Sex pheromone of fall armyworm,Spodoptera frugiperda (J.E. Smith)

Analyses of extracts of pheromone glands and of volatiles from calling female fall armyworm moths,Spodoptera frugiperda (J.E. Smith), revealed the presence of the following compounds: dodecan-1-ol acetate, (Z)-7-dodecen-1-ol acetate, 11-dodecen-1-ol acetate, (Z)-9-tetradecenal, (Z)-9-tetradecen-1-ol acetate, (Z)-11-hexadecenal, and (Z)-11-hexadecen-1-ol acetate. The volatiles emitted by calling females differed from the gland extract in that the two aldehydes were absent. Field tests were conducted with sticky traps baited with rubber septa formulated to release blends with the same component ratios as those emitted by calling females. These tests demonstrated that both (Z)-7-dodecen-1-ol acetate and (Z)-9-tetradecen-1-ol acetate are required for optimum activity and that this blend is a significantly better lure than either virgin females or 25 mg of (Z)-9-dodecen-1-ol acetate in a polyethylene vial, the previously used standard. Addition of the other three acetates found in the volatiles did not significantly increase the effectiveness of the two-component blend as a bait for Pherocon 1C or International Pheromones moth traps.Mention of a commercial or proprietary product does not constitute an endorsement by the USDA.     

Heliothis virescens: Attraction of males to blends of (Z)-9-tetradecen-1-ol formate and (Z)-9-tetradecenal

In field trapping experiments, 161 and 321 blends of (Z)-9-tetradecen-1-ol formate (Z-9-TDF) and (Z)-9-tetradecenal (Z-9-TDAL) caught as manyHeliothis virescens (F.) as 3 virgin females and virelure, the synthetic pheromone of this species [a 161 mixture of (Z)-11-hexadecenal (Z-11-HDAL) and (Z)-9-tetradecenal]. Z-9-TDF and (Z)-7-dodecen-1-ol formate (Z-7-DDF) are structurally similar to Z-11-HDAL and Z-9-TDAL, respectively. The sensory input elicited by Z-9-TDF appears to substitute for the sensory input of Z-1 1-HDAL. In contrast, Z-7-DDF had no significant effect on catches of maleH. virescens when used alone, in combination with either Z-11-HDAL or Z-9-TDF as a bait in traps, or as a disruptant of pheromone communication via permeation of the atmosphere. Furthermore, Z-9-TDF may be a more stable and economical attractant forH, virescens males than is Z-1 1-HDAL.This paper reports the results of research only. Mention of a pesticide in this paper does not constitute a recommendation for use by the U.S. Department of Agriculture nor does it imply registration under FIFRA as amended. Also, mention of a commercial or proprietary product in this paper does not constitute a recommendation or an endorsement of that product by the USDA.     

Sex pheromone of the cranberry girdler,Chrysoteuchia topiaria (Zeller) (Lepidoptera: Pyralidae)

Z-11-Hexadecen-1-al (Z11-16A1), free of theE isomer, was identified in extracts of femaleChrysoteuchia topiaria (Zeller) abdominal tips. In commercial grass seed fields, traps baited with synthetic Z11-16A1 were almost as attractive as female-baited traps. An alcohol, thought to be Z-11-hexadecen-1-ol on the basis of gas Chromatographic retention times, was also isolated from the extract.     

Identification and Field Evaluation of Components of Female Sex Pheromone of Millet Stem Borer, Coniesta ignefusalis

