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 components of female smaller tea tortrix moth,Adoxophyes sp. (Lepidoptera: Tortricidae) in Taiwan

(Z)-11-Teiradecenyl acetate (Z11-14: Ac) and (Z)-9-tetrade-cenyl acetate (Z9–14: Ac) were isolated as major sex pheromone components from the female tips of the smaller tea tortrix moth,Adoxophyes sp., in Taiwan. The average amount ofZ11- andZ9–14: Ac in each female gland was 24.9 and 14.1 ng, in a ratio of 6436, respectively. When compared to a closely related Japanese strain, which used theZ9-14: Ac,Z11-14 Ac,E11–14:Ac, 10-Me-12:Ac four-component system (in a ratio of 633142), the Taiwan formulation of two components caught significantly more Taiwan males than the Japanese formulation of four components.     

Synthesis of (±)-10-methyl-1-dodecanol acetate,the chiral component of the smaller tea tortrix moth (Adoxophyes sp.), with an option for asymmetric induction

A new route to (±)-10-methyl-1-dodecanol acetate, a minor component of the smaller tea tortrix moth (Adoxophyes sp.), is described. An optional sequence that permits the generation of the chiral center with enantiomeric excesses (ee's) as high as 74% (R) or 80% (S) employing the available (S)-(–)-prolinol as a chiral auxiliary may be included. High-performance liquid chromatography of diastereomeric intermediates allows preparation of products with greater ee's.     

Sex pheromone components of the blueberry leaftier mothCroesia curvalana kearfott (Lepidoptera: Tortricidae)

The GC-MS and GC-EAD analyses of sex-gland components and sex-gland-released volatiles have identified (E)- and (Z)-11-tetradecenal (9010) and (E)- and (Z)-11-tetradecenyl acetate (8515) as components of the sex pheromone chemical communication system ofCroesia curvalana (Kearfott). The aldehyde-to-acetate ratio of 91 was found in the gland-released components. This blend at a 0.1–1 g/day release rate from PVC lures was shown to be as effective as virgin females in the trapping of maleC. curvalana.     

Individual variation in the pheromone of the turnip moth,Agrotis segetum

Female turnip moths (Agrotis segetum) from a laboratory culture inbred for more than 30 generations, and the offspring (first and third generation) from field-collected insects were analyzed individually for acetates and alcohols in the pheromone gland. Quantitative analysis of individual components was performed at the subnanogram level by gas chromatographymass spectrometry (selected ion monitoring). The titer of the pheromone, i.e., the sum of the homologous acetates (Z)-5-decenyl acetate, (Z)-7-dodecenyl acetate, and (Z)-9-tetradecenyl acetate was 2.0 ± 0.3 ng in the laboratory culture and 3.2 ± 0.6 ng in the wild strain. There was no correlation between pheromone titer and female weight. The relative proportion of the pheromone components varied substantially between individuals, but there was no statistically significant difference between the two populations. The percentages of the respective compounds (¯X ± coefficient of variation) were 14.8 ± 127% for Z5-10:OAc, 55.6 ± 32% for Z7-12:OAc, and 29.6 ± 59% forZ9-14:OAc. The pheromone composition varied more in the wild strain than in the laboratory culture. The significance of the pheromone 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.Schiff., Lepidoptera: Noctuidae.This study was made within the Swedish project Odour Signals for Control of Pest Insects.     

Interpopulational variation in emitted pheromone blend of cabbage looper moth,Trichoplusia ni

Female cabbage looper moths,Trichoplusia ni, from laboratory colonies initiated from three locations across the United States emitted similar quantities and blend ratios of the six known pheromone components. In contrast, females from a long-established laboratory colony emitted a greater proportion of four of the five minor components relative to the major component, (Z)-7-dodecenyl acetate; only the relative proportion of 11-dodecenyl acetate was similar in all of the populations sampled. Females from this population emitted (Z)-7-dodecenyl acetate at a rate similar to that from females from field-collected colonies. Within each population there were highly significant correlations among the quantities of pheromone components of similar molecular weights. Correlations between components of different molecular weights were not as great, but often were significant. Similarities of blend ratios among field populations may indicate that the chemical signal in this species is conservative. The difference of the blend ratios in our laboratory population from the other populations may indicate a decrease in the intensity of selection pressure that usually would maintain these values.     

