Responses of male codling moths (Laspeyresia pomonella) to codlemone and other alcohols in a wind tunnel

The primary pheromone (E,E)-8,10-dodecadien-1-ol (I, codle-mone), 11 further alcohols, and binary blends of both were evaluated for attractiveness as defined by the percentage ofL. pomonella males showing oriented upwind flight terminated by landing at the source within 10 min after release. Sources of I were attractive from 10^–5 g to 10¹ g, with approx. 70% males responding at 10^–3–10^–1 g. Most other alcohols also showed attractiveness, but the dose-response curves differed greatly with respect to the range of effective lure doses as well as the maximum response level reached at any dose. (E,E)-7,9-Undecadien-1-ol (III) revealed a dose-response curve similar in shape to I but shifted towards higher concentrations. (E,E)-8,10-Tridecadien-1-ol (II) and (E)-8,10-undecadien-1-ol (IV) exhibited threshold values of 10^–5 g (same as for I) and were effective over, respectively, seven and nine decades of source load, but they did not reach a response level of 40% at any test amount. (E)-9,11-Dodecadien-1-ol (VI) and the monoenes (E)-8-, (E)-10-, and (Z)-10-dodecen-1-ol (VIII-X) showed weak attractivity restricted to one to three test doses. Upwind approaches that broke off a few centimeters from the source were rarely seen in tests with I but frequently occurred with some of the analogs. When combined with 10^–3 g of I, all alcohol analogs showed inhibitory properties, although the amounts required to obtain a significant lowering of response differed by up to 10⁵-fold. This amount was the lowest (10^–4 g) for the positional isomer VI, and the highest (10¹ g) for undecan-1-ol (XI) and dodecan-1-ol (XII). With some mixtures, the presence of the inhibitor appeared to cause an alteration in landing behavior. No synergistic effects were seen in these tests. The results are briefly considered with respect to the sensory perception of the test stimuli and the involvement of minor components in the female pheromone blend.     

Effects of three phenolic compounds onLemna gibba G3

Lemna gibba L. G3, (duckweed) was used as a bioassay organism to test the allelochemical effects of salicylic acid (SA), ferulic acid (FA), and umbelliferone (UM). Growth rate (K), dry weight (DW) and total chlorophyll (CHL) production were measured after seven days of growth. The bioassay procedure used 50 ml of E medium with and without sucrose in 125-ml Erlenmeyer flasks plus the selected concentration of allelochemical. At concentrations of 50 M and greater, SA caused inhibition of K and DW production inL. gibba G3, while the threshold for CHL reduction was 20 M. FA inhibited the DW and CHL production at 100 M when the compound was auto-claved in E medium containing sucrose. Treatments of UM were least toxic with an inhibition threshold of 500 M for K and DW production in medium without sucrose. UM did not reduce CHL production until 750 M. In some cases, different thresholds of inhibition were observed depending on the presence or absence of sucrose and tartaric acid in the medium, and whether or not the chemicals were autoclaved with the medium.This research was presented by the senior author as partial fulfillment for the Master of Arts degree, Biology Department, Hood College, Frederick, Maryland. Mention of a trade name or proprietary product does not constitute a guarantee or warranty by the USDA and does not imply its approval to the exclusion of other products that may be suitable.     

Synergism of Polygodial and trans-Cinnamic Acid on Inhibition of Root Elongation in Lettuce Seedling Growth Bioassays

A bicyclic sesquiterpene dialdehyde, polygodial did not inhibit root elongation up to a concentration of 12.5 g/ml in a lettuce seedling assay: trans-Cinnamic acid inhibited the elongation by 50% at 1.2 g/ml (8.1 M). The inhibitory activity of trans-cinnamic acid was enhanced 17-fold when used in combination with 6.25 g/ml (26.5 M) of polygodial. A decrease in the pH of the medium was observed during normal seedling growth, indicating transport of protons from the cells by a plasma membrane H⁺-ATPase. The inhibitory effect of trans-cinnamic acid on the elongation was reduced to some extent in 2 mM phosphate buffer (pH 7.0) during seedling growth. Although polygodial did not inhibit the activity of H⁺-ATPase in the plasma membrane fraction of roots in normally growing seedlings, a decrease in activity was found in the fraction obtained from seedlings incubated with 20 g/ml of polygodial. These results suggest that polygodial functions synergistically with trans-cinnamic acid in the inhibition of root elongation via restriction of proton transport from the cytoplasm of germinated cells.     

