Sex Pheromone Research Papers - Academia.edu (original) (raw)

The sex pheromone of females of the carob moth, Ectomyelois ceratoniae, was identified to be a mixture of (Z,E)-9,11,13_tetradecatrienal, (Z,E)-9,11-tetradecadienal and (Z)-9-tetradecenal in the ratio of 1O:l:l. A synthetic blend proved... more

- by
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- Zoology, Organic Chemistry, Chemical Ecology, Tobacco

The sex pheromone emitted by the female oleander scale, Aspidiotus nerii (Homoptera, Diaspididae), has been isolated and characterized as (1R,2S)-cis-2-isopropenyl-1-(4‧-methyl-4‧-penten-1‧-yl)cyclobutaneethanol acetate by using advanced MS and NMR spectroscopic methods, as well as a variety of microderivatization sequences. The structure has been confirmed by stereo- and enantioselective synthesis of the four possible stereoisomers. The absolute configuration has been determined by comparison of the activity of the cis (1S,2R) and (1R,2S) enantiomers with that exhibited by the natural material in greenhouse bioassays and field tests. The structure of this sesquiterpenoid pheromone is new in the coccids and in the pheromone field in general.

- by Angel Guerrero
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- Multidisciplinary, Sex Pheromone

Females of the European pine sawfly, Neodiprion sertifer (Geoffr.) (Hymenoptera: Diprionidae), were released and observed inside and outside ( = control) of areas treated with their sex pheromone for the purpose of mating disruption. In 1992 and 1993, respectively, 0 and 2.5% of the females were observed mating in the pheromone treated area during the first day, compared with 28 and 26% in the control area. Of the females that mated, approximately 50% stayed on their twigs and oviposited, while the remaining 50% disappeared. Significantly more females disappeared from their twigs inside the treated area compared to the control area in both years. No difference was found in the proportion of unmated females ovipositing (2-12%) between the treated and the control area. Predation was responsible for much of the disappearance, but deliberate dispersal was also noted. Mating and dispersal in female N. sertifer are discussed in relation to population density and overall fitness.

- by Erling Jirle
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- Zoology, Population Density, Insect Behavior, Sex Pheromone

In Nauphoeta cinerea, male calling behavior is associated with sex pheromone release by the sternal glands. The male pheromone that attracts females from a distance is a mixture of 2-methylthiazolidine and 4-ethylguaiacol. It is active at very low concentrations, 0.05 and 0.01 ng, respectively. Two other compounds, 3-hydroxy-2-butanone and 2-methyl-2thiazoline, act at close range, keeping the female in the vicinity of the male. The function of the volatile pheromone and those of previously described contact pheromones are discussed in regard to their possible involvement in the establishment of male dominant-subordinate relationships.

- by Daniel Sirugue and +1
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- Chemical Ecology, Chemical, Biological Sciences, Environmental Sciences

Field tests were carried out to determine whether pheromone traps, baited with (Z,E)-9,12-tetradecadienyl acetate (Z9,E12-14:Ac) impregnated in rubber septa (Maavit, Israel), could provide a reliable tool for monitoring the raisin moth, Cadra figulilella (Gregson), in date palm plantations. No significant differences were detected between captures of males in traps baited with 1 or 10 mg pheromone/dispenser. However, traps baited with 1 mg pheromone captured significantly more males than those baited with 0.l mg pheromone/dispenser. No differences were found between captures of males in traps hung at a height of 8 m (near the bunches) or 2-3 m (on palm trunks). Two peaks of male capture were detected, one in May-June and the other during September-October (ripening period). Results indicate a positive relationship between captures in traps and infestation levels by larvae. Pheromone traps baited with 1 mg Z9,E12-14:Ac impregnated in rubber septa and hung on palm trunks (at a height of 2-3 m), were very useful for monitoring C. figulilella populations and for determining the accurate timing of insecticide applications.

- by D. Blumberg
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- Plant Biology, Date Palm, Sex Pheromone, Population Monitoring

We evaluated the attraction of male almond seed wasp Eurytoma amygdali to the synthetic alkadienes (Z ,Z )-6,9-tricosadiene and (Z ,Z )-6,9pentacosadiene and their blend in almond orchards using baited rubber septa attached to cardboard rectangular adhesive traps. The two alkadienes were recently isolated from virgin female whole body extracts and SPME collected volatiles. The alkenes (Z )-9-tricosene, (Z )-9-pentacosene, and (Z )-9-heptacosene, present in female extracts, were also added to the blend of the alkadienes and tested. The alkadienes tested individually attracted males when the traps were baited with doses ranging from 10 to 30 mg/trap. The maximum number of males was attracted to traps baited with 10 mg of a (Z ,Z )-6,9-C 23:2 :(Z ,Z )-6,9-C 25:2 blend at a ratio of 7:3. Results with the three alkenes added to the blend were inconclusive because of low populations. The present study on E. amygdali is the first one reporting attraction of males to synthetic sex pheromone components in field trials for a Eurytomidae species. The synthetic alkadienes blend offers the potential to develop an effective system for monitoring populations of the almond seed wasp in almond orchards.

- by Nickolas Kavallieratos and +1
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- Chemical Ecology, Population Dynamics, Environmental Monitoring, Biological Sciences

Field evaluations demonstrate that the addition of the minor pheromone component (3E,8Z)-tetradecadien-1-yl acetate to the major component (3E,8Z,11Z)-tetradecatrien-1-yl acetate does not significantly increase the trap catches of Tuta absoluta males in the field. The triene acetate itself is highly attractive, catching about 869 ± 255 males per trap in three consecutive nights. The addition of two isomers of the minor component (3E,8Z)-tetradecadien-1-yl acetate, (3E,11Z)-tetradecadienyl-yl acetate and (8Z,11Z)-tetradecadien-1-yl acetate, to the major component (3E,8Z,11Z)-tetradecatrien-1-yl acetate also did not significantly alter the number of the males caught in the traps.

