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.     

Behavioral responses of male turnip moths,Agrotis segetum,to sex pheromone in a flight tunnel and in the field

The response of individual male turnip mothsAgrotis segetum was observed in a sustained flight tunnel to a mixture of decyl acetate, (Z)-5-decenyl acetate, (Z)-7-dodecenyl acetate, and (Z)-9-tetradecenyl acetate in proportions similar to those found in gland extracts from virgin females (0.6: 1:5:2.5). Lures containing 3–30 g (Z)-5-decenyl acetate proved to be maximally attractive, with approximately 60% of the males completing all behavioral steps from activation to copulation efforts. A 300-g dosage caused significant arrestment of upwind flight. Peak response to synthetics, however, was significantly lower than to female glands. Omitting decyl acetate from the blend did not affect the activity, while omission of any of the three monounsaturated acetates caused a dramatic decrease in response. In the field maximum trap catches were achieved with 1- to 30-g lures. The subtractive assay carried out in the field confirmed the neutrality of decyl acetate and the importance of the three monoenes. Adding 1% of (Z)-8-dodecenyl acetate (earlier reported as an inhibitor) to the four-component mixture decreased the trap catch to about 50%, and increasing the amount of (Z)-8-dodecenyl acetate to 27% decreased the activity further to about 10%. (Z)-8-Dodecenyl acetate also decreased the number of successful flights in the flight tunnel.Schiff., Lepidoptera: Noctuidae.This study was made within the Swedish project Odour Signals for Control of Pest Insects.     

Defense Secretion of Prorhinotermes simplex: Toxicity to Insecticide Susceptible and Resistant House Fly

(E)-1-Nitropentadec-1-ene (NPE), the main component of the defense secretion of Prorhinotermes simplex soldiers, is toxic to both insecticide-susceptible (S) as well as to insecticide-resistant (R) strains of the house fly, Musca domestica. The LD₅₀ is 11.7 g/female fly for the S strain and 9.7 g for the R strain. The same efficacy of NPE on R and S strains indicates a different mechanism of action compared to conventional chlorinated, organophosphorus, and pyrethroid insecticides. Termite nestmates are protected against NPE by a specific detoxification mechanism. 1-Nitropentadecane, the detoxification product of NPE is nearly nontoxic to house flies, and doses up to 160 g/fly caused only very low mortality.     

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.     

Identification of sex pheromone components of darksided cutworm,Euxoa messoria,and modification of sex attractant blend for adult males

Eleven pheromone-like compounds were identified in excised abdomen tip extracts of calling adult females of darksided cutworm,Euxoa messoria (Harris). The essential pheromone components were (Z)-7- and (Z)-11-hexadecenyl acetates in a ratio of 140, which agreed with an attractant blend developed empirically by field testing the attractancies of synthetic blends. The pheromone component, (Z)-11-hexadecenol, improved the attraction of darksided cutworm males whereas the components (Z)-9-tetradecenyl acetate and (Z)-7-dodecenyl acetate inhibited their attraction. The other pheromone-like compounds identified in the female extracts had no obvious effect on the attraction of darksided cutworm males. Three compounds that functioned as parapheromones when substituted for (Z)-7-hexadecenyl acetate in the two-component blend were (Z)-7-pentadecenyl, (Z)-7-tetradecenyl, and (Z)-7-tridecenyl acetates. (Z)-11-hexadecenal was not detected in the female extracts, but it had a synergistic effect on the attraction of darksided cutworm moths and inhibited the attraction of male moths of a nontarget species,Helotropha reniformis (Grote). As a trap bait for monitoring purposes, we recommend a four-component blend of (Z)-7-hexadecenyl acetate, (Z)-11-hexadecenyl acetate, (Z)-11-hexadecenol, and (Z)-11-hexadecenal at 12.5, 500, 1, and 10 g/red rubber septum dispenser containing 5 g of antioxidant 2,6-tert-butyl-4-methyl phenol. This blend is effective under field conditions for at least six weeks.     

