Chemicals related to the gypsy moth sex pheromone as attractants and as synergists or inhibitors of the pheromone

Sheads, R. E.; Beroza, Morton; Paszek, E. C.

doi:10.1021/jf60197a030

Cited by 9 publications

(5 citation statements)

References 6 publications

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“…All other treatments were statistically indistinguishable at the 5 % level from unbaited traps. These data are in contrast to the high trap counts [relative to (±) -disparlure] for the compounds in treatments 13-17 reported by Sheads et al (1975). The epoxides of treatments 10-12 had been evaluated by other tests (Schneider et al 1972, Adler et al 1972) with results similar to ours.…”

Section: Resultssupporting

confidence: 70%

“…In the tests of Sheads et al (1975), overloading of small traps (10 cm long X 5 cm diam) may have depressed the catches of (±) -disparlure. As Sheads et al utilized no unbaited traps and did not analyze their data statistically, their postive trap catches are difficult to interpret.…”

Section: Resultsmentioning

confidence: 99%

“…The other (Z) alkenes were prepared in a similar manner from the appropriate starting materials. Compounds of treatments 13-17 were prepared by the procedures of Sheads et al (1975) and were of comparable purity. The trioctanoin was obtained from Eastman Organic Chemicals.…”

Section: Chemicalsmentioning

confidence: 99%

“…Sarmiento et al (1972), Adler et al (1972) and Schneider et al (1974) reported that (±) -epoxide analogues of disparlure were only slightly attractive when contrasted with (±) -disparlure. Sheads et al (1975) evaluated the attractancy of diverse compounds structurally similar to disparlure but lacking the epoxide moiety. Sheads et aI. suggested that receptor response is not completely specific to the epoxy group, because these analogues possessed attractancy levels below that of (±) -disparlure but apparently above those of the (± )-epoxide analogues.…”

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confidence: 99%

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Attractancy of Racemic Disparlure and Certain Analogues to Male Gypsy Moths1 and the Effect of Trap Placement

Cardé¹,

Doane²,

Granett³

et al. 1977

Environmental Entomology

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Traps hung on small trees of 3-8 cm diam and baited with racemic epoxides, hydrocarbons and other analogues related to racemic cis-7,8-epoxy-2-methyloctadecane (disparlure) resulted in male Lymantria dispar L. (gypsy moth) catches statistically indistinguishable from those of unbaited traps. Only (±)-disparlure yielded trap catches statistically above the level of unbaited traps. However, trap placement on trees of ca. 0.5 m diam produced appreciable trap catches, even in unbaited traps.The female-emitted pheromone of the gypsy moth, Lymantria dispar L., was characterized as cis-7,8-epoxy-2-methyloctadecane and named "disparlure" (Bierl et al. 1970). Sarmiento et al. (1972), Adler et al. (1972) and Schneider et al. (1974) reported that (±) -epoxide analogues of disparlure were only slightly attractive when contrasted with (±) -disparlure. Sheads et al. (1975) evaluated the attractancy of diverse compounds structurally similar to disparlure but lacking the epoxide moiety. Sheads et aI. suggested that receptor response is not completely specific to the epoxy group, because these analogues possessed attractancy levels below that of (±) -disparlure but apparently above those of the (± )-epoxide analogues. We report here an investigation of the male trap-catch evoked by certain of these and other compounds related to disparlure. Materials and Methods ChemicalsThe (±)-disparlure and 2-methyl-(Z)-7-octadecene were obtained from Farchan Chemicals and contained 15% (E) isomers. The 2-methyl alkanes (Table 2, Treatments 7-8) were obtained from K and K Laboratories. The (±)-cis-8,9-epoxy-2-methyloctadecane (Treatment 9) was supplied by Zoe con Corporation. The epoxides of treatments 10-12 were prepared by epoxidation of the corresponding olefins 1 Lepidoptera: Lymantriidae.Received for publication May 18, 1977.• Department of Entomology, New York State Agricultural Experiment Station, Geneva 14456.• Present address: Department of Entomology, Michigan State University, East Lansing 48824.• Department of Entomology, The Connecticut Agricultural Experiment Station, New Haven 06504.• Present address: Department of Entomology, University of Maine, Orono 04473.• Present address: USDA, ARS, Beltsville, MD 20705.with m-chloroperbenzoic acid in benzene and were of >95% purity. The 2-methyl-(Z)-6-octadecene was obtained by reaction of triphenyl(6-methylheptyl) phosphonium bromide in DMF with sodium methoxide and dodecanal. The other (Z) alkenes were prepared in a similar manner from the appropriate starting materials. Compounds of treatments 13-17 were prepared by the procedures of Sheads et al. (1975) and were of comparable purity. The trioctanoin was obtained from Eastman Organic Chemicals. All compounds were racemic where optical activity is formally possible. Field TestsTrapping was conducted in oak forests (Quercus spp.) in Wolf's Den State Park in Pomfret, Conn. in July, 1975. All test chemicals were dispensed in 100 p.l petroleum ether either onto cotton wicks of 1 cm diam X 1 cm length or onto 5 X9-mm rubber septa (A...

