Aggregation pheromone ofCarpophilus dimidiatus (F.) (Coleoptera: Nitidulidae) and responses toCarpophilus pheromones in South Carolina

The major component of the male-produced aggregation pheromone ofCarpophilus dimidiatus (F.) is (3E, 5E, 7E, 9E)-6,8-diethyl-4-methyl-3,5,7,9-dodecatetraene. It attracts beetles of both sexes in the field and is synergized by odors from fermenting bread dough; mean trap catches for the tetraene alone, tetraene plus dough, dough alone, and control were 24.5, 48.3, 0.02, and 0.00, respectively. In the laboratory, individual males produced 0.58 µg±0.35 µg (SD) of the tetraene per day, but males in groups of 10–50 produced <2% as much per beetle. A second male-specific compound, (3E, 5E, 7E, 9E)-5,7-diethyl-9-methyl-3,5,7,9-tridecatetraene, was also identified fromC. dimidiatus and is about 5% as abundant as the major pheromone component.Carpophilus flight activity was monitored for one year in South Carolina corn fields with the pheromones forC. dimidiatus, C. freemani Dobson,C. mutilatus Erichson,C. hemipterus (L.),C. lugubris Murray, andC. obsoletus Erichson, all in combination with bread dough. The first four of these species accounted for 18, 70, 5.7, and 0.03%, respectively, of the totalCarpophilus trapped, but noC. lugubris orC. obsoletus were captured. Captures ofC. freemani were as high as 11,400/trap/week. Species specificity for the first four pheromones was high, except that a synthetic impurity in theC. dimidiatus pheromone was somewhat attractive toC. freemani andC. mutilatus. Three other species captured.C. antiques Melsheimer,C. marginellus Motschulsky, andC. humeralis (F.), accounted for 0.005, 5.0, and 1.3% of the total catch, respectively.C. antiquus was attracted primarily to the pheromone ofC. dimidiatus, butC. marginellus andC. humeralis responded to most of the test pheromones. There were two major periods ofCarpophilus flight activity: February through June and September through November.Names are necessary to report factually on available data; however, the USDA neither guarantees nor warrants the standard of the product, and the use of the names by USDA implies no approval of the product to the exclusion of others that may also be suitable.     

Male-produced aggregation pheromone ofCarpophilus obsoletus (Coleoptera: Nitidulidae)

Males ofCarpophilus obsoletus Erichson produce an aggregation pheromone to which both sexes respond. The pheromone was identified by GC-MS as (2E,4E,6E,8E)-3,5,7-trimethyl-2,4,6,8-undecatetraene (1), which is also a minor constituent of the pheromone blends ofC. hemipterus (L.),C. freemani Dobson, andC. lugubris Murray. The pheromone was synergized in wind-tunnel bioassays by propyl acetate, a host-type coattractant. In a dose-response study, 50 pg of1, plus propyl acetate, was significantly more attractive than just propyl acetate. Pheromone emission from groups of 65 males, feeding on artificial diet, averaged 2.2 ng/male/day. Emissions from individual males were larger, averaging 72 ng/day and ranging as high as 388 ng/day. Synthetic1 was tested in a date garden in southern California (500 µg/rubber septum), using fermenting whole-wheat bread dough as the coattractant. The pheromone plus dough attracted significantly more beetles than dough alone (means were 4.2 and 0.0 beetles per week per trap). Captured beetles were 54% females. Field trap catches were highest during the months of July and August.All programs and services of the U.S. Department of Agriculture are offered on a nondiscriminatory basis without regard to race, color, national origin, religion, sex, age, marital status, or handicap. Mention of firm names or trade products does not imply endorsement by the U.S. Department of Agriculture over similar firms or products not mentioned.     

