CA1196278A - Insect repellants - Google Patents
Insect repellantsInfo
- Publication number
- CA1196278A CA1196278A CA000424690A CA424690A CA1196278A CA 1196278 A CA1196278 A CA 1196278A CA 000424690 A CA000424690 A CA 000424690A CA 424690 A CA424690 A CA 424690A CA 1196278 A CA1196278 A CA 1196278A
- Authority
- CA
- Canada
- Prior art keywords
- parts
- weight
- deet
- peg
- insect repellant
- 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
Links
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
- A01N25/02—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 containing liquids as carriers, diluents or solvents
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicinal Preparation (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
The invention relates to insect repellant compositions of N,N-diethyl-m-toluamide (DEET') in alcoholic solution and containing PEG 400. The insect repellant compositions of the invention are found to provide unexpected prolonged activity over that obtained in corresponding compositions without PEG 400.
The invention relates to insect repellant compositions of N,N-diethyl-m-toluamide (DEET') in alcoholic solution and containing PEG 400. The insect repellant compositions of the invention are found to provide unexpected prolonged activity over that obtained in corresponding compositions without PEG 400.
Description
The present invention relates to insec-t repel-lants, for use on human skin, which ~re based on N,N-diethyl-m-toluamide (DEET) and have a prolonged activity.
DEET is a known and proven insect repellant and is generally accepted as a very good "all-round repellant" [Kochhar, R~Ko ~ Dixit, R.S., Somaya, C.J.;
Indian J. Med. Res., 629 1 January 1974].
For a desirable activity of 6 to 8 hours on human s~in, a concentra-tion of 30% to 50% is required in form~lations which are usually customary (ethanolic or isopropanolic solutions) [Now~k, G.A.; Die kosmetischen Pr~parate (Cosmetic products). Verlag f~r chem. Industrie H. Ziolkowsky KG 584 Augsburg 197,53.
The duration of the activity of repellan-t formu-lations against mosquitoes is usually -tested in vivo on the yellow fever mosquito (Aedes aegypti) [Lust, S.;
Parf. uO KosmO, 417304 (1960)~o In this test, in each case 500 female mosquitoes are introduced înto a 35 x 35 x 35 cm cage covered with gauze. The readi-ness of the mosquitoes to bite is tested by introducing an arm of the particu ar test person. m e landing, biting and sucking of a relatively large number of mos-~uitoes is regarded as the cri-terion of positive readi-ness to bite.
The repellants are tested in a laboratory at a temperature of. 22C and at a relative atmospheric humi-dity of 70 ~ 10%. The test substances are applied immediately before the start of the experiment. The amount of 0.1 + 0.01 ml of repellant substance is applied with a glass rod, as far as possible uni~ormly, to an area of 100 cm on the lower ~rm of the subject, Adhesive is -then applied around the edges of -the treated area. The remaining area of arm is covered with a Le A 21 622 plastic glove, which reaches up to the shouldersO
An influencing of the mosquitoes by secretions from the skin wh;ch attract the mosquitoes can thereby be excluded~
The arm treated in this manner is introduced into the mosquito cage, contact between the open ar~a of the arm and the gauze being prevented in order to avoid con-tamination of the gauze and simultaneous loss of repel-lant substance from -the area of arm~ The arm is introduced directly after application and at hourly intervals. The exposure time is in each case 5 minutes. It is assumed that the action of a sub-stance has ended when at least 2 mosquitoes have sucked their fill on the treated area during this timespan~
Fig. 1 shows the dependence of the duration of activity on the DEET concentration, determined by the method described above. m e concentration of DEET
in % has been plotted along the abscissa and the duration of activity in hours has been plotted along the ordinate.
The graph shown in Figo 1 shows an un~avourable pa~h in the area of higher concentrationsO According to our investigations, this is mostly ~o be attributed to absorption of the DEETo me absorbed portion o~
DEET is no longer a~ailable for repelling insects7 It is known that other substances, such as per-fume oils, water, solubilising agents and fats, can be added to alcoholic solutions of DEET~ These additives serve to improve the fragrance, consistency, ease of distribution and~feeling on the skin.
