US2564663A - Insect repellents - Google Patents
Insect repellents Download PDFInfo
- Publication number
- US2564663A US2564663A US69831A US6983149A US2564663A US 2564663 A US2564663 A US 2564663A US 69831 A US69831 A US 69831A US 6983149 A US6983149 A US 6983149A US 2564663 A US2564663 A US 2564663A
- Authority
- US
- United States
- Prior art keywords
- insect
- ester
- furylacrylic acid
- carbon atoms
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000077 insect repellent Substances 0.000 title claims description 12
- ZCJLOOJRNPHKAV-ONEGZZNKSA-N (e)-3-(furan-2-yl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=CO1 ZCJLOOJRNPHKAV-ONEGZZNKSA-N 0.000 claims description 12
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 241000238631 Hexapoda Species 0.000 description 9
- 239000004744 fabric Substances 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- -1 aliphatic alcohols Chemical class 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- 241000256111 Aedes <genus> Species 0.000 description 2
- 241000256190 Anopheles quadrimaculatus Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 description 1
- 241000256118 Aedes aegypti Species 0.000 description 1
- 241000256186 Anopheles <genus> Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 101100456896 Drosophila melanogaster metl gene Proteins 0.000 description 1
- 208000006877 Insect Bites and Stings Diseases 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/34—Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
-
- 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
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
Definitions
- This invention relates to insect repellents.
- esters of furylacrylic acid contemplated in our invention have the structural formula O.CH:CH.CH:C.CH:CPCOOR wherein R is the residue of an aliphatic alcohol having at least four carbon atoms.
- Tests to measure the repellency of the abovementioned compounds against insects by skin application were conducted by smearing the compound on the arms of test personnel, who then thrust their arms into cages containing insects. The arms were exposed for 30-minute intervals at 3 minutes each until the first insect bite.
- Tests to measure the repellency of fabrics impregnated with the above-mentioned compounds against insects were conducted by uniformly impregnating mercerized cotton hose with the compound at a rate equivalent to 3.3 gms. per sq. ft., drawing the dried hose over the arms of test personnel, who then thrust their covered arms into cages containing insects for 1 to 2 minutes.
- Examples of aliphatic alcohols with at least 4 carbon atoms, whose esterification products with furylacrylic acid have insect-repellent properties are, for instance, saturated compounds such as sec-butyl alcohol and amyl alcohol, unsaturated compounds such as methallyl alcohol, and alkoxy compounds such as cellosolve (2-ethoxy-ethanol).
- the furylacrylic acid esters contemplated by the present invention may be incorporated in a suitable inert liquid or solid carrier such as mineral oil, alcohol, petrolatum, etc.
- a suitable inert liquid or solid carrier such as mineral oil, alcohol, petrolatum, etc.
- an inert solvent such as alcohol, ether, etc.
- An insect repellent fabric comprising fabric impregnated with an ester of furylacrylic acid and of an aliphatic alcohol having 4 carbon atoms in its molecule.
- An insect-repellent fabric comprising fabric impregnated with the methallyl ester of furylacrylic acid.
- An insect-repellent fabric comprising fabric impregnated. with the Cellosolve ester of fury]- acrylic acid.
- An insect-repellent composition comprising in an inert non-gaseous organic carrier an ester of furylacrylic acid and of a saturated aliphatic alcohol having 4 carbon atoms in its molecule.
- An insect-repellent composition comprising the sec-butyl ester of furylacrylic acid in an inert non-gaseous organic carrier.
- An insect-repellent composition comprising the methallyl ester of furylacrylic acid in an inert non-gaseous organic carrier.
- An insect-repellentcomposition comprising the Cellosolve ester of furylacrylic acid in an inert non-gaseous organic carrier.
- An insect-repellent composition comprising an ester of furylacrylic acid and of an aliphatic alcohol having four carbon atoms in its molecule in a non-gaseous inert organic carrier.
- REFERENCES CITED UNITED STATES PA'IEN is Name Date Jones et al 4.. May 7, 1946 OTHER REFERENCES Gilman et al.: Preparation of Some Perfumes, from 1929 Chemical Abstracts. vol. 23, page 3993.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Patented Aug. 21, 1951 INSECT REPELLENTS Paul D. Bartlett, Weston,
North Adams, Mass., States of America as r tary of the Army and Sidney D. Ross,
assignors to the United epresented by the Secre- No Drawing. Application January 7, 1949, Serial No. 69,831
8 Claims.
This invention relates to insect repellents.
We have found that the application of an ester of furylacrylic acid and an aliphatic alcohol having at least 4 carbon atoms, when applied to the human skin or a fabric, effectively repels insects, particularly Aedes aegZ/Pti and Anopheles quadrimaculatus.
The esters of furylacrylic acid contemplated in our invention have the structural formula O.CH:CH.CH:C.CH:CPCOOR wherein R is the residue of an aliphatic alcohol having at least four carbon atoms.
Tests to measure the repellency of the abovementioned compounds against insects by skin application were conducted by smearing the compound on the arms of test personnel, who then thrust their arms into cages containing insects. The arms were exposed for 30-minute intervals at 3 minutes each until the first insect bite.