- by Miguel Michereff-Filho
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- Chemical Ecology, Control, Chemical, Lepidoptera

The currant shoot borer, Lampronia capitella (Lep., Prodoxidae), is an important pest of currants, Ribes spp., in northern Europe. Oviposition was studied in cage experiments and the flight period was monitored in field studies using pheromone-baited traps. Blackcurrant, Ribes nigrum, was the host species in both studies. The total egg supply of females was on average 107 eggs and oviposition started 2-5 days after emergence. About 60% of the eggs were laid during the first day of the oviposition period. Eggs were laid in currant fruitlets, in batches comprising several, usually four to seven eggs. The flight period started shortly after the end of the flowering period of blackcurrant, and lasted for about 3 weeks.

- by Erling Jirle
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- Zoology, Applied Entomology, Sex Pheromone, Fecundity

The present study was undertaken to investigate possible integration of synthetic pyrethroids with biological control of Sesamia nonagrioides Lefebvre (Lepidoptera: Noctuidae) by the egg parasitoid Telenomus busseolae Gahan (Hymenoptera: Scelionidae). The effects of two commonly used synthetic pyrethroids, deltamethrin (Decis Jet 15 EC) and cyfluthrin (Bayteroid 5 EC), on the parasitoid were studied. Lethal concentrations (LC 25 ) were estimated for both insecticides, and their sub-lethal effects on some biological parameters and behavioral responses to different kairomonal cues mediating host location were investigated. Parasitoid females exposed to cyfluthrin (LC 25 ) parasitized significantly fewer eggs than untreated females, whereas neither the level of emergence from parasitized eggs nor the sex ratio of the offspring was affected by the insecticides. None of the above biological parameters were significantly affected by deltamethrin (LC 25 ). Both insecticide treatments reduced the longevity of the parasitoids. The effects of both insecticides (LC 25 ) on the behavioral responses of parasitoid females to the sex pheromone of S. nonagrioides, which acts as a long-distance kairomone, were investigated in a Y-tube olfactometer. Cyfluthrin-treated parasitoids failed to respond to the host pheromone, whereas deltamethrin-treated females responded similarly to untreated females. In addition, sub-lethal effects of pyrethroids on parasitoid arrestment behaviors were evaluated in an open arena containing abdominal scales from virgin female moths, which are a source of short-distance kairomone for the parasitoid. No significant differences in arrestment behaviors (residence time, linear speed) were found. Based on our results, possible consequences of treating maize with cyfluthrin or deltamethrin on the effectiveness of surviving T. busseolae in the field are discussed.

- by Gianandrea Salerno and +1
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- Zoology, Biological Control, Maize, Sex ratio

The sex attmctant of Scrobipalpuloides absoluta females is a 90:10 mixture of (3E,8Z, I IZ)-3,8,11-tetradecatrien-l-yl acetate and (3E,8Z)-3,8tetradecadien-l-yl acetate. Tetradecadienyt acetates bearing 8Z, I IZ; 3E,8Z; and 3E, 1 IZ double bonds were synthesized by stereospecific procedures; the mass spectral and gas chromatographic properties of the 3E,SZ isomer were found to be congruent with those of the tetradecadienyl acetate from S. absoluta. In wind tunnel bioassays, a 10:1 mixture of synthetic (3E,8Z, I IZ)-3,8,1 l-tetradecatrien-l-yl acetate and (3E,8Z)-3,8-tetradecadien-l-yl acetate was highly attractive to S. absoluta males. Interestingly, the presence of (8Z, I IZ)-8,1 l-tetradecadien-l-yl acetate (10%) inhibited the response to (3E,8Z, 1 IZ)-3,8, I 1 -tetradecatrien-l-yl acetate completely.

- by David Šaman and +1
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- Chemical Ecology, Chemical, Lepidoptera, Biological Sciences

Twelve products related to the sex pheromone main components (Z)-9-and (Z)-I l-tetradecenyl acetate (Z9-14 : Ac and Z11-14 : Ac, respectively), were identified in female pheromone gland extracts of the laboratoryreared 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-hexadeeenyl acetate, and saturated acetates of 12-22 carbons. The ratio of Z9-14 : Ac to Z11-14 : Ac in individuals varied from 3.5 : 1 to 11 : 1 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. Z9-14:Ac, Z11-14:Ac 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.

- by P. Charmillot
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- Chemical Ecology, Biological Sciences, Environmental Sciences, Individual variation

The small fruit tortrix, Grapholita lobarzewskii (Nowicki) (Lepidoptera Tortricidae), is a serious problem in the organic apple or-chards of the Friuli Venezia Giulia region (northeastern Italy), particularly in hilly areas. Three trials... more

- by Francesco Pavan
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- Zoology, Organic agriculture, Sex Pheromone, Damage Control

The yellow-legged clearwing (YLC) Synanthedon vespiformis (Lepidoptera: Sesiidae) occurs in the Mediterranean and central Europe. It is polyphagous, boring into the woody parts of broadleaf species including forest trees as well as various Rosaceae species. S. vespiformis has been reported as an economically important pest causing severe injury to stone fruit plantations. Many attractants for sesiid species were discovered by random field screening using 2,13-and 3,13-octadecadienyl alcohols, acetates and aldehydes, including one for S. vespiformis; and about 20 sex pheromones of sesiids have been identified so far. In the present study we identified the natural composition of the sex pheromone of YLC laboratory reared females as a blend of E3,Z13-and Z3,Z13-octadecadienyl acetates, at a ratio of 4:1. We developed an efficient lure for monitoring the pest. Pheromone funnel traps with rubber septa, impregnated with 1 mg pheromone blend, efficiently captured males for 10 weeks. Suspension of Shin-Etsu Ò ropes containing a 2:1 blend of E3,Z13-18:Ac and Z3,Z13-18:Ac at 13.74 mg/ha/ h, resulted in shutdown of trap catches in the treated plots and closely situated neighboring plots indicating that mating disruption is feasible.