Combinations with other repellant active sub-- stances [Charlet, E~ Finkel, P., Strickmann, H.; Parf.
u. Kosm. 59, 367 (1978)~ are also known.
Substances have now been sought which reduce the absorption of DEET by human skin and thus increase the ~5 duration of activity. Surprisingly, it was possible to find that a significantly reduced absorption and an Le A 21 622 improved duration of activity was achieved by adding polyethylene glycol 400 (PEG 400). PEG L~O i-tself has no repellant action.
Figo 2 shows a comparison of ~he duration of ac~ivity of 20% strength DEET formulations without (1) an additive and with (2) the addition of 20% of PEG 400 .
The two formula-tions are plotted along the abscissa, and the duration of activi~J in hours is plot-ted along the ordinate. I~e duration of the activity of 20% of DEET in isopropanol is increased from 5.7 hours to 7.4 hours by adding 20% of PEG 400. m e formu-lation containing 20% of DEET and added PEG 400 is thus even superior to a 30/0 strength DEET solution withou-t an ~dditive in respect of the duration of activity.
A prolonged activity or, at the same activity, a lower use concentration of DEET has been achieved by the formulations according to the invention.
The concentration of DEET in the formulations according to the invention is between 5 and 50%, but preferably between 10 and 4G%. Concentrations between 15 and 25% are very particul~rly preferred.
Taking into consideration cosmetic requirements, the concentration of PEG 400 should be between 5 and ~5/
but preferably between 15 and 25%.
Suitable solvents are monohydric and polyhydric alcohols such as, for example, Cl-C3-alkanols, such as ethanol, isopropanol; C2-C5-alkanediols, such as ethylene or propylene glycol or C3-C6-alkanetriols, such as glycerol Further additives can be other repeilants [Charlet E Finkel, P., Strickmann, H.; Parf. u. KosmO 59, ~7 (1978)]; perfume oils to cover the intrinsic odour; aroma substances with their own repellant action (for example lemon oil, laverlder oil or oil of cinnamon)~ water and cosmetic bases, such as, ~or example, isopropyl myristate 9 paraffin oil and the like [Schrader, K~y Grundlagen und Rezepturen der Kosme-tika (Principles and recipes of cosmetics), Dr. Alfred H~thig Verlag Heidelberg, 1979].
~ / .
The formulations according to the invention are applied, like the known formulations ~lotion/spray) to freely exposed areas of skin in the correct use amountO
m e preparation and bottling of the lotions and aerosols according to the invention are effected as described in Nowak, G.A. [Die Kosmetischen Pr~parate (Cosmetic products), Verlag f~r chem. Industrie H. Ziolkowsky KG, 567-588 Aug~burq 1975~.
The examples which follow give a ~ew typical lO recipes, with parts being parts by weight.
1. DEET 5 parts PEG 400 5 parts Isopropanol 90 parts
DEET is a known and proven insect repellant and is generally accepted as a very good "all-round repellant" [Kochhar, R~Ko ~ Dixit, R.S., Somaya, C.J.;
Indian J. Med. Res., 629 1 January 1974].
For a desirable activity of 6 to 8 hours on human s~in, a concentra-tion of 30% to 50% is required in form~lations which are usually customary (ethanolic or isopropanolic solutions) [Now~k, G.A.; Die kosmetischen Pr~parate (Cosmetic products). Verlag f~r chem. Industrie H. Ziolkowsky KG 584 Augsburg 197,53.
The duration of the activity of repellan-t formu-lations against mosquitoes is usually -tested in vivo on the yellow fever mosquito (Aedes aegypti) [Lust, S.;
Parf. uO KosmO, 417304 (1960)~o In this test, in each case 500 female mosquitoes are introduced înto a 35 x 35 x 35 cm cage covered with gauze. The readi-ness of the mosquitoes to bite is tested by introducing an arm of the particu ar test person. m e landing, biting and sucking of a relatively large number of mos-~uitoes is regarded as the cri-terion of positive readi-ness to bite.
