Contact Sex Pheromone Activity of Synthetic Gomadalactones in Male White-Spotted Longhorn Beetle, Anoplophora malasiaca (Coleoptera: Cerambycidae).

The elytra of females of the white-spotted longhorn beetle, Anoplophora malasiaca (Coleoptera: Cerambycidae), are coated with a contact sex pheromone, which was previously shown to be composed of at least three chemical groups. Individually, the chemical groups had little pheromonal activity, but a blend of all three exhibited activity equal to that of the crude female extract. Two groups are female-specific aliphatic hydrocarbons and ketones, which were previously synthesized and confirmed to elicit mating behavior. The third group consists of three lactones, gomadalactones A, B, and C, whose chemical structures were previously identified. These have now been synthesized, and the contact sex pheromone activities of synthetic gomadalactones A, B, and C, and the diastereomer of gomadalactone C, were tested in bioassays in this study. When tested in combination with synthetic hydrocarbons and ketones at the same doses as found in female elytra extract, the individual gomadalactones and a blend showed potent pheromonal activity equivalent to that of the crude extract of the elytra of female beetles. This completes the identification of the essential components of the contact sex pheromone of A. malasiaca. Redundancy of components in the hydrocarbon and ketone groups required to elicit mating behavior was observed previously, and this was also true for the gomadalactones.

Mating disruption for control of Melanotus okinawensis (Coleoptera: elateridae) with synthetic sex pheromone.

A mating disruption experiment to control Melanotus okinawensis Ohira (Coleoptera: Elateridae) was conducted at a sugarcane (Saccharum spp.) field and a wild Japanese pampas, Miscanthus sinensis Anderss, grassland on Minami-Daito Island (3,057 ha) from 2001 to 2007. The sugarcane field and the pampas grassland were treated with synthetic sex pheromone that evaporated from a polyethylene tube dispenser. The mean total catches obtained by monitoring traps in the sugarcane fields decreased by 96.1% in 2001 from the previous year on Minami-Daito Island. The mean total trap catches in the treated area further decreased by 74.0% from 2001 until 2007 as cumulative effects. Simultaneously, the number of adults captured by hand decreased from 4.7 per sugarcane field in 2001 to 0.5 in 2007 (89.3% reduction), whereas those captured in the untreated area (Miyagi Island) did not show such a decrease. The mating rates were significantly lower in the females captured in the treated area (14.3-71.4%) than those in the untreated area (96.9-100%). However, the amount of the decrease in the trap catches was relatively small at first (39.6% reduction) in the Japanese pampas grassland on the periphery of the Island. This was probably due to the loss of pheromone substance caused by the strong seasonal wind in the periphery. However, mean total trap catches at the periphery also decreased within several years; significant decreases were detected until 2003, 2006, and 2007. These results indicated that the mating disruption effectively reduced an isolated population of M. okinawensis.

Intraspecific variation of cuticular hydrocarbon composition in Formica japonica Motschoulsky (Hymenoptera: Formicidae).

Cuticular hydrocarbons and morphological features were compared among 80 Formica japonica colonies collected in Japan. Although a few morphological differences were found in workers among the colonies, four different types of cuticular hydrocarbon composition were observed. This was supported by a principal component analysis. We further compared the cuticular hydrocarbons among a total of approximately 400 F. japonica colonies, and categorized the hydrocarbon components into four types based on the result of discriminant analyses for the first 80 colonies. Type 1 was observed in colonies mainly collected in southern Honshu, Shikoku, and Kyushu. Types 2, 3, and 4 were from colonies with primary collections in Southern Honshu, central and Pacific coast northern Honshu, and the Sea of Japan coasts of northern Honshu and Hokkaido, respectively. The occurrence of four distinct types of CHC composition suggests that the colonies that produce them are separate species.

Identification of a sex pheromone component of the geometrid moth Milionia basalis pryeri.

A single component in extracts of virgin female Milionia basalis pryeri moths elicited responses from male moth antennae. This compound (ca. 7 ng/female) was identified as (Z,Z)-(3S,4R)-3,4-epoxynonadeca-6,9-diene by GC-MS and NMR analyses, microchemical reactions, and comparative chiral HPLC. In a field test, synthetic (Z,Z)-(3S,4R)-3,4-epoxynonadeca-6,9-diene attracted male moths. The opposite enantiomer, the racemic mixture, and virgin female moths held in small cages attracted no more moths than the solvent controls.

Sex pheromone and related compounds in the Ishigaki and Okinawa strains of the tussock moth Orgyia postica (Walker) (Lepidoptera: Lymantriidae).

Two distinct electroantennographycally active (EAG-active) components, A and B, and a weakly active component C were found in a solvent extract from virgin females of the Ishigaki strain of the tussock moth, Orgyia postica (Walker). Components A, B, and C were found in the extract of the females at 4.0, 0.5, and 4.0 ng/female respectively. Components A, B, and C were identified as (6Z,9Z,11S,12S)-11,12-epoxyhenicosa-6,9-diene [(11S,12S)-1: posticlure], (6Z)-henicos-6-en-11-one (2), and (6Z,9Z)-henicosa-6,9-diene (3), respectively. Component B was absent in the extract from the Okinawa strain, in which components A and C were present at 2.0 and 1.5 ng/female respectively. (11S,12S)-1 and the racemic mixture showed attractiveness for both the Okinawa and Ishigaki strains, whereas (11R,12R)-1 did not. The addition of 2 significantly reduced the trap catches with (11S,12S)-1 on the Okinawa strain which lacked 2, while there was no significant inhibitory effect on the Ishigaki strain. The addition of 3 to (11S,12S)-1 did not significantly affect trap catches at Ishigaki or Okinawa. This confirmed that the attractant pheromone of O. postica of the Ishigaki strain is also (11S,12S)-1.

Identification of epoxyhenicosadiene and novel diepoxy derivatives as sex pheromone components of the clear-winged tussock moth Perina nuda.

Four EAG-active components (A-D) were found in the solvent extract of virgin females of the clear-winged tussock moth, Perina nuda. The most abundant component (B, ca. 250 ng/female) was identified as (3Z,6S,7R,9Z)-6,7-epoxyhenicosa-3,9-diene by GC-MS analyses of the extract, chemical derivatization, and comparative chiral HPLC. Minor components also elucidated were (3Z,9Z)-cis-6,7-epoxyicosa-3,9-diene, (A); (3R,45,6S,7R,9Z)-3,4-6,7-diepoxyhenicos-9-ene, (C); and its 3S,4R,6S,7R isomer, (D); with amounts of 0.4, 5, and 8 ng/female, respectively. Component B showed weak attractiveness to male moths in the field. The attractiveness was significantly enhanced by addition of component(s) C and/or D. No males were captured with either the antipode of component B or its mixtures with the minor components. In this field test, noctuid Hypocala rostrata males were also attracted with the synthetic P. nuda pheromone.