Abstract
“The ultimate practical goal of pheromone research on insect pests is to place the communication system on a molecular basis and to use the knowledge to detect, survey, trap, or disrupt the population” (Silverstein, 1982). Achievement of this goal requires the combined efforts of entomologists working in behavior and ecology and analytical and synthetic organic chemists. Analytical chemistry is the indispensable link between field ecology, the observation of pheromone induced behavior, and the development of a bioassay on one hand and field application of the synthesized pheromone on the other. Thus the success of a pheromone project often depends on the proper selection of analytical procedures for isolation and identification of the biologically active compound (s) and for evaluation of the purity and structural congruity of the synthesized pheromone.
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References
Beroza M (1975) Microanalytical methodology relating to the identification of insect sex pheromones and related behavior-control chemicals. J Chromatogr Sci 13: 314–321.
Brand JM, Young JC, Silverstein RM (1979) Insect pheromones; A critical review of recent advances in their chemistry, biology, and application. In: Progress in the Chemistry of Organic Natural Products; Vol 37. Herz W, Grisebach H, Kirby GW (eds), Springer-Verlag, Wien-New York.
Brownlee RG, Silverstein RM (1968) A micro preparative gas chromatograph and a modified carbon skeleton determinator. Anal Chem 40: 2077–2079.
Budzikiewicz H, Djerassi C, Williams DH (1967) Mass Spectrometry of Organic Compounds. Hold en-Day, San Francisco, California.
Byrne KJ, Gore WF, Pearce GT, Silverstein RM (1975) Porapak Q collection of airborne organic compounds serving as models for insect pheromones. J Chem Ecol 1: 1–7.
Cross JH, Byler RC, Cassidy RF, Jr, Silverstein RM, Greenblatt, RE, Burkholder WE, Levinson AR, Levinson HZ (1976) Porapak-Q collection of pheromone components and isolation of (Z)- and (E)-14-methyl-S-hexadecenal, sex pheromone components, from females of four species of Trogoderma (Coleoptera:Dermestidae). J Chem Ecol 2: 457–468.
Ettre LS (1965) Open Tubular Columns in Gas Chromatography. Plenum, New York.
Guss PL, Tumlinson JH, Sonnet PE, McLaughlin JR (1983) Identification of female produced sex pheromone from the Southern corn rootworm, Diabrotica undecimpunctata howardi Barber. J Chem Ecol 9: 1363–1375.
Heath RR, Sonnet PE (1980) Technique for in situ coating of Ag+ onto silica gel in HPLC columns for the separation of geometrical isomers. J Liquid Chromatogr 3: 1129–1 135.
Heath RR, Jordan JR, Sonnet PE (1981) Effect of film thickness and supercooling on the performance of cholesteryl cinnamate liquid crystal capillary columns. High Resol Chromatogr Chromatogr Comm 4: 328–332.
Heath RR, Tumlinson JH, Leppla NC, McLaughlin JR, Dueben B, Dundulis EA, Guy RH (1983) Identification of a sex pheromone produced by female velvetbean caterpillar moths. J Chem Ecol 9: 645–656.
Hill AS, Cardé RT, Kido H, Roelofs WL (1975) Sex pheromone of the orange tortrix moth, Argyrotaenia citrana (Lepidoptera:Tortricidae). J Chem Ecol 1: 215–224.
Hunt DF, Ryan JF, III (1971) Chemical ionization mass spectrometry studies. I. Identification of alcohols. Tetrahedron Lett 4535–4538.
Hunt DF, Ryan JF, III (1972a) Argon-water mixtures as reagents for chemical ionization mass spectrometry. Anal Chem 44: 1306–1309.
Hunt DF, Ryan JF, III (1972b) Chemical ionization mass spectrometry studies. Nitric oxide as a reagent gas. J Chem Soc Chem Commun 620–621.
Klun JA, Bierl-Leonhardt BA, Plimmer JR, Sparks AN, Primiani M, Chapman OL, Lepone G, Lee GH (1980) Sex pheromone chemistry of the female tobacco budworm moth, Heliothis virescens. J Chem Ecol 6: 177–183.
Leibrand RJ, Dunham LL (1973) Preparing high efficiency packed GC columns. Research/Development, September. 32–38.
Ma M, Hummel HE, Burkholder WE (1980) Estimation of single formiline carpet beetle (Anthrenus flavipes LeConte) sex pheromone release by dose-response curve and chromatographic analysis of pentafluorobenzyl derivative of (Z)-3-decanoic acid. J Chem Ecol 6: 597–607.