Effect of diacetyl piquerol on H+-ATPase activity of microsomes fromIpomoea purpurea

The effect of an allelopathic compound, diacetyl-piquerol on the H⁺ -ATPase activity of the microsomal fraction from the radicles of a common weedIpomoea purpurea was studied. The diacetyl-piquerol inhibited the germination and radicle growth fromI. purpurea; the radicle growth was increasingly inhibited (10% to 100%) as piquerol concentrations were raised (10 M to 1000 M). The H⁺-ATPase activity was inhibited (48%) by 500 M diacetyl-piquerol, and this inhibition was higher in plasma membrane ATPase (67.2%) than in tonoplast membrane ATPase (31.4%). Additional studies of the precise physiological mechanisms of interference caused by allelopathic compounds are needed.This study was sponsored by Project PCECCCNA-050954 of Consejo Nacional de Ciencia y Tecnología (CONACyT).     

Fate of quinolizidine alkaloids through three trophic levels:Laburnum anagyroides (Leguminosae) and associated organisms

The quinolizidine alkaloids (QA) of golden rain,Laburnum anagyroides, and those of phytophagous insects associated with the plant, as well as of parasitoids of the latter, were analyzed by capillary GLC and GLC-MS. The alkaloid content in samples of vegetative plant parts was high at the beginning of the season, then decreased, while that of reproductive organs was high throughout flowering, pod formation, and maturation. The analyses showed that the QA of the plant passed through two higher trophic levels (herbivorous insects and their parasitoids) and that the alkaloid pattern changed little during the passage. The alkaloids were present in two phytophagous insect species associated with golden rain: the predispersal seed predator,Bruchidius villosus [5–13g/g fresh weight (fw)], andAphis cytisorum (182–1012g/g fw), an aphid that feeds on shoots, leaves, and inflorescences. Braconid and chalcidoid parasitoids emerging from the bruchid host also contained alkaloids (1.3–3g/g fw), as did three foraging ant species,Lasius niger, Formica rufibarbis, andF. cunicularia (45g/g fw), that visited the aphid colonies or honeydew-covered leaves of aphid-infested plants. The hypothesis that developing bruchid larvae and/or the plant manipulate QA supply to infested seeds was not supported, because QA content of leftover endosperm in seeds after bruchid development was similar to that of uninfested seeds. The frass of developing bruchid larvae was rich in QA (31g/ g dry weight). While aphids sequestered, the bruchid larvae took up and eliminated QA with the frass without chemical transformation.     

Interactions between pheromone traps with different strength lures for the pine beauty moth,Panolis flammea (Lepidoptera: Noctuidae)

Catches of malePanolis flammea in traps baited with lures containing 25 g of sex attractant are enhanced when in the proximity of traps baited with 125-g lures. The degree of enhancement is increased as the intertrap distance is decreased, and when the low-dose trap is upwind of the high-dose one. The patterns of alteration in trap catch suggest that moths initially attracted by one lure may divert into other traps, which may be either upwind of the original trap (overshooting), or downwind (undershooting). Overshooting can result in up to fivefold increases in catch and may provide a useful method for estimating the attractant zone of particular lure/trap combinations.     

Leaf surface chemicals fromNicotiana affecting germination ofPeronospora tabacina (adam) sporangia

