Attraction of tortricid moths of subfamily olethreutinae to field traps baited with dodecadienes

All four geometrical isomers of 7,9- and 8,10-dodecadienes with acetate, alcohol, and aldehyde functional groups were synthesized and field tested. The field survey produced sex attractant lures for 14 insect species. Species in the generaCydia, Grapholita, Eucosma, Pelochrista, Petrova, Phenta, Hedya, and Pseudosciaphila were captured. Defined lures were developed for some of the species captured. Gas chromatographie retention times for all geometrical isomers of 7,9- and 8,10-dodecadienes with acetate, alcohol, and aldehyde functional groups are reported. A study of the isomerization of 8,10-dodecadienyl acetates and aldehydes impregnated in rubber septa is reported.     

Attraction of pea mothCydia nigricana F. (Lepidoptera: Tortricidae) to female sex pheromone (E,E)-8,10-dodecadien-1-YL acetate,is inhibited by geometric isomersE,Z, Z,E, andZ,Z

Field attraction ofCydia nigricana males to synthetic female sex pheromone (E,E)-8,10-dodecadien-1-yl acetate, formulated on red rubber septa, declined continuously during two weeks. This was due to isomerization of (E,E)-8,10-dodecadien-1-yl acetate: eight days after application of purifiedE,E isomer, the proportion ofE,Z;Z,E; andZ,Z isomers in rubber septa aged in the laboratory was 4%; a 5% addition of any one of these isomers to fresh lures of (E,E)-8,10-dodecadien-1-yl acetate significantly reduced male attraction. Stereospecific syntheses of (E,Z)-, (Z,E)-, and (Z,Z)-8,10-dodecadien-1-yl acetate are described. The pheromone gland ofCydia nigricana contains 0.8 ng/female of (E,E)-8,10-dodecadien-1-yl acetate, accompanied by three monounsaturated acetates, (E)-9-dodecen-1-yl acetate, (Z)-5-tetradecen-1-yl acetate, and (Z)-7-tetradecen-1-yl acetate (0.1 ng/female each). These compounds did not augment male trap catch when added to (E,E)-8,10-dodecadien-1-yl acetate.     

Components of the sex pheromone of the female spotted stalk borer,Chilo partellus (Swinhoe) (Lepidoptera: Pyralidae): Identification and preliminary field trials

FemaleChilo partellus (Swinhoe) abdominal tip extracts were examined by gas-liquid chromatography (GLC) combined with simultaneous electroantennographic (EAG) recording from the male moth. Two olfactory stimulants were detected and identified as (Z)-11-hexadecenal (I) and (Z)-11-hexadecen-1-ol (II) by their GLC behavior, microchemical reactions, and comparison with synthetic materials. Both compounds were detected in volatiles emitted by the calling female moth. Synthetic (Z)-9-tetradecenyl formate, a structural analog of aldehyde (I), also elicited a significant EAG response from the male moth. Field trials carried out in India using synthetic (I) and (II) as bait in water traps showed that compound (I) was highly attractive to maleC. partellus; compound (II) was not attractive, and its addition to (I) significantly reduced trap catches.     

Anemotactic response threshold of the Indian meal moth,Plodia interpunctella (Hübner) (Lepidoptera: Pyralidae), to its sex pheromone

The effect of different concentrations of the sex pheromone (Z,E)-9,12-tetradecadien-1-ol acetate on the upwind anemotactic behavior of the malePlodia interpunctella (Hübner) was measured at 23 ± 1 ° C and 34 ± 1 ° C. The stimulus-response regression lines were analyzed by a new procedure that accounts both for control responses in the absence of pheromone and also for peak responses below 100% in the presence of concentrations considerably above the normal physiological levels. From the regression line for each temperature, the upwind anemotactic thresholds were calculated to be 1.34 × 10⁶ molecules/cm³ at 23 ° C and 1.65 × 10⁴ molecules/cm³ at 34 ° C, similar to other thresholds reported in the literature. Since departures from the two lines occurred at the highest concentrations tested, near 10⁸ molecules/cm³, the upwind anemotactic behavior may change qualitatively above an altered-behavior threshold that is about two orders of magnitude higher than the upwind anemotactic threshold. The lower response at 23 ° C suggests that cool temperatures inhibit flight in response to pheromonal stimulation.Mention of a commercial or proprietary product in this paper does not constitute an endorsement of that product by the USDA.     

Variability in pheromone composition and periodicity of pheromone titer in potato tuberworm moth,Phthorimaea operculella (Lepidoptera: Gelechiidae)

The ratios and quantities of the pheromone components, (E,Z)-4,7-tridecadien-1-yl acetate (diene) and (E,Z,Z)-4,7.10-tridecatrien-1-yl acetate (triene), in the glands of individual female potato tuberworm moths (Phthorimaea operculella) originating from the United States (California) and Japan (Nagoya) were analyzed by gas chromatography. Quantities of glandextracted pheromone components of Nagoya females fluctuated in a periodic fashion during the photoperiod. Maximal titers coincided with the onset of scotophase (and calling), then gradually declined to minimal levels soon after lights-on. The average daily pheromone quantities decreased significantly as females aged. Both populations exhibited considerable variation in the ratio of the two components. The proportions of triene in the blend ranged from 27% to 88% (triene –X = 56 ± 13% SD; CV = 23%) for California females and from 16% to 71% (42 ± 13%; CV = 31%) for Nagoya females. Nagoya females also stored significantly higher amounts of pheromone in their glands (8.6 ± 3.9 ng) than did California females (2.7 ± 1.4). The differences between the populations, while substantial, would probably not be sufficient to impart a barrier to panmixis, given the wide range of component ratios favored by the males.     

