Abstract
The flowers of the herbaceous perennial Chrysanthemum cinerariaefolium Vis. (synonym, Pyrethrum cinerariaefolium Trev.), a member of the Compositae family, are valued for their insecticidal properties: the history of their employment has been discussed by Gnadinger (77,78). Commercial supplies were originally obtained from Dalmatia and Japan, but to-day the principal world source is Kenya where a rationally administered industry provides standardised products. Other Compositae flowers have insecticidal activity but of these only Chrysanthemum coccineum Willd. (synonyms, C. carneum Steud and C. roseum Adam) has commercial value, though it is cultivated on a restricted scale. The active insecticidal principles, the Pyrethrins, are contained mostly in the achenes of C. cinerariaefolium (19–21). Harvesting the crop requires much hand labour as maximum yields are obtained by gathering the flower (Fig. I) when four or five rows of disc florets are open. The flowers are artificially dried and baled and are known commercially as “pyrethrum”. As insecticides, the Pyrethrins have the advantage of low mammalian toxicity and so far insects have not easily developed resistance towards them. They are also well known for their rapid “knock-down” or paralytic properties which are valuable in dealing with flying insects.
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References
Acree, F., Jr. and F. B. Laforge: Constituents of Pyrethrum Flowers. X. Identification of the Fatty Acids Combined with Pyrethrolone. J. Organ. Chem. (USA) 2, 308 (1937).
Acree, F., Jr., C. C. Roan and F. H. Babers: The Synthesis and Chromatographic Purification of Radioactive Allethrin. J. econ. Entomol. 47, 1066 (1954).
Allen, C. F. H.: Carbonyl Bridge Compounds and Related Substances. Chem. Rev. 37, 209 (1945).
Barthel, W. F. and H. L. Haller: Purification of Pyrethrum Extract with Nitromethane. U.S. Patent 2372183 (1945).
Barthel, W. F., H. L. Haller and F. B. Laforge: Pyrethrins for Aerosols. Soap 20,(7), 121 (1944).
Barton, D. H. R., O. C. BöCokman and P. de Mayo: Sesquiterpenoids. Part XII. Further Investigations on the Chemistry of Pyrethrosin. J. Chem. Soc. (London) 1960, 2263.
Bavley, A. and E. C. Schreiber: Process for the Manufacture of 2,5-Diketo-nonen-3-ol. U. S. Patent 2768967 (1956).
Beroza, M.: Pyrethrum Synergists in Sesame Oil. Sesamolin, a Potent Synergist. J. Amer. Oil Chem. Soc. 31, 302 (1954).
—: Sesamolin and Related Compounds as Synergists for Pyrethrum. Soap 32,(7), 128 (1956).
Beroza, M. and W. F. Barthel: Chemical Structure and Activity of Pyrethrin and Allethrin Synergists for Control of the Housefly. J. Agric. Food Chem. 5, 855 (1957).
Boon, W. R. and F. Hall: Ethyl Chrysanthemate. Brit. Patent 740014 (1955).
Brown, N. C., D. T. Hollinshead, R. F. Phipers and M. C. Wood: New Isomers of the Pyrethrins Formed by the Action of Heat. Pyrethrum Post 4, No. 2, 13 (1957).
R. F. Phipers and M. C. Wood —: Application of Chromatography to Analysis of Pyrethrins. Soap 33,(9), 87, (10), 91 (1957).
Brown, N. C. and R. F. Phipers: The Analysis of Pyrethrins. Errors Arising During the Examination of Partially Degraded Materials. Pyrethrum Post 3, No. 4, 23 (1955).
Busvine, J. R. and R. Nash: The Potency and Persistence of Some New Synthetic Insecticides. Bull, entom. Res. 44, 371 (1953).
Cahn, R. S., C. K. Ingold and V. Prelog: The Specification of Asymmetric Configuration in Organic Chemistry. Experientia 12, 81 (1956).
Campbell, I. G. M. and S. H. Harper: Experiments on the Synthesis of the Pyrethrins. Part I. Synthesis of Chrysanthemum Monocarboxylic Acid. J. Chem. Soc. (London) 1945, 283.
—: The Chrysanthemumcarboxylic Acids. IV. Optical Resolution of the Chrysanthemic Acids. J. Sci. Food Agric. 3, 189 (1952).
Chandler, S. E.: Botanical Aspects of Pyrethrum. General Considerations; the Seat of the Active Principles. Pyrethrum Post 2, No. 3, 1 (1951).
—: Botanical Aspects of Pyrethrum. II. Further Observations. Pyrethrum Post 3, No. 3, 6 (1954).
—: Botanical Aspects of Pyrethrum. III. The Natural History of the Secretory Organs; the Pyrethrins Content of the Fertile Achenes (“Seed”). Pyrethrum Post 4, No. I, 10 (1956).
