(Z)-3-nonenol, (Z,Z)-3,6-nonadienol and (S,S)-(-)-epianastrephin: male produced pheromones of the Mexican fruit fly

(Z)-3-nonenol, (Z,Z)-3,6-nonadienol and (S,S)-(-)-epianastrephin proved active as male-produced pheromones which elicited behavioral responses from virgin female Mexican fruit flies (Anastrepha ludens) (Diptera: Tephritidae) in laboratory bioassays. All three chemicals elicited attraction and/or locomotor arrest when tested individually. When tested together, (Z)-3-nonenol inhibited the behavioral effect of (Z,Z)-3,6-nonadienol but either of the alcohols synergized the effect of (S,S)-(-)-epianastrephin. Quantities of the pheromones per male abdomen were: (Z)-3-nonenol-100 ng; (Z,Z)-3,6-nonadienol-40 ng; and total epianastrephin (R,R and S,S enantiomers)-700 ng. Relative to the quantities in abdominal extract, males released these chemicals during sexual display in a blend containing a higher proportion of the alcohols.

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Résumé Le (Z)-3-nonènol, le (Z,Z)-3,6-nonadiènol et le (S,S)-(-)-épianastréphine produits par les mâles de la mouche mexicaine du fruit (Anastrepha ludens) (Diptera: Tephritidae) ont attirés les femelles lors de tests conduits en laboratoire. Le pouvoir attractif du (Z)-3-nonènol est faible comparé à celui des deux autres phéromones. Evalués ensemble, le (Z)-3-nonènol inhibe l'attractivité du (Z,Z)-3,6-nonadiènol mais chacun des deux alcools synergise l'effet attractif de la (S,S)-(-)-épianastréphine. Les quantités recouvrées par mâle dans un extrait abdominal étaient respectivement de 100, 40 et 700 ng pour le (Z)-3-nonènol, le (Z,Z)-3,6-nonadiènol, et l'épianastréphine totale (R,R et S,S) énantiomères. Comparées à ces valeurs, le mélange élange émis par les mâles lors de leur cour sexuelle est plus riche in alcools. Le rapport (Z)-3-nonènol (Z,Z)-3,6-nonadiènol est cependant identique dans l'extrait abdominal et dans le mélange émis par les mâles.

     

(Z)-11-Hexadecenyl compounds as attractants for male microlepidoptera of the subfamilies Argyresthiinae, Glyphipteryginae, and Crambinae

Traps baited with Z11-16:Ac, Z11-16:Ald, Z11-16:OH, and Z13-18:Ac, singly or in mixtures, were tested for their attractivity for males of microlepidoptera in an apple orchard, a mixed deciduous forest, and a coniferous forest. In particular, Z11-16:Ac and Z11-16: Ald attracted some Crambinae, one Glyphipteryx species, and several species of Argyresthia, including the injurous species A. fundella (on fir), A. conjugella (on apple), A. pruniella (on cherry), and A. thuiella (on Thuja).

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Attraction sexuelle de microlépidoptères des sous-familles Argyresthiinae, Glyphipteryginae et Crambinae par des hexadécènes 11Z

Résumé L'attraction de microlépidoptères par des hexadécènes 11Z a été examinée en 1982 et 1983 à l'aide de pièges sexuels placés dans différents biotopes de Hollande. Ces pièges contenaient différents mélanges synthétiques d'acétoxy-1-hexadécènes 11Z (Z11-16:Ac), d'hexadécènal 11Z (Z11-16:Ald), d'hexadécénol 11Z (Z11-16:OH) et d'acétoxyl-1-octadécène 13Z (Z13-18:Ac). Les pièges étaient placés dans un verger de pommiers, dans un bois de feuillus aux essences diverses et dans un bois de résineux. Des mâles de 10 espèces de lépidoptères ont été capturés avec ces mélanges, parmi lesquels ceux de 3 espèces de Pyralidae, d'une espèce du genre Glyphipteryx et de 6 espèces du genre Argyresthia. Parmi les Argyresthia, certaines espèces sont considérées comme des déprédateurs: A. fundella sur sapin (Abies), A. conjugella sur pommier (Malus), A. pruniella sur cerisier (Prunus) et A. thuiella sur Thuja. Enfin, un tableau fournit 28 produits contenant des hexadécènes Z11 actuellement connus comme attractifs sexuels de microlépidoptères; la majorité des espèces appartient aux sous-familles Crambinae, Argyresthiinae, Glyphipteryginae et Acrolepiinae.

