(Z)-11-Hexadecenal and (3Z,6Z,9Z)-Tricosatriene: Sex Pheromone Components of the Red Banded Mango Caterpillar Deanolis sublimbalis

Abstract

The sex pheromone of the red banded mango caterpillar, Deanolis sublimbalis (Lepidoptera: Crambidae), a serious pest of the mango Mangifera indica (Anacardiaceae) in India and Southeast Asia and a recent invader into northern Australia, has been identified. Three candidate compounds were identified from pheromone gland extracts of female moths, using gas chromatography (GC), GC-electroantennographic detection and GC-mass spectrometric analyses, in conjunction with dimethyldisulfide derivatization. Field bioassays established that both (Z)-11-hexadecenal (Z11-16:Ald) and (3Z,6Z,9Z)-tricosatriene (3Z,6Z,9Z-23:Hy) were required for attraction of male D. sublimbalis moths, and 1000 microg of a 1:1 mix of Z11-16:Ald and 3Z,6Z,9Z-23:Hy was more attractive to male moths than caged virgin females. However, the binary blend was only attractive when the isomeric purity of the monounsaturated aldehyde was >99%, suggesting that the (E)-isomer was inhibitory. Although (Z)-11-hexadecen-1-ol (Z11-16:OH) was tentatively identified in gland extracts, the addition of this compound to the binary blend did not increase the numbers of moths captured. The pheromone can now be used in integrated pest management strategies.

Monoenyl hydrocarbons in female body wax of the yellow peach moth as synergists of aldehyde pheromone components

“…Most lepidopteran pheromones are known to consist of multi-components that are classified into the type I group including alcohols, acetates and aldehydes; the type II group with unsaturated hydrocarbons or their epoxy derivatives; and miscellaneous pheromone components that are classified as neither type I nor type II (Ando et al 2004). Meanwhile, both type I and type II compounds are also used together as the sex pheromones of several species (Hill and Roelofs 1981;Hill et al 1982;Cabrera et al 2001;Leal et al 2005;Millar et al 2005;Gibb et al 2007). Compounds in both the type I and type II groups of lepidopteran sex pheromones have been identified in pheromone extracts obtained by extracting the female's abdominal tips containing the sex pheromone glands.…”

Alkenyl sex pheromone analogs in the hemolymph of an arctiid Eilema japonica and several non-arctiid moths

“…T23 and other type-II alkenes have recently been identified in the pheromone gland or body surface wax of five crambid species: Neoleucinodes elegantalis (Cabrera et al, 2001), Conogethes pluto (EI-sayed et al, 2013), Conogethes punctiferalis (Xiao et al, 2012), Deanolis sublimbalis (Gibb et al, 2007), and Omphisa anastomosalis (Yan et al, 2014). In C. punctiferalis, Xiao et al (2012) demonstrated that the addition of T23 enhanced the activity of the aldehyde pheromone blend (a mixture of E10-16:Ald and 11 Z10-16:Ald) by increasing the time spent close to the source as well as the number of source contacts.…”

Non-polar body waxes enhance sex pheromone activity in the yellow peach moth, Conogethes punctiferalis (Guenée) (Lepidoptera: Crambidae)

“…In many cases, pheromone components are chemicals within the same group; however, both Type I and Type II compounds are used together in the sex pheromones of several species (Hill and Roelofs, 1981;Hill et al, 1982;Cabrera et al, 2001;Leal et al, 2005;Millar et al, 2005;Gibb et al, 2007). These different types of chemical components appear to have different functions in their pheromone systems when tested separately because some Type II components singly attract no males to the pheromone source in a wind tunnel or display low or no attractiveness in the field (Cabrera et al, 2001;Gibb et al, 2007); however, mixtures of these components with Type I components exhibit significant attractiveness in both wind tunnel (Hill and Roelofs, 1981;Hill et al, 1982) and field tests (Millar et al, 2005;Gibb et al, 2007). In the yellow peach moth, a non-polar fraction of the crude pheromone extracts also elicited no male behavioral responses, except starting flight, when tested singly, but when this fraction was mixed with the polar fraction of female pheromone extracts or the synthetic blend, significantly higher response levels were evoked in all behavioral categories in the wind tunnel test.…”