Identification of the sex pheromone of Conogethes pluto: a pest of Alpinia

In recent years, Conogethes pluto (Lepidoptera: Crambidae) has become a major pest of Alpinia and other ornamental gingers in the Northern Territory and Queensland, Australia. This pest damages the flowers and bores into the stems, causing substantial losses to production. Currently, no synthetic sex pheromone is available to monitor or control this pest. This work aims at the identification of the sex pheromone of this pest. Analysis of the sex pheromone gland of female C. pluto by gas chromatography/electroantennogram detector revealed the presence of seven candidate pheromone compounds that elicited electroantennogram responses. Using gas chromatography/mass spectrometry analysis and micro-derivatization reactions, six compounds were identified as (E)-10-hexadecenal, as the main pheromone compound, (Z)-10-hexadecenal, hexadecanal, (E)-10-hexadecen-1-ol, (10E,12E)-hexadeca-10,12-dienal and (3Z,6Z,9Z)-tricosa-3,6,9-triene as minor pheromone compounds. In two-field trapping experiments, C. pluto responded to the six-component blend, and three of six compounds, i.e., (E)-10-hexadecenal, (3Z,6Z,9Z)-tricosa-3,6,9-triene, and (10E,12E)-hexadeca-10,12-dienal were shown to be necessary for attraction. In a subsequent experiment testing various doses (i.e., 0.01, 0.1, and 1 mg) of the six-component blend, the largest number of males was captured in traps baited with a lure loading of 1 mg. The availability of the sex pheromone of C. pluto will enable monitoring and provides the basis for additional control options for this pest.     

Comparative studies on the sex pheromones of Ostrinia spp. in Japan: the burdock borer, Ostrinia zealis

Summary. To gain insight into the evolution of the sex pheromone communication system in Ostrinia (Lepidoptera Pyralidae), the sex pheromone of the burdock borer, O. zealis was analyzed by means of gas chromatography-electroantennographic detection (GC-EAD), GC-mass spectrometry and a series of bioassays. Four EAD-active compounds were detected in the female sex pheromone gland extract, and these were identified as tetradecyl acetate (14:OAc), (Z)-9-tetradecenyl acetate (Z9–14:OAc), (E)-11-tetradecenyl acetate (E11-14:OAc) and (Z)-11-tetradecenyl acetate (Z11-14:OAc). The average amounts (ratio) of the four compounds in single sex pheromone glands were 2.5 ng (13%), 11.6 ng (61%), 4.1 ng (21%) and 0.9 ng (5%), respectively. In a wind-tunnel bioassay, the ternary blend of Z9-, E11- and Z11-14:OAc at a ratio found in the sex pheromone gland elicited the same behavioral responses from the males as did virgin females. 14:OAc did not show any enhancement or inhibition of the males’ behavioral responses when added to the ternary blend. The attractiveness of the 3-component lure to O. zealis males was also confirmed by field trapping experiments. Based on these results, we concluded that the sex pheromone of O. zealis is composed of Z9-14:OAc, E11-14:OAc and Z11-14:OAc at a ratio of 70:24:6. The evolutionary changes of the sex pheromones in Ostrinia are also discussed based on the presently available information on the sex pheromones and phylogenetic relationships of Ostrinia spp. Received 25 September 1998; accepted 2 December 1998.     

Sex pheromone communication of tentiform leaf-miners <Emphasis Type="Italic">Phyllonorycter insignitella</Emphasis> and <Emphasis Type="Italic">Ph. nigrescentella</Emphasis> from two related species groups

Summary.  Females of both species start their pheromone-releasing activity on the second day after emergence at the beginning of the photophase. During the present work, a peak of calling activity with close to 100% of active Ph. nigrescentella females was registered 1.5 hour after the light had been put on. The high pheromone release behaviour with 50% active females lasted for 3 hours. The calling activity of the group of females was about 6 h/day. The beginning of a photophase under laboratory conditions or an early morning in nature is a common period for sex pheromone release in the genus Phyllonorycter. (8Z,10E)-tetradecadien-1-yl acetate (8Z,10E-14:Ac), (8Z,10E)-tetradecadien-1-ol (8Z,10E-14:OH) and (8E,10Z)-tetradecadien-1-yl acetate (8E,10Z-14:Ac) in the ratio 96:4:traces as well as 8Z,10E-14:Ac and 8Z,10E-14:OH in the ratio 88:12 collected by Solid Phase Micro Extraction (SPME) were found to be specific for the calling periods of virgin Phyllonorycter insignitella and Ph. nigrescentella females respectively. Field trapping experiments demonstrated that all three compounds are important for the attraction of Ph. insignitella males while only 8Z,10E-14:Ac is the essential sex pheromone component for Ph. nigrescentella. The pheromone activity of all three compounds is reported for the first time. Addition of either 8Z,10E-14:OH or 8E,10Z-14:Ac to 8Z,10E-14:Ac did not have a significant effect on the attraction of Ph. nigrescentella males, while the efficiency of the three component blend was 5 times lower as compared to that of 8Z,10E-14:Ac. Our data demonstrate that 8Z,10E-14:OH and 8E,10Z-14:Ac play a dual function, they are minor sex pheromone components of Ph. insignitella essential for attraction of conspecific males and show an allelochemical, antagonistic effect on Ph. nigrescentella males and, thus, ensuring specificity of the mate location signal in two related Phyllonorycter species.     

Identification and field evaluation of the female sex pheromone of Stathmopoda masinissa in Korea

The sex pheromone of Stathmopoda masinissa Meyrick, an important pest of persimmon fruit in East Asia such as Korea, China, and Japan, was investigated. A lure using (E4,Z6)-4,6-hexadecadienyl acetate (E4,Z6-16Ac), which was identified as a sex pheromone compound of Japanese population, did not work at all for Korean population. Therefore, components in the abdominal extract of the moth were identified and their attractiveness was evaluated in the field. Two components, E4,Z6-16Ac and (E4,Z6)-4,6-hexadecadien-1-ol (E4,Z6-16OH) were identified from the extract of female abdominal extract in a ratio of 10–15:90–85 by GC–MS analysis with synthetic standards. E4,Z6-16Ac and E4,Z6-16OH were previously identified as EAG-active components of this moth in Japanese population. However, (E4,Z6)-4,6-hexadecadienal (E4,Z6-16Ald), which is one of the abdominal extract components and EAG-active component in Japanese population, was not detected in our samples. In the persimmon orchard, single component of E4,Z6-16Ac or E4,Z6-16OH was not attractive. However, the 1:1 mixture of the two components significantly increased the captures of male S. masinissa. Interestingly, traps baited with E4,Z6-16Ac captured significantly higher number of Oedematopoda ignipicta (Lepidoptera: Stathmopodidae) than the traps baited with E4,Z6-16OH or blend of the two components. The attractiveness of E4,Z6-16Ac to O. ignipicta is a new finding.     

Female sex pheromone of Ostrinia orientalis – throwing a light on the relationship between O. orientalis and the European corn borer, O. nubilalis

Summary. The sex pheromone of Ostrinia orientalis (Lepidoptera: Crambidae) was analyzed by gas chromatography–electroantennographic detection (GC–EAD), GC–mass spectrometry and a series of bioassays. Three EAD-active compounds were detected in the female sex pheromone gland extract, and identified as tetradecyl acetate (14:OAc), (Z)-11-tetradecenyl acetate (Z11-14:OAc) and (E)-11-tetradecenyl acetate (E11-14:OAc). The titers (ratio) of 14:OAc, Z11-14:OAc and E11-14:OAc in 3-day-old virgin females were 0.49 ng (10), 4.86 ng (98) and 0.10 ng (2), respectively. In a wind-tunnel bioassay, the 98:2 blend of Z11- and E11-14:OAc, but not Z11-14:OAc alone, elicited the same male behavioral responses as virgin females and crude gland extracts. 14:OAc was inactive by itself, and did not show any synergistic effect on the binary blend. Field trapping experiments also confirmed the attractiveness of the binary blend to O. orientalis males. Based on these results, we concluded that the sex pheromone of O. orientalis is a 98:2 mixture of Z11-14:OAc and E11-14:OAc. This sex pheromone is very similar to that of the Z-type European corn borer, O. nubilalis. The present finding raises the question of whether O. orientalis , which is indistinguishable from O. nubilalis based on external morphology, is a biologically distinct species independent from O. nubilalis.     

Sex pheromones and attractants in the Eucosmini and Grapholitini (Lepidoptera,Tortricidae)

Summary The geometric isomers (E,E)-, (E,Z)-, (Z,E)-, and (Z,Z)-8,10-dodecadien-1-yl acetate were identified as sex pheromone components or sex attractants in the tribes Eucosmini and Grapholitini of the tortricid subfamily Olethreutinae. Species belonging to the more ancestral Tortricinae were not attracted. Each one isomer was behaviourally active in males ofCydia andGrapholita (Grapholitini), either as main pheromone compound, attraction synergist or attraction inhibitor. Their reciprocal attractive/antagonistic activity in a number of species enables specific communication with these four compounds.Pammene, as well as otherGrapholita andCydia responded to the monoenic 8- or 10-dodecen-1-yl acetates. Of the tribes Olethreutini and Eucosmini,Hedya, Epiblema, Eucosma, andNotocelia trimaculana were also attracted to 8,10-dodecadien-1-yl acetates, but several otherNotocelia to 10,12-tetradecadien-1-yl acetates. The female sex pheromones ofC. fagiglandana, C. pyrivora, C. splendana, Epiblema foenella andNotocelia roborana were identified. (E,E)- and (E,Z)-8,10-dodecadien-1-yl acetate are producedvia a commonE9 desaturation pathway inC. splendana. CallingC. nigricana andC. fagiglandana females are attracted to wingfanning males.     

Heritable pheromone blend variation in a local population of the butterbur borer moth Ostrinia zaguliaevi (Lepidoptera: Crambidae)

Summary. In a local population of Ostrinia zaguliaevi Mutuura & Munroe (Lepidoptera: Crambidae), extensive variation was found in the blend ratio of three sex pheromone components, (Z)-9-tetradecenyl acetate (Z9-14:OAc, 10.2-63.8%), (Z)-11-tetradecenyl acetate (Z11-14:OAc, 32.2-86.8%), and (E)-11-tetradecenyl acetate (E11-14:OAc, 2.1-11.9%). The variation was observed over a three-year period (2002-2004). Mother-daughter regression analyses have shown that although the heritability of the minor component E11-14:OAc was not significant, the heritability of the proportions of Z9-14:OAc and Z11-14:OAc were substantial (0.5–0.6). In artificial selection experiments, the mean % Z9-14:OAc in the sex pheromone changed significantly within three generations (37% in the control line, 48 and 52% for two lines selected for increase, and 23 and 30% for two lines selected for decrease). Despite these changes, the amounts of fatty acyl pheromone precursors, (Z)-9-, (Z)-11- and (E)-11-tetradecenoate, in the pheromone gland were not significantly affected by the selection. Taken together, variation in the pheromone blend of O. zaguliaevi is likely to be attributable to a few genes involved in the reduction or acetylation of fatty acyl pheromone precursors, the last two steps in pheromone biosynthesis.     

Neocembrene A, a major component of the trail-following pheromone in the genus Prorhinotermes (Insecta, Isoptera, Rhinotermitidae)

Summary. The diterpene neocembrene A or (1E,5E,9E,12R)-1,5,9-trimethyl-12-(1-methylethenyl)-1,5,9-cyclotetradecatriene, known as the trail-following pheromone of the advanced Termitidae Nasutitermitinae Nasutitermes exitiosus and Trinervitermes bettonianus, has been identified after SPME-GC/MS as the major component of the trail-following pheromone of the Rhinotermitidae Prorhinotermitinae, Prorhinotermes canalifrons and P. simplex. In all the other Rhinotermitidae studied until now, the major component of their trail pheromones is dodecatrienol ((3Z,6Z,8E)-dodeca-3,6,8-trien-1-ol). This biochemical data further add to the anatomical and molecular characteristics that give a special status to the taxon Prorhinotermes among Rhinotermitidae. In Prorhinotermes canalifrons and P. simplex, neocembrene A was the only secretory compound specific to the sternal gland surface that could be detected after SPME. It elicited orientation as well as recruitment behavioral effects. However, the comparison of the respective biological activities triggered by neocembrene A and by sternal gland secretion suggests that minor components of the latter are acting in synergy with neocembrene A.     