Five active compounds were detected during analyses of ovipositor washings and effluvia from virgin female Coniesta ignefusalis moths by gas chromatography (GC) linked to electroantennographic (EAG) recording from a male moth. These were identified as (Z)-7-dodecen-1-ol (Z7–12:OH), (Z)-5-decen-1-ol (Z5–10:OH), (Z)-7-dodecenal (Z7–12:Ald), (Z)-7-dodecenyl acetate (Z7–12:Ac), and (Z)-9-tetradecen-1-ol (Z9–14:OH) by comparison of their GC retention times, mass spectra, and EAG activities with those of synthetic standards. Laboratory tests of dispensers for these compounds showed that release rates from polyethylene vials increased to relatively uniform values after three to four days, but release from septa was very rapid and nonuniform and decreased to low levels after two to three days. Trapping tests in Niger showed that the major component, Z7–12:OH, and two of the minor components, Z5–10:OH and Z7–12:Ald, were essential for attraction of male C. ignefusalis moths. The most attractive blend contained these three components in a 100:5:3.3 ratio in a polyethylene vial, which emitted the components in similar proportions to those produced by the female C. ignefusalis moth. Water traps baited with this blend containing 1 mg of Z7–12:OH caught more male C. ignefusalis moths than traps baited with newly emerged female moths. Addition of up to 10% of the corresponding E isomers of the pheromone components had no effect on catches, but addition of the other two minor components detected, Z7–12:Ac and/or Z9–14:OH, to the attractive blend at naturally occurring levels caused significant reductions in trap catch.     

2-(E)-nonen-1-ol: Male attractant for chafersAnomala vitis Fabr. andA. dubia Scop. (Coleoptera: Scarabaeidae)

Traps baited with 2-(E)-nonen-1-ol alone or in combination with other compounds caught large numbers of males of both the vine chafer,Anomala vitis Fabr. and the margined vine chafer,A. dubia Scop. (Coleoptera: Scarabaeidae), vineyard and orchard pests. In a dosage test, the largest numbers were caught by traps baited with 10 mg of 2-(E)-nonen-1-ol, which was the highest dosage tested. This is the first report on male attractants for chafer species occurring in Europe.The present paper is dedicated to the memory of our coauthor, friend and colleague Mátyás Lesznyák who died a premature and tragic death in late 1993.     

Sex pheromone of the avocado pest,Amorbia cuneana (Walsingham) (Lepidoptera: Tortricidae)

The major volatile components in the extract of the female sex pheromone gland ofAmorbia cuneana consisted of (E,E)- and (E,Z)-10,12-tetradecadien-1-ol acetates. The identification was based on electroantennogram bioassay of gas Chromatographic effluent from sex pheromone gland extract, relative retention times on polar and nonpolar gas chromatographic columns, chemical degradation (ozonolysis, saponification), mass spectrometry, chemical synthetic methods, and field tests. Based on mass spectrometry and retention times by capillary gas chromatography, traces of (E)-10-tetradecen-1-ol acetate and 1-tetradecanol acetate were also present in the extract. Traps baited with a combination of synthetic (E,E)- and (E,Z)-10,12-tetradecadien-1-ol acetates caught more males than did traps baited with females.This paper reports the results of research only. Mention of a commercial product in this paper does not constitute a recommendation by the U.S. Department of Agriculture.     

SEX PHEROMONE COMPONENTS OF THE SANDTHORN CARPENTERWORM, <Emphasis Type="Italic">Holcocerus hippophaecolus</Emphasis>

Extracts of female sex pheromone gland of the carpenterworm moth, Holcocerus hippophaecolus Hua, a pest of sandthorn, Hippophae rhamnoides L. were found to contain (E)-3-tetradecenyl acetate (E3-14:Ac), (Z)-3-tetradecenyl acetate (Z3-14:Ac), (Z)-7-tetradecenyl acetate (Z7-14:Ac), the corresponding alcohols, E3-14:OH, Z3-14:OH, Z7-14:OH, and (E)-9-tetradecenyl acetate (E9-14:Ac). Electroantennographic (EAG) analysis of these chemicals and their analogs demonstrated that Z7-14:Ac elicited the largest male EAG response, followed by E3-14:Ac. In field trials, traps baited with either Z7-14:Ac or E3-14:Ac alone caught no male moths, whereas a combination of these two components in a 1:1 ratio caught more males than control traps. Addition of Z7-14:OH and Z3-14:OH or the alcohols plus E9-14:Ac did not enhance trap catches. We conclude that the sex pheromone of H. hippophaecolusis composed of Z7-14:Ac and E3-14:Ac. Optimal ratios and doses of these two components, and the possible role of other minor components, remain to be determined.     

(Z)-9-tetradecen-1-ol acetate

(Z)-9-Tetradecen-1-ol acetate [(Z)-9-TDA], identified originally as the sex pheromone of the fall armyworm,Spodoptera frugiperda (J.E. Smith), acted as a secondary sex pheromone when it was tested in sticky traps in field tests. Low-level synergism was obtained when 2 and 10% quantities of (Z)-9-TDA were added to 100 g of (Z)-9-dodecen-1-ol acetate, which is now considered the primary sex pheromone.Lepidoptera: Noctuidae.In cooperation with the University of Georgia College of Agriculture Experiment Stations, Coastal Plain Station, Tifton, Georgia 31794.Mention of a proprietary product does not constitute endorsement by the USDA.     

Identification of male cabbage looper sex pheromone attractive to females

A multicomponent pheromone produced by male cabbage looper moths that is attractive to female moths in a flight tunnel bioassay was isolated and identified. Based on analyses of hairpencil extracts of male cabbage loopers and volatiles emitted by males, the pheromone has been identified as a blend consisting of (S)-(+)-linalool,p-cresol, andm-cresol. The chirality of the major component, (S)-(+)-linalool, is important for behavioral response of females. These pheromonal compounds were also identified as volatiles released by males when males were exposed to the principal pheromone component of female cabbage loopers, (Z)-7-dodecen-1-ol acetate. The amount of male pheromone released was increased significantly when males were exposed to a combination of (Z)-7-dodecen-1-ol acetate and the odor from cabbage. Neither linalool nor the cresols were detected in volatiles from cabbage or from males exposed to cabbage odor.     

Comparing the effectiveness of sexual communication disruption in the oriental fruit moth (Grapholitha molesta) using different combinations and dosages of its pheromone blend

The relative efficacy of disruptant blends comprised of different combinations of the Oriental fruit moth's pheromone components was determined in field tests. Disruption was evaluated by comparing male moth catch at synthetic and female-baited traps in disruptant and non-treatment areas. Three atmospheric dosages of a 8-dodecenyl acetate (93.5%Z6.5%E) blend, representing two successive 10-fold decreases in concentration (2.5 × 10^–2 g/hectare/day to 2.5 × 10^–4 g/hectare/day) were tested alone and in combination with an additional percentage of (Z)-8-dodecen-1-ol. Male moth orientation to traps was eliminated in plots exposed to the two highest binary acetate dosages. However, significantly more males were captured in synthetic-baited traps in the lowest acetate-alone treatment, indicating a diminution of disruption efficiency. In contrast, inclusion of (Z)-8-dodecen-1-ol in the disruptant blend effected essentially complete disruption of orientation at all concentrations tested. Mating success ofG. molesta pairs confined in small cages apparently was not affected by the presence of relatively high concentrations of the binary acetate and the acetate-alcohol blends. This suggests that habituation and/or adaptation of male response, at least for comparatively close-range behaviors, did not occur.Lepidoptera: Tortricidae.Published as Journal Article No. 9569 of the Michigan Agricultural Experiment Station.     

Role of female-produced sex pheromone in behavioral reproductive isolation betweenTrichoplusia ni (Hübner) andPseudoplusia includens (Walker) (Lepidoptera: Noctuidae,plusiinae)

In laboratory flight tunnel bioassays, response rates of male cabbage looper,Trichoplusia ni (Hübner), to female soybean looper,Pseudoplusia includens (Walker), were similar to response rates of maleT. ni to conspecific females for plume tracking and source contact. Male soybean loopers, however, exhibited a greatly reduced response to female cabbage loopers compared to conspecific females. Similar differences were observed in male responses to extracts of female abdominal tips. Studies of flight tunnel responses of male soybean loopers to the different chemicals known to be components of the female cabbage looper sex pheromone indicated that the reduction in response was due to inhibitory effects of (Z)-5-dodecen-1-ol acetate and (Z)-9-tetradecen-1-ol acetate, when added singly to (Z)-7-dodecen-1-ol acetate (major component of both species) at release rates and at ratios close to those observed in female cabbage loopers.     