     

The effects of laboratory culturing on (Z)-9-tricosene (muscalure) quantities on female houseflies

Using gas chromatography the relative amounts of (Z)-9-tricosene (muscalure) and some other hydrocarbons on the cuticle of 1- to 20-day-old houseflies (Musca domestica L.) from different strains were determined. Flies from a WHO strain, in culture since 1961, and first-generation laboratory-cultured flies from two wild-type strains from a poultry breeding and a cow-house with pigsty, respectively, were compared. On WHO females hydrocarbons with 23–25 C atoms constituted about 65% of the total hydrocarbons, whereas on wild-type females less than 2% of these compounds was present. (Z)-9-tricosene comprised up to 20–30% of the total hydrocarbons on 5- to 20-day-old WHO females, whereas less than 0.5% (Z)-9-tricosene was present on the wild-type females. We also compared the amounts of (Z)-9-tricosene and some other hydrocarbons on female houseflies, kept in culture in the laboratory for several generations. It appeared that whereas on first-generation wild-type females hardly or no (Z)-9-tricosene could be detected, the amounts of this substance had increased considerably after some tens of generations in the laboratory. It is suggested that this was due to selection in subsequent generations of high-density populations. Production of (Z)-9-tricosene and of tricosane was shown to be closely linked. Selection did not affect the production of other cuticular hydrocarbons by the females. It is suggested that in mixed populations (both sexes together in a cage) in the course of time (Z)-9-tricosene is transferred from females to males and (Z)-9-heptacosene from males to females. It is concluded that reproductive ability of houseflies does not primarily depend on the amounts of (Z)-9-tricosene on females, although higher amounts of this substance may increase contacts between males and females.     

A sex pheromone component novel to the Geometridae identified fromEpirrita autumnata

(Z,Z,Z)-1,3,6,9-Heneicosatetraene was identified as a sex pheromone component ofEpirrita autumnata (Borkhausen), (Lepidoptera: Geometridae). Gas chromatography coupled with electroantennographic detection revealed one active peak from female pheromone gland extracts. The chemical identification of the compound was based on gas chromatography-mass spectrometry, chemical micro-reactions and unambiguous synthesis. In a field test, a rubber septum loaded with 3000 μg of this compound showed highest attraction of maleE. autumnata moths compared to lower doses and the control. The attraction of males to a 300 μg bait was equivalent to that obtained using live virgin females.     

A two-component sex attractant for males of the geometrid moth Alsophila quadripunctata

The binary mixture of the hydrocarbons (3Z,6Z,9Z)-3,6,9-nonadecatriene and (6Z,9Z)-6,9-nonadecadiene is a sex attractant for males of Alsophila quadripunctata Esp. (Lepidoptera, Geometridae). Triene/diene ratios from 1:1 to 1:0.01 attracted males in the field, the ratios 1:1 and 1:0.7 were most effective. The triene on its own also attracted males, but in significantly lower numbers than the 1:1 mixture. In a dosage test the highest dose, 1800 g of 1:0.8 [triene:diene] mixture applied to rubber caps was most effective. This is the first report of a geometrid sex attractant with field activity containing more than one component.

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Zusammenfassung Die binäre Mischung der Kohlenwasserstoffe (3Z,6Z,9Z)-3,6,9-Nonadecatrien [ZZZ3,6,9-19:H] und (6Z,9Z)-6,9-Nonadecadien [ZZ6,9-19:H] in den Verhältnissen 1:1 bis 1:0.01 erwies sich im Freiland als Sexuallockstoff für Männchen von Alsophila quadripunctata (Geometridae, Lepidoptera). Dabei besaß die 1:1-Mischung die beste Fängigkeit, das Nonadecatrien allein lockte schlechter, während das C₁₉-Alkadien unwirksam war. Ein Dosiswirksamkeitstest ergab bei Köderbeladungen von 1.8 mg (Trien:Dien + 1:0.8) die besten Fangergebnisse. Im Verlauf der Untersuchungen wurden weitere zwölf geometrische-oder positionsisomere C₁₉-Polyenkohlenwasserstoffe getestet, wobei keine der geprüften Verbindungen Attraktant-oder Inhibitorwirkung zeigte.

