US3148111A - Method of repelling insects employing - Google Patents
Method of repelling insects employing Download PDFInfo
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- US3148111A US3148111A US3148111DA US3148111A US 3148111 A US3148111 A US 3148111A US 3148111D A US3148111D A US 3148111DA US 3148111 A US3148111 A US 3148111A
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- insects
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- 241000238631 Hexapoda Species 0.000 title claims description 38
- 230000001846 repelling Effects 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims description 14
- 241001465754 Metazoa Species 0.000 claims description 8
- 239000000203 mixture Substances 0.000 description 48
- 239000004094 surface-active agent Substances 0.000 description 26
- -1 alkyl o-nitrophenyl sulfides Chemical class 0.000 description 24
- 239000000077 insect repellent Substances 0.000 description 20
- 239000003085 diluting agent Substances 0.000 description 18
- LYERWKWSYZQUDA-UHFFFAOYSA-N 1-methylsulfanyl-2-nitrobenzene Chemical compound CSC1=CC=CC=C1[N+]([O-])=O LYERWKWSYZQUDA-UHFFFAOYSA-N 0.000 description 12
- 239000005871 repellent Substances 0.000 description 12
- 230000002940 repellent Effects 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- JARZCLAZRVPFMW-UHFFFAOYSA-N 1-ethylsulfanyl-2-nitrobenzene Chemical class CCSC1=CC=CC=C1[N+]([O-])=O JARZCLAZRVPFMW-UHFFFAOYSA-N 0.000 description 6
- 125000000129 anionic group Chemical group 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 241000283690 Bos taurus Species 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 229940045998 Sodium Isethionate Drugs 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000000428 dust Substances 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000011094 fiberboard Substances 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000003350 kerosene Substances 0.000 description 4
- 229920005610 lignin Polymers 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 235000012222 talc Nutrition 0.000 description 4
- 150000003568 thioethers Chemical class 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- QUOZWMJFTQUXON-UXXRCYHCSA-N 1-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethanone Chemical class COC1=CC(C(C)=O)=CC=C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 QUOZWMJFTQUXON-UXXRCYHCSA-N 0.000 description 2
- KWXICGTUELOLSQ-UHFFFAOYSA-N 4-Dodecylbenzenesulfonic Acid Chemical compound CCCCCCCCCCCCC1=CC=C(S(O)(=O)=O)C=C1 KWXICGTUELOLSQ-UHFFFAOYSA-N 0.000 description 2
- 240000005020 Acaciella glauca Species 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241000396431 Anthrenus scrophulariae Species 0.000 description 2
- 241001289510 Attagenus unicolor Species 0.000 description 2
- 241000238657 Blattella germanica Species 0.000 description 2
- 241001674044 Blattodea Species 0.000 description 2
- JHLNERQLKQQLRZ-UHFFFAOYSA-N Calcium silicate Chemical compound [Ca+2].[Ca+2].[O-][Si]([O-])([O-])[O-] JHLNERQLKQQLRZ-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N Cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- MMOXZBCLCQITDF-UHFFFAOYSA-N DEET Chemical compound CCN(CC)C(=O)C1=CC=CC(C)=C1 MMOXZBCLCQITDF-UHFFFAOYSA-N 0.000 description 2
- YUXIBTJKHLUKBD-UHFFFAOYSA-N Dibutyl succinate Chemical compound CCCCOC(=O)CCC(=O)OCCCC YUXIBTJKHLUKBD-UHFFFAOYSA-N 0.000 description 2
- APSBXTVYXVQYAB-UHFFFAOYSA-M Dioctyl sodium sulfosuccinate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 2
- KWKXNDCHNDYVRT-UHFFFAOYSA-N Dodecylbenzene Chemical class CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 241000462639 Epilachna varivestis Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 240000007842 Glycine max Species 0.000 description 2
- 240000007049 Juglans regia Species 0.000 description 2
- 235000009496 Juglans regia Nutrition 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N Nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Natural products CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 241000231739 Rutilus rutilus Species 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 235000015450 Tilia cordata Nutrition 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H Tricalcium phosphate Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- 240000008529 Triticum aestivum Species 0.000 description 2
- 210000002268 Wool Anatomy 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 229960000892 attapulgite Drugs 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- 239000000378 calcium silicate Substances 0.000 description 2