Sex attractant for three species of the genusOncocnemis: O. chandleri (Grt.),O. cibalis (Grt.), andO. mackiei (B. & Benj.) (Lepidoptera: Noctuidae)

Oncocnemis chandleri, O. cibalis, andO. mackiei were attracted to chemically baited traps in the field. In all three cases, (5E,7Z)-dodecadienyl acetate was a key component for attraction. Attraction ofO. chandleri to traps baited with the (5E,7Z)-dodecadienyl acetate was inhibited by addition of (Z)-7-dodecenyl acetate.O. cibalis required both (5E,7Z)-dodecadienyl acetate and (Z)-7-dodecenyl acetate for attraction. Electroantennogram responses for the three species are also reported.     

Controlled release plastic strips containing (Z)-9-dodecen-1-ol acetate for attractingSpodoptera frugiperda

Laminated plastic strips and polyethylene vials used for dispensing (Z)-9-dodecen-1-ol acetate attracted maleSpodoptera frugiperda (J.E. Smith) in similar numbers for comparable periods. Addition of an antioxidant to the pheromone dispensed from the polyethylene vials did not significantly increase the period of effectiveness. The laminated plastic strips were acceptable dispensers of pheromone bait for attractingS. frugiperda males to sticky traps in the field.Lepidoptera: Noctuidae.This paper reports the results of research only. Mention of a commercial or proprietary product or of a pesticide in this paper does not constitute a recommendation for use by the U.S. Department of Agriculture, nor does it imply registration under FIFRA as amended.     

Sex pheromone of fall armyworm

Two components of the fall armyworm,Spodoptera frugiperda (J.E. Smith), sex pheromone, (Z)-9-dodecen-1-ol acetate (DDA) and (Z)-9-tetradecen-1-ol (TDA), were tested alone and in combination to determine their effects on male sexual response and inhibition of mating in the laboratory. The threshold response for FAW males was lower for TDA than for DDA, and males responded to TDA over a wider range of dosages. Although TDA is not attractive to FAW males in the field, this compound was highly effective in reducing mating under laboratory conditions.cooperating with the Insect Attractants, Behavior, and Basic Biology Research Laboratory, Gainesville, Florida 32604.     

Attractant lures for males of the pea moth,Cydia nigricana (F.) Containing (E)-10-dodecen-1-yl acetate and (E,E)-8,10-dodecadien-1-yl acetate

Lures containing different amounts of (E)-10-dodecen-1-yl acetate and (E,E)-8, 10-dodecadien-1-yl acetate were formulated in natural rubber stoppers or polyethylene vials and tested in traps in the field to establish relative attractiveness to males of the pea moth,Cydia nigricana (F.), dose-response relationships, and the effects of weathering. Initially, both formulations of (E,E)-8,10-dodecadien-1-yl acetate were much more attractive than those of (E)-10-dodecen-1-yl acetate, but their activity diminished considerably after only 5 days in the field because an inhibitor was formed, and polyethylene formulations were not attractive after one week. However, lures containing (E)-10-dodecen-1-yl acetate, with or without antioxidants, in both rubber and polyethylene were still attractive after three months' exposure in the field and are therefore suitable for practical monitoring of pea moth populations.     

Compounds modifying the activity of two sex attractants for males of the pea moth,Cydia nigricana (F.)

(E)-10-Dodecen-1-yl acetate (E10–12Ac) and (E,E)-8,10-dodecadien-1-ylacetate (E,E8,10–12Ac) are sex attractants for males of the pea moth,Cydia nigricana (F.). Thirty-two structurally related compounds with chain lengths of 9–14 carbon atoms were exposed withE10–12Ac orE,E8,10–12Ac in traps in the field to investigate their influence on the activity of the attractants. Only alchols and acetates unsaturated at C-8, -9, or -10 greatly influenced moth captures. (Z) and (E)-8-dodecen-1-ol were weak synergists forE10–12Ac but no synergists forE,E8,10–12Ac were found. (Z) and (E)-8-dodecen-1-yl acetate and (E,E)-8,10-dodecadien-1-ol inhibited bothE10–12Ac andE,E8,10–12Ac while (E)-10-dodecen-1-ol, 10-dodecyn-1-ol, (Z) and (E)-9-dodecen-1-yl acetate, (Z)-10-dodecen-1-yl acetate, and undecyl acetate inhibited only the former attractant.     

