Behavioral responses of male turnip moths,Agrotis segetum,to sex pheromone in a flight tunnel and in the field

The response of individual male turnip mothsAgrotis segetum was observed in a sustained flight tunnel to a mixture of decyl acetate, (Z)-5-decenyl acetate, (Z)-7-dodecenyl acetate, and (Z)-9-tetradecenyl acetate in proportions similar to those found in gland extracts from virgin females (0.6: 1:5:2.5). Lures containing 3–30 g (Z)-5-decenyl acetate proved to be maximally attractive, with approximately 60% of the males completing all behavioral steps from activation to copulation efforts. A 300-g dosage caused significant arrestment of upwind flight. Peak response to synthetics, however, was significantly lower than to female glands. Omitting decyl acetate from the blend did not affect the activity, while omission of any of the three monounsaturated acetates caused a dramatic decrease in response. In the field maximum trap catches were achieved with 1- to 30-g lures. The subtractive assay carried out in the field confirmed the neutrality of decyl acetate and the importance of the three monoenes. Adding 1% of (Z)-8-dodecenyl acetate (earlier reported as an inhibitor) to the four-component mixture decreased the trap catch to about 50%, and increasing the amount of (Z)-8-dodecenyl acetate to 27% decreased the activity further to about 10%. (Z)-8-Dodecenyl acetate also decreased the number of successful flights in the flight tunnel.Schiff., Lepidoptera: Noctuidae.This study was made within the Swedish project Odour Signals for Control of Pest Insects.     

Orientation of boll weevil,Anthonomus grandis boh. (Coleoptera: Curculionidae), to pheromone and volatile host compound in the laboratory

Behavioral responses of male and female boll weevils to the aggregation pheromone, grandlure, and the major volatile of cotton, -bisabolol, were investigated using a new dual-choice olfactometer. Dosage-response experiments revealed both males and females to be attracted by the aggregation pheromone at the 1.0 g dosage. However, only males were attracted to -bisabolol (1.0 g). Both sexes were repelled by the highest dosage of-bisabolol tested (10 g). In preference experiment, males chose grandlure over -bisabolol, while both sexes chose the combination of grandlure + -bisabolol over -bisabolol alone. There was some evidence for synergism between pheromone and plant odor for the females. The results correlate well with previous electrophysiological and behavioral experiments.Mention of a trademark, proprietary product, or vendor does not constitute a guarantee or warranty of the product by the U.S. Department of Agriculture and does not imply its approval to the exclusion of other products or vendors that may also be suitable.     

Evaluation of the synthetic major component of the sex pheromone of Tuta absoluta (Meyrick) (Lepidoptera: Gelechiidae)

In wind-tunnel bioassays, dispensers loaded with 1 g of the synthetic major component (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate (TDTA) of the sex pheromone emitted by Tuta absoluta (Meyrick) females were found to be highly attractive to conspecific males. Field experiments were conducted to evaluate the efficacy of five trap designs. The best trap, baited with 100 g of the synthetic sex pheromone caught on average 1200 males per trap per night, while those baited with virgin females caught only 201 males. The male response to this pheromone is restricted to the same early-morning time window during which females exhibit calling behavior. The high biological activity of the synthetic pheromone suggests that it could be useful for pest monitoring and in mating disruption.     

Quantitative and qualitative variation in male pheromones ofPhragmatobia fuliginosa andPyrrharctia isabella (Lepidoptera: Arctiidae)

The dihydropyrrolizine pheromones, hydroxydanaidal and danaidal, were identified from the scent organs of malePhragmatobia fuliginosa (L.) andPyrrharctia isabella (J.E. Smith). Qualitative and quantitative GLC analyses were conducted on ca. 80 field-collected males of each species. The total pheromone titer was distributed bimodally in each species with most males having either a small amount (< 10 ng) of pheromone or a large amount (1–10 g inPyrrharctia and 0.3–3 g inPhragmatobia).Pyrrharctia males in the 1- to 10-g range had a predominance of hydroxydanaidal, with little if any danaidal. MostPhragmatobia males in the 0.3- to 3-g range had danaidal with little if any hydroxydanaidal. These compounds elicited a courtship response in sexually receptive females of both species. A bioassay based on this response was used to measure the thresholds of female response to these compounds.Pyrrharctia females were more sensitive to (R)-(–)-hydroxydanaidal than to danaidal.Phragmatobia females were more sensitive to danaidal then to (R)-(–)-hydroxydanaidal.     

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.     

Sex pheromone components of the blueberry leaftier mothCroesia curvalana kearfott (Lepidoptera: Tortricidae)

The GC-MS and GC-EAD analyses of sex-gland components and sex-gland-released volatiles have identified (E)- and (Z)-11-tetradecenal (9010) and (E)- and (Z)-11-tetradecenyl acetate (8515) as components of the sex pheromone chemical communication system ofCroesia curvalana (Kearfott). The aldehyde-to-acetate ratio of 91 was found in the gland-released components. This blend at a 0.1–1 g/day release rate from PVC lures was shown to be as effective as virgin females in the trapping of maleC. curvalana.     

Oriental fruit moth pheromone component emission rates measured after collection by glass-surface adsorption

We collected and quantified both synthetic and natural Oriental fruit moth [Grapholitha molesta (Busck)] sex pheromone components in 250-ml round-bottom flasks by hexane rinsing of compounds adsorbed on the glass walls. This simple procedure collected 100% of the pheromone evaporated inside the flask and was useful for quantifying both nanogram and microgram amounts of emitted pheromone. Emission rates of (Z)-8-dodecenyl acetate from 1000, 100, and 10 g-loaded rubber septa were 219, 12, and 1.2 ng/hr, respectively.G. molesta females emitted this component at 3.2 ng/hr, close to the emission rate from a 10 g-loaded septum, which evokes long-range and close-range behaviors in the male. The corresponding alcohol, (Z)-8-dodecenyl alcohol, was emitted from rubber septa ca. 3 times faster than the acetate.Lepidoptera: Tortricidae.Paper of the Michigan State Agricultural Experiment Station.     

Onion fly trap catch as affected by release rates ofn-dipropyl disulfide from polyethylene enclosures

n-Dipropyl disulfide loadings of at least 1 l and 10 l in polyethylene enclosures were required to effect significant trap catches of onion fly,Hylemya antiqua (Meigen), females and males, respectively. Corresponding release rates for this threshold for trap catch were ca. 100 g/hr. Catches increased with loadings up to 100 l/capsule but then plateaued. As determined gravimetrically, the release rate from enclosures containing a reservoir of chemical remained constant under isothermal conditions but increased exponentially as a function of temperature.Diptera: AnthomyiidaePaper No. 9422 of the Michigan State University Agricultural Experiment Station. Received for publication April 29, 1980.     

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.     

Aggregation Pheromone of the Cereal Leaf Beetle: Field Evaluation and Emission from Males in the Laboratory

The previously identified, male-specific compound of the cereal leaf beetle (CLB, Chrysomelidae; Oulema melanopus), (E)-8-hydroxy-6-methyl-6-octen-3-one, was studied further with respect to field activity and emission rate from male beetles. In a 5-week field experiment in Oregon, the compound was shown to function as an aggregation pheromone in attracting male and female CLBs migrating from overwintering sites in spring. Traps baited with the synthetic compound (500 g per rubber septum) caught 3.3 times more CLBs than control traps. Lower doses of the pheromone (50 and 150 g) were less attractive than the 500 g dose. One relatively abundant, volatile compound from the host plant (oats), (Z)-3-hexenyl acetate, that elicited responses from beetle antennae was not attractive, either by itself or as a synergist of the pheromone. Both sexes were captured about equally for all treatments. We also measured daily pheromone emission by male beetles in the laboratory. Individual males feeding on oat seedlings under greenhouse conditions emitted as much as 6 g per day, which is about 500 times higher than had been previously observed under incubator conditions. The pheromone emission rate was at least five times higher during the day than at night, and in one male, emission spanned a period of 28 d. The release rate of synthetic pheromone from the 500 g septa was very similar to the maximum from single males; thus, future experiments should evaluate even higher doses. The field results indicate that the pheromone has potential as a monitoring tool for early detection of CLBs as they move from their overwintering sites into newly planted cereal crops in spring.     

Sex pheromone of purplestriped shootworm,Zeiraphera unfortunana powell

The analyses of virgin female sex pheromone gland extracts and gland volatiles by GC, GC-EAD and GC-MS, followed by field trapping experiments, have identified (E)-9-dodecenyl acetate (E9–12Ac) as the primary sex pheromone component of the purplestriped shootworm,Zeiraphera unfortunana. Dosages of 1.0–10.0 g ofE9–12Ac impregnated in rubber septa provide an effective trap bait and can be used for monitoring purposes.Lepidoptera: Tortricidae.     

Female sex pheromone of the german cockroach,Blattella germanica (L.) (Orthoptera: Blattellidae), responsible for male wing-raising II. 29-Hydroxy-3,11-dimethyl-2-nonacosanone

One component of the sex pheromone responsible for wing-raising in courtship behaviors ofBlattella germanica males was isolated from cuticular wax of the mature females and identified as 29-hydroxy-3,11-dimethyl-2-nonacosanone. This component showed the activity at a concentration as low as 3 g/ml in carbon tetrachloride on the behavioral bioassay.     

