Search

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.

Wheel bugs (Heteroptera: Reduviidae: Harpactorinae: Arilus) are general predators, the females of which have reddish-orange subrectal glands (SGs) that are eversible like the osmeteria in some caterpillars. The rancid odor of Arilus and other reduviids actually comes from Brindley's glands, which in the North (A. cristatus) and South (A. carinatus) American wheel bugs studied emit similar blends of 2-methylpropanoic, butanoic, 3-methylbutanoic, and 2-methylbutanoic acids. The Arilus SG secretions studied here are absolutely species specific. The volatile SG components of A. carinatus include (E)-2-octenal, (E)-2-nonenal, (E)-2-decenal, (E,E)-2,4-nonadienal, (E)-2-undecenal, hexanoic acid, 4-oxo-nonanal, (E,E)-2,4-decadienal, (E,Z)-2,4- or (Z,E)-2,4-decadienal, and 4-oxo-(E)-2-nonenal; whereas in A. cristatus the SG secretion contains β-pinene, limonene, terpinolene, terpinen-4-ol, thymol methyl ether, α-terpineol, bornyl acetate, methyl eugenol, β-caryophyllene, caryophyllene oxide, and farnesol. Arilus spp. SG secretions may be sex pheromones, but verification of this hypothesis requires further testing.

Dried male inflorescences of breadfruit ( Artocarpus altilis , Moraceae) are burned in communities throughout Oceania to repel flying insects, including mosquitoes. This study was conducted to identify chemicals responsible for mosquito deterrence. Various crude extracts were evaluated, and the most active, the hydrodistillate, was used for bioassay-guided fractionation. The hydrodistillate and all fractions displayed significant deterrent activity. Exploratory GC-MS analysis revealed more than 100 distinctive peaks, and more than 30 compounds were putatively identified, including a mixture of terpenes, aldehydes, fatty acids, and aromatics. A systematic bioassay-directed study using adult Aedes aegypti females identified capric, undecanoic, and lauric acid as primary deterrent constituents. A synthetic mixture of fatty acids present in the most active fraction and individual fatty acids were all significantly more active than N,N-diethyl-m-toluamide (DEET). These results provide support for this traditional practice and indicate the potential of male breadfruit flowers and fatty acids as mosquito repellents.

Several lines of evidence suggest that insect repellent molecules reduce mosquito-host contacts by interacting with odorants and odorant receptors (ORs), thereby ultimately affecting olfactory-driven behaviours. We describe the molecular effects of 10 insect repellents and a pyrethroid insecticide with known repellent activity on two highly specific Aedes aegypti (Diptera: Culicidae) ORs, AaOR2 + AaOR7 and AaOR8 + AaOR7, exquisitely sensitive to key mosquito attractants indole and (R)-(-)-1-octen-3-ol, expressed in oocytes of Xenopus (Anura: Pipidae). Our study demonstrates that insect repellents can both inhibit odorant-evoked currents mediated by ORs and independently elicit currents in the absence of odorants. All of the repellents had effects on one or both ORs; most of these compounds were selective inhibitors and showed a high degree of specificity in their capacity to activate the two ORs. These results show that a range of insect repellents belonging to structurally diverse chemical classes modulate the function of mosquito ORs through multiple molecular mechanisms.

An investigation of the biological effect of catnip oil (Nepeta cataria L.) on the behavioral response of field collected Aedes aegypti and Anopheles harrisoni was conducted using an automated excitorepellency test system. Aedes aegypti showed significantly higher escape rates from the contact chamber at 5% catnip oil compared to other concentrations (P < 0.05). With Anopheles harrisoni, a high escape response was seen at 2.5% catnip oil from the contact chamber, while in the noncontact chamber a higher escape response was observed at a concentration of 5%. Results showed that this compound exhibits both irritant and repellent actions.