Sex pheromone of the large aspen tortrix, Choristoneura conflictana(Lepidoptera: Tortricidae)

Summary. Three components that elicited antennal response from male Choristoneura conflictana were found from female gland extracts analyzed using a coupled gas chromatographic-electroantennographic detector system. The main component in gland extracts was (Z)-11-tetradecenal (Z11-14:Ald). Two minor components also elicited antennal response: (E)11-tetradecenal (E11-14:Ald) and (Z)-11- tetradecen-1-ol (Z11-14:OH). Analysis of effluvia indicated that calling virgin females release mostly Z11-14:Ald and trace amounts of Z11-14:OH. Field and wind tunnel behavioral studies showed that Z11-14:Ald alone attracted male moths in a dose response pattern. Tests comparing male response to blends of components detected in gland extracts showed that addition of 1.8% of E11-14:Ald to Z11-14:Ald did not influence male moths in the wind tunnel, but resulted in significantly lower trap captures in the field. The threecomponent blend [Z11-14:Ald (100), E11-14:Ald (1.8), Z11-14:OH (11)], was less attractive than Z11-14:Ald alone in both field and wind tunnel studies. Traps baited with two virgin female moths were equally attractive to males as traps baited with the three-component synthetic blend but less attractive than traps baited with Z11-14:Ald alone. Field tests of various blends of the two components (Z11-14:Ald, Z11-14:OH) detected in the females’ effluvia showed that the addition of 1–10% Z11-14:OH to Z11-14:Ald did not affect the males’ response to Z11-14:Ald. Our data demonstrate that female C. conflictana release sex pheromone components in a different ratio than they are stored in the pheromone gland. The sex pheromone is comprised of a single component, Z11-14:Ald, that can be used to monitor mated and virgin male C. conflictana throughout their flight period.     

Identification and field bioassays of the sex pheromone of the yellow-legged clearwing Synanthedon vespiformis (Lepidoptera: Sesiidae)

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^? 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.     

Identification and biological activity of sex pheromone components from females of the plum moth Illiberis rotundata Jordan (Lepidoptera: Zygaenidae: Procridinae)

The plum moth, Illiberis rotundata Jordan (Lepidoptera: Zygaenidae: Procridinae), is a pest of orchards in Japan and China. Few chemical ecological studies have been directed towards the Zygaenidae and particularly the Procridinae. To investigate the sex pheromone of this species, extracts of pheromone glands from adult female I. rotundata were analyzed by coupled gas chromatography-electroantennography (GC-EAG) and coupled gas chromatography-mass spectrometry (GC-MS). Whilst GC-EAG on male moths showed an active peak, identified as 2-butyl (7Z)-dodecenoate, GC-MS also revealed the presence of the homologue 2-butyl (9Z)-tetradecenoate. Electroantennographic investigations, as well as field tests, strongly suggested the natural compounds to have the (R)-configuration at the stereogenic centre. Field results demonstrate 0.2 mg of a 1:1-mixture of (2R)-butyl (7Z)-dodecenoate and (2R)-butyl (9Z)-tetradecenoate to be a powerful lure that may be used in pest control measures against I. rotundata. The chemical structures of the new pheromone components show the same features as those of other zygaenid species: unsaturated fatty acids esterified with a short chain chiral alcohol. This is the first example of a two-component blend constituting the pheromone of a procridinid species.     

