(Z)-9-tetradecenal: a potent inhibitor of pheromone-mediated communication in the oriental tobacco budworm moth, Helicoverpa assulta (original) (raw)
Related papers
Entomologia Experimentalis et Applicata, 1993
Three sex pheromonal components, (Z)-ll-hexadecenal (Zll-16:Ald), (Z)-ll-hexadecenol (Zll-16:OH), and hexadecanal (16:Aid), in a ratio of 88.0:7.2:4.8, were identified from ovipositor extracts of the fulvous clover moth, Heliothis maritima Grasl. (Lepidoptera: Noctuidae) by gas chromatographymass spectrometry. In addition, trace amounts of (Z)-9-hexadecenal (Z9-16:AId)were detected in the extracts by GC. A blend of Zll-16:AId, Zll-16:OH and 16:Ald in a ratio of 100:6:3, as well as in combination with 0.1 or 1 part Z9-16:Aid was tested at 0.01, 0.1, 1.0 and 10.0 btg doses in a flight tunnel. In flight tunnel tests male behavioral responses elicited by 0.1 or 1.0 #g doses of the 100:6:3:1 blend were similar to those elicited by an ovipositor extract at 2 female equivalents. Deletion of Z9-16:Ald from the blend at 0.1 #g dose caused a decrease in the male response. In the field test, however, presence or absence of Z9-16:AId did not significantly influence the number of males trapped in sticky traps with rubber septa containing 100/~g of the respective blends.
1999
Flight-tunnel experiments were conducted using Helicoverpa zea males to determine whether or not (Z)-ll-hexadecen-1-01 (211-16 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 % Zll-16'OH was present in the blend Even 0 1% 211-16 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 Zll-16OH appears to act antagonistically, along with another compound, (Z)-ll-hexadecen-1-01 acetate (211-16 Ac), when it is added to the H zea pheromone blend
Journal of Agricultural and Food Chemistry, 2002
Efficient syntheses of (Z,E)-5,7-dodecadienol, a pheromone component of the Siberian moth, Dendrolimus superans sibiricus, and (E,Z)-10,12-hexadecadienol, a pheromone component of various Lepidoptera pheromones, were accomplished by cis reduction of the corresponding enynols with activated zinc. The most energetic reagent was zinc galvanized with copper and silver (Zn/Cu/Ag) that achieved rapid and high-yield reduction in methanol-water. The stereoselectivity of semihydrogenation was g98%. A process whereby zinc dust was continuously activated throughout the reduction with an acid was also satisfactory (95-98% cis). Field evaluation of the 1:1 mixture of (Z,E)-5,7-dodecadienol and (Z,E)-5,7-dodecadienal with the Siberian moth in Russia showed that the rubber septa pretreated with compound and stored at -80°C were as effective as freshly treated septa. Moth responses to septa aged in open air indicated that lure effectiveness declined significantly after 2 weeks of aging. Thus, if rubber septa are used as pheromone dispensers in Siberian moth traps monitoring, they should be replaced biweekly with fresh septa for optimal trap effectiveness.
Studies of the Female Sex Pheromone of the Native Budworm, Heliothis Punctiger
Entomologia Experimentalis et Applicata, 1982
Field screening tests indicated that males of the native budworm, Heliothis punctiger Wallengren (Lepidoptera: Noctuidae) were attracted to a 20:20:1 mixture of (Z)‐11‐hexadecenal (Z11‐16:ALD), (Z)‐11‐hexadecenyl acetate (Z11‐16:Ac) and (Z)‐9‐tetradecenal (Z9‐14:ALD), respectively. Inconsistent results were obtained when the Z11‐16:Ac in the blend was replaced by the corresponding alcohol, (Z)‐11‐hexadecenol (Z11‐16:OH). The presence of Z11‐16:ALD, Z11‐16:Ac and Z11‐16:OH in ovipositor washings from virgin females was confirmed by gas chromatographic (GC) and electroantennographic (EAG) analyses. Despite the field results, there was no evidence of Z9‐14:ALD in the virgin female extracts although this compound would not have been detected at levels below 0.5% of the total pheromone blend.RÉSUMÉÉtude de la phéromone sexuelle des femelles d‘Heliothis punctigerDes études de terrain sur l'attraction des mâles d'Heliothis punctiger (Wallengren) par des substances chimiques montren...
