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Abstract: The ether extract of the females of white-spotted longicorn beetle Anoplophora malasiaca showed activity as contact sex pheromone to males. The extract was fractionated, and a pheromonal activity was revealed only when three fractions; n-hexane, n-hexane/EtOAc 9:1, and EtOAc were blended. The relative structures of gomadalactone A, B, and C, three active components isolated from the EtOAc fraction, were determined by spectroscopic studies to be (1S ∗,4R ∗,5S ∗)-5-hydroxy-4-[(E)-7-hydroxy-4-methylhept-3-enyl]-4,8-dimethyl-3-oxabicyclo[3.3.0]octan-7-en-2,6-dione, (1R ∗,4R ∗,5R ∗)-5-hydroxy-4-[(E)-7-hydroxy-4-methylhept-3-enyl]-4,8-dimethyl-3-oxabicyclo[3.3.0]octan-7-en-2,6-dione, and (1S ∗,4R ∗,5S ∗,8S ∗)-5-hydroxy-4-[(E)-7-hydroxy-4-methylhept-3-enyl]-4,8-dimethyl-3-oxabicyclo[3.3.0]octan-2,6-dione, respectively. [Copyright &y& Elsevier]

Focuses on sex pheromone and related compounds in the Ishigaki and Okinawa strains of the tussock moth Orgyia postica (Walker). Discovery of two distinct electroantennographycally active components, A and B, and a weakly active component C in a solvent extract from virgin females of the Ishigaki strain of the tussock moth; Finding of components A, B, and C in the extract of the females at 4.0, 0.5, and 4.0 ng/female respectively; Confirmation that the attractant pheromone of O. postica of the Ishigaki strain is also (11S,12S)-1; Discussion of the attractiveness of the components to the males on both Japanese islands in the context of the activity and possible evolution of pheromonal polymorphism in the species.

The flower bug Orius sauteri is a generalist predator that occurs throughout Japan, and is a promising indigenous natural enemy for micro-pests such as thrips, aphids, and spider mites. We aimed to manipulate the attraction, dispersal, and settlement behavior of Orius bugs using natural chemical substances emitted by the bugs themselves. To identify potential candidates, we screened components in the whole-body extract of O. sauteri based on antennal response and then determined their chemical structure. A gas chromatograph electroantennographic detector (GC/EAD) indicated that the antennae of males responded to two components in the extract of females. GC/mass spectrometry (MS) showed that these two components were octenal and octadienal. Derivatization or GC-FT-IR analysis identified these components as (E)-2-octenal and (E)-2,7-octadienal. To assess the effect of these components on O. sauteri behavior, we conducted two assays. A field bioassay demonstrated that a blend of the two components functioned as a sex pheromone, and a dispersal assay showed that (E)-2-octenal generated a dose-dependent dispersal response. Our study will provide baseline information for enhancing the retention of O. sauteri on important commercial crops to prey on pest species. [ABSTRACT FROM AUTHOR]

Invasive Anoplophora glabripennis recently became established in Japan and has caused heavy damage to several street-tree species. Overseas, A. glabripennis infests trees of the genera Acer and Populus as common host plants, and Malus, Pyrus, and Prunus (Rosaceae), including apple, pear, and plum trees; it therefore poses a potential risk to the production of economically valuable fruits in Japan. Fruit farms in areas already invaded by A. glabripennis are now threatened with tree infestation. We aimed to determine the potential damage to major fruit species in Japan. In the laboratory, we determined if the adult beetle is attracted to the odor of each of these tree species' branches; two confirmed host plant species and five Rosaceae fruit species, as well as its feeding preferences among branches of one host plant and the five fruit trees and its oviposition preferences among them. Among the fruit species, cherry branch had the highest rate of odor orientation by males. The feeding-preference assay showed that, besides the host plant, Japanese pear was the most consumed among the fruit trees. The potential risk of A. glabripennis laying eggs on fruit-tree branches was high for Japanese pear and above zero for plum, apple, and cherry branches., (© 2024. The Author(s).)