- 229910052918 calcium silicate Inorganic materials 0.000 description 2
- 125000004432 carbon atoms Chemical group C* 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 2
- JMGZBMRVDHKMKB-UHFFFAOYSA-L disodium;2-sulfobutanedioate Chemical compound [Na+].[Na+].OS(=O)(=O)C(C([O-])=O)CC([O-])=O JMGZBMRVDHKMKB-UHFFFAOYSA-L 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000002194 fatty esters Chemical class 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 239000005022 packaging material Substances 0.000 description 2
- 229910052625 palygorskite Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920000056 polyoxyethylene ether Polymers 0.000 description 2
- 229910052903 pyrophyllite Inorganic materials 0.000 description 2
- 235000003499 redwood Nutrition 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 150000003385 sodium Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- JMHRGKDWGWORNU-UHFFFAOYSA-M sodium;2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetate Chemical compound [Na+].CC1=C(CC([O-])=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 JMHRGKDWGWORNU-UHFFFAOYSA-M 0.000 description 2
- IZWPGJFSBABFGL-GMFCBQQYSA-M sodium;2-[methyl-[(Z)-octadec-9-enoyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS([O-])(=O)=O IZWPGJFSBABFGL-GMFCBQQYSA-M 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 235000001508 sulfur Nutrition 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 235000020234 walnut Nutrition 0.000 description 2
- 239000003799 water insoluble solvent Substances 0.000 description 2
- 235000021307 wheat Nutrition 0.000 description 2
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/18—Nitro compounds
- A01N33/20—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group
- A01N33/22—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group having at least one oxygen or sulfur atom and at least one nitro group directly attached to the same aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P17/00—Pest repellants
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01M—CATCHING, TRAPPING OR SCARING OF ANIMALS; APPARATUS FOR THE DESTRUCTION OF NOXIOUS ANIMALS OR NOXIOUS PLANTS
- A01M29/00—Scaring or repelling devices, e.g. bird-scaring apparatus
- A01M29/12—Scaring or repelling devices, e.g. bird-scaring apparatus using odoriferous substances, e.g. aromas, pheromones or chemical agents
Definitions
- the active compounds of this invention have the structural formula:
- R is methyl or ethyl
- the alkyl o-nitrophenyl sulfides used in this invention are excellent insect repellents. Insects repelled include such insects as German cockroach and other roach species, confused fiour beetle, black carpet beetle, house fly and Mexican bean beetle.
- the compounds of this invention when used in compositions containing liquid diluents or solid particulate diluents, protect treated surfaces such as industrial equipment and backs of cattle from being attacked by the described insects.
- Composition-Insect repellent compositions of this invention will ordinarily comprise at least one compound of formula 1 with one or more surfactants, or with a finely divided solid diluent or a liquid diluent.
- the surface-active agents used in this invention to assist dispersion of the composition can be a dispersant, wetting agent or emulsifying agent.
- the surface-active agent or surfactant can include such anionic, cationic and non-ionic agents as have heretofore been generally employed in pest control compositions of similar type.
- Suitable surfaceactive agents are set out, for example, in Searle U.S. Patent 2,426,417; Todd U.S. Patent 2,655,447; I ones U.S. Patent 2,412,510; or Lenher US. Patent 2,139,276. A detailed list of such agents is set forth in Detergents and EmulsifiersUp to Date (1962) by John W. McCutcheon, Inc., and Bulletin E607 of the Bureau of Entomology and Plant Quarantine of the U.S. Department of Agriculture.
- Suitable surface-active agents for use in compositions of the present invention are: polyethylene glycol fatty esters and fatty alkylol amide condensates, alkyl aryl sulfonates, fatty alcohol sulfates, dialkyl esters of sodium sulfosuccinate, fatty acid esters of sodium isethionate, polyoxyethylene thioether and long chain quaternary ammonium chloride.
- the more preferred surfactants are the anionic and non-ionic type.
