No abstract

We tested the hypothesis that green leaf volatiles act as antiaggregants for the mountain pine beetle (MPB),Dendroctonus ponderosac Hopkins. In coupled gas chromatographic-electroantennographic detection (GC-EAD) analysis MPB antennae responded to 30 ng doses of all six-carbon green leaf alcohols tested [1-hexanol, (E)-2-hexen-1-ol, (Z)-2-hexen-1-ol, (E)-3-hexen-1-ol, and (Z)-3-hexen-1-ol], but not to the aldehydes, hexanal or (E)-2-hexenal, or to alcohol or aldehyde homologues with more or fewer than six carbon atoms. In field trapping experiments a blend of green leaf alcohols [1-hexanol, (Z)-2-hexen-1-ol, (E)-3-hexen-1-ol and (Z)-3-hexen-1-ol] effectively disrupted the response to attractive semiochemicals; a blend of the aldehydes hexanal and (E)-2-hexenal was inactive. The two best disruptants. (E)-2-hexen-1-ol and (Z)-3-hexen-1-ol, reduced catches of both sexes to levels not significantly different from catches in unbaited control traps. They also reduced the attack on trees baited with attractive MBP pheromones to a level not significantly different from that on unbaited control trees. Neither of the clerid predators captured,Enoclerus sphegeus (F.) norThanasimus undatulus (Say), was repelled by green leaf volatiles. Our results suggest that green leaf alcohols are promising disruptants which may be used to supplement the antiaggregation pheromone, verbenone, in protecting single high-value trees as well as carefully selected stands with low-level populations of MPBs.

No abstract

Abstract-Male coconut rhinoceros beetles, Orycres rhinoceros (L.), produce three sex-specific compounds, ethyl 4-methyloctanoate, ethyl 4-methylheptanoate, and 4-methyloctanoic acid, the first of which is an aggregation pheromone. Synthesis of these compounds involving conjugate addition of organocuprates to ethyl acrylate is reported. In field trapping experiments, (4S)-ethyl 4-methyloctanoate and the racemic mixture were equally attractive and 10 times more effective in attracting beetles than ethyl chrysanthemumate, a previously recommended attractant. Ethyl 4-methylheptanoate was as attractive as ethyl chrysanthemumate and more attractive than 4-methyloctanoic acid, but further studies are required before it can be classed as an aggregation pherornone. Compared to ethyl 4-methyloctanoate alone, combinations of the three male-produced compounds did not increase attraction, whereas addition of freshly rotting oil palm fruit bunches to pheromone-baited traps sjgnificantly enhanced attraction. With increasing dose, captures of O. rhinocerós'increased, but doses of 6, 9, and 18 mg/day were competitive with 30 mg/day lures. Newly designed vane traps were more effective in capturing beetles than were barrier or pitfall traps. Results of this study indicate that there is potential for using ethyl 4-methyloctanoate in operational programs to control O. rhinoceros in oil palm plantations.

The monoterpene α-pinene, a major component of the terpene composition of Pinus spp., has been reported to act as a host-produced kairomone for a variety of bark beetle species, including the mountain pine beetle, Dendroctonusponderosae Hopkins. However, our experiments indicate that α-pinene autoxidizes under normal temperature and atmospheric conditions to form significant quantities of trans-verbenol, an aggregation pheromone for many species of bark beetles. The quantities of α-pinene present in the resin that can flow from small wounds in pine trees appear to be sufficient to produce trans-verbenol at rates similar to those by female beetles that are actively synthesizing the compound.trans-Verbenol can then autoxidize rapidly to form verbenone, with the content of this compound reaching 8% within 13 weeks of exposure to air. Verbenone is often used by scolytids as an antiaggregation pheromone. Approximately 1.9% of the trans-verbenol and 2.7% of the verbenone found in Porapak Q aerations of phloem with boring spruce beetle, Dendroctonusrufipennis (Kirby), females, as well as 0.8% of the trans-verbenol and 0.8% of the verbenone found in aerations of phloem with boring D. ponderosae females, was due to the autoxidation of α-pinene and (or) the release of oxygenated compounds found in the phloem before bark beetle attack. The natural interconversion of α-pinene, trans-verbenol, and verbenone under ambient conditions suggests that many experiments involving the behavioral activity of these compounds require re-evaluation.

Small trunk pieces of a freshly felled 10-year-old oil palm,Elaeis quineensis (Jacq.), were placed in a modified Nalgene desiccator, and volatiles captured for six days on Porapak Q. Gas chromatographic (GC) analysis of Porapak-Q-trapped volatiles with both flame ionization (FID) and electroantennographic detection (EAD) using male or femaleR. phoenicis antennae revealed several EAD-active compounds. They were identified as: ethyl acetate, ethyl propionate, isobutyl propionate, ethyl butyrate, and ethyl isobutyrate. In field experiments in the La Me Research Station, Côte d'Ivoire, ethyl propionate (50 mg/24 hr) but not all esters combined (50 mg/24 hr each) significantly increased capture ofR. phoenicis in pheromone-baited (3 mg/24 hr) traps. One kilogram of 1- to 3-day-old palm tissue was significantly more effective than ethyl propionate in enhancing pheromone attraction. Superior attraction of palm tissue may be attributed to additional as yet unknown semiochemicals. Alternatively, release rates and/or ratios of synthetic volatiles differed from those of palm tissue at peak attraction.

We describe methods for the rapid generation of minilibraries of substituted alkoxy benzenes (consisting of 4-5 compounds), for screening as insect olfaction or gustation inhibitors. Synthetic or commercially available monoalkoxy benzene compounds were mixed and reacted with various alkyl halides to afford a first set of minilibraries. A second and third set were generated from allyloxy minilibraries via the Claisen rearrangement and subsequent alkylation of the ortho-allyl phenols. We have chosen to prepare a collection of small libraries (as opposed to one large library) to test the response insects exhibit toward blends of compounds. We demonstrate how our minilibraries can be screened, both against insect antennae and against expressed pheromone-binding proteins from the gypsy moth, Lymantria dispar.

Abstract-Coupled gas chromatographic-electroantennographic detection (GC-EAD) analyses and coupled GC-mass spectrometry (MS) of volatiles produced by male and female West Indian sugarcane weevils (W1SW), Metamasius hemipterus sericeus (Oliv.), revealed eight male specific, EAD-aclive compounds: 3-pentanol (1), 2-methyl-4-heptanol (2), 2-methyl-4-octanol (3), *To whom correspondence should be addressed. 'Current address: Department of Chemistry, University of Costa Rica, 2060 San Pedro, San Jose, Costa Rica. 4-methyl-5-nonanol (4), and the corresponding ketones. In field experiments in Florida, alcohols 1-4 in combination with sugarcane were most attractive, whereas addition of the ketones or replacement of alcohols with ketones significantly reduced attraction. In Costa Rica field experiments testing alcohols 1-4 singly and in all binary, ternary, and quaternary combinations revealed 4 in combination with 2 was the major aggregation pheromone, equally attracting male and female WISW. Stereoisomeric 4 and (45,5S)-4, the only isomer produced by WISW, were equally attractive. Addition of 4S-, 4R-or (±)-2 to (4S,5S)-4 significantly enhanced attraction. Sugarcane stalks in combination with 2 plus 4 (ratio of 1:8) were highly synergistic, whereas EAD-active sugarcane volatiles ethyl acetate, ethyl propionate, or ethyl butyrate only moderately increased attractiveness of the pheromone lure.