Majors RE (1972) High performance liquid chromatography on small particle silica gel. Anal Chem 44: 1722–1728.
Phelan PL, Miller JR (1981) Separation of isomeric insect pheromonal compounds using reversed-phase HPLC with AgN03 in the mobile phase. J Chromatogr Sci 19: 13–17.
Rocca JR, Tumlinson JH, Glancey BM, Lofgren C (1983) The queen recognition pheromone of Solenopsis invicta, preparation of (E)-6-(l-pentenyl)-2H- pyran-2-one. Tetrahedron Lett 24: 1889–1892.
Silverstein RM, Bassler GC, Morrill TC (1981) Spectrometric Identification of Organic Compounds. 4th ed. Wiley, New York.
Silverstein RM (1982) Chemical communications in insects: Background and application. Pure Appl Chem 54: 2480–2481.
Scott RPW, Kucera P (1974) The examination of some commercially available silica gel adsorbents for use in liquid solid chromatography. J Chem Sci 12: 473–485.
Scott RPW (1960) Gas chromatography, p. 144. Proceedings 3rd Int. Symposium. Butterworths, London.
Sower LL, Coffelt JA, Vick KW (1973) Sex pheromone: A simple method of obtaining relatively pure material from females of five species of moths. J Econ Entomol 66: 1220–1222.
Tumlinson JH, Hardee DD, Gueldner RC, Thompson AC, Hedin PA, Minyard JP (1969) Sex pheromone produced by male boll weevil: Isolation, identification, and synthesis. Science 166: 1010–1012.
Tumlinson JH, Heath RR, Teal PEA (1982) Analysis of chemical communications systems of Lepidoptera. In: Insect Pheromone Technology: Chemistry and Applications. Leonhardt B, Beroza M (eds), ACS Symposium Series, Am. Chem. Soc., Washington, D.C., pp 1–25.
Young JC, Silverstein RM (1975) Biological and chemical methodology in the study of insect communication. In: Methods in Olfactory Research. Moulton DG, Turk A, Johnston JW (eds), Academic Press, New York, pp 75–161.
Purification of Biologically Active Material
Dean JA (1963) Chemical Separation Methods. Reinhold, New York.
Overton KH (1963) Isolation, purification, and preliminary observations. In: Technique of Organic Chemistry. Weissberger A (ed), Interscience, New York.
Pasto DJ, Johnson CR (1969) Physical methods of separation, purification and characterization. In: Organic Structure Determination. Prentice-Hall, New Jersey.
Pasto DJ, Johnson CR (1969) Physical methods of separation, purification and characterization. In: Organic Structure Determination. Prentice-Hall, New Jersey.
Tumlinson JH, Heath RR (1976) Structure elucidation of insect pheromones by microanalytical methods. J Chem Ecol 2: 87–99.
Young JC, Silverstein RM (1975) Biological and chemical methodology in the study of insect communication. In: Methods of Olfactory Research. Moulton DG, Turk A, Johnston JW (eds), Academic Press, New York, pp 75–161.
Liquid Chromatography
Adams MA, Nakanishi K (1979) Selected uses of HPLC for the separation of natural products. J Liquid Chromatogr 2: 1097–1136.
Anonymous (1979) Preparative Liquid Chromatography. Waters Associates, Framingham, Massachusetts.
Bakalyan S, Yuen J, Henry D (1977) How to Pack Liquid Chromatography Columns. Spectra Physics Corp, San Jose, California.
Done JN, Knox IH, Loheac J (1982) Application of High-Speed Liquid Chromatography. Wiley-Interscience, New York.
Hamilton RJ, Sewell PA (1982) Introduction to High Performance Liquid Chromatography. Chapman and Hall/Methuen Inc., New York.
Kaiser RE, Oelrich E (1981) Optimization in HPLC. Dr. Alfred Huethig Publishers, New York.
Kirkland II (1971) Report for analytical chemists. Anal Chem 43: 37A–48A.
Laub RJ (1974) Packings for HPLC. Research/Development 14: 24–28.
Schram SB (1980) The LDC Basic Book on Liquid Chromatography. Milton Roy Company, St. Petersburg, Florida.
Snyder LR, Kirkland JJ (1974) Introduction to Modern Liquid Chromatography. Wiley, New York.
Snyder LR (1972) A rapid approach to selecting the best experimental conditions for high-speed liquid column chromatography. Part II. Estimating column length, operating pressure and separation time for some required sample resolution. J Chromatogr Sci 10: 369–379.
Yost RW, Ettre LS, Conlon RD (1980) Practical Liquid Chromatography: An Introduction. Perkin-Elmer, Norwalk, Connecticut.
Gel Permeation
Anonymous (1983) Chromatography, electrophoresis, immunochemistry and HPLC. Bio-Rad, New York.
Anonymous (1978) Aquapou™ sep columns: Rapid aqueous and non-aqueous size exclusion chromatography. Brownlee Labs, Santa Clara, California.
Anonymous (1973) Liquid Chromatography: Packing Materials and Packed Columns. Waters Associates, Framingham, Massachusetts.
Kirkland JJ, Antle PE (1977) High performance size-exclusion chromatography of small molecules with columns of porous silica microspheres. J Chromatogr Sci 15: 137–147.
Krishen A, Tucker RG (1977) Gel permeation chromatography of low molecular weight materials with high efficiency columns. Anal Chem 49: 898–902.
Adsorption on Silica Gel
Majors RE (1972) High performance liquid chromatography on small particle silica gel. Anal Chem 44: 1722–1726.
Rabel FM (1975) Microparticle packings for liquid chromatography. Use and care. Am Lab 15: 53–63.
Saunders DL (1974) Solvent selection in liquid chromatography. Anal Chem 46: 470–473.
Scott RPW, Kucera P (1974) The examination of some commercially available silica gel adsorbents for use in liquid solid chromatography. J Chromatogr Sci 12: 473–485.
Reverse-Phase Chromatography
Colin H, Guiochon G (1978) Comparison of some packings for reversed-phase high-performance liquid-solid chromatography. II. Some theoretical considerations. J Chromatogr 158: 183–205.
Harrison KH, Millar VI, Yates TL (1982) Comprehensive guide to reverse phase materials for HPLC. Vydac, Hesperia, California.
Schmit RA, Henry RA, Williams RC, Dieckman JF (1971) Application of high speed reversed-phase liquid chromatography. J Chromatogr Sci 9: 645–651.
Complexation Chromatography
Evershed RP, Morgan ED, Thompson LD (1982) Preparative scale separation of alkene geometric isomers by liquid chromatography. J Chromatogr 237: 350–354.
Heath RR, Sonnet PE (1980) Technique for in situ coating of Ag+ onto silica gel in HPLC columns for the separation of geometrical isomers. J Liquid Chromatogr 3: 1129–1135.
Heath RR, Tumlinson JH, Doolittle RE, Proveaux AT (1975) Silver nitrate-high pressure liquid chromatography of geometrical isomers. J Chromatogr Sci 13: 380–382.
Heath RR, Tumlinson JH, Doolittle RE (1977) Analytical and preparative separation of geometrical isomers by high efficiency silver nitrate liquid chromatography. J Chromatogr Sci 15: 10–13.
Houx NWH, Jongen WMF (1974) Purification and analysis of synthetic insect sex attractants by liquid chromatography on a silver loaded resin. J Chromatogr Sci 96: 25–32.
Janak J, Jagaric Z, Dressier M (1970) Use of olefin-Ag+ complexes for chromatographic separations of higher olefins in liquid-solid system. J Chromatogr 53: 525–530.
Morris LJ, Wharry DM, Hammond EW (1967) Chromatographic behavior of isomeric long-chain aliphatic compounds. II. Argentation thin-layer chromatography of isomeric octadecenoates. J Chromatogr 31: 69–76.
Phelan PL, Miller JR (1981) Separation of isomeric insect pheromonal compounds using reversed-phase HPLC with AgN03 in the mobile phase. J Chromatogr Sci 19: 13–17.
Schomburg G, Zegarski K (1975) Separation of olefinic compounds by reversed-phase liquid chromatography with a mobile phase containing π-complexing metal salts like silver nitrate. J Chromatogr 114:174–178.
Tscherne RJ, Capitano G (1977) High-pressure liquid chromatographic separation of pharmaceutical compounds using a mobile phase containing silver nitrate. J Chromatogr 136: 337–341.
Vonach B, Schomburg G (1978) High-performance liquid chromatography with Ag+ complexation in the mobile phase. J Chromatogr 149:417–430.
Warthen JD, Jr (1976) Liquid chromatographic purification of geometric isomers on reverse-phase and silver-loaded macroporous cation exchange columns. J Chromatogr Sci 14: 513–515.
Gas-Liquid Chromatography
Anonymous (1968) Preparation of coated packings. Use of the HI-EFF® fluidizer. Applied Science Laboratories, State College, Pennsylvania.
Freeman RR (1979) High Resolution Gas Chromatography. Hewlett-Packard, Avondale, Pennsylvania.
Heath RR, Burnsed GE, Tumlinson JH, Doolittle RE (1980) Separation of a series of positional and geometrical isomers of olefinic aliphatic primary alcohols and acetates by capillary gas chromatography. J Chromatogr 189: 199–208.
Heath RR, Doolittle RE (1983) Derivatives of cholesterol cinnamate: A comparison of the separations of geometrical isomers when used as gas chromatographic stationary phases. High Resol Chromatogr Chromatogr Comm 6: 16–19.
Heath RR, Jordan JR, Sonnet PE (1981) Effect of film thickness and supercooling on the performance of cholesteryl cinnamate liquid crystal capillary columns. HRC CC 4: 328–332.
Heath RR, Jordan JR, Sonnet PE, Tumlinson JH (1979) Potential for the separation of insect pheromones by gas chromatography on columns coated with cholesteryl cinnamate. J High Resol Chromatogr Chromatogr Comm 2: 712–714.
Jennings W (1978) Gas Chromatography with Glass Capillary Columns. Academic Press, New York.
Kruppa RF, Henly RS, Smead DL (1967) Improved gas chromatography packing with fluidized drying. Anal Chem 39: 851–853.
Lester R, Hall DR (1980) 4-(p-Methoxycinnamyloxy)-4’-methoxyazobenzene: A nematic liquid crystal for the gas-liquid chromatographic analysis of the stereochemistry of lepidopterous sex pheromones and related unsaturated fatty alcohols and derivatives. J Chromatogr 190:35–41.
Lester R (1978) Smectic liquid crystal for the gas-liquid chromatographic separation of lepidopterous sex pheromones and related isomeric olefins. J Chromatogr 156: 55–62.
Littlewood AB (1962) Gas chromatography. Academic Press, New York.
Mon TR (1971) Preparation of large bore open tubular columns for GC. Res Devel 12: 14–17.
Said SD (1981) Theory and Mathematics of Chromatography. Hüthig, Heidelberg, West Germany.
Scott RPW (1970) Determination of the optimum conditions to effect a separation by gas chromatography. In: Advances in Chromatography. Giddings JC, Keller RA (eds), Dekker, New York, Vol 9.
Tumlinson JH, Heath RR, Teal PEA (1982) Analysis of chemical communications systems of Lepidoptera. ACS Symp. Series No. 190 Insect pheromone technology. Chemistry and Applications. Amer Chem Soc., Washington, DC, pp 1–25.
Zielinski WL, Jr (1980) Difficult isomer separations. Res Dev 22: 177–182.
Spectroscopic Methods
Dyer JR (1965) Applications of Absorption Spectroscopy of Organic Compounds. Prentice-Hall, Englewood Cliffs, New Jersey.
Pasto DJ, Johnson CR (1969) Organic Structure Determination. Prentice-Hall, Englewood Cliffs, New Jersey.
Silverstein RM, Bassler GC, Morrill TC (1981) Spectrometry Identification of Organic Compounds. 4th ed. Wiley, New York, p 444.
Mass Spectroscopy
Beynon JH, Saunders RA, Williams AE (1968) The Mass Spectra of Organic Molecules. American Elsevier, New York.
Biemann K (1962) Mass spectrometry: Organic chemical applications. McGraw-Hill, New York.
Budzikiewicz H, Buske E (1980) Studies in chemical ionization mass spectroscopy III, CI spectra of olefins. Tetrahedron 36: 255–266.
Budzikiewicz H, Djerassi C, Williams DH (1967) Mass Spectrometry of Organic Compounds. Holden-Day, San Francisco, California.
Foltz RL (1975) Structural analysis via chemical ionization mass spectrometry. Chemtech 14: 39–44.
Hunt DF (1976) Selective reagents for chemical ionization mass spectrometry. Finnigan Spectra 6: 1–8.
Leonhardt BA, De Vilbiss ED, Klun J A (1983) GC-MS indication of double-bond position in monounsaturated primary acetates and alcohols without derivatization. Org Mass Spec 18: 9–11.
Milne GWA (1971) Mass Spectrometry: Techniques and Applications. Wiley-Interscience, New York.
Tumlinson JH, Heath RR, Doolittle RE (1974) Application of chemical ionization mass spectrometry of epoxides for the determination of olefin position in aliphatic chains. Anal Chem 46: 1309–1311.
Infrared Spectroscopy
Conley RT (1972) Intrared Spectroscopy. 2nd ed. Allyn and Bacon, Boston.
Griffiths PR (1975) Chemical Infrared Fourier Transform Spectroscopy. Wiley- Interscience, New York.
Griffiths PR (1976) On-line measurement of the infrared spectra of gas chromatographic eluents. EPA Report 170, EPA-600/4-76-061, 1–21.
King ST (1973) Application of infrared Fourier transform spectroscopy to the analysis of micro samples. J Agric Food Chem 21: 526–530.
Krishman K, Brown RH, Hill SL, Simonoff SC, Olson ML, Kuehi D (1981) Recent developments in GC/FTIR spectroscopy. Am Lab 22: 122–126.
Nakanishi K, Solomon PH (1977) Infrared absorption spectroscopy-practica. 2nd ed. Holden-Day, San Francisco, California.
Rossiter V (1982) Capillary GC/FTIR. Am Lab 23: 71–80.
Shafer KH, Bjorseth A, Tabon J, Jacobsen RJ (1980) Advancing the chromatography of GC/FT-IR to WCOT capillary columns. High Resol Chromatogr Chromatogr Comm 3: 87–88.
Nuclear Magnetic Resonance
Abraham RJ, Loftus P (1978) Proton and carbon-13 NMR spectroscopy. Heyden, London.
Becker ED (1969) High resolution NMR. Academic Press, New York.
Bovey FA (1969) NMR Spectroscopy. Academic Press, New York.
Levy GC, Lichter RL, Nelson GL (1980) Carbon-13 Nuclear Magnetic Resonance for Organic Chemists. 2nd ed. Wiley, New York.
Levy GC, Craile DJ (1981) Recent developments in nuclear magnetic resonance spectroscopy. Science 214: 291–299.
Shoolery JN (1972) A Basic Guide to NMR. Varian Assoc., Palo Alto, California.
Stothers JB (1972) Carbon-13 NMR Spectroscopy. Academic Press, New York.
Microtechniques
Beroza M (1970) Determination of the chemical structure of organic compounds at the microgram level by gas chromatography. Accounts Chem Res 3:33– 49.
Beroza M (1975) Microanalytical methodology relating to the identification of insect sex pheromones and related behavior-control chemicals. J Chromatogr Sci 13: 314–321.
Beroza M, Bierl B (1966) Apparatus for ozonolysis of microgram to milligram amounts of compound. Anal Chem 38: 1976–1977.
Beroza M, Bierl B (1967) Rapid determination of olefin position in organic compounds in microgram range by ozonolysis and gas chromatography. Anal Chem 39: 1131–1135.
Beroza M, Coad RA (1966) Reaction gas chromatography. J Gas Chromatogr 3: 199–216.
Beroza M, Sarmiento R (1966) Apparatus for reaction chromatography. Instantaneous hydrogenation of unsaturated esters, alcohols, ethers, ketones, and other compound types and determination of their separation factors. Anal Chem 38: 1042–1047.
Huwyler S (1973) Ultramikromethoden. Katalytische Hydrierung. Experientia 29: 1310–1311.
Huwyler S (1976) Ultramicromethods. VI. Lithium aluminumhydride reduction of aldehydes and ketones. J Microchem 21: 135–139.
Huwyler S (1977) Ultramicromethods. VII. Vacuum distillation. Improvement of a previously described apparatus. J Microchem 22: 236–237.
Huwyler S (1979) Ultramicromethods. VII. Ozonolysis. J Microchem 24:468– 474.
Tumlinson JH, Heath RR (1976) Structure elucidation of insect pheromones by microanalytical methods. J Chem Ecol 2: 87–99.
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Heath, R.R., Tumlinson, J.H. (1984). Techniques for Purifying, Analyzing, and Identifying Pheromones. In: Hummel, H.E., Miller, T.A. (eds) Techniques in Pheromone Research. Springer Series in Experimental Entomology. Springer, New York, NY. https://doi.org/10.1007/978-1-4612-5220-7_11
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