Identification of sex pheromone of browntail moth,Euproctis chrysorrhoea (L.) (Lepidoptera: Lymantriidae)

A unique sex attractant pheromone was isolated and identified from extracts of ovipositor tips from the female browntail moth (Lepidoptera: Lymantriidae). The pheromone compound, (Z,Z,Z,Z)-7,13,16,19-docosatetraen-1-ol isobutyrate, CH₃CH₂CH=CHCH₂CH=CHCH₂CH= CH(CH₂)₄CH=CH(CH₂)₆O₂CCH(CH₃)₂, was identified by a combination of gas chromatography, mass spectrometry, and microreactions and was confirmed by synthesis. Traps baited with 5–50 g of the synthetic pheromone, dispensed from rubber septa treated with an antioxidant and a UV stabilizer, gave male moth captures that were comparable to traps baited with three virgin females. Higher (250 g) and lower (0.04–2.5 g quantities of the synthetic pheromone on septa captured somewhat fewer males. Captures were the same for similar quantities of the natural and synthetic pheromone. Minor, inactive components in the tip extract were identified as a mixture of 7- and 8-pentacosanone.     

Behavioral response of male white peach scale to the sex pheromone, (R,Z)-3,9,-dimethyl-6-isopropenyl-3,9-decadien-1-ol propionate and corresponding alcohol

Males of the white peach scale,Pseudaulacaspis pentagona (Tar-gioni-Tozzetti), in Florida differ from this scale in France in their responses to putative pheromonal chemicals presented in a laboratory bioassay. Males from Florida were attracted to, and exhibited sexual (coputatory) behaviors at, the locus of evaporation of (R,Z)-3,9-dimethyl-6-isopropenyl-3,9-deca-dien-1-ol propionate (P) (previously identified from effluvia of Florida females). Addition of the corresponding primary alcohol (A) to the propionate did not alter the attraction of Florida males to the synthetic P and did not alter their sexual responses from those exhibited by males exposed to P alone. In contrast, the effluvia from French scales has been reported to contain P and A, and the alcohol has been reported in laboratory studies to be required to release sexual behavior in French males. This suggests that the conspecific status of the scale in Florida and France should be reexamined. Field trap baits with 2.5 g of a 1 1 mixture of P and A captured significantly fewer Florida males than traps baited with 1.25 g of P alone, but traps similarly baited with 0.125 g of each material captured the same number of insects as traps baited with 0.125 g of P alone.Mention of a commerical or proprietary product in this paper does not constitute an endorsement of that product by the USDA.     

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.     

Effect of juvenile hormone analog,fenoxycarb, on pheromone production byIps paraconfusus (Coleoptera: Scolytidae)

Topical application of the juvenile hormone analog, fenoxycarb, in acetone induced newly emerged male California five-spined ips,Ips paraconfusus Lanier, to become attractive to females, as measured by positive responses to male abdominal extracts in a laboratory bioassay. Two pheromones, ipsdienol and ipsenol, were detected by gas chromatography in the abdominal extracts of fenoxycarb-treated males. Pheromone production was minimal at a dose of 0.1 g/insect of fenoxycarb, maximal at 10 g, and was reduced to unmeasurable amounts at a dose of 100 g. In comparison, peak production of pheromones was induced at a dose of 0.1 g/insect of natural juvenile hormone (JH III). Treatment with 10 g of fenoxycarb resulted in the occurrence of pheromones 12 hr after exposure, maximal pheromone content between 16 and 20 hr, and undetectable amounts after 36 hr. The demonstration that fenoxycarb is an active juvenile hormone analog for a bark beetle suggests that it may have practical utility in managing these insects.     

Biosynthesis,production site,and emission rates of aggregation-attachment pheromone in males of twoAmblyomma ticks

The aggregation-attachment pheromone componentso-nitrophenol (ONP) and methyl salicylate (MS) in maleAmblyomma variegatum ticks appeared after three days of feeding on the host and reached high values after about six days. Variable quantities of 1.3–7.3 g ONP and about 0.6 g MS were present within ticks. ONP and MS were released at the high rates of 300–1800 ng/hr and 20–600 ng/hr per male tick, respectively. After a temporary decrease, males continued to emit at high rates after nearby attachment of females. InA. hebraeum, ONP showed a similar pattern, but with a delay of about a day. A male, which had fed during 14 days, contained about 2 g and released 225–280 ng/hr. Emission in forcibly detached males of both species dropped rapidly to low levels of less than 10 ng/hr per tick. Host skin and tick feces in the vicinity of feeding males were pheromoneimpregnated. The very high emission rates are consistent with the observations that the pheromone is an important component of the host-location mechanism of conspecifics. ONP and MS are produced in the dermal glands type 2 associated with the ventrolateral cuticle.     

Sex pheromone of the European grapevine moth,Lobesia botrana Schiff. (Lepidoptera: Tortricidae): Synthesis and effect of isomeric purity on biological activity

A short synthesis of (E, Z)-7,9-dodecadien-1-yl acetate from propargyl alcohol and 6-bromohexanol via acetylenic-allenic isomerization of the resulting bis-THP-1,9-non-2-yn-diol is described. The field test of several preparations showed that theE,E isomer does not interfere with the biological activity of the pheromone. It was found that the crude preparation has higher activity than purified pheromone or virgin females.     

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.     

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.