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Improved Attractants for the Melon Fly,Bactrocera Cucurbitae

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Improved Attractants for the Melon Fly,Bactrocera Cucurbitae Proceedings of 6th International Fruit Fly Symposium 6–10 May 2002, Stellenbosch, South Africa pp. 283–290 Improved attractants for the melon fly, Bactrocera cucurbitae J.E. Oliver1*, V. Casaña-Giner1, E.B. Jang2, G.T. McQuate2 & L. Carvalho2 1U.S. Department of Agriculture, Agricultural Research Service, Chemicals Affecting Insect Behavior Laboratory, Beltsville, MD 20705, U.S.A. 2U.S. Department of Agriculture, Agricultural Research Service, Pacific Basin Research Agricultural Center, Hilo, HI 96720, U.S.A. Virtually all of the standard lures for the melon fly, Bactrocera cucurbitae, are based on raspberry ketone, and of these, cuelure (the acetate of raspberry ketone), has for many years been the most widely used. We have synthesized and evaluated additional potential melon fly attractants whose structures are also related to that of raspberry ketone, focusing in particular on analogs with enhanced volatility. We have found that raspberry ketone formate is a superior attractant, even to cuelure. Reasons for its superior performance are discussed. INTRODUCTION 92 species that responded to raspberry ketone, The history of melon fly attractants goes back at with about 40 responding to methyl eugenol). least to 1957 when Barthel et.al.(1957) reported in Both methyl eugenol and raspberry ketone are Science that anisylacetone attracted sexually natural products, occurring in various plants, and mature males. The authors commented on its Metcalf (1990) and Metcalf et al. (1979) discussed resemblance to methyl eugenol, which was this subject in an evolutionary context. Various already known to be an excellent attractant for authors have shown that the male flies are able to the oriental fruit fly (Fig. 1). Anisylacetone was sequester these compounds in their pheromone not an especially effective attractant, and a glands, where they increase competitiveness and few years later Beroza et al. (1960) reported, also mating success (a summary, with references, in Science, that 4-(p-acetoxyphenyl)-2-butanone can be found in Shelly & Villalobos 1995; see also (cuelure) was a much more potent attractant, Shelly 2000). Thus, since about 1970, the thinking and that it also attracted immature males. has gradually shifted from the early empirical Cuelure has served as the standard melon fly lure approaches toward the evaluation of attractants since that time. It is interesting that both anisyl- within the contexts of fruit fly chemistry and acetone and cuelure were discovered through behaviour. empirical screening procedures as opposed to any In 1982, ethyl p-hydroxybenzoate was discovered kind of rational extrapolation from known natural as a component of the rectal gland secretion of products. the melon fly, although it was incorrectly identi- In1974, Drew(1974)citedworkdatingfrom1959 fied at the time (Baker et al. 1982; Nishida et al. wherein raspberry ketone (known as Willison’s 1990; Perkins et al. 1990; Fletcher & Kitching lure) had been developed as an attractant for 1995). Also about 1982, Flath & Ohinata (1982) male Dacus tryon. The history of this discovery is identified 4-phenyl-2-butanone in flowers of the uncertain; presumably it was empirical in nature orchid Dendrobium superbum, which were attrac- and it may not have been appreciated outside of tive to melon flies. There is evidently a plant called Australia until considerably later. Doolittle et al. fruit fly plant, which is attractive to several species (1970) and Keiser et al. (1973) noted that as much of fruit flies, and from it has been identified as 50% raspberry ketone in cuelure did not de- benzyl acetate and 4-methoxybenzyl acetate crease the efficacy of the latter as an attractant (Lewis et al. 1988). Metcalf and coworkers (1986) (raspberry ketone was regarded as a contami- synthesized and evaluated a series of substituted nant or degradation product of cuelure, not as a benzyl acetates, and found the most active to be primary attractant). 