Tests to measure the repellency of fabrics impregnated with the above-mentioned compounds against insects were conducted by uniformly impregnating mercerized cotton hose with the compound at a rate equivalent to 3.3 gms. per sq. ft., drawing the dried hose over the arms of test personnel, who then thrust their covered arms into cages containing insects for 1 to 2 minutes.
Examples of aliphatic alcohols with at least 4 carbon atoms, whose esterification products with furylacrylic acid have insect-repellent properties, are, for instance, saturated compounds such as sec-butyl alcohol and amyl alcohol, unsaturated compounds such as methallyl alcohol, and alkoxy compounds such as cellosolve (2-ethoxy-ethanol).
The following table illustrates the results obtained by the above test methods against Aedes aegypti and Anopheles quadrimaculatus, as examples of insects against which the invention is applicable, by using compounds in accordance with the present invention.
Insect Repellency upon Application Insect Reto Skin pellency of Material i iffii Anopheles against i uadri- Aedes mnculatus Aegypti Mine. Mine. Sec-bartyl ester of iurylacrylic 188 62 over 5 days.
ac Am lcsteroiiurylacrylic acid. over 120 over days. Metl gllyl ester of iurylacrylic 198 38 Do.
ac Cellggolve ester of iurylacrylic 207 42 Do.
For ease of application, the furylacrylic acid esters contemplated by the present invention may be incorporated in a suitable inert liquid or solid carrier such as mineral oil, alcohol, petrolatum, etc. For facile and uniform fabric impregnation, they may be applied in an inert solvent, such as alcohol, ether, etc.
Havingthus fully described our invention, we claim:
1. An insect repellent fabric comprising fabric impregnated with an ester of furylacrylic acid and of an aliphatic alcohol having 4 carbon atoms in its molecule.
2. An insect-repellent fabric comprising fabric impregnated with the methallyl ester of furylacrylic acid.
3. An insect-repellent fabric comprising fabric impregnated. with the Cellosolve ester of fury]- acrylic acid.
4. An insect-repellent composition. comprising in an inert non-gaseous organic carrier an ester of furylacrylic acid and of a saturated aliphatic alcohol having 4 carbon atoms in its molecule.
5. An insect-repellent composition comprising the sec-butyl ester of furylacrylic acid in an inert non-gaseous organic carrier.
6. An insect-repellent composition comprising the methallyl ester of furylacrylic acid in an inert non-gaseous organic carrier.
7. An insect-repellentcomposition comprising the Cellosolve ester of furylacrylic acid in an inert non-gaseous organic carrier.
8. An insect-repellent composition comprising an ester of furylacrylic acid and of an aliphatic alcohol having four carbon atoms in its molecule in a non-gaseous inert organic carrier.
PAUL D. BARTLETT. SIDNEY D. ROSS.
REFERENCES CITED UNITED STATES PA'IEN is Name Date Jones et al 4.. May 7, 1946 OTHER REFERENCES Gilman et al.: Preparation of Some Perfumes, from 1929 Chemical Abstracts. vol. 23, page 3993.
OSRD Bimonthly Progress Report No. 24, Section 1, Period Ending June 30, 1945, particularly page 7, Orlando Nos. 0-5865, 0-5884. Publication date, August 1, 1947. I
OSRD Insect Control Committee Report No. 16, Interim Report No. 0-87, February 1, 1945, particularly pages 72, 74, Orlando Nos. 0-3301, 0-4246. Publication date, August 1, 1947.
Eddy et al.: Further tests Chemical Abstracts, vol. 41, 1947, pages 3575 and 3576.
Number
Claims (1)
- 4. AN INSECT-REPELLENT COMPOSITION COMPRISING IN AN INERT NON-GASEOUS ORGANIC CARRIER AN ESTER OF FURYLACRYLIC ACID AND OF A SATURATED ALIPHATIC ALCOHOL HAVING 4 CARBON ATOMS IN ITS MOLECULE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69831A US2564663A (en) | 1949-01-07 | 1949-01-07 | Insect repellents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69831A US2564663A (en) | 1949-01-07 | 1949-01-07 | Insect repellents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2564663A true US2564663A (en) | 1951-08-21 |
Family
ID=22091473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US69831A Expired - Lifetime US2564663A (en) | 1949-01-07 | 1949-01-07 | Insect repellents |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2564663A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050064003A1 (en) * | 2002-03-29 | 2005-03-24 | Nourigat Robert M. | Method for preventing pests from entering a building structure |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2400006A (en) * | 1945-03-03 | 1946-05-07 | Us Agriculture | Insect repellent compositions |
-
1949
- 1949-01-07 US US69831A patent/US2564663A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2400006A (en) * | 1945-03-03 | 1946-05-07 | Us Agriculture | Insect repellent compositions |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050064003A1 (en) * | 2002-03-29 | 2005-03-24 | Nourigat Robert M. | Method for preventing pests from entering a building structure |
| US7059081B2 (en) | 2002-03-29 | 2006-06-13 | Nourigat Robert M | Method for preventing pests from entering a building structure |
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