Field trapping of threeEpinotia species with (Z,Z)-7,9-dodecadienyl acetate (Lepidoptera: Tortricidae)

Field survey of the geometrical isomers of 7,9-dodecadienyl alcohol, acetate, and aldehyde has resulted in attractants and inhibitors for three species of tortricid moths.Epinotia silvertoniensis and an undescribedEpinotia sp. were all attracted to (Z,Z)-7,9-dodecadienyl acetate. AnotherEpinotia sp. was attracted to (Z,Z)-7,9-dodecadienyl acetate and (Z,Z)-7,9-dodecadien-1-ol. Electroantennogram data and inhibition patterns for one of theEpinotia sp. are also reported. In addition,E. criddleana was attracted to lures containing (E)-9-dodecenyl acetate.     

Response of male eye-spotted bud moth,Spilonota ocellana (Lepidoptera: Tortricidae), to different pheromone blends in north America and The Netherlands

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.Agriculture Canada Summerland Research Station Contribution No. 821.     

Capture of gypsy moth,Lymantria dispar (L.), andLymantria mathura (L.) males in traps baited with disparlure enantiomers and olefin precursor in the People's Republic of China

Pheromone traps baited with (+)-disparlure,cis-7,8-epoxy-2methyocta-decane, captured males ofLymantria dispar, L. monacha, andL. mathura in northeastern People's Republic of China.L. dispar responded to the addition of olefin to (+)-disparlure-baited traps in a negative doseresponse manner. Observations on site and seasonal capture ofL. dispar andL. mathura are discussed.Lepidoptera: Lymantriidae.     

Synthesis of the two components of the sex pheromone system of the potato tuberworm moth,Phthorimaea operculella (Zeller) (Lepidoptera: Gelechiidae) and field experience with them

Male potato tuberworm moths are attracted by a mixture oftrans-4,cis-7-tridecadien-1-ol acetate andtrans-4,cis-7,cis-10-tridecatrien-1-ol acetate. The synthesis of both compounds is described. Overall yields were 14.4 and 9.5% after distillation. The products were purified by liquid chromatography. Mixtures of these compounds in several ratios and quantities were tested in potato fields in Australia, Peru, and Cyprus. The largest catches were obtained from water pan traps baited with rubber sleeve stoppers containing both components in ratios varying between 19 and 91. The stoppers were attractive over a period of several months even under hot weather conditions.     

Sex pheromone components of three species ofSemiothisa (Geometridae), (Z,Z,Z)-3,6,9-heptadecatriene and two monoepoxydiene analogs

Adult males ofSemiothisa signaria dispuncta (Walker) were attracted to field traps baited with (Z,Z,Z)-3,6,9-octadecatriene and (Z,Z)-6,9-cis-3,4-epoxy-octadecadiene. However, analyses of sex pheromone gland extracts of females of this species by GC-MS and by GC in combination with an electroantennograph detector (GC-EAD) showed the pheromone to be comprised of a mixture of the next lower homologs: (Z,Z,Z)-3,6,9-heptadecatriene and (Z,Z)-6,9-cis-3,4-epoxy-heptadecadiene. Blends of these two C₁₇ compounds were subsequently found to be more attractive to males in the field than the corresponding C₁₈ mixtures. Sex pheromones of two otherSemiothisa species were also found to contain C₁₇ components. (Z,Z,Z)-3,6,9-Heptadecatriene, detected by GC-EAD analysis of a female abdominal tip extract ofS. bicolorata (Fabricius), attracted conspecific males, and this attraction was significantly reduced by additions of (Z,Z)-6,9-cis-3,4-epoxyheptadecadiene, the major pheromone component ofS. signaria dispuncta, to the lure. (Z,Z)-3,9-cis-6,7-Epoxy-heptadecadiene was detected by GC-EAD analysis as the primary male antennal stimulatory component present in abdominal tip extracts ofS. ulsterata (Pearsall), and males of this species were attracted to traps baited with this epoxide. Each of these three C₁₇ compounds constitute previously unknown lepidopteran sex pheromone components. Blends of (Z,Z, Z)-3,6,9-heptadecatriene and (Z,Z)-3,9-cis-6,7-epoxyheptadecadiene attracted males of a fourth species,S. delectata Hulst, but no females of this species were obtained to permit analysis of its sex pheromone. The occurrence of (Z,Z,Z)-3,6,9-heptadecatriene inS. neptaria (Guenee) females was indicated by GC-MS analysis of an abdominal tip extract; however, no males were attracted to any of the fielded mixtures containing this hydrocarbon.     

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.