Biological activity of synthetic hydrocarbon mixtures of cuticular components of the female housefly (Musca domestica L.)

Mixtures of (Z)-9-alkenes (C₂₁-C₃₃),n-alkanes (C₂₁-C₃₃), and mono- and dimethylalkanes (C₂₇, C₂₉), as components of the cuticular lipids washed from the female housefly (Musca domestica L.), were synthesized and assayed for their biological activity on male houseflies. The (Z)-9-alkenes and their hydrogenatedn-alkanes were synthesized from jojoba wax components by the appropriate chain elongation. The methylalkanes were prepared by Grignard coupling reaction of the appropriate alkyl halides, catalyzed by Li₂CuCl₄. Six- to 7-day-old virgin male houseflies exhibited the highest mating strike activity toward 6- to 7-day-old virgin females. The mating strike activity of the synthetic hydrocarbons was studied by exposing 6- to 7-day old virgin males to petrol-ether-rinsed 1 to 2-day-old dead females treated with these chemicals. (Z)-9-Tricosene was the most active hydrocarbon tested when it was applied in amounts of 10 g to a washed dead female. Amounts of 5 g of (Z)-9-tricosene did not cause sexual activity in the males. Mixture of (Z)-9-alkenes showed low activity when applied at 10-g amounts. However, when mixtures were made of 5 g of (Z)-9-tricosene with 5 fig of each of certain mixtures of (Z)-9-alkenes, the striking activity became as high as that of 10 g of (Z)-9-tricosene. This might be a synergism effect. The mixtures ofn-alkanes, as well as the mono- and dimethylalkanes, showed moderate activity. When (Z)-9-tricosene was added to these materials no increase in male activity was observed.     

Aggregation Pheromone of the Cereal Leaf Beetle: Field Evaluation and Emission from Males in the Laboratory

The previously identified, male-specific compound of the cereal leaf beetle (CLB, Chrysomelidae; Oulema melanopus), (E)-8-hydroxy-6-methyl-6-octen-3-one, was studied further with respect to field activity and emission rate from male beetles. In a 5-week field experiment in Oregon, the compound was shown to function as an aggregation pheromone in attracting male and female CLBs migrating from overwintering sites in spring. Traps baited with the synthetic compound (500 g per rubber septum) caught 3.3 times more CLBs than control traps. Lower doses of the pheromone (50 and 150 g) were less attractive than the 500 g dose. One relatively abundant, volatile compound from the host plant (oats), (Z)-3-hexenyl acetate, that elicited responses from beetle antennae was not attractive, either by itself or as a synergist of the pheromone. Both sexes were captured about equally for all treatments. We also measured daily pheromone emission by male beetles in the laboratory. Individual males feeding on oat seedlings under greenhouse conditions emitted as much as 6 g per day, which is about 500 times higher than had been previously observed under incubator conditions. The pheromone emission rate was at least five times higher during the day than at night, and in one male, emission spanned a period of 28 d. The release rate of synthetic pheromone from the 500 g septa was very similar to the maximum from single males; thus, future experiments should evaluate even higher doses. The field results indicate that the pheromone has potential as a monitoring tool for early detection of CLBs as they move from their overwintering sites into newly planted cereal crops in spring.     

Oriental fruit moth pheromone component emission rates measured after collection by glass-surface adsorption

We collected and quantified both synthetic and natural Oriental fruit moth [Grapholitha molesta (Busck)] sex pheromone components in 250-ml round-bottom flasks by hexane rinsing of compounds adsorbed on the glass walls. This simple procedure collected 100% of the pheromone evaporated inside the flask and was useful for quantifying both nanogram and microgram amounts of emitted pheromone. Emission rates of (Z)-8-dodecenyl acetate from 1000, 100, and 10 g-loaded rubber septa were 219, 12, and 1.2 ng/hr, respectively.G. molesta females emitted this component at 3.2 ng/hr, close to the emission rate from a 10 g-loaded septum, which evokes long-range and close-range behaviors in the male. The corresponding alcohol, (Z)-8-dodecenyl alcohol, was emitted from rubber septa ca. 3 times faster than the acetate.Lepidoptera: Tortricidae.Paper of the Michigan State Agricultural Experiment Station.     

