Sex Pheromone and Trail Pheromone of the Sand Termite <Emphasis Type="Italic">Psammotermes hybostoma</Emphasis>

Within the complex network of chemical signals used by termites, trail pheromones and sex pheromones are among the best known. Numerous recent papers map the chemical identity and glandular origin of these pheromones in nearly all major isopteran taxa. In this study, we aimed to describe the sex pheromone and the trail pheromone of a poorly known sand termite, Psammotermes hybostoma. We identified (3Z,6Z,8E)-dodeca-3,6,8-trien-1-ol (dodecatrienol) as the sex pheromone released by tergal and sternal glands of female imagos and, at the same time, as the trail pheromone secreted from the sternal gland of workers. We conclude that chemical communication in Psammotermes does not differ from that of most other Rhinotermitidae, such as Reticulitermes, despite the presence of a diterpene as a major component of the trail pheromone of Prorhinotermes to which Psammotermes is presumed to be phylogenetically close. Our findings underline once again the conservative nature of chemical communication in termites, with dodecatrienol being a frequent component of pheromonal signals in trail following and sex attraction and, at the same time, a tight evolutionary relationship between the trail following of working castes and the sex attraction of imagos.     

(Z,Z,E)-3,6,8-Dodecatrien-1-ol, A Major Component of Trail-Following Pheromone in Two Sympatric Termite Species Reticulitermes lucifugus grassei and R. santonensis

Trail-following bioassays show that trails of the two subterranean termites, Reticulitermes lucifugus grassei and R. santonensis, which are sympatric in some areas of southwestern France, are not species specific. Even when tested just above threshold level, trails from pentane extracts of whole workers of R. santonensis are always preferred by both species. If the R. santonensis extract is progressively diluted, the preference is lost. In purified extracts of workers of R. lucifugus grassei that elicited a trail-following response, only one compound is active. It was identified by GC-MS as the same major compound of the trail-following pheromone of R. santonensis: (Z,Z,E)-3,6,8-dodecatrien-1-ol (DTE-OH). The threshold concentration of activity of synthetic DTE-OH was determined to be 10^–3 ng/cm of trail; optimal activity was obtained at 10^–2 ng/cm of trail. The increase of trail-following activity of worker extracts of R. lucifugus grassei after hydrolysis by potassium hydroxide suggests that DTE-OH also is bound to other components in sternal gland secretions. DTE-OH was also identified in alates of R. lucifugus grassei, suggesting that the compound functions both as a trail-following and a sex pheromone, as has been shown to be the case in R. santonensis. This demonstrates the high economy developed by termites in their strategies of chemical communication.     

(7<Emphasis Type="Italic">Z</Emphasis>,9<Emphasis Type="Italic">E</Emphasis>)-2-Methyl-7,9-Octadecadiene: A Sex Pheromone Component of <Emphasis Type="Italic">Lymantria Bantaizana</Emphasis>

Our objective was to identify the sex pheromone of Lymantria bantaizana (Lepidoptera: Lymantriidae) whose larvae feed exclusively on walnut, Juglans spp., in China, and Japan. Coupled gas chromatographic–electroantennographic detection (GC-EAD) analyses of pheromone gland extracts revealed a single EAD-active component. Retention index calculations of this compound on four GC columns suggested that it was a methyl-branched octadecadiene with conjugated double bonds. In GC-EAD analyses of 2-methyloctadecenes, (Z)-2-methyl-7-octadecene and (E)-2-methyl-7-octadecene elicited the strongest antennal responses, suggesting that the double bond positions were at C7 and C9. In comparative GC-EAD analyses of pheromone gland extract and stereoselectively synthesized isomers (E,E; E,Z; Z,E; Z,Z) of 2-methyl-7,9-octadecadiene, the (E,Z)- and (Z,E)-isomer had retention times identical to that of the candidate pheromone, but only the latter isomer elicited strong EAD activity. Results of field experiments in Japan substantiated that (7Z,9E)-2-methyl-7,9-octadecadiene is the L. bantaizana sex pheromone, a compound previously unknown in the Lepidoptera. Detection surveys in North America for exotic Eurasian forest defoliators could include traps baited with the L. bantaizana pheromone.     