Field-collected female goldeneyed lacewing (Chrysopa oculata) strongly avoided ovipositing on substrates exposed over 24 h to three of four lady beetle species tested, resulting in circa 3-fold higher egg deposition on control versus coccinellid-exposed substrates. The effect was stage-specific for Coleomegilla maculata; it was observed for adult and third-instar larvae but not for unfed first-instar larvae.

Gas chromatographic-electroantennographic detection (GC-EAD) analysis showed that male antennae of the green lacewing, Chrysopa nigricornis Burmeister, the most common lacewing species in the U.S. Pacific Northwest, consistently responded to two compounds in thoracic extracts of conspecific males: 1-tridecene and (1R,2S,5R,8R)-iridodial. These compounds were not detected in extracts of the abdominal cuticle, and no other antennally active compounds were found in the abdominal samples. In field-trapping experiments, traps baited with iridodial significantly attracted large numbers of C. nigricornis males (both western and eastern forms) during summer and early fall, plus a few individuals of conspecific females only in early fall. Iridodial also attracted males of the goldeneyed lacewing, C. oculata Say, and, to a lesser extent, C. coloradensis Banks males. Methyl salicylate (MS), reported as an attractant for both sexes of C. nigricornis and C. oculata, was inactive by itself at the concentration tested in our study, but in a few instances slightly enhanced the responses of Chrysopa spp. to iridodial. However, MS alone and its binary blend with iridodial seemed to attract the hoverfly, Metasyrphus americanus (Weidemann). 2-Phenylethanol, a reported attractant for another lacewing, Chrysoperla plorabunda (Fitch) [=carnea (Say)], did not capture any lacewings. Our assays indicated that the lacewing pheromone, iridodial, loaded onto either rubber septa or as a binary blend with MS in polyethylene bags could last at least 5 wk in the field during the summer season. Based on this study, a new attractant system for green lacewings is being developed for both domestic and international markets.

The newly invasive soybean aphid, Aphis glycines Matsumura, has seriously threatened soybean production in North America, after having spread to 20 states in the United States and several southern provinces of Canada. Control ofA.glycines has focused on applications of insecticides, which are not a long-term solution to soybean aphid pest management. In autumn, soybean aphids start producing alate females (gynoparae) that search for their overwintering host plants, the common buckthorn, Rhamnus cathartica. The gynoparae then produce pheromone-emitting wingless female offspring (oviparae) that attract male aphids. In this study, we report the chemical identiÞcation of the soybean aphid sex pheromone using gas chromatographyÐ electroantennogram, gas chromatog- raphyÐmass spectrometry, and nuclear magnetic resonance spectroscopy. Behavioral activities of males and gynoparous females in the Þeld were also characterized. The potential applications using formulations containing speciÞc soybean aphid pheromone compositions for reducing overwintering populations are discussed.

The semiochemical cues used by geographically isolated strains of the parasitoid, Telenomus podisi (Ashmed), to find eggs of the stink bug Euschistus heros were investigated. Two strains of Te. podisi, maintained on eggs of a South American host (E. heros) were studied. One parasitoid strain originated from specimens collected near Brasilia, Brazil (SA strain), and a second strain originated from specimens collected at Beltsville, Maryland (NA strain). Cold tolerance tests of adults from the NA and SA Te. podisi strains, analyses of the cuticular hydrocarbons between the two strains, and crossing experiments between strains each indicated consistent differences between the NA and SA strains. Subsequent experiments using E. heros showed that SA Te. podisi females specifically recognize traces left on the substrate by walking E. heros females and then search intensively the area of the ‘footprints’, apparently looking for an egg mass to parasitize. By contrast, Te. podisi females of the NA strain are incapable of recognizing the footprints of E. heros females despite the fact that these parasitoids were reared from eggs of E. heros. The possibility that the two strains are actually different species is discussed.

