SEX PHEROMONE OF THE POTATO TUBERWORM MOTH, PHTHORIMAEA OPERCULELLA: ISOLATION, IDENTIFICATION AND FIELD EVALUATION

Abstract

The sex pheromone of the potato tuberworm moth, Phthorimaea operculella (Zell.) has been identified as a mixture of trans‐4, cis‐7‐tridecadienyl acetate and trans‐4, cis‐1, cis‐10 tridecatrienyl acetate. The identifications have been carried out by means of electroantennography, mass, infrared and n.m.r. spectroscopy. The identifications have been confirmed by synthesis. Both compounds occur in the insects in about equal amounts. The individual compounds are attractive to male moths in pheromone traps. The triolefinic ester was found to be much more attractive than the diolefinic ester. However, mixtures of both compounds in the ranges of 4:1 tot 1:4 are much more attractive than the individual compounds or traps baited with two virgin female moths. ZUSAMMENFASSUNG SEXUALPHEROMONE DER KARTOFFELMOTTE, PHTHORIMAEA OPERCULELLA. ISOLIE‐RUNG, IDENTIFIKATION UND FREILANDBEWERTUNG Das Sexualpheromon von Phthorimaea operculella (Gelechiidae) wurde identifiziert als ein Gemisch von trans‐4, cis‐7‐Tridecadienylacetat und trans‐4, cis‐1, cis‐10‐Tridecatrienylacetat. Die beiden Identifizierungen wurden durchgeführt mit Hilfe von Elektroantennografie, Massenspektroskopie, Ultrarotspektroskopie und Kernspinnresonanzspektroskopie. Die beiden Identifizierungen wurden durch Synthese bestätigt. Die Pheromonkomponenten wurden in etwa gleiche Mengen von den Faltern isoliert. Beide Substanzen erwiesen sich sowohl in natürlicher wie in synthetischer Form als aktiv in der Elektroantennografie sowie im biologischen Test und in Sexfallen. Ein Mischungsverhältnis der beiden Komponenten von 4: 1 bis 1: 4 weist eine viel höhere Lockstoffwirkung auf als die beiden Einzelkomponenten oder als zwei lebende Weibchen. Ein Isomer des natürlichen Tridecatrienylacetat, nämlich cis‐4, trans‐7, cis‐10‐Tridecatrienyl‐acetate, war nur schwach aktiv in den verschiedenen Testen. In Sexfallen wurde die Aktivität dieses Isomers durch Zusatz von trans‐4, cis‐7‐Tridecadienylacetat nicht erhöht.

Lepidopteran Sex Pheromones

“…56 T. Ando et al The straight chain is dominantly formed with even-numbered carbons because the Type I compounds are derived de novo via general saturated fatty acids such as palmitic acid (16:Acid) and stearic acid (18:Acid). However, exceptions do exist as pheromone components with an odd number chain have been determined from six species: E4,Z7-13:OAc and E4,Z7,Z10-13:OAc from P. operculella, [11], E4-13:OAc from the tomato pinworm (Keiferia lycopersicella, Gelechiidae) [12], E3-13:OAc from the tobacco stem borer (Scrobipalpa heliopa, Gelechiidae) [13], Z8-13:OAc and Z10-15:OAc from the sugarcane stalk borer (Chilo auricilius, Pyralidae: Crambinae) [14], E8,Z10-15:OAc and E9-15:OAc from the cranberry fruitworm (Acrobasis vaccinii, Pyralidae: Phycitinae) [15], and Z11-17:OAc from the cabbage armyworm (Mamestra brassicae, Noctuidae: Hadeninae) [16]. Figure 3A shows the location of the double-bond relative to a functional group of the Type I monoenyl components.…”

Biological Activity of Essential Oils from Leaves and Fruits of Pepper Tree (Schinus molle L.) to Control Rice Weevil (Sitophilus oryzae L.)

“…Afterwards, research by Fouda et al (1975Fouda et al ( ), (1975, Roelofs et al (1975), Persoons et al (1976), Yamoaka et al (1976), Bacon et al (1976), Voerman et al (1977, Voerman and Rothschild (1978), identified, isolated, and synthesized the two main pheromone compounds, finding that combining them attracted the male moths more than each compound taken separately. Bacon et al (1976) and Raman (1982; also evaluated the most effective rates of these two compounds in the mixture preparation, as well as some techniques to use these compounds in field and storage traps.…”

The Potato Tuberworm: A Literature Review of Its Biology, Ecology, and Control

“…According to Herman et al (2005), two chemicals have been identified as the main component of P. operculella sex pheromone: (E4,Z7)-tridecadienyl acetate (PTM1) (Roelofs et al 1975) and (E4,Z7,Z10)-tridecatrienyl acetate (PTM2) (Persoons et al 1976); both chemicals were synthesized, blended, and tested (Voerman and Rothschild 1978;Raman 1988). Since some other insects, including other Gelechiidae moths could be trapped in the sticky liners, they should be changed once a week for easy viewing of adult moths; lures should be changed monthly but may be used longer, depending on environmental conditions; at cooler temperatures the longevity of the lures increases (Rondon et al 2007).…”