(2<Emphasis Type="Italic">S</Emphasis>,8<Emphasis Type="Italic">Z</Emphasis>)-2-Butyroxy-8-heptadecene: Major Component of the Sex Pheromone of Chrysanthemum Gall Midge, <Emphasis Type="Italic">Rhopalomyia longicauda</Emphasis>

The sex pheromone of the chrysanthemum gall midge, Rhopalomyia longicauda (Diptera: Cecidomyiidae), the most important insect pest in commercial plantations of chrysanthemum, Dendranthema morifolium (Ramat.) Tzvel., in China, was identified, synthesized, and field-tested. Volatile chemicals from virgin females and males were collected on Porapak in China and sent to the United Kingdom for analysis. Coupled gas chromatographic–electroantennographic detection (GC-EAG) analysis of volatile collections from females revealed two compounds that elicited responses from antennae of males. These compounds were not present in collections from males. The major EAG-active compound was identified as 2-butyroxy-8-heptadecene by gas chromatographic (GC) retention indices, mass spectra, in both electron impact and chemical ionization modes, hydrogenation, epoxidation, and derivatization with dimethyldisulfide. The lesser EAG-active compound was identified as the corresponding alcohol. The ratio of butyrate to alcohol in the collections was 1:0.26. Racemic (Z)-8-heptadecen-2-ol and the corresponding butyrate ester were synthesized from (Z)-7-hexadecenyl acetate, and the synthetic compounds found to have identical GC retention indices and mass spectra to those of the natural, female-specific components. Analysis of the volatile collections on an enantioselective cyclodextrin GC column showed the natural pheromone contained (2S,8Z)-2-butyroxy-8-heptadecene. Field tests showed that rubber septa containing racemic (Z)-2-butyroxy-8-heptadecene were attractive to R. longicauda males. The (naturally occurring) S-enantiomer was equally as attractive as the racemate, while the R-enantiomer was not attractive to males, and did not inhibit the activity of the S-enantiomer. The attractiveness of the butyrate was significantly reduced by the presence of even small amounts of the corresponding alcohol.     

(<Emphasis Type="Italic">Z,Z</Emphasis>)-6,9-Heneicosadien-11-One: Major Sex Pheromone Component Of Painted Apple Moth, <Emphasis Type="Italic">Teia anartoides</Emphasis>

(Z, Z)-6,9-Heneicosadien-11-one (Z6Z9-11-one-21Hy) was identified as the major sex pheromone component of the painted apple moth (PAM), Teia anartoides (Lepidoptera: Lymantriidae), on the basis of (1) comparative gas chromatographic-electroantennographic detection (GC-EAD) analyses, GC-mass spectrometry (MS), high-performance liquid chromatography (HPLC)-MS, and HPLC-UV/visible spectroscopy of pheromone gland extracts and authentic standards; (2) GC-EAD analyses of effluvia of calling females; and (3) wind tunnel and field trapping experiments with a synthetic standard. In field experiments in Australia, synthetic Z6Z9-11-one-21Hy as a single component attracted male moths. Wind tunnel experiments suggested that a 4-component blend consisting of Z6Z9-11-one-21Hy, (6Z,9R,10S)-cis-9,10-epoxy-heneicosene (Z6-9R10S-epo-21Hy), (E, E)-7,9-heneicosadien-6,11-dione (E7E9-6,11-dione-21Hy), and 6-hydroxy-(E, E)-7,9-heneicosadien-11-one (E7E9-6-ol-11-one-21Hy) (all present in pheromone gland extracts) might induce more males to orient toward, approach, and contact the source than did Z6Z9-11-one-21Hy as a single component. Additional experiments are needed to determine conclusively whether or not Z6-9R10S-epo-21Hy, E7E9-6,11-dione-21Hy, and E7E9-6-ol-11-one-21Hy might be minor sex pheromone components of PAM. Moreover, attractiveness of synthetic pheromone and virgin PAM females needs to be compared to determine whether synthetic pheromone could replace PAM females as trap baits in the program to monitor eradication of exotic PAM in New Zealand.     