Synthetic (1R,2S,5R,8R)-iridodial, the key pheromone component of many green lacewings in the genus Chrysopa, strongly attracted adult males and females of the North American antlion, Dendroleon speciosus Banks. In addition, one of the common sex pheromone components of many aphids to which Chrysopa spp. are weakly attracted, Z,E-nepetalactol, was also weakly attractive to D. speciosus adults. Iridodial and Z,E-nepetalactol also elicited strong and weak electroantennogram detector (EAD) responses, respectively, in D. speciosus adults. Previously reported semiochemicals from European and Israeli antlion species did not elicit EAD or behavioral responses from D. speciosus adults. The earlier studied antlions release volatile chemicals from male-specific metathoracic glands associated with structures on the hind wings (Eltringham’s organs) that are thought to enhance evaporation of the secretion. Although D. speciosus males have Eltringham’s organs similar to those of other antlion species, we discovered that D. speciosus males have a pair of white tubular glands that extend posteriorly into the abdomen, opening in the resting pits of the Eltringham’s organs. Further gas chromatograph (GC)-EAD analysis of another commercially available antlion species, Myrmeleon crudelis Walker, showed that this species did not respond to the lacewing or aphid related volatile compounds, but strongly responded to the reported antlion semiochemicals, namely, nerol, 10-homonerol and nerol oxide. The male-specific abdominal glands of D. speciosus are presumably pheromone glands; hopefully, positive verification of this supposition will help clarify the semiochemical relationships between antlions, lacewings and aphids.

The banana-spotting bug,Amblypelta lutescens lutescensDistant (Heteroptera: Coreidae), is one of the principal pests of tree fruits and nuts across northern and eastern Australia. Apart from visual damage assessment, there are currently no reliable methods for monitoring bug activity to aid management decisions. An attractant pheromone for this species that could be used as a trap lure could potentially fill this void. Earlier, two male-specific compounds were identified in airborne extracts fromA. lutescens lutescens, (E,E)-α-farnesene and (R,E)-nerolidol; an unknown compound with a molecular weight 220 was also detected. We now report the identification of this hitherto unknown compound as (R,E,E)-α-farnesene-10,11-oxide. Synthesis of this epoxide was conducted using a regioselective asymmetric dihydroxylation of a sulfolene. A blend mimicking the natural proportions of (E,E)-α-farnesene, (R,E)-nerolidol, and (R,E,E)-α-farnesene-10,11-oxide attracted male and femaleA. lutescens lutescensas well as nymphs in the field, verifying that the aggregation pheromone comprises or is contained within this group of compounds.

Adult chrysopids have paired prothoracic glands (PG) that are thought to produce defensive secretions (allomones). We analyzed PG extracts of the following green lacewings from North and South America, Australia, and China: Ceraeochrysa cubana (Brazil); Chrysopa (= Co.) oculata, Co. nigricornis, Co. incompleta, Co. quadripunctata (USA), and Co. septempunctata (China); Chrysoperla (= Cl.) rufilabris (USA) and Cl. sp. (Brazil); Plesiochrysa ramburi and Mallada spp. (Australia). PG secretions are characteristic for species within a genus, except for Chrysopa spp. (Z)-4-Tridecene is ubiquitous, but (Z,Z)-4,7-tridecadiene is a major PG constituent in some Chrysopa spp. and in P. ramburi. Earlier reports that Co. oculata and Co. nigricornis produce 1-tridecene were shown to be in error. Chrysopa PG secretions are distinguished by the presence or absence of N-3-methylbutylacetamide, plus skatole (3-methylindole). Skatole is also identified for the first time from the Plesiochrysa and Ceraeochrysa. The PG secretion in Plesiochrysa ramburi is characterized by the presence of (Z)-4-undecene instead of (Z)-4-tridecene, and N-3-methylbutylpropanamide instead of the acetamide, resembling the PG secretions of Chrysopa nigricornis, Co. septempunctata and Co. incompleta. The chemotaxonomic value of PG semiochemicals is discussed, including evidence for subgroups within the genus Chrysopa as it now stands.

Davanone, a key sesquiterpene component of davana oil, has been synthesized in five convenient steps. Oxygenated sesquiterpenes have been linked to insect deterrent properties. Based on initial screening of davana oil, davanone and its hydroxy precursors have been generated and are being evaluated as arthropod deterrents against disease vectors.