Nantucket pine tip moth,Rhyacionia frustrana: Identification of two sex pheromone components

Two compounds identified as components of the sex pheromone system ofRhyacionia frustrana are (E)-9-dodecen-1-yl acetate (I) and (E)-9,11-dodecadien-1-yl acetate (II), which were found in female gland extracts in the ratio of 964, respectively. The identifications were based on chemical and instrumental analyses, electroantennogram studies, and field trapping tests. The optimum ratio for trapping maleR. frustrana is the range of 955 to 97.52.5 (III), when dispensed from rubber septa at a loading of ca. 1000/g/lure. In addition to these two compounds, evidence was obtained for the presence of dodecan-1-ol and (E)-9-dodecen-1-ol in female tip extracts and in female effluvium, and for dodecan-1-yl acetate in female tip extracts.Lepidoptera: Tortricidae: Olethreutinae.Supported in part by the Rockefeller Foundation and by National Science Foundation grants GB-38020 and PCM 78-13241.     

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.     

Synergistic Sex Pheromone Components of White-Spotted Tussock Moth, Orgyia thyellina

In 1996, the exotic white-spotted tussock moth (WSTM), Orgyia thyellina (Lepidoptera: Lymantriidae), was discovered in Auckland, New Zealand. Because establishment of WSTM would threaten New Zealand's orchard industry and international trade, eradication of WSTM with microbial insecticide was initiated. To monitor and complement eradication of WSTM by capture of male moths in pheromone-baited traps, pheromone components of female WSTM needed to be identified. Coupled gas chromatographic–electroantennographic detection analysis of pheromone gland extract revealed several compounds that elicited responses from male moth antennae. Mass spectra of the two most EAD-active compounds suggested, and comparative GC-MS of authentic standards confirmed, that they were (Z)-6-heneicosen-11-one (Z6–11-one) and (Z)-6-heneicosen-9-one, the latter termed here thyellinone. In field experiments in Japan, Z6–11-one plus thyellinone at a 100:5 ratio attracted WSTM males, whereas either ketone alone failed to attract a single male moth. Addition of further candidate pheromone components did not enhance attractiveness of the binary blend. Through the 1997–1998 summer, 45,000 commercial trap lures baited with 2000 g of Z6–11-one and 100 g of thyellinone were deployed in Auckland towards eradication of the residual WSTM population.Dedicated to my dear mother in honor of her 75th birthday     

Dihydromatricariate-based triglycerides,glyceride ethers,and waxes in the australian soldier beetle,Chauliognathus lugubris (Coleoptera: Cantharidae)

The soldier beetleChauliognathus lugubris is shown to contain triglycerides and glyceride ethers of 8-dihydromatricaria acid, and waxes of the C₁₂ homolog, of this acid, as well as the previously reported free acid. The triglycerides contain one, two, or three dihydromatricariate moieties, with any remaining positions esterified with normal fatty acids. The glyceride ethers were monostearyl ethers of glycerol esterified with dihydromatricaria acid and oleic or linoleic acid. The waxes, which also include a dihydromatricaria chromophore in the alcohol moiety, occur only in the females and are present in paired accessory glands in the abdomen. The ethers are restricted to females and appear to be associated with developing eggs. The triglycerides are much more abundant in females than males. Triglycerides, glyceride ethers, and waxes represent about 95% of the dihydromatricariate moiety (average, ca. 590 g) in females with free acid the remainder; in males free acid is present to over 50% (ca. 22 g) and the remainder is triglyceride (ca. 15 g). Larvae contain mainly tridihydromatricariate-substituted triglyceride and a smaller quantity of the free acid.     