     

A comparison of responses from olfactory receptor neurons of<Emphasis Type="Italic"> Heliothis subflexa</Emphasis> and<Emphasis Type="Italic"> Heliothis virescens</Emphasis> to components of their sex pheromone

Single-cell electrophysiological recordings were obtained from olfactory receptor neurons in sensilla trichodea on male antennae of the heliothine species Heliothis subflexa and the closely related congener H. virescens. A large percentage of sensilla (72% and 81%, respectively, of all sensilla sampled) contained a single odor-responsive receptor neuron tuned to the major pheromone component of both species, Z-11-hexadecenal. A second population of sensilla on H. subflexa antennae (18%) housed receptor neurons that were tuned to Z-9-hexadecenal but also responded with less sensitivity to Z-9-tetradecenal. A similar population of sensilla (4%) on H. virescens male antennae housed receptor neurons that were shown to be tuned specifically only to Z-9-tetradecenal, with no response to even high dosages of Z-9-hexadecenal. A third population of sensilla (comprising 8% and 16% of the sensilla sampled in H. subflexa and H. virescens, respectively) housed two olfactory receptor neurons, one of which was tuned to Z-11-hexadecenyl acetate and the other tuned to Z-11-hexadecenol. In H. subflexa the Z-11-hexadecenyl acetate-tuned neuron also responded to Z-9-tetradecenal with nearly equivalent sensitivity. The behavioral requirements of males of these two species for distinct pheromonal blends was, therefore, reflected by the subtle differences in the tuning properties of antennal olfactory receptor neurons.Abbreviations MGC macroglomerular complex - ORN olfactory receptor neuron - Z9–14:Ald (Z)-9-tetradecenal - Z9–16:Ald (Z)-9-hexadecenal - Z11–16:Ac (Z)-11-hexadecenyl acetate - Z11–16:Ald (Z)-11-hexadecenal - Z11–16:OH (Z)-11-hexadecenol     

Selection for altered pheromone-component ratios in the pink bollworm moth,Pectinophora gossypiella (Lepidoptera: Gelechiidae)

Female pink bollworm moths, Pectinophora gossypiella(Saunders), were selected for altered component ratios of the long-distance sex pheromone, (Z, E)-and (Z, Z)-7,11- hexadecadienyl acetate. Selection for 12 generations increased the mean (± SD) percentage of the (Z, E)isomer from 42.9 ± 1.0 in the parental generation to 48.2 ± 1.2. Although statistically significant, a change of this magnitude may be transparent to males because of their relatively broad response spectrum. Selection for a lower percentage of the (Z, E)isomer yielded no change in the mean pheromone ratio. The total amount of pheromone produced declined in both selected lines. In the line selected for females producing a high percentage of the (Z, E)isomer, the duration of wing fanning by males to high (Z, E)blends was elevated.     

A pheromone mimic: disruption of mating communication in the navel orangeworm, Amyelois transitella, with Z,Z-1,12,14-heptadecatriene

A novel olefinic analog, Z,Z-1,12,14-heptadecatriene, was synthesized from Z,Z-11,13-hexadecadienal, a major pheromone component of the navel orangeworm, Amyelois transitella (Walker) (Lepidoptera: Pyralidae), and evaluated as a potential disruptant of mating communication in commercial almond orchards. The effectiveness of the triene as a disruptant was compared to that of the aldehyde by evaluating the reduction in captures of feral males in female-baited traps and the reduction in mating success for females. The triene was highly effective in bringing about reductions in male captures in traps in all tests relative to controls. This effectiveness lasted as long as 5 weeks in one test and was influenced by type of dispenser, release rate and proximity of dispensers to female-baited traps. In none of the tests did the triene outperform the aldehyde in reducing male captures. The results of mating success tests showed the triene to be ineffective relative to controls (26% reduction) while the aldehyde yielded 100% reductions in matings during a 6-day period.