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Section: Resultssupporting

confidence: 70%

Section: Resultsmentioning

confidence: 99%

Section: Chemicalsmentioning

confidence: 99%

mentioning

confidence: 99%

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Attractancy of Racemic Disparlure and Certain Analogues to Male Gypsy Moths1 and the Effect of Trap Placement

Cardé¹,

Doane²,

Granett³

et al. 1977

Environmental Entomology

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“…As prices of vegetable oils come within the price range of petroleum products, they can compete as solvents or be used as cosolvents to conserve the use of petroleum products. Fatty nitrogen derivatives have been found to act as abscission agents in the harvest of citrus, to increase sugar in sugar cane and sugarbeets, and to act as insect sex lures, to name a few (31,32).…”

Section: Future Of Fats and Oilsmentioning

confidence: 99%

Fats and oils in agriculture

Abramitis¹

1977

J Americ Oil Chem Soc

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AND SUMMARYFats, oils, and their derivatives are reviewed, in their roles as emulsifiers and surfactants and as pesticide derivatives, and in their activity per se. As emulsifiers and surfactants they offer a wide range of hydrophile-lipophile balance (HLB) values to assist formulators in developing saleable products. Their lipoid solubilities aid in evaporation retardation, plant penetration, and absorption. Often they greatly improve the performance of the active ingredients. Nitrogen derivatives such as amines and quaternaries, fatty alcohols, acid esters, and other agricultural chemicals are reviewed. Examples are cited on the effect of the length of the carbon chain and their number in such herbicides as 2,4-D and dalapon, as well as the biological properties of various aliphatic groups in insect larvicides, plant growth regulators, and fungicides. The role vegetable oils can play in the looming energy shortages as petroleum oil substitutes is discussed. They offer a challenging future in agricultural applications.

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Simmons‐Smith Cyclopropanation Reaction

2001

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Almost 30 years after Emschwiller prepared IZnCH 2 I, Simmons and Smith discovered that the reagent formed by mixing a zinc‐copper couple with CH 2 I 2 in ether could be used for the stereospecific conversion of alkenes to cyclopropanes. Nowadays, the Simmons‐Smith cyclopropanation reaction is one of the most widely used reactions in the organic chemist's arsenal for the conversion of olefins into cyclopropanes. This popularity is mainly due to the stereospecificity of the reaction with respect to the double bond geometry and its compatibility with a wide range of functional groups. The chemoselectivity of the reaction toward some olefins is excellent and very few side reactions are observed with functionalized substrates. The metal carbenoid is electrophilic in nature and electron‐rich alkenes usually react much faster than electron‐poor alkenes. Furthermore, the ability to use proximal hydroxy or ether groups to dictate the stereochemical outcome of the CC bond forming process was recognized early on, and this unique property has been successfully exploited on numerous occasions. It has been recognized that halomethylmetal reagents are powerful synthetic tools for the stereoselective addition of a methylene unit to chiral acyclic allylic alcohols and allylic ethers. In addition, the use of halomethylzinc reagents in the presence of chiral additives is one of the few ways to cyclopropanate allylic alcohols efficiently and with good enantiocontrol. Carbenoids can be divided into the following two classes: (1) those of general structure MCH 2 X and (2) those corresponding to M = CH 2 . This chapter is focussed exclusively on the first class in which M = Zn, Sm, or Al. Although other metal carbenoids of type MCH 2 X, such as those derived from Cu, Cd, Hg, and In, have been reported to be effective reagents for the cyclopropanation of some olefins, they have been used only sporadically, and this review does not highlight these reactions. This chapter covers cyclopropanation reactions involving haloalkylzinc, aluminum, and samarium reagents published since the comprehensive chapter in Organic Reactions by Simmons that surveyed the literature up to 1973.

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Chemicals related to the gypsy moth sex pheromone as attractants and as synergists or inhibitors of the pheromone

Abstract: Seven compounds and 11 isomeric mixtures related to disparlure, the sex pheromone of the gypsy moth [Porthetria dispar (L.)], were synthesized and tested in the field both alone and in combination with disparlure to determine their activity as attractants and as synergists or inhibi-

Cited by 9 publications

References 6 publications

Attractancy of Racemic Disparlure and Certain Analogues to Male Gypsy Moths1 and the Effect of Trap Placement

Attractancy of Racemic Disparlure and Certain Analogues to Male Gypsy Moths1 and the Effect of Trap Placement

Fats and oils in agriculture

Simmons‐Smith Cyclopropanation Reaction

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