- the anionic surface-active agents preferred ones are alkali metal or amine salts of alkyl benzene sulfonic acids such as dodecylbenzene sulfonic acid, sodium lauryl sulfate, alkyl naphthalene sulfonates, sodium N-methyl-N-oleoyltaurate, oleic acid ester of sodium isethionate, dioctyl sodium sulfosuccinate, sodium dodecyldiphenoloxide disulfonate.
- alkyl benzene sulfonic acids such as dodecylbenzene sulfonic acid, sodium lauryl sulfate, alkyl naphthalene sulfonates, sodium N-methyl-N-oleoyltaurate, oleic acid ester of sodium isethionate, dioctyl
- nonionic compounds preferred members are alkyl phenoxy poly (ethyleneoxy) ethanols such as nonyl phenol ad 3,148,111 Patented Sept. 8, 1964 duets with ethylene oxide; trimethyl nonyl polyethylene glycol ethers, polyethylene oxide adducts of fatty and rosin acids, long chain alkyl mercaptan adducts with ethylene oxide.
- Surface-active dispersing agents such as sodium lignin sulfoantes, low viscosity methyl cellulose, polymerized sodium salts of alkyl naphthalene sulfonic acids are also suitable in the insect repellent compositions of this invention.
- compositions of this invention In general, less than 10% by weight of surfactants will be used in compositions of this invention and ordinarily the amount of surfactant will range from 1-5% but may even be less than 1% by weight.
- the insect repellent compositions of this invention can contain, with or without surfactant, finely divided inert diluents such as talcs, natural clays, including kaolinites, and attapulgite, pyrophyllite, diatomaceous earths, synthetic fine silicas, calcium silicate, carbonates, calcium phosphates, sulfur, lime, and such flours as walnut shell, wheat, redwood, soybean and cottonseed.
- finely divided inert diluents such as talcs, natural clays, including kaolinites, and attapulgite, pyrophyllite, diatomaceous earths, synthetic fine silicas, calcium silicate, carbonates, calcium phosphates, sulfur, lime, and such flours as walnut shell, wheat, redwood, soybean and cottonseed.
- the amount of finely divided inert solid diluent can vary widely and ordinarily will range from 10 to 99% by weight of the insect repellent composition.
- Particle size of the inert solid diluent can vary considerably but will ordinarily be somewhat under 50 microns in the finished formulation.
- the repellent compositions of this invention can also be applied as solutions which are sprayed, brushed or wiped on the surface from which insects are to be repelled.
- the repellent materials are mixed with a diluent such as, for example, naphtha, kerosene, toluene, xylene, nitrobenzene, chlorobenzene, cyclohexanone, acetone, methylisobutyl ketone or a mixture of high boiling isoparaffinic hydrocarbons.
- a diluent such as, for example, naphtha, kerosene, toluene, xylene, nitrobenzene, chlorobenzene, cyclohexanone, acetone, methylisobutyl ketone or a mixture of high boiling isoparaffinic hydrocarbons.
- the preferred isoparafiinic hydrocarbon fraction has a boiling point in the range of 260 F. to 800 F. and is commonly known
- the repellent compositions of this invention can also be applied in the form of an aqueous emulsion.
- the active ingredients can be dissolved in a substantially water insoluble solvent such as one of the aforementioned solvents and the resulting solution emulsified with water. Any one of the emulsifying or wetting agents mentioned above can be employed.
- the concentration of active ingredient in the solvent, with or without surfactant to make the mixture emulsifiable can range from dilute solutions, upwards of 1% to more concentrated solutions containing 30% and even 40% active ingredient. While the former are suitable for direct application, solutions having a strength greater than about 20% are particularly suitable as concentrates which are diluted with solvents, or are emulsified in water, at the time of application. For certain applications concentrates containing more than 40% of the repellent compound may be useful. In such compositions the active ingredient may range to the rest being one of the above mentioned solvents, possibly mixed with a surfactant. These concentrates, While solids under normal conditions of temperature, emulsify or dissolve rapidly and easily to give useful, more dilute sprays.