Laboratory Evaluation of <Emphasis Type="Italic">Artemisia annua</Emphasis> L. Extract and Artemisinin Activity against <Emphasis Type="Italic">Epilachna paenulata</Emphasis> and <Emphasis Type="Italic">Spodoptera eridania</Emphasis>

Ethanolic extract of aerial parts of Artemisia annua L. and artemisinin were evaluated as anti-insect products. In a feeding deterrence assay on Epilachna paenulata Germ (Coleoptera: Coccinellidae) larvae, complete feeding rejection was observed at an extract concentration of 1.5 mg/cm² on pumpkin leaf tissue. The same concentration produced a feeding inhibition of 87% in Spodoptera eridania (Cramer) (Lepidoptera: Noctuidae). In a no-choice assay, both species ate less and gained less weight when fed on leaves treated with the extract. Complete mortality in E. paenulata and 50% mortality in S. eridania were observed with extract at 1.5 mg/cm². Artemisinin exhibited a moderate antifeedant effect on E. paenulata and S. eridania at 0.03–0.375 mg/cm². However, a strong effect on survival and body weight was observed when E. paenulata larvae were forced to feed on leaves treated at 0.03 and 0.075 mg/cm². Artemisia annua ethanolic extract of aerial parts at 1.5 mg/cm² showed no phytotoxic effect on pumpkin seedlings.     

Behavioral evidence for multicomponent trail pheromone in the termite,Reticulitermes flavipes (Kollar) (Isoptera: Rhinotermitidae)

Evidence is presented for a multicomponent trail pheromone in the eastern subterranean termiteReticulitermes flavipes (Kollar). Choice tests were used to compare strength and persistency of trails made by termites in glass tubes. Tubes connected to termite nests for 24 hr were marked by termites with an extremely long-lasting chemical that persisted for at least one year, and a highly volatile substance that decayed in 15 min. Individual termites varied the trail they deposited under different circumstances. When removed from the nest and placed in a clean tube, they deposited a highly volatile substance. They left stronger and more persistent trails when exploring clean tubes attached to the nest. When they discovered a new food source, they left trails that were more attractive and far more persistent than trails made by exploring or displaced termites. A food trail made by 15 workers was still effective after 24 hr, whereas a trail made by 50 displaced workers, walking one after another through a tube, lasted only 5 min.     

Biosynthesis of (3<Emphasis Type="Italic">Z</Emphasis>,6<Emphasis Type="Italic">Z</Emphasis>,9<Emphasis Type="Italic">Z</Emphasis>)-3,6,9-Octadecatriene: The Main Component of the Pheromone Blend of <Emphasis Type="Italic">Erannis bajaria</Emphasis>

The hydrocarbons (3Z,6Z,9Z)-3,6,9-octadecatriene (3Z,6Z,9Z-18:H) and (3Z,6Z,9Z)-3,6,9-nonadecatriene (3Z,6Z,9Z-19:H) constitute the pheromone of the winter moth, Erannis bajaria. These compounds belong to a large group of lepidopteran pheromones which consist of unsaturated hydrocarbons and their corresponding oxygenated derivatives. The biosynthesis of such hydrocarbons with an odd number of carbons in the chain is well understood. In contrast, knowledge about the biosynthesis of even numbered derivatives is lacking. We investigated the biosynthesis of 3Z,6Z,9Z-18:H by applying deuterium-labeled precursors to females of E. bajaria followed by gas chromatography–mass spectrometry analysis of extracts of the pheromone gland. A mixture of deuterium-labeled [17,17,18,18-²H₄]-3Z,6Z,9Z-18:H and the unlabeled 3Z,6Z,9Z-18:H was obtained after topical application and injection of (10Z,13Z,16Z)-[2,2,3,3-²H₄]-10,13,16-nonadecatrienoic acid ([2,2,3,3-²H₄]-10Z,13Z,16Z-19:acid) or (11Z,14Z,17Z)-[3,3,4,4-²H₄]-11,14,17-icosatrienoic acid ([3,3,4,4-²H₄]-11Z,14Z,17Z-20:acid). These results are consistent with a biosynthetic pathway that starts with α-linolenic acid (9Z,12Z,15Z-18:acid). Chain elongation leads to 11Z,14Z,17Z-20:acid, which is shortened by α-oxidation as the key step to yield 10Z,13Z,16Z-19:acid. This acid can be finally reduced to an aldehyde and decarbonylated or decarboxylated to furnish the pheromone component 3Z,6Z,9Z-18:H. A similar transformation of 11Z,14Z,17Z-20:acid yields the second pheromone component, 3Z,6Z,9Z-19:H.     