- by Zvi Mendel
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- Biological Sciences, CHEMICAL SCIENCES, Sex Pheromone, Mating Disruption

The major sex attractant emitted by Scrobipalpuloides absoluta females is shown to be (3E, 8Z,11Z)-3,8,11-tetradeca-trien-l-yl acetate by a novel strategy involving the random reduction of double bonds, followed by methylthiolation of the reduced products. Each female sex gland contains ca. 1-5 ng of this pheromone. This triene ester, synthesized by a stereospecific procedure, shows spectral and gas chromatographic properties identical to those of the natural substance. In field tests and wind tunnel bioassays, the synthetic ester was found to be highly attractive to conspecific males. The male response to this pheromone, however, is restricted to the same early-morning time window during which females exhibit calling behavior.

- by Rosa T. S. Frighetto
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- Organic Chemistry, Magnetic Resonance Spectroscopy, Lepidoptera, Tomato

Plant semiochemicals are known to produce a wide range of behavioral responses in insects. Some insects sequester or acquire host plant compounds and use them as sex pheromones or sex pheromone precursors. Other insects produce or release sex pheromones in response to specific host plant cues, and chemicals from host plants often synergistically enhance the response of an insect to sex pheromones. Plant volatiles can also have inhibitory or repellent effects that interrupt insect responses to pheromones and attract predators and parasitoids to the attacking species after herbivory injury. Here, we review different interactions between plant semiochemicals and insect pheromones, paying attention to those that can result in the development of more efficient and reliable programs for pest control.

- by Angel Guerrero
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- Plant Biology, Pheromones, Insects, Pest control

The role of pheromones in orchestrating social behaviors in reptiles is reviewed. Although all reptile orders are examined, the vast majority of the literature has dealt only with squamates, primarily snakes and lizards. The literature is surprisingly large, but most studies have explored relatively few behaviors. The evolution of chemical signaling in reptiles is discussed along with behaviors governed by pheromones including conspecific trailing, male-male agonistic interactions, sex recognition and sex pheromones, and reptilian predator recognition. Nonreptilian prey recognition by chemical cues was not reviewed. The recent literature has focused on two model systems where extensive chemical ecology studies have been conducted: the reproductive ecology of garter snakes and the behavioral ecology of Iberian lacertid lizards. In these two systems, enough is known about the chemical constituents that mediate behaviors to explore the evolution of chemical signaling mechanisms that affect life history patterns. In addition, these models illuminate natural and sexual selection processes which have lead to complex chemical signals whose different components and concentrations provide essential information about individuals to conspecifics. Reptiles provide excellent candidates for further studies in this regard not only in squamates, but also in the orders where little experimental work has been conducted to date.

- by Robert T. Mason
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- Animal Behavior, Chemical Ecology, Reproduction, Sexual Selection

Leucinodes orbonalis Guenée were found to catch and retain ten times more moths than either Spodoptera or uni-trap designs. Locally-produced water and funnel traps were as effective as delta traps, although 'windows' cut in the side panels of delta traps significantly increased trap catch from 0.4 to 2.3 moths per trap per night. Trap catch was found to be proportional to the radius of sticky disc traps in the range 5 to 20 cm radius, discs with a 2.5 cm radius caught no moths. Wing traps placed at crop height caught significantly more moths than traps placed 0.5 m above or below the crop canopy. Replicated integrated pest management (IPM) trials (3 x 0.5 ha per treatment) were conducted in farmers fields with young and mature eggplant crops. Farmers applied insecticides at least three times a week in all check and IPM plots. In addition pheromone traps were placed out at a density of 100 per ha and infested shoots removed weekly in the 0.5 ha IPM plots. Pheromone trap catches were reduced significantly from 2.0 to 0.4 moths per trap per night respectively in check and IPM plots in a young crop and 1.1 to 0.3 moths per trap per night in check and IPM plots respectively in a mature crop. Fruit damage was significantly reduced from an average of 41.8% and 51.2% in check plots of young and mature crops respectively to 22% and 26.4

- by A. Cork
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- Evolutionary Biology, Zoology, Animal Behavior, Lepidoptera

The brinjal fruit and shoot borer, Leucinodes orbonalis is the major pest of eggplant in South Asia. Analysis of female pheromone gland extracts prepared from insects of Indian and Taiwanese origin confirmed (E)-11-hexadecenyl acetate (E11-16:Ac) as the major pheromone component with 0.8 to 2.8% of the related (E)-11-hexadecen-1-ol (E11-16:OH), as previously reported from Sri Lanka. The average quantity of E11-16:Ac extracted per female was estimated to be 33 ng, with a range of 18.9 to 46.4 ng when collected 2 to 3 hr into the scotophase. In field trials conducted in India, blends containing between 1 and 10% E11-16:OH caught more male L. orbonalis than E11-16:Ac alone. At the 1,000 microg dose, on white rubber septa, addition of 1% E11-16:OH to E11-16:Ac was found to be more attractive to male L. orbonalis than either 0.1 or 10% E11-16:OH. Trap catch was found to be positively correlated with pheromone release rate, with the highest dose tested, 3,000 microg, on white rubber septa...

- by A. Cork
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- Animal Behavior, Chemical Ecology, South Asia, Sri Lanka

Field trials investigating the effect of food baits on catches of Musca domestica at toxic targets impregnated with the female sex pheromone, (Z)-9-tricosene, were conducted in a caged-layer deep-pit poultry unit in southern England. Targets treated with an Alfacron-sugar mixture and baited with 2.5 g of 40% (Z)-9-tricosene beads caught significantly greater numbers of both male and female M. domestica than control targets. Egg and milkbaited targets were less attractive than controls, while brewers yeast slightly increased the numbers of M. domestica attracted. However, the inclusion of brewers yeast in (Z)-9-tricosene-impregnated targets produced a significant reduction in the number of male M. domestica attracted. Increased female attraction was elicited by baiting the targets with 2-phenylethanol, at the quantities of 1 mg and 10 mg. However, 2-phenylethanol had no effect on female attraction when presented in conjunction with (Z)-9-tricosene. The implications of these results in relation to the control of M. domestica populations in poultry units are discussed.