- compositions of this invention can also contain, if desired, an odorant such as perfume. Additionally, compositions can contain other known insect repellents such as succinic acid-di-n-butyl-ester or m-toluic acid-di-ethylamide.
- compositions of this invention can be sprayed, brushed or spread directly on the animal or inanimate surface to be protected.
- the exact amount of active ingredients will vary according to the type of surface to be protected, the time of the year and like variables. In general, however, surfaces to be protected will be sprayed or brushed so that a thin film of active agent is established.
- Example 1 Percent Methyl o-nitrophenyl sulfide 25.0 Mixed polyoxyethylene ethers and oil soluble petroleum sulfonates 6.0 Xylene 69.0
- the above emulsifiable oil is prepared by simple mixing of the components to yield a clear solution.
- This composition is diluted with deodorized kerosene (Deobase) to a concentration of 1% active and applied by means of a compressed air sprayer to the basement walls and behind the counters of a restaurant. Cockroaches are repelled from the treated areas for an extended period.
- Deobase deodorized kerosene
- Example 2 Percent Methyl o-nitrophenyl sulfide 50.0 Alkyl naphthalene sulfonic acid, Na salt 1.5 Partially desulfonated sodium lignin sultonate 1.0
- Methyl o-nitrophenyl sulfide 3.0 Diatomaceous silica 2.0 Micaceous talc 95.0
- the active and minor diluent are first mixed and micropulverized, then blended with the major diluent to give a dust composition.
- the dust is applied to the face and backs of cattle to repel fiies and other annoying insect species.
- Example 4 The composition of Example 1 is applied to fiber board packaging material by conventional coating equipment. The resultant fiber board is used for fabricating packing cases for cartons of dry cereal. Stored-product insects are repelled from the treated cases and the contents thereby protected from insect damage.
- Example 5 The under surface of a wool rug is sprayed with the composition of Example 2 at the rate of 0.2 gram active per square foot. When laid in a house in the conventional manner, extended protection of the rug from carpet beetle attack is provided by the repellency of this methyl o-nitrophenyl sulfide treatment.
- Examples 6-10 Ethyl o-nitrophenyl sulfide is substituted for methyl o-nitrophenyl sulfide in each of the Examples 1 to 5 in like amount by weight.
- the composition is mixed in the same manner and when applied in like manner gives like results.
- R is alkyl of less than 3 carbon atoms.
- Method of imparting insect repellency to the surface of animals and inanimate objects which comprises applying to said surface in an amount sufiicient to repel insects methyl o-nitrophenyl sulfide.
- Method of imparting insect repellency to the surface of animals and inanimate objects which comprises applying to said surface in an amount sufiicient to repel insects ethyl o-nitrophenyl sulfide.
Description
United States Patent 3,148,111 IVIETHOD 0F REPEILING INSECTS EMPLOYING NTTROPHENYL SULFIDES Edward J. Soboczenski, Chadds Ford, Pa., assignor to E. I. du Pont de Nemours and Company, Wilmington, DeL, a corporation of Delaware No Drawing. Filed Aug. 1, 1962, Ser. No. 213,373 3 Claims. (Cl. 167-30) This invention relates to insect repellents. More specifically, it refers to the use of alkyl o-nitrophenyl sulfides and compositions containing them as insect repellents.
The search continues for improved insect repellents. According to this invention it is quite surprisingly discovered that methyl and ethyl o-nitrophenyl sulfides are effective insect repellents when used in the manner of this invention. Most repellents are effective against only one or two insect species. However, the repellent of this invention is effective against many insect species.
The active compounds of this invention have the structural formula:
wherein R is methyl or ethyl.
Use.The alkyl o-nitrophenyl sulfides used in this invention are excellent insect repellents. Insects repelled include such insects as German cockroach and other roach species, confused fiour beetle, black carpet beetle, house fly and Mexican bean beetle. The compounds of this invention, when used in compositions containing liquid diluents or solid particulate diluents, protect treated surfaces such as industrial equipment and backs of cattle from being attacked by the described insects.
Composition-Insect repellent compositions of this invention will ordinarily comprise at least one compound of formula 1 with one or more surfactants, or with a finely divided solid diluent or a liquid diluent.