Male-produced aggregation pheromone ofCarpophilus mutilatus (Coleoptera: Nitidulidae)

Males ofCarpophilus mutilatus Erichson produce an aggregation pheromone to which both sexes respond. The pheromone includes two hydrocarbon components, (3E,5E,7E)-5-ethyl-7-methyl-3,5,7-undecatriene (1) and (3E,5E,7E)-6-ethyl-4-methyl-3,5,7-decatriene (2). These were emitted in a 101 ratio and in a total amount of ca. 5 ng per feeding male per day. All tested doses of1 and2, from 0.03 to 30 ng, were more attractive than controls in wind-tunnel tests, but there was no evidence of synergism between these trienes. Dramatic synergism between the pheromone and a food-type coattractant occurred in the field, however. In a date garden in southern California, traps with a combination of synthetic1 and fermenting whole-wheat bread dough attracted 22 times more beetles than dough by itself and 295 times more than1 by itself. Volatile collections from males also contained three oxygenated compounds that were absent from females. One of these was tetradecanal (ca. 5 ng per male per day), but the structures of the other two are presently undetermined (0.8 and 1.1 ng per male per day). No function for these was demonstrated. One compound originating in the artificial diet, 2-phenylethanol, was particularly attractive in the wind-tunnel bioassay, as was the chromatographic solvent, methanol.     

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.     

Semiochemical-mediated flight responses of sap beetle vectors of oak wilt,Ceratocystis fagacearum

The sap beetle, Colopterus truncatus (Coleoptera: Nitidulidae), is one of the primary vectors of the oak wilt pathogen, Ceratocystis fagacearum, in the north-central United States. Field behavioral assays utilizing various release rates and blends of three methyl-branched hydrocarbon aggregation pheromone components showed that flight responses of this beetle were similar in Illinois and Minnesota populations. In both locations, both sexes of the beetle responded synergistically to a combination of the three-component pheromone and fermenting whole-wheat bread dough. Further, Colopterus truncatus preferred a high release rate over a low release rate of the three-component blend. In both locations, the response of C. truncatus to a simplified version of the pheromone consisting of (2E,4E,6E)-3,5-dimethyl-2,4,6-octatriene (1) and (2E,4E,6E,8E)-3,5,7-trimethyl-2,4,6,8-decatetraene (3) was not significantly different from the response to the three-component blend. An experiment in Illinois with all possible combinations of the components demonstrated that the decatetraene (3) was the crucial component in the blend; of all treatments, the maximal response was elicited by 3 + dough. Chipped bark, phloem, and xylem from northern pin oak, Quercus ellipsoidalis, was not attractive to C. truncatus in Minnesota. During a weekly survey over two seasons in Minnesota, C. truncatus flew in response to the three-component pheromone between early April and early July, with the maximum responses coming on May 4, 2000 and April 20, 2001. During both years, more than 98% of the beetles were trapped between April 14 and June 1. During the same survey, Glischrochilus spp. (Nitidulidae) flew during longer periods of the summer, particularly in 2001. The sex ratio of C. truncatus responding during all experiments was female-biased (1.8:1, female–male), which is characteristic of other male-produced coleopteran aggregation pheromones. Other sap beetles that play a minor role in the pathobiology of C. fagacearum also responded in experiments conducted in Minnesota. Carpophilus brachypterus Say was cross-attracted to the two- and three-component blends of the C. truncatus pheromone and dough, whereas two Glischrochilus spp. were attracted to all treatments that contained dough.     

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.     

Male-produced Aggregation Pheromone of Colopterus truncatus: Structure, Electrophysiological, and Behavioral Activity

A male-produced aggregation pheromone was demonstrated in Colopterus truncatus Randall (Coleoptera: Nitidulidae) by gas chromatographic comparisons of male and female volatile emissions. Male-specific compounds were identified with coupled gas chromatographic–mass spectrometric (GC-MS) analysis and GC and MS comparison of authentic standards. Physiological activity was evaluated by coupled gas chromatographic–electroantennographic (GC-EAG) recordings, and electroantennographic (EAG) assays of standards. The male-produced volatiles eliciting responses from male and female antennae (and relative abundance) were (2E,4E,6E)-3,5-dimethyl2,4,6-octatriene (1) (1.8), (2E,4E,6E)-4,6-dimethyl-2,4,6-nonatriene (2) (100), and (2E,4E,6E,8E)-3,5,7-trimethyl-2,4,6,8-decatetraene (3) (3.3). A fourth male-specific compound, (2E,4E,6E,8E)-4,6,8-trimethyl-2,4,6,8-undecatetraene (4) (0.6) was not EAG-active. EAG dose–response studies showed that the antennae were most sensitive to 2 followed by 3 and 1. Synthetic 2, binary blends of 1 and 3, and tertiary blends of 1, 2, and 3 were highly attractive in the field when synergized with fermenting whole-wheat bread dough. In the field, cross-attraction to the C. truncatus pheromone components was observed for Carpophilus lugubris Murray, C. antiquus Melsheimer, and C. brachypterus Say.     