Sex pheromone of blackheaded fireworm,Rhopobota naevana (Lepidoptera: Tortricidae), a pest of cranberry

Splitless capillary gas chromatography indicated the presence of (Z)- and (E)-11-tetradecenyl acetate and (Z)-11-tetradecenyl alcohol in the washes of female abdominal tips of the blackheaded fireworm,Rhopobota naevana (Hubner). Gas chromatography combined with mass spectroscopy confirmed the presence of tetradecenyl acetate in extracts of female tips. The low levels observed in these extracts (< 1 ng/female equivalent), prevented further chemical and spectroscopic identification. These materials were found to be stimulatory at low levels in electroantennogram studies. A combination of 9 g of (Z)-11-tetradecenyl acetate and 3 g of (Z)-11-tetradecenyl alcohol on rubber septa in wing traps provided an effective attractant. (Z)-9-Dodecenyl acetate, a previously reported attractant, did not significantly increase field trapping catches when added to the binary mixture, but was found to enhance trap catches when added to each of the primary components.     

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.     

Sex pheromone ofPandemis heparana (Den. and Schiff.) (Lepidoptera:Tortricidae)

90% (Z)-11-tetradecen-1-yl acetate, 5% (Z)-9-tetradecen-1-yl acetate, 5% (Z)-11-tetradecen-1-ol, dodecyl acetate (<1%), and tetradecyl acetate (<1%) were identified from gland extracts ofPandemis heparana females by gas chromatography and gas chromatography-mass spectrometry analysis (including mass fragmentography studies), chemical characterization, total synthesis, laboratory and field bioassays. In the field, a mixture of (Z)-11-tetradecen-l-yl acetate and (Z)-9-tetradecen-l-yl acetate (955) was found to be essential for attractiveness ofP. heparana males.     

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 a four-component sex pheromone of the female oriental fruit moth,Grapholitha molesta (Lepidoptera: Tortricidae)

The female-emitted pheromone ofGrapholitha molesta (Busck), the Oriental fruit moth, was collected by holding females in glass flasks during calling. Flask washes were found to contain four pheromone components: (Z)-8-dodecenyl acetate and (E)-8-dodecenyl acetate in a 1007 ratio, and (Z)-8-dodecen-1-ol and dodecanol in a 10020 ratio. The ratio of (Z)-8-acetate to (Z)-8-dodecen-1-ol was approx. 10030. Approximately 0.1–0.2 ng of pheromone was recovered per female per hour of calling.Published as Journal Article No. 8598 of the Michigan State University Agricultural Experiment Station.     

Sex pheromone of the chokecherry leafroller moth,Sparganothis directana

(E)-9,11-Dodecadienyl acetate and (Z)-9,11-dodecadienyl acetate in conjunction with (E)-11-tetradecenyl acetate and (Z)-11-tetradecenyl acetate were found to comprise the sex pheromone ofSparganothis directana, based on chemical analysis, electroantennogram tests, and field trapping. (E)-9-Dodecenyl acetate and (Z)-9-dodecenyl acetate were also found in gland extracts but did not influence trap catches. The relative amounts of these compounds in the gland were 3521928 106, in the order named. Only (E)-9,1 1-dodecadienyl acetate, (E)-11-tetradecenyl acetate, and (Z)-11-tetradecenyl acetate were required for attraction of males to traps, dispensed in the relative amounts 501238, respectively.Lepidoptera: Tortricidae.Supported by National Science Foundation grant PCM 78-13241.     

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.     

Effect of temperature on biosynthesis of sex pheromone components in potato tuberworm moth,Phthorimaea operculella (Lepidoptera: Gelechiidae)

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.     

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.     

