Extracellular recordings show that the response to the sex pheromone component, (Z)-7-dodecenyl acetate (Z7–12:Ac) by the HS(a) antennal olfactory specialist neuron of the cabbage looper,Trichoplusia ni (Hübner), is synergized by two synthetic sex pheromone analogs and two components of the female sex pheromone. Complementary behavioral measures of upwind flight and copulatory responses to mixtures ofZ7–12:Ac with the analogs and sex pheromone components in a wind tunnel produced behavioral evidence consistent with the neuron's electrophysiological responses. The phenomenon of receptor neuron synergism impacts several areas and provides a note of caution for common practices of identifying secondary sex pheromone components only from field traps and/or wind tunnel tests.

tert-Butyl 4- (and 5-) chloro-trans-2-methylcyclohexane-1-carboxylate (TML), a mixture of four majortrans and four minorcis isomers, is used as an attractant for detecting and monitoring the male Mediterranean fruit fly (medfly),Ceratitis capitata (Wiedemann). The eight isomers (racemic mixtures) were isolated by HPLC, and their relative attractiveness in the field was determined. A quantitative structure-activity relationship (QSAR) was proposed that related a molecular measurement (Å3) of the TML structure to male medfly captures. More recently, thetrans-TML enantiomers were synthesized in sufficient quantities for field testing. This paper reports the computer-aided molecular modeling, via Chem-X, of thetrans-TML enantiomers and the staggered and superimposed fitting with the most attractive isomer, (1S,2S,4R)-TML-C, to determine common volumes and surface areas from Van der Waals (VdW) maps. Observations of structure-activity relationships (SAR) are reported for the staggered fittings.

The most biologically active enantiomer of trimedlure, a synthetic lure attractive to male Mediterranean fruit flies, is the 1S,2S,4R enantiomer of isomer C, the fert-butyl ester of ris-4-chloro-trans-2-methylcyclohexanecarboxylic acid. We also determined that the 1R,2R,5S enantiomer of isomer A is significantly more attractive than its optical antipode. Essential differences in the current synthetic work that are critical to possible commercialization of this preparation are detailed herein.

Three major components, ethyi-(E)-3-octenoate, geranyl acetate, and (E,E)-α-farnesene, emitted as volatiles by laboratory-reared and wild male medflies were collected and analyzed qualitatively and quantitatively. Peak emission of these compounds occurred during the third to fifth hours of the photophase and differences were observed in the ratios of the three components emitted by male laboratory-reared and wild flies. These three compounds were synthesized, and a method was developed to formulate a synthetic blend that released the compounds in a ratio similar to that emitted by wild male medflies. Attractiveness of the blend to female medflies was demonstrated under field conditions by comparing trap catches. Black spherical traps, baited with the synthetic blend to release 1.6 male equivalents, caught significantly more females than blank traps and traps from which the blend released was 0.3, 3.2 or 6.4 male equivalents.

Three isomeric conjugated triene aldehydes,(10E,12E,14Z)-10, 12-14-hexadecatrienal (IX), (10E,12Z,14E)-10,12,14-hexadecatrienal (XX), and (10E,12E,14E)-10,12,14-hexadecatrienal (X), two of which are components of theManduca sexta (L.) sex pheromone, have been stereoselectively synthesized and spectroscopically characterized.

A sex pheromone produced by female banded cucumber beetle adults,Diabrotica balteata LeConte, was isolated from volatiles trapped on Porapak Q and identified as 6,12-dimethylpentadecan-2-one. The structure was elucidated by spectroscopic analyses and confirmed by synthesis. The synthesized racemic compound was equal to the purified natural pheromone in eliciting responses by banded cucumber beetle males to field traps. A doseresponse characteristic was demonstrated for the racemic material formulated on filter paper or rubber septa and placed in field traps. The absolute configuration at the C-6 and C-12 positions was not established.

A new efficient stereoselective synthesis for (Z,E)-3,5-tetradecadienyl acetate (Z3,E5–14∶Ac) a potent male sex attractant for the carpenterworm,Prionoxystus robiniae (Peck), was developed. The effects of the other three isomers (Z,Z; E,Z; E,E) on the field attractiveness of theZ,E isomer toward maleP. robiniae were determined. TheZ, Z isomer inhibited attraction, theE, E isomer synergized attraction, and theE,Z isomer had no effect on attraction. Seven monounsaturated 14-carbon acetates were evaluated for their effect on the attractiveness ofZ3,E5–14∶Ac. (E)-3-Tetradecenyl acetate enhanced attraction and (Z)-9- and (E)-5-tetradecenyl acetate reduced trap captures. (Z,E)-3,5-Tetradecadien-1-ol also reduced the attractiveness ofZ3,E5–14∶Ac.