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Résumé Le Z-Z-1,12,14-heptacécatriène, qui mime l'aldéhyde Z-Z-11,13-hexadécadénial, principal composé de la phéromone de A. transitella Walker, a été essayé pour interrompre les accouplements dans la nature. Un conditionnement avec plastique stratifié a mieux dispersé le triène que la présentation en capsules de polyéthylène. Comme dans le cas des autres produits examinés précédemment, ce triène a interrompu l'attraction sexuelle (réduction du nombre de mâles capturés dans les pièges, réduction du nombre d'accouplements) de A. transitella dans les vergers d'amandiers, pendant moins longtemps que l'aldéhyde. Placé dans des pièges contenant des femelles vierges, il est efficace comme l'aldehyde pendant 5 semaines, pendant 3 semaines lorsqu'il est placé autour des pièges et pendant 13 jours quand il est utilisé dans des parcelles de 9 arbres. Des essais ultérieurs avec d'autres présentations et des quantités plus élevées de triène devraient montrer si ce produit peut être utilisé pour l'interruption des accouplements. Les analogues de phéromones ont généralement une plus grande stabilité et un coût de synthèse moins élevé que les aldéhydes.

     

Antagonistic Effect of (Z)-11-Hexadecen-1-ol on the Pheromone-Mediated Flight of Helicoverpa zea (Boddie) (Lepidoptera:Noctuidae)

Flight-tunnel experiments were conducted using Helicoverpa zea males to determine whether or not (Z)-11-hexadecen-1-ol (Z11-16:OH), a compound emitted by another heliothine moth species, Heliothis subflexa, is a behavioral antagonist when admixed with the two-component pheromone blend of H. zea. Males were less likely to fly upwind all the way to the source when 0.3% Z11-16:OH was present in the blend. Even 0.1% Z11-16:OH caused differences in the flight behavior of H. zea males; they steered more off the windline than males responding to the pheromone blend alone, resulting in more oblique track angles. Thus Z11-16:OH appears to act antagonistically, along with another compound, (Z)-11-hexadecen-1-ol acetate (Z11-16:Ac), when it is added to the H. zea pheromone blend.     

Behavioral and electrophysiological responses of Helicoverpa assulta, H. armigera (Lepidoptera: Noctuidae), their F1 hybrids and backcross progenies to sex pheromone component blends

Two sibling species, Helicoverpa assulta and Helicoverpa armigera both use (Z)-9-hexadecenal and (Z)-11-hexadecenal as their sex pheromone components but in almost reversed ratios, 93:7 and 3:97, respectively. H. assulta and H. armigera males performed upwind flight in response to the H. assulta sex pheromone blend (93:7). H. armigera responded strongly to the H. armigera blend (3:97), whereas H. assulta males remained inactive upon exposure to this blend. Both species gave clear dose-dependent electrophysiological responses to (Z)-11-hexadecenal. However, (Z)-9-hexadecenal evoked strong dose-dependent electrophysiological responses in H. assulta males but not in H. armigera. The two male F₁ hybrids exhibited similar behavioral responses to two sex pheromone blends and electrophysiological responses to two pheromone components as H. armigera males. This indicated that H. armigera genes appear dominant in determining the behavioral response and electrophysiological responses. Behavioral and electrophysiological responses of backcrosses of male F₁ hybrids (H. armigera female × H. assulta male) with female H. assulta and H. armigera were close to that of H. assulta and H. armigera, respectively. However, backcrosses of female F₁ hybrids (H. assulta female × H. armigera male) with male H. assulta and H. armigera showed reduced behavioral responses but normal electrophysiological responses compared to males of the respective parental line.     

