearly the same ratios in the female's effluvium as in her gland.     

Female sex pheromone components ofHeliothis peltigera (Lepidoptera: Noctuidae)

Ten compounds were found in the sex pheromone glands ofHeliothis peltigera (Schiff) and identified as tetradecenal, (Z)-9-tetradecenal, (Z)-9-tetradecenol, (Z)-9-tetradecenyl acetate, hexadecanal, (Z)-7-hiexadecenal, (Z)-9-hexadecenal, (Z)-11-hexadecenal, (Z)-11-hexadecenol, and (Z)-11-hexadecenyl acetate. Behavioral tests in a wind tunnel and subsequent trapping studies conducted in the field indicated that (Z)-11-hexadecenal and (Z)-9-tetradecenal are the main pheromone components ofH. peltigera. Addition of (Z)-11-hexadecenol to the binary blend did not enhance the capture of males ofH. peltigera, but it decreased the number of males of the sympatricH. armigera. Rubber septa impregnated with a mixture of 2 mg (Z)-11-hexadecenal + 1 mg (Z)-9-tetradecenal + 0.6 mg (Z)-11-hexadecenol are recommended for monitoringH. peltigera. Contribution from the Agricultural Research Organization (ARO), No. 2454-E, 1988 series.     

Evidence for presence and nature of female sex pheromone ofBrithys crini fabricius (Lepidoptera: Noctuidae)

The existence of a female sex pheromone of the noctuid mothBrithys crini Fabricius was confirmed in both laboratory bioassay and field tests. Crude extracts and airborne volatiles from females were analyzed by gas chromatography and mass spectrometry and the data compared with authentic compounds. The primary sex pheromonal compound was Z11-16: Ald. Scanning electron microscopy showed that the external surface of the sex pheromone gland was covered with folds that might increase the sex pheromone evaporation area.     

Identification of a sex pheromone ofHeliothis subflexa (GN.) (Lepidoptera: Noctuidae) and field trapping studies using different blends of components

Eight compounds were isolated from the sex pheromone gland ofHeliothis subflexa (Gn.) and identified as hexadecanal, (Z)-9-hexadecenal, (Z)-11-hexadecenal, (Z)-7-hexadecen-1-ol acetate, (Z)-9-hexadecen-1-ol acetate, (Z)-11-hexadecen-1-ol acetate, (Z)-9-hexadecen-1-ol, and (Z)-11-hexadecen-1-ol. Although the whole blend was found to be an effective male attractant, the deletion of alcohols from the blend increased trap captures considerably. Further, although the binary mixture of (Z)-9-hexadecenal and (Z)-11-hexadecenal caught some maleH. subflexa, significant increases in captures were noted when the three acetate components were included in the blend.Mention of a commercial or proprietary product in this paper does not constitute an endorsement of that product by the USDA or the State of Florida.     

Evidence for (E,Z)-8,10-dodecadienyl acetate as the major component of the sex pheromone of the eastern pine seedworm,Cydia toreuta (Lepidoptera: Tortricidae)

The sex pheromone ofCydia toreuta (Grote), the eastern pine seedworm, was investigated using electroantennogram (AG) measurements, gas chromatography (combined GC-FID-EAD) measurements, and field tests. (E,Z)-8,10-dodecadienyl acetate (E,Z8,10-12:Ac) and (E,E)-8,10-dodecadienyl actetate (E,E8,10-12: Ac) produced both the highest EAG and EAD responses. Only a single antennal stimulatory peak was observed when female abdominal tip extracts were analyzed by GC-FID-EAD, which corresponded exactly with that of authenticE,Z8,10-12: Ac. Field tests confirmedE,Z8,10-12: Ac as the major pheromone component. TheE,Z isomer by itself caught equivalent numbers of male moths as did caged females. The addition of theE,E isomer to theE,Z form increased trap catch, although not significantly (P = 0.05). The addition of (Z,Z)-8,10-dodecadienyl acetate to theE,Z isomer significantly (P=0.05) reduced trap catch, while the addition of (Z,E)-8,10-dodecadienyl acetate to theE,Z form also decreased trap catch, but not significantly (P=0.05).     

(E)-11,13-tetradecadienal: Major sex pheromone component of the eastern blackheaded budworm,Acleris variana (Fern.) (Lepidoptera: Tortricidae)

(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.     

Identification of female sex pheromone components of rice looper,Plusia festucae (L.), (Lepidoptera: Noctuidae)

The rice looper,Plusia festucae, is a defoliator of the rice plant. Chromatographic behavior, chemical reactions, and GC-MS analyses of the female sex pheromone revealed that the main component was (Z)-5-dodecenyl acetate (Z5–12: OAc, component I). The GC-MS analysis also indicated that the pheromone gland extract included another three monounsaturated components, (Z)-5-dodecen-l-ol (Z5–12: OH, component II), (Z)-7-tetradecenyl acetate (Z7–14: OAc, component III), and (Z)-7-tetradecen-l-ol (Z7–14: OH, component IV) in the following ratio: I:II:III:IV=100:6:15:1. In a paddy field, the mixture of synthetic I, II, and III in a ratio of 100:6:15 showed stronger attractancy than the virgin female, while the role of IV was unknown.     

Identification of sex pheromone of tomato pinworm,Keiferia lycopersicella (Wals.)

A sex pheromone produced by femaleKeiferia lycopersicella (Walsingham) was isolated and identified as (E)-4-tridecenyl acetate, based on chemical analyses, electroantennogram assays, and field trapping in California and Florida. Males were captured equally well in traps baited with (E)-4-tridecenyl acetate alone or a variety of (Z)- and (E)-4-tridecenyl acetate blends, although theZ isomer was not detected in extracts of female glands.Lepidoptera: Gelechiidae.     