- by Philip Howse
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- Zoology, Entomologia, Field Trial, Sex Pheromone

To contribute to the understanding of the genus Ostrinia (Lepidoptera; Pyralidae) in Japan, we collected larvae of Ostrinia spp. from known host plants and plants not recorded as hosts, and we examined the morphology and sex pheromones of the adults obtained. Consequently, the host plant ranges of the 7 Ostrinia spp. in Japan were clarified, and the sex pheromones of the 5 species O. scapulalis, O. zealis, O. zaguliaevi, O. palustralis and O. latipennis were identified in addition to that of the Asian corn borer O. furnacalis. The phylogenetic relationships of Japanese Ostrinia spp., with reference to the European corn borer O. nubilalis, are discussed based on these findings and results of molecular phylogenetic analyses. * a: identification based on wind-tunnel bioassay. b: based on both wind-tunnel and field trap experiments.

- by Sadahiro Tatsuki
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- Zoology, Lepidoptera, Entomologia, Sex Pheromone

Believe it or not, there is actually a science behind how human pheromones work. How it is produced, transmitted and received including what effects it has on the opposite sex. However, how human pheromones work through biology or human physiology is not what I'm going to talk about. There are already a million articles explaining how human pheromones work by using biology. What I'm going to talk about is how it works using psychology and sociology through my own experiences.

In this study, we have compared the release of sex pheromone from mating disruption dispensers exposed in the field for 12 months and from calling females. The main pheromone component of the grapevine moth, Lobesia botrana (D. and S.) (Lepidoptera: Tortricidae), is (E)-7,(Z)-9-dodecadienyl acetate, and a minor component is (Z)-9-dodecenyl acetate. Aged dispensers from two different years emitted a much higher amount of both pheromone components than calling females. However, the summer temperature during field exposure influenced the release from mating disruption dispensers the following year. In the wind tunnel, male L. botrana were equally attracted to 12-month, field-exposed dispensers, a standard monitoring pheromone lure, and to synthetic (E)-7,(Z)-9-dodecadienyl acetate sprayed at the rate of 0.6 -60 ng h − 1 . Field trapping tests confirmed that aged dispensers from both years were at least as attractive to L. botrana males as a standard monitoring pheromone lure . The possible contribution of previously applied dispensers to the mating disruption efficacy during following applications is discussed.

- by Antonio De Cristofaro
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- Zoology, Polyethylene, Entomologia, Sex Pheromone

The neurophysiology and antennal lobe projections of olfactory receptor neurons housed within short trichoid sensilla of female Heliothis virescens F. (Noctuidae: Lepidoptera) were investigated using a combination of cut-sensillum recording and cobaltlysine staining techniques. Behaviorally relevant odorants, including intra-and inter-sexual pheromonal compounds, plant and floral volatiles were selected for testing sensillar responses. A total of 184 sensilla were categorized into 25 possible sensillar types based on odor responses and sensitivity. Sensilla exhibited both narrow (responding to few odors) and broad (responding to many odors) response spectra. Sixty-six percent of the sensilla identified were stimulated by conspecific odors; in particular, major components of the male H. virescens hairpencil pheromone (hexadecanyl acetate and octadecanyl acetate) and a minor component of the female sex pheromone, (Z)-9-tetradecenal. Following characterization of the responses, olfactory receptor neurons within individual sensilla were stained with cobalt lysine (N=39) and traced to individual glomeruli in the antennal lobe. Olfactory receptor neurons with specific responses to (Z)-9-tetradecenal, a female H. virescens sex pheromone component, projected to the female-specific central large female glomerulus (cLFG) and other glomeruli. Terminal arborizations from sensillar types containing olfactory receptor neurons sensi-tive to male hairpencil components and plant volatiles were also localized to distinct glomerular locations. This information provides insight into the representation of behaviorally relevant odorants in the female moth olfactory system.

- by N. Hillier and +1
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- Comparative Physiology, Lepidoptera, Biological Sciences, Smell

Upon contacting the cuticle of a sexually mature female, a male German cockroach exhibits a characteristic courtship behavior: he turns away from the female and raises his wings, thereby exposing tergal glands. The glandular secretion stimulates the female to mount the male and feed, thus positioning her appropriately for copulation. A multicomponent contact sex pheromone produced by females is responsible for eliciting courtship behavior. The most abundant pheromone components are 3,11-dimethylnonacosan-2one and 3,11-dimethylheptacosan-2-one, oxidation products of the abundant hydrocarbon analogs 3,11-dimethylnonacosane and 3,11-dimethylheptacosane, respectively. The C 29 -dimethyl ketone is thought to be further metabolized to two less abundant pheromone components, 29-hydroxy-3,11-dimethylnonacosan-2-one and 29-oxo-3,11-dimethylnonacosan-2-one. Based on this proposed biosynthetic pathway of pheromone production, we hypothesized that 3,11-dimethylheptacosan-2-one also would be oxidized to give two candidate pheromone components, 27-hydroxy-3,11-dimethylheptacosan-2-one, and 27-oxo-3,11-dimethylheptacosan-2-one. By using bioassay-guided fractionation and chemical analyses of cuticular extracts of virgin females and synthesis of the (3S,11S)-isomer of each of the two predicted pheromone components, we showed that the epicuticle of the German cockroach does indeed contain these two compounds. The contact sex pheromone of the female German cockroach, thus may consist of at least six biosynthetically related components.

Plant-insect interactions are not just influenced by interactions between plants and the actively feeding stages, but also by the close relationships between plants and insect eggs. Here, we review both effects of plants on insect eggs and, vice versa, effects of eggs on plants. We consider the influence of plants on the production of insect eggs and address the role of phytochemicals for the biosynthesis and release of insect sex pheromones, as well as for insect fecundity. Effects of plants on insect oviposition by contact and olfactory plant cues are summarised. In addition, we consider how the leaf boundary layer influences both insect egg deposition behaviour and development of the embryo inside the egg. The effects of eggs on plants involve egg-induced changes of photosynthetic activity and of the plant's secondary metabolism. Except for gall-inducing insects, egg-induced changes of phytochemistry were so far found to be detrimental to the eggs. Egg deposition can induce h...

- by Torsten Meiners
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- Animal Behavior, Phytochemistry, Photosynthesis, Surface Chemistry

Headspace volatiles of virgin female grape mealybugs contained a single compound that elicitited responses from antennae of males in GC-electroantennogram analyses. The structure, identified as (R * ,R * )-trans-(3,4,5,5-tetramethylcyclopent-2-en-1yl)methyl 2-methylpropanoate, an irregular, non-head-to-tail monoterpenoid, was confirmed by synthesis.

- by Kent Daane
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- Organic Chemistry, Sex Pheromone

Lepidopteran insects use sex pheromones to communicate for mating. Olfactory communication and mate-finding can be prevented by permeating the atmosphere with synthetic pheromone. Pheromonemediated mating disruption has become a commercially viable pest management technique and is used to control the codling moth, Cydia pomonella, a key insect pest of apple, on 160,000 ha worldwide. The codling moth sex pheromone, codlemone, is species specific and nontoxic. Orchard treatments with up to 100 grams of synthetic codlemone per hectare effectively control codling moth populations over the entire growing season. Practical implementation of the mating disruption technique has been realized at an opportune time, as codling moth has become resistant to many insecticides. We review codling moth chemical ecology and factors underlying the behavioral mechanisms and practical implementation of mating disruption. Area-wide programs are the result of collaborative efforts between academic research institutions, extension, chemical industries, and grower organizations, and they demonstrate the environmental and economic relevance of pheromone research. 503 Annu. Rev. Entomol. 2008.53:503-522. Downloaded from arjournals.annualreviews.org by 206.59.51.58 on 12/12/07. For personal use only. Pheromone: chemical signal produced and released by an organism, eliciting a behavioral response when perceived by a member of the same species Pheromone dispenser: device for controlled release of synthetic pheromone

- by Peter Witzgall and +1
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- Zoology, Entomology, Pest Management, Chemical Ecology

Male zebrafish, Brachydanio rerio, have paired testes and no additional reproduction glands. Incubation experiments with 3H-labeled steroid precursors showed the capacity of testes to synthesize seven steroid glucuronides. Enzyme histochemical studies demonstrated interstitial (Leydig) cells as steroid and steroid glucuronide producing sites. Male holding water, testis homogenates, and testis fractions containing steroid glucuronides were able to induce ovulation in female zebrafish. Deglucuronidation of these fractions led to a loss of ovulation inducing potency, indicating steroid glucuronides as ovulation inducers. The chemical substances are perceived by the recipients by means of olfaction, as anosmic females do not have a n ovulatory response after administration of male holding water. In African catfish, Clarias gariepinus, the male reproductive organ system consists of two paired structures, the testis and the seminal vesicle. Histochemical enzyme investigations pointed to interstitial cells as sites of steroid and steroid glucuronide production both in testis and seminal vesicle. Glucuronidation of steroids may also take place in the epithelium lining and seminal vesicle tubules. Biochemical studies showed the seminal vesicle as the main source of steroid glucuronides. Eight conjugated steroids were identified. Electrophysiological studies demonstrated that these compounds, especially 5P-pregnane-3a,l7au-dio1-20-oneglucuronide are olfactory stimulants in female conspecifics. Males with enlarged seminal vesicles, caused by compensatory growth after castration, were more attractive to ovulated female catfish in a two-choice test, using a U-shaped tank. Males lacking seminal vesicles were less attractive. The steroid glucuronide fraction of seminal vesicle fluid appeared to be responsible for the attraction effect. A synthetic mixture of steroid glucuronides resulted in a dose dependent attraction effect. The data are indicative of a pheromonal function for steroid glucuronides that are produced by the reproductive organ system of male zebrafish and African catfish.

- by R. Van Den Hurk
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- Evolutionary Biology, Genetics, Zoology, Male Reproduction Health

In order to test whether the electroantennogram (EAG) response spectrum of an insect correlates to its degree of host specificity, we recorded EAG responses of two parasitoid species with different degrees of host specificity, Microplitis croceipes (specialist) and Cotesia marginiventris (generalist), to a wide array of odor stimuli including compounds representing green leaf volatiles (GLVs), herbivore-induced plant volatiles (HIPV), ecologically irrelevant (not used by the parasitoid species and their hosts for host location) plant volatiles, and host-specific odor stimuli (host sex pheromones, and extracts of host caterpillar body and frass). We also tested the EAG responses of female moths of the caterpillar hosts of the parasitoids, Heliothis virescens and Spodoptera exigua, to some of the odor stimuli. We hypothesized that the specialist parasitoid will have a narrower EAG response spectrum than the generalist, and that the two lepidopteran species, which are similar in their host plant use, will show similar EAG response spectra to plant volatiles. As predicted, the specialist parasitoid showed greater EAG responses than the generalist to host-specific odor and one HIPV (cis-3-hexenyl butyrate), whereas the generalist showed relatively greater EAG responses to the GLVs and unrelated plant volatiles. We detected no differences in the EAG responses of H. virescens and S. exigua to any of the tested odor.

- by Henry Fadamiro
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- Physiology, Zoology, Electrophysiology, Insect Physiology

The neotropical stink bugs, Euschistus heros, Piezodorus guildinii and Edessa meditabunda, are important pests of soybean and other crops throughout Central America and in South America from Northern Argentina to Brazil. Mate finding and host plant location in these species depend largely on their chemical communication, and semiochemicals are important mediators of these behaviors. In this study scanning electron microscopy was used to examine the external morphology, distribution and abundance of antennal sensilla on males, females and 5th instar nymphs of these species. Nine morphologically different sensilla types were found: trichod sensilla, type 1 and 2 (ST1 and ST2), long and short basiconic sensilla (SB1, SB2, and SB3), slit-tipped and knob-shaped basiconic sensilla, long chaetic sensilla (Sch) and coeloconic sensilla (Sco). Differences were detected in the abundance and arrangement of the sensilla over the antennal segments in individuals of the same species and among the species studied. The Sch, Sco and the slit-tipped and knob-shaped basiconic sensilla accounted for the major difference in sensilla types among the species. The ST1 was the most abundant type and was restricted to the flagellum. The pedicel of E. heros differs from the pedicels of P. guildinii and E. meditabunda mainly by the absence of Sch. There was a sexual dimorphism in ST1, SB1 and SB2, and this may be an indicative of their roles in detection of male-produced sex pheromone and odors derived from the host plants. The SB2 was lacking in the antennal tip of both sexes and 5th instar nymphs, but was abundant on the second flagellar segment of females of the three species. The same types of sensilla were found on 5th instar nymphs, but always in significantly lower numbers. The morphology and putative functions of each sensilla were compared and discussed. ß

Experiments were conducted to test a mating disruption program for the mealybug Planococcus ficus (Signoret) (Hemiptera: Pseudococcidae) in California vineyards. The sprayable, microencapsulated formulation of the racemic sex pheromone lavandulyl senecioate was applied with an air-blast sprayer, using three and four applications in 2003 and 2004, respectively. Mating disruption was combined with an application of buprofezin in June. Compared with a no-pheromone control, there were signiÞcantly lower season-long trap catches of adult males, season-long mealybug densities (2003 only), and crop damage in mating disruption plots. The amount of mealybug reduction and mechanisms that resulted in lower crop damage in mating disruption plots is discussed. In samples taken during the growing season (April to September), mealybug density was only 12.0 Ϯ 15.6 and 31.1 Ϯ 11.6% lower in the mating disruption plots than in control plots in 2003 and 2004, respectively. In the mating disruption treatment, mealybug egg production was signiÞcantly lower (2003 only), as were the proportion of ovisacs and crawlers produced. There was no treatment impact on percentage of parasitism. Mealybug density inßuenced treatment impact. In 2004, vines were categorized as having low, medium, or high mealybug densities during a preapplication survey. After treatment application, mealybug density was reduced by 86.3 Ϯ 6.3% on vines in the low mealybug density category, but it was unchanged on vines in the high density category. Another factor that reduced treatment impact was the relatively short effective lifetime of the sprayable formulation.

- by Kent Daane
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- Zoology, Reproduction, Population Dynamics, California
- by Coby Schal
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- Multidisciplinary, Sex Pheromone, Naturwissenschaften

Background: Moths have evolved highly successful mating systems, relying on species-specific mixtures of sex pheromone components for long-distance mate communication. Acyl-CoA desaturases are key enzymes in the biosynthesis of these compounds and to a large extent they account for the great diversity of pheromone structures in Lepidoptera. A novel desaturase gene subfamily that displays Δ11 catalytic activities has been highlighted to account for most of the unique pheromone signatures of the taxonomically advanced ditrysian species. To assess the mechanisms driving pheromone evolution, information is needed about the signalling machinery of primitive moths. The currant shoot borer, Lampronia capitella, is the sole reported primitive nonditrysian moth known to use unsaturated fatty-acid derivatives as sex-pheromone. By combining biochemical and molecular approaches we elucidated the biosynthesis paths of its main pheromone component, the (Z,Z)-9,11tetradecadien-1-ol and bring new insights into the time point of the recruitment of the key Δ11-desaturase gene subfamily in moth pheromone biosynthesis.

- by Christer Löfstedt
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- Evolutionary Biology, Genetics, Lepidoptera, Lipids

The spruce seed moth, Cydia strobilella L., is a serious pest on cones of spruce (Picea spp.) in the Holarctic region. Previous studies from different parts of its area of distribution have reported conflicting results on the composition of its sex pheromone. By gas chromatography with electroantennographic detection, coupled gas chromatography-mass spectrometry, a Y-tube olfactometer bioassay, and field trials, the sex pheromone of Swedish populations of the species was identified as (8E,10E)dodecadienyl acetate and (8E,10Z)-dodecadienyl acetate. About 0.5 pg of each pheromone component was extracted per female. The most attractive blend of EE-and EZ-isomers was about 6:4, respectively, and 0.3 µg of the blend per rubber septum was the most attractive dosage for field trapping. Monounsaturated components previously reported as sex pheromone components/attractants for C. strobilella, (E)-8-dodecenyl acetate in Canadian populations and (Z)-8dodecenol in Polish and Dutch populations, did not attract any C. strobilella in this study. Large numbers of C. jungiella Clerck were trapped by using (8E,10Z)-dodecadienyl acetate alone, whereas (Z)-8-dodecenol attracted Pammene splendidulana Guenée and P. rhediella Clerck. Keywords Sex pheromone . Cydia strobilella . Tortricidae . Lepidoptera . (8E,10E)-dodecadienyl acetate . (8E,10Z)-dodecadienyl acetate . Spruce seed orchard . Monitoring

- by Erling Jirle
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- Electrophysiology, Chemical Ecology, Biological Sciences, Environmental Sciences

The sex pheromone of Lonomia obliqua Walker (Lepidoptera: Saturniidae) was studied in the laboratory. All female calling occurred during the scotophase. Most females (70.6%) called first within 24 hr of eclosion. Calling varied with age of female, with older (5-to 6-day-old) females calling earlier in the scotophase and for longer durations than younger (0-to 1-day-old) females. The sex pheromone gland of 1-to 3-day-old virgin females was extracted during the calling peak. A Y-olfactometer bioassay showed significant attraction of males to a filter paper containing the female gland extract. Gas chromatographic-electroantennogram detection (GC-EAD) analysis of the extract indicated the presence of at least two possible pheromone components. Gas chromatographic-mass spectrometric analysis of the major GC-EAD-active peak indicated a hexadecenyl acetate; chemical derivatization indicated Δ11 unsaturation. Synthetic samples of (E)-and (Z)-11hexadecenyl acetate were obtained by coupling 10-bromo-1-decanol and 1-hexyne, utilizing lithium chemistry. The comparison of the retention time of dimethyl disulfide derivatives of the natural compound, to those of synthetic chemicals, confirmed the natural compound as (E)-11-hexadecenyl acetate. The minor component was identified as the related alcohol, (E)-11-hexadecenol. The ratio of the two components in female extract was 100:35. Preliminary tests of males in a Y-olfactometer showed that their response to a mixture of the two compounds was not significantly different from that to gland extract.

- by Bianca Ambrogi and +1
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- Chemical Ecology, Chemical, Magnetic Resonance Spectroscopy, Integrated Pest Management
- by Francis Webster
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- Animal Behavior, Mass Spectrometry, Science, Magnetic Resonance Spectroscopy

By means of electroantennographic detection and gas chromatography-mass spectrometry, the sex pheromone of Argyrotaenia sphaleropa was identified as a mixture of (Z)-11-tetradecenal, (Z)-11,13-tetradecadienal, (Z)-11-tetradecenyl acetate, and (Z)-11,13-tetradecadienyl acetate in the ratio of 1:4:10:40. Best trap catches were obtained with mixtures of (Z)-11-tetradecenal and (Z)-11,13-tetradecadienal in the ratio of 1:4 to 1:9.

- by Iris Scatoni
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- Electrophysiology, Chemical Ecology, Biological Sciences, Environmental Sciences

Enterococcus faecalis is a micro-organism that can survive extreme challenges. Its pathogenicity ranges from life-threatening diseases in compromised individuals to less severe conditions, such as infection of obturated root canals with chronic apical periodontitis. In the latter situation, the infecting organisms are partly shielded from the defense mechanisms of the body. In this article, we review the virulence factors of E. faecalis that may be related to endodontic infection and the periradicular inflammatory response. The most-cited virulence factors are aggregation substance, surface adhesins, sex pheromones, lipoteichoic acid, extracellular superoxide production, the lytic enzymes gelatinase and hyaluronidase, and the toxin cytolysin. Each of them may be associated with various stages of an endodontic infection as well as with periapical inflammation. While some products of the bacterium may be directly linked to damage of the periradicular tissues, a large part of the tissu...

- by Guven Kayaoglu
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- Dentistry, Bacteriocins, Lipopolysaccharides, Sex Pheromone

- by Athula Attygalle
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- Organic Chemistry, Magnetic Resonance Spectroscopy, Lepidoptera, Tomato

The potential for pheromone-based mating disruption of the olive pyralid moth (OPM), Euzophera pinguis, in olive groves was investigated during the second flight period in small-plot trials in 2002. The female of this species emits a blend of (9Z ,12E)-tetradecadien-1-ol and (9Z ,12E)-tetradecadienyl acetate, which were synthesized for field tests. Mating disruption efficacy in 0.8-ha trials was evaluated using two parameters: reduction of male capture in pheromone traps and reduction of infestation in infestation-prone sites. White rubber septa containing 10 mg of pheromone blend as disruptant were applied at a density of 50 septa/ha for each treatment. Mean catches of E. pinguis males in pheromone traps were greatly reduced (> 95%) in pheromone-treated plots relative to similar traps placed in control plots. In addition, significant reductions were recorded (35-40%) in the oviposition and infestation levels during pheromone treatment. The total amount of pheromone blend released from disruption dispensers during the field trials was estimated to average 5.4 mg/ha/day, over 56 days.

- by Antonio Quesada
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- Chemical Ecology, Biological Sciences, Environmental Sciences, Population Density

To test whether predator odor exposure negatively affects the behavior of prey, we exposed three groups of male house mice (Mus musculus) to the odors of cat (Felis catus) urine, rabbit (Oryctolagus cuniculus) urine and water (control), respectively, for consecutive 58 days and investigated how the treatments affected the response, aggressiveness, dominance, urinary attractiveness to females and pheromone composition of male mice. Compared to mice exposed to rabbit urine or water, those exposed to cat odor did not show any response habituation to the cat odor and became more aggressive, increased mark urine production and were more attractive to females when the latter were tested with their urine. Furthermore, gas chromatography coupled with mass spectrometry analysis revealed coincident elevations of the well-known male pheromones, E,E-a-farnesene, E-b-farnesene, R,R-dehydroexo-brevicomin or S-2-sec-butyl-dihydrothiazole. In addition, rabbit urine exposure increased urinary attractiveness to females and pheromonal levels of the males in comparison with the mice exposed to water. This could be related to olfactory enrichment of heterospecific chemosignals, suggesting that predator odors were more beneficial. In light of these anti-intuitional findings in the chemical interaction between cats and mice, we conclude that predator odor affects prey more profoundly than previously believed and that its impact may not always be negative.

- by Milos Novotny and +1
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- Zoology, Ethology, Mass Spectrometry, Negative Affect

The aim of the research was to investigate auditory processing abilities in children with reading disorders using electrophysiological and behavioral tasks.Differences in auditory processing between control, compensated (age appropriate reading skills with a history of reading disorder), and reading disordered groups were systematically investigated.The reading disorder group had significantly lower results than control and compensated reader groups for most tests in the reading and auditory processing test battery. All children with a reading disorder did not pass at least one behavioral test of auditory processing, and hence would be diagnosed clinically as having an auditory processing disorder (APD). The reading disorder group also had significantly smaller /ga/-evoked mismatch negativity (MMN) area than the control group. Compensated and control groups had similar results for the electrophysiological and behavioral auditory processing tests. Correlation analyses showed that reading fluency and accuracy and nonword scores (measured using Castle and Coltheart's word/nonword test) correlated significantly with most APD measures.The general profile of auditory processing deficits in children with reading disorder was a combination of deficits on frequency patterns (i.e. frequency pattern test) and absent or small /ga/-evoked MMN. Significant results from the correlation analyses support the co-morbidity of reading and auditory processing disorders.Children with reading disorders are likely to have auditory processing disorders.

- by Mridula Sharma and +2
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- Engineering, Physiology, Psychology, Biological Psychology

Six mealybug species have been reported as citrus pests in the Mediterranean Basin: the citrus mealybugPlanococcus citri (Risso), the citriculus mealybugPseudococcus cryptus Hempel, the longtailed mealybugPseudococcus longispinus (Targioni-Tozzetti), the citrophilus mealybugPseudococcus calceolariae (Maskell), the obscure mealybugPseudococcus viburni (Signoret) and the spherical mealybugNipaecoccus viridis (Newstead). Some of these species,e.g. N. viridis, have recently been introduced into the region and are still

- by pompeo suma and +1
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- Plant Biology, Biological Control, Sex Pheromone, Mediterranean region
- by Eraldo de Lima
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- Zoology, Spatial Analysis, Density, Lepidoptera

Analyses of the elytral hydrocarbons from male and female emerald ash borer, Agrilus planipennis Fairmaire, that were freshly emerged vs. sexually mature (>10 days old) revealed a female-specific compound, 9methyl-pentacosane (9-Me-C 25 ), only present in sexually mature females. This material was synthesized by the Wittig reaction of 2-decanone with (n-hexadecyl)-triphenylphosphonium bromide followed by catalytic reduction to yield racemic 9-Me C 25 , which matched the natural compound by gas chromatography/mass spectrometry (retention time and EI mass spectrum). In field bioassays with freeze-killed sexually mature A. planipennis females, feral males spent significantly more time in contact and attempting copulation with unwashed females than with females that had been washed in n-hexane to remove the cuticular lipids. Hexane-washed females to which 9-Me-C 25 had been reapplied elicited similar contact time and percentage of time attempting copulation as unwashed females, indicating that 9-methyl-pentacosane is a contact sex pheromone component of A. planipennis. This is the first contact sex pheromone identified in the Buprestidae.

- by Peter Silk and +1
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- Pheromones, Multidisciplinary, Organophosphorus Compounds, HYDROCARBONS
- by Bill Hansson
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- Multidisciplinary, Sex Pheromone, Naturwissenschaften

Bactrocera oleae (Rossi) (Diptera: Tephritidae, Dacinae) is an oligophagous species that feeds only on cultivated olives (Olea europaea L.) and its close relatives. Synchrony of seasonal activity patterns of B. oleae, the olive fruit ßy with its hostÕs phenology is therefore expected. The objective of this study was to monitor the male olive fruit ßy response to female sex pheromone in the Þeld. White sticky traps were deployed year round for 3 yr in an olive orchard in Oroville, CA. They were checked periodically, and ßies captured were counted and sexed. Although males were captured regularly, the numbers of females captured on pheromone traps were negligible. Food-baited traps and water-baited traps were deployed to show the presence of ßies in the Þeld. Our hypothesis that males would respond to pheromone when females were available and olive fruits were susceptible for oviposition was partially supported. There were two peaks of high male captures in pheromone traps: spring and fall. In spring, females were available and mature but few acceptable olives were available for oviposition (no new crop olives yet). In fall, females were present but many of the new crop olives were already infested. The food baited traps conÞrmed the presence of ßies in the Þeld even when very few were being captured in the pheromone-baited traps. Traps containing only water caught only two ßies showing that water alone or the trap type in itself was not attractive to ßies.

- by Frank Zalom
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- Zoology, Pheromones, California, Mating

The flower of a sexually deceptive orchid, Chiloglottis reflexa, mimics both the sex pheromone and the appearance of a female thynnine wasp (Neozeloboria nr. proxima). The flower is pollinated when visited by male wasps, who attempt mating with the flower. We have used these mimetic flowers to investigate mating behavior of the male wasps. In field choice experiments, males strongly prefer to visit flowers that are very low in the habitat, 15 cm, vs. flowers that are placed at 55 or 105 cm. These studies suggest that male precopulatory response is strongly dependent on the microlocation of the female (or female mimic). Other insect-mimicking orchids, which together attract several groups of Hymenoptera, may be useful in analogous experiments on mating behavior. Additionally, these experiments help elucidate features of the mimetic flowers, particularly stature, that act to efficiently attract potential pollinators.

- by Steven N. Handel
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- Ecology, Choice Experiment, Oecologia, Sex Pheromone

Several haloacetate analogues of (Z)-13-hexadecen-ll -ynyl acetate, the main component of the sex pheromone of the pine processionary moth Thaumetopoea pityocampa, have been found to be good inhibitors of the natural pheromone. In field tests, the fluorinated compounds exhibited higher antipheromone activity than the corresponding chlorinated analogues, the order of activity being monofluoro > difluoro > trifluoro > monochloro > dichloro > trichloroacetate. In EAG bioassays the trifluoroacetate analogue showed the highest inhibition effect among all the compounds tested. These results agree with others previously reported, and show the primary role played by the steric size of the halogen in these analogues in order to achieve a notable inhibition of the pheromone action.

- by Angel Guerrero
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- Zoology, Pesticide, Sex Pheromone, ENVIRONMENTAL SCIENCE AND MANAGEMENT

In a wind tunnel bioassay the effect of three concentrations of natural extracts of (1) Scots pine wood, Pinus syl6estris, and (2) larval frass on the behavioural response of unmated females and males of the old house borer, Hylotrupes bajulus, was tested and compared to the behavioural effects of the male-produced sex pheromone (3R)-3-hydroxy-2-hexanone. The influence on the behaviour of both sexes was found to be equally significant for the two higher concentrated hexane extracts of wood and larval frass. Therefore several synthetic monoterpenes present in the extracts and ethanol were tested at the two higher concentrations (1:100, 1:1000 vol/vol). Among the higher concentrated monoterpenoid hydrocarbons [(+)-h-pinene, ( +)-i-pinene, (+ )-limonene], only h-pinene increased the activity, orientation towards scent source and interest towards conspecifics. The tests with higher concentrated ethanol and the oxygenated monoterpenes [( − )-verbenone, (− )-trans-pinocarveol, (+ )-terpinen-4-ol, (+)-h-terpineol, (− )-myrtenol] revealed that verbenone is the most effective stimulant for the females, followed by trans-pinocarveol, terpinen-4-ol and h-terpineol. For males, terpinen-4-ol was the only mediator significantly inducing attraction and orientation towards the scent source combined with an interest in conspecifics apparent by fighting or courtship behaviour. Males did not respond to verbenone which is a main compound of larval frass. Myrtenol and ethanol were ineffective in both sexes. In fact behavioural observations suggest that the beetles were repelled by the high dose of myrtenol. Using the ten-fold lower dose of the synthetic monoterpenes (1:1000 vol/vol), all semiochemicals except myrtenol lost activity. Myrtenol, however, induced behavioural responses, like increased activity and orientation towards scent source, only at the low concentration. Based on the results, primary attraction of unmated old house borer is probably mediated by monoterpenes of coniferous wood, while secondary attraction to infested wood would occur in response to volatiles of larval frass.

- by Raghu reddy
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- Biological Sciences, CHEMICAL SCIENCES, Wind Tunnel, Sex Pheromone