Sex pheromone analysis and effective attraction of males of the cabbage webworm,Hellula undalis,inhabiting the Mekong Delta of Vietnam

Hellula undalis is a harmful insect pest of green mustard in the Mekong Delta of Vietnam. In order to establish a tool for a sustainable pest control program, the sex pheromone of H. undalis inhabiting the Mekong Delta was examined. GC-EAD and GC–MS analyses of pheromone gland extracts from the virgin females elucidated three new components, (Z)-11-tetradecenyl acetate (Z11-14:OAc), (Z)-11-hexadecenal (Z11-16:Ald), and (11E,13E)-11,13-hexadecadien-1-ol, in addition to the known pheromone component (11E,13E)-11,13-hexadecadienal (E11,E13-16:Ald). Double bond positions of the two monoenyl components were determined by GC–MS analysis of the pheromone extract treated with dimethyl disulfide. On the other hand, GC–MS analysis of the female body extract detected the unsaturated hydrocarbon (3Z,6Z,9Z)-3,6,9-tricosatriene (Z3,Z6,Z9-23:H). Field examinations of their synthetic compounds indicated the significant role of E11,E13-16:Ald as a major component and a clear synergistic effect of the two monoenyl compounds as a minor component. Although the 3:3:7 mixture of Z11-14:OAc, E11-16:Ald, and E11,E13-16:Ald captured the largest number of males among the tested mixtures, the activity was still quite a bit lower than that of virgin females. However, the 3:3:7:1 mixture, which was prepared by adding a small amount of Z3,Z6,Z9-23:H to the 3:3:7 ternary lure, succeeded in attracting males more powerfully than the females did. This strong synergistic effect was not observed when the triene was added to unmixed E11,E13-16:Ald, indicating important roles of not only the triene but also the two monoenyl compounds as natural pheromone components.     

Terminal fatty-acyl-CoA desaturase involved in sex pheromone biosynthesis in the winter moth (Operophtera brumata)

The winter moth (Operophtera brumata L., Lepidoptera: Geometridae) utilizes a single hydrocarbon, 1,Z3,Z6,Z9-nonadecatetraene, as its sex pheromone. We tested the hypothesis that a fatty acid precursor, Z11,Z14,Z17,19-nonadecanoic acid, is biosynthesized from ??-linolenic acid, through chain elongation by one 2-carbon unit, and subsequent methyl-terminus desaturation. Our results show that labeled ??-linolenic acid is indeed incorporated into the pheromone component in vivo. A fatty-acyl-CoA desaturase gene that we found to be expressed in the abdominal epidermal tissue, the presumed site of biosynthesis for type II pheromones, was characterized and expressed heterologously in a yeast system. The transgenic yeast expressing this insect derived gene could convert Z11,Z14,Z17-eicosatrienoic acid into Z11,Z14,Z17,19-eicosatetraenoic acid. These results provide evidence that a terminal desaturation step is involved in the winter moth pheromone biosynthesis, prior to the decarboxylation.     

Identification of the New Hydrocarbon (Z,Z)-1,6,9-Heptadecatriene as the Secretory Component of Caloglyphus polyphyllae (Astigmata: Acaridae)

A new heptadecatriene was isolated from the acarid mite, Caloglyphus polyphyllae, as the major characteristic component which could be used to identify the species chemo-taxonomically. Its structure was elucidated as 1,6,9-heptadecatriene by partial hydrogenation and a subsequent GC/MS analysis of the dimethyldisulfide derivative, together with evidence of the terminal vinyl group and Z-configuration of double bonds that was provided by GC-FT/IR and NMR. The triene was identified as (Z,Z)-1,6,9-heptadecatriene by its synthesis and is revealed to be a new compound as a natural product.     

Responses of Mamestra suasa male moths to synthetic pheromone compounds in a wind tunnel

The upwind flight and landing responses of male Mamestra suasa (Den. & Schiff.) (Lepidoptera; Noctuidae) to various synthetic chemicals were studied in a wind tunnel. A mixture of (Z)-11-hexadecenyl acetate (Z11-16: Ac) and (Z)-11-hexadecenal (Z11-16: Ald) elicited upwind flight responses past the midpoint of the wind tunnel, and both components were necessary for landing of the males to occur at the pheromone source point. The best response to the mixtures tested was to a ratio 100:1 (ng) of Z11-16: Ac and Z11-16: Ald (blend B).The addition of (Z)-9-tetradecenyl acetate (Z9-14: Ac) (10 ng) to blend B resulted in a significant decrease of upwind flight and landing responses. The inhibitory effect of this chemical when it is mixed with blend B, and the presence of a specific receptor for this compound in sensilla trichodea of male M. suasa, suggest that Z9-14: Ac is involved in the chemical communication between M. suasa and other sympatric species. The addition of (Z)-11-hexadecenol (Z11-16: OH) (1 or 10 ng) to blend B had no effect on male upwind flight and landing responses. This compound does not seem to be involved in the chemical communication of this species.

