Insect repellent compounds
View Patent ↗Dihydronepetalactone, a minor natural constituent of the essential oil of catmints ( Nepeta spp.) such as Nepeta 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.
1. A method of repelling an insect or tick from a host for the insect or tick, wherein the host is a human or domesticated animal, comprising applying to a surface of the host the following dihydronepetalactone compound: 1S,9S,5R,6R-5,9-dimethyl-3-oxabicyclo[4.3.0]nonan-2-one
2. The method of claim 1 wherein the host is a host for a biting fly.
3. The method of claim 1 wherein the biting flies comprise one or more members of the group consisting of black flies, green head flies and stable flies.
4. The method of claim 1 wherein the host is a host for a chigger.
5. The method of claim 1 wherein the host is a host for a flea.
6. The method of claim 1 wherein the host is a host for a mosquito.
7. The method of claim 1 which comprises applying the dihydronepetalactone to skin, fur or feathers of the host.
8. The method of claim 1 wherein the host is a host for lice.
9. The method of claim 1 wherein the host is a host for one or more insects in the group consisting of biting flies, chiggers, fleas, mosquitoes and lice.
10. The method of claim 1 wherein the dihydronepetalactone is encapsulated in a protein.
11. The method of claim 1 wherein the dihydronepetalactone is encased with a polymer.
12. The method of claim 1 which comprises applying to the host a composition that comprises the dihydronepetalactone in an amount of at least about 0.001% by weight of the total weight of the composition.
13. The method of claim 1 which comprises applying to the host a composition that comprises the dihydronepetalactone in an amount of from about 0.001% to about 80% by weight of the total weight of the composition.
14. The method of claim 1 which comprises applying to the host a composition that comprises the dihydronepetalactone in an amount of from about 0.01% to about 50% by weight of the total weight of the composition.
15. The method of claim 12 wherein the composition comprises a carrier selected from the group consisting of silicone, petrolatum, lanolin, liquid hydrocarbons, agricultural spray oils, paraffin oil, tall oils, liquid terpene hydrocarbons and terpene alcohols, aliphatic and aromatic alcohols, esters, aldehydes, ketones, mineral oil, higher alcohols, finely divided organic and inorganic solid materials.
16. The method of claim 12 wherein the composition comprises an aerosol composition adapted to disperse the dihydronepetalactone into the atmosphere by means of a compressed gas.
17. The method of claim 12 wherein the composition comprises a polymeric controlled release system.
18. The method of claim 12 wherein the composition is in the form of a cologne, a lotion, a spray, a cream, a gel, an ointment, a bath or shower gel, a foam product, makeup, a deodorant, shampoo, a hair lacquer or rinse or a personal soap.
19. The method of claim 12 wherein the composition comprises one or both of an adjuvant and an insect repellent compound that is not a dihydronepetalactone.
20. The method of claim 19 wherein the adjuvant is selected from the group consisting of thickeners, buffering agents, chelating agents, preservatives, fragrances, antioxidants, gelling agents, stabilizers, surfactants, emollients, coloring agents, aloe vera, waxes, synergists and therapeutically or cosmetically active ingredients.
21. The method of claim 19 wherein the non-dihydronepetalactone insect repellent is selected from the group consisting of: benzil, benzyl benzoate, 2,3,4,5-bis(butyl-2-ene) tetrahydrofurfural, butoxypolypropylene glycol, N-butylacetanilide, normal-butyl-6,6-dimethyl-5,6-dihydro-1,4-pyrone-2-carboxylate, dibutyl adipate, dibutyl phthalate, di-normal-butyl succinate, N,N-diethyl-meta-toluamide, dimethyl carbate (endo,endo)-dimethyl bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate), dimethyl phthalate, 2-ethyl-2-butyl-1,3-propanediol, 2-ethyl-1,3-hexanediol, di-normal-propyl isocinchomeronate, 2-phenylcyclohexanol, p-methane-3,8-diol, 1-piperidinecarboxylic acid 2-(2-hydroxymethyl) 1-methylpropylester and normal-propyl N,N-diethylsuccinamate.
22. The method of claim 19 wherein the non-dihydronepetalactone insect repellent is selected from the group consisting of almond bitter oil, anise oil, basil oil, bay oil, caraway oil, cardamom oil, cedar oil, celery oil, chamomile oil, cinnamon oil, citronella oil, clove oil, coriander oil, cumin oil, dill oil, eucalyptus oil, fennel oil, ginger oil, grapefruit oil, lemon oil, lime oil, mint oil, parsley oil, peppermint oil, pepper oil, rose oil, spearmint oil (menthol), sweet orange oil, thyme oil, turmeric oil, and oil of wintergreen.
23. The method of claim 19 wherein the non-dihydronepetalactone insect repellent is selected from the group consisting of citronellal, methyl salicylate, ethyl salicylate, propyl salicylate, citronellol, safrole, and limonene.
24. The method of claim 12 wherein the composition comprises a carrier selected from the group consisting of oils produced by the distillation of coal and the distillation of petrochemical stocks.
25. The method of claim 12 wherein the composition comprises a carrier selected from the group consisting of synthetic arid natural clay, bentonite, attapulgite, fuller's earth, diatomaceous earth, kaolin, mica, talc, finely divided quartz, silica aerogels, precipitated silicas, fumed silicas, cellulose, sawdust, synthetic organic polymers, waxy solids, gels and lanolin.
26. The method of claim 15 wherein the carrier further comprises an emulsifying agent.
27. The method of claim 1 wherein the host is a human.
28. The method of claim 1 wherein the host is a dog.
29. The method of claim 1 wherein the host is poultry.
30. The method of claim 1 wherein the host is a cow.