Sex Pheromones of Two Melittini Species, <Emphasis Type="Italic">Macroscelesia Japona</Emphasis> and <Emphasis Type="Italic">M. Longipes</Emphasis>: Identification and Field Attraction

Two Melittini species, Macroscelesia japona and M. longipes (Lepidoptera: Sesiidae), are native to Japan, but occupy different localities as their host plants seldom grow together. The contents of the sex pheromone gland of adult females of both species, obtained after rearing larvae collected from the field, were investigated by gas chromatograph-electroantennogram detection (GC-EAD) and gas chromatograph-mass spectrometry (GC-MS) analyses. Two GC-EAD-active components were found in a crude extract of M. japona female pheromone gland, and identified as (2E,13Z)-2,13-octadecadien-1-ol (E2,Z13-18:OH) and (2E,13Z)-2,13-octadecadienal (E2,Z13-18:Ald). The average ratio of these two components was about 1:10. In the field, M. japona males were attracted to traps baited with E2,Z13-18:Ald alone, but the strongest attraction was observed with a 1:100 mixture of E2,Z13-18:OH and E2,Z13-18:Ald. The same two components were found in extracts of M. longipes females, but in a markedly different ratio. Male M. longipes were attracted most strongly to lures containing a 20:1 mixture of E2,Z13-18:OH and E2,Z13-18:Ald, although some males were also attracted to lures with E2,Z13-18:OH alone. Although the two species do not generally occur in sympatry, our data indicate that, in the event of overlap, cross attraction of the two species is unlikely.     

Sex Pheromone of the Saturniid Moth, <Emphasis Type="Italic">Hemileuca burnsi</Emphasis>, from the Western Mojave Desert of California

The sex pheromone blend of Hemileuca burnsi (Lepidoptera: Saturniidae) from the western Mojave Desert was determined to be a combination of (10E,12Z)-hexadecadien-1-yl acetate (E10,Z12-16:Ac), (10E,12Z)-hexadecadien-1-ol (E10,Z12-16:OH), (10E,12E)-hexadecadien-1-yl acetate (E10,E12-16:Ac), and hexadecyl acetate (16:Ac). (10E,12Z)-Hexadecadienal (E10,Z12-16:Ald) was tentatively identified in pheromone gland extracts based on electroantennographic responses and, when added to the above blend, it enhanced trap captures at low doses. The mean ratio of the compounds in extracts of pheromone glands was 100:23:232:14:0.4 (E10,Z12-16:Ac: E10,E12-16:Ac: 16:Ac: E10,Z12-16:OH: E10,Z12-16:Ald). Field trials indicated that although E10,Z12-16:Ac and E10,Z12-16:OH were essential for attraction, the two-component blend was not attractive by itself. Addition of the three other compounds was necessary for maximum attraction, rendering this the most complicated pheromone blend described for a Hemileuca species to date. Similarities between the sex pheromone of H. burnsi and that of the allopatric Hemileuca electra electra and differences between the blends of H. burnsi and that of the sympatric H. electra mojavensis support a case for reproductive character displacement in the pheromone communication channel of H. electra.     

Sex Attractant Pheromone from the Neotropical Red-Shouldered Stink Bug, <Emphasis Type="Italic">Thyanta perditor</Emphasis> (F.)

