Evidence for a multicomponent sex pheromone in the yellowheaded spruce sawfly

The existence of a female-produced sex pheromone in the yellowheaded spruce sawfly,Pikonema alaskensis (Rohwer) (Hymenoptera: Tenthredinidae) was demonstrated by field and greenhouse bioassays. Virgin females, their empty cocoons (with which they were confined during handling procedures), and the hexane extract of these cocoons were attractive in the field. The only Florisil fraction of this extract consistently attractive by itself was that eluted with hexane, but three, more polar fractions (eluted with 5%, 25%, and 50% ether in hexane) each synergized the hexane fraction, increasing bioassay responses 10–30 times. Fractions derived directly from virgin females yielded comparable results. The greenhouse data corroborated the field data, except that the 5% ether-hexane fraction, while very synergistic in the field, was consistently inactive in the greenhouse.     

Hydrocarbon components of the yellowheaded spruce sawfly sex pheromone

The primary sex pheromone of the yellowheaded spruce sawfly,Pikonema alaskensis (Rohwer) (Hymenoptera: Tenthredinidae), was found to include a series of straight-chain hydrocarbon dienes, all with the double bonds in the 9 and 19 positions and all with the (Z, Z) configuration. The major components, of 29, 31, 33, 35, and 37 carbon atoms, were synthesized. In the field and the greenhouse, the synthetic dienes were far above control levels in activity but, at least during the first hours of bioassay, were somewhat less active than the female-derived materials on a weight basis. In the field, a mixture of all five synthetic dienes, in the proportions found in the females, was more attractive than any single one, on a mole basis. In addition, (Z, Z)-9,19 dienes of 28, 30, 32, 34, 36, 38, and 39 carbons have been detected in females in minor amounts. The first five were bioassayed, and each was found to be similar in activity to the 35-carbon component when compared on a weight basis. The synthetic dienes, while active by themselves, were strongly synergized by two, more polar, Florisil fractions derived from females. Experimental design considerations are discussed.     

Chiral specificity of the sex pheromone of the red-headed pine sawfly,Neodiprion lecontei

The stereospecificity of the sawfly pheromone 3,7-dimethyl-2-pentadecanol acetate againstNeodiprion lecontei was studied. Twoerythro and a 11 mixture ofthreo isomers (C-2 and C-3) were synthesized for this purpose. It was found that only one isomer with (–)-erythro configuration (2S, 3S) had biological activity. The potency of this synthetic pheromone was roughly identical to the one shown by the naturally occurring pheromone in this species.     

Field and electroantennogram responses of the red-headed pine sawfly,Neodiprion lecontei (Fitch), to optical isomers of sawfly sex pheromones

Sawfly sex pheromones, the acetate and propionate esters of 3,7-dimethylpentadecan-2-ol, were field tested for activity towardNeodiprion lecontei (Fitch). Only the acetate form of the 2S,3S,7S isomer was active. Field catch decreased with the addition of the 2S,3R,7(R/S) acetate isomer sample. Electroantennogram recordings showed a positive correlation between response and degree to which the chirality of each isomer resembled the attractive isomer.     

Ethyl (Z)-9-hexadecenoate a sex pheromone ofSyndipnus rubiginosus,a sawfly parasitoid

A female-produced sex pheromone ofSyndipnus rubiginosus Walley (Hymenoptera: Ichneumonidae), a parasitoid of the yellowheaded spruce sawfly,Pikonema alaskensis (Rohwer) (Hymenoptera: Tenthredinidae), was isolated and identified from hexane extracts of 250 virgin females. Column chromatography (Florisil), gas chromatography, mass spectrometry, high performance liquid chromatography, and ozonolysis indicated the structure was ethyl (Z)-9-hexadecenoate. The optimum male response is at 300–1000 ng (3–10FE). No cross-attraction betweenS. rubiginosus and the sympatric sawfly parasitoidS. gaspesianus (Provancher) could be demonstrated.Hymenoptera: Ichneumonidae.Paper No. 13,232 Scientific Journal Series, Minn. Agric. Exp. Stn., St. Paul, Minnesota 55108. Research supported by C.K. Blandin Foundation of Grand Rapids, Minnesota.     

Evidence for the controlled release of a crustacean sex pheromone

Evidence for the controlled release of a crustacean sex pheromone: mature malePortunus sanguinolentus (Herbst) did not give the characteristic display described by Ryan (1966) to water from a container with a carried or artificially restrained premolt female. However, the sex pheromone was still present in the urine of the restrained female, suggesting that she inhibits the emission of the sex pheromone by regulating her urine flow.Based on part of a dissertation presented by the author in partial fulfillment of the requirements for the doctoral degree in zoology at the University of Hawaii.     

Preparation and use of sex attractants for four species of pine sawflies

Sex attractants were prepared for four species of diprionid sawflies,Neodiprion lecontei, N. swainei, N. sertifer, andDiprion similis, by esterification of both synthetic and naturally occurring alcohols. For the first two species totally synthetic (racemic) compounds were attractive to males in the field. For the latter two species, none of the synthetic compounds tested were consistently attractive. For these, effective attractants were prepared by saponification and reesterification of crude extracts from female insects.Hymenoptera: Diprionidae     

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 the sex pheromone of threeMatsucoccus pine bast scales

Matsucoccus resinosae in the United States,M. matsumurae in China, andM. thunbergianae in Korea use (2E, 4E)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one (1) (matsuone) as the primary component of their sex attractant pheromones. The structure was postulated from mass and NMR spectra and confirmed by synthesis of analogs3, (2E,4E)-4,6,11,12-tetramethyl-2,4-tridecadien-7-one, and4, (2E,4Z)-4,6,11,12-tetramethyl-2,4-tridecadien-7-one. Both analogs were attractive to the males ofM. resinosae in laboratory bioassays and toM. matsumurae in laboratory and field tests, but the 4Z analog (4) was much less so than the 4E analog (3) and had inhibitory effects at high concentrations. Dodecanol, isolated from aeration and solvent extracts of femaleM. resinosae, evoked characteristic wing-raising by pedestrian males, but the role of this response was not determined.     

Laboratory and field tests with the synthetic sex pheromone of threeMatsucoccus 1 pine bast scales

Matsunone, (2E,4E)-4.6,10,12-tetramethyl-2,4-tridecadien-7-one, is the primary sex pheromone ofMatsucoccus resinosae, M. thunbergianae, andM. matsumurae. The synthetic compound was tested in the laboratory and in field tests with all three species, and significantly more males responded to synthetic matsuone than to controls. The attraction of synthetic matsuone to males in field tests was not significantly different from that of virgin females at the same matsuone release rate. An analog of matsuone previously shown to be biologically active was also tested in the laboratory withM. resinosae andM. thunbergianae, and field tested withM. resinosae. The active analog required a dose approximately 100 times greater than matsuone to yield maximum laboratory bioassay response, and in field tests, attraction was not significantly different from controls at doses at which matsuone was significantly attractive.Homoptera: Coccoidea: Margarodidae.Deceased.     

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.     

Identification of sex pheromone components of jack pine budworm,Choristoneura pinus pinus freeman

Chemical identification and field-trapping experiments have shown that a blend of 8515 (E,Z)-11-tetradecenyl acetates and 8515 (E,Z)-11-tetradecen-1-ols (in a 91 ratio) are female sex pheromone components for jack pine budworm,Choristoneura pinus pinus. This blend of chemicals, formulated in PVC (0.1 %, w/w) sources is as effective a trap bait as virgin females. Preliminary wind tunnel observations have indicated that this blend, effective as a trap bait, is not equivalent to females.Lepidoptera: Tortricidae.     

Identification and field evaluation of the compounds comprising the sex pheromone of the female boll weevil

The terpenoid compounds (+)-cis-2-isopropenyl-1-methylcyclo-butaneethanol (I), (Z)-3,3-dimethyl-A-cyclohexaneethanol (II), and -caryophyllene were isolated from frass of the female boll weevil (Anthonomus grandis Boheman). In laboratory bioassays, a mixture of these components attracted primarily males, whereas the male pheromone, grandlure, attracted primarily females. The addition to the cotton bud hydrocarbons, -pinene, myrcene, andl-lim-nene, improved the response by males so that the potency of the mixture was comparable to that of grandlure for females. In field tests, I + II + hydrocarbons attracted both sexes, but grandlure alone and grandlure + hydrocarbons were more effective.Coleoptera: Curculionidae.In cooperation with the Mississippi Agricultural and Forestry Experiment Station, Mississippi State, Mississippi 39762.Mention of a commercial or proprietary product in this paper does not constitute endorsement of this product by USDA.     

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.     

Chirality of israeli pine bast scale,Matsucoccus josephi (homoptera: Matsucoccidae) sex pheromone

The absolute configuration of the sex pheromone of the Israeli pine bast scale,Matsucoccus josephi, was determined as (2E,5R,6E,8E)-5,7-dimethyl-2,6,8-decatrien-4-one, designated here asR-E with 10% (2E,5S,6E,8E)-5,7-dimethyl-2,6,8-decatrien-4-one, designated asS-E. The chirality of the quantitatively minorZ isomer was (2E,5R,6Z,8E)-5,7-dimethyl-2,6,8-decatrien-4-one (R-Z). Chiral assignments were made by comparative gas chromatographic (GC) analysis of naturalM. josephi pheromone with stereoselectively synthesized stereoisomers on a chiral Cyclodex-B column, which separated the enantiomers with baseline resolution. In gas chromatographic-electroantennographic detection (GC-EAD) analysis of the racemicZ andE isomers, the latter elicited the stronger antennal response by maleM. josephi. In GC-EAD of all four stereoisomers, employing the chiral column,R-E was the most active stereoisomer. In field testsR-E attracted 10 times more males ofM. josephi than didS-E. The racemicE/Z pheromone mixture, containing all four stereoisomers in approximately equal amounts, attracted as many maleM. josephi as did an equivalent amount ofR-E, indicating that the other stereoisomers are not inhibitory. The same keto-diene moiety with the same chiral center and configuration in all three known Matsucoccidae sex pheromones implies a common biosynthetic pathway and phylogenetic relationship.Contribution from the Agricultural Research Organization, the Volcani Center, No. 1496-E, 1994 series.Part of the work was performed during a sabbatical leave of E.D. at Simon Fraser University.     