The repellants are tested in a laboratory at a temperature of. 22C and at a relative atmospheric humi-dity of 70 ~ 10%. The test substances are applied immediately before the start of the experiment. The amount of 0.1 + 0.01 ml of repellant substance is applied with a glass rod, as far as possible uni~ormly, to an area of 100 cm on the lower ~rm of the subject, Adhesive is -then applied around the edges of -the treated area. The remaining area of arm is covered with a Le A 21 622 plastic glove, which reaches up to the shouldersO
An influencing of the mosquitoes by secretions from the skin wh;ch attract the mosquitoes can thereby be excluded~
The arm treated in this manner is introduced into the mosquito cage, contact between the open ar~a of the arm and the gauze being prevented in order to avoid con-tamination of the gauze and simultaneous loss of repel-lant substance from -the area of arm~ The arm is introduced directly after application and at hourly intervals. The exposure time is in each case 5 minutes. It is assumed that the action of a sub-stance has ended when at least 2 mosquitoes have sucked their fill on the treated area during this timespan~
Fig. 1 shows the dependence of the duration of activity on the DEET concentration, determined by the method described above. m e concentration of DEET
in % has been plotted along the abscissa and the duration of activity in hours has been plotted along the ordinate.
The graph shown in Figo 1 shows an un~avourable pa~h in the area of higher concentrationsO According to our investigations, this is mostly ~o be attributed to absorption of the DEETo me absorbed portion o~
DEET is no longer a~ailable for repelling insects7 It is known that other substances, such as per-fume oils, water, solubilising agents and fats, can be added to alcoholic solutions of DEET~ These additives serve to improve the fragrance, consistency, ease of distribution and~feeling on the skin.
Combinations with other repellant active sub-- stances [Charlet, E~ Finkel, P., Strickmann, H.; Parf.
u. Kosm. 59, 367 (1978)~ are also known.
Substances have now been sought which reduce the absorption of DEET by human skin and thus increase the ~5 duration of activity. Surprisingly, it was possible to find that a significantly reduced absorption and an Le A 21 622 improved duration of activity was achieved by adding polyethylene glycol 400 (PEG 400). PEG L~O i-tself has no repellant action.
Figo 2 shows a comparison of ~he duration of ac~ivity of 20% strength DEET formulations without (1) an additive and with (2) the addition of 20% of PEG 400 .
The two formula-tions are plotted along the abscissa, and the duration of activi~J in hours is plot-ted along the ordinate. I~e duration of the activity of 20% of DEET in isopropanol is increased from 5.7 hours to 7.4 hours by adding 20% of PEG 400. m e formu-lation containing 20% of DEET and added PEG 400 is thus even superior to a 30/0 strength DEET solution withou-t an ~dditive in respect of the duration of activity.
A prolonged activity or, at the same activity, a lower use concentration of DEET has been achieved by the formulations according to the invention.
The concentration of DEET in the formulations according to the invention is between 5 and 50%, but preferably between 10 and 4G%. Concentrations between 15 and 25% are very particul~rly preferred.
Taking into consideration cosmetic requirements, the concentration of PEG 400 should be between 5 and ~5/
but preferably between 15 and 25%.
Suitable solvents are monohydric and polyhydric alcohols such as, for example, Cl-C3-alkanols, such as ethanol, isopropanol; C2-C5-alkanediols, such as ethylene or propylene glycol or C3-C6-alkanetriols, such as glycerol Further additives can be other repeilants [Charlet E Finkel, P., Strickmann, H.; Parf. u. KosmO 59, ~7 (1978)]; perfume oils to cover the intrinsic odour; aroma substances with their own repellant action (for example lemon oil, laverlder oil or oil of cinnamon)~ water and cosmetic bases, such as, ~or example, isopropyl myristate 9 paraffin oil and the like [Schrader, K~y Grundlagen und Rezepturen der Kosme-tika (Principles and recipes of cosmetics), Dr. Alfred H~thig Verlag Heidelberg, 1979].