A bioassay was used to evaluate the effects of cuticular leaf components, isolated fromN. tabacum, N. glutinosa (accessions 24 and 24a), and 23other Nicotiana species, on germinationof P. tabacina (blue mold). The leaf surface compounds included- and-4,8,13,-duvatriene-l,3-diols (DVT-diols), (13-E)-labda-13-ene-8-,15-diol (labdenediol), (12-Z)-labda-12,14-diene-8-ol (cis-abienol), (13-R)-labda-8,14-diene-13-ol (manool), 2-hydroxymanool, a mixture of (13-R)-labda-14-ene-8,13-diol (sclareol), and (13-S)-labda-14-ene-8,13-diol (episclareol), and various glucose and/or sucrose ester isolates. The above in acetone were applied onto leaf disks of the blue moldsusceptibleN. tabacum cv. TI 1406, which was then inoculated with blue mold sporangia. Estimated IC₅₀ values (inhibitory concentration) were 3.0g/cm² for-DVT-diol, 2.9/cm² for-DVT-diol, 0.4g/cm² for labdenediol and 4.7g/cm² for the sclareol mixture. Manool, 2-hydroxymanool, andcis-abienol at application rates up to 30g/cm² had little or no effect on sporangium germination. Glucose and/or sucrose ester isolates from the cuticular leaf extracts of 23Nicotiana species and three different fractions fromN. bigelovii were also evaluated for antimicrobial activity at a concentration of 30g/cm². Germination was inhibited by >20% when exposed to sugar esters isolated fromN. acuminata, N. benthamiana, N. attenuata, N. clevelandii, andN. miersii, and accessions 10 and 12 ofN. bigelovii. These results imply that a number of compounds may influence resistance to blue mold in tobacco.     

Effect of fungal metabolite peramine and analogs on feeding and development of argentine stem weevil (Listronotus bonariensis)

Peramine, a pyrrolopyrazine alkaloid produced by the fungal endophyte of perennial ryegrassAcremonium lolii, deterred the feeding of both adults and larvae of the graminacious herbivore, the Argentine stem weevil (Listronotus bonariensis), at 0.1 g/g and 10 g/g, respectively. In a no-choice test fewer stem weevil larvae fed and developed on diet containing as little as 2 g/g peramine. The proportion of larvae which did not develop beyond the first instar was higher on diet containing peramine and appeared to be due to a higher proportion of larvae which did not feed. For larvae which fed on the peramine-containing diet, feeding scores and times to pupation were not significantly different from those of controls. A number of simple peramine analogues showed feeding-deterrent activity against adult weevils, indicating the importance of the pyrrolopyrazine ring system of peramine in determining feeding-deterrent activity.     

Effect of Volatile Constituents from <Emphasis Type="Italic">Securidaca</Emphasis><Emphasis Type="Italic">Longepedunculata</Emphasis> on Insect pests Of Stored Grain

Securidaca longepedunculata Fers (Polygalaceae) is commonly used as a traditional medicine in many parts of Africa as well as against a number of invertebrate pests, including insects infesting stored grain. The present study showed that S. longepedunculata root powder, its methanol extract, and the main volatile component, methyl salicylate, exhibit repellent and toxic properties to Sitophilus zeamais adults. Adult S. zeamais that were given a choice between untreated maize and maize treated with root powder, extract, or synthetic methyl salicylate in a four-way choice olfactometer significantly preferred the control maize. Methyl salicylate vapor also had a dose-dependant fumigant effect against S. zeamais, Rhyzopertha dominica, and Prostephanus truncates, with a LD₁₀₀ achieved with a 60 l dose in a 1-l container against all three insect species after 24 hr of exposure. Probit analyses estimated LD₅₀ values between 34 and 36 l (95% CI) for all insect species. Furthermore, prolonged exposure for 6 days showed that lower amounts (30 l) of methyl salicylate vapor were able to induce 100% adult mortality of the three insect species. The implications are discussed in the context of improving stored product pest control by small-scale subsistence farmers in Africa.     

Defensive secretions of three species ofAcilius (Coleoptera: Dytiscidae) and their seasonal variations as determined by high-pressure liquid chromatography

A rapid, sensitive, stable, and quantitative high-pressure liquid chromatographic technique was developed for the analysis of defensive secretions obtained from the pygidial and prothoracic glands of dytiscids. Methods were developed for both normal phase (Porasil) and reverse phase (Bondapak C₁₈) columns. The applicability of this technique was demonstrated when defensive compounds ofAcilius semiculcatus, A. sylvanus andA. mediatus were isolated, identified, and quantitated. No major differences were found in the composition of the defensive secretions between the three species. The seasonal defensive titer ofA. semisulcatus was determined from June through October 1977. The pygidial defensive agents (benzoic acid,p-hydroxybenzaldehyde, and methylp-hydroxybenzoate varied from 9.0 to 67.8 g and exhibited a maximum in July, and a steroid from the prothoracic gland varied from 7.1 to 33.2 g and was maximum in October.     