Green leaf volatiles enhance sex attractant pheromone of the tobacco budworm,Heliothis virescens (Lep.: Noctuidae)

Summary Components of the green leaf volatile complex (Z-3-hexenyl acetate andE-2-hexenyl acetate) were shown to enhance responses of tobacco budworm,Heliothis virescens, males to the sex attractant pheromone of conspecific females in the field. The results are discussed with regard to green leaf volatiles which enhance the attractant pheromone of a cohabiting species, and serve as attractants of a parasitoid of conspecific larvae.     

Host-plant green-leaf volatiles synergize the synthetic sex pheromones of the corn earworm and codling moth (Lepidoptera)

Summary The capture of adult male moths in female sex pheromone traps of two key agricultural pests, the corn earworm (Helicoverpa zea) and the codling moth (Cydia pomonella), is enhanced or synergized by a certain group of host-plant volatiles, the green-leaf volatiles (GLVs). Since female adults of both species call and release their sex pheromones while perched upon the leaves of their host-plants, the volatile constituents from the leaves of a number of host-plants were compared. Sex pheromone traps containing one of the prominent leaf volatiles of certainH. zea hosts, (Z)-3-hexenyl acetate, not only significantly increased the capture ofH. zea males but were preferred over traps baited only with sex pheromone. Similarly, traps baited with synthetic sex pheromome ofC. pomonella plus a blend of GLVs captured significantly more males than traps baited only with sex pheromone. Since male moths are not captured in traps baited only with these GLVs, it appears that these GLVs act as pheromone synergists which increase or enhance the attraction or arrestment of male moths in pheromone traps.     

(<Emphasis Type="Italic">Z,Z</Emphasis>)-11,13-Hexadecadienyl acetate and (<Emphasis Type="Italic">Z,E</Emphasis>)-11,13,15-hexadecatrienyl acetate: synergistic sex pheromone components of oak processionary moth,Thaumetopoea processionea (Lepidoptera: Thaumetopoeidae)

Summary. Our objective was to identify sex pheromone components of the oak processionary moth, Thaumetopoea processionea (Lepidoptera: Thaumetopoeidae), whose larvae defoliate oak, Quercus spp., forests in Eurasia and impact human health. Coupled gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometric (MS) analyses of pheromone gland extract of female T. processionea revealed two consistently EAD-active compounds. They were identified as (Z,Z)-11,13-hexadecadienyl acetate (Z11,Z13-16:OAc) and (Z,E)-11,13,15-hexadecatrienyl acetate (Z11,E13,15-16:OAc) by comparative GC, GC-MS and GC-EAD analyses of insect-produced compounds and authentic standards. In replicated field experiments (2000, 2001) in Nordbaden, Südbaden and Sachsen-Anhalt (Germany), Z11,Z13-16:OAc and Z11,E13,15-16:OAc in combination, but not singly, attracted significant numbers of male moths. It will now be intriguing to investigate whether Z11,E13,15-16:OAc, or its corresponding alcohol or aldehyde, serves as a pheromone component also in other species of the Thaumetopoeidae.     

Identification of the putative aggregation pheromone components emitted by the European earwig, <Emphasis Type="Italic">Forficula auricularia</Emphasis>

The European earwig, Forficula auricularia is an invasive insect found in many temperate regions of the world and is regarded as an urban and agricultural pest of numerous crops. Several studies have shown that F. auricularia aggregate in large numbers with the use of an aggregation pheromone. However, the identity of compounds which constitute the pheromone remains elusive. Our aim was to isolate and identify the aggregation pheromone used by F. auricularia using both solvent washes of individuals and thermal desorption of substrates exposed to earwigs. Solvent washes of male, female and juvenile earwigs isolated 51 different branched and unbranched alkanes, alkenes and alkadienes. Substrates exposed to aggregating field populations in situ were demonstrated to be attractive to earwigs after less than 24 h of exposure. Analysis of these substrates using thermal desorption and solvent washes showed that hydrocarbons were the only detectable compounds laid down by earwigs on these surfaces. Significant behavioural responses were observed to synthetic blends of the unsaturated hydrocarbons containing (Z)-7-tricosene, (Z)-9-tricosene, (Z)-7-pentacosene and (Z)-9-pentacosene at ≥25 insect equivalents in field-based bioassays. However, behavioural responses to these blends proved inconsistent particularly later in the field season, possibly due to a missing component within the pheromone blend or plasticity in the pheromones production and response.     

