Identification of a female-produced sex pheromone of the western corn rootworm

Guss, P. L.; Tumlinson, James H.; Sonnet, Philip E.; Proveaux, A. T.

doi:10.1007/bf00987802

Cited by 66 publications

(26 citation statements)

References 12 publications

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“…The case of the Osaka and Japanese beetles is the first one where its importance in a reciprocal behavioral agonist-antagonist context is clearly demonstrated. Nevertheless, there is evidence in the literature to suggest that this phenomenon may occur in other species of Coleoptera (17)(18)(19) and Lepidoptera (20). The pheromone of the Western corn rootworm, Diabrotica virgifera, has been identified as 8-methyl-2-decyl propanoate (17).…”

Section: Resultsmentioning

confidence: 99%

“…Nevertheless, there is evidence in the literature to suggest that this phenomenon may occur in other species of Coleoptera (17)(18)(19) and Lepidoptera (20). The pheromone of the Western corn rootworm, Diabrotica virgifera, has been identified as 8-methyl-2-decyl propanoate (17). When the four possible stereoisomers were tested in the field, it was observed that Diabrotica barberi was attracted to the (2R, 8R)-isomer and inhibited by the (2S, 8R) (18), while Diabrotica longicornis was attracted by the (2S, 8R)-and inhibited by the (2R, 8R)-stereoisomer (19).…”

Section: Resultsmentioning

confidence: 99%

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Chemical communication in scarab beetles: reciprocal behavioral agonist-antagonist activities of chiral pheromones.

Leal

1996

Proc. Natl. Acad. Sci. U.S.A.

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A novel mechanism of reciprocal behavioral agonist-antagonist activities of enantiomeric pheromones plays a pivotal role in overcoming the signal-to-noise problem derived from the use ofa single-constituent pheromone system in scarab beetles. Female Anomala osakana produce (S, Z)-5-(+)-(l-decenyl)oxacyclopentan-2-one, which is highly attractive to males; the response is completely inhibited even by 5% of its antipode. These two enantiomers have reverse roles in the Popillia japonica sex pheromone system. Chiral GCelectroantennographic detector experiments suggest that A. osakana and P. japonica have both R and S receptors that are responsible for behavioral agonist and antagonist responses.To achieve chemical communication in an environment rich in potential chemical cues, insects must overcome the signal-tonoise problem by filtering out a large amount of background noise. In moths, filtering is achieved by using blends of similar compounds, where the specific signature represented by the whole mixture is sine qua non to elicit sexual behavior (1). In marked contrast, some species of Coleoptera (2, 3) have sex pheromone systems composed of a single constituent; such communication channels seem a priori highly prone to noise interference from the environment. Nevertheless, these semiochemicals have by and large at least one chiral center, and chirality plays a major role in determining pheromone specificity. I report here that two scarab beetle species (Coleoptera: Scarabaeidae) achieve single-component chemical communication by a novel mechanism based on the reciprocal behavioral agonist-antagonist activities of the two enantiomers of a single chiral compound. The Osaka beetle, Anomala osakana Sawada, produces and responds only to (S, Z)-5-(+)-(1-decenyl)oxacyclopentan-2-one, the activity of which is completely inhibited by the presence of its enantiomer. On the other hand, it has been previously reported (4) that the Japanese beetle, Popillia japonica, produces and responds only to the (R)-stereoisomer of this lactonic pheromone, with the activity highly inhibited by its antipode.MATERIALS AND METHODS Analytical Procedures. GC was carried out on a HewlettPackard 5890 II Plus instrument equipped with a split/splitless injector, an electronic pressure control, a flame ionization detector, and an HP 3365 Series II Chemstation. Highresolution GC analyses were performed with polar and nonpolar capillary columns, HP-Innowax and HP-5MS (30 m x 0.25 mm x 0.25 gm), respectively. These columns were operated at 70°C for 1 min, increased to 230°C at a rate of 10°C/min, and held at this temperature for 10 min. Chiral resolution was achieved on a capillary column having a trifluoroacetylated y-cyclodextrin phase, Chiraldex GTA (20 m x 0.25 mm: 0.125 ,um; Astec, Whippany, NJ), operated at 150°C and with a (helium) head pressure of 2.5 kg/cm2 (9.42 ml/min; 119 cm/s). Low-resolution MS was carried out with an HP 5890 II Plus gas chromatograph linked to a mass selective detector (Hewlett-Packard; model MSD 5972). GC with...

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Chemical communication in scarab beetles: reciprocal behavioral agonist-antagonist activities of chiral pheromones.

Leal

1996

Proc. Natl. Acad. Sci. U.S.A.