Communication disruption of male Agrotis segetum moths with one or several sex pheromone components
Entomologia Experimentalis et Applicata, 1995
Attraction of male Agrotis segetum Dennis & Schiffermtiller (Lepidoptera: Noctuidae) to sex pheromone traps in fields, which were treated with one or three pheromone components was investigated. Small plots of 1/4 ha size were treated with synthetic pheromone, released by 25 evenly dispersed latex rubber tube dispensers. The dispensers were loaded with either 500 #g Z5-10:OAc (50 mg/ha), or 1000/zg Z7-12:OAc (100 mg/ha), or a 3-component mixture consisting of 500 #g Z5-10:OAc + 1000 #g Z7-12:OAc + 1000 #g Z9-14:OAc. Pheromone traps were placed both within and outside of the treated area in a cross design, with an intertrap spacing of 15 m. Release rates from disruption dispensers were measured in the laboratory after being exposed in the field. The release rates of the components were estimated to be 0.44, 0.11, and 0.06/~g/h/dispenser for Z5-10:OAc, Z7-12:OAc and Z9-14:OAc, respectively. The highest effect of disruption was achieved by the three-component blend, resulting in a significant suppression of trap catches extending 5 m outside of the treated area. The Z5-10:OAc treatment resulted in reduced trap catches inside the treated area, but the effect did not extend outside. Z7-12:OAc alone did not result in any significant reduction in trap catch. The results indicate that different mechanisms may explain the disruptive effect of the treatments and that the single pheromone components are not as effective as the three-component blend.
Journal of Chemical Ecology, 2007
The flight-tunnel response of male Z-strain European corn borer moths (ECB), Ostrinia nubilalis, from a population in New York State (USA), was significantly antagonized by addition of 1% (Z)-11-hexadecanal (Z11-16:Ald) to their sex pheromone (a 97:3 mix of (Z)-and (E)-11-tetradecenyl acetate [Z/E11-14:OAc]). The level of antagonism was equivalent to that observed for the previously identified ECB antagonist, (Z)-9-tetradecenyl acetate (Z9-14:OAc), and supports a recent report showing that Z11-16:Ald, a minor pheromone component of the Noctuid moth, Sesamia nonagrioides, caused antagonism of ECB pheromone communication in sympatric populations in the Iberian Peninsula. Singlesensillum recordings from ECB antennae, which included cross-adaptation experiments, showed that the same olfactory receptor neuron processing Z9-14:OAc inputs was responsible for detecting Z11-16:Ald, and that this neuron was not responsive to two other aldehydes, (Z)-9-tetradecanal (Z9-14:Ald) and (Z)-9-hexadecanal (Z9-16:Ald), found in other moth sex pheromones. Our results show that the antagonism is not confined to one geographic region, is specific for Z11-16:Ald, and that antagonist pathways might have the potential for processing a number of structurally similar compounds.
New Zealand Plant Protection, 2018
Epiphyas postvittana is a major horticultural pest in many countries, including New Zealand. Recently, two minor components (E)-11-tetradecen-1-ol and (E)-11-hexadecenyl acetate were found to increase the attraction of a previously identified two-component sex pheromone (95:5 blend of (E)-11-tetradecenyl acetate [E11-14:Ac] and (E,E)-9,11-tetradecadienyl acetate [E9,E11-14:Ac]) of Epiphyas postvittana. We hypothesised that the interaction between these minor components and the behavioural antagonist (Z)-11-tetradecenyl acetate (Z11-14:Ac) would modulate its antagonistic effect. The effect of increasing the ratio (0.5—10%) of Z11-14:Ac was tested in traps baited with E11-14:Ac and E9,E11-14:Ac (95:5), with or without the addition of the two minor compounds. Catch decreased as the percentage of Z11-14:Ac increased (χ2=108.74; d.f.=9;…
Journal of Pesticide Science, 2008
Ald), which has been identified from female moths of the citrus leafminer (Phyllocnistis citrella, Lepidoptera: Gracillariidae), strongly attracts conspecific males in Japan. Recently, in addition to the dienyl aldehyde, a trienyl derivative, (7Z,11Z,13E)-7,11,13-hexadecatrienal (Z7,Z11,E13-16:Ald), was found as another sex pheromone component of females collected in Brazil and California. Thus, we synthesized Z7,Z11,E13-16:Ald and its isomer (Z7,E11,E13-16:Ald) to evaluate their effects on males inhabiting Asia. Starting from 1,7-heptanediol, two corresponding alcohols with trienyl structures were prepared by two applications of the Wittig-coupling reaction and then oxidized to yield objective aldehydes after separation by HPLC with an ODS column. In a citrus orchard in Can-Tho City, Vietnam, P. citrella males could not be caught by a lure baited only with Z7,Z11-16:Ald, but were successfully attracted with a 1 : 3 mixture of Z7,Z11-16:Ald and Z7,Z11,E13-16:Ald. On the other hand, in citrus orchards in Ogasawara (Bonin) Islands and Ehime Prefecture, Japan, neither trienals showed a synergistic effect on male capture by the dienal. Far from being reinforced, the attraction activity of the dienal was diminished by mixing in Z7,Z11,E13-16:Ald. These results indicated that the sex pheromone of the Vietnamese strain is similar to that of Brazilian and Californian strains, but the Japanese strain has established a different communication system from those of the foreign strains.