Components of the sex pheromone of the female sugar cane borer,Chilo sacchariphagus (Bojer) (Lepidoptera: Pyralidae)

The female sex pheromone of the sugar cane borer,Chilo sacchariphagus, has been shown to contain the two structurally related compounds, (Z)-13-octadecenyl acetate (I) and (Z)-13-octadecen-1-ol (II). These components were detected in female abdominal tip extracts by gas-liquid chromatography (GLC) combined with electroantennography (EAG), and were identified by their GLC behavior, microozonolysis, and interconversion, and by comparison of natural and synthetic material. Field tests in Mauritius showed that traps baited with components I and II combined in ratios from 11 to 91 caught maleC. sacchariphagus moths, and that the 71 ratio was comparable in performance with a virgin female moth. Neither component presented separately in traps caught significant numbers of moths.     

Identification and field testing of additional components of female sex pheromone of African armyworm,Spodoptera exempta (Lepidoptera: Noctuidae)

Ovipositor washings from virgin femaleSpodoptera exempta (Walker) (Lepidoptera: Noctuidae) were analyzed by high-resolution gas chromatography (GC) linked to a male electroantennogram (EAG). GC retention times of the two major EAG responses observed were consistent with their assignment as (Z)-9-tetradecenyl acetate and (Z,E)-9,12-tetradecadienyl acetate, as previously identified. However, three other EAG responses were also noted that had GC retention times consistent with (Z)-9-tetradecenal, (Z)-9-tetradecen-1-o 1, and (Z)-11-hexadecenyl acetate. The components were present in the ratio of 10051.53.54, respectively. Further analysis of the ovipositor washings by GC linked to a mass spectrometer (GC-MS) confirmed these findings and indicated the presence of a sixth component consistent with (Z)-11-tetradecenyl acetate present at 2 % of the major component. In field tests carried out in Kenya, (Z)-11-hexadecenyl acetate was the only newly identified component to enhance the catch of the original two-component mixture when presented in their natural ratio. The addition of (Z)-9-tetradecen-1-ol reduced catch, while (Z)-9-tetradecenal and (Z)-11-tetradecenyl acetate had no apparent effect.     

Identification of sex pheromones of two sibling species in dingy cutworm complex,Feltia jaculifera (GN.) (Lepidoptera: Noctuidae)

The sex pheromone components of the two sibling species of the dingy cutworm that occur on the prairies of western Canada were identified in abdomen-tip extracts from calling female moths. Three monounsaturated acetates, (Z)-7-dodecenyl acetate, (Z)-9-tetradecenyl acetate, and (Z)-11-hexadecenyl acetate, are common to both species in ratios of 100133 for species A and 0.30.5100 for species B. The most effective synthetic blends for the attraction of male moths in the field consisted of these three components in ratios of 1010 at 8.8g/lure for species A and 112000 at 500g/lure for species B. The addition of Z5-12Ac to either blend reduced the catches and the addition of Z7-12OH orZ11-16OH to the three-component blend reduced the catches of species B males. The species are morphologically indistinguishable, but the identity of the males attracted to the synthetic blends could be confirmed by their antennal responses to a test blend of the three components using a GC-EAD system. Both synthetic attractant blends are competitive with females and will be useful for studying the distribution, biology, and relative abundances of the two species.Contribution no. 3879005 of the Lethbridge Research Station.     

Evaluation of the synthetic major component of the sex pheromone of Tuta absoluta (Meyrick) (Lepidoptera: Gelechiidae)

In wind-tunnel bioassays, dispensers loaded with 1 g of the synthetic major component (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate (TDTA) of the sex pheromone emitted by Tuta absoluta (Meyrick) females were found to be highly attractive to conspecific males. Field experiments were conducted to evaluate the efficacy of five trap designs. The best trap, baited with 100 g of the synthetic sex pheromone caught on average 1200 males per trap per night, while those baited with virgin females caught only 201 males. The male response to this pheromone is restricted to the same early-morning time window during which females exhibit calling behavior. The high biological activity of the synthetic pheromone suggests that it could be useful for pest monitoring and in mating disruption.     