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Résumé L'observation et la comptabilisation des vols orientés et des atterrissages des mâles de Mamestra suasa (Den. & Schiff.) (Lepidoptera; Noctuidae) sur une source de phéromone de synthèse ont mis en évidence un mélange attractif appelé mélange B et constitué par 100 ng de Z11-16: Ac et 1 ng de Z11-16: Ald. L'attraction et l'atterrissage sont sous la dépendance du mélange de ces 2 composés. Les variations de leurs proportions relatives affectent les différentes phases du comportement de vol des mâles.L'addition de 10 ng d'acétoxy-1 tetradécène-9 Z (Z9-14: Ac) diminue significativement les proportions de vols orientés et d'atterrissages par rapport aux réponses obtenues avec le mélange B seul. L'effet inhibiteur de cette molécule sur l'attractivité du mélange B et la présence chez M. suasa d'un récepteur spécialisé dans la perception de ce composé suggèrent que le Z9-14: Ac est impliqué dans la communication chimique entre M. suasa et d'autres espèces sympatriques. L'addition d'hexadécènol-11 Z (Z11-16: OH) au mélange B à la dose de 1 ou 10 ng ne modifie pas les réponses des mâles. Ce composé ne semble pas impliqué dans la communication chimique chez M. suasa.

     

(Z)-9-tetradecenal: a potent inhibitor of pheromone-mediated communication in the oriental tobacco budworm moth,Helicoverpa assulta

The behavioural significance of (Z)-9-tetradecenal to male H. assulta was tested by comparing the number of moths attracted to lures containing a standard synthetic female sex pheromone with lures in which (Z)-9-tetradecenal was also added. The standard pheromone mixture used contained 1000 g (Z)-9-hexadecenal, 50 g (Z)-11-hexadecenal, 300 g (Z)-9-hexadecenyl acetate and 15 g (Z)-11-hexadecenyl acetate impregnated on rubber septa. Addition of (Z)-9-tetradecenal to the standard pheromone was shown to significantly reduce the caught of male H. assulta when added in amounts greater than 10 g or 1% of the major pheromone component in both field and net-house experiments. The reduction in catch was found to be dependent on the quantity of (Z)-9-tetradecenal added to the standard pheromone. The implications of these results on conspecific and inter-specific pheromone-mediated communication in H. assulta and related sympatric heliothine species is discussed.Abbreviations Z9-16:AL (Z)-9-hexadecenal - Z11-16:AL (Z)-11-hexadecenal - Z9-16:AC (Z)-9-hexadecenyl acetate - Z11-16:AC (Z)-11-hexadecenyl acetate - Z9-14:AL (Z)-9-tetradecenal - Z9-16:OH (Z)-9-hexadecen-1-ol - Z11-16:OH (Z)-11-hexadecen-1-ol - RH relative humidity     

Electroantennagrams of Mexican fruit flies to chemicals produced by males

Male-produced chemicals were tested on antennae of the Mexican fruit fly (Anastrepha ludens) (Diptera: Tephritidae) using the electroantennagram technique. Male and female antennae responded equivalently to six chemicals and combinations of the six chemicals. (S,S)-(-)-epianastrephin elicited responses two-three times greater than any of the other chemicals, (S,S)-(-)-anastrephin gave greater responses than (R,R)-(+)-anastrephin, and Z,Z-3,6-nonadienol gave greater responses than Z-3-nonenol. The combination of Z,Z-3,6-nonadienol and Z-3-nonenol elicited a response which was slightly less than the response to Z,Z-3,6-nonadienol alone. The EAG data were highly correlated with behavioral data from earlier experiments.