Identification of sex pheromone component of spruce budmothZeiraphera canadensis

The analyses of virgin female sex pheromone gland extracts by gas chromatography (GC), GC-electroantennographic detection (GC-EAD) and GC-mass spectrometry (GC-MS) followed by field-trapping experiments, have identified (E)-9-tetradecenyl acetate (E9–14:Ac) as the primary sex pheromone component of the spruce budmoth,Zeiraphera canadensis. Dosages of 1.0–100.0 g ofE9–14:Ac impregnated in rubber septa provide effective trap baits.Lepidoptera: Tortricidae: Eucosminae.     

Female sex pheromone components of jasmine mothPalpita unionalis (Lepidoptera: Pyralidae)

(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.     

Analogs of sex pheromone of processionary moth,Thaumetopoea pityocampa: Synthesis and biological activity

The synthesis and biological activity of some analogs of (Z)-13-hexadecen-11-ynyl acetate1, the major component of the sex pheromone of the processionary mothThaumetopoea pityocampa is described. The analogs have been formally derived by structural modification of the enyne and acetate functions of the parent compound1. In field tests, trifluoroacetate ester16 and the analog,11, with fluorine substitution at the olefin site, decreased the pheromone action, whereas epoxy derivative,10, from epoxidation of the olefin moiety in1, and propionate ester15 gave synergistic activity. The formate14 had a variable effect according to the composition of the lure. Formal reduction of the enyne to give the acetylene2 was found to retain activity. Alcohols12 and13, resulting from hydrolysis of the enyne1 and acetylene2, respectively, inhibited the action of their parent compounds.Lepidoptera, Thaumetopoeidae.     

Chirality of 5,11-dimethylheptadecane,the major sex pheromone component of the hemlock looper,Lambdina fiscellaria (Lepidoptera: Geometridae)

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.     

Isolation,identification, and synthesis of a female sex pheromone of the navel orangeworm,Amyelois transitella (Lepidoptera: Pyralidae)

A sex pheromone of the navel orangeworm,Amyelois transitella (Walker), was obtained from ether rinses of the sex pheromone gland of calling females. The pheromone was isolated by means of liquid and gas chromatography and was identified as one of four possible geometrical isomers of 11,13-hexadecadienal by means of spectroscopic and microchemical methods. Synthesis and laboratory bioassay of all four isomers revealed that only the (Z,Z) isomer was biologically active. (Z,Z)-11,13-hexadecadienal elicited quantitatively similar activation and attraction responses byA. transitella males as did the natural product.Mention of a commercial or proprietary product in this paper does not constitute an endorsement of that product by the USDA. Accepted for publication February 28, 1979.     

Individual variation in sex pheromone of smaller tea tortrix moth,Adoxophyes sp. (Lepidoptera: Tortricidae)

Female smaller tea tortrix mothsAdoxophyes sp. (Lepidoptera: Tortricidae), which initiated calling at 1, 2, or 3 days old, respectively, were analyzed individually for (Z)-11-tetradecenyl acetate (Z11-14:OAc) and (Z)-9-tetradecenyl acetate (Z9–14: OAc) in the pheromone gland via GLC. Among different age groups, broad and similar distributions were found for pheromone quantity (¯X=58.6±52.9 ng/female; range 1.3–219.8 ng/female). The ratio of the two pheromone components averaged 6535 but ranged from 8416 to 4060. The significance of the pheromone blend variation to the attraction of males was tested in a field experiment. The ratio of males trapped by the most attractive blend versus the least attractive one was 2.2.     

Female sex pheromone of the pickleworm,Diaphania nitidalis (Lepidoptera: Pyralidae)

Heptane extracts of the ovipositors from pickleworm adults (Diaphania nitidalis) were found to contain (E)-11-hexadecenal along with proportionally smaller amounts of (Z)-11-hexadecenal, (E)- and (Z)-11-hexadecen-1-ol, hexadecanol, hexadecanal, and a trace amount of (E,Z)-10,12-hexadecadienal. Assays conducted in a flight tunnel and in the field showed that a synthetic mixture of the five unsaturated compounds elicited behavioral responses from pickleworm males that were indistinguishable from those elicited by extracts of the female or by mate-calling females. When any component was deleted from the set of five unsaturated compounds, the intensity and extent of male responses to the resulting mixtures were significantly attenuated. The female sex pheromone of the pickleworm resembles the pheromone of a congeneric species,D. hyalinata, but bioassays indicated that (E,E)-10,12-hexadecadienal, produced byD. hyalinata but not by the pickleworm, plays a role in pheromonal specificity.     

Effect of rearing temperature on pheromone component ratio in potato tuberworm moth,Phthorimaea operculella, (Lepidoptera: Gelechiidae)

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.     

Stegobiol,a new sex pheromone component of drugstore beetle (Stegobium paniceum L.)

New sex pheromone component of femaleStegobium paniceum L. was isolated and identified as 2,3-dihydro-2,3,5-trimethyI-6-(1-methyl-2-hydroxybutyl)-4H-pyran-4-one, stegobiol, by spectral data and chemical conversion from stegobinone. Relative configuration at C-2, C-3, and C-1 was determined as 2S,3R,1S by the conversion from (2S,3R,1R)-stegobinone. This new sex pheromone elicits the pheromonal response from the species.     

Identification of the sex pheromone of the yellow scale

The sex pheromone of the yellow scale,Aonidiella citrina (Coquillett), was isolated from airborne collections and found to be (E)-3,9-dimethyl-6-isopropyl-5,8-decadien-1-yl acetate. Aonidiella citrina (Coquillett) (Homoptera: Diaspididae).This research was supported by a USDA cooperative research grant.