Abstract2,4‐Diinole (I) werden mit n‐Butyllithium/Di‐isobutyl‐aluminiumhydrid selektiv zu 2‐En‐4‐inolen (II) reduziert, während mit Lithiumaluminiumhydrid aus (Ia) ein Gemisch der Reduktionsprodukte (IIa) und (III) entsteht.

Several compounds were tested for disruption of sex pheromone communication in Amyelois transitella (Walker). Catches of males in female-baited traps were significantly reduced by in-trap treatments with (Z)-9- and (Z)-11-tetradecen-1-ol formate and isomers of 9, 11-tetradecadien-1-ol formate. Disruption by air permeation with (Z, Z)-9,11, tetradecadien-1-ol formate was better with a plastic laminate formulation than hollow fibers or polyvinyl-chloride rods but was still inferior to treatments with the navel orangeworm pheromone (Z, Z)-11, 13-hexadecadienal.

Journal Article Disruption of Mating in the Navel Orangeworm with ( Z , Z )-11,13-Hexadecadienal Get access P. J. Landolt, P. J. Landolt 4 Agricultural Research, Science and Education Administration, U.S. Department of Agriculture 4 Stored Product Insects Research Laboratory, 5578 E. Air Terminal Drive, Fresno, CA 93727. Search for other works by this author on: Oxford Academic PubMed Google Scholar C. E. Curtis, C. E. Curtis 4 Agricultural Research, Science and Education Administration, U.S. Department of Agriculture 4 Stored Product Insects Research Laboratory, 5578 E. Air Terminal Drive, Fresno, CA 93727. Search for other works by this author on: Oxford Academic PubMed Google Scholar J. A. Coffelt, J. A. Coffelt 5 Agricultural Research, Science and Education Administration, U.S. Department of Agriculture 5 Insects Atractants Research Loboratory. P.O. Box 14565, Gainesville, FL 32604. Search for other works by this author on: Oxford Academic PubMed Google Scholar K. W. Vick, K. W. Vick 5 Agricultural Research, Science and Education Administration, U.S. Department of Agriculture 5 Insects Atractants Research Loboratory. P.O. Box 14565, Gainesville, FL 32604. Search for other works by this author on: Oxford Academic PubMed Google Scholar P. E. Sonnet, P. E. Sonnet 5 Agricultural Research, Science and Education Administration, U.S. Department of Agriculture 5 Insects Atractants Research Loboratory. P.O. Box 14565, Gainesville, FL 32604. Search for other works by this author on: Oxford Academic PubMed Google Scholar R. E. Doolittle R. E. Doolittle 5 Agricultural Research, Science and Education Administration, U.S. Department of Agriculture 5 Insects Atractants Research Loboratory. P.O. Box 14565, Gainesville, FL 32604. Search for other works by this author on: Oxford Academic PubMed Google Scholar Environmental Entomology, Volume 10, Issue 5, 1 October 1981, Pages 745–750, https://doi.org/10.1093/ee/10.5.745 Published: 01 October 1981 Article history Received: 22 October 1980 Published: 01 October 1981

A combination of the synthetic sex attractant (R,Z)-5-(1-decenyl) dihydro-2(3H)-furanone with a 3∶7 mixture of phenethyl propionate (PEP) and eugenol (4-allyl-2-methoxphenol) caught significantly morePopillia japonica Newman than either the sex attractant or the mixture did alone. Also, the synthetic sex attractant captured significantly more males than the PEP-eugenol did during the period of heavy adult emergence of the beetles. The two lures were not significantly different in their attractancy to males about a week later and thereafter. A combination of PEP-eugenol and virgin females in the same trap late in the season also significantly increased beetle captures.

The sex pheromones produced by females of the lesser peachtree borer,Synanthedon pictipes (Grote and Robinson), and the peachtree borer,Synanthedon exitiosa (Say), (E,Z)- and (Z,Z)-3,13-octadecadien-1-ol acetate, respectively, were synthesized from 1,8-dichlorooctane, lithium acetylide, and ethylene oxide. In the course of the synthesis a new carbon-oxygen cleavage reaction of homopropargylic acetals was found, and the stereochemistry of the dissolving metal reductions of acetylenic alcohols was investigated.

The stereospecific synthesis of the sex pheromone produced by the female Japanese beetle (Popillia japonica Newman), (R,Z)-5-1-decenyl)-dihydro-2(3H)-furanone, is described. The pure syntheticR,Z form is a powerful attractant for males of the species in field bioassays and was competitive in attractiveness with live females, whereas the racemicZ isomer and theS,Z enantiomer were strong inhibitors of male response. The saturated analogs of both enantiomers were also synthesized stereospecifically.