Heliothis virescens: Attraction of males to blends of (Z)-9-tetradecen-1-ol formate and (Z)-9-tetradecenal

In field trapping experiments, 161 and 321 blends of (Z)-9-tetradecen-1-ol formate (Z-9-TDF) and (Z)-9-tetradecenal (Z-9-TDAL) caught as manyHeliothis virescens (F.) as 3 virgin females and virelure, the synthetic pheromone of this species [a 161 mixture of (Z)-11-hexadecenal (Z-11-HDAL) and (Z)-9-tetradecenal]. Z-9-TDF and (Z)-7-dodecen-1-ol formate (Z-7-DDF) are structurally similar to Z-11-HDAL and Z-9-TDAL, respectively. The sensory input elicited by Z-9-TDF appears to substitute for the sensory input of Z-1 1-HDAL. In contrast, Z-7-DDF had no significant effect on catches of maleH. virescens when used alone, in combination with either Z-11-HDAL or Z-9-TDF as a bait in traps, or as a disruptant of pheromone communication via permeation of the atmosphere. Furthermore, Z-9-TDF may be a more stable and economical attractant forH, virescens males than is Z-1 1-HDAL.This paper reports the results of research only. Mention of a pesticide in this paper does not constitute a recommendation for use by the U.S. Department of Agriculture nor does it imply registration under FIFRA as amended. Also, mention of a commercial or proprietary product in this paper does not constitute a recommendation or an endorsement of that product by the USDA.     

Identification of sex pheromone of browntail moth,Euproctis chrysorrhoea (L.) (Lepidoptera: Lymantriidae)

A unique sex attractant pheromone was isolated and identified from extracts of ovipositor tips from the female browntail moth (Lepidoptera: Lymantriidae). The pheromone compound, (Z,Z,Z,Z)-7,13,16,19-docosatetraen-1-ol isobutyrate, CH₃CH₂CH=CHCH₂CH=CHCH₂CH= CH(CH₂)₄CH=CH(CH₂)₆O₂CCH(CH₃)₂, was identified by a combination of gas chromatography, mass spectrometry, and microreactions and was confirmed by synthesis. Traps baited with 5–50 g of the synthetic pheromone, dispensed from rubber septa treated with an antioxidant and a UV stabilizer, gave male moth captures that were comparable to traps baited with three virgin females. Higher (250 g) and lower (0.04–2.5 g quantities of the synthetic pheromone on septa captured somewhat fewer males. Captures were the same for similar quantities of the natural and synthetic pheromone. Minor, inactive components in the tip extract were identified as a mixture of 7- and 8-pentacosanone.     

Components of female sex pheromone of spotted bollworm,Earias vittella F. (Lepidoptera: Noctuidae): Identification and field evaluation in Pakistan

Ovipositor washings from virgin femaleEarias vittella (F.) (Lepidoptera: Noctuidae) moths were examined by gas chromatography (GC) linked to electroantennography (EAG). Six components were detected by the male moth. These were identified by comparison of their retention times with those of a range of synthetic standards on fused silica capillary GC columns as hexadecanal, (Z)-11-hexadecenal, (E,E)-10,12-hexadecadienal, octadecanal, (Z)-11-octadecenal, and (E,E)-10,12-hexadecadien-1-ol in 1210241 ratio. Field testing in Pakistan showed that a 2102 mixture of (Z)-11-hexadecenal, (E,E)-10,12-hexadecadienal, and (Z)-11-octadecenal was as attractive to maleE. vittella moths as the six-component mixture and equal in attractiveness to a virgin female moth. Omitting (Z)-11-hexadecenal or (Z)-11-octadecenal greatly reduced this attractiveness. It was found that synthetic lures must be protected from sunlight to prevent loss of attractiveness caused by isomerization of the conjugated diene aldehyde, and addition of (E,Z)-10,12-hexadecadienal, one of the products of isomerization, was shown to reduce attractiveness significantly. During this work, a 101 mixture of (E,E)-10, 12-hexadecadienal and (Z)-11-hexadecenal was shown to be as attractive toE. insulana (Boisd.) male moths as a virgin female moth, and the attractiveness of this mixture was further increased by addition of (E,Z)-10,12-hexadecadienal.     

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.     

Sex pheromone specificity as a reproductive isolating mechanism among the sibling speciesArchips argyrospilus andA. mortuanus and other sympatric tortricine moths (Lepidoptera: Tortricidae)

MaleArchips argyrospilus (Walker) were maximally attracted to a 60404200 admixture of (Z)-11-tetradecenyl, (E)-11-tetradecenyl, (Z)-9-tetradecenyl and dodecyl acetates. The identification of (Z)-9-tetradecenyl acetate, in addition to the other 3 components reported previously, is the first report of a 4-component pheromone system in moths.Archips mortuanus Kearfoot, a sibling species, was maximally attracted to a blend of the same components, but in a 90101 mix of the tetradecenyl acetates. Among a number of tortricine moths that co-occur on apples and other hosts in New York, British Columbia, and elsewhere, differences in diel rhythms of attraction and seasonal distribution are insufficient to maintain reproductive isolation. Although the attractant systems of these species often possess components in common, males are maximally attracted to a speciesspecific blend. In tortricine moths attraction specificity appears to be a paramount mechanism for species partitioning.     