Intrapopulational changes in sex pheromone composition during scotophase in oriental tobacco budworm,Helicoverpa assulta (Guenée) (Lepidoptera: Noctuidae)

Solvent extracts of individual pheromone glands were prepared from femaleHelicoverpa assulta (Guenée) at 2-hr intervals throughout the scotophase. The amounts of female sex pheromone components, (Z)-9-hexadecenal, (Z)-11-hexadecenal, (Z)-9-hexadecenyl acetate, and (Z)-11-hexadecenyl acetate, in the extracts were determined by gas chromatographic analysis. Although females called from early scotophase (2 hr) until late scotophase (6 hr) the quantity of extracted pheromone remained high at 8 hr, the end of the scotophase. More than 70% of the pheromone gland extracts contained sex pheromone components regardless of whether the donor females had been called or resting. Pheromone components were absent from gland extracts prepared at the onset of the scotophase. The quantity of (Z)-9-hexadecenal and (Z)-11-hexadecenal increased rapidly to reach a maximum of approximately 260 and 30 ng/female, respectively, that was maintained for up to 8 hr, the duration of the scotophase. The quantity of (Z)-9-hexadecenyl acetate and (Z)-11-hexadecenyl acetate increased continuously during the scotophase to peak at 600 and 30 ng/female, respectively, 8 hr into the scotophase. At the end of scotophase the quantity of all pheromone components decreased significantly.     

Sex pheromone of the woodbine leafroller moth,Sparganothis sp.

The sex pheromone of the woodbine leafroller,Sparganothis sp., includes (E)-11-tetradecen-1-ol, (Z)-11-tetradecen-1-ol, and (E)-11-tetradecen-1-yl acetate, based on chemical analysis of gland extracts, electroantennogram tests, and field trapping. Highest trap catches were obtained when these compounds were dispensed in the relative proportions observed in the female gland. (Z)-11-Tetradecen-1-yl acetate also was found in gland extracts, but significantly reduced trap catches. The saturated compounds tetradecan-1-ol and tetradecan-1-yl acetate were found in gland extracts as well, but were not tested. The amounts of these compounds per female gland were 127, 93, 17, 20, 25, and 3 ng, in the order named.Lepidoptera: Tortricidae.Supported by National Science Foundation Grant PCM 78-13241.     

Sex pheromone components of the fruit-tree leaf roller,Archips argyrospilus (Walker) (Lepidoptera: Tortricidae), in British Columbia

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 1006421 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.     

Attraction of male turnip mothsAgrotis segetum (Lepidoptera: Noctuidae) to sex pheromone components and their mixtures at 11 sites in Europe,Asia, and Africa

Selected combinations of (Z)-5-decenyl, (Z)-7-dodecenyl, and (Z)-9-tetradecenyl acetates, the pheromone components of the turnip mothAgrotis Segetum were tested for field attractancy at six, two, and three sites in Europe, Asia, and Africa, respectively. At all of the sites in Eurasia and in northern Africa the ternary mixture of the acetates captured most males, while at the sites south of the Sahara in Africa, (Z)-5-decenyl acetate alone was responsible for attraction. Differences in male attraction among the populations studied confirm the existence of significant population variation in the pheromone ofA. segetum. Interpretation of the present results together with earlier studies suggests that this variation is more or less continuous in Eurasia and north Africa, while a clearly distinct pheromone type is present in the areas south of the Sahara desert.     

Sex pheromone of the tea tortrix moth (Homona coffearia Neitner)

Three compounds were isolated from female abdominal tips of the tea tortrix,Homona coffearia Neitner (Lepidoptera: Tortricidae) and identified as 1-dodecanol, 1-dodecyl acetate, and (E)-9-dodecen-1-yl acetate by chemical tests and mass spectrometry. These were the only appreciably active compounds detected in female gland extracts by male electroantennography of gas chromatographic collections. Synthetic (E)-9-dodecenyl acetate was shown to be active in attracting male moths in the field, and this activity was greatly increased by addition of dodecyl acetate and dodecanol. A very active lure for monitoring consists of 1 mg (E)-9-dodecenyl acetate, 3 mg dodecanol, and 1 mg dodecyl acetate in a polyethylene cap.Lepidoptera: Tortricidae