Evidence of pheromonal constancy among sexual and asexual females in a population of fall cankerworm,Alsophila pometaria (Lepidoptera: Geometridae)

The compounds (Z,Z,Z)-3,6,9-nonadecatriene (I), (Z,Z,Z,E)-(II), and (Z,Z,Z,Z)-3,6,9,11-nonadecatetraene (III) have been implicated as components of the female sex pheromone of the fall cankerworm. Chromatographie determination of the proportions of these compounds in individual females of sympatric asexual and sexual reproductive forms of the species, with concurrent analysis of the electrophoretic profiles of the same females, showed that the I: II: III proportion of compounds was constant across electrophoretically differing asexual genotypes and between these and the sexual form. Life-history characters, in contrast, typically show great variation among these genetic groups. The results indicate that pheromonal constancy is maintained in a reproductive system that is theoretically vulnerable to selective pressures that would lead to heterogeneity in the species' pheromonal communication channel.     

Sex pheromone of the saltmarsh caterpillar moth,Estigmene acrea

Three compounds have been identified as components of the sex pheromone emitted by females of the saltmarsh caterpillar moth,Estigmene acrea (Drury). These are (Z,Z)-9,12-octadecadienal (I), (Z,Z,Z)-9,12,15-octadecatrienal (II), and (Z,Z)-3,6-cis-9,10-epoxyheneicosadiene (III). In female tip extract they were found in a ratio of 1625, respectively, and in trapped female effluvia the ratio was 1627, respectively. Combinations of III with either I or II elicited sustained upwind flight in a wind tunnel, but none of these compounds by themselves did so. There is evidence that the antennal acceptor site for III is chiral.Lepidoptera: Arctiidae.Supported in part by the Rockefeller Foundation and by National Science Foundation Grants GB-38020 and PCM 78-13241.     

Characteristics and compositions ofCarissa spinarum,Leucaena leucocephala andPhysalis minima seeds and oils

The seeds and extracted oils ofCarissa spinarum (Apocynaceae), (I),Leucaena leucocephala (Leguminosae) (II) andPhysalis minima (Solanaceae) (III) were analyzed for characteristics and compositions. The seeds of I, II and III contained 22.4, 6.4 and 40.0% oil and 10.1, 27.6 and 17.9% protein, respectively. The oils of I, II and III had, respectively, iodine values 70.1, 113.5 and 122.5; saponification values 186, 188 and 189; unsaponifiable matter 5.2, 2.5 and 0.8%, and the following fatty acid compositions (area %): palmitic 12.6, 14.2, 10.5; stearic 7.6, 6.1, 8.6; oleic 72.7, 20.1, 17.3; linoleic 5.2, 53.8, 61.4; linolenic 0.9, 1.8, 0.0, and arachidic 1.0, 2.3, 0.0. II contained 1.7% lignoceric acid. III contained small amounts of hexadecenoic (0.1%), epoxy (0.6%) and hydroxy (1.5%) fatty acids.     

Experimental and Computational Studies on the Thermal Degradation of Nitroazidobenzenes

In this combined experimental and theoretical study the thermal degradation of 2‐nitroazidobenzene ( I ), 2,4‐dinitroazidobenzene ( II ) and 2,4,6‐trinitroazidobenzene ( III ) to yield benzofuroxan ( IV ), 4‐nitrobenzofuroxan ( V ), and 4,6‐dinitrobenzofuroxan ( VI ) were investigated by thermoanalytical (TG, DSC) and computational methods. In contrast, furoxan formation was not observed for 4‐nitroazidobenzene ( VII ) under heating due to the para position of the nitro group in the benzene ring. All compounds were characterized by elemental analysis, vibrational (IR) spectroscopy and mass spectrometry. The crystal structure of compound III was determined by single‐crystal X‐ray diffraction. DFT‐based structure optimizations and frequency analyses were performed at the B3LYP/cc‐pVDZ level of theory. The structural parameters of the fully optimized compound III showed very good agreement with the single‐crystal X‐ray data. The enthalpies of formation for compounds I , II , III , IV , V , and VI were calculated using the complete basis set (CBS‐4M) method of Petersson and co‐workers in order to obtain accurate energies. The enthalpies of degradation for compounds I , II , and III were obtained from calculated enthalpies of formation according to the Hess Law and were compared with the experimental values, which were available from DSC analysis and were found to be in very good agreement.     