Female sex pheromone of oriental tobacco budworm,Helicoverpa assulta (Guenee) (Lepidoptera: Noctuidae): Identification and field testing

Analysis of ovipositor washings from virgin femaleHelicoverpa assulta (Guenée) (Lepidoptere: Noctuidae) from Korea by gas chromatography (GC) linked to electroantennography and GC linked to mass spectrometry resulted in the identification of nine compounds, hexadecanal, (Z)-9-hexadecenal, (Z)-11-hexadecenal, hexadecyl acetate, (Z)-9-hexadecenyl acetate, (Z)-11-hexadecenyl acetate, hexadecan-l-ol, (Z)-9-hexadecen-l-ol, and (Z)-11-hexadecen-1-ol. However, ovipositor washings from females from Thailand contained mainly the 16-carbon aldehydes with very small amounts of (Z)-9-hexadecenyl acetate. Field tests conducted in Korea, China, and Thailand indicated that a binary blend of (Z)-9-hexadecenal and (Z)-11-hexadecenal was sufficient for attraction, although the most attractive ratio of compounds varied with location. In Korea a 201 blend of compounds was the most attractive, while in Thailand a 7.51 blend was most attractive. In China both blends of hexadecenal isomers were equally attractive. Addition of the hexadecenyl acetates to the 201 blend of hexadecenals in the ratio of 13.3 increased the trap catch of maleH. assulta compared to lures containing the aldehydes alone in Korea but reduced trap catch in China. Addition of the hexadecenyl acetates to the 7.51 blend of hexadecenals had no significant effect on trap catch in Thailand or China compared to the aldehydes alone. The addition of the 16-carbon alcohols to the aldehydes had a significantly inhibitory effect in all three countries, suggesting they are not pheromone components. Taken together these results indicate thatH. assulta is polymorphic with at least two populations responding to different sex pheromones.     

Sugar beet crown borer,Hulstia undulatella (Clemens) 1: Identification and field tests of female sex pheromone gland components

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 100421, 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 g Z9-14:Ac+16 g Z9-14:OH+42 g Z11-16:Ac is suggested for use in monitoring traps.Lepidoptera: Pyralidae: Phycitinae.     

Electroantennogram response of alfalfa seed chalcid,Bruchophagus roddi (Hymenoptera: Eurytomidae) to host- and nonhost-plant volatiles

The alfalfa seed chalcid (ASC),Bruchophagus roddi, is a monophagous pest of alfalfa that parasitizes developing seeds. To further understand the olfactory basis of host-plant recognition by ASCs, we recorded electroantennograms (EAGs) from females and males to 39 volatiles from both alfalfa and red clover. The chemoreceptive sensitivity of ASCs was selective for certain general classes of compounds, defined by their carbon-chain length (C₆ and C₈), structure (aliphatics and phenolics), isomerism, and/or functional group (acetates, ketones, and alcohols). The compounds that elicited the largest EAGs were ranked as follows: (Z)-3-hexenyl acetate > hexyl acetate acetophenone octan-3-one methyl salicylate > octan-3-ol > oct-1-en-3-one > oct-1-en-3-ol (E)--ocimene (Z)- and (E)-3-hexen-1-ols. Over half the test compounds elicited significantly different responses between the sexes, and female antennal responses exceeded those of males for twice the number of these volatiles. Relationships of the tested volatiles to host-plant composition, EAG responses, and ASC behaviors showed no consistent correlations. However, nearly all of the host-plant volatiles known to stimulate behavioral activity also elicited moderate to potent EAG responses.     

Attraction of redbanded leafroller moths,Argyrotaenia velutinana,to blends of (Z)-and (E)-11-tridecenyl acetates

The pheromone ofArgyrotaenia velutinana (Walker) is a 928150 mixture of (Z)-11-, (E)-11-tetradecenyl and dodecyl acetates. An 8515 blend of (Z)-11- and (E)-11-tridecenyl acetates produces a trap catch equivalent to that with the pheromone blend. The sensory input elicited by (Z)-11-tridecenyl acetate appears to substitute for the sensory input of both (Z)-11-tetradecenyl and dodecyl acetates, whereas the input from (E)-11-tridecenyl acetate appears to substitute for that of (E)-11-tetradecenyl acetate. Surprisingly, addition of dodecyl acetate to the tridecenyl acetates mixture decreases trap catches.Lepidoptera: Tortricidae.     