Olfactometer bioassays showed that odors from mature Thyanta perditor males attracted females but not males. Furthermore, odors from females did not attract either sex, indicating that like other phytophagous pentatomid bugs, the males produce a sex pheromone. Attraction appeared to peak in late afternoon to evening. The headspace volatiles collected from male and female T. perditor were analyzed by GC-MS and HPLC. A male-specific compound, methyl (2E,4Z,6Z)-decatrienoate (2E,4Z,6Z-10:COOMe), was identified along with a number of other compounds found in extracts from both sexes. Bioassays carried out with 2E,4Z,6Z-10:COOMe showed it was as attractive to females as the crude extract of male volatiles, suggesting that the male-produced sex pheromone consists of 2E,4Z,6Z-10:COOMe as a single component. Consecutive volatiles collections from males showed that 2E,4Z,6Z-10:COOMe began appearing in extracts from males about 9 d after the final molt, as the males became sexually mature.     

Genetic Basis to Divergence of Sex Pheromones in Two Closely Related Moths, <Emphasis Type="Italic">Ostrinia scapulalis</Emphasis> and <Emphasis Type="Italic">O. zealis</Emphasis>

Crossing experiments between two closely related moths, Ostrinia scapulalis and O. zealis, were conducted to gain insight into the genetic basis of the divergence of female sex pheromones. The sex pheromone of O. scapulalis comprises (E)-11- and (Z)-11-tetradecenyl acetates (E11 and Z11), and distinct genetic variation is found in the blend of components. This variation is largely controlled by a single autosomal locus with two alleles, A^E(sca) and A^Z(sca). E-type (A^E(sca)A^E(sca)) females produce a pheromone with amean E11:Z11 ratio of 99:1, whereas Z-type (A^Z(sca)A^Z(sca)) and I-type (A^E(sca)A^Z(sca)) females produce a pheromone with a mean of 3:97 and 64:36, respectively. O. zealis is distinctive in that it has a third pheromone component, (Z)-9-tetradecenyl acetate (Z9), in addition to E11 and Z11, and the typical blend ratio is 60:35:5 (Z9:E11:Z11). Our study revealed that Z9 production in O. zealis is mainly regulated by an autosomal recessive gene phr^(zea), which is suggested to be involved in the chain-shortening of a pheromone precursor fatty acid, and linked to A^E(zea), a gene corresponding to A^E(sca) in O. scapulalis. A few mutations in a gene involved in pheromone production could explain the dramatic shift between a two-component pheromone communication system in O. scapulalis and a three-component system in O. zealis.     

Sex Pheromone Components of Indian Gypsy Moth, <Emphasis Type="Italic">Lymantria obfuscata</Emphasis>

The Indian gypsy moth, Lymantria obfuscata (Lepidoptera: Lymantriidae), has been recognized as a distinct species since 1865 but closely resembles a diminutive form of gypsy moth, Lymantria dispar. We tested the hypothesis that the sex pheromones of L. obfuscata and L. dispar are similar. In laboratory mate acceptance studies, very few male L. dispar made copulatory attempts when paired with female L. obfuscata, suggesting that female L. obfuscata emit one or more pheromone components antagonistic to male L. dispar. In coupled gas chromatographic–electroantennographic detection (GC–EAD) analyses of pheromone gland extract of female L. obfuscata, (Z)-2-methyloctadec-7-ene (2Me-7Z-18Hy) and (7R,8S)-cis-7,8-epoxy-2-methyloctadecane [(+)-disparlure] were most abundant and elicited the strongest responses from male L. obfuscata antennae. In field experiments near Solan (Himachal Pradesh, India), 2Me-7Z-18Hy and (+)-disparlure in combination attracted more male L. obfuscata than did either component alone. This two-component sex pheromone contrasts with the single-component sex pheromone [(+)-disparlure] of L. dispar. The contrasting composition of the lymantriid communities inhabited by L. obfuscata and L. dispar may explain why 2Me-7Z-18Hy is a pheromone component in L. obfuscata and a pheromone antagonist in L. dispar and why (−)-disparlure reduces pheromonal attraction of male L. dispar but not male L. obfuscata.     