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Résumé L'étude des substances émises par les mâles d'A. ludens (Diptera, Tephritidae) comprenant 2 paires énantiomériques de lactones épimériques et 2 alcools, a été réalisée à partir d'électroantennogrammes.Les antennes des mâles et des femelles ont répondu de la même façon aux 6 substances examinées séparément, ou combinées 2 à 2, ou toutes ensembles. La (S,S)-(-) épianastréphine, seule ou en combinaison, a induit une réponse significativement de 2 à 3 fois plus importante que n'importe qu'elle autre substance. La (S,S)-(-) anastréphine a induit des EAG deux fois plus importantes que ceux obtenus avec la (R,R)-(+) anastréphine.L'importance des réponses aux 4 lactones est liée à leurs relations structurales.Le (Z,Z)-3,6 nonadiénol a provoqué des réponses 2 fois plus importantes que celles du (Z)-3 nonénol, et la combinaison des 2 alcools a induit une réponse légèrement inférieure à celle obtenue avec le (Z,Z)-3,6-nonadiénol seul.Les résultats en EAG sont très conformes aux observations comportementales d'expériences précédentes.

     

Field evaluation of female sex pheromone of the artichoke moth, Gortyna xanthenes

Field responses of Gortyna xanthenes (Germar) males to traps baited with different mixtures of the female sex pheromone components were evaluated in an artichoke field. Catches were compared to those obtained by virgin females and light traps. The best results were achieved by utilizing a mixture of 5 mg Z11-16:Ald + 0.15 mg Z9-16:Ald + 0.15 mg 16:Ald + 0.12 mg Z11-16:OH, which captured only G. xanthenes males 3–5 times more than light traps and ca two times more than one virgin female. Starting from the basic mixture Z11-16:Ald (89–92%) + Z9-16:Ald (2–4%), the addition of 16:Ald (2–4%) and of Z11-16:OH (2–3%) produced an increase of G. xanthenes and a decrease of H, armigera (Hb.) catches. The inhibitory action of Z11-16:OH towards H. armigera males was confirmed.

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Evaluation sur le terrain des constituants de la phéromone sexuelle de la noctuelle de l'artichaut (Gortyna xanthenes)

Résumé Dans un champ d'artichaut de la province de Salerno on a evalué la réponse des mâles de G. xanthenes à mélanges divers des constituants de la phéromone sexuelle produite par la femelle. Les meilleurs résultats ont été obtenus en employant un mélange de 5 mg Z11-16:Ald + 0.15 mg Z9-16:Ald + 0.15 mg 16:Ald + 0.12 mg Z11-16:OH, qui a capturé seulement les mâles de G. xanthenes en mesure 3–5 fois plus élevée que les pièges lumineux et ca. deux fois plus élevée que la femelle vierge. En partant du mélange base Z11-16:Ald (89–92%) + Z9-16:Ald (2–4%), l'addition de 16:Ald (2–4%) et de Z11-16:OH (2–3%) a causé un accroissement des captures de G. xanthenes et une diminution des captures de Heliothis armigera. Cela confirme l'action inhibitoire du Z11-16:OH à l'égard des males de H. armigera.

     

Sex attractants for Pexicopia malvella and Platyedra subcinerea, pests of malvaceous ornamentals and cotton

Pexicopia malvella (Hbn.) males were attracted to mixtures containing (Z,E)-7,11-hexadecadienyl acetate and (Z,Z)-7,11-hexadecadienyl acetate, in screening tests, in Hungary. An approximate dose of 40 g 5:1 ZE:ZZ mixture is recommended for practical use as a selective and potent sex attractant. Platyedra subcinerea (Hw.), another gelechiid pest, was attracted best to a 300 g dose of (Z,Z)-7,11-hexadecadienyl acetate.