Lesser peachtree borer: Influence of pheromone concentration,isomeric blend,and experimental design on trap capture

Trap capture data from Ohio and Wisconsin show that (E,Z)-3-13-octadecadien-1-ol acetate alone is an effective trap bait for maleSynanthedon pictipes (Grote and Robinson). Attractiveness increased by increasing attractant concentration but not by adding theZ,E geometrical isomer.S. pictipes males partitioned themselves in a linear fashion among traps baited with 10–100 g of attractant in 10-g increments. Furthermore, they discriminated between 50- and 100-g baits placed in the same tree. These and other results indicate that, in clearwing experiments involving noninhibitory compounds and blend tuning, high trap density can be used successfully.Lepidoptera: Sesiidae.Approved for publication as Journal Article No. 45–79 of the Ohio Agricultural Research and Development Center, Wooster, Ohio 44691.Investigations supported in part by USDA, Cooperative State Research Service, Contract No. 316-15-59.     

Influence of tobacco leaf surface chemicals on germination ofPeronospora tabacina adam sporangia

Chromatographic procedures were utilized to isolate and purify components of tobacco cuticular extracts and leaf surface chemicals.In vitro microbial bioassays determined the influence of these leaf surface compounds on germination and germ tube morphology ofP. tabacina sporangia, the tobacco blue mold pathogen, and to a lesser extentAlternaria alternata, the tobacco brown spot pathogen. Exposure to 10 g/cm² of - and -duvatrienemonols, sucrose esters, or hydrocarbons did not inhibit germination, whereas germination was significantly decreased bycis-abienol.cis-Abienol did not inhibit sporangial germination when combined with sucrose esters or hydrocarbons at a combined 10 g/cm². Germination of sporangia was completely inhibited by - and -duvatrienediols. In contrast to a previous report, -DVT-diol was more inhibitory than the isomer. Toxic effects of the DVT-diols were not altered by pH. Diluting the DVT-diols to less than 0.1 g/cm² resulted in a small but significant stimulation of germination. Previously, the DVT-diols had been identified only as inhibitory toP. tabacina. None of the leaf surface chemicals affected germination ofA. alternata conidia.Present Address: Department of Forestry, Biltmore Hall, North Carolina State University, P.O. Box 8002, Raleigh, North Carolina 27695-8002.     

Isolation,characterization and activity of phytotoxic compounds from quackgrass [Agropyron repens (L.)Beauv.]

Previous experiments showed that legumes grown in the presence of living or herbicidally treated quackgrass residues or extracts exhibited reduced seedling root and shoot growth and decreased nodulation and nitrogen fixation. Aqueous extracts of quackgrass shoots were most inhibitory to plant growth. Upon sequential partitioning of an aqueous extract of quackgrass shoots, the ether extract possessed the most activity and caused 50% reductions in radicle elongation of eight crop and weed species at concentrations of less than 240 g/ml (small-seeded species) and 1000 g/ml (large-seeded species). Snapbeans (Phaseolus vulgaris L. Bush Blue Lake) grown aseptically in agar containing an ether extract at 100 and 200 g/ml exhibited severe root browning, lack of root hair formation, and a two- to three-fold reduction in root and shoot dry weights. The ether extract of quackgrass shoots had no inhibitory effect on the growth of fourRhizobium species in Petri dishes or two species in broth culture. Inhibitors present in the ether extract may influence the legumeRhizobium symbiosis indirectly by reducing legume root growth and root hair formation. The ether extract of quackgrass shoots was separated using high-pressure liquid, thin-layer, and liquid column chromatography in an attempt to isolate and identify the inhibitors responsible for the inhibition of seedling growth. Two closely related flavonoid inhibitors were isolated from the ether extract. One was identified as 5,7,4-trihydroxy-3,5-dimethoxyflavone (tricin). Both flavonoids caused 50% inhibition of radicle elongation in cress (Lepidium sativum L. Burpee curly) seeds at concentrations of less than 125 g/ml. Both flavonoids were found in ether extracts of quackgrass shoots and rhizomes, but the largest amounts of both compounds occurred in quackgrass shoots collected from the field.Journal article No. 11887 of the Michigan Agricultural Experiment Station.     

Dihydromatricariate-based triglycerides,glyceride ethers,and waxes in the australian soldier beetle,Chauliognathus lugubris (Coleoptera: Cantharidae)

The soldier beetleChauliognathus lugubris is shown to contain triglycerides and glyceride ethers of 8-dihydromatricaria acid, and waxes of the C₁₂ homolog, of this acid, as well as the previously reported free acid. The triglycerides contain one, two, or three dihydromatricariate moieties, with any remaining positions esterified with normal fatty acids. The glyceride ethers were monostearyl ethers of glycerol esterified with dihydromatricaria acid and oleic or linoleic acid. The waxes, which also include a dihydromatricaria chromophore in the alcohol moiety, occur only in the females and are present in paired accessory glands in the abdomen. The ethers are restricted to females and appear to be associated with developing eggs. The triglycerides are much more abundant in females than males. Triglycerides, glyceride ethers, and waxes represent about 95% of the dihydromatricariate moiety (average, ca. 590 g) in females with free acid the remainder; in males free acid is present to over 50% (ca. 22 g) and the remainder is triglyceride (ca. 15 g). Larvae contain mainly tridihydromatricariate-substituted triglyceride and a smaller quantity of the free acid.     

Aphid deterrence by glucose esters in glandular trichome exudate of the wild tomato,Lycopersicon pennellii

Settling of the potato aphid,Macrosiphum euphorbiae, on feeding membranes was deterred by methanolic leaf rinses ofLycopersicon pennellii, or of its F₁ with tomato,L. esculentum. The active compounds in theL. pennellii rinsates were identified as 2,3,4-tri-O-acylglucoses bearing short to medium chain length fatty acids. These compounds are localized in the glandular exudate of the type IV trichomes and may accumulate to levels in excess of 400 g/cm². In choice assays, purified glucose esters fromL. pennellii reduced aphid settling at concentrations as low as 25 g/cm²; at concentrations of 150 g/cm² or more, all aphids avoided treated areas. Glucose esters were also active in deterring aphid settling in no-choice assays. At 100 g/ cm², these esters resulted in increased levels of mortality after 48 hr.     

Biological activity of synthetic hydrocarbon mixtures of cuticular components of the female housefly (Musca domestica L.)

Mixtures of (Z)-9-alkenes (C₂₁-C₃₃),n-alkanes (C₂₁-C₃₃), and mono- and dimethylalkanes (C₂₇, C₂₉), as components of the cuticular lipids washed from the female housefly (Musca domestica L.), were synthesized and assayed for their biological activity on male houseflies. The (Z)-9-alkenes and their hydrogenatedn-alkanes were synthesized from jojoba wax components by the appropriate chain elongation. The methylalkanes were prepared by Grignard coupling reaction of the appropriate alkyl halides, catalyzed by Li₂CuCl₄. Six- to 7-day-old virgin male houseflies exhibited the highest mating strike activity toward 6- to 7-day-old virgin females. The mating strike activity of the synthetic hydrocarbons was studied by exposing 6- to 7-day old virgin males to petrol-ether-rinsed 1 to 2-day-old dead females treated with these chemicals. (Z)-9-Tricosene was the most active hydrocarbon tested when it was applied in amounts of 10 g to a washed dead female. Amounts of 5 g of (Z)-9-tricosene did not cause sexual activity in the males. Mixture of (Z)-9-alkenes showed low activity when applied at 10-g amounts. However, when mixtures were made of 5 g of (Z)-9-tricosene with 5 fig of each of certain mixtures of (Z)-9-alkenes, the striking activity became as high as that of 10 g of (Z)-9-tricosene. This might be a synergism effect. The mixtures ofn-alkanes, as well as the mono- and dimethylalkanes, showed moderate activity. When (Z)-9-tricosene was added to these materials no increase in male activity was observed.     

Caste-dependent pheromones in the head of the antTetramorium caespitum

The heads of maleT. caespitum contain 4-methyl-3-hexanol (1.7 g, only the erythro isomer(s) detected) and 4-methyl-3-hexanone (0.8 g). The heads of alate females contain 0.1 g of each compound, whereas only the alcohol (0.1 g) was found in the heads of workers. Both compounds act as attractants for the workers and their possible functions are discussed.'Chargé de Recherche du F.N.R.S.Chercheur qualifié du F.N.R.S.     

Effect of formulations and dispensers on attractiveness of virelure to the tobacco budworm

Formulations of virelure, the synthetic sex pheromone of the tobacco budworm,Heliothis virescens (F.), were developed, bioassayed in traps in field cages, and used in traps to survey populations in plant hosts. Virelure (10 mg) laminated between thin sheets of vinyl polymer plastic was attractive to male moths for 21 days, and attractiveness did not regress appreciably for the first 7 days. Another dispenser was an 8 × 30-mm cigarette filter encased in a glass shell vial. A mixture of 10 l (Z)-11-hexadecenal and 0.5 l (Z)-9-tetradecenal, the pheromone components, formulated with wheat germ oil andd-alpha tocopherol (91) in 0.5 ml CH₂Cl₂ (WGOE) was still attractive to males after 5 days. Cottonseed oil, polyethylene glycol 600 distearate (peg-600-d), and peg-6000-d also inhibited excessive vaporization and oxidation of virelure. Virelure (21.25 l) formulated on filters with WGOE and used as bait (replaced weekly) in survey traps caught 27,263 males in 1975; analysis of catches each day for 7-day periods showed that most males were caught within 3 days after baiting, and attractiveness regressed considerably during the last 3–4 days of each week. Four ratios of virelure components were tested as bait (20 mg) in saucer-type pheromone traps, and the 161 ratio caught significantly more male moths than ratios of 241, 321, or 401.Lepidoptera Noctuidae.In cooperation with the Texas Agricultural Experiment Station, Texas A & M University, College Station 77843.This paper reports the results of research only. Mention of a pesticide in this paper does not constitute a recommendation for use by the USDA nor does it imply registration under FIFRA as amended. Also, mention of a commercial or a proprietary product in this paper does not constitute an endorsement by the USDA.     

Phytotoxicity of sorgoleone found in grain Sorghum root exudates

Root exudates ofSorghum bicolor consist primarily of a dihydroquinone that is quickly oxidized to ap-benzoquinone named sorgoleone. The aim of this investigation was to determine the potential activity of sorgoleone as an inhibitor of weed growth. Bioassays showed 125M sorgoleone reduced radicle elongation ofEragrostis tef. In liquid culture, 50-M sorgoleone treatments stunted the growth ofLemna minor. Over a 10-day treatment period, 10M sorgoleone in the nutrient medium reduced the growth of all weed seedlings tested:Abutilon theophrasti, Datura stramonium, Amaranthus retroflexus, Setaria viridis, Digitaria sanguinalis, andEchinochloa crusgalli. These data show sorgoleone has biological activity at extremely low concentrations, suggesting a strong contribution toSorghum allelopathy.     

Looplure efficacy and electrophysiological responses in three plusiinae species

Source concentration differences of (Z)-7-dodecen-1-ol acetate, or looplure, were evaluated for field trapping efficiency and electrophysiological responses with malePseudoplusia includens (Walker),Trichoplusia ni (Hubner) andRachiplusia ou (Guenné) (Lepidoptera: Noctuidae). Sticky traps baited with 1000 g of the lure captured a significantly greater (P < 0.05) number of maleP. includens andT. ni than any other concentration;R. ou males were caught at a greater rate in traps baited with 100 g of looplure, significantly more (P < 0.05) than with 1000 g. Electroantennogram (EAG) studies demonstrated that antennae of maleP. includens have a lower response threshold to looplure than eitherT. ni orR. ou antennae, the latter demonstrating the highest significant threshold of response. No differences in the stimulus-response functions of the three species were detected.Lepidoptera: Noctuidae.