Intraspecific variation and interspecific differences in sex pheromones of sibling species inCtenopseustis obliquana complex

The specific status ofCtenopseustis obliquana pheromone-types I, II, and III has been more fully examined. Females of types I and III produce a mixture of (Z)-8- and (Z)-5-tetradecenyl acetates (Z8-14:Ac, Z5-14: Ac). The previously reported different ratios of these two components in females of the two types (type I=8020, III=9010) have been reinvestigated. The median ratios of each type differed significantly, although there was some overlap in the ranges of these ratios. A field cage trial showed that males of type III are attracted to females of type I, so the observed differences may be ascribed to intraspecific variation. In contrast to females of types I or III, females of type II produce Z5-14Ac but no Z8-14Ac. The electroantennogram (EAG) profile of antennae of type II males shows a maximum response to Z5-14Ac, while the EAG profiles of types I and III show a strong response to Z8-14Ac. In wind tunnel tests using mixtures of these two compounds, type II males prefer blends consisting of all or mostly Z5-14: Ac, while type I males showed a preference to a mix of 70% Z8-14Ac plus 30% Z5-14Ac. We found that type I males are attracted to type I females when offered a choice between type I and type II females in a field cage test and that type II males similarly prefer type II females. Males of types I and II have specialist cells for Z8-14Ac and Z5-14Ac but differ with respect to relative densities of these cells and to further cell types responsive to other alkenyl acetates. Type IIC. obliquana is considered therefore a sibling species of types I and III. In addition, the amount of Z5-14Ac produced by type II females varied geographically. Females from the North Island produced significantly less (median=1.2 ng) Z5-14Ac than females from the South Island (median=2.2 ng). Type II populations in the North Island morphologically resembled sympatric type I, rather than type II from the South Island and are designated as type II (North Island). Type II (North Island) populations have so far been found only at Rukuhia (near Hamilton) and from Kerikeri. In contrast, type II populations are sympatric with type III populations over much of the South Island. In a field cage trial, males of types II and II (North Island) were attracted to females of both II and II (North Island). We tentatively ascribe the differences between type II and type II (North Island) to intraspecific variation.     

Synthetic detergents from animal fats. VII. Detergent combinations

Summary Laboratory measurements of detergency were made on mixtures of sodium salts of sulfated hydrogenated tallow alcohol (X), disodium salts of α-sulfonated hydrogenated tallow acids (Y), sodium dodecylbenzenesulfonate (Z), and a builder (B) using three different kinds of standard soiled cotton. Component X was the most important, and mixtures not containing X were generally inferior detergents. Built XY mixtures were better than XZ mixtures with one kind of soiled cotton (cloth I). Built XZ mixtures were better than XY mixtures with another soiled cotton (cloth III). The results, based on laboratory measurements of detergency using standard soiled cotton, are suggestive rather than conclusive. Partial substitution of X by Y or Z, or by both Y and Z, may be possible without loss in detergency. Presented at the meeting of the American Oil Chemists’ Society, Houston, Tex., April 1956. A laboratory of the Eastern Utilization Research Branch, Agricultural Research Service, U. S. Department of Agriculture.     

Synergistic effect in gamma-irradiated poly(vinyl chloride) hard foils stabilized by plasticizer–stabilizer systems

Changes in transparency and color as well as G_HCl values of hard PVC foils exposed to gamma radiation were investigated while using different amounts of the stabilizers ethylene glycol bis-β-aminocrotonate (I), calcium/zinc laurate + epoxy compounds (II), and magnesium/zinc stearate + sorbitol + epoxy compounds (III), and plasticizers dioctyl phthalate (DOP) (IV), dioctyl sebacate (V), propylene glycol polyadipate + octyl alcohol composition (VI), and diisotridecyl phthalate (VII). A strong synergistic effect was observed in systems containing both plasticizer and stabilizer. Best results were obtained for the I + II + IV, I + II + V, and I + III + V systems.     

Novel sex pheromone components from the fall cankerworm moth,Alsophila pometaria

A sex pheromone extract from fall cankerworm moths,Alsophila pometaria, attracted conspecific males in field tests. Four EAG-active components were isolated from the extract and identified by GC-MS, highfield PMR spectroscopy, and microchemical techniques asn-nonadecane (I), (Z,Z,Z)-3,6,9-nonadecatriene (II), (Z,Z,Z,E)-3,6,9,11-nonadecatetraene (III), and (Z,Z,Z,Z)-3,6,9,11-nonadecatetrane (IV). Studies of the behavioral responses of male moths in a flight tunnel to the isolated components showed II, III, and IV were the major components of the sex pheromone. No sex pheromone behavioral responses were observed for I.Lepidoptera: Geometridae.issued as NRCC No. 22964.     

Sex pheromone of the fall webworm moth,Hyphantria cunea

Three compounds have been identified as sex pheromone components produced by female fall webworm moths,Hyphantria cunea (Drury). These compounds are: (Z,Z)-9,12-octadecadienal (I), (Z,Z,Z)-9,12,15-octadecatrienal (II), and (Z,Z)-3,6-cis-9,10-epoxyheneicosadiene (III). The ratio of these compounds was approximately 5613, respectively, in female tip extracts prepared from U.S.S.R, insects and approximately 1821, respectively, in extracts from U.S. insects. The ratio in female effluvia trapped from U.S. insects was 1627, respectively. Compound III plus either I or II is effective in eliciting upwind flight in a wind tunnel. Compounds I, II, and III are also components of the sex pheromone system of the saltmarsh caterpillar moth,Estigmene acrea (Drury).Lepidoptera: Arctiidae.Part of this work was carried out under the sponsorship of the U.S.A.-U.S.S.R. Scientific Exchange Program and the U.S.S.R. Ministry of Agriculture. It was also supported in part by National Science Foundation grant PCM78-13241. These results were first disclosed at the EUCHEM Conference on Chemistry of Insects, held at Borgholm, Sweden, on August 13–17, 1979. We sadly note the passing away of our distinguished colleague and friend, Dr. A.S. Hill.     

Judd's 1951 color-mixture diagram

Vos demonstrated that the Judd 1951 color-mixture diagram is a projective transformation of the CIE 1931 mixture diagram. He has provided transformation formulas for computing values of x′ and y′ from x and y, but he does not explain how the one set of data is derived from the other. Neither does Judd. Judd wanted the CIE to replace the 1931 V(Λ) curve with a new V(Λ) curve and to replace the 1931 XYZ diagram with a new X′Y′Z′ diagram. I have assumed that Judd started with the CIE 1931 RGB diagram. His X′Y′Z′ diagram can be derived from the RGB diagram if we use a different set of luminosity coefficients than those specified by the CIE. This change in luminosity coefficients was no doubt intended to compensate for the use of a new V(Λ) curve, but Judd has ignored the effect that this change in the luminosity coefficients should have on the alychne of the RGB diagram and the locus of spectral colors. This makes Judd's X′Y′Z′ diagram inappropriate for use in colorimetry and for use in building color-vision models. I have proposed a new solution to this problem.     

Aggregation pheromones of the flat grain beetle,Cryptolestes pusillus (Coleoptera: Cucujidae)

Aggregation pheromones were isolated fromCryptolestes pusillus (Schönherr), a coleopteran pest of stored products. Porapak Q-captured beetle and frass volatiles were fractionated by preparative gas-liquid chromatography. The fractions were bioassayed with an arena olfactometer and/or with a two-choice, pitfall olfactometer. Three biologically active, male-produced compounds eliciting aggregation behavior from adultC. pusillus were isolated and identified by spectroscopic methods as (Z)-3-dodecenolide (I), (Z)-5-tetradecen-13-olide (II), and (Z,Z)-3,6-dodecadienolide (III). Compound I was the major volatile produced and was active alone. Compound II was not active alone, but synergized the response to I. Compound III was active alone at higher concentrations, but did not significantly increase the response when added to the most active mixture of I and II, and so it is probably not part of the aggregation pheromone. Pheromone production increased dramatically when the insects were aerated on a food source.Research supported in part by the Natural Sciences and Engineering Research Council of Canada, Operating Grants A3881 and A3785, Strategic Grant 60958, and a Graduate Scholarship to J. G. Millar.     