New Pheromone Components of the Grapevine Moth <Emphasis Type="Italic">Lobesia botrana</Emphasis>

Analysis of extracts of sex pheromone glands of grapevine moth females Lobesia botrana showed three previously unidentified compounds, (E)-7-dodecenyl acetate and the (E,E)- and (Z,E)-isomers of 7,9,11-dodecatrienyl acetate. This is the first account of a triply unsaturated pheromone component in a tortricid moth. The monoenic acetate (E)-7-dodecenyl acetate and the trienic acetate (7Z,9E,11)-dodecatrienyl acetate significantly enhanced responses of males to the main pheromone compound, (7E,9Z)-7,9-dodecadienyl acetate, in the wind tunnel. The identification of sex pheromone synergists in L. botrana may be of practical importance for the development of integrated pest management systems. Electronic supplementary material Supplementary material to this paper is available in electronic form at and accessible for authorised users.     

Pheromone-based Arrestment Behavior in the Common Silverfish, <Emphasis Type="Italic">Lepisma saccharina</Emphasis>, and Giant Silverfish, <Emphasis Type="Italic">Ctenolepisma longicaudata</Emphasis>

Aggregations of the common silverfish, Lepisma saccharina, and giant silverfish, Ctenolepisma longicaudata (both Thysanura: Lepismatidae), are mediated by species-specific pheromones. In dual-choice, still-air olfactometer experiments, filter paper previously exposed to 12 male, female, or juvenile L. saccharina or C. longicaudata arrested conspecifics regardless of developmental stage or sex. Arrestment responses required physical contact with the pheromone. Insect-derived frass, scales, antennae, and setae, as well as salivary gland content, are not the source of the contact pheromone in L. saccharina. Lepisma saccharina did not respond to the pheromone of C. longicaudata, nor to that of another thysanuran, the firebrat Thermobia domestica. However, C. longicaudata responded to pheromones of both L. saccharina and T. domestica, whereas T. domestica responded to the C. longicaudata but not L. saccharina pheromone. These results support the hypothesis that a closer phylogenetic relationship exists between C. longicaudata and T. domestica than between C. longicaudata and L. saccharina, but a definitive conclusion must await molecular genetic analyses of all three species.     

Trail-following behavior ofReticulitermes hesperus Banks (Isoptera: Rhinotermitidae)

The behavior ofReticulitermes hesperus Banks pseudergates (workers) was assessed on artificial trails containing different concentrations of sternal gland extract. On nongiadient trails, more pseudergates were recruited to trails of greater pheromone concentration, they traveled a greater distance without pausing, and their rate of locomotion increased over that observed on trails of lesser concentration (positive orthokinesis). Of the individuals pausing before completing trails of high concentration, fewer left the trails or reversed direction (negative klinokinesis) than on trails of lower concentration. Termites walking down concentration gradients failed to complete these trails to the low-concentration termini. At a point representing an average decrease of slightly more than 10-fold in the original concentration of pheromone, individuals reversed their direction of travel and returned to the high-concentration terminus. Termites walking up pheromone gradients proceeded to the high-concentration termini without reversing direction.R. hesperus pseudergates are thus able to orient along a gradient of trail pheromone by longitudinal klinotaxis.     

EFFECT OF PBAN ON PHEROMONE PRODUCTION BY MATED <Emphasis Type="Italic">Heliothis virescens</Emphasis> AND <Emphasis Type="Italic">Heliothis subflexa</Emphasis> FEMALES

Mated female Heliothis virescens and H. subflexa were induced to produce sex pheromone during the photophase by injection of pheromone biosynthesis activating neuropeptide (PBAN). When injected with 1 pmol Hez-PBAN, the total amount of pheromone that could be extracted from glands of mated females during the photophase was similar to that extracted from virgin females in the scotophase. The PBAN-induced profile of pheromone components was compared between mated, PBAN-injected females and virgin females during spring and fall. Virgin females exhibited some differences in the relative composition of the pheromone blend between spring and fall, but no such temporal differences were detected in PBAN-injected, mated females. Because the temporal variation in pheromone blend composition was greater for virgin females than for PBAN-injected females, PBAN can be used to determine a females native pheromone phenotype. This procedure has the advantages that pheromone glands can be extracted during the photophase, from mated females that have already oviposited.     

