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J Chem Ecol

Title:		European corn borer sex pheromone : Structure-activity relationships
Author(s):		Schwarz M; Klun JA; Fritz GL; Uebel EC; Raina AK;
Address:		"Insect Chemical Ecology Laboratory Agricultural Research Service, USDA, 20705, Beltsville, Maryland"
Journal Title:		J Chem Ecol
Year:		1989
Volume:		15
Issue:		2
Page Number:		601 - 617
DOI:		10.1007/BF01014704
ISSN/ISBN:		0098-0331 (Print) 0098-0331 (Linking)
Abstract:		"The biological activity of analogs of the pheromone components of the European corn borer,Ostrinia nubilalis, (Z)- and (E)-11-tetradecen1-ol acetate, in which modifications were made in the terminal alkyl portion were studied in the three pheromonal types of the insect. European corn borer males respond to pheromonal stimuli at three levels of behavioral activity, i.e., short-range sexual stimulation, activation in the flight tunnel, and response in the field. Structural requirements for elicitation of response at these levels were found to be increasingly restrictive, respectively. Flighttunnel activity was induced only by compounds that had a total chain length of 13 or 14 carbons and in which branching at carbon 13 was limited to one methyl group or a cyclopropyl group. Three new analogs were active in the flight tunnel, viz., (E and (Z)-13-methyl-11-tetradecen-1-ol acetate and (Z)-12-cyclopropyl-11-dodecen-1-ol acetate. The cyclopropyl analog was the most active analog against theZZ type of the European corn borer. TheE isomer, however, was pheromonally inactive in theEE type and was shown to be a pheromone antagonist. This dissimilarity is most likely due to differences in structure of the receptors in the European corn borer strains. Analogs that were biologically active against the European corn borer were tested against the redbanded leafroller,Argyrotaenia velutinana, which also uses (Z)- and (E)-11-tetradecen-1-ol acetate as part of its pheromone. Results showed that the redbanded leafroller pheromone acceptor system is different from that of the European com borer; marginal behavioral response was elicited by only one of the new analogs. Thus, although both species use 11-tetradecen-1-ol acetate isomers as their pheromone, the mechanisms by which they are perceived are different"
Keywords:
Notes:		"PubMed-not-MEDLINESchwarz, M Klun, J A Fritz, G L Uebel, E C Raina, A K eng 1989/02/01 J Chem Ecol. 1989 Feb; 15(2):601-17. doi: 10.1007/BF01014704"