Raspberry ketone analogs : vapour pressure measurements and attractiveness to Queensland fruit fly, Bactrocera tryoni (Froggatt) (Diptera : Tephritidae)

The Queensland fruit fly, Bactrocera tryoni (Froggatt) (Q-fly), is a major horticultural pest in Eastern Australia. Effective monitoring, male annihilation technique (MAT) and mass trapping (MT) are all important for control and require strong lures to attract flies to traps or toxicants. Lure strength is thought to be related in part to volatility, but little vapour pressure data are available for most Q-fly lures. Raspberry ketone (4-(4-hydroxyphenyl)-2-butanone) and analogs that had esters (acetyl, difluoroacetyl, trifluoroacetyl, formyl, propionyl) and ethers (methyl ether, trimethylsilyl ether) in replacement of the phenolic group, and in one case also had modification of the 2-butanone side chain, were measured for their vapour pressures by differential scanning calorimetry (DSC), and their attractiveness to Q-fly was assessed in small cage environmentally controlled laboratory bioassays. Maximum response of one category of compounds, containing both 2-butanone side chain and ester group was found to be higher than that of the other group of compounds, of which either of 2-butanone or ester functionality was modified. However, linear relationship between vapour pressure and maximum response was not significant. The results of this study indicate that, while volatility may be a factor in lure effectiveness, molecular structure is the dominating factor for the series of molecules investigated.16 page(s

Raspberry ketone trifluoroacetate, a new attractant for the Queensland fruit fly, Bactrocera tryoni (Froggatt)

Queensland fruit fly, Bactrocera tryoni (Q-fly), is a major pest of horticultural crops in eastern Australia. Lures that attract male Q-fly are important for detection of incursions and outbreaks, monitoring of populations, and control by mass trapping and male annihilation. Cuelure, an analog of naturally occurring raspberry ketone, is the standard Q-fly lure, but it has limited efficacy compared with lures that are available for some other fruit flies such as methyl eugenol for B. dorsalis. Melolure is a more recently developed raspberry ketone analog that has shown better attraction than cuelure in some field studies but not in others. A novel fluorinated analog of raspberry ketone, raspberry ketone trifluoroacetate (RKTA), has been developed as a potential improvement on cuelure and melolure. RKTA placed on laboratory cages containing 2-week-old Q-flies elicited strong behavioral responses from males. Quantification of Q-fly responses in these cages, using digital images to estimate numbers of flies aggregated near different lures, showed RKTA attracted and arrested significantly more flies than did cuelure or melolure. RKTA shows good potential as a new lure for improved surveillance and control of Q-fly.7 page(s

Fly Response Probabilities over Time.

<p>The response of flies to eight lures were measured over 170 seconds. An exponential function was fitted. Plots of the residuals are given.</p

Vapour Pressure (<i>P</i>) and Enthalpy of Vaporisation (Δ<i>H</i>_<i>vap</i>) of Raspberry Ketone and Eight Analogs at 298.15 K.

<p>Vapour Pressure (<i>P</i>) and Enthalpy of Vaporisation (Δ<i>H</i>_<i>vap</i>) of Raspberry Ketone and Eight Analogs at 298.15 K.</p

Maximum Response Probability as a Function of Vapour Pressure.

<p>CL: 4-(4-acetoxyphenyl)-2-butanone, DF: 4-(4-(2,2-difluoroacetoxy)phenyl)-2-butanone, RKTA: 4-(4-(2,2,2-trifluoroacetoxy)phenyl)-2-butanone, ML: 4-(4-formyloxyphenyl)-2-butanone, AA: 4-(4-methoxyphenyl)-2-butanone, TMSRK: 4-(4-((trimethylsilyl)oxy)phenyl)-2-butanone, PRK: 4-(4-propionyloxyphenyl)-2-butanone, MAPP: methyl 3-(4-acetoxyphenyl)propionate.</p

Chemical Structures of the Attractants.

<p>Chemical Structures of the Attractants.</p

Percepção química e visual de Anastrepha fraterculus (Diptera, Tephritidae) em laboratório Chemical and visual perception of Anastrepha fraterculus (Diptera, Tephritidae) in laboratory

A mosca-das-frutas-sul-americana, Anastrepha fraterculus (Wiedemann, 1830), é uma das principais pragas da fruticultura no Brasil. Durante a alimentação, as larvas fazem galerias nos frutos, alterando o sabor e prejudicando a produção e comercialização dos mesmos. O presente trabalho teve como objetivo estudar fatores envolvidos na escolha do hospedeiro por A. fraterculus. Foram avaliadas as respostas eletroantenográficas de machos e fêmeas a extratos etanólicos de frutos verdes e maduros de pessegueiro - Prunus persica, cultivar Chimarrita (Rosaceae), pitangueira - Eugenia uniflora (Myrtaceae), guabirobeira - Campomanesia xanthocarpa (Myrtaceae) e araçazeiro - Psidium cattleianum (Myrtaceae). Foram também observadas as influências da cor (amarela, verde e vermelha) e da composição do substrato de oviposição (polpas de araçá, guabiroba, pitanga e pêssego) na fecundidade da espécie. As respostas eletroantenográficas de fêmeas foram significativamente distintas para os extratos de guabiroba verde e madura, araçá maduro e pitanga verde. Em antenas de machos, as maiores despolarizações médias foram registradas em resposta aos extratos de guabiroba verde e madura, araçá verde e maduro e pitanga verde. As respostas eletrofisiológicas geradas não diferiram estatisticamente entre os sexos, para todos os tratamentos. A cor do substrato não afetou a oviposição. As fêmeas ovipositaram mais nos substratos contendo polpa de pêssego e de guabiroba, quando comparados aos respectivos controles.<br>The South American fruit fly Anastrepha fraterculus (Wiedemann, 1830) is one of the greatest threats to the fruit growing industry in Brazil. During the feeding process, the larvae build galleries within the fruit, altering the flavor and damaging its production and commercialization. The present work had as its objective to study the factors involved in the choice of the host by A. fraterculus. Electroantennographic responses of the males and females to the ethanolic extracts of the fruits of the peach tree - Prunus persica, cultivar Chimarrita (Rosaceae), Surinam cherry tree - Eugenia uniflora (Myrtaceae), Guabirobeira tree - Campomanesia xanthocarpa (Myrtaceae) and Brazilian guava tree - Psidium cattleianum (Myrtaceae) were considered. Also recorded was the influence of the color (yellow, green and red) and the composition of the substratum of oviposition (pulps of Brazilian guava, Guabiroba, Surinam cherry and peaches) in the fecundity. Electroantennographic responses of the females were distinct to the extracts of the unripe and ripe Guabiroba, ripe Brazilian guava and unripe Surinam cherry. In antennae of the males, the greatest depolarization average was registered in the responses to the extracts of ripe and unripe Guabiroba, ripe and unripe Brazilian guava and unripe Surinam cherry. Electrophysiologic responses did not differ statistically between the sexes for all the treatments. The colors of the substratum of oviposition did not affect the fecundity. The females ovipositioned more on the substratum containing pulp of peaches and of Guabiroba, when compared to the respective controls