Arnon Shani

Abstracts of papers presented at

S OF PAPERS P R E S E N T E D AT THE 5th MEETING ON PHEROMONE RESEARCH IN ISRAEL

Characteristics and some potential applications of date palm (Phoenix dactylifera L.) seeds and seed oil

The seeds of four date palm (Phoenix dactylifera L.) cultivars, Dekel Noor, Zahidi, Medjool and Halawy, grown in the Arava Valley of southern Israel were analyzed for their inorganic and some organic constituents. The following average values were obtained for the four cultivars on a dry-weight basis: protein 5.60%, oil 8.15%, fiber 16.13%, and ash 1.13%. Analysis of the mineral elements in the ash gave the following average values: Ca, 1.55%; Na, 0.97%; Mg, 8.07%; K, 27.60%; Fe, 0.73%; Cu, 0.13% and Mn, 0.08%. The oil exhibited the following characteristics (average for the four cultivars): acid value ∼1.04, iodine value 49.5, saponification value 221.0, and unsaponifiable matter 0.8%. Gas-liquid chromatography revealed that the major unsaturated fatty acid was oleic acid (42.3%), while the main saturated fatty acid was lauric (21.8%). Myristic, palmitic and linoleic acids were also found, average values being 10.9, 9.6 and 13.7%, respectively. Potential uses for date seed oil are considered for cosmetic, pharmaceutical and related specialty products, and to a lesser degree for food products.

Variation in relative quantities of airborne sex pheromone components from individual femaleEphestia cautella (Lepidoptera: Pyralidae)

The airborne sex pheromone components (Z,E)-9,12-tetradeca-dien-1-yl acetate and (Z)-9-tetradecen-1-y1 acetate from single calling females ofEphestia cautella (Walker) were trapped within glass capillary tubes and were measured by gas chromatography-mass spectrometry. Broad and similar distributions of relative quantities were found for a laboratory strain and three Australian field strains, and means differed strongly from those reported previously for this species. The overall mean proportion of the two components found for Australian females was 88∶12. The composition in individuals ranged from 63∶27 to 97∶3. The proportions for individuals appeared to vary slightly in a random fashion from day to day, and proportions for first-generation progeny were influenced by the maternal blend.

On the mechanism of intramolecular photocycloaddition of substituted o-allylphenols to cyclic ethers

Abstract Osmometric and NMR techniques were used in order to study the ionic mechanism for the intramolecular photocycloaddition reaction of o -allyl phenols ( 1 ) to give cyclic ethers ( 2 ) + ( 3 ). The role of the intramolecular H-bond between the OH group and the π-electrons of the allylic group was ascertained. based on the results of the photocyclization, osmometric and NMR measurements the substituents can be divided into 3 groups according to their effect on the above intramolecular interaction.

The Wittig reaction: comments on the mechanism and application as a tool in the synthesis of conjugated dienes

Abstract For construction, by the Wittig reaction, of conjugated dienes with specific stereochemistry (either Z or E ) at the newly formed double bond, without isomerization of the existing (“old”) double bond, it is better to react a reactive (nonstabilized) saturated ylide with an α, β-unsaturated aldehyde. The opposite approach, namely, the reaction of a moderate (semi-stabilized) allylic ylide with a saturated aldehyde produces a mixture of geometric isomers, as a result of increased production of the E -configuration at the new double bond, and significant isomerization of the existing double bond. The proposed betaine structure for the intermediate could account only for the two equivalents of Li reaction. In other reactions, the less stable erythro-oxaphosphetane is probably the intermediate, produced by an early anti- or gauche CC bond formation from the ylide and the carbonyl, from which the Z-double bond is then formed.