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.     

The influence of a queen-produced substance, 9HDA,on swarm clustering behavior in the honeybeeApis mellifera L.

The effect of enantiomers of the queen-produced substance, 9-hydroxy-(E)-2-decenoic acid (9HDA) on swarm clustering behavior of the honeybeeApis mellifera was studied. Caged queens were removed from the swarms at the start of each test and were replaced with small Petri dishes containing one of the following treatments: 100 gS(+) enantiomer of 9HDA, 100 gR(-) enantiomer of 9HDA, 200 g racemic (R, S) 9HDA, and a vehicle-treated control. Each swarm was considered to have dispersed when it had lost 50% of its starting weight. All treatments with 9HDA resulted in significantly longer swarm aggregation when compared with the control. Enantiomers were not shown to have different effects at theP 0.05 level of significance. However, observations on swarm behavior indicated that theR(-) enantiomer was the most active in retarding swarm dispersal.     

Sex pheromone of the black cutworm moth,Agrotis ipsilon

(Z)-7-Dodecen-1-yl acetate (I) and (Z)-9-tetradecen-1-yl acetate (II) have been identified as sex pheromone components of the black cutworm moth,Agrotis ipsilon (Hufnagel). They are emitted by the female in approximately a 51 ratio. Differential saturation studies with male antennae suggest that there are two different acceptor sites for the two pheromone components. The most effective lures found in field trapping tests were 30 g of I plus 10 g of II on a rubber septum, and a 31 mixture of I and II dispensed from a 0.2-mm-ID glass capillary tube sealed at one end.Lepidoptera: Noctuidae.Supported at Geneva, in part by the Rockefeller Foundation and by National Science Foundation Grant GB-38020; and at Wooster, in part by Environmental Protection Agency Grant EPA R802547 and by USDA Cooperative State Research Service Grant 316-15-99. Approved by the Director of the New York State Agricultural Experiment Station for publication as Journal Paper3186. Approved for publication as Journal Article113-78 of the Ohio Agricultural Research and Development Center, Wooster, OH 44691.     

Geographic Variation in Sex Pheromone of Asian Corn Borer, Ostrinia furnacalis, in Japan

Geographic variation in the sex pheromone of the Asian corn borer, Ostrinia furnacalis (Guenée), was surveyed in populations sampled at four locations ranging from 39.7°N to 32.9°N in Japan. The sex pheromone of the three northern populations was composed of (E)- and (Z)-12-tetradecenyl acetates with a mean E proportion of 36–39%. The southernmost population (Nishigoshi) had the same components but with a significantly higher E composition of 44%. The frequency distribution of the E ratio in the Nishigoshi population exhibited a small peak near 38% and a major peak near 46%. A family-wise analysis of the sex pheromone of this population confirmed that there were two distinct phenotypes regarding the E ratio. An 46% E strain inhabits southern parts of Japan, in addition to an 38% E strain, which seems to be predominant in other regions of Japan.     

Variation in aphid alarm pheromone content among glandular and eglandular-hairedMedicago accessions

Pea (Acyrthosiphon pisum Harris) and blue alfalfa aphid (A. kondoi Shinji) deterrency in alfalfa (Medicago saliva L.) may result from incorporating higher levels of the aphid alarm pheromone,(E)--farnesene relative to(E)--caryophyllene. We evaluated five eglandular and two glandular-haired alfalfa accessions for differences in(E)--farnesene and(E)--caryophyllene content under glasshouse conditions using supercritical fluid extraction and gas chromatography. In addition, pea and blue alfalfa aphid olfactory behavioral tests were conducted uponMedicago species containing different ratios of(E)--famesene relative to(E)--caryophyllene. No differences in(E)--caryophyllene content were observed among the seven entries (=0.42 ng/g plant material). Significant differences (P 0.05) among entries were observed for(E)--famesene content, with KS94GH6 exhibiting the highest (1.18 ng/g), and CUF 101 the lowest levels (0.35 ng/g). Elite tetraploid sources possessed significantly lower levels (=0.42 ng/g) of(E)--farnesene than did wild and cultivated diploid accessions (=0.83 ng/g). Olfactory behavioral tests for both the pea and blue alfalfa aphids demonstrated KS94GH6 repelled aphids while cultivated alfalfa types attracted aphids in each case. Previously demonstrated aphid resistance in diploid KS94GH6 may result from superior(E)-- farnesene levels, but(E)--farnesene is probably not a factor in cultivated alfalfa resistance. Finally, accession KS94GH6 could act as an excellent germplasm resource for the incorporation of higher(E)--farnesene levels into cultivated alfalfa.Research supported by the New Mexico State University Agricultural Experiment Station.     