4-hydroxybenzyl acetate. The authors noted that In 1974 Drew (1974) published his pivotal obser- this compound is isosteric to raspberry ketone (a vation that the Dacinae can be divided into two CH2 of the latter substituted by an oxygen). categories, one whose males are attracted to Recently, Tan & Nishida (2000) reported that methyl eugenol, and one to whom raspberry flowers of the wild orchid Bulbophyllum patens ketone is attractive (he noted that there were some attracted males of several fruit fly species, and *To whom correspondence should be addressed. identified zingerone as the principal attractive E-mail: [email protected] ingredient. In this case too, male flies seques- 284 Proceedings of the 6th International Fruit Fly Symposium Fig. 1. Aromatic compounds attractive to Bactrocera cucurbitae. tered zingerone in pheromone glands. In at least nols are somewhat more easily hydrolysed than one species,zingerone is metabolized to the corre- esters of aliphatic alcohols, and it has been specu- sponding alcohol zingerol, which is used by the lated that facile hydrolysis of cuelure, e.g. in male to attract conspecific females. Zingerone is moist air, generates raspberry ketone which is the noteworthy in that it possesses structural features true attractant.This idea has been strongly empha- of both raspberry ketone and methyl eugenol, sized by Metcalf & Metcalf (1992), but also, and and is unique in its ability to attract both categories earlier, by others (cited as a personal communica- of flies, those normally responding to raspberry tion in Drew’s paper (Drew 1974). ketone as well as those attracted by methyl eugenol. MATERIALS AND METHODS In spite of these advances, from a practical Methods for syntheses of new compounds have standpoint, cuelure has remained the melon fly been described elsewhere (Casaña-Giner et al. attractant since its discovery. And cuelure is 2003a,b). Applications and a description of the simply the acetate of raspberry ketone, a relation- olfactometer have also been described previ- ship that has escaped no-one since the central ously (Casaña-Giner et al. 2003b; Jang et al. 1997; role of the latter became known. Esters of phe- Jang et al. 2001). Oliver et al.: Improved attractants for the melon fly 285 Fig. 2. Fluorinated analogs of raspberry ketone. Most field data were obtained with released flies Smart 1991), and multiply fluorinated compounds as previously described by Casaña-Giner et al. are sometimes more volatile than their hydrogen- (2003b), and studies with wild melon flies were containing counterparts. Figure 2 demonstrates conducted in Kapoho on the island of Hawaii. some of the sites of fluorine substitution of Traps were placed 10–15 m apart in a citrus analogs we prepared. Discussion of these analogs orchard, and serviced weekly. warrants little time because the approach was simply unsuccessful. The analog with the phenolic RESULTS AND DISCUSSION OH replaced by fluorine was somewhat attractive, Conventional wisdom states that raspberry and a few others demonstrated marginal attrac- ketone is intrinsically highly attractive, but, from a tiveness, but none were nearly as attractive as practical standpoint, is simply too non-volatile to raspberry ketone or cuelure (Casaña-Giner et al. serve as an effective bait in traps (the real issue is 2003a). release from a formulating matrix, a phenomenon A few non-fluorinated analogs were also synthe- influenced by several factors of which volatility sized and evaluated. Neither of the bicyclic is only one). Although itself possessing limited analogs (Fig. 3) was attractive. These were not volatility, cuelure enters the air more rapidly than expected to be particularly more volatile than raspberry ketone so that it performs much better raspberry ketone, but rather were synthesized to under field conditions [Metcalf & Metcalf (1992) see if they might shed light on a raspberry ketone reported that cuelure was released ~20 times receptor. If the receptor were to accommodate faster than raspberry ketone from filter papers the molecule in a folded configuration (as illus- treated with 0.1 µg]. However, in spite of its trated in Fig. 3), one or the other of these com- advantages,it has been noted that cuelure is a less pounds might fit that receptor quite neatly. Their effective attractant for melon flies than methyl inactivity seems to suggest that raspberry ketone eugenol is for oriental fruit flies (Shelly & Villalobos fits into the receptor with the chain extended away 1995), and various groups have cited a need for from the ring. a better melon fly attractant, citing the limited More encouraging results were realized with silyl volatility of cuelure as its major shortcoming. It ether derivatives of raspberry ketone (Fig. 4). In was in this context that we were asked to try to the olfactometer, raspberry ketone trimethylsilyl develop a more active, particularly a more vola- ether was 71% as attractive as raspberry ketone tile, melon fly attractant. For the reasons out- and 67% as attractive as cuelure. More impor- lined, we chose to not deviate drastically from tantly, the attractiveness of the trimethylsilyl ether the general raspberry ketone framework, but in a field test was comparable to that of cuelure [no rather to attempt relatively subtle modifications statistical difference in the LSD test (" = 0.05)], and that might lead to enhanced release from formula- more interesting, it caught significantly more flies tion matrices. Accordingly, additional analogs than did raspberry ketone.These latter results illus- have been synthesized and
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