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Zusammenfassung Die binäre Mischung von (Z,Z)-7,11-hexadekadienylacetat und (Z,E)-7,11-hexadekadienylacetat erwies sich im Freiland als Sexuallockstoff für Männchen von P. malvella (Gelechiidae, Lepidoptera). Die Verhältnisse 1:1, 1:1.4, 1:2.5, 1:5 und 1:10 lockten bedeutende Anzahlen von Männchen, die Komponenten allein waren unwirksam. Die Mischung in Verhältnis 1:5 und bei der Köderbeladung von ungefähr 40 g kann zur praktischen Anwendung als ein spezifisches und effektives Lockstoff empfehlt werden.Männchen von P. subcinerea (= vilella Gelechiidae, Lepidoptera) wurden zu Fallen mit dem Isomer (Z,Z) angelockt. Beste Fangergebnisse wurden mit der Köderbeladung 300 g (Z,Z)-7,11-hexadekadienylacetat erreicht. P. malvella wird in Ungarn als bedeutungsvoller Schädling von Zierpflanzen der Familie Malvaceae gemeldet, und alle beide Arten sind als Baumwolleschädlinge in zentralasiatischen Sovietrepubliken und anderen Ländern in Asien bekannt.

     

Field evaluation of female sex pheromone components of the cotton bollworm,Heliothis armigera

(Z)-11-hexadecenal and (Z)-9-hexadecenal were ineffective lures forH. armigera males unless combined. Attraction depended upon perception of a 90%–99% combination of (Z)-11-hexadecenal with 1%–10% (Z)-9-hexadecenal. Increasing the level of (Z)-9-hexadecenal in the mixture to 26.2% reduced catches. Adding 2.3% (Z)-7-hexadecenal to the mixture did not enhance or reduce attraction, while adding 8.7% (Z)-11-hexadecenol significantly reduced male catches. The combination of (Z)-11-hexadecenal and (Z)-9-hexadecenal was effective only when released from rubber dispensers but not from polyethylene vials. A load of 2 mg of the mixture on rubber dispensers effectively attracted males for at least 31 days. TheH. zea lure which contained all the pheromonal components of that species was also effective in attractingH. armigera males. TheH. virescens lure attracted significantly fewerH. armigera males than theH. zea lure.

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Résumé Les (Z)-11-hexadecenal et (Z)-9-hexadecenal sont des attractifs sexuels in efficaces pour les mâles deH. armigera. L'attraction dépend de la perception d'un mélange de 90 à 99% de (Z)-11-hexadecenal avec 1 à 10% (Z)-9-hexadecenal, L'augmentation jusqu'à 26,2% de la teneur en (Z)-9-hexadecenal réduit les captures. L'addition de 2,3% de (Z)-7-hexadecenal au mélange ne modifie pas l'attractivité, tandis que celle de 8,7% de (Z)-11-hexadecenol, réduit significativement les captures de mâles. Le mêlange de (Z)-11-hexadecenal et de (Z)-9-hexadecenal n'a été efficace qu'avec des diffuseurs en caoutchouc, par contre il a été sans effet à partir de récipients de polyéthylène. Une charge de 2 mg de mélange dans des diffuseurs en caoutchouc attire effectivement les mâles pendant ou moins 31 jours. L'attractif sexuel deH. zea qui contient tous les constituants de la phéromone de cette espèce attire aussi efficacement les mâles deH. armigera. Celui deH. virescens attire significativement moins de mâles deH. armigera que l'attractif sexuel deH. zea.

     

Facile syntheses for (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-nonadecadienoic acid, and (5Z,9Z)-5,9-eicosadienoic acid through a common synthetic route

The delta 5,9 fatty acids (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-nonadecadienoic acid, and (5Z,9Z)-5,9-eicosadienoic acid were synthesized for the first time in four steps (9-12% overall yield) starting from commercially available 2-(2-bromoethyl)-1,3-dioxolane. The synthetic approach provided enough material to corroborate the structure and stereochemistry of (5Z,9Z)-5,9-nonadecadienoic acid which was recently identified in the flowers of Malvaviscus arboreus (Malvaceae). The novel phospholipids 1-hexadecanoyl-2-[(5Z,9Z)-5,9-eicosadienoyl]-sn-glycer o-3-phosphocholine and 1-octadecanoyl-2-[(5Z,9Z)-5,9-eicosadienoyl]-sn- glycero-3-phosphocholine were also synthesized from commercially available L-alpha-phosphatidylcholine (egg yolk) and characterized by positive ion electrospray mass spectrometry. These are the first examples of unsymmetrical phospholipids with saturated fatty acids at the sn-1 position and delta 5,9 fatty acids at the sn-2 position.