Cornelius, J. A.: A Chromatographic Procedure for the Determination of Pyrethrins in Pyrethrum Extracts. Analyst 79, 458 (1954).
Crombie, L. and J. Crossley: Unpublished work.
Crombie, L., A. J. B. Edgar, S. H. Harper, M. W. Lowe and D. Thompson: Experiments on the Synthesis of the Pyrethrins. Part V. Synthesis of Side-chain Isomers and Analogues of Cinerone, Cinerolone, and Cinerin-I. J. Chem. Soc. (London) 1950, 3552.
Crombie, L., M. Elliott and S. H. Harper: Experiments on the Synthesis of the Pyrethrins. Part III. Synthesis of Dihydrocinerin-I and Tetrahydro-pyrethrin-I; a Study of the Action of N-Bromosuccinimide on 3-Methyl-2-n-alkyl (and alkenyl)-cyclopent-2-en-I-ones. J. Chem. Soc. (London) 1950, 971.
Crombie, L., M. Elliott, S. H. Harper and H. W. B. Reed: Total Synthesis of Some Pyrethrins. Nature (London) 162, 222 (1948).
Crombie, L. and S. H. Harper: Synthesis of Cinerone, Cinerolone and Cinerin-I. Nature (London) 164, 534 (1949).
—“Leaf Alcohol” and the Stereochemistry of the cis-and the trans-n-Hex-3-en-I-ols and n-Pent-3-en-I-ols. J. Chem. Soc. (London) 1950, 873.
—Experiments on the Synthesis of the Pyrethrins. Part IV. Synthesis of Cinerone, Cinerolone, and Cinerin-I. J. Chem. Soc. (London) 1950, 1152.
—Experiments on the Synthesis of the Pyrethrins. Part VIII. Stereochemistry of Jasmone and Identity of Dihydropyrethrone. J. Chem. Soc. (London) 1952, 869.
—The Chrysanthemumcarboxylic Acids. Part VI. The Configurations of the Chrysanthemic Acids. J. Chem. Soc. (London) 1954, 470.
—Spectroscopic Assignment of Geometrical Configuration to Rethrins-I. Chem. and Ind. 1958, 1001.
Crombie, L., S. H. Harper and K. Mackenzie: Unpublished work.
Crombie, L., S. H. Harper and F. C. Newman: Experiments on the Synthesis of the Pyrethrins. Part XI. Synthesis of czs-Pyrethrolone and Pyrethrin I: Introduction of the cis-Penta-2,4-dienyl System by Selective Hydrogenation. J. Chem. Soc. (London) 1956, 3963.
Crombie, L., S. H. Harper, F. C. Newman, D. Thompson and R. J. D. Smith: Experiments on the Synthesis of the Pyrethrins. Part X. Intermediates for the Synthesis of cis-Pyrethrolone. J. Chem. Soc. (London) 1956, 126.
Crombie, L., S. H. Harper and K. C. Sleep: Synthesis of the Naturally Derived Geometrical Isomer of Chrysanthemum Dicarboxylic Acid. Chem. and Ind. 1954, 1538.
—Experiments on the Synthesis of the Pyrethrins. Part XIII. Total Synthesis of (±)-cis-and trans-Chrysanthemumdicarboxylic Acid, (±)-cis-and trans-Pyrethric Acid, and Rethrins II. J. Chem. Soc. (London) 1957, 2743.
Crombie, L., S. H. Harper, R. E. Stedman and D. Thompson: Experiments on the Synthesis of the Pyrethrins. Part VI. New Syntheses of the Cinerolones. J. Chem. Soc. (London) 1951, 2445.
Crombie, L., S. H. Harper and D. Thompson: Experiments on the Synthesis of the Pyrethrins. Part VII. Synthesis of traws-Pyrethrone, trans-Pyrethrolone and a Pyrethrin-I. J. Chem. Soc. (London) 1951, 2906.
Crombie, L., S. H. Harper and R. A. Thompson: The Chrysanthemum-carboxylic Acids. III. Lactonisation of the Chrysanthemic Acids. J. Sci. Food Agric. 2, 421 (1951).
Crowley, M. P., H. S. Inglis, M. Snarey and E. M. Thain: Personal communication.
Cupples, H. L.: Infrared Spectra of Cinerolone and Synthetic traws-(2-Butenyl)-4-hydroxy-3-methyl-2-cyclopenten-I-one. J. Amer. Chem. Soc. 72, 4522 (1950).
Dauben, H. J., Jr. and E. Wenkert: Synthesis and Structure of Tetra-hydropyrethrolone. J. Amer. Chem. Soc. 69, 2074 (1947).
de Mayo, P.: The Chemistry of Natural Products, Vol. II. Mono-and Sesquiterpenoids. New York: Interscience Publ. 1959.
Elliott, M.: Unpublished work.
—: The Insecticidal Activity of the Pyrethrins and Related Compounds. Pyrethrum Post 2(3), 18 (1951).
—: Allethrin. J. Sci. Food Agric. 5, 505 (1954).
— The Preparation of cycloPentenones from the Products of Stobbe Condensations with Aliphatic Ketones. J. Chem. Soc. (London) 1956, 2231.
— Isolation and Purification Of (+)-Pyrethrolone From Pyrethrum Extract: Reconstitution of Pyrethrins I and II. Chem. and Ind. 1958, 685.
— Pyrethrolone and Related Compounds. Chem. and Ind. 1960, 1142.
— The Structures of the Enols of Pyrethrolone. Proc. Chem. Soc. (London) 1960, 406.
—: The Pyrethrins and Related Compounds. Part II. Infra-red Spectra of the Pyrethrins and of Other Constituents of Pyrethrum Extract. J. Applied Chem. (London) 11, 19 (1961).
Elliott, M. and P. H. Needham: Unpublished work.
Elliott, M., P. H. Needham and C. Potter: The Insecticidal Activity of Substances Related to the Pyrethrins. I. Toxicities of Two Synthetic Pyrethrin-like Esters Relative to that of the Natural Pyrethrins and the Significance of the Results in the Bioassay of Closely Related Compounds. Ann. appl. Biol. 37, 490 (1950).
Elliott, M., J. S. Olejniczak and J. J. Garner: Laboratory-Scale Molecular Distillation of the Pyrethrins. Pyrethrum Post 5(2), 8 (1959).
Ettlinger, M. G., S. H. Harper and F. Kennedy: The Addition of Ethyl Diazoaeetate to Sorbic Esters: A Correction. J. Chem. Soc. (London) 1957, 922.
Fales, J. H., O. F. Bodenstein and M. Beroza: New Pyrethrum Synergist. Soap 33,(2) 79 (1957).
Farkaš, J., H. Komrsová, J. KrupičKa und J. J. K. Novák: Beziehung zwischen chemischem Bau und Insektizid-Aktivität in der Reihe der Pyrethrum-Verbindungen. IV. Über den Einflu ß der Substituenten in der Scitenkette auf den Verlauf der LaForge-Cyclisierung. Coll. Czech. Chem. Comm. 25, 1824 (1960).
Feinstein, L. and M. Jacobson: Insecticides Occurring in Higher Plants. Fortschr. Chem. organ. Naturstoffe 10, 423 (1953).
Feldman, A.: Stereo Numbers: A Short Designation for Stereoisomers. J. Organ. Chem. (USA) 24, 1556 (1959).
Frank, R. L., R. Armstrong, J. Kwiatek and H. A. Price: The Preparation of Cyclopentenones from Lactones. J. Amer. Chem. Soc. 70, 1379 (1948).
Fredga, A.: Optically Active Forms of Terebic Acid. Svensk Papperstidn. 50, No. 11 B, 91 (1947).
Fredga, A. und E. Leskinen: Konfiguration einiger Terpene. Ark. Kemi, Mineral. Geol. 19 B, No. 1 (1945).
Freeman, S. K.: Infra-red Spectrophotometric Determination of Allethrin. Analyt. Chemistry 27, 1268 (1955).
Freudenberg, K. und G. S. Sidhu: Die absolute Konfiguration des Sesamins und Pinoresinols. Tetrahedron Letters 1960, No. 20, 3.
Fujitani, J.: Chemistry and Pharmacology of Insect Powder. Arch. exp. Pathol. Pharmakol. 61, 47 (1909).
Fukushi, S.: The Components of the Unsaponifiable Matter of the Wax of Chrysanthemum cinerariaefolium. J. Agric. Chem. Soc. Japan 26, 1 (1952).
Gersdorff, W. A.: Toxicity to Houseflies of the Pyrethrins and Cinerins, and Derivatives, in Relation to Chemical Structure. J. econ. Entomol. 40, 878 (1947).
Gersdorff, W. A. and N. Mitlin: A Bioassay of some Stereoisomeric Constituents of Allethrin. J. Washington Acad. Sci. 42, 313 (1952).
—: The Relative Toxicity to House Flies of the Methyl and Ethyl Analogues of Allethrin. J. econ. Entomol. 46, 945 (1953).
Gersdorff, W. A., N. Mitlin and M. Beroza: Comparative Effects of Sesamolin, Sesamin and Sesamol in Pyrethrum and Allethrin Mixtures as House-Fly Sprays. J. econ. Entomol. 47, 839 (1954).
Gersdorff, W. A. and P. G. Piquett: Comparative Effect of Piperetine in Pyrethrum and Allethrin Mixtures as Housefly Sprays. J. econ. Entomol. 50, 164 (1957).
—: Effect of Molecular Configuration on Relative Toxicity to House Flies as Demonstrated with the Four cis-Isomers of Allethrin. J. econ. Entomol. 51, 181 (1958).
Gersdorff, W. A., P. G. Piquett and M. Beroza: Comparative Effects of the Optical Forms of Epiasarinin, Asarinin and Sesamin in Pyrethrum Mists as Housefly Sprays. J. econ. Entomol. 50, 409 (1957).
Gillam, A. E. and T. F. West: Observations on the Absorption Spectra of Terpenoid Compounds. Part IV. Five-Atom-Ring Unsaturated Ketones. J. Chem. Soc. (London) 1942, 486.
—Absorption Spectra and the Structure of Pyrethrins I and II. J. Chem. Soc. (London) 1942, 671.
Gillam, A. E. and T. F. West: Absorption Spectra and the Structure of Pyrethrins I and II. Part II. J. Chem. Soc. (London) 1944, 49.
Gnadinger, C. B.: Pyrethrum Flowers, 2nd Ed. Minneapolis, Minn.: Mc-Laughlin Gormley King Co. 1936.
—: Pyrethrum Flowers. Suppl. To 2Nd Ed. (1936–1945). Minneapolis, Minn.: McLaughlin Gormley King Co. 1945.
Haller, H. L. and F. B. Laforge: Constituents of Pyrethrum Flowers. IV. The Semicarbazones of Pyrethrins I and II and of Pyrethrolone. J. Organ. Chem. (USA) I, 38 (1936).
—: Constituents of Pyrethrum Flowers. VII. The Behavior of the Pyrethrins on Hydrogénation. J. Organ. Chem. (USA) 2, 49 (1937).
—: Constituents of Pyrethrum Flowers. IX. The Optical Rotation of Pyrethrolone and the Partial Synthesis of Pyrethrins. J. Amer. Chem. Soc. 59, 1678 (1937).
—: Constituents of Pyrethrum Flowers. XIV. The Structures of the Enols of Pyrethrolone. J. Organ. Chem. (USA) 3, 543 (1939).
Haller, H. L., F. B. Laforge and W. N. Sullivan: Some Compounds Related to Sesamin: Their Structures and Their Synergistic Effect with Pyrethrum Insecticides. J. Organ. Chem. (USA) 7, 185 (1942).
Harper, S. H.: Experiments on the Synthesis of the Pyrethrins. Part II. The Structure of Cinerone. J. Chem. Soc. (London) 1946, 892.
— A Nomenclature for the Pyrethrins. Chem. and Ind. 1949, 636; Pyrethrum Post 2, (I) 20 (1950).
—: The Chrysanthemumcarboxylic Acids. VII. Catalytic Hydrogenation of the Chrysanthemic Acids. J. Sci. Food Agric. 5, 529 (1954).
Harper, S. H. and M. A. Kazi: Unpublished work.
Harper, S. H. and H. W. B. Reed: The Chrysanthemumcarboxylic Acids. II. Esterification of the Chrysanthemic Acids. J. Sci. Food Agric. 2, 414 (1951).
— Experiments on the Synthesis of the Pyrethrins. Part IX. The Addition of Ethyl Diazoacetate to Sorbic Esters. J. Chem. Soc. (London) 1955 779.
Harper, S. H., H. W. B. Reed and R. A. Thompson: The Chrysanthemumcarboxylic Acids. I. Preparation of the Chrysanthemic Acids. J. Sci. Food Agric. 2, 94 (1951).
Harper, S. H. and K. C. Sleep: The Chrysanthemumcarboxylic Acids. VIII. A Modified Route to the Chrysanthemic Acids. J. Sci. Food Agric. 6, 116 (1955).
Harper, S. H. and R. A. Thompson: The Chrysanthemumcarboxylic Acids. V. Hydration of the Chrysanthemic Acids. J. Sci. Food Agric. 3, 230 (1952).
Harvill, E. K., A. Hartzell and J. M. Arthur: Toxicity of Piperine Solutions to Houseflies. Contrib. Boyce Thompson Inst. 13, 87 (1943).
Haynes, H. L., H. R. Guest and H. A. Stansbury Et Al.: Cyclethrin. Soap 31,(2) 141 (1955).
Hedenburg, O. F. and H. Wachs: Methylenedioxyphenyl Cyclohexenones. J. Amer. Chem. Soc. 70, 2216 (1948).
Henne, A. L. and H. H. Chanan: Conjugated Diolefins by Double Bond Displacement. II. J. Amer. Chem. Soc. 66, 395 (1944).
Hunsdiecker, H.: Über das Verhalten der γ-Diketone. II. Mitt. Der Cyclo-pentenon-Ringschluß der γ-Diketone vom Typus CH3 · CO·CH2 · CH2 · CO · · CH2 · R. Ber. dtsch. chem. Ges. 75, 455 (1942).
Hunsdiecker, H. und E. Wirth: Über das Verhalten der γ-Diketone. III. Mitt. Die Synthese des Jasmons. Ber. dtsch. chem. Ges. 75, 460 (1942).
Incho, H. H. and H. Greenberg: Synergistic Effect of Piperonyl Butoxide with the Active Principles of Pyrethrum and with Allethrolone Esters of Chrysanthemum Acids. J. econ. Entomol. 45, 794 (1952).
Inoue, Y.: Synthesis and Stereochemistry of Chrysanthemum Dicarboxylic Acid. Bull. Inst. Chem. Res. Kyoto Univ. 35, 49 (1957).
Inoue, Y. and M. Ohno: Resolution of (±)-trans-3-(trans-2-carboxypropenyl)-2,2-Dimethylcyclopropane-I-carboxylic Acid. Bull. Inst. Chem. Res., Kyoto Univ. 34, 90 (1956).
—: Absolute Configuration of Natural Pyrethrins. Kagaku (Tokyo) 28, 636 (1958).
Inoue, Y., T. Shinohara and M. Ohno: An Approach to the Synthesis of Pyrethric Acid. Botyu Kagaku 19, 35 (1954).
Inoue, Y., Y. Sugita and M. Ohno: Synthesis of Pyrethroids. IX. Assignment of Geometrical Configuration to αδ-Dimethylsorbic Acid. Bull. Agric. Chem. Soc. Japan 21, 5 (1957).
M. Ohno —: Synthesis of Pyrethroids. XI. Another Piece of Evidence for the trans-Configuration of αδ-Dimethylsorbic Acid. Bull. Agric. Chem. Soc. Japan 21, 222 (1957).
M. Ohno —: A Novel Route of Synthesis to Chrysanthemumdicarboxylic Acid. Bull. Agric. Chem. Soc. Japan 22, 269 (1958).
Inoue, Y., Y. Takeshita and M. Ohno: Studies on Synthetic Pyrethroids. V. Synthesis of Geometrical Isomers of Chrysanthemumdicarboxylic Acid. Botyu-Kagaku 20, 102 (1955).
M. Ohno —: Geometrical Isomers of Chrysanthemum Dicarboxylic Acid. Bull. Inst. Chem. Res., Kyoto Univ. 33, 73 (1955).
Jackman, L. M. and R. H. Wiley: Studies in Nuclear Magnetic Resonance. Part III. Assignment of Configurations of aαβ-Unsaturated Esters and the Isolation of Pure trans-β-Methylglutaconic Acid. J. Chem. Soc. (London) 1960, 2886.
Julia, M., S. Julia Et C. Jeanmart: Synthèses de l’acide trans-dihyaxo-chrysanthémique. C. R. hebd. Séances Acad. Sci. 250, 4003 (1960).
—: Synthèses de la pyrocine, de l’acide trans-(±)-chrysanthémique et de quelques acides cyclopropaniques apparantés. C. R. hebd. Séances Acad. Sci. 251, 249 (1960).
Kageyama, I.: Extraction of Active Principles from Pyrethrum, Derris, Tobacco etc. Japanese Patent 3649 (1952) [Chem. Abstr. 47, 8328 (1953)].
Katsuda, Y., T. Chikamoto and Y. Inoue: The Absolute Configuration of Naturally Derived Pyrethrolone. Bull. Agric. Chem. Soc. Japan 22, 427 (1958); Relationship between Stereoisomers and Biological Activity of Pyrethroids. Part V. The Absolute Configuration of (+)-Pyrethrolone and (+)-Cinerolone. Bull. Agric. Chem. Soc. Japan 23, 174 (1959).
Katsuda, Y. and T. Chikamoto: Studies on the Degradation of Pyrethrins. IV. Botyu-Kagaku 23, 60 (1958).
Laforge, F. B. and F. Acree, Jr.: Constituents of Pyrethrum Flowers. XV. Presence of the Cumulated System in the Pyrethrolone Side-Chain. J. Organ. Chem. (USA) 7, 416 (1942).
Laforge, F. B. and W. F. Barthel: Constituents of Pyrethrum Flowers. XVI. Heterogeneous Nature of Pyrethrolone. J. Organ. Chem. (USA) 9, 242 (1944).
—: Constituents of Pyrethrum Flowers. XVII. The Isolation of Five Pyrethrolone Semicarbazones. J. Organ. Chem. (USA) 10, 106 (1945).
Laforge, F. B. and W. F. Barthel: Constituents of Pyrethrum Flowers. XVIII. The Structure and Isomerism of Pyrethrolone and Cinerolone. J. Organ. Chem. (USA) 10, 114 (1945).
—: Constituents of Pyrethrum Flowers. XIX. The Structure of Cinerolone. J. Organ. Chem. (USA) 10, 222 (1945).
—: Constituents of Pyrethrum Flowers. XX. The Partial Synthesis of Pyrethrins and Cinerins and their Relative Toxicities. J. Organ Chem. (USA) 12, 199 (1947).
Laforge, F. B., W. A. Gersdorff, N. Green and M. S. Schechter: Allethrin-Type Esters of Cyclopropanecarboxylic Acids and their Relative Toxicities to House Flies. J. Organ. Chem. (USA) 17, 381 (1952).
Laforge, F. B. and N. Green: Constituents of Pyrethrum Flowers. XXV. The Synthesis of d-Cinerolone, Cinerin I, and its Optical Isomers. J. Organ. Chem. (USA) 17, 1635 (1952).
Laforge, F. B., N. Green and M. S. Schechter: Dimerized Cyclopenta-dienones from Esters of Allethrolone. J. Amer. Chem. Soc. 74, 5392 (1952).
M. S. Schechter —: Allethrin. Resolution of dl-Allethrolone and Synthesis of the Four Optical Isomers of trans-Allethrin. J. Organ. Chem. (USA) 19, 457 (1954).
M. S. Schechter —: Allethrin. Synthesis of Four Isomers of cis-Allethrin. J. Organ. Chem. (USA) 21, 455 (1956).
Laforge, F. B. and H. L. Haller: Constituents of Pyrethrum Flowers. V. Concerning the Structure of Pyrethrolone. J. Amer. Chem. Soc. 58, 1061 (1936).
—: Constituents of Pyrethrum Flowers. VI. The Structure of Pyrethrolone. J. Amer. Chem. Soc. 58, 1777 (1936).
—: Constituents of Pyrethrum Flowers. VIII. The Presence of a New Ester of Pyrethrolone. J. Organ. Chem. (USA) 2, 56 (1937).
—: Constituents of Pyrethrum Flowers. XII. The Nature of the Side-Chain of Pyrethrolone. J. Organ. Chem. (USA) 2, 546 (1938).
Laforge, F. B. and S. B. Soloway: Constituents of Pyrethrum Flowers. XXI. Revision of the Structure of Dihydrocinerolone. J. Amer. Chem. Soc. 69, 2932 (1947).
Lord, K. A., J. Ward, J. A. Cornelius and M. W. Jarvis: Chromatographic Separation of the Pyrethrins. J. Sci. Food Agric. 3, 419 (1952).
Matsubara, H.: A New Synergist for Pyrethrins (Hinokinin). Science (Japan) 20, 183 (1950).
—: Hibalactone (Savinin) as a Synergist with Pyrethrins and Allethrin. Bull. Agric. Chem. Soc. Japan 21, 132 (1957).
Matsui, M.: Pyrocin (a New Insecticide). Botyu-Kagaku 15, 1 (1950).
—: Synthetic Insecticide. Japanese Patent 5626 (1955) [Chem. Abstr. 52, 1218 (1958)].
Matsui, M., S. Kitamura, T. Kato and S. Sugihara: Synthesis of Cyclo-pentenolones of the Cinerolone Type. J. Chem. Soc. Japan 71, 235 (1950).
Matsui, M., F. B. Laforge, N. Green and M. S. Schechter: Furethrin. J. Amer. Chem. Soc. 74, 2181 (1952).
Matsui, M., M. Miyano, K. Yamashita, H. Kubo and K. Tomita: Syntheses of Pyrethridic (Chrysanthemumdicarboxylic) Acid. Bull. Agric. Chem. Soc. Japan 21, 22 (1957).
Matsui, M., T. Ohno, S. Kitamura and M. Tayao: The Lactones Derived from Chrysanthemic Acids. Bull. Chem. Soc. Japan 25, 210 (1952).
Matsumoto, T. and A. Suzuki: Reaction of Isopropyl Zinc Iodide with Terebic Acid Chloride. A Suggested New Mode of Action of the Blaise Reagent. J. Organ. Chem, (USA) 25, 1666 (1960).
Merritt, R. P. and T. F. West: Notes on the Oil Distilled from Pyrethrum Flowers. J. Soc. Chem. and Ind. 57, 321 (1938).
Metcalf, R. L.: Methods of Topical Application and Injection. In: H. H. Shepard, Methods of Testing Chemicals on Insects, Vol. I, p. 92. Minneapolis, Minn.: Burgess Publ. Co. 1958.
—: Organic Insecticides. Their Chemistry and Mode Of Action. New York and London: Interscience Publ. 1955.
Mitchell, W.: “Bucarpolate,” Pyrethrum Synergist. Pyrethrum Post 5, No. I, 19 (1959).
Moore, B. P. and P. S. Hewlett: Insecticidal Synergism with the Pyrethrins: Studies on the Relationship between Chemical Structure and Synergistic Activity in 3,4-Methylenedioxyphenyl Compounds. J. Sci. Food Agric. 9, 666 (1958).
Negherbon, W. O.: Handbook of Toxicology. Vol. III, Insecticides. A Compendium. Philadelphia and London: W. B. Saunders Co. 1959.
Newman, M. S. and W. T. Booth, Jr.: The Preparation of Ketones from Grignard Reagents. J. Amer. Chem. Soc. 67, 154 (1945).
Pellegrini, J. P., A. C. Miller and R. V. Sharpless: Biosynthesis of Radioactive Pyrethrins using 14CO2. J. econ. Entomol. 45, 532 (1952).
Phipers, R. F.: Pyrethrins and Allied Compounds. In: K. Paech and M. V. Tracey, Modern Methods of Plant Analysis, Vol. III, p. 43. Berlin: Springer-Verlag. 1955.
—: The Analysis of Pyrethrins. A Review of Recent Publications. Pyrethrum Post 4(3), 3 (1958).
Potter, C. and M. J. Way: Precision Spraying. In: H. H. Shepard, Methods of Testing Chemicals on Insects, Vol. I, p. 154. Minneapolis, Minn.: Burgess Publ. Co. 1958.
Quayle, J. R.: Paper Chromatography of Pyrethrins and their Derivatives. Nature (London) 178, 375 (1956).
Rai, C. and S. Dev: Organic, Reactions with Polyphosphoric Acid. IV. Intramolecular Acylation with Lactones: cycloPentenones from γ-Lactones. J. Indian Chem. Soc. 34, 178 (1957).
Roark, R. C.: A Digest of Information on Allethrin. U. S. Dept. Agric., Bur. Entomology and Plant Quarantine, Agric. Res. Admin., E 846, Sept. 1952.
Roark, R. C. and R. H. Nelson: A Second Digest of Information on Allethrin and Related Compounds. U. S. Dept. Agric, Agric. Res. Serv. ARS-33-12 (1955).
Ruzicka, L.: History of the Isoprene Rule. Proc. Chem. Soc. (London) 1959, 341.
Ruzicka, L. und M. Pfeiffer: Über Jasminriechstoffe. I. Die Konstitution des Jasmons. Helv. Chim. Acta 16, 1208 (1933).
Sanders, H. J. and A. W. Taff: Allethrin. Ind. Eng. Chem. 46, 414 (1954).
Sawicki, R. M.: Insecticidal Activity of the Four Constituents of Pyrethrum. Rothamsted Exp. Stat. Report for 1960 (in press).
—: A Technique for the Knockdown Assessment of Topically Treated Normally Active Houseflies. Bull. entom. Res. 51, 715 (1961).
Sawicki, R. M., M. Elliott, J. C. Gower, M. Snarey and E. M. Thain: Insecticidal Activity of Pyrethrum Extract and its Active Constituents against Houseflies. I. Preparation and Relative Toxicity of the Pure Constituents; Statistical Analysis of Mixtures of these Compounds. J. Sci. Food Agric. (1961) (in press).
Sawicki, R. M. and E. M. Thain: The Chemical and Biological Examination of Commercial Pyrethrum Extracts for Insecticidal Constituents. J. Sci. Food Agric. 12, 137 (1961).
Schechter, M. S., N. Green and F. B. Laforge: Constituents of Pyrethrum Flowers. XXIII. Cinerolone and the Synthesis of Related Cyclopentenolones. J. Amer. Chem. Soc. 71, 3165 (1949).
Schechter, M. S., N. Green and F. B. Laforge: Constituents of Pyrethrum Flowers. XXIV. Synthetic dl-cis-Cinerolone and Other Cyclopentenolones. J. Amer. Chem. Soc. 74, 4902 (1952).
Schechter, M. S., F. B. Laforge, A. Zimmerli and J. M. Thomas: Crystalline Allethrin Isomer. J. Amer. Chem. Soc. 73, 3541 (1951).
Schmidt, H.: Zur Kenntnis des Pfefferminzöls. Vorkommen von Jasmon im ätherischen Öl von Mentha piperita L. Chem. Ber. 80, 538 (1947).
Simonsen, J. L. and L. N. Owen: The Terpenes, Vol. I. Cambridge: Univ. Press. 1947.
“Socophar”: Extraction of Pyrethrin with Isopropyl Ether. Belgian Patent 509803 (1952) [Chem. Abstr. 52, 6708 (1958)].
Soloway, S. B. and F. B. Laforge: The Synthesis of Dihydrocinerolone. J. Amer. Chem. Soc. 69, 979 (1947).
Spickett, R. G. W.: A Method for the Separation of the Constituents of Pyrethrum Extract. Chem. and Ind. 1957, 561.
Stansbury, H. A., Jr. and H. R. Guest: Derivatives of Chrysanthemum Monocarboxylic Acid. British Patent 744268 (1956).
— [A] Substituted cyclo-Pentenones. [B] An Ester of Chrysanthemum-monocarboxylic Acid and Insecticidal Constituents Therefrom. British Patent 790841 (1958).
Staudinger, H., O. Muntwyler, L. Ruzicka und S. Scibt: Insektentötende Stoffe. VII. Synthesen der Chrysanthemumsäure und anderer Trimethylen-carbonsäuren mit ungesättigter Scitenkette. Helv. Chim. Acta 7, 390 (1924).
Staudinger, H. und L. Ruzicka: Insektentötende Stoffe. I. Über Isolierung und Konstitution des wirksamen Teiles des dalmatinischen Insektenpulvers. Helv. Chim. Acta 7, 177 (1924).
—: Insektentötende Stoffe. IL Zur Konstitution der Chrysanthemummonocarbonsäure und-dicarbonsäure. Helv. Chim. Acta 7, 201 (1924).
—: Insektentötende Stoffe. III. Konstitution des Pyrethrolons. Helv. Chim. Acta 7, 212 (1924).
—: Insektentötende Stoffe. IV. Konstitution des Tetrahydropyrethrons. Helv. Chim. Acta 7, 236 (1924).
—: Insektentötende Stoffe. V. Synthese des Tetrahydropyrethrons, des Reduktionsproduktes des Pyrethrolons. Helv. Chim. Acta 7, 245 (1924).
—: Insektentötende Stoffe. X. Über die Synthese von Pyrethrinen. Helv. Chim. Acta 7, 448 (1924).
Stephenson, H.: The Separation and Estimation of the Four Insecticidal Constituents of Chrysanthemum cinerariaefolium by Elution Chromatography on a Column of Adsorptive Charcoal. Pyrethrum Post 5, No. 4, 22 (1960).
Subbaratnam, A. V. and S. Siddiqui: The Irritant Factor of Pyrethrum Flowers. J. Sci. Industr. Res. (India) 15 B, 243 (1956).
Synerholm, M. E., A. Hartzell and J. M. Arthur: Derivatives of Piperic Acid and their Toxicities towards Houseflies. Contrib. Boyce Thompson Inst. 13, 433 (1945).
Takei, S., T. Sugita und Y. Inouye: Eine neue Synthese der Chrysanthemum-dicarbonsäure. Liebigs Ann. Chem. 618, 105 (1958).
Treff, W. und H. Werner: Über die Synthese des Jasmons. Ber. dtsch. chem. Ges. 68, 640 (1935).
Wachs, H.: Synergistic Insecticides. Science (Washington) 105, 530 (1947).
Wanless, G. G., W. H. King and J. J. Ritter: Hydrocarbons in Pyrethrum Cuticle Wax. Biochemic. J. 59, 684 (1955).
Ward, J.: Separation of the Pyrethrins by Displacement Chromatography. Chem. and Ind. 1953, 586.
Weed, A.: New Insecticide Compound. Soap 14, No. 6, 133 (1938).
West, T. F.: The Structure of Pyrethrolone and Related Compounds. Part II. J. Chem. Soc. (London) 1944, 239.
—The Structure of Pyrethrolone and Related Compounds. Part IV. J. Chem. Soc. (London) 1945, 412.
—The Structure of Pyrethrolone and Related Compounds. Part V. J. Chem. Soc. (London) 1946, 463.
Winteringham, F. P. W., A. Harrison and P. M. Bridges: Absorption and Metabolism of 14C-Pyrethroids by the Adult Housefly, Musca domestica, in vivo. Biochemie. J. 61, 359 (1955).
Woods, G. F. and H. Sanders: Studies in Pyrane Chemistry. J. Amer. Chem. Soc. 68, 2483 (1946).
Yamamoto, R.: The Insecticidal Principle in Chrysanthemum cinerariaefolium. I. J. Tokyo Chem. Soc. 40, 126 (1919).
—: Studies on the Insecticidal Principle in Chrysanthemum cinerariaefolium. Parts II and III. On the Constitution of Pyrethronic Acid. J. Chem. Soc. Japan 44, 311 (1923).
Yamamoto, R. and M. Sumi: Studies on the Insecticidal Principle in Chrysanthemum cinerariaefolium. J. Chem. Soc. Japan 44, 1080 (1923).
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Crombie, L., Elliott, M. (1961). Chemistry of the Natural Pyrethrins. In: Zechmeister, L. (eds) Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products / Progrès dans la Chimie des Substances Organiques Naturelles. Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products / Progrès dans la Chimie des Substances Organiques Naturelles, vol 19. Springer, Vienna. https://doi.org/10.1007/978-3-7091-7156-1_3
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