Calling behavior and pheromone titer in the smaller tea tortrix moth,Adoxophyes sp. (Lepidoptera: Tortricidae)

The calling behavior and pheromone titer in the female smaller tea tortrix moth,Adoxophyes sp., were investigated under a 1410-hr light-dark photoperiod. Quantitative gas chromatographic analysis of ovipositor extract for (Z)-11-tetradecenyl acetate (Z11–14Ac) and (Z)-9-tetradecenyl acetate (Z9–14Ac), the major pheromone components of this species, obtained on the third day postemergence, indicated that extractable amounts of sex pheromone were present throughout the period of observation. Maximal pheromone titer and calling activity was reached at 8 and 10 hr after onset of scotophase, respectively. The ratio ofZ11–14Ac toZ9–14Ac through the 24-hr period varied significantly. The significance of the sex pheromone component ratio variation on 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 2.16.     

Sex pheromone evidence for two distinct taxa withinGraphania mutans (Walker)

The sex pheromones of two populations ofGraphania mutans (Walker) were analyzed. Females from an Auckland population produced (Z)-9-tetradecenol (Z9-14OH), (Z)-9-tetradecenyl acetate (Z9-14OAc), (Z)-7-tetradecenol (Z7-14OH) and (Z)-7-tetradecenyl acetate (Z7-14OAc), while females from a Lincoln population produced these four compounds and a large amount of (Z)-9-tetradecenal (Z9-14Ald). Significant differences, paralleling the difference between females, were observed when the responses of males of both populations to the above and other related compounds were tested by electroantennogram, field-trapping, and wind-tunnel bioassays. The most distinct difference was observed in the wind tunnel. Males from both taxa flew upwind and touched pheromone sources containing sex pheromone extract of females of their own taxon, but either did not initiate upwind flight or arrested upwind flight shortly after taking flight in response to extract from females of the other taxon. The difference between the pheromone systems of the two populations is probably due to the presence and importance of Z9-14Ald in the pheromone blend of the Lincoln population. Thus the addition of a relatively large amount of Z9-14Aid to a four-component pheromone blend (i.e., Z9-14OH, Z9-14OAc, Z7-14OH, andZ7-14OAc) attractive to Auckland males completely suppressed trap catches of male G.Mutans in Auckland but large numbers of males were caught at both Lincoln and Nelson in traps baited with this five-component blend. In wind-tunnel studies, the addition of even small (1% of amount of Z9-14OH) amounts ofZ9-14Ald to the four-component blend resulted in a significantly greater proportion of Auckland males arresting upwind flight than to the four-com ponent blend. It is suggested that these two populations of G. nations represent distinct sibling species within the described concept.LepidopteraNoctuidaeHadeninae.     

Sex pheromone ofAdoxophyes orana: Additional components and variability in ratio of (Z)-9- and (Z)-11-tetradecenyl acetate

Twelve products related to the sex pheromone main components (Z)-9- and (Z)-11-tetradecenyl acetate (Z9–14Ac andZ11–14Ac, respectively), were identified in female pheromone gland extracts of the laboratory-reared summerfruit tortrix moth,Adoxophyes orana F.v R. These are the geometric isomers and the alcohols of the main components, (Z)-9-dodecenyl acetate, (Z)-11-hexadecenyl acetate, and saturated acetates of 12–22 carbons. The ratio ofZ9–14Ac toZ11–14Ac in individuals varied from 3.51 to 111 with an average of 6.2; their total added up to 462 ng/female with an average of 182 ng for 2- to 7-day-old individuals. No qualitative or quantitative differences were observed between laboratory and field insects.Z9–14Ac,Z11–14Ac and the corresponding alcohols were also found in female effluvia. Addition of either of the two alcohols to a blend of the two acetates augmented trap catch in the field. The same was true for (Z)-9,(E)-12-tetradecadienyl acetate which was not detected in gland extracts.     

Identification and field testing of female-produced sex pheromone components of the spring cankerworm,Paleacrita vernata Peck (Lepidoptera: Geometridae)

