Lyonetia Prunifoliella Research Articles

Asymmetric synthesis of the sex pheromone of the apple leafminer, Lyonetia prunifoliella.

Lyonetia prunifoliella is a significant pest in orchards and damages apple. The sex pheromones of this pest were prepared via a new and concise method. The central to our method were Evans' chiral auxiliaries, the addition of chiral Grignard reagent to aldehyde and Wittig coupling.

Lyonetia prunifoliella (Hübner, 1796) (Lepidoptera: Lyonetiidae): a review of the species in England and consideration of L. padifoliella (Hübner, [1813

This paper reviews British records of Lyonetia prunifoliella (Hübner, 1796) up to the end of 2017: all are from England. The account of the species in The Moths and Butterflies of Great Britain and Ireland 2 is considered and certain changes are suggested. Detailed descriptions of the larva, larval mine and pupa are provided, with illustrations. Larval foodplants are reviewed both of this species and L. padifoliella (Hübner, [1813]) as well as whether the latter has occurred in England.

Enantiospecific synthesis and filed evaluation of four stereoisomers of 10,14-dimethyloctadec-1-ene, a sex pheromone component secreted by female moths of the apple leafminer.

All four stereoisomers of 10,14-dimethyloctadec-1-ene, a sex pheromone component of the apple leafminer (Lyonetia prunifoliella: Lepidoptera), were synthesized starting from (R)- and (S)-propylene oxide by applying stereospecific inversion of chiral secondary tosylates as a key step. Field evaluation showed that male moths of the Japanese population were selectively attracted by the (10S,14S)-isomer and that the activity was not inhibited by the enantiomer.

Diagnostic molecular markers of six lepidopteran insect pests infesting apples in Korea

Two molecular identification techniques for differentiating six lepidopteran pests infesting apples in Korea are presented. These six species include two internal fruit feeders ( Grapholita molesta and Carposina sasakii), two leaf rollers ( Adoxophyes sp. and Archips breviplicanus) and two leaf miners ( Phyllonorycter ringoniella and Lyonetia prunifoliella). All species occur until near harvest and reduce apple production. A 489 bp fragment of mitochondrial cytochrome oxidase subunit I (COI) was sequenced in these six species. The sequence was used to select species-specific restriction enzyme sites and to design diagnostic polymerase chain reaction (PCR) primers, resulting in the development of restriction fragment length polymorphism (RFLP)-PCR and diagnostic PCR. These methods were reliable and rapid in the identification of these six species.

Lyonetiidae of Turkey with notes on their distribution and zoogeography (Lepidoptera)

Five species of Lyonetiidae are reported from Turkey: Lyonetia prunifoliella (Hübner, 1796), Lyonetia clerkella (Linnaeus, 1758), Leucoptera malifoliella (Costa, 1836), Bedellia somnulentella (Zeller, 1847), and Leucoptera laburnella (Stainton, 1851). The last was collected from Genista tinctoria in Ordu province and is considered a new pest in Turkey.

Catalytic Asymmetric Synthesis of Apple Leafminer Pheromones

Starting from cycloocta-2,7-dienone, all four diastereoisomeric 8-hydroxy-3,7-dimethyloctanoic acids were prepared in four steps (38% overall) and one of them (B) was transformed to pheromones C and D of the apple leafminer (Lyonetia prunifoliella) in a further four steps. A new method for the desymmetrization of cross-conjugated dienones is presented.

Insect semiochemical research in Korea: Overview and prospects

Rapid progress has been made in research on insect pheromones and other semiochemicals in Korea during the last two decades. Sex pheromone compositions have been identified in several major orchard and other horticultural moth pest species and some other species in Korea, such as Helicoverpa assulta, Grapholita molesta, Carposina sasakii, Adoxophyes orana, Lyonetia prunifoliella, Phyllonorycter ringoniella, Dichocrocis punctiferalis, Ostrinia furnacalis and Peridroma saucia. Some of these identified sex pheromones have already been successfully incorporated into IPM systems, and are now being used as direct and indirect pest control means in Korea. Korean populations of many of these species showed significant differences in pheromone compositions from those reported in the neighboring countries of Japan and China, suggesting that such interpopulational pheromone polymorphism is more common across the insect world than previously thought. Sex pheromone compositions were also identified in some aphid species in Korea such as Aphis spiraecola and Tuberocephalus momonis, and it was soon found that the aphid sex pheromone components were highly attractive to their predator lacewings. The presence of kairomones responsible for attracting egg parasitoids was shown in a pheromone component, hot pepper odor and male scale factor for H. assulta, and in male accessory glands for Lymantria dispar. Studies on the regulation of pheromone biosynthesis and release were carried out simultaneously in some species in Korea, resulting in the characterization of PBAN (pheromone biosynthesis activating neuropeptide) in H. assulta and Adoxophyes sp. A semiochemical research system has been firmly established in Korea through these studies. In some areas, successful monitoring and mating disruption technology have been effectively transferred from researchers to the end users in Korea, which will soon be expanded to wider areas. Continuous attempts to identify and use semiochemicals as well as wider applications of semiochemicals in pest control are expected in Korea in the coming years. Since Korean research on semiochemicals does not cover vast areas due to limited resources, focused research and practical application will be needed for selected target insect species.