Bioactivity, Synthesis, and Chirality of the Sex Pheromone of Currant Stem Girdler, Janus integer

It was previously reported that females of the currant stem girdler, Janus integer Norton (Hymenoptera: Cephidae), produce a compound, (Z)-9-octadecen-4-olide (1), that is sensitively detected by the antennae of males only. These characteristics suggested a pheromonal function, and this has now been confirmed with behavioral tests. Field tests conducted during two seasons in a commercial red currant field in Washington State showed that synthetic racemic 1 is attractive to male J. integer under natural conditions. A clear dose-response was evident, with greatest numbers of girdlers caught in sticky traps baited with 10 mg of the pheromone (in rubber septa) and least in traps baited with 1 mg or less. During May 2002, 10, 5, 3, and 1 mg baited traps caught means of 41.4, 26.6, 6.7, and 2.7 males/trap/visit (3–5 day intervals), respectively, with a maximum of 229 males caught in a single trap baited with 5 mg. A new synthetic method for racemic 1 is presented. The absolute configuration of natural 1 from the male sawflies was determined to be (R). The potential for using the sex pheromone of J. integer to improve management of this currant and gooseberry pest is discussed.     

Components of the sex pheromone of the female sugar cane borer,Chilo sacchariphagus (Bojer) (Lepidoptera: Pyralidae)

The female sex pheromone of the sugar cane borer,Chilo sacchariphagus, has been shown to contain the two structurally related compounds, (Z)-13-octadecenyl acetate (I) and (Z)-13-octadecen-1-ol (II). These components were detected in female abdominal tip extracts by gas-liquid chromatography (GLC) combined with electroantennography (EAG), and were identified by their GLC behavior, microozonolysis, and interconversion, and by comparison of natural and synthetic material. Field tests in Mauritius showed that traps baited with components I and II combined in ratios from 11 to 91 caught maleC. sacchariphagus moths, and that the 71 ratio was comparable in performance with a virgin female moth. Neither component presented separately in traps caught significant numbers of moths.     

Isolation and identification of sex pheromone ofSymmetrischema tangolias (Gyen) (Lepidoptera: Gelechiidae)

The sex pheromone of the South American potato tuber mothSymmetrischema tangolias (syn.:Symmetrischema plaesiosema) was identified as a 2:1 mixture of (E,Z)-3,7-tetradecadien-1-ol acetate and (E)-3-tetradecen-1-ol acetate by means of dual-column GC, EAG, GC-EAD, GC-MS, NMR, and wind-tunnel bioassays. (Z)-5-Tetradecen-1-ol acetate and (Z)-7-tetradecen-1-ol acetate were also identified in the pheromone gland extract. MaleS. tangolias were able to detect these acetates (EAG), but their addition to the two-component sex pheromone did not improve attractiveness. Field trials in Cajamarca and Cusco, Peru, showed that traps baited with the synthetic sex pheromone were able to catch large numbers of maleS. tangolias.     

Looplure efficacy and electrophysiological responses in three plusiinae species

Source concentration differences of (Z)-7-dodecen-1-ol acetate, or looplure, were evaluated for field trapping efficiency and electrophysiological responses with malePseudoplusia includens (Walker),Trichoplusia ni (Hubner) andRachiplusia ou (Guenné) (Lepidoptera: Noctuidae). Sticky traps baited with 1000 g of the lure captured a significantly greater (P < 0.05) number of maleP. includens andT. ni than any other concentration;R. ou males were caught at a greater rate in traps baited with 100 g of looplure, significantly more (P < 0.05) than with 1000 g. Electroantennogram (EAG) studies demonstrated that antennae of maleP. includens have a lower response threshold to looplure than eitherT. ni orR. ou antennae, the latter demonstrating the highest significant threshold of response. No differences in the stimulus-response functions of the three species were detected.Lepidoptera: Noctuidae.