The lacewing Chrysopa septempunctata Wesmael is an important, common predator of several insects in China, Japan, Russia, and many parts of Europe. Our field trapping experiments in northeast China showed that males of this green lacewing are strongly attracted to the lacewing pheromone of Chrysopa oculata Say, (1R,2S,5R,8R)-iridodial. The induced plant volatile, methyl salicylate, was unattractive to C. septempunctata by itself at the concentration tested, but synergistic when combined with iridodial where the lacewing population was high. (1R,4aS,7S,7aR)-Nepetalactol and (4aS,7S,7aR)-nepetalactone (aphid sex pheromone components) caught significantly more males of C. septempunctata than did blank control traps, but were inferior to iridodial dispensers, which remained strongly attractive to C. septempunctata males for at least 2.5 months. These results indicate that (1R,2S,5R,8R)-iridodial is a powerful attractant for C. septempunctata, and may have great potential for enhanced biological control of garden, agricultural, and forest insect pests.

Gas chromatographic-electroantennographic detection (GC-EAD) experiments showed that antennae of males and females of the goldeneyed lacewing, Chrysopa oculata Say (Co. = Chrysopa), consistently responded to four compounds extracted from the abdominal cuticle of males: nonanal, nonanol, nonanoic acid, and (1R*,2S*,5R*,8R*)-iridodial. These compounds were not detected from abdominal cuticle of females. Thoracic extracts of both sexes contained antennal-stimulatory 1-tridecene and EAD-inactive skatole. Chrysopa oculata adults were most sensitive to (1R,2S,5R,8R)-iridodial standard at an EAD-response threshold between 0.1 and 1 pg, which was 10–100 times lower than thresholds for nonanal and nonanoic acid, and up to 10,000 times lower than thresholds for other compounds tested. A similar EAD response pattern was also found in another Chrysopa sp. (Co. quadripunctata Burmeister). In field-trapping experiments, (1R,2S,5R,8R)-iridodial was the only male-specific compound that attracted Co. oculata males. Males also were weakly attracted to (1R,4aS,7S,7aR)-nepetalactol (an aphid sex pheromone component), probably due to the 5% (1R,2S,5R,8R)-iridodial present in the synthetic sample as an impurity. A herbivore-induced plant volatile, methyl salicylate, increased attraction of males to (1R,2S,5R,8R)-iridodial, whereas 1-tridecene was antagonistic. No females were caught in the entire study. Scanning electron micrographs revealed numerous male-specific, elliptical epidermal glands on the 3rd–8th abdominal sternites of Co. oculata, which are likely the pheromone glands. Another lacewing species, Chrysoperla rufilabris (Burmeister) (Cl. = Chrysoperla), did not produce male-specific volatiles or possess the type of gland presumed to produce pheromone in Co. oculata males, but (Z)-4-tridecene was identified as a major antennal-stimulatory compound from thoracic extracts of both sexes of Cl. rufilabris. Thus, (1R,2S,5R,8R)-iridodial (or its enantiomer) is now identified as a male-produced male aggregation pheromone for Co. oculata, the first pheromone identified for lacewings.

Enanatiomerically pure 4a S,7 S,7a R and 4a S,7 S,7a S-nepetalactams and their analogs have been prepared in just two steps from 4a S,7 S,7a R and 4a S,7 S,7a S-nepetalactones, major components of catnip oil. Lactams or cyclic amides from iridoid monoterpenes are generated and being evaluated as a new class of compounds as arthropod deterrents against disease vectors.

1R,2S,5R,8R; 1R,2S,5R,8S; 1S,2S,5R,8R; and 1S,2S,5R,8S-Iridodials have been prepared in five steps from 4aS,7S,7aR and 4aS,7S,7aS-nepetalactones, major components of catnip oil. 1R,2S,5R,8R-Iridodial has been identified as a male-produced male-aggregation pheromone for Chrysopa oculata, the first pheromone of any kind identified for lacewings.