Behavioral and electrophysiological responses of the emerald ash borer, Agrilus planipennis, to induced volatiles of Manchurian ash, Fraxinus mandshurica

Summary. We investigated the volatile emissions of Manchurian ash seedlings, Fraxinus mandshurica, in response to feeding by the emerald ash borer, Agrilus planipennis, and to exogenous application of methyl jasmonate (MeJA). Feeding damage by adult A. planipennis and MeJA treatment increased volatile emissions compared to unexposed controls. Although the same compounds were emitted from plants damaged by beetles and treated with MeJA, quantitative differences were found in the amounts of emissions for individual compounds. Adult virgin female A. planipennis were similarly attracted to volatiles from plants damaged by beetles and those treated with MeJA in olfactometer bioassays; males did not respond significantly to the same volatiles. Coupled gas chromatographic-electroantennogram detection (GC-EAD) revealed at least 16 antennally-active compounds from F. mandshurica, including: hexanal, (E)-2-hexenal, (Z)-3-hexen-1-ol, 3-methyl-butylaldoxime, 2-methyl-butylaldoxime, (Z)-3-hexen-1-yl acetate, hexyl acetate, (E)-β-ocimene, linalool, 4,8-dimethyl-1,3,7-nonatriene, and E,E-α-farnesene. Electroantennogram (EAG) dose–response curves using synthetic compounds revealed that females had a stronger EAG response to linalool than males; and male responses were greater to: hexanal, (E)-2-hexenal, (Z)-3-hexen-1-ol, 3-methyl-butylaldoxime, 2-methyl-butylaldoxime, and hexyl acetate. These results suggest that females may use induced volatiles in long-range host finding, while their role for males is unclear. If attraction of females to these volatiles in an olfactometer is upheld by field experiments, host plant volatiles may find practical application in detection and monitoring of A. planipennis populations.     

A synomone imparting distinct sex pheromone communication channels for Choristoneura rosaceana (Harris) and Pandemis limitata (Robinson) (Lepidoptera: Tortricidae)

Summary. Male obliquebanded leafrollers, Choristoneura rosaceana (Harris), were induced to respond to a pheromone source tainted with a behavioural antagonist, Z9-tetradecenyl acetate, when a source releasing the antagonist was placed 10 cm upwind of the tainted source in a wind tunnel. However, placement of the antagonist upwind of an attractive pheromone source did not interrupt pheromone-mediated responses. Placement of a source releasing Z9-tetradecenyl acetate, a minor pheromone component of the sympatric species, the threelined leafroller, Pandemis limitata (Robinson), upwind of a calling P. limitata female, reduced conspecific male pheromone-mediated response but resulted in upwind flight by male C. rosaceana and contact with heterospecific females. Male P. limitata locked on and flew upwind to but did not contact heterospecific females when a source releasing Z9-tetradecenyl acetate was positioned upwind of a calling C. rosaceana female. In the field, adaptation or habituation to Z9-tetradecenyl acetate caused by atmospheric treatment with this compound apparently resulted in reciprocal heterospecific pheromone responses. More C. rosaceana males were captured in traps baited with their pheromone and the behavioural antagonist in small field plots treated atmospherically with Z9-tetradecenyl acetate than in nontreated control plots. Fewer male P. limitata were captured in traps baited with their own pheromone, or with C. rosaceana pheromone tainted with Z9-tetradecenyl acetate in plots treated atmospherically with Z9-tetradecenyl acetate than in nontreated control plots. We argue that Z9-tetradecenyl acetate is an important synomone which assists in partitioning the sexual chemical communication channels of C. rosaceana and P. limitata. Received 9 February 1999; accepted 22 March 1999.     