The surface-active agents used in this invention to assist dispersion of the composition can be a dispersant, wetting agent or emulsifying agent. The surface-active agent or surfactant can include such anionic, cationic and non-ionic agents as have heretofore been generally employed in pest control compositions of similar type. Suitable surfaceactive agents are set out, for example, in Searle U.S. Patent 2,426,417; Todd U.S. Patent 2,655,447; I ones U.S. Patent 2,412,510; or Lenher US. Patent 2,139,276. A detailed list of such agents is set forth in Detergents and EmulsifiersUp to Date (1962) by John W. McCutcheon, Inc., and Bulletin E607 of the Bureau of Entomology and Plant Quarantine of the U.S. Department of Agriculture.
Suitable surface-active agents for use in compositions of the present invention are: polyethylene glycol fatty esters and fatty alkylol amide condensates, alkyl aryl sulfonates, fatty alcohol sulfates, dialkyl esters of sodium sulfosuccinate, fatty acid esters of sodium isethionate, polyoxyethylene thioether and long chain quaternary ammonium chloride.
Among the more preferred surfactants are the anionic and non-ionic type. Among the anionic surface-active agents, preferred ones are alkali metal or amine salts of alkyl benzene sulfonic acids such as dodecylbenzene sulfonic acid, sodium lauryl sulfate, alkyl naphthalene sulfonates, sodium N-methyl-N-oleoyltaurate, oleic acid ester of sodium isethionate, dioctyl sodium sulfosuccinate, sodium dodecyldiphenoloxide disulfonate. Among the nonionic compounds, preferred members are alkyl phenoxy poly (ethyleneoxy) ethanols such as nonyl phenol ad 3,148,111 Patented Sept. 8, 1964 duets with ethylene oxide; trimethyl nonyl polyethylene glycol ethers, polyethylene oxide adducts of fatty and rosin acids, long chain alkyl mercaptan adducts with ethylene oxide. Surface-active dispersing agents such as sodium lignin sulfoantes, low viscosity methyl cellulose, polymerized sodium salts of alkyl naphthalene sulfonic acids are also suitable in the insect repellent compositions of this invention.
In general, less than 10% by weight of surfactants will be used in compositions of this invention and ordinarily the amount of surfactant will range from 1-5% but may even be less than 1% by weight.
The insect repellent compositions of this invention can contain, with or without surfactant, finely divided inert diluents such as talcs, natural clays, including kaolinites, and attapulgite, pyrophyllite, diatomaceous earths, synthetic fine silicas, calcium silicate, carbonates, calcium phosphates, sulfur, lime, and such flours as walnut shell, wheat, redwood, soybean and cottonseed.
The amount of finely divided inert solid diluent can vary widely and ordinarily will range from 10 to 99% by weight of the insect repellent composition.
Particle size of the inert solid diluent can vary considerably but will ordinarily be somewhat under 50 microns in the finished formulation.
The repellent compositions of this invention can also be applied as solutions which are sprayed, brushed or wiped on the surface from which insects are to be repelled. For this method of application, the repellent materials are mixed with a diluent such as, for example, naphtha, kerosene, toluene, xylene, nitrobenzene, chlorobenzene, cyclohexanone, acetone, methylisobutyl ketone or a mixture of high boiling isoparaffinic hydrocarbons. The preferred isoparafiinic hydrocarbon fraction has a boiling point in the range of 260 F. to 800 F. and is commonly known as Soltrol. Other suitable solvents include chlorinated aliphatic hydrocarbons, high boiling ethers, Cellosolves, Carbitols and the like.
The repellent compositions of this invention can also be applied in the form of an aqueous emulsion. The active ingredients can be dissolved in a substantially water insoluble solvent such as one of the aforementioned solvents and the resulting solution emulsified with water. Any one of the emulsifying or wetting agents mentioned above can be employed.
The concentration of active ingredient in the solvent, with or without surfactant to make the mixture emulsifiable, can range from dilute solutions, upwards of 1% to more concentrated solutions containing 30% and even 40% active ingredient. While the former are suitable for direct application, solutions having a strength greater than about 20% are particularly suitable as concentrates which are diluted with solvents, or are emulsified in water, at the time of application. For certain applications concentrates containing more than 40% of the repellent compound may be useful. In such compositions the active ingredient may range to the rest being one of the above mentioned solvents, possibly mixed with a surfactant. These concentrates, While solids under normal conditions of temperature, emulsify or dissolve rapidly and easily to give useful, more dilute sprays.
The compositions of this invention can also contain, if desired, an odorant such as perfume. Additionally, compositions can contain other known insect repellents such as succinic acid-di-n-butyl-ester or m-toluic acid-di-ethylamide.
Applicatiom-The compositions of this invention can be sprayed, brushed or spread directly on the animal or inanimate surface to be protected. The exact amount of active ingredients will vary according to the type of surface to be protected, the time of the year and like variables. In general, however, surfaces to be protected will be sprayed or brushed so that a thin film of active agent is established.
In addition to the examples described above, the following examples are provided to more clearly describe the invention. It is understood that all percents are weight unless otherwise indicated.
Example 1 Percent Methyl o-nitrophenyl sulfide 25.0 Mixed polyoxyethylene ethers and oil soluble petroleum sulfonates 6.0 Xylene 69.0
The above emulsifiable oil is prepared by simple mixing of the components to yield a clear solution. This composition is diluted with deodorized kerosene (Deobase) to a concentration of 1% active and applied by means of a compressed air sprayer to the basement walls and behind the counters of a restaurant. Cockroaches are repelled from the treated areas for an extended period.
Example 2 Percent Methyl o-nitrophenyl sulfide 50.0 Alkyl naphthalene sulfonic acid, Na salt 1.5 Partially desulfonated sodium lignin sultonate 1.0
Synthetic fine silica 47.5
Methyl o-nitrophenyl sulfide 3.0 Diatomaceous silica 2.0 Micaceous talc 95.0
The active and minor diluent are first mixed and micropulverized, then blended with the major diluent to give a dust composition. The dust is applied to the face and backs of cattle to repel fiies and other annoying insect species.
4 Example 4 The composition of Example 1 is applied to fiber board packaging material by conventional coating equipment. The resultant fiber board is used for fabricating packing cases for cartons of dry cereal. Stored-product insects are repelled from the treated cases and the contents thereby protected from insect damage.
Example 5 The under surface of a wool rug is sprayed with the composition of Example 2 at the rate of 0.2 gram active per square foot. When laid in a house in the conventional manner, extended protection of the rug from carpet beetle attack is provided by the repellency of this methyl o-nitrophenyl sulfide treatment.
Examples 6-10 Ethyl o-nitrophenyl sulfide is substituted for methyl o-nitrophenyl sulfide in each of the Examples 1 to 5 in like amount by weight. The composition is mixed in the same manner and when applied in like manner gives like results.
The invention claimed is:
1. Method of imparting insect repellency to the surface of animals and inanimate objects which comprises applying to said surface in an amount sufiicient to repel insects a compound of the formula:
wherein R is alkyl of less than 3 carbon atoms.
2. Method of imparting insect repellency to the surface of animals and inanimate objects which comprises applying to said surface in an amount sufiicient to repel insects methyl o-nitrophenyl sulfide.
3. Method of imparting insect repellency to the surface of animals and inanimate objects which comprises applying to said surface in an amount sufiicient to repel insects ethyl o-nitrophenyl sulfide.
References Cited in the tile of this patent King: US. Dept. Agr. Handbook No. 69 (May 1954), page 319.
Claims (1)
1. METHOD OF IMPARTING INSECT REPELLENCY TO THE SURFACE OF ANIMALS AND INANIMATE OBJECTS WHICH COMPRISES APPLYING TO SAID SURFACE IN AN AMOUNT SUFFICIENT TO REPEL INSECTS A COMPOUND OF THE FORMULA:
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US20050058681A1 (en) * | 2003-09-12 | 2005-03-17 | Johnson Louis B. | Odorless insect repellant and method of use |
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