Anti-adhesive effects of Budesonide combined with spraygel in a cecal abrasion model: an experimental study

Many methods have been described for preventing or reducing postoperative adhesions. In this work, we evaluated the effectiveness of Budesonide in combination with SprayGel in a reducing postoperative adhesion in rats as the model. Cecal abrasion was achieved in 60 male Sprague-Dawley rats, by brushing and by applying 70% alcohol. The rats were separated into six groups and treated with six solutions (Group I – saline; II – Budesonide 50?μg; III – Budesonide 250?μg; IV – SprayGel; V and VI – SprayGel?+?Budesonide 50 and 250?μg). Serum Budesonide, glucose, alanine aminotransferase, aspartate aminotransferase, alkaline phosphatase and blood urea nitrogen levels were measured at postoperative day (POD) 2 and 14. The rats were killed on POD 14, and intra-abdominal adhesion formation was scored. Histopathological samples were obtained from the cecum and terminal ileum to evaluate microscopic adhesion formation. Our results showed that Group VI had both the minimum macroscopic adhesion score and the minimum microscopic score. All other groups had significantly lower microscopic adhesion scores than Group I. However, there was no statistical significance among any other groups. Serum AST levels of Group III were significantly higher than in Groups I, II, IV, and V (p?<?0.046). Serum AST levels of Group III on POD 14 were also significantly higher than that of all other groups (p?<?0.02). On POD 14, there was no Budesonide in the sera of Groups II and V. However, Groups III and VI had trace amounts of Budesonide (0.009 and 0.007?μg, respectively). In conclusion, we have showed that the effect of Budesonide is dosedependent. Both anti-adhesive and hepatotoxic side effects of Budesonide increased as the dose increased. Combining Budesonide with SprayGel synergistically increased the anti-adhesive benefits and prevented hepatotoxicity from the slower release of Budesonide.     

Structural characterisation of some polystyrene—polyisoprene copolymers

The various levels of organisation which may be distinguished in non-crystalline block copolymers are considered. An account is given of the application of low-angle X-ray diffraction and electron microscopy to the characterisation of the two-phase morphology and grain texture of some styrene/isoprene copolymers. The first group of copolymers to be considered contains two series of samples of the type S–I, (S–I–)₂X, (S–I–)₃Y, and (S–I–)₄Z where I is polyisoprene, S polystyrene and X, Y and Z are di-, tri- and tetra-functional coupling groups. The second group of copolymers which was subjected to a less detailed study than the first consists of just two polystyrene-g-polyisoprene samples.     

Female sex pheromone of the melonworm,Diaphania hyalinata (Lepidoptera: Pyralidae), and analysis of male responses to pheromone in a flight tunnel

Ten C₁₆ chain-length compounds were identified from heptane extracts of ovipositors of female melonworm,Diaphania hyalinata (L.). The major constituents of the extracts were (E)-11-hexadecenal and (E,E)-10,12-hexadecadienal [(E,E)-10,12–16:Ald] and the alcohols and acetates of these olefins were found in trace amounts (<2%). Extracts also contained traces of (E,Z)- and (Z,Z)-10,12-16:Ald, hexadecanal, and 1-hexadecanol. Analysis of the behavioral responses of males to synthetic mixtures of these compounds and responses to ovipositor extracts in a flight tunnel showed that a synthetic mixture of the 10 compounds elicited a behavioral repertoire from males that was indistinguishable from that elicited by ovipositor extract. Flight tunnel studies also indicated that six of the 10 compounds probably represent the essential components of the female's sex pheromone.Supported in part by USDA Cooperative Agreement No. 58-32U4-1-299. Scientific Article No. A-4073, Contribution No. 7058 of the Maryland Agricultural Experiment Station. Mention of a commercial product in this paper does not constitute a recommendation by the U.S. Department of Agriculture.     