Attraction ofOryzaephilus surinamensis (L.) andOryzaephilus mercator (Fauvel) (Coleoptera: Cucujidae) to some common volatiles of food

Responses by adultOryzaephilus surinamensis (L.) andOryzaephilus mercator (Fauvel) to various food volatiles were assessed by means of a two-choice, pitfall olfactometer. The individual experimental stimuli, all potential products of lipid oxidation, had a range of attractive doses of 1000-fold over the test dose ranges of 0.001–100 gmg, or 0.01–1000 gmg. Of 13 aliphatic C₃-C₁₄ aldehydes and benzaldehyde tested forOryzaephilus spp., 10 C₃-C₁₀ aliphatic aldehydes and benzaldehyde showed some attractiveness for both species. ForO. mercator, nonanal had the lowest lower threshold for positive response at 0.01 g. The addition of small amounts of nonanal or of a 111 mixture of hexanal, octanal, and nonanal to small amounts of cucujolide aggregation pheromones enhanced response by mixed-sexO. mercator to the pheromones. Eleven aliphatic C₂-C₉ free fatty acids showed some attractiveness for bothOryzaephilus spp. Isovaleric acid and valeric acid had the lowest lower thresholds for positive response at 0.1 g forO. mercator andO. surinamensis, respectively. Four olefinic oat volatiles were found to possess various degrees of attractiveness for bothOryzaephilus spp. The data suggest that food volatiles in this study might be used byOryzaephilus spp. as host-finding kairomones in nature.Research supported by the Natural Sciences and Engineering Research Council of Canada, Strategic Grant G0958 and Operating Grants A3881 and A3785.     

Interactions between pheromone traps with different strength lures for the pine beauty moth,Panolis flammea (Lepidoptera: Noctuidae)

Catches of malePanolis flammea in traps baited with lures containing 25 g of sex attractant are enhanced when in the proximity of traps baited with 125-g lures. The degree of enhancement is increased as the intertrap distance is decreased, and when the low-dose trap is upwind of the high-dose one. The patterns of alteration in trap catch suggest that moths initially attracted by one lure may divert into other traps, which may be either upwind of the original trap (overshooting), or downwind (undershooting). Overshooting can result in up to fivefold increases in catch and may provide a useful method for estimating the attractant zone of particular lure/trap combinations.     

Sex pheromone components of the variegated leafroller moth,Platynota flavedana

Female tip extracts of the variegated leafroller moth,Platynota flavedana (Clemens), were analyzed and found to contain a mixture of (E)-11-tetradecen-1-ol and (Z)-11-tetradecen-1-ol (91), as well as a mixture of (E)-11-tetradecenyl acetate and (Z)-11-tetradecenyl acetate (2-31). Small amounts of tetradecen-1-ol and tetradecyl acetate probably are also present. In the field, a mixture of the two alcohols (8416,EZ ratio) attracted significantly more male moths of this species than any other mixture tested. The data indicate that the acetates are probably not used as pheromone components.Lepidoptera:Tortricidae:Tortricinae.This research was supported in part by the Rockefeller Foundation and by NSF Grant No. GB-38020.