Two sex pheromone components, 3(Z),6(Z),9(Z)-nonadecatriene (3Z,6Z,9Z-19 H), and 3(Z),6(Z),9(Z)-eicosatriene (3Z,6Z,9Z-20 H), have been positively identified, and a third component, 6(Z),9(Z)-nonadecadiene (6(Z),9(Z)-19 H) has been tentatively identified from abdominal tip extracts of female spring cankerworm moths,Paleacrita vernata Peck (Lepidoptera Geometridae). The pheromone components were identified by a combination of gas chromatography, electroantennography, mass spectrometry, chemical tests, comparison with standards, and field testing. Only 3Z,6Z,9Z-20 H exhibited significant attractant activity when tested alone, and it was potentiated by the other two components. The attractive blend was an 821 ratio of 3Z,6Z,9Z-20H/3Z,6Z,9Z-19H/6Z,9Z-19H. However, the two-component blend of 3Z,6Z,9Z-20 H and 6Z,9Z-19 H (81 ratio) was as attractive as the three-component blend in further field tests. A series of related compounds, the diene monoepoxides available from epoxidation of C₁₉ and C₂₀ 3Z,6Z,9Z-trienes, some of which have been found in the pheromone blends of other moth species, were tested as behavioral antagonists. The attraction of male moths to synthetic lures was suppressed by the addition of 6Z,9Z-cis-3,4-epoxy-nonadecadiene to the lures. Additional experiments were performed to determine the effects of lure dosage, trap height, and trap design on the numbers of male moths captured.Issued as NRCC 30711.     

Sex pheromone of the saltmarsh caterpillar moth,Estigmene acrea

Three compounds have been identified as components of the sex pheromone emitted by females of the saltmarsh caterpillar moth,Estigmene acrea (Drury). These are (Z,Z)-9,12-octadecadienal (I), (Z,Z,Z)-9,12,15-octadecatrienal (II), and (Z,Z)-3,6-cis-9,10-epoxyheneicosadiene (III). In female tip extract they were found in a ratio of 1625, respectively, and in trapped female effluvia the ratio was 1627, respectively. Combinations of III with either I or II elicited sustained upwind flight in a wind tunnel, but none of these compounds by themselves did so. There is evidence that the antennal acceptor site for III is chiral.Lepidoptera: Arctiidae.Supported in part by the Rockefeller Foundation and by National Science Foundation Grants GB-38020 and PCM 78-13241.     

Behavioral and electrophysiological activity of (Z,E)-7,9,11-dodecatrienyl formate,a mimic of the major sex pheromone component of carob moth,Ectomyelois ceratoniae

The behavioral and electrophysiological activity of a mimic [(Z,E)7,9,11-dodecatrienyl formate] of the major sex pheromone component [(Z,E) 9,11,13-tetradecatrienal] of carob moth was assessed. Wind-tunnel bioassays demonstrated that the formate was as effective as natural gland extracts, and significantly more effective than the trienal alone or than the trienal blended with two minor pheromone components, in evoking source contact. Dispensers containing the formate were as effective as trienal-containing blend lures in attracting males when placed at the same dosage in traps in date gardens. Single-cell recordings showed that at least two olfactory neurons, differentiated by spike amplitude, are located in the long trichoid hairs on male carob moth antennae. Dose-response relationships indicated that puffs from cartridges loaded with at least 0.1 g of the formate or of the trienal were necessary to elicit spiking by either the small or the large-spiking cell within a sensillum. Cross-adaptation studies demonstrated that both compounds stimulated the same large-spiking cell. The frequencies of spikes evoked from the large cell when stimulated by emissions from 0.1-g, 1-g, or 10-g cartridges of either the formate or the trienal were not significantly different, suggesting that the formate is an effective mimic of the trienal at the antennal receptor cell level.     

Sex pheromone of female african white rice stem borer,Maliarpha separatella (Lepidoptera: Pyralidae) from Sierra Leone: Identification and field testing

Analysis of ovipositor washings of femaleMaliarpha separatella from Sierra Leone by high-resolution gas chromatography (GC) linked to a male electroantennograph (EAG) indicated the presence of three electrophysiologically active compounds. The GC retention times of these compounds were consistent with those of (Z)-9-tetradecen-1-ol, (Z,E)-9,12-tetradecadien-1-ol, and (E,E)-10,12-tetradecadien-1-ol. Analysis by El and CI mass spectrometry of ovipositor washings confirmed these identifications and also indicated the presence of the saturated analog, tetradecan-1-ol. There was no evidence, from these analyses, of the corresponding aldehydes or acetates. The EAG-active compounds were present in the ovipositor washings in a ratio of approximately 23.51, with the major component constituting approximately 0.4 ng per ovipositor. GC-MS analysis of entrained female effluvia confirmed that the EAG-active compounds were released by virgin females. Field testing of the EAG-active compounds indicated that (Z,E)-9,12-tetradecadien-1-ol and (E,E)10,12-tetradecadien-1-ol were attractive to male moths in ratios of between 9:1 and 39:1, while (Z)-9-tetradecen-1-ol was found to reduce trap catch when added to blends of the other two compounds.