Ecological adaptation of an Aristolochiaceae-feeding swallowtail butterfly,Atrophaneura alcinous,to aristolochic acids

Seven analogs of aristolochic acids (I, II, III, B, C, D, and E) were isolated from the leaves ofAristolochia debilis and characterized as the larval feeding stimulants of an Aristolochiaceae-feeding swallowtail butterfly,Atrophaneura alcinous. Aristolochic acids showed synergistic activity in combination with the water-soluble components in the leaf extract. Aristolochic acids were detected in the body tissues and specialized organs throughout all life stages ofA. alcinous. Larval osmeterial fluid contained aristolochic acids as high as 2% of the secretions, the compositions of which were similar to that found in the leaf extracts. In contrast, the eggs selectively contained aristolochic acids I and II. These two acids were present both in the egg yolk and egg coating material as well as in the collateral glands (glandulae sebaceae) of the adult females. The cannibalistic activity of the larvae against the eggs and pupae seemed to be triggered by aristolochic acids present on the egg surface and pupal cuticle, suggesting a possible adaptive mechanism in this species. Aristolocic acid I deterred feeding of tree sparrows, which suggested a defensive role against vertebrate predators.     

Synthesis and Characterization of a New Polymer-Based Supramolecular Recognition Material and its Adsorption for Cesium

A novel macroporous polymer-based 25,27-bis(iso-propyloxy)calix[4]arene-26,28-crown-6 (BiPCalix[4]C6) supramolecular recognition material, BiPCalix[4]C6/XAD-7, was synthesized. It was performed by vacuum impregnation and immobilization of BiPCalix[4]C6 into the pores of the macroporous XAD-7 particles. The composition and structure were characterized using SEM, BET, TG-DSC, FT-IR, and XRD, respectively. The adsorption of some typical metals contained in highly active liquid waste (HLW) such as Ru(III), Mo(VI), K(I), Rb(I), Cs(I), Sr(II), Ba(II), La(III), and Y(III) onto the BiPCalix[4]C6/XAD-7 materials was investigated. The effects of the HNO₃ concentration and contact time on the adsorption of the tested metals were evaluated. It was found that at the optimum concentration of 4.0 M HNO₃, BiPCalix[4]C6/XAD-7 exhibited excellent adsorption ability and high selectivity for Cs(I) over all the other tested metals, which showed weak or almost no adsorption except Rb(I). It demonstrated that application of the polymer-based supramolecular recognition material, BiPCalix[4]C6/XAD-7, in partitioning of Cs(I) from HLW is promising.     

Components of male aggregation pheromone of strawberry blossom weevil, Anthonomus rubi herbst. (Coleoptera:Curculionidae)

The strawberry blossom weevil, Anthonomus rubi, is a major pest of strawberries in the United Kingdom and continental Europe. As part of a project to develop noninsecticidal control methods, the pheromone system of this species was investigated. Comparison of volatiles produced by field-collected, overwintering individuals of each sex led to identification of three male-specific compounds—(Z)-2-(3,3-dimethylcyclohexylidene)ethanol, (cis)-1-methyl-2-(1-methylethenyl)cyclobutaneethanol, and 2-(1-methylethenyl)5-methyl-4-hexen-1-ol (lavandulol)—in amounts of 6.1, 1.2, and 0.82 g/day/male. The first two compounds are components of the aggregation pheromone of the boll weevil, Anthonomus grandis, grandlure II and grandlure I, respectively. Grandlure I was the (1R,2S)-(+) enantiomer and lavandulol was a single enantiomer, although the absolute configuration was not determined. Trace amounts of the other two grandlure components (Z)-(3,3-dimethylcyclohexylidene)acetaldehyde (grandlure III) and (E)-(3,3-dimethylcyclohexylidene)acetaldehyde (grandlure IV) were also detected. (E,E)-1-(1-Methylethyl)-4-methylene8-methyl-2,7-cyclo-decadiene (germacrene-D), a known volatile from strawberry plants, Fragaria ananassa, was collected in increased amounts in the presence of pheromone-producing weevils. Male weevils only produced pheromone on F. ananassaand not on scented mayweed, Matracaria recutita, or cowparsley, Anthriscus sylvestris, although these are known food sources. In field trials using various combinations of synthetic grandlures I, II, III, and IV and lavandulol, significantly more weevils were caught in traps baited with blends containing grandlure I and II and lavandulol than in those baited with blends without lavandulol or unbaited controls. Addition of grandlure III and IV had no significant effect on attractiveness. Horizontal sticky traps were found to be more effective than vertical sticky traps or standard boll weevil traps. In mid-season females predominated in the catches, but later more males than females were trapped.     