Right stereoisomers for sex pheromone components of the apple leafminer, Lyonetia prunifoliella, in Korea.

The sex pheromone of the American population of Lyonetia prunifoliella (Lepidoptera: Lyonetiidae) was reported to be composed of three components, 10,14-dimethyloctadec-1-ene (10me14me-1-ene-18Hy), 5,9-dimethyloctadecane (5me9me-18Hy), and 5,9-dimethylheptadecane (5me9me-17Hy). Studies with a Korean population showed that the 10S, 14S isomer of the major compound was the major electrophysiologically by active stereoisomer. The 5S,9S isomers of the minar constituents also elicited electrophysiological responses. In field trappings, among the three components, the racemic mixture of 10me14me-1-ene-18Hy attracted L. prunifoliella males strongly, and the binary or tertiary combinations with racemic mixtures of the other two components did not increase trap catches. Among the four stereoisomers of 10me14me-1-ene-18Hy, only the 10S,14S isomer attracted L. prunifoliella males, as suggested by the EAG test, and attraction to the other three isomers was not observed. All stereoisomers of each minor component, as well as their racemic components, did not seem to have any additional effect on male attraction in Korea.

Mass flight activity of Lyonetia prunifoliella malinella (Lepidoptera: Lyonetiidae) with special reference to mating and dispersal.

During observations from September to November, flight activity of Lyonetia prunifoliella malinella occurred in the morning and in the evening outside the crowns of apple and shelter trees. The morning flight started about half an hour before sunrise. About 15 min later, the number of flying moths increased rapidly and swarms formed. The swarms lasted for about half an hour. Although females were present in the tree crown, they did not participate in the swarms, which were composed only of males. Mating began during the time when the males were swarming, and most of the mating pairs separated by noon. The evening flight started around sunset. It did not develop into swarms and finished in about half an hour. The evening flights were composed of both males and females, with the latter including both virgin and fertilized females. During the evening flight, it was noted that some moths were flying out of view. Simultaneously it was found that the moths flying into view alighted on the shelter trees. Thus, flight in the morning was considered to be associated with mating, while that in the evening with dispersal.

Synthesis of the Enantiomers ofanti-2,6-Dimethylheptane-1,7-diol Monotetrahydropyranyl Ether and Their Conversion into the Enantiomers of the Sex Pheromone Components of the Apple Leafminer,Lyonetia prunifoliella

Both (2R,6R)- and (2S,6S)-isomers of 2,6-dimethylheptane-1,7-diol monotetrahydropyranyl ether (4) were synthesized, and converted into the enantiomers of anti-10,14-dimethyl-1-octadecene (1), anti-5,9-dimethyloctadecane (2) and anti-5,9-dimethylheptadecane (3), the sex pheromone components of the apple leafminer (Lyonetia prunifoliella).

Sex Pheromone Components of the Apple Leafminer, Lyonetia prunifoliella

Three methylated hydrocarbons, 10,14-dimethyloctadec-1-ene (10Me14Me-1-ene-18Hy = 5Me9Me-17-ene-18Hy), 5,9-dimethyloctadecane (5Me9Me-18Hy), and 5,9-dimethylheptadecane (5Me9Me-17Hy), are synergistic sex pheromone components of the leafminer Lyonetia prunifoliella. Compounds extracted from female pheromone glands were identified by coupled gas chromatographic–electroantennographic detection (GC-EAD), and one compound, 10Me14Me-1-ene-18Hy, also by coupled GC–mass spectrometry. In field trapping experiments, 10Me14Me-1-ene-18Hy, 5Me9Me-18Hy, and 5Me9Me-17Hy singly were unattractive to males but in ternary combination attracted numerous male moths. Attractiveness of the three-component blend significantly exceeded that of two-component blends. No attraction of males to pheromone lures without 10Me14Me-1-ene-18Hy indicates that this compound is essential for pheromone communication of L. prunifoliella. Common C-5 and C-9 methyl branches in lyonetiid pheromone hydrocarbons suggest a common biosynthetic pathway; the presence of 5Me9Me-17Hy and 5Me9Me-18Hy in pheromone blends of L. prunifoliella and Leucoptera malifoliella provides evidence for phylogeny of lyonetiid chemical communication. Determination of the stereoisomeric composition is required to completely describe the pheromone blend of L. prunifoliella and to support the hypothesis of phylogenetically related sex pheromones.