Biosynthesis of sex pheromone components and glycerolipid precursors from sodium [1-14C]acetate in redbanded leafroller moth

Sodium [1-¹⁴C]acetate in water-dimethyl sulfoxide (11) was applied topically to sex pheromone glands ofArgyrolaenia velutinana. Radiolabel was incorporated into the pheromone components (Z)-11-tetradecenyl acetate and (E)-11-tetradecenyl acetate, and also into triacylglycerols, diacylglycerols, ethanolamine phosphatides, and choline phosphatides. In the triacylglycerols, radiolabel appeared in (Z)-11-tetradecenoate, (E)-11-tetradecenoate, tetradecanoate, hexadecanoate, and octadecanoate. In the choline phosphatides, the same acyl moieties incorporated radiolabel but at lower levels. In the diacylglycerols and ethanolamine phosphatides, only the radiolabel in hexadecanoate and octadecanoate was above the limit of detection. At different times following application of sodium [1-¹⁴C]acetate, the relative proportions of labeled (Z)-11-tetradecenyl acetate and (E)-11-tetradecenyl acetate changed very little, but the relative proportions of labeled fatty acyl moieties in the triacylglycerols and choline phosphatides changed markedly. After 8 min, triacylglycerols had incorporated about equal amounts of radiolabel into (Z)-11-tetradecenoate, (E)-11-tetradecenoate, and tetradecanoate. As the incubation time was increased, triacylglycerols accumulated proportionately more radiolabeled (E)-11-tetradecenoate than (Z)-11-tetradecenoate, and accumulated proportionately less radiolabeled tetradecanoate. In the choline phosphatides, at all times of incubation the amount of radiolabel incorporated into (Z)-11-tetradecenoate was small but above the limit of detection, and the amounts of radiolabel in (E)-11-tetradecenoate and tetradecanoate were smaller and often below the limit of detection. In both the triacylglycerols and the choline phosphatides, the relative proportion of radiolabeled hexadecanoate decreased with time, and that of octadecanoate increased.     

Interspecific attractivity of female sex pheromone components ofPeriplaneta americana

Female sex pheromones ofPeriplaneta americana, P. australasiae, andBlatta orientalis elicit locomotion and upwind orientation in conspecific males. Interspecific attraction between these species was observed in a wind tunnel assay for most species combinations, with the exception ofP. australasiae males not being attracted toP americana females. The role of twoP. americana sex pheromone components, periplanone-A (PA) and periplanone-B (PB) in male attraction was analyzed. PA induced locomotion in males of all three species, with highest threshold concentration inP. americana. PB was effective inP. americana andB. orientalis, but not inP. australasiae. Experiments with mixtures of both components confirmed an inhibitory influence of PB onP. australasiae males when it was added to PA in a ratio of 31 or higher. SinceP. americana andP. australasiae have been found to be syntopous, and their daily mating periods overlap, the female sex pheromone ofP. americana is discussed as an isolating factor between both species.     

Identification of a sex pheromone produced by female velvetbean caterpillar moth

A sex pheromone produced by female velvetbean caterpillar moths,Anticarsia gemmatalis Hübner, that attracts conspecific males was isolated and identified as a blend of (Z,Z,Z)-3,6,9-eicosatriene and (Z,Z,Z)-3,6,9-heneicosatriene in a ratio of ca. 53, respectively, when combined. The synthesized compounds elicited responses by velvetbean caterpillar moth males equivalent to those elicited by females in both laboratory wind tunnel bioassays and field trapping experiments.Lepidoptera: Noctuidae.Mention of a commercial or proprietary product does not constitute an endorsement by the USDA.Employed through a cooperative agreement between the Department of Entomology & Nematology, University of Florida, and the Insect Attractants, Behavior, and Basic Biology Research Laboratory, Gainesville, Florida 32604.     

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.     

A high-efficiency collection device for quantifying sex pheromone volatilized from female glands and synthetic sources

A high-efficiency collection device for sex pheromones volatized from forcibly extruded female glands is described. Filtered nitrogen gas is the carrier and glass wool the adsorbent. Small quantities of distilled carbon disulfide are used to rinse the glass wool. Recovery efficiency of synthetic compounds was usually 90–100%, and a mean of 2.4 ± 0.65 SD ng/min of (Z)-7-dodecenyl acetate was recovered in emissions from individualTrichoplusia ni (Hubner) glands.