Synthetic sex pheromone in a long-lasting lure attracts the visceral leishmaniasis vector, Lutzomyia longipalpis, for up to 12 weeks in Brazil.

Current control methodologies have not prevented the spread of visceral leishmaniasis (VL) across Brazil. Here, we describe the development of a new tool for controlling the sand fly vector of the disease: a long-lasting lure, which releases a synthetic male sex pheromone, attractive to both sexes of Lutzomyia longipalpis. This device could be used to improve the effectiveness of residual insecticide spraying as a means of sand fly control, attracting L. longipalpis to insecticide-treated animal houses, where they could be killed in potentially large numbers over a number of weeks. Different lure designs releasing the synthetic pheromone (±)-9-methylgermacrene-B (CAS 183158-38-5) were field-tested in Araçatuba, São Paulo (SP). Experiments compared numbers of sand flies caught overnight in experimental chicken sheds with pheromone lures, to numbers caught in control sheds without pheromone. Prototype lures, designed to last one night, were first used to confirm the attractiveness of the pheromone in SP, and shown to attract significantly more flies to test sheds than controls. Longer-lasting lures were tested when new, and at fortnightly intervals. Lures loaded with 1 mg of pheromone did not attract sand flies for more than two weeks. However, lures loaded with 10 mg of pheromone, with a releasing surface of 15 cm2 or 7.5 cm2, attracted female L. longipalpis for up to ten weeks, and males for up to twelve weeks. Approximately five times more sand flies were caught with 7.5 cm2 10 mg lures when first used than occurred naturally in non-experimental chicken resting sites. These results demonstrate that these lures are suitably long-lasting and attractive for use in sand fly control programmes in SP. To our knowledge, this is the first sex pheromone-based technology targeting an insect vector of a neglected human disease. Further studies should explore the general applicability of this approach for combating other insect-borne diseases.

Inhibition of the responses to sex pheromone of the fall armyworm, Spodoptera frugiperda.

Trifluoromethyl ketones reversibly inhibit pheromone-degrading esterases in insect olfactory tissues, affecting pheromone detection and behavior of moth males. In this work, (Z)-9-tetradecenyl trifluoromethyl ketone (Z9-14:TFMK), a closely-related analogue of the pheromone of the fall armyworm, Spodoptera frugiperda (Smith) (Lepidoptera: Noctuidae), was prepared and tested in electroantennogram and field tests as possible inhibitors of the pheromone action. The electroantennogram parameters, amplitude, and the repolarization time of the antennal responses of S. frugiperda males were affected by Z9-14:TFMK vapors. Exposure of male antennae to a stream of air passing through 100 µg of the ketone produced a significant reduction of the amplitude and an increase of 2/3 repolarization time signals to the pheromone. The effect was reversible and dose-dependent. In the field, the analogue significantly decreased the number of males caught when mixed with the pheromone in 10:1 ratio. The results suggest that Z9-14:TFMK is a mating disruptant of S. frugiperda and may be a good candidate to consider in future strategies to control this pest.

Host marking pheromone (HMP) in the Mexican fruit fly Anastrepha ludens.

Host marking pheromones (HMPs) are used by insects to mark hosts (usually a fruit) where they have already laid eggs. The compounds serve as a deterrent to conspecifics avoiding over-infestation of hosts (i.e. repeated egg-laying into an already occupied/used host). If these HMPs are sprayed onto commercially valuable fruit they act as deterrents preventing attack by females interested in laying eggs into the valuable commodity. Having no insecticidal or toxic properties, and being natural products (or close derivatives thereof) they could be used as fruit sprays to replace insecticides, or in combination with other products to improve efficacy. This review discusses the isolation, and synthesis of the HMP of the Mexican fruit fly Anastrepha ludens a feared pest of citrus and mangos in Mexico and Central America. This compound is also recognized by females of other pestiferous species in the same genus Anastrepha distributed from the Southern USA to Northern Argentina, including many Caribbean Islands. The synthetic HMP was shown to exhibit strong electrophysiological activity against A. ludens and excellent interspecies cross recognition with other Anastrepha species. Behavioural tests confirmed the HMP deterring effect of the synthetic natural product. Further studies enabled us to drastically simplify the structure of the HMP and obtain a derivative, which we named Anastrephamide, which shows HMP deterring effects very similar to the natural product in laboratory and field tests. The potential use of such HMP derivatives in a crop protection scenario is briefly discussed.

Long-term field trial to control the invasive Argentine ant (Hymenoptera: Formicidae) with synthetic trail pheromone.

Previous short-term experiments showed that trail following behavior of the Argentine ant, Linepithema humile (Mayr) (Hymenoptera: Formicidae), can be disrupted by a high concentration of synthetic trail pheromone component (Z)-9-hexadecenal. In this study, a long-term field trial was conducted in 100-m2 plots of house gardens in an urban area of Japan to see whether the control effect on Argentine ants can be obtained by permeating synthetic trail pheromone from dispensers. The dispensers were placed in the experimental plots during the ant's active season (April-November) for 2 yr with monthly renewal. To estimate Argentine ant population density, foraging activity of Argentine ants in the study plots was monitored by monthly bait surveys. Throughout the study period, Argentine ant foraging activity was suppressed in the presence of the dispensers, presumably via trail forming inhibition. In contrast, the level of foraging activity was not different between treatment and no-treatment plots when the dispensers were temporarily removed, suggesting that treatment with pheromone dispensers did not suppress Argentine ant density in the treatment plots. Population decline may be expected with larger-scale treatment that covers a significant portion of the ant colony or with improvement in the potency of the disruptant.

Male-produced sex pheromone of the cerambycid beetle Hedypathes betulinus: chemical identification and biological activity.

We identified, synthesized, determined the diel periodicity of release, and tested the bioactivity of components of the male-produced sex pheromone of Hedypathes betulinus (Coleoptera: Cerambycidae: Lamiinae). Gas chromatographic-mass spectrometric analysis of headspace volatiles from adult beetles showed three male-specific compounds, which were identified as (E)-6,10-dimethyl-5,9-undecadien-2-yl acetate (major component), (E)-6,10-dimethyl-5,9-undecadien-2-one (geranylacetone), and (E)-6,10-dimethyl-5,9-undecadien-2-ol. Release of these chemicals was dependent on time of the photoperiod and presence of the host plant. Pheromone release took place primarily during the photophase, with maximum release occurring between 4 and 6 hr after the onset of photophase. The amount of pheromone released by males was much greater when they were in the presence of their host plant than when they were not. In Y-tube olfactometer tests, a ternary mixture of the compounds was attractive to female beetles, although the individual compounds were not attractive by themselves. Addition of volatiles from the host plant greatly increased the attractiveness of the ternary pheromone mixture and of the major pheromone component alone.

A new pheromone race of Acrobasis nuxvorella (Lepidoptera: Pyralidae).

The sex pheromone of the monophagous Acrobasis nuxvorella Neunzig (Lepidoptera: Pyralidae) was reported as (9E,11Z)-hexadecadienal (9E,11Z-16:Ald) (Biorg. Med. Chem. 4: 331-339, 1996), and it has since been an effective integrated pest management (IPM) tool for monitoring this pest in the United States, but not in Mexico. Field and laboratory studies were conducted to confirm that the species in Mexico was indeed A. nuxvorella and to investigate the pheromone chemistry of the Mexican populations of this species. Initial field trials testing compounds structurally related to the known pheromone component, and blends thereof, indicated that a 100 microg:100 microg blend of (9E,11Z)-hexadecadien-1-yl acetate (9E,11Z-16:Ac):9E,11Z-16:Ald in rubber septa was effective in attracting male moths in Mexico. Coupled gas chromatography-electroantennogram analyses confirmed the presence of these compounds in extracts of pheromone glands of females, and antennae of male moths also responded to the alcohol analog (9E,11Z)-hexadecadien-1-ol (9E,11Z-16:OH). Subsequent field trials of various blends of these three compounds in Mexico showed that 1) both the acetate and aldehyde components were required for optimal attraction of male moths of the Mexican populations, and 2) addition of the alcohol suppressed attraction of males in a dose-dependent manner. Tests with the 1:1 9E,11Z-16:Ac:9E,11Z-16:Ald blend at various sites in the United States showed that this blend attracted some moths, but that moths attracted to 9E,11Z-16:Ald alone were predominant in the population. Furthermore, in preliminary studies the latter seemed not to respond to the blend. These findings indicate that there are two pheromone types of the pecan nut casebearer, and they have major implications for the direct use of these pheromones in pecan IPM.

A new method for the preparation of 1,5-diynes. Synthesis of (4E,6Z,10Z)-4,6,10-hexadecatrien-1-ol, the pheromone component of the cocoa pod borer moth Conopomorpha cramerella.

[reaction: see text] A new method for the synthesis of 1,5-diynes, from the reaction of 1,3-dilithiopropyne and propargyl chlorides, was developed. This new methodology was used to prepare (4E,6Z,10Z)-4,6,10-hexadecatrien-1-ol, one of the pheromone components of the cocoa pod borer moth Conopomorpha cramerella, in 51% overall yield.

Identification, syntheses, and characterization of the geometric isomers of 9,11-hexadecadienal from female pheromone glands of the sugar cane borer Diatraea saccharalis.

Chemical analysis of the pheromone glands of the sugar cane borer Diatraea saccharalis has shown the presence of the four geometric isomers of 9,11-hexadecadienal (1-4), in addition to hexadecanal and (Z)-hexadec-11-enal. We here report the syntheses and characterization of compounds 1-4. One starting material, 9-decen-1-ol, has been used to obtain all of them via divergent synthetic routes.

Identification and synthesis of a kairomone mediating host location by two parasitoid species of the cassava mealybug Phenacoccus herreni.

Two encyrtid species, Acerophagus coccois and Aenasius vexans, parasitoids of the cassava mealybug Phenacoccus herreni use a contact kairomone from the body surface of their host as a host-location stimulant. The kairomone was synthesized and identified as O-caffeoylserine based on a combination of chromatographic methods. The synthetic compound was determined to be active.