Olfactory response by the aphidophagous gall midge, Aphidoletes aphidimyza to honeydew from green peach aphid, Myzus persicae

Female adults of the aphidopagous gall midge, Aphidoletes aphidimyza (Rondani) (Diptera: Cecidomyiidae), showed an olfactory response to honeydew excreted by the green peach aphid, Myzus persicae (Sulzer) (Hemiptera: Aphididae) under laboratory conditions. The response was only elicited by treatments with honeydew, whereas aphids, aphids with pepper plants or leaves, and pepper plants or leaves were not attractive to the midges. Dose‐dependent responses were observed from whole honeydew, honeydew volatiles extracted in pentane, and honeydew volatiles captured on Porapak Q®. When honeydew was eluted with three sequential pentane washes, a positive response was only observed from the midges for the first wash. Female midges laid more eggs on pepper plants infested with higher densities of M. persicae. The olfactory response of midges to honeydew is discussed with respect to prey location.

Metal sorption properties of sulfur-chlorinated jojoba wax bound to polystyrene beads

A new solid extractant (designated PS-DETA-JS) in which sulfur-chlorinated jojoba wax is bound via an amine spacer group to polystyrene beads was synthesized. The absorption of mercury cations from acidic solutions and of chromate anions from saline solutions onto PS-DETA-JS was investigated. The sorption of mercury ions by the solid extractant was compared with that by liquid-sulfurized jojoba wax impregnated inside macroporous resins. The static and dynamic properties of dichromate sorption from 2-20 g/L NaCl solutions at pH 4.1 were studied. Selective sorption of Cr(VI) ) was obtained at low chromate concentrations ( 6 ppm) in saline aqueous solutions. Complete regeneration of the PS-DETA-JS resin was achieved after the reduction of Cr( VI ) to Cr ( III ) and the elution of the Cr(III) ) with 1N HCl.

Chemical protection of pheromones containing an internal conjugated diene system from isomerization and oxidation

Conjugated diene systems are common in natural products, including pheromones. The systems are sensitive to heat, light, and oxygen, among other things. They can be protected by antioxidants and UV absorbers, which slow downcis-trans isomerization and oxidation. Three sex pheromones (one as an analog) containingZ,E, E,Z, andE,E units were studied: (Z,E)-9,11-C14OAc, (E,Z)-7,9-C12OAc, and (E,E)-10,12-C16OAc. The UV absorber 2-hydroxy-4-methoxybenzophenone and the antioxidants BHT and BHA were found to be effective in solution. The protective effect of the UV absorber against photoisomerization on paper carriers was not as good as that in solution. Preliminary studies on the utilization of formulations containing these compounds and (Z,E)-9,11-C14OAc in the mass trapping of Egyptian cotton leafworm male in cotton fields showed the new combinations to be as good as a previously used formulation with UOP 688, a compound which is unpleasant to handle.

(Z,E)-α-Farnesene—An electroantennogram-active component of Maladera matrida volatiles

Abstract It has previously been shown in field-trapping experiments and laboratory olfactometer bioassays that virgin females of Maladera matrida Argaman (Coleoptera, Scarabaeidae) and their volatiles, both in the presence of food (cut peanut leaves), are efficient attractants for M. matrida males and females. In this study GC-EAD experiments using male antennae and GC-MS experiments revealed that ( Z , E )- α -farnesene is an active component of M. matrida female volatiles. The identification and quantitative electrophysiological responses (EAG) of synthetic ( Z , E )- α -farnesene were obtained with male and female antennae. It was also shown that Z , E )- α -farnesene is not a component of the plant volatiles that serve as synergistic components of the mixture of attractants or of the source of food for M. matrida .

Trimerization ofEarias insulana sex pheromone, (E,E)-10,12-Hexadecadienal, A phenomenon affecting trapping efficiency

The sex pheromone ofEarias insulana, (E,E)-10,12-hexadecadienal, may trimerize extensively to form a crystalline trioxane derivative. The structure of the trimer was deduced from its CI-MS and NMR spectra. Capillary GC analysis resulted in the thermal decomposition of the trimer to the monomer. This process could be studied on a 2-m packed column under specific conditions. A convenient separation between the pheromone and its trimer was achieved by TLC. The trimer was inactive in the field, and it has a harmful effect on the performance of the polyethylene dispenser. Material which contains large amounts of the trimer is unsuitable for field use, even if applied at high dosage. The pheromone should be analyzed by NMR or TLC in addition to GC in order to detect the presence of its trimer. The trimerization process is catalyzed by acid which should therefore be completely eliminated from the storing vessels.