~ / .
The formulations according to the invention are applied, like the known formulations ~lotion/spray) to freely exposed areas of skin in the correct use amountO
m e preparation and bottling of the lotions and aerosols according to the invention are effected as described in Nowak, G.A. [Die Kosmetischen Pr~parate (Cosmetic products), Verlag f~r chem. Industrie H. Ziolkowsky KG, 567-588 Aug~burq 1975~.
The examples which follow give a ~ew typical lO recipes, with parts being parts by weight.
1. DEET 5 parts PEG 400 5 parts Isopropanol 90 parts
2. DEET 50 parts PEG 400 35 parts Isopropanol 15 parts
3. DEET 20 parts PEG 400 20 parts Isopropanol 60 parts 20 4. DEET 12 parts PEG 400 8 parts Ethanol 60 parts Water 20 parts 5. DEET 25 parts PEG 400 25 parts - Isopropanol 30 parts Ethanol 19 parts Perfume oil 1 part Le A 21 622 __ i~ 3~78 / 6. DEET 15 parts PEG 400 20 parts Water 5 parts Isopropyl myristate 2 parts Isopropanol .57 parts Lavender oil 1 part 7. DEET 18 parts PEG 400 12 parts Dimethyl phthalate 4 parts Ethanol 65 parts Perfume oil 1 part 8. DEET 15 parts PEG 400 15 parts Ethylhexanediol 5 parts Isopropanol 57 parts Water 5 parts Propylene glycol 2 parts Perfume oil 1 part .
9. DEET 10 parts PEG 400 12 parts Paraffin oil 2 parts Isopropanol 75 parts Perfume oil 1 part 10. DEET 10 parts PEG 400 15 parts Propylene glycol 15 parts Isopropanol 60 parts Le A 21 622 ;
j~ ~19~
11. DEET 15 parts PEG 400 13 parts Glycerol 10 parts Water 8 parts Isopropanol 53 parts Perfume oil 1 part -Le A 21 622
9. DEET 10 parts PEG 400 12 parts Paraffin oil 2 parts Isopropanol 75 parts Perfume oil 1 part 10. DEET 10 parts PEG 400 15 parts Propylene glycol 15 parts Isopropanol 60 parts Le A 21 622 ;
j~ ~19~
11. DEET 15 parts PEG 400 13 parts Glycerol 10 parts Water 8 parts Isopropanol 53 parts Perfume oil 1 part -Le A 21 622
Claims (14)
1. An insect repellant which consists essentially of N,N-diethyl-m-toluamide (DEET) in alcoholic solution, and polyethylene glycol 400 (PEG 400).
2. An inert repellant of Claim 1 containing 5-50%, of DEET.
3. An insect repellant of Claim 2 containing 10-40%
of DEET.
of DEET.
4. An insect repellant of Claim 2 containing 15-25%
of DEET.
of DEET.
5. An insect repellant of Claim 1 containing 5-35%
of PEG 400.
of PEG 400.
6. An insect repellant of Claim 5 containing 15-25% of PEG 400.
7. An insect repellant of Claim 1, containing other repellants.
8. An insect repellant of Claim 1 containing perfume oils and/or aroma substances.
9. An insect repellant according to Claim 1 containing water.
10. An insect repellant of Claim 1 consisting essentially of 50 parts by weight DEET, 35 parts by weight PEG 400 and 15 parts by weight isopropanol.
11. An insect repellant of Claim 1 consisting essentially of 20 parts by weight DEET, 20 parts by weight PEG 400 and 60 parts by weight isopropanol.
12. An insect repellant of Claim 1 consisting essentially of 12 parts by weight DEET, 8 parts by weight PEG 400, 60 parts by weight ethanol and 20 parts by weight water.