Sex Pheromone of the Dogwood Borer, <Emphasis Type="Italic">Synanthedon scitula</Emphasis>

The sex pheromone of female dogwood borers (DWB) Synanthedon scitula (Harris) (Lepidoptera: Sesiidae) was determined to be an 88:6:6 ternary blend of (Z,Z)-3,13-octadecadienyl acetate (Z,Z-3,13-ODDA), (E,Z)-2,13-octadecadienyl acetate (E,Z-2,13-ODDA), and (Z,E)-3,13-octadecadienyl acetate (Z,E-3,13-ODDA) by gas chromatography–electroantennographic detection (GC–EAD) and gas chromatography–mass spectrometry (GC–MS). The major sex pheromone component, Z,Z-3,13-ODDA, was attractive as a single component. A blend of Z,Z-3,13-ODDA with 1–3% of E,Z-2,13-ODDA (binary blend) was more attractive than the single component. A third component, Z,E-3,13-ODDA, was sometimes observed in GC–EAD analyses, and enhanced attraction to the binary blend in some field bioassays. Lures containing 1 mg of binary and ternary blends attracted 18 and 28 times more male DWB moths, respectively, than caged virgin females in field trials. Attraction was strongly antagonized by addition of as little as 0.5% of E,Z-3,13-octadecadienyl acetate (E,Z-3,13-ODDA). In a period of 12 wk in 2004, more than 60,000 males were captured in sticky traps baited with synthetic pheromone blends in six apple orchards in Virginia, West Virginia, and North Carolina. Lure longevity trials showed that ∼76% of the pheromone remained in rubber septum lures after 12 wk in the field.     

Synthesis,characterization and antibacterial activity of quaternized <Emphasis Type="Italic">N</Emphasis>,<Emphasis Type="Italic">O</Emphasis>-(2-carboxyethyl) chitosan

N,O-(2-carboxyethyl)chitosan (N,O-2-CEC) was prepared from chitosan with 3-chloropropionic acid as modifying agent and NaOH as catalyst. Different quaternary ammonium groups were introduced into N,O-2-CEC by the reaction between N,O-2-CEC and different 2,3-epoxypropyl trialkyl ammonium chlorides in the presence of 25% NaOH aqueous solution, and obtained different quaternized N,O-2-carboxyethyl chitosans (QCECs). Structures of QCECs were characterized by FT-IR, ¹HNMR and gel permeation chromatography (GPC). Antimicrobial activity of QCECs was evaluated against a gram-negative bacterium Escherichia coli and a gram-positive bacterium Staphylococcus aureus. Compared with N,O-2-CEC and quaternized chitosans, the QCECs had much stronger antimicrobial activity, which increased with increasing chain length of the alkyl in the quaternary ammonium groups. The presence of benzyl in quaternary ammonium groups could endow QCECs with much better antimicrobial activity.     

Male-Produced Aggregation Pheromone of the Cerambycid Beetle <Emphasis Type="Italic">Rosalia funebris</Emphasis>

We report the identification, synthesis, and field bioassays of a volatile, male-produced aggregation pheromone of a long-horned beetle, the banded alder borer, Rosalia funebris Mots. Headspace collections from males contained a major male-specific compound, (Z)-3-decenyl (E)-2-hexenoate, and several minor components, identified as (Z)-3-decenol, (Z)-3-nonenyl (E)-2-hexenoate, and (Z)-3-decenyl (E)-3-hexenoate. The antennae of both males and females responded strongly to (Z)-3-decenyl (E)-2-hexenoate. We collected significant numbers of adult R. funebris in field bioassays using traps baited with this compound. This pheromone structure is unprecedented in the literature of cerambycid pheromones and distinct from the more common diol/hydroxyketone pheromone motif of many other species of the diverse subfamily Cerambycinae. This is the first pheromone identified for a species in the tribe Rosaliini. Electronic supplementary material  The online version of this article (doi:) contains supplementary material, which is available to authorized users.