Aggregation pheromone of square-necked grain beetle,Cathartus quadricollis (Guér.)

When feeding on rolled oats, male square-necked grain beetles,Cathartus quadricollis (Guér.), produced the aggregation pheromone (3R,6E)-7-methyl-6-nonen-3-yl acetate, for which the trival name quadrilure is proposed. The pheromone was highly attractive to both sexes in a two-choice, pitfall olfactometer modified to retain responding beetles by placing a food stimulus (an oat flake) in the glass vials containing the experimental and control stimuli. TheS enantiomer of the pheromone was inactive. Males also produced small amounts of (E)-7-methyl-6-nonen-3-one, (E)-7-methyl-6-nonen-3-ol, and (6E)-7-methyl-3-propyl-2,6-nonadienyl acetate, but these compounds were inactive in the laboratory bioassay. Segregated males and females both produced (R)-(–)-1-octen-3-ol, which by itself was repellent to both sexes but did not diminish beetle response to the aggregation pheromone.Coleoptera: Cucujidae.Research supported by the Natural Sciences and Engineering Research Council of Canada, Strategic Grant G1039 and Operating Grants A3881 and A3706.     

Sex pheromone of oriental beetle,Exomala orientalis: Identification and field evaluation

A gas chromatograph coupled with a behavioral bioassay was used to identify two sex pheromone components, 7-(Z)- and 7-(E)-tetradecen-2-one of the Oriental beetle (OB),Exomala orientalis. Field experiments showed that the blend of the two isomers (Z:E, 7:1) was not significantly more attractive than theZ component alone. The best performance of traps baited with the synthetic sex pheromone was achieved when they were set with the pheromone device at 30 cm above the ground. Catches in traps baited with 1 and 10 mg were not significantly different, but they were higher (2.9-fold) than captures in traps loaded with 0.1 mg of the pheromone. Further investigations by GC-EAD revealed the presence of a possible minor component, but the small amount of material prevented its identification. 2-(E)-Nonenol, with the same retention time as the natural product, did not affect the attractancy of the synthetic sex pheromone. GC-EAD screening of previously identified sex pheromones of scarab beetles showed that male antennae of the Oriental beetle responded to japonilure, but it showed neither synergism nor inhibition to the OB sex pheromone.     

Attraction ofCarpophilus spp. (Coleoptera: Nitidulidae) to synthetic aggregation pheromones and host-related coattractants in Australian stone fruit orchards: Beetle phenology and pheromone dose studies

Synthetic aggregation pheromones ofCarpophilus hemipterus (L.) andCarpophilus mutilatus Erichson were field tested during a 10-month period in southern New South Wales stone fruit orchards to determineCarpophilus spp. phenology and the effect of two pheromone doses on attraction. Aggregation pheromones synergize the attraction of host volatiles toCarpophilus spp. Four major species,C. hemipterus, C. mutilatus, C. davidsoni Dobson andC. (Urophorus) humeralis (F.), were trapped, with greater numbers of each species inC. hemipterus pheromone/fermenting whole-wheat breaddough-baited traps, than in dough-only-traps. InC. mutilatus pheromone/ fermenting-dough-baited traps, onlyC. mutilatus andC. davidsoni responded in greater numbers than to dough-only traps. Beetles first appeared in traps in late September (early spring) when daily maximum temperatures averaged 17.5C. Trappings reached a peak during October and declined to very low levels in November–December (late spring-early summer). Numbers trapped of all species increased during February–March (late summer–early autumn), presumably due to the presence of abundant host resources (ripening and fallen fruit), and continued at high levels until May (late autumn). An 18-week study demonstrated significantly greater responses byCarpophilus spp. to 5000-g than to 500-g doses of C.hemipterus andC. mutilatus pheromones. Greatest responses to 5000g were recorded forC. hemipterus andC. mutilatus responding to their own pheromones (increased attraction over dough alone of 259x and 21.2x respectively). Implications of the study and the potential for using synthetic aggregation pheromones for managingCarpophilus spp. populations in Australian stone fruit are discussed.     

Chemical communication in cucujid grain beetles

Males of five sympatric species of economically damaging cucujid grain beetles,Cryptolestes ferrugineus (Stephens),C. pusillus (Schönhen),C. turcicus (Grouvelle),Oryzaephilus mercator (Fauvel), andO. surinamensis (L.), produce macrolide aggregation pheromones especially in the presence of food. Work leading to the isolation, identification, and establishment of biological activity of these semiochemicals is reviewed. The trivial name cucujolide is proposed and used to identify these compounds that are characteristic of the Cucujidae. The twoOryzaephilus share species share a common cucujolide pheromone, whileCryptolestes species use cucujolides that are either enantiomeric, unique to the genus, or released in trace quantities byOryzaephilus spp. and not used as pheromones by the latter species. The major mechanisms for species specificity in chemical communication are: (1) presence of a unique pheromone (C. ferrugineus andC. pusillus); (2) use of pheromones that are inactive alone but synergize response to cucujolides unique to a species (C. pusillus, C. turcicus, andO. surinamensis); (3) response to only one enantiomer of a pheromone (C. ferrugineus, O. surinamensis, andO. mercator); and (4) synergism between enantiomers of a pheromone (C. turcicus). The only species for which cross-attraction was evident wasO. mercator toO. surinamensis. Both sexes ofOryzaephilus spp. produce (R)-1-octen-3-ol, which highly synergizes response to the cucujolide pheromones. Similar synergism occurs between hexanal, octanal, and nonanal and the cucujolide pheromones ofOryzaephilus spp. The males of a sixth cucujid species,Cathartus quadricollis (Guér) produce a different aggregation pheromone, (3R,6E)-7-methyl-6-nonen-3-yl acetate. Trapping ofCryptolestes andOryzaephilus spp. in cardboard traps baited with pheromones is efficient in environments mimicking food-storage areas. Pheromone-baited plastic probe traps are the most efficient at capturing these species in infested grain.Coleoptera: Cucujidae.Presented at the 194th American Chemical Society National Meeting in the Symposium on Insect Chemical Communication: Unifying Concepts (Burdick & Jackson International Award in Pesticide Chemistry honoring Dr. James H. Tumlinson), New Orleans, Louisiana, August 30–September 4, 1987.Research supported by the Natural Sciences and Engineering Research Council of Canada, Strategic Grant No. G1039 and Operating Grants Nos. A3881 and A3706.     

Sex pheromone blend discrimination by male moths fromE andZ strains of European corn borer

Sex pheromone behavioral responses were analyzed in a flight tunnel with European corn borer,Ostrinia nubilalis (Hübner), males from three distinct populations. Males from a bivoltine and a univoltine biotype using a 97.82.2 blend (Z strains) of (Z)- and (E)-11-tetradecenyl acetate were assayed with treatments containing 0, 0.5, 1, and 3% of theE isomer. Males from neither population oriented in the plume to the 100%Z treatment, but bivoltine males oriented and flew to the source to the other three treatments, whereas univoltine males oriented and flew to the source only to the 1 % and 3 %E treatments. Males from a bivoltine biotype using a 199 blend ofZ/E isomers (E strain) were assayed with sources containing 0, 0.5, 1, and 3% of theZ isomer. Males did not orient to the 0%Z source, but oriented and flew to the source to the other three treatments. In addition to using opposite geometric isomers for the main pheromone component, the bivoltineE strain differed from the bivoltineZ strain by producing and responding better to 1 % of the minor component and by storing 3 times more pheromone in the female glands. Contrary to previous reports, the blend of two pheromone components is significantly better than the main component alone in eliciting oriented flight and close-range behavior with males from all three populations of European corn borer.     

Semiochemicals from bark beetles: New results,remarks, and reflections

A brief survey is given about recent results in the identification of semiochemicals in bark beetles: Males ofIps sexdentatus (Boern.), stressed by the attack on resinous trees produce large amounts of 3(S)-1-methyl-5-(1-hydroxyl-1-methylethyl)-cyclohexa-1,3-diene. The compound appears to be derived from ³-carene and acts as a repellent. Males ofIps typographus (L.), stressed through the attack on unsuitable host material release 3-methyl-7-methylene-1,3(E), 8-nonatriene, which seems to act as a repellent. The odor bouquet of three species ofPityogenes is described. The occurrence of (+)-grandisol and other compounds related to weevil pheromones points to a close relation between Scolytidae and Curculionidae. Females ofDendroctonus simplex (Le Conte) use (–)-frontalin as the main pheromone. 6-Methyl-6-hepten-2-one, a minor component among the volatile compounds released by the females, is regarded as a possible precursor of frontalin. Similarly, (2R,5S)-2(1-hydroxyl-1-methylethyl)-5-methyltetrahydrofuran, pityol, a pheromone ofPityophthorus spp., is regarded to at least share a common biogenetic precursor with 6-methyl-5-hepten-2-ol, sulcatol. A new bicylic acetal, 2-ethyl-1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane, is described as an aggregation pheromone of the beech bark beetle,Taphrorychus bicolor (Herbst). Structural relationships between bark beetle pheromones and plant volatiles are discussed.     

Ancestral semiochemical attraction persists for adjoining populations of siblingIps bark beetles (Coleoptera: Scolytidae)

Three species ofIps pine bark beetles in Hopping's group IX (S.L. Wood'sgrandicollis group),Ips confusus, I. lecontei, andI. paraconfusus, are parapatrically distributed in the American Southwest. They share post-Pleistocene altitudinal ecotones with their host pines. Adjacent to these areas of host overlap, we tested the hypothesis that aggregation pheromones produced by male beetles and/or host volatiles are sufficient to elicit the speciesspecific colonization behaviors typical of these threeIps species in nature. A more distantly related species,I. pini (Hopping's group IV, S.L. Wood'spini group) was used for outgroup comparison. Under the influence of pheromone, males ofI. confusus andI. paraconfusus do not discern among unin-fested log bolts of host and nonhost pine prior to bark contact. Males responding to pheromones emanating from infested bolts are similarly undiscriminating. Females ofI. confusus andI. lecontei olfactorily discern the combination of conspecific males in host pine from other possible beetlepine combinations; females ofI. paraconfusus do not. FemaleI. pini discerned conspecific pheromone from that ofI. lecontei. The bark beetle predator,Enoclerus lecontei, is attracted by, but does not discriminate among, the male-produced volatiles of these Group IXIps species. These results support a hypothesis that divergence in pheromonal responses by these group IXIps species has evolved following their speciation, having been manifested first in the female sex. Evolutionarily, the derived pheromonal messages have preceded their behavioral discrimination by these beetles. Additional speciesspecific cues may operate between the sexes in the field that may preclude heterospecific pairings.     

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.     

Aggregation pheromone of driedfruit beetle,Carpophilus hemipterus Wind-tunnel bioassay and identification of two novel tetraene hydrocarbons

A male-produced aggregation pheromone was demonstrated inCarpophilus hemipterus (L.) (Coleoptera: Nitidulidae) using a wind-tunnel bioassay. Both sexes responded to the pheromone, but the beetles flew in the wind tunnel only after they had been starved for at least several hours. The attractiveness of the pheromone was greatly enhanced by volatiles from a food source, and combinations of pheromone and food volatiles typically attracted 3–10 times more beetles than either source by itself. A variety of food-related sources of volatiles were effective. These included apple juice; a mixture of baker's yeast plus banana; the pinto bean diet used for rearing this beetle; the chemicals propyl acetate, ethanol; and a mixture of acetaldehyde, ethyl acetate, and ethanol. The pheromonal activity resided with a series of 10 male-specific, unsaturated hydrocarbons of 13, 14, and 15 carbon atoms. These were partially separated by HPLC. No single compound was absolutely required for pheromonal activity to be observed, and various subsets of these compounds were active. The most abundant component was (2E,4E,6E,8E)-3,5,7-trimethyl-2,4,6,8-decatetraene. One minor component was (2E,4E,6E,8E)-3,5,7-trimethyl-2,4,6,8-undecatetraene. These structures were proven by synthesis. Together, the synthetic compounds were as active in the wind tunnel as the beetle-derived pheromone.     

Intra- and interspecific sex pheromone responses of screwworm and secondary screwworm flies

A laboratory behavioral assay examined intra- and interspecific responses to sex pheromone by screwworms,Cochliomyia hominivorax, and secondary screwworms,C. macellaria, in relation to the duration of colonization ofC. hominivorax test males. Females ofC. macellaria, like those ofC. hominivorax, were found to produce a pheromone that stimulates male copulatory attempts on contact. Newly colonized (<22 generations)C. hominivorax males did not respond toC. macellaria pheromone, indicating that pheromone contributes to reproductive isolation between these two closely related species. Although long-colonized (>200 generations)C. hominivorax males did respond toC. macellaria females or their extract, this behavior was infrequent and significantly less common than intraspecific responses. DeprivingC. macellaria adults of dietary protein did not affect the potency of female extracts, but did reduce male responsiveness to pheromone. These results provided little evidence that colonization reduces the ability ofC. hominivorax males to differentiate betweenC. hominivorax andC. macellaria females using sex pheromones.     

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.     

Sex pheromone components of the oblique-banded leafroller,Choristoneura rosaceana in the Okanagan Valley of British Columbia

(Z)-11-Tetradecen-1-yl acetate, (E)-11-tetradecen-1-yl acetate, and (Z)-11-tetradecen-1-ol were previously reported as the sex pheromone in New York strains of the oblique-banded leafroller,Choristoneura rosaceana (Harris), and (E)-11-tetradecen-1-ol was tentatively identified in female tip extracts. For Okanagan Valley strains ofC. rosaceana, an additional component, (Z)-11-tetradecenal, was identified from female tip extracts by split-less capillary gas-liquid chromatography and mass spectroscopy and was strongly stimulatory in electroantennogram studies. In field tests, 3 mg of 96.521.5 (Z)-11-tetradecen-1-yl acetate, (E)-11-tetradecen-1-yl acetate, and (Z)-11-tetradecen-1-ol (containing approx. 1%E isomer) was not as attractive as female-baited traps, and significant numbers of European leafrollerArchips rosanus L. were attracted. The above blend with 1% (Z)-11-tetradecenal added was significantly more attractive than traps baited with femaleC. rosaceana, butA. rosanus males were still attracted. Increased percentages of (Z)-11-tetradecenal up to 4% caused increased catches ofC. rosaceana and decreased catches ofA. rosanus. Low amounts of (E)-11-tetradecen-1-ol and (E)-11-tetradecenal male also contribute to increased specificity of the synthetic pheromone blend toC. rosaceana.Lepidoptera: Tortricidae.Contribution No. 638, Agriculture Canada, Research Station, Summerland, British Columbia, Canada.     

(Z)-11-Eicosenyl acetate,an aggregation pheromone inDrosophila malerkotliana

(Z)-11-Eicosenyl acetate (Z11–20:Ac) was identified as the aggregation pheromone inDrosophila malerkotliana. The pheromone (200–300 ng/fly) was isolated from hexane extracts of the ejaculatory bulb of sexually mature male flies. Males released very little, if any,Z11–20:Ac to the food at any time. During mating there was a transfer of ca. 100 ng ofZ11–20:Ac to the female's reproductive tract. The mated female fly transferred theZ11–20:Ac to the surrounding surfaces in just a few hours after mating. In bioassay in a wind-tunnel olfactometer,Z11–20:Ac was not attractive alone, but was synergistic with fermenting food or with acetone. AlthoughD. malerkotliana has no (Z)-11-octadecenyl acetate (Z11–18:Ac), it was as attracted toZ11–18:Ac as to an equal quantity ofZ11–20:Ac.D. melanogaster andD. simulans, however, responded to theZ11–18: Ac that they produced and did not respond toZ11–20:Ac.