The longhorned beetle Rosalia batesi Harold (Coleoptera; Cerambycidae) is endemic to Japan, where its range extends from Hokkaido to Kyushu. The colorful adults are well-known to entomologists and collectors worldwide. It is a hardwood-boring species with larvae that develop in dead broad-leaf trees. In laboratory bioassays, females were attracted to males, which suggested that males produce a sex pheromone. The congeneric species R. alpina is native to Europe, and another congener, R. funebris, is distributed in North America. The pheromone components produced by males of these species had been previously identified as two compounds from different biosynthetic pathways. In the present study, volatiles were collected from beetles of both sexes, and the analyses of the resulting extracts revealed a single male-specific compound, which was identified as 3,5-dimethyl-6-(1-methylbutyl)-pyran-2-one; this is the same compound as the pheromone of the European R. alpina . This alkylated pyrone structure is, so far, unique among known cerambycid pheromones. In field bioassays with traps baited with the racemic synthetic pheromone, significant numbers of both sexes of R. batesi were attracted in an approximately equal ratio, indicating that the compound is an aggregation-sex pheromone rather than a sex pheromone.

In recent years, several invasive woodborers (Coleoptera: Cerambycidae) have been found in Japan. Aromia bungii is a worldwide important pest of fruits and ornamental species of the genus Prunus. It invaded Japan in the early 2010s and now causes heavy damage to stone fruit trees. Anoplophora glabripennis and Apriona swainsoni are destructive pests of street, ornamental and horticultural trees. The first step in intercepting these beetles is to detect their presence early in their infestation, as accurate identification is crucial for their management. Ejected frass is a major sign of infestation and likely holds information on the insect. We focused on chemicals in both larvae and frass, and conducted a GC-MS analysis of these three invasive beetles and the native Anoplophora malasiaca. In all four species, 4 or 5 species-specific hydrocarbons were detected in both larvae and frass. These results indicate that analysis of hydrocarbons in frass could allow definitive detection of invasive wood-boring pests., (© 2023. The Author(s).)

Mealybug females release sex pheromones to attract conspecific males for mating. It is critical for mealybug males, which are fragile and short-lived, to respond to the pheromone of their species without time- and energy-consuming cross-attractions to other species. Thus, mealybug pheromone systems are considered to have evolved to be species-specific with unique structures in each species and offer an opportunity to study the diversity of pheromone chemistry that mediates intersexual courtship signals. More than 20 mealybug pheromones are reported to be monoterpenes in general, with only one exception, a hemiterpene alcohol esterified with a medium-chain fatty acid (MCFA), found in the Matsumoto mealybug, Crisicoccus matsumotoi. However, it is unknown whether this is truly exceptional, or if similar compounds are used in other related mealybugs. In this study, we isolated and characterized the pheromone of an allied species, the azalea mealybug C. azaleae. Using gas chromatography-mass spectrometry, nuclear magnetic resonance spectroscopy, and bioassays with synthetics, the pheromone was shown to be composed of isopropyl (E)-7-methyl-4-nonenoate, isopropyl (E)-7-methyl-4-octenoate, and ethyl (E)-7-methyl-4-nonenoate. Surprisingly, the structures of these compounds do not include hemiterpene nor monoterpene motifs but have methyl-branched MCFA parts that are similar to an acid moiety of the C. matsumotoi pheromone. This study implies irregular events for the divergence of pheromone structures in ancestors of the genus Crisicoccus and other mealybugs., (© 2022. The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature.)

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.

The longhorned beetle Aromia bungii (Coleoptera: Cerambycidae) is a major pest of stone fruit trees in the genus Prunus, including cherries, apricots, and peaches. Its native range includes China, Korea, Mongolia, and eastern Russia, but it has recently invaded and become established in several countries in Europe, and Japan, and it has been intercepted in shipments coming into North America and Australia. Here, we report the identification of its male-produced aggregation pheromone as the novel compound (E)-2-cis-6,7-epoxynonenal. In field trials in its native range in China, and in recently invaded areas of Japan, the pheromone attracted both sexes of the beetle. Thus, the pheromone should find immediate use in worldwide quarantine surveillance efforts to detect the beetle in incoming shipments. The pheromone will also be a crucial tool in ongoing efforts to eradicate the beetle from regions of the world that it has already invaded.