13. An insect repellant of Claim 1 consisting essentially of 15 parts by weight DEET, 20 parts by weight PEG 400, 5 parts by weight water, 2 parts by weight isopropyl myristrate, 57 parts by weight isopropanol and 1 part by weight lavender oil.
14. An insect repellant of Claim 1 consisting essentially of 15 parts by weight DEET, 15 parts by weight PEG 400, 5 parts by weight ethylhexanediol, 57 parts by weight isopropanol, 5 parts by weight water, 2 parts by weight propylene glycol and 1 part by weight perfume oil.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3211633.0 | 1982-03-30 | ||
| DE19823211633 DE3211633A1 (en) | 1982-03-30 | 1982-03-30 | INSECT DRIVER |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1196278A true CA1196278A (en) | 1985-11-05 |
Family
ID=6159668
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000424690A Expired CA1196278A (en) | 1982-03-30 | 1983-03-28 | Insect repellants |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0090288B1 (en) |
| AT (1) | ATE13380T1 (en) |
| AU (1) | AU552551B2 (en) |
| CA (1) | CA1196278A (en) |
| DE (2) | DE3211633A1 (en) |
| GR (1) | GR78160B (en) |
| IE (1) | IE54939B1 (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1267838A (en) * | 1984-05-30 | 1990-04-17 | Frederick Coulston | Potentiated insect repellent composition and method |
| US5569411A (en) * | 1986-08-08 | 1996-10-29 | Colgate-Palmolive Co. | Liquid household cleaning composition with insect repellent |
| US5573700A (en) * | 1986-08-08 | 1996-11-12 | Colgate-Palmolive Co. | Liquid household cleaning composition with insect repellent |
| DE3842232A1 (en) * | 1988-12-15 | 1990-06-21 | Silke Boehm | Insect repellent, in particular tick repellent |
| IL102432A (en) * | 1991-07-24 | 1996-08-04 | Colgate Palmolive Co | Liquid household cleaning composition with insect repellent |
| IL102433A (en) * | 1991-07-24 | 1996-08-04 | Colgate Palmolive Co | Liquid household cleaning composition with insect repellent |
| WO1994016665A2 (en) * | 1993-01-25 | 1994-08-04 | Seleznev, Alexandr Georgievich | Agent to combat lice infestation |
| DE19722196C1 (en) * | 1997-05-27 | 1998-10-22 | Karl Engelhard Fabrik Pharm Pr | Di:ethyl-meta-toluamide based insect repellent composition |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3803303A (en) * | 1972-01-27 | 1974-04-09 | Kibben G Mc | Polymeric compositions for attracting cotton boll weevils |
| DE2925589C2 (en) * | 1979-06-25 | 1982-10-14 | Fichtel & Sachs Ag, 8720 Schweinfurt | Insect repellent |
-
1982
- 1982-03-30 DE DE19823211633 patent/DE3211633A1/en not_active Withdrawn
-
1983
- 1983-03-15 AU AU12463/83A patent/AU552551B2/en not_active Ceased
- 1983-03-18 AT AT83102684T patent/ATE13380T1/en not_active IP Right Cessation
- 1983-03-18 EP EP83102684A patent/EP0090288B1/en not_active Expired
- 1983-03-18 DE DE8383102684T patent/DE3360199D1/en not_active Expired
- 1983-03-28 GR GR70915A patent/GR78160B/el unknown
- 1983-03-28 CA CA000424690A patent/CA1196278A/en not_active Expired
- 1983-03-29 IE IE699/83A patent/IE54939B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0090288A1 (en) | 1983-10-05 |
| ATE13380T1 (en) | 1985-06-15 |
| GR78160B (en) | 1984-09-26 |
| IE830699L (en) | 1983-09-30 |
| AU1246383A (en) | 1983-10-06 |
| DE3360199D1 (en) | 1985-06-27 |
| DE3211633A1 (en) | 1983-10-13 |
| AU552551B2 (en) | 1986-06-05 |
| EP0090288B1 (en) | 1985-05-22 |
| IE54939B1 (en) | 1990-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |