Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2006-06-26
2009-06-16
Seaman, D. Margaret (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
07547793
ABSTRACT:
Dihydronepetalactone, a minor natural constituent of the essential oil of catmints (Nepetaspp.) such asNepeta cataria, has been identified as an effective insect repellent compound. Synthesis of dihydronepetalactone may be achieved by hydrogenation of nepetalactone, the major constituent of catmint essential oils. This compound, which also has fragrance properties, may be used commercially for its insect repellent properties, and methods for making an composition thereof are disclosed.
REFERENCES:
patent: 4416881 (1983-11-01), McGovern et al.
patent: 4469613 (1984-09-01), Munteanu et al.
patent: 4496467 (1985-01-01), Munteanu et al.
patent: 4548764 (1985-10-01), Munteanu et al.
patent: 4663346 (1987-05-01), Coulston et al.
patent: 4869896 (1989-09-01), Coulston et al.
patent: 5753686 (1998-05-01), Marin et al.
patent: 6462015 (2002-10-01), Weiss et al.
patent: 6524605 (2003-02-01), Coats et al.
patent: 7067677 (2006-06-01), Manzer
patent: 7067678 (2006-06-01), Scialdone
patent: 7232844 (2007-06-01), Hallahan
patent: 2003/0073748 (2003-04-01), Henderson et al.
patent: 2003/0191047 (2003-10-01), Hallan
patent: 2004/0024054 (2004-02-01), Haenke
patent: 0 167 265 (1986-01-01), None
patent: 0 450 087 (1991-04-01), None
patent: 0 450 087 (1991-10-01), None
patent: WO 03/079786 (2003-03-01), None
patent: WO 03/084946 (2003-04-01), None
patent: WO 03/086069 (2003-10-01), None
U.S. Appl. No. 10/405,444, filed Apr. 5, 2003, Leo Ernest Manzer.
C. E. Schreck et. al., Activity of Repellents Applied to Skin for Protection Against Amblyomma Americanum and Ixodes Scapularis Ticks (Acari: Ixodidae), Journal of the American Mosquito Association, 1995, vol. 11:136-140.
R. K. M. Hay et. al., Botany Volatile Oil Crops, Their Biology and Production, 1993, pp. 5-22.
L. J. Clark et. al., Analysis of Monoterpenoids in Glandular Trichomes of the Calmint Nepeta Racemosa. The Plant Journal, 1997, vol. 11:1387-1393.
G. Briassoulis et. al., Toxic Encephalopathy Associated With Use of Deet Insect Repellents: A Case Analysis of its Toxicity in Children, Human & Experimental Toxicology, 2001, vol. 20:8-14.
Chris Peterson et. al., Insect Repellents—Past, Present and Future, Pesticide Outlook, Aug. 2001.
C. Peterson, Abstracts of Paper American Chemical Society, 2001, vol. 222:1-2.
T. Eisner, Science, 1965, vol. 148:966-968.
T. Eisner, Science, 1964, vol. 146:1318-1320.
T. Hollon, For Tomorrow's Infantry:SS-220, A Gunsight Friendly Insect Repellent, The Scientist, 2003, pp. 25-26.
H. Inouye, Iridoids, Methods in Plant Biochemistry, 1991, vol. 7:99-143.
New Scientist, The Sweet Smell of Death, 1996, pp. 28-31.
Pesticide Outlook, Pesticides Based on Plant Essential Oils, 1999, pp. 68-72.
Lena B. Brattsten, Cytochrome P-450 Involement in the Interactions Between Plant Terpenes and Insect Herbivores, 1983, pp. 173-195.
Abstract of Braveman, Y. Mosquito Repellent Attracts Culicoides Imicola, (Diptera: Ceratopogonidae), Journal of Medical Entomology, 1999, vol. 36:113-115.
Ramanathan Natarajan et. al., Chirality Index, Molecular Overlay and Biological Activity of Diastereoisomeric Mosquito Repellents, Pest Management Science, 2005, vol. 61:1193-1201.
Arthur O. Tucker et. al., Catnip and the Catnip Response, Economic Botany, 1988, vol. 42:214-231.
Jefson et. al., Chemical Defense of a Rove Bettle, Journal of Chemical Ecology, 1983, vol. 9:150-180.
G.W.K. Cavill et. al., Defensive and Other Secretions of the Australlian Cocktail Ant, Iridomyrmex Nitidiceps, Tetrahedron, 1982, vol. 38:1931-1938.
G.W.K. Cavill et. al., Insect Venoms, Attractants, and Repellents—VIII, Isohihydronepetalactone, J. Insect Physiol., 1967, vol. 13:131-135.
Abstract of Krell, Frank-Thorsten et. al., Dung Beetles Attracted by a Commerical Insect Repellent, Entomologists Monthly Magazine, 2003, vol. 139:1667-1669.
Uyehara et. al., Cyclisation of A,B,X,U-Unsaturated Dioic Acids Esters Via Tandem Conjugate Additions by Using Lithium-Benzyltrimethylsilylamide (LSA) as a Nitrogen Nucleophile and its (+) Isodihydronepetalactone, J. Chem. Soc., Chem. Commum., 1989, pp. 113-114.
Lee et. al., Stereoselective Favorskii Rearrangement of Carvone Chlopohydrin:Expedient Synthesis of (+) Dihydronepetalactone and (+) Iridomyrmecin, J. Chem. Soc., Chem. Commun., 1994, pp. 479-481.
Tanimori et. al., Total Synthesis of (+) Dihydronepetalactone, Agric. Biol. Chem., 1991, vol. 55:1181-11832.
C.J. Peterson et. al., Catnip Essential Oil as a Barrier to Subterranean Termites (Isoptera: Rhinotermitidae) in the Laboratory, Household and Structural Insects, J. Econ. Entomol., 1998, vol. 4:1275-1282.
International Search Report dated Jul. 11, 2003.
Abelman et. al., Alicyclic Claisen Rearrangement, A General Carbocycle Synthesis Based on Four-Atom-Ring Contractions of Lactones, J. Am. Chem. Soc., 1982, vol. 104:4030-4032.
Fleming et. al., Stereospecific Allylisilane Reactions: A Total Synthesis of Dihydronepetalactone, Tetrahedron Letters, 1984, vol. 25:5103-5104.
Fleming et. al., Sterocontrol in Organic Synthesis Using Silicon-Containing Compounds, A Synthesis of (+) Dihydronepetalactone Using the SE2 Reaction of an Allysilane, J. Chem. Soc., Perkin Trans, 1998, vol. 1:2645-2649.
Nagata et. al., Concurrent Resolution and Oxidation of an Allylic Acetate and its Utilization in the Diastereocontrolled Synthesis of Some Cyclopentanoid Monterpenes, Tetrahedron Letters, 1999, vol. 40:6617-6620.
Nangia et. al., Intramolecular Horner-Wadsworth-Emmons Reaction in Base Sensitive Substrates: Enantiospecific Synthesis of Iridold Monoterpene Lactones, Tetrahedron Letters, 1994, vol. 35:3755-3758.
Uyehara et. al., New Type of Cyclization of a B,X Unsaturated Dioic Acid Esters Through Tandem Conjugate Additions by Using Lithium N-Benzyl-N (Trimethylsilyl) Amide as a Nitrogen Nucleophile, J. Org. Chem., 1992, vol. 57:3139-3145.
Wolinsky et. al., Syntheses of the Dihydronepetalactones, J. Org. Chem., 1972, vol. 37:3376-3378.
Wolinsky et. al., The Synthesis of (+) Matatabiether and Related Methylcyclopentane Monoterpenes, Tetrahedron, 1969, vol. 25:3767-3774.
Barasa et. al., Repellent Activities of Stereoisomers of P-Menthane 3,8 Diols Against Anopheles Gambiae (Diptera: Culicidae), J. Med. Entomol., 2002, vol. 39:736-741.
Barnard et. al., Global Collaboration for Development of Pesticides for Public Healthy, (GCDPP) Wolrd Health Organization, pp. 1-49, 2000.
Bergmann et. al., Study of Synthetic Compounds as Repellents Against the Mosquitoes Culex Pipiens Molestus and Aedes Aegypti, Israel Journal of Entomollgy, 1976, vol. XI, pp. 15-61.
Dawson et. al., The Aphid Sex Pheromone, Pure & Appl. Chem., 1989, vol. 61:555-558.
R. Lilley et. al., The Aphid Sex Pheromone: A Novel Host Location Cue for the Parasitoid Praon Volucre, Brighton Crop Protection Conference—Pests and Disease, 1994, pp. 1157-1162.
W.A. Skinner et. al., The Design of Insect Repellents, Drug Design, 1980, vol. X,:278-305.
Regnier et. al., Studies on the Composition of the Essential Oils of Three Nepeta Species, Phytochemistry, 1967, vol. 6:1281-1289.
Depooter et. al., The Essential Oils Five Nepeta Species. A Preliminary Evaluation of Their Use in Chemotaxonomy by Cluster Analysis, Flavour and Fragrance Journal, 1988, vol. 3:155-159.
Handjieva et. al., Constituents of Essential Oils From Nepeta Cataria L., N. Grandiflora M.B. and N. Nuda L., J. Essential Oil Res., 1996, vol. 8:639-643.
Fradin et. al., Comparative Efficacy of Insect Repellents Against Mosquito Bites, New England Journal of Medicine, 2002, vol. 347:13-18.
H.S. Fogler, Elementary Chemical Reaction Engineering, Prentice-Hall (Book Not Included), 1996.
Augustine, Heterogeneous Catalysis for the Synthetic Chemist, 1996, Marcel Decker, 1996, (Book Not Included.
Hallahan David L.
Manzer Leo Ernest
Chandrakumar Nizal S
E.I. du Pont de Nemours and Company
Seaman D. Margaret
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