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“…The femaleproduced sex pheromone system seems to be wide spread in Diabrotica genus. In general, virgin females exhibit a potent attraction to males (Guss et al 1982). Sex pheromones also have been isolated and identified from virgin females.…”

Section: Resultsmentioning

confidence: 99%

“…Sex pheromones also have been isolated and identified from virgin females. In the virgifera group, the compound racemic 8-methyl- (Guss et al 1982). Another chemical identified was the 6,12-dimethylpentadecan-2-one, from D. balteata LeConte virgin females (Chuman et al 1987).…”

Section: Resultsmentioning

confidence: 99%

Males Are Attracted by Female Traps: A New Perspective for Management of Diabrotica speciosa (Germar) (Coleoptera: Chrysomelidae) Using Sexual Pheromone

Ventura¹,

Mello²,

Oliveira³

et al. 2001

Neotrop. Entomol.

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Neotropical Entomology 30(3): 361-364 (2001) Machos são Atraídos por Armadilhas com Fêmeas: Uma Nova Perspectiva para Manejo de Diabrotica speciosa (Germar) (Coleoptera: Chrysomelidae) Usando Feromônio Sexual RESUMO -As respostas de Diabrotica speciosa (Germar) para armadilhas com adultos foram estudadas como sugestão da produção de feromônio. Inicialmente, um ensaio para estabelecer a altura adequada para colocação de armadilhas para capturar D. speciosa foi conduzido em campo de feijão. Armadilhas colocadas a 0,25 m de altura capturaram cerca de 3,5 vezes mais adultos do que a 0,5; 0,75 e 1,0 m. As respostas para fêmeas e machos virgens de duas idades (mais novos = 24 a 72h e mais velhos = 72 a 120h após emergência de adultos), fêmeas e machos copulados foram avaliadas em campo de feijão consorciado com café, Coffea arabica L. Armadilhas com fêmeas virgens capturaram cerca de 22 (mais jovens) e 13 vezes (mais velhas) mais adultos machos do que as testemunhas (armadilhas sem insetos). Capturas foram cerca de 70% mais efetivas usando fêmeas mais jovens. Nenhum dos outros tratamentos aumentou as capturas nas armadilhas. Os resultados indicam que há um feromônio sexual produzido por fêmeas em D. speciosa. PALAVRAS-CHAVE:Insecta, semioquímico, altura de colocação de armadilhas, Luperini, Fucata.ABSTRACT -The field responses of Diabrotica speciosa (Germar) to traps baited with adults were studied as an suggestion of the pheromone production. Firstly, an assay to settle a suitable height placement to capture D. speciosa was carried out in common beans, Phaseolus vulgaris L., field. Traps placed at 0.25-m height captured ca. 3.5 times more beetles than 0.5, 0.75 and 1.0-m traps. The responses to virgin females and males of two ages (younger = 24 to 72h and older = 72 to 120h after adult emergence), mated females and males were assessed in common bean interplanted among coffee, Coffea arabica L., field. Virgin females baited traps captured ca. 22 times (younger) and 13 times (older females) more male beetles than control traps. Captures were ca. 70% more effective using younger females. None of the other treatments improved trap attraction. These results strongly indicated that there is a female-produced sexual pheromone in D. speciosa.

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“…34 This compound is also attractive to several Diabrotica species. 35,36 Males of D. virgifera virgifera and D. virgifera zeae responded to (2R,8R)-and (2S,8R)-7, while D. porracea responded exclusively to (2S, 8R)-7.…”

Section: 7-dimethylnonyl Propanoate (7)mentioning

confidence: 99%

Insect pheromone synthesis in Brazil: an overview

Zarbin¹,

Villar²,

Corrêa³

2007

J. Braz. Chem. Soc.

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Nesta revisão estão descritas as sínteses de feromônios de insetos desenvolvidas e publicadas por grupos de pesquisa brasileiros, e tem por objetivo apresentar o estado da arte desta área de pesquisa no país e fornecer uma informação rápida sobre as moléculas já sintetizadas e metodologias empregadas. As sínteses estão apresentadas em ordem cronológica, exceto quando se trata de diferentes metodologias para a mesma molécula.This review describes the syntheses of insect pheromones developed and published by Brazilian research groups and aims to present the state of the art of this area in the country, and also to serves as a quick view of the already synthesized molecules and employed methodology. The syntheses are presented in chronological order, except when they refer to different approaches for the same molecule.

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Identification of a female-produced sex pheromone of the western corn rootworm

Cited by 66 publications

References 12 publications

Chemical communication in scarab beetles: reciprocal behavioral agonist-antagonist activities of chiral pheromones.

Chemical communication in scarab beetles: reciprocal behavioral agonist-antagonist activities of chiral pheromones.

Males Are Attracted by Female Traps: A New Perspective for Management of Diabrotica speciosa (Germar) (Coleoptera: Chrysomelidae) Using Sexual Pheromone

Insect pheromone synthesis in Brazil: an overview

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