CH628497A5 - Insect repellent - Google Patents
Insect repellent Download PDFInfo
- Publication number
- CH628497A5 CH628497A5 CH1298077A CH1298077A CH628497A5 CH 628497 A5 CH628497 A5 CH 628497A5 CH 1298077 A CH1298077 A CH 1298077A CH 1298077 A CH1298077 A CH 1298077A CH 628497 A5 CH628497 A5 CH 628497A5
- Authority
- CH
- Switzerland
- Prior art keywords
- salicylic acid
- toluamide
- diethyl
- general formula
- acid esters
- Prior art date
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
- 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
- A01N37/36—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N37/40—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Die vorliegende Erfindung betrifft neue insektenvertreibende Wirkstoffkombinationen aus dem bekannten Insektenvertreibungsmittel N,N-Diäthyl-m-toluamid und bekannten Salicylsäureestern. The present invention relates to new combinations of active insect repellants from the known insect repellant N, N-diethyl-m-toluamide and known salicylic acid esters.
N,N-DiäthyI-m-toIuamid ist ein seit langem bekanntes Insektenvertreibungsmittel (Repellent), das gegen Stechmük-ken aller Art, Bremsen, Sandfliegen, Zecken und andere Ungeziefer wirksam ist. Es hat sich ausserdem gezeigt, dass Salicylsäureester, insbesondere der Salicylsäure-2-hydroxy-äthylester, ebenfalls insektenvertreibend wirken. N, N-DiethyI-m-toIuamid is a long-known insect repellent that is effective against all kinds of mosquitoes, brakes, sand flies, ticks and other vermin. It has also been found that salicylic acid esters, in particular 2-hydroxyethyl salicylic acid, also have an insect-repelling effect.
Sowohl N,N-Diäthyl-m-toluamid als auch Salicylsäureester weisen jedoch bezüglich der Wirksamkeitsdauer je nach Insektenart grosse Unterschiede auf. So ist bei beiden Komponenten die Wirksamkeitsdauer gegen Zecken unzureichend und kann durch Erhöhung der Wirkstoffkonzentrationen nur unwesentlich verbessert werden. In letzter Zeit ist aber der Schutz vor Zecken um so wichtiger geworden, als sich gezeigt hat, dass die Zecken durch Übertragung von Viren eine Hirnhautentzündung auslösen können, die ihrerseits zu Todesfällen geführt hat. Both N, N-diethyl-m-toluamide and salicylic acid esters, however, have large differences in their duration of effectiveness depending on the type of insect. For both components, the duration of activity against ticks is inadequate and can only be slightly improved by increasing the active substance concentrations. However, protection against ticks has recently become all the more important since it has been shown that ticks can transmit viral inflammation through the transmission of viruses, which in turn has led to deaths.
Es wurde nun gefunden, dass neue Wirkstoffkombinationen aus N,N-Diäthyl-m-toluamid und Salicylsäureestern, insbesondere Salicylsäure-2-hydroxyäthylester, besonders lang anhaltend gegen Zecken wirksam sind. It has now been found that new active compound combinations of N, N-diethyl-m-toluamide and salicylic acid esters, in particular 2-hydroxyethyl salicylic acid, have a particularly long-lasting effect against ticks.
Es ist ausgesprochen überraschend, dass die erfindungsgemässen Wirkstoffkombinationen gegenüber Zecken eine signifikant längere Wirkungsdauer aufweisen, als der Summe der Wirkungen der einzelnen Wirkstoffe entsprechen würde. Es liegt also ein echter synergistischer Effekt vor. It is extremely surprising that the active substance combinations according to the invention have a significantly longer duration of action than ticks than would correspond to the sum of the effects of the individual active substances. So there is a real synergistic effect.
Auch im Vergleich zu Kombinationen verschiedener anderer bekannter Repellentien wurden für die erfindungsgemässen Wirkstoffkombinationen deutlich längere und bessere Wirkungen ermittelt. In comparison to combinations of various other known repellents, significantly longer and better effects were determined for the active compound combinations according to the invention.
40 40
in der R einen Alkylrest mit 1-4 Kohlenstoffatomen, der durch Hydroxylgruppen substituiert sein kann, bedeutet. Bevorzugt ist der Salicylsäure-2-hydroxyäthylester. in which R denotes an alkyl radical with 1-4 carbon atoms, which can be substituted by hydroxyl groups. Salicylic acid 2-hydroxyethyl ester is preferred.
Die erfindungsgemässen Wirkstoffkombinationen enthalten N,N-Diäthyl-m-toluamid in Konzentrationen beispielsweise bis zu 50%, vorzugsweise jedoch 10 bis 30%, sowie Salicylsäureester bis zu 25%, vorzugsweise jedoch 2 bis 10%. Sie können ferner alle bei Insektenvertreibungsmitteln üblichen nichttoxischen, inerten Hilfs- und Trägerstoffe enthalten. The active compound combinations according to the invention contain N, N-diethyl-m-toluamide in concentrations, for example, up to 50%, but preferably 10 to 30%, and salicylic acid esters up to 25%, but preferably 2 to 10%. They can also contain all non-toxic, inert auxiliaries and carriers which are customary in the case of insect repellants.
Die erfindungsgemässen Wirkstoffkombinationen vertreiben Insekten, wobei gegenüber Zecken im Labor- und Freilandversuch gewöhnlich Schutzzeiten von 6-9 Stunden ermittelt wurden. Demgegenüber erzielt man beispielsweise mit Zubereitungen, die 33% N,N-Diäthyl-m-toluamid enthalten, nur Schutzzeiten von 1-2 Stunden. Auch für Salicyl-säure-2-hydroxyäthylester wurde im allgemeinen eine maximale Schutzzeit von nur 1 Stunde 40 Minuten ermittelt. The active compound combinations according to the invention drive away insects, protection times of 6-9 hours being usually determined against ticks in laboratory and field trials. In contrast, with preparations containing 33% N, N-diethyl-m-toluamide, for example, protection times of only 1-2 hours are achieved. A maximum protection time of only 1 hour 40 minutes was generally also determined for 2-hydroxyethyl salicylic acid.
Die erfindungsgemässen Wirkstoffkombinationen werden in der Regel wie die bekannten Insektenvertreibungsmittel in der Form von Lösungen, Aerosolen, Emulsionen usw. angewandt. Die Anwendung erfolgt vorzugsweise äusserlich. The active compound combinations according to the invention are generally used in the form of solutions, aerosols, emulsions, etc., like the known insect repellants. The application is preferably external.
Beispiel 1 example 1
45 N,N-Diäthyl-m-toluamid 20,00 T1 45 N, N-diethyl-m-toluamide 20.00 T1
Salicylsäure-2-hydroxy-äthylester 5,00 T1 2-hydroxyethyl salicylic acid 5.00 T1
Isopropanol 73,50 T1 Isopropanol 73.50 T1
Parfüm 1,50 T1 Die Komponenten werden unter Rühren gemischt. Es so entsteht eine klare Lösung. Perfume 1.50 T1 The components are mixed with stirring. This creates a clear solution.
Beispiel 2 Example 2
N,N-Diäthyl-m-toluamid N, N-diethyl-m-toluamide
Salicylsäure-2-hydroxy-äthylester 2-hydroxyethyl salicylic acid
Isopropanol Isopropanol
Parfüm Perfume
35,00 Ti 10,00 TI 53,50 TI 1,50 TI 35.00 Ti 10.00 TI 53.50 TI 1.50 TI
Die Herstellung erfolgt wie unter Beispiel 1 beschrieben. The preparation is carried out as described in Example 1.
60 Beispiel 3 60 Example 3
N,N-Diäthyl-m-toluamid 35,00 T1 N, N-diethyl-m-toluamide 35.00 T1
Salicylsäure-methylester 10,00 T1 Salicylic acid methyl ester 10.00 T1
Isopropanol 53,50 T1 Isopropanol 53.50 T1
Parfümöl 1,50 T1 Perfume oil 1.50 T1
65 Die Herstellung erfolgt wie unter Beispiel 2 beschrieben. Anstelle von Salicylsäure-methylester können in analoger Weise auch der Äthyl-, n-Propyl-, iso-Propyl-, n-Butyl- oder iso-Butylester verwendet werden. 65 The preparation is carried out as described in Example 2. Instead of methyl salicylic acid, the ethyl, n-propyl, iso-propyl, n-butyl or iso-butyl ester can also be used in an analogous manner.
3 3rd
628 497 628 497
Beispiel 4 Example 4
N,N-Diäthyl-m-toluamid 20,00 TI N, N-diethyl-m-toluamide 20.00 TI
Salicylsäure-2-hydroxy-äthylester 5,00 TI 2-hydroxyethyl salicylic acid 5.00 TI
Isopropanol 74,50 TI Isopropanol 74.50 TI
Parfümöl 0,50 TI Perfume oil 0.50 TI
Die Herstellung der Lösung erfolgt wie unter Beispiel 1 beschrieben. Zur Herstellung eines Aerosolpräparates wird diese Lösung in einen Druckgasbehälter gefüllt und mit Treibgas versetzt. The solution is prepared as described in Example 1. To produce an aerosol preparation, this solution is filled into a pressurized gas container and propellant is added.
Beispiel 5 Example 5
Emulsion Typ O/W Emulsion type O / W
A. Kollodoidisperses Gemisch aus 90 T1 Cetylstearyl-alkohol und 10 T1 Natrium-cetylstearylsulfat 4,00 T1 A. Collodoid-disperse mixture of 90 T1 cetylstearyl alcohol and 10 T1 sodium cetylstearyl sulfate 4.00 T1
Stearinsäure 8,00 T1 Stearic acid 8.00 T1
Ölsäure des Decylalkohols 6,00 T1 Oleic acid of decyl alcohol 6.00 T1
B. N,N-Diäthyl-m-toluamid 20,00 T1 B. N, N-Diethyl-m-toluamide 20.00 T1
Salicylsäure-3-hydroxy-äthylester 5,00 T1 Polyoxyäthylen-glycerin- 3-hydroxyethyl salicylic acid 5.00 T1 polyoxyethylene glycerol
monorizinoleat 5,00 T1 monorizin oleate 5.00 T1
s C. Wasser, entmineralisiert 28,50 T1 s C. water, demineralized T1 28.50
Triäthanolamin 0,20 T1 Triethanolamine 0.20 T1
Dehydracetsäure-Natriumsalz 0,10 T1 Dehydroacetic acid sodium salt 0.10 T1
D. Wasser, entmineralisiert 20,00 T1 Kollodiales Magnesium- D. water, demineralized 20.00 T1 colloidal magnesium
io Aluminiumsilikat 2,00 T1 io aluminum silicate 2.00 T1
E. Formaldehyd-derivat 0,20 T1 E. Formaldehyde derivative 0.20 T1
F. Parfümöl 1,00 T1 F. Perfume oil 1.00 T1
B und C werden gelöst und auf 75 °C erwärmt. A wird bei 70% gelöst und in B/C eingerührt. B and C are dissolved and heated to 75 ° C. A is dissolved at 70% and stirred into B / C.
15 D wird dispergiert und bei 50 °C zu A/B/C gegeben. 15 D is dispersed and added to A / B / C at 50 ° C.
Unter weiterem Rühren wird E bei 45 °C und F bei 35 °C zugegeben. With further stirring, E is added at 45 ° C and F at 35 ° C.
Claims (4)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762648598 DE2648598C2 (en) | 1976-10-27 | 1976-10-27 | Insect repellants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH628497A5 true CH628497A5 (en) | 1982-03-15 |
Family
ID=5991511
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1298077A CH628497A5 (en) | 1976-10-27 | 1977-10-25 | Insect repellent |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT354804B (en) |
| CH (1) | CH628497A5 (en) |
| DE (1) | DE2648598C2 (en) |
| FR (1) | FR2368889A1 (en) |
| GR (1) | GR65225B (en) |
| NL (1) | NL7711656A (en) |
| SE (1) | SE7712053L (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1176167A (en) * | 1980-03-06 | 1984-10-16 | John J. Windheuser | Use of n,n-diethyl-m-toluamide for enhancing skin permeation of bio-affecting agents |
| NO306533B1 (en) * | 1998-04-21 | 1999-11-22 | Gunnar Volden | insecticide |
| DE10034396A1 (en) * | 2000-07-14 | 2002-01-31 | Bayer Ag | Creeping insect deterrent compositions |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1911551A (en) * | 1933-05-30 | Clarence r | ||
| US2808359A (en) * | 1957-02-19 | 1957-10-01 | Alfred F Schmutzler | Insect repellent compositions of hydroxy-alkyl esters of polybasic organic acids and methods of using same |
| CA1040097A (en) * | 1974-07-26 | 1978-10-10 | The Gillette Company | Insect repellant |
-
1976
- 1976-10-27 DE DE19762648598 patent/DE2648598C2/en not_active Expired
-
1977
- 1977-10-24 NL NL7711656A patent/NL7711656A/en not_active Application Discontinuation
- 1977-10-25 CH CH1298077A patent/CH628497A5/en not_active IP Right Cessation
- 1977-10-25 GR GR54638A patent/GR65225B/en unknown
- 1977-10-26 FR FR7732275A patent/FR2368889A1/en active Granted
- 1977-10-26 SE SE7712053A patent/SE7712053L/en unknown
- 1977-10-27 AT AT768077A patent/AT354804B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AT354804B (en) | 1979-01-25 |
| NL7711656A (en) | 1978-05-02 |
| SE7712053L (en) | 1978-04-28 |
| DE2648598C2 (en) | 1979-01-11 |
| FR2368889B1 (en) | 1981-12-11 |
| FR2368889A1 (en) | 1978-05-26 |
| GR65225B (en) | 1980-07-30 |
| DE2648598B1 (en) | 1978-05-18 |
| ATA768077A (en) | 1979-06-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |