Stegobiol,a new sex pheromone component of drugstore beetle (Stegobium paniceum L.)

New sex pheromone component of femaleStegobium paniceum L. was isolated and identified as 2,3-dihydro-2,3,5-trimethyI-6-(1-methyl-2-hydroxybutyl)-4H-pyran-4-one, stegobiol, by spectral data and chemical conversion from stegobinone. Relative configuration at C-2, C-3, and C-1 was determined as 2S,3R,1S by the conversion from (2S,3R,1R)-stegobinone. This new sex pheromone elicits the pheromonal response from the species.     

Female sex pheromone of the common furniture beetleAnobium punctatum (Coleoptera: Anobiidae): Extraction,identification, and bioassays

Observations and reports on the common furniture beetleAnobium punctatum suggested that, on emergence, females use a sex pheromone to attract males. GLC analysis of ovipositor extracts showed the presence of a single component, which was found to be active by EAG and coupled GLC-EAG techniques, and to attract males in both walking and flying assays. The pheromone was identified by GC-MS as 2,3-dihydro-2,3,5-trimethyl-6-(1-methyl-2-oxobutyl)-4H-pyran-4-one (stegobinone), which is the sex pheromone of another anobiid, the drugstore beetle,Stegobium paniceum. MaleA. punctatum responded equally to ovipositor extracts of either species, at both the sensory (EAG) and behavioral levels, which poses the question as to how species specificity in mate attraction is achieved.     

Identification and synthesis of female sex pheromone of Oriental beetle,Anomala orientalis (Coleoptera: Scarabaeidae)

Females of the Oriental beetle,Anomala orientalis (Waterhouse), release a sex pheromone composed of a 9:1 blend of (Z)- and (E)-7-tetradecen-2-one. The double-bond position of the pheromone was determined by DMDS derivatization and interpretation of the fragmentation patterns produced by monounsaturated ketones. In a sustained-flight tunnel, males responded by flying toward female beetles and attempting to copulate with them. Both effluvium and whole-body extracts of OB females were analyzed, and the activity was found only in the airborne extracts. Flight-tunnel bioassays also showed that a synthetic 90:10Z/E blend on a rubber septum was attractive and that the responses of males to this blend were equivalent toZ isomer alone, but much better than to the singleE isomer.     

Identification of the sex pheromone of the guernsey carpet beetle,Anthrenus sarnicus Mroczkowski (Coleoptera: Dermestidae)

It has been confirmed that adult virgin females ofAnthrenus sarnicus Mroczkowski exhibit a characteristic headstand posture that is associated with the release of a sex pheromone. Volatiles trapped on filter papers suspended above calling females were attractive to adult virgin males when tested in a two-choice target bioassay. Separate aeration extracts of males and females were analyzed by gas chromatography-mass spectrometry and showed that decanol and decyln-butyrate were released by females only. These components were present in approximately equal amounts and accounted for about 90% of the total area of the chromatogram. Decyl butyrate produced an electroantennogram response with a larger response from males than females. Behaviorally, a mixture of 10g of decanol and 10g of decyl butyrate attracted 88% of males and 10g of decyl butyrate alone attracted 82% of males in the bioassay. The role of decyl butyrate as a sex pheromone is convincing, but this is not the case for decanol.     

Evidence for a sex pheromone in the hide beetle,Dermestes maculatus (De Geer) (Coleoptera: Dermestidae)

Adults of the hide beetle,Dermestes maculatus (De Geer), were shown to have a female-produced sex pheromone which excited males. Male response was positively correlated with increasing age, but females produced a higher level of pheromone at 6–8 days of age than at younger or older ages. Extractable female pheromone and male response varied over the photophase with peak values that occurred during the latter hours. Quantitative bioassay indicated that the 50% male response level (RD₅₀) would be elicited by a pheromone exposure of 0.01 female equivalents (FE). Females extracted 24 hr after mating had a lower level of extractable pheromone than did virgin females of the same age.Mention of a proprietary product does not constitute an endorsement by the Minnesota Agricultural Experiment Station.     

Identification of female-produced sex pheromone from banded cucumber beetle,Diabrotica balteata leconte (Coleoptera: Chrysomelidae)

A sex pheromone produced by female banded cucumber beetle adults,Diabrotica balteata LeConte, was isolated from volatiles trapped on Porapak Q and identified as 6,12-dimethylpentadecan-2-one. The structure was elucidated by spectroscopic analyses and confirmed by synthesis. The synthesized racemic compound was equal to the purified natural pheromone in eliciting responses by banded cucumber beetle males to field traps. A doseresponse characteristic was demonstrated for the racemic material formulated on filter paper or rubber septa and placed in field traps. The absolute configuration at the C-6 and C-12 positions was not established.This article reports the results of research only. Mention of a proprietary product does not constitute an endorsement or the recommendation for its use by USDA.This research was initiated by Dr. P.L. Guss, deceased, Research Chemist, Northern Grain Insects Research Laboratory, ARS, USDA, Brookings, South Dakota. Dr. Guss conducted the preliminary purifications and bioassays that led to the isolation and identification of this pheromone.     

Female-produced oviposition deterrents of the cigarette beetle,Lasioderma serricorne (F.) (Coleoptera: Anobiidae)

Oviposition deterrents of the cigarette beetle,Lasioderma serricorne, were isolated from its adult body extract and found to be identical to (2S,3R,1'S)-2,3-dihydro-3,5-dimethyl-2-ethyl-6-(l-methyl-2-oxobutyl)-4H-pyran-4-one (-serricorone) and its lR-epimer (-serricorone) by spectroscopic evidence. Serricorone was previously found as one of the minor sex pheromone components of the same insect, and hence indicating bi-functional nature. The presence of two isomers in the body was proved by careful treatment. Each of them exhibited the same level of oviposition deterring activity, which was less potent than the crude body extract at an increased concentration.     

Aggregation pheromone of Australian SAP beetle,Carpophilus davidsoni (Coleoptera: Nitidulidae)

A male-produced aggregation pheromone was identified for the Australian sap beetle,Carpophilus davidsoni Dobson (Coleoptera: Nitidulidae), by bioassay-guided fractionation of volatiles collected from feeding beetles. The most abundant components were: (2E,4E,6E)-5-ethyl-3-methyl-2,4,6-nonatriene, (3E,5E,7E)-6-ethyl-4-methyl-3,5,7-decatriene, (2E,4E,6E,8E)-3,5,7-trimethyl-2,4,6,8-undecatetraene, and (2E,4E,6E,8E)-7-ethyl-3,5-dimethyl-2,4,6,8-undecatetraene. The relative abundance of these components in collections from individual males feeding on artificial diet was 100:7:9:31, respectively. Pheromone production began within several days after males were placed onto diet medium and continued for at least 20 weeks. Peak production was >3 µg total pheromone per male per day. Males in groups of 50–60 emitted less pheromone (the peak level was 0.09 µg per beetle per day), and the emissions from groups contained relatively little tetraene (proportions of the components listed above were 100:7:2:7, respectively). Three additional trienes and one additional tetraene were identified in minor amounts; the entire eight-component male-specific blend is qualitatively identical and quantitatively similar to that of the North American sibling species,C. freemani Dobson. A synthetic blend of the four major components on rubber septa, prepared to emit in the same proportions as from individual males, was highly attractive in the field when synergized with fermenting whole-wheat bread dough. Cross-attraction was observed in the field involving the pheromones ofC. davidsoni, C. hemipterus (L.), andC. mutilatus Erichson. Potential uses of the pheromones in pest management are discussed.Names are necessary to report factually on available data; however, the USDA neither guarantees nor warrants the standards of the products, and the use of the names by USDA implies no approval of the products to the exclusion of others that may also be suitable.     

Sex pheromone communication in the odd beetle,Thylodrias contractes motschulsky (Coleoptera: Dermestidae)

Adult virgin females of the odd beetle,Thylodrias contractus, produce a volatile sex pheromone that influences the behavior of conspecific males and attracts them in laboratory olfactometer tests. The active substance can be collected by allowing virgin females to walk on absorbent paper disks. Disks exposed to mated females do not elicit a response from males. The male odd beetle repeatedly rubs the antennae, head, and thorax of a female with a setate glandular area on his second abdominal sternum during courtship, probably secreting a reciprocally active aphrodisiac substance.Journal Paper No. J-10248 of the Iowa Agriculture and Home Economics Experiment Station, Ames, IA 50011. Project No. 2259.     

Evidence of an aggregation pheromone in the flea beetle,Phyllotreta Cruciferae (Goeze) (Coleoptera: Chrysomelidae)

Laboratory olfactometer bioassays and field trapping experiments showed that the flea beetle,Phyllotreta cruciferae (Goeze), was highly attracted by oilseed rape(Brassica napus L.) when flea beetles were on the plant. This attraction was mediated by a flea beetle-produced aggregation pheromone based upon: (1) Oilseed rape damaged mechanically, or byP. cruciferae, or by diamondback moth,Plutella xylostella (L.), did not attractP. cruciferae. (2) Contact with the plants or feeding was required for the production of aggregation pheromone because oilseed rape alone was not attractive when separated from flea beetles by a screen. (3) Equal numbers of males and females were attracted.     

Sexually dimorphic setiferous sex patch in the male red flour beetle,Tribolium castaneum (Herbst) (Coleoptera: Tenebrionidae): Site of aggregation pheromone production

Evidence for the existence of a male-produced aggregation pheromone secreted from the prothoracic femoral setiferous sex patch ofTribolium castaneum is reported. Both sexes were attracted toca. 60 ng of crude secretion. Males and females perceive the pheromone on the day of emergence while perception differs between the sexes: male response reaches a maximum on day 1 posteclosion, when tested at <1, 1, and 30 days; females show a maximum response at 30 days posteclosion. Behavioral responses to pheromone odors and a complex Chromatographic profile are reported.Supported in part by a Graduate Student Alumni Research Award from the Graduate School, The Ohio State University; the National Science Foundation; and the College of Agriculture and Life Sciences, University of Wisconsin, Madison, Wisconsin.Dedicated to Dr. Alexander Sokoloff for his monumental contributions to the studies onTribolium and upon the occasion of his 60th birthday.     

Identification and field evaluation ofAnomala octiescostata (Coleoptera: Scarabaeidae) sex pheromone

Using GC-EAD, the sex pheromone of the scarab beetleAnomala octiescostata was identified to be a 8:2 binary mixture of (R,Z)-5-(–)-(oct-1-enyl)oxacyclopentan-2-one and (R,Z)-5-(–)-(dec-1-enyl)oxacyclopentan-2-one. These semiochemicals have been also reported as sex pheromone constituents of otherAnomala species, either geographically or seasonally isolated fromA. octiescostata. Synthetic sex pheromone was highly attractive in the field; 0.1 mg captured significantly more males than two virgin females. Buried traps were significantly more attractive than those positioned at 30, 90, and 150 cm above the ground. In a dose-response test (0.1–100 mg), no saturation due to overdose of pheromone was observed, but in most cases, two dosages differing by 10-fold were not significantly different. Response of males to traps baited with different ratios of the two components was tested in two experiments with randomized blocks and Latin-square designs. Deviation from the natural ratio (8:2) of sex pheromone did not significantly diminish the response of males. Peak flight activity of beetle was recorded at 9:00–10:00 AM JST on sunny days in the end of April 1993.Presented in part at the 10th Annual ISCE Meeting, July 31–August 4, 1993, Clearwater Beach, Florida.     

Porapak-Q collection of pheromone components and isolation of (Z)- and (E)-14-methyl-8-hexadecenal,sex pheromone components,from the females of four species ofTrogoderma (Coleoptera: Dermestidae)

A major sex pheromone component of each of fourTrogoderma species was isolated by aeration of the female beetles and absorption of the volatiles on Porapak-Q. (Z)-14-Methyl-8-hexadecenal was identified as the major component inT. inclusum andT. variabile, and (E)-14-methyl-8-hexadecenal was identified inT. glabrum. Both (Z)- and (E)-14-methyl-8-hexadecenal were found inT. granarium (Khapra beetle), in the ratio 92Z8E. In laboratory bioassays, male beetles exhibited arousal and mating responses to the aldehydes, and could discriminate between the geometric isomers. The daily production of the aldehyde was calculated for each species, and other active components were detected. These aeration-absorption studies contrast with earlier studies on macerated beetles, in which the aldehyde was not detected. The efficacy of the aeration-absorption system for collection of the sex pheromones is also described. The absorbent (Porapak-Q) efficiently collected the active pheromone; only minor amounts of activity were left in the other parts of the system.     

Identification and bioassay of sex pheromone components of carob moth,Ectomyelois ceratoniae (Zeller)

Three sex pheromone components of the carob moth were isolated and identified from the extract of female pheromone glands, using a variety of techniques including coupled gas chromatographic-electroantennographic recordings, coupled gas chromatographic-mass spectrometric analysis, microozonolysis, electroantennographic assays of monounsaturated standards, wind-tunnel bioassays, and field trials. The major component was identified as (Z,E)-9,11,13-tetradecatrienal, a novel lepidopterous pheromone component structure. Two minor components, either one of which improves the upwind flight response of males when blended with the major component, were identified as (Z,E)-9,11-tetradecadienal, and (Z)-9-tetra-decenal.     

Field evaluation ofAnomala schonfeldti ohaus (Coleoptera: Scarabaeidae) synthetic sex pheromone

Synthetic 2-(E)-nonenol, previously identified as the sex pheromone ofAnomala schonfeldti (Coleoptera: Scarabaeidae), is demonstrated to be very attractive to males in the field. Nevertheless, no significant differences were found between treatments with 1, 5, 10, and 20 mg dosages. Males ofA. schonfeldti were more significantly attracted to traps at 30 cm high than at 90 cm. Although the observed behavior seemed to indicate a trend of more attraction to buried traps than those placed at 30 cm, there was no statistical difference between the two treatments. Pheromone-baited traps caught significantly more beetles than traps containing three virgin females. Over 70% of released beetles were recaptured in six traps surrounding the point of release and separated from each other by 50 m, suggesting a possible use of the pheromone (in combination with floral compounds) in mass trapping.     

Reproductive biology of the yellow-spotted longicorn beetle,Psacothea hilaris (pascoe) (Coleoptera: Cerambycidae). III. Identification of contact sex pheromone on female body surface

A major component of female contact sex pheromone of the yellow-spotted longicorn beetle,Psacothea hilaris (Pascoe), was isolated from the elytra and identified as (Z)-21-methyl-8-pentatriacontene. The synthetic compound released the typical mating behavior including holding, mounting, and abdominal bending in males, although its activity was considerably lower than the extract of female elytra when treated on a gelatin capsule as an artificial female model.To whom correspondence should be addressed. Midori Fukaya is a postdoctoral fellow of the Research Development Corporation of Japan.     

Sex pheromone components and calling behavior of the female dermestid beetle,Trogoderma variabile Ballion (Coleoptera: Dermestidae)

Females of the dermestid beetle,Trogoderma variabile Ballion, exhibit a diel pattern of calling behavior. A potent sexual excitant and attractant for the male beetles can be collected on Porapak Q during aeration of female beetles, but cannot be detected in extracts of macerated females. The attractant has been identified as (Z)-14-methyl-8-hexadecenal. Of the five additional compounds previously identified as attractants in otherTrogoderma species, only two were found; (Z)-14-methyl-8-hexadecen-1-ol is present in extracts of macerated female beetles, but not in extracts of Porapak Q, and -caprolactone is present in extracts of Porapak Q. Three collection procedures were necessary to ensure that all the pheromone components had been isolated. Synthetic (Z)-14-methyl-8-hexadecenal elicits attraction and sexual arousal inT. Variabile males.Mention of a commercial or proprietary product in this paper does not constitute an endorsement of that product by the USDA.     

Seducin,male sex pheromone of the cockroachNauphoeta cinerea: Isolation,identification, and bioassay

The male sex pheromone of the cockroachNauphoeta cinerea was isolated from adult sternal glands and identified by gas chromatography-mass spectrometry. This pheromone, which attracts females from a distance, is a multicomponent blend. It is composed principally of three compounds: 3-hydroxy-2-butanone (acetoin), 2-methylthiazolidine, and 4-ethyl-2-meth-oxyphenol. A mixture of synthetic compounds in a ratio of 441 (2700 ng) elicits maximal response and short latency of response by receptive females, similar to that induced by male sternal gland extracts. Tested separately, each compound induces a positive response, but the moving times spent by females are generally longer than with the mixture or extracts. These three volatile compounds also are found in small amounts (about 1/40 of sternal glands) in tergal gland secretions licked by females. Acetoin also is found in the sternal and tergal glands of two closely related speciesLeucophaea maderae andHenschoutedenia flexivitta. The biological relationship of each compound and pheromone blend to behavioral response is discussed.     

Japanese beetle (Coleoptera: Scarabaeidae)

A combination of the synthetic sex attractant (R,Z)-5-(1-decenyl) dihydro-2(3H)-furanone with a 37 mixture of phenethyl propionate (PEP) and eugenol (4-allyl-2-methoxphenol) caught significantly morePopillia japonica Newman than either the sex attractant or the mixture did alone. Also, the synthetic sex attractant captured significantly more males than the PEP-eugenol did during the period of heavy adult emergence of the beetles. The two lures were not significantly different in their attractancy to males about a week later and thereafter. A combination of PEP-eugenol and virgin females in the same trap late in the season also significantly increased beetle captures.In cooperation with the Ohio Agricultural Research and Development Center, Wooster, Ohio 44691. Approved for publication as Journal Article No. 182-77.Mention of a proprietary product does not constitute an endorsement by the USDA.     

Synthesis of the sex pheromone of the Japanese beetle

The stereospecific synthesis of the sex pheromone produced by the female Japanese beetle (Popillia japonica Newman), (R,Z)-5-1-decenyl)-dihydro-2(3H)-furanone, is described. The pure syntheticR,Z form is a powerful attractant for males of the species in field bioassays and was competitive in attractiveness with live females, whereas the racemicZ isomer and theS,Z enantiomer were strong inhibitors of male response. The saturated analogs of both enantiomers were also synthesized stereospecifically.Mention of a commercial or proprietary product in this paper does not constitute an endorsement of that product by the USDA.