Communication ecology of webbing clothes moth: 4. Identification of male- and female-produced pheromones

Summary. We investigated the hypothesis that aggregation signals produced by male webbing clothes moths (WCM), Tineola bisselliella (Hum.) (Lepidoptera: Tineidae), and close-range male attractant signals produced by females have a pheromonal basis, at least in part. Gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometric analyses of bioactive methanolic extracts of male WCM disclosed three candidate pheromone components: hexadecanoic acid methyl ester (16:Ester), (Z)-9-hexadecenoic acid methyl ester (Z9—16:Ester), and octadecanoic acid methyl ester (18:Ester). In bioassay experiments in a large Plexiglas™ arena, a blend of synthetic 16:Ester plus Z9—16:Ester was attractive to male and virgin (but not mated) female WCM; the 18:Ester was inactive. GC-EAD analyses of pheromone gland extracts from female WCM revealed (E,Z)-2,13-octadecadienal (E2Z13—18:Ald) and (E,Z)-2,13-octadecadienol (E2Z13—18:OH) as candidate sex pheromone components. In arena bioassay experiments, 1—5 female equivalents of synthetic E2Z13—18:Ald (0.2 ng) and E2Z13—18:OH (0.1 ng) were more attractive to male WCM than were two virgin female WCM. We anticipate that the combination of aggregation and sex pheromones, male-produced sonic aggregation signals, and habitat-derived semiochemicals will be highly effective in attracting male and female WCM to commercial traps. Received 12 January 2001; accepted 8 June 2001.     

Differential activity of non-fluorinated and fluorinated analogues of the European corn borer pheromone

Summary.  The differing antagonist activity of (Z)-13-hexadecen-2-one (Z11 – 14 :MK, 1) and its 1,1,1-trifluoro derivative (Z11 –14 :TFMK, 2), two closely related analogues of the European corn borer pheromone Ostrinia nubilalis (Z strain), and their rationale is reported. Both chemicals exhibited some electrophysiological activity, and topical application of 10 pg of pheromone analogue on male antennae was sufficient to induce significantly lower depolarization responses to the pheromone versus untreated insects. In a wind tunnel, the number of European corn borer males attracted to sources containing mixtures of 1 + pheromone in ratios ≥ 1 :1 was significantly lower than the number attracted to a source containing pheromone alone. Source contact behaviour was dramatically impaired when the 1 + pheromone blend reached a ratio of 10 :1, in which only 2% of males displayed source contact in the presence of antagonist. When compound 1 was present at the source, males usually flew upwind with occasional downwind reversals; when compound 2 was present at the lure, males performed wider crosswind reversals, with little progress toward the source. In the field, traps baited with mixtures of both compounds with the pheromone in ratios of 5 :1 and 10 :1 elicited a significantly decreased number of male catches. In esterase inhibition assays, compound 2 was a potent inhibitor (IC₅₀ = 70 nM), whereas the non-fluorinated compound 1 was not. The different activity of both compounds is presumed to be due to different mechanisms of action; considerations for using methyl ketone analogues as new behavioural antagonists of the pheromone are outlined.     

Sex pheromone of the tea aphid,Toxoptera aurantii (Boyer de Fonscolombe) (Hemiptera: Aphididae)

The tea aphid, Toxoptera aurantii, also called the “black citrus aphid”, is one of the most destructive insect pests in commercial tea plantations and gardens in southern China. In autumn, declining day length triggers production of winged T. aurantii sexuparae, which produce both winged males and wingless oviparae. Oviparous females then release sex pheromone that attracts potential mates. GC–MS analysis of volatile headspace extracts of T. aurantii oviparae revealed that they emit (4aS,7S,7aR)-nepetalactone (I) and (1R,4aS,7S,7aR)-nepetalactol (II) in a ratio of 4.3–4.9:1. Field-trapping experiments with synthetic I and II singly or as two-component blends of different doses and ratios showed significant attraction of T. aurantii males, as well as weak attraction of sexuparae. Identification of the T. aurantii sex pheromone provides a new opportunity for developing a pheromone-based monitoring and management strategy for the sexual phase of tea aphids and, possibly, the alate sexparous generation in late summer and fall.