Radiation yield of hydrogen chloride in the poly(vinyl chloride) foils irradiated by accelerated electrons

The G_HCl values of PVC foils, containing 18% of dioctylphthalate, irradiated with accelerated electrons were studied after addition of various amounts of the stabilizers: (I) ethylene glycol bis-β-aminocrotonate, (II) calcium/zinc laurate + epoxy compounds, (III) calcium/zinc stearate, (IV) dioctyltin bis(octylthioglycolate). The effect of stabilization turned out to be very good, especially when stabilizer I was used. In the case of soft PVC foils in contact with water, elution of hydrogen chloride occurs. This creates difficulties in preparing PVC foils sterilized radiatively for medical purposes, especially if the foils are expected to be in contact with water.     

Components of the sex pheromone of the female spotted stalk borer,Chilo partellus (Swinhoe) (Lepidoptera: Pyralidae): Identification and preliminary field trials

FemaleChilo partellus (Swinhoe) abdominal tip extracts were examined by gas-liquid chromatography (GLC) combined with simultaneous electroantennographic (EAG) recording from the male moth. Two olfactory stimulants were detected and identified as (Z)-11-hexadecenal (I) and (Z)-11-hexadecen-1-ol (II) by their GLC behavior, microchemical reactions, and comparison with synthetic materials. Both compounds were detected in volatiles emitted by the calling female moth. Synthetic (Z)-9-tetradecenyl formate, a structural analog of aldehyde (I), also elicited a significant EAG response from the male moth. Field trials carried out in India using synthetic (I) and (II) as bait in water traps showed that compound (I) was highly attractive to maleC. partellus; compound (II) was not attractive, and its addition to (I) significantly reduced trap catches.     

Morphology and mechanical properties of urethane acrylate resin networks

A series of urethane acrylate resins (UARs) having various amounts of hard segment were synthesized from poly(oxypropylene) diols (PPOs) with different molecular weights and characterized. The relationship between the morphologies and mechanical properties of these UAR (UARX‐Y‐Z, in which X means the molecular weight of PPO, Y means the content of hard segment, and Z means the content of comonomer) networks was investigated in detail. It was found that the morphology of the UARX‐Y‐Z network was related to the contents of hard segment and the comonomer (methyl methyacrylate—MMA) as well as the molecular weight of PPOs. The UAR1000‐0‐34 network synthesized from PPO210(M_n = 1000) is a homogeneous system due to the good compatibility between the PPO210 and the MMA segment. TheUAR1000‐0‐60 network exhibits the morphology of partial microphase separation resulting from increasing the length of the MMA segment, so as to decrease the miscibility between the soft and hard segment. For the UAR1000‐30‐34 network having a higher content of the hard segment, the hard segments tend to form domains with the limited short‐range and long‐range order, leading to the formation of the microcrystallites, and therefore it shows higher tensile strength and elastic modulus. For UAR400‐0‐34 network with lower molecular weight PPO204 (M_n=400), a high glass transition temperature and some microcrystallites were observed. Such a network exhibits the best mechanical properties over all UAR networks studied. © 2000 John Wiley & Sons, Inc. J Appl Polym Sci 77: 1532–1537, 2000