Lepidopteran Sex Pheromones

Abstract

As a consequence of the diversity of Lepidoptera, including 150,000 described species, interesting species-specific sex pheromone systems are exhibited in this insect group. The quite varied pheromones, which have been identified from female moths of nearly 530 species from around the world, are classified into groups of Type I (75%), Type II (15%), and miscellaneous (10%), according to their chemical structures. Additionally, many pheromones produced by male moths and butterflies have been known. While new sex pheromones from about 70 lepidopteran species have been reported in the last five years utilizing GC-EAD, GC-MS, LC, and NMR, our information about the pheromones is still rudimentary, and these kinds of semiochemicals remain an exciting research target for natural product chemistry. In addition to the overview of their chemical structures, this chapter deals with current methods for their identification. Furthermore, an actual application of the synthetic pheromones for pest control is briefly introduced.

The chemical volatiles (Semiochemicals) produced by neotropical stink bugs (Hemiptera: Pentatomidae)

“…In contrast to the Lepidoptera, the Pentatomidae do not show a structural pattern of the compounds following families or subfamilies. For Lepidoptera it is possible to classify the pheromones into either type I (75%), which are long, straight chain (C 10 -C 18 ) alcohols and their derivatives, mainly acetates and aldehydes; type II (15%), which are polyunsaturated hydrocarbons and their epoxy derivatives with a longer straight chain (C 17 -C 23 ); or miscellaneous (10%) (Ando et al 2004). However, for some species of Pentatomidae it is possible to observe a characteristic structural pattern at the genus level.…”

GC/FT-IR Analysis of Novel 4,6,9-Triene and 2,4,6,9-Tetraene Occurring in a Female Pheromone Gland of <i>Arctia plantaginis</i> (Erebidae: Arctiinae)

“…I -IV are classified into Type II pheromone compounds, unsaturated hydrocarbons and their epoxy derivatives with a C 17 -C 25 straight chain, which are biosynthesized from linoleic and linolenic acids included in dietary plants [2]. Z3,Z6,Z9-21:H has been identified from many moth species in the families of Erebidae, Geometridae, and Crambidae, and 1,Z3,Z6,Z9-21:H has been identified from four Arctiinae species and one Geometridae species [5] [6].…”

“…Lepidopteran pheromones have usually been investigated by gas chromatography (GC) with an electroantennographic (EAG) detector (GC-EAD) and GC combined with mass spectrometry (GC/MS) [2]. GC-EAD can differentiate biologically active compounds from others in the crude extract, and then chemical structures of the pheromone candidates are identified by GC/MS [8].…”

7,11,13-Hexadecatrienal identified from female moths of the citrus leafminer as a new sex pheromone component: synthesis and field evaluation in Vietnam and Japan

“…The mixing ratio of the two geometrical isomers was about 2 : 1, and an aliquot of the mixture was supplied to preparative HPLC with an ODS column to separate the isomers (Z7,Z11,E13-16:OH t R 32. 5 …”

“…Although some trienyl compounds have been identified, this identification is the first case of pheromone components with a 7,11,13-trienyl structure. 5,6) We had an interest in the activity of the new compound against Asian strains, including Japanese ones, and synthesized Z7,Z11,E13-16:Ald and its geometrical isomer. This report presents their synthesis and field evaluation in citrus orchards in Japan and Vietnam.…”