Identification and field evaluation of sex pheromone components of the pear barkminer moth, Spulerina astaurota.

The pear barkminer moth, Spulerina astaurota Meyrick (Gracillariidae: Gracillariinae), is a harmful pest of the Asian-pear tree. Pheromone components of the female were analyzed by gas chromatography (GC) with an electroantennographic (EAG) detector and GC coupled with mass spectrometry. The analyses of a crude pheromone extract and those of a fractionated extract on a Florisil column indicated three EAG-active components, tetradecadien-1-ol, its acetate, and an aldehyde derivative.

Novel components of the sex pheromones produced by emerald moths: identification, synthesis, and field evaluation.

The subfamily Geometrinae (Lepidoptera: Geometridae) includes many species called emerald moths. Based on our recent finding of novel polyenyl compounds, including a double bond at the 12-position from two geometrine species, Hemithea tritonaria and Thalassodes immissaria intaminata, (6Z,9Z,12Z)-6,9,12-trienes and (3Z,6Z,9Z,12Z)-3,6,9,12-tetraenes with a C(17)-C(20) straight chain were synthesized and analyzed by GC-MS. The 6,9,12-trienes, which were prepared by a double Wittig reaction between two alkanals and an ylide derived from (Z)-1,6-diiodo-3-hexene, characteristically produced fragment ions at m/z 79, 150, and M-98.

Sex pheromone components and control of the citrus pock caterpillar, Prays endocarpa, found in the Mekong Delta of Vietnam.

The citrus pock caterpillar, Prays endocarpa (Yponomeutidae; Praydinae), is a pest of pomelo (Citrus grandis L.) in Vietnam. Gas chromatography-mass spectrometry analyses of pheromone gland extracts from female moths identified three monoenyl compounds, (Z)-7-tetradecenal (Z7-14:Ald), (Z)-7-tetradecenyl acetate (tentatively identified, Z7-14:OAc), and (Z)-7-tetradecen-1-ol (Z7-14:OH), in a ratio of about 10:3:10.

Female sex pheromone of Glossosphecia romanovi (Lepidoptera: Sesiidae): identification and field attraction.

In field screening tests of synthetic pheromone candidates for Japanese sesiid species, a mixture of (3Z,13Z)-octadecadien-1-ol and (3Z,13Z)-octadecadienyl acetate successfully attracted male moths of Glossosphecia romanovi, a harmful pest of vine trees. The GC-EAD and GC-MS analyses of the pheromone gland extract revealed that the female moths produced the alcohol and acetate in a ratio of about 20:1, in addition to three other minor structure-related components.

Positions and stereochemistry of methyl branches in the novel sex pheromone components produced by a lichen moth, Lyclene dharma dharma.

Female moths of Lyclene dharma dharma (Arctiidae, Lithosiinae) produce three sex pheromone components (I-III), for which we assigned the following novel chemical structures; 6-methyl-2-octadecanone (1) for I, 14-methyl-2-octadecanone (2) for II, and 6,14-dimethyl-2-octadecanone (3) for III. In the Iriomote Islands where the insects were collected, a lure including racemic 1 and 2 attracted the male moths without mixing 3. In this study for further confirmation of the plane structures, the positional isomers with a methyl branch at the 4-, 5-, 7-, 13-, or 15-position (4-8, respectively) were synthesized.

Synthesis and field evaluation of methyl-branched ketones, sex pheromone components produced by Lithosiinae female moths in the family of Arctiidae.

Female moths of Lyclene dharma dharma (Arctiidae, Lithosiinae) produce a novel sex pheromone composed of three methyl-branched ketones (I-III) in a ratio of 2:1:1. In order to confirm the structure of III (6,14-dimethyl-2-octadecanone), a mixture of its four stereoisomers was synthesized via chain elongation by two Wittig reactions, starting from 1,7-hexanediol. GC-MS data of the synthetic III were satisfactorily coincident with those of the natural component.

Instrumental analysis of terminal-conjugated dienes for reexamination of the sex pheromone secreted by a nettle moth, Parasa lepida lepida.

Conjugated dienyl compounds make one of the main groups of lepidopteran sex pheromones, and GC has been frequently used to determine the configurations of the double bonds. However, the separation of two geometric isomers of a terminal-conjugated diene, such as 7,9-decadien-1-ol secreted by a nettle moth Parasa lepida lepida (Limacodidae), is assumed to be difficult. In order to clarify the chromatographic separation of the terminal dienes, 7,9-decadienyl and 9,11-dodecadienyl compounds (alcohols, acetates, and aldehydes) were analyzed by GC and HPLC.

A novel lepidopteran sex pheromone produced by females of a Lithosiinae species, Lyclene dharma dharma, in the family of Arctiidae.

Female moths of Lyclene dharma dharma (Arctiidae, Lithosiinae) produced three pheromone components (I-III), which strongly stimulated male antennae. Using GC-MS analysis and chemical derivatizations, the following structures were estimated: 6-methyl-2-octadecanone (I), 14-methyl-2-octadecanone (II), and 6,14-dimethyl-2-octadecanone (III). While the stereochemistry of the chiral centers could not be determined because it was difficult to collect a sufficient amount of the natural pheromone, the plain structures of I and II were confirmed by synthesis of the racemic mixtures starting from diols.