GB2054377A - Insect repellant - Google Patents
Insect repellant Download PDFInfo
- Publication number
- GB2054377A GB2054377A GB8019578A GB8019578A GB2054377A GB 2054377 A GB2054377 A GB 2054377A GB 8019578 A GB8019578 A GB 8019578A GB 8019578 A GB8019578 A GB 8019578A GB 2054377 A GB2054377 A GB 2054377A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phthalic acid
- ester
- insect repellant
- insect
- cyclohexanol
- 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.)
- Granted
Links
- 239000000077 insect repellent Substances 0.000 title claims abstract description 30
- AAIBYZBZXNWTPP-UHFFFAOYSA-N 2-phenylcyclohexan-1-ol Chemical compound OC1CCCCC1C1=CC=CC=C1 AAIBYZBZXNWTPP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 15
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 claims abstract description 12
- -1 m - tolyl Chemical group 0.000 claims abstract description 7
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims description 19
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 claims description 18
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 claims description 9
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 9
- 239000003921 oil Substances 0.000 claims description 9
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 8
- 241000238631 Hexapoda Species 0.000 claims description 7
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 claims description 5
- 235000005979 Citrus limon Nutrition 0.000 claims description 5
- 244000131522 Citrus pyriformis Species 0.000 claims description 5
- 239000010627 cedar oil Substances 0.000 claims description 5
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims 6
- 150000002148 esters Chemical class 0.000 abstract 3
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 abstract 1
- 239000000470 constituent Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 description 25
- 150000001875 compounds Chemical class 0.000 description 11
- 230000000694 effects Effects 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 230000002195 synergetic effect Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- OKIJSNGRQAOIGZ-UHFFFAOYSA-N Butopyronoxyl Chemical compound CCCCOC(=O)C1=CC(=O)CC(C)(C)O1 OKIJSNGRQAOIGZ-UHFFFAOYSA-N 0.000 description 4
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 4
- 241000283690 Bos taurus Species 0.000 description 3
- 229960001673 diethyltoluamide Drugs 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 241000255925 Diptera Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- MMOXZBCLCQITDF-UHFFFAOYSA-N N,N-diethyl-m-toluamide Chemical compound CCN(CC)C(=O)C1=CC=CC(C)=C1 MMOXZBCLCQITDF-UHFFFAOYSA-N 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 210000004243 sweat Anatomy 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 241000256111 Aedes <genus> Species 0.000 description 1
- 241000256186 Anopheles <genus> Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 208000001431 Psychomotor Agitation Diseases 0.000 description 1
- 206010038743 Restlessness Diseases 0.000 description 1
- 208000003152 Yellow Fever Diseases 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000007882 cirrhosis Effects 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 230000002079 cooperative effect Effects 0.000 description 1
- 208000028104 epidemic louse-borne typhus Diseases 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 206010025482 malaise Diseases 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000001846 repelling effect Effects 0.000 description 1
- 206010061393 typhus Diseases 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
- 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)
- 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)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Insect repellant containing pthalic acid ester 2 - phenyl - cyclohexanol and m - tolyl acid diethylamide. The pthalic acid ester may be incorporated as a pthalic acid diethyl ester or pthalic acid dibutyl ester. The proportion of 2 - phenyl - cyclohexanol in proportion to the other constituents is very small.
Description
SPECIFICATION
Insect repellant
The invention relates to an insect repellant, containing a phthalic acid ester, 2 - phenyl - cyclohexanol and at least one further effective substance.
By the term 'insect repellant' there is to be understood in general terms material protective against sucking, biting, stinging, and in particular, sicknesscarrying insects. Both men and also animals can be protected against such troublesome insects if the skin, fabrics or the hide are treated with insect repellant. Especially on account of protection against insects which carry sicknesses such as yellow fever, malaria or typhus, insect repellants have a substantial practical importance. Therefore in the last decade more than 20,000 synthetic repellants have been researched, synthesized and tested. Although very many of the compounds were effective against insects, only very few compounds could be used in practice, since these compounds additionally to their effectiveness must also be compatible with human skin and also with clothing.It is, furthermore, very important that these compounds are of lowest poss ibie toxicity, have no unacceptable smell, exhibit a long-term effective action, are not adversely affected by sunlight or sweat and are effective against the widest possible spectrum of insects.
A compound, which acts relatively effectively to satisfy these requirements is the compound m-tolyl acid diethylamide, known on the market under the name DEET (R. Wegler, Chemistry of Plant Protection and Parasite Combatting Media, Volume 1; included therein K. H. Bushel, Insect Repellants, Page 492).
Other known and widely used compounds in practice are various phthalic acid esters, as well as the compound 2 - ethyl - 1,3 - hexanediol, which is known on the market under the name RUTGERS 612 (supra Page 490). These two compounds have, however, a relatively narrow effective spectrum and are not particularly stable. Also known are the compounds 2 - phenyl cyclohexanol and 2,2,4 -tremethyl - 1,3 - pentanediol (supra Page 494). Since these compounds however, do not in general fulfil the above-mentioned requirements as the hereinbefore mentioned compounds, the practical importance of the two last-mentioned compounds is not particularly great.
Since insect repellants having regard to their effective spectrum, their toxicity and their stability can vary widely, at an early stage research was undertaken so to mix various repellants with one another in order to combine good properties of individual repellants (supra Page 489). For such a mixing the effectiveness is set out in Table 1 (supra) in comparison with the effectiveness of single substances. This '622mixture' contains 60% phthalic acid dimethyl ester, 20% 2 - ethyl - 1,3 - - hexanediol and 20% Indalon.The table indicates that this mixture is more effective only against one kind of insect, namely anopheles, than the most effective individual substance, in relation to the two kinds of species aedes acts less effectively than the best individual substance and does not operate at all successfully on stornoxys. The effectiveness of the mixture is thus not substantially better than that of the individual substances. Furthermore, Indalon is used in this mixture which serves as a particularly effective repellant but which is on the one hand very costly and on the other hand very poisonous. It has been shown that as a sideeffect of the use of Indalon is cirrhosis of the liver (seethe Merck Index 1968, page 177 under "Butopyronoxyl").
The invention is based on the problem of providing a combined insect repellant, of which the effectiveness is substantially increased.
This problem is solved on the basis of an insect repellant containing phthalic acid ester, 2 - phenyl cyclohexanol and at least one further effective substance, solved by m-tolyl acid diethylamide as the further effective substance.
If one mixes a phthalic acid ester, for example phthalic acid dibutyl ester and 2 - phenyl cyclohexanol with the substance m-tolyl acid diethylamide in the ratio 1:0.02:1 (this repellantwill be hereinafter designated My )then there is established a wholly surprising synergistic effect. This relies particularly for effects of this kind, which on the basis of the sum of the individual effects of the components of the repellants which is to be expected.
As the phthalic acid esterthere can be used for example phthalic acid dimethyl ester, phthalic acid diethyl ester or phthalic dibutyl ester. Preferably there is used as phthalic acid ester, phthalic acid diethyl ester and phthalic acid dibutyl ester, together with 2 - phenyl cyclohexanol and mixed with this repellant with further substance m-tolyl acid diethylamide in the preferred proportion by weight of 1:1:0.02:1. Since the substance 2 - phenyl cyclohexanol is incorporated in comparatively small concentration, there is provided for the repellant a further advantage, of being comparatively cheap, since likewise this substance is very expensive. The repellant action remains however, in spite of this, unaffectedly good.
The insect repellant can in addition incorporate the substance 2 - ethyl - 1,3 - hexanediol and/or 2,2,4 trimethyl - 1,3 - pentanediol in the stated proportions by weight. The repelling action is thereby further improved.
The insect repellants in accordance with the invention can, furthermore, advantageously contain at least one etherial oil, whereby on the one hand the repellant action is additionally increased and on the other hand improvements relating to the smell and the skin acceptability are improved. Preferred etherial oils are lavender oil and/or cedarwood oil and/or oil of lemon.
An especially preferred embodiment of an insect repellant in accordance with the invention contains the following listed substances in the likewise indicated quantities.
Certain of the mathematical formula(e) appearing in the printed specification were
submitted in formal form after the date of filing.
COMPONENTS PROPORTION BY WEIGHT
Phthalic acid dibutyl ester 1
Phthalic acid diethyl ester 1 m-tolyl acid diethylamide 1 2-phenyl cyclohexanol 0.02 2 ethyl-1,3-hexanediol 1 2,2,4-trimethyl-1 ,3-pentanediol 1 lavender oil 0.0001 cedarwood oil 0.0001 oil of lemon 0.0001
This insect repellant is denoted hereinafter as M2.
The insect repellants in accordance with the invention can include customary vehicles and thinners.
There have been proposed as favourable for this purpose alcohol monomers, such as for example 2-propanol, and/or alcohol polymers, for example polyethyl glycol 200.
The repellants in accordance with the invention are manufactured by proportionate mixing of the individual components to be used.
The synergistic effect of two insect repellants in accordance with the invention were demonstrated by way of example on the common house fly (Musca domestica) under natural conditions in a cow stall.
House flies were particularly suited forth is demonstration, since they are particularly resistant to repellants.
The effect of the combination above detailed of the repellants M1 and M2 was compared with the action ofthe single substances and a calculated indicated cooperative effect ofthe substances compared. To this end 1 ml. of the substances to be compared was incorporated in a 1% isopropanol solution by means of a perfume atom riser simultaneously on 30 cm2 of the neck and shoulder region of cattie in a cow stall.
The measurement of the effect was carried out photographically by counting of flies which have died after (t) time intervals over the length (v) of 10 minutes on this surface. The results indicate in general terms three series of parallel tests (i = 3) to 60 minutes (t = 6) and are set out together in the table.
TABLE Repellant action of individual substances and of the mixtures M1 and M2
Substance* DEP DBP DEET PZOL EHOL TMP LOL ZOL COL M1 M2 Control K 0 2.2 1.5 0.6 2.5 4.2 2.0 3.2 2.7 1.8 3.1 2 bi.t (mean 1 1 0.3 0.7 0.3 2 1.3 1.3 0.3 0 0 0.3 population count 10 xt min) 2 2 1.3 0.7 1 3 1.3 0.7 1 1 0.7 0.3 3 2.3 1.7 0.7 1.7 3.3 1.7 1 0.7 2 0.7 0.7 4 2.3 2.3 1 1 3 1.7 1.7 1.7 1 1.3 0.7 5 2.3 2.3 1.3 1.7 3.6 2.6 2.3 2.7 2.3 1.3 1.3 6 2.7 2 1.3 2.3 3.7 3 2.3 3.7 2 0.3 1.3 Bt (mean population countfort=6time 2.1 1.7 1 1.6 3.1 1.9 1.6 1.7 1.4 0.8 0.7 intervals) Effectiveness W = Bt/K 1 1.1 1.6 0.6 0.7 1 0.5 0.6 0.8 0.4 0.2 Abbreviation s.S.8
ABBREVIATION NAME OF SUBSTANCE
DEP phthalic acid diethyl ester
DBP phthalic acid dibutyl ester
DEET m-tolyl acid diethylamide
PZOL 2-phenyl cyclohexanol
EHOL 2-ethyl-2,3-hexamediol TM P 2,2,4-trimethyi-1 ,3-pentanediol LOL lavender oil
ZOL cedarwood oil
COL oil of lemon
The synergistic effect of the above-mentioned
repellants M1 and M2 in accordance with the inven
tion can be expressed as a function (W) which
denotes the free space of a surface under considera
tion. For M1 and M2 it can be demonstrated with the
following equations that a better effect (WM) as can
be expected by the sum of the individual effects
(WE). If the function (W) is denoted by the equation: (1) W=Bt/Kwith (2) Bt = mean population countforttime intervals
and
(3) bj = mean population count from i parallel tests =
and
zj = Population count after c'efined time intervals (v) pertest and
K = control (thus the repellant effectiveness becomes smaller, the greater the value W) then this can be stated that related to the same quantity proportion of repellant substances, the sum of the effec tiveness ofthe individual substances (WE)
with n = numberof individual substances.
is greater than the effectiveness (WM) of the mixture, and thus
The synergistic effect can then be expressed by the expression
Correspondingly the tabulated values can be calculated only as the sum of the effectiveness of the individual substances (WE) according to the equation
(4) WE = (1.1 + 1.6 + 0.6)/3 = 1.1
The overall effectiveness of the insect repellant M1 in accordance with the invention compared in the table has a value of 0.4.
With the definition Esyn = WE/WM correspondingly the equation (6) thus gives
(6) Esyn M1 = 1.1/0.4 = 2.75
Since this value lies appreciably above 1 there is demonstrated with the insect repellant M1 in accordance with the invention combined, surprisingly synergistic effects, independently of the relatively large distribution of the measurement parameters (95% significance level) which is based on the high level of flying activity of the flies and partly on the restlessness of the cattle.
From the values for M2 taken from the table there can be calculated analogously the synergistic effect for M2. Corresponding to the measured values there can be calculated for the sum of the individual effects of the insect repellants M2 according to the equation (4) the value WE as follows: (4) WE=(1.0+1.1 +1.6+0.7+1.0+0.5+0.6+ 0.8)/9 = 0.85
The compared value listed in the table for the overall effect of M2, amounts to 0.2.
After insertion of the corresponding value in the equation (6)there is thus given
(6) Esyn M2 = 0.8/0.2 = 4
It is thus demonstrated that the synergistic effect by use of all substances claimed is particularly high.
The insect repellant in accordance with the invention exhibits together with its demonstrated synergistic effect furthermore a very low toxicity.
An embodiment by way of example of the insect repellant in accordance with the invention is given as follows:- EXAMPLE:
In order to produce a 12.5203 kg. repellant mixture in accordance with the invention, the following parts by weight were mixed together of the individual substances: 1kg phthalic acid diethyl ester, 1kg phthalic acid dibutyl ester, kg m-tolyl acid diethylamide, 0.02kg 2-phenyl cyclohexanol, kg 2 - ethyl - 1,3 - hexanediol, 1kg 2,2,4 -trimethyl - 1,3 - pentanediol, 0.0001kg lavender oil, 0.0001kg cedarwood oil, 0.0001kg oil of lemon, 3,75kg polyethylglycol 200 and 3.7kg 2-propanol.
This mixture has the demonstrated hereinbefore referred to repellant action is resistant to damp and sweat and has an acceptable smell.
Claims (9)
1. Insect repellantcontaining phthalic acid ester, 2 - phenyl - cyclohexanol and at least one further active substance, characterised by m-tolyl acid diethylamide as the further active substance.
2. Insect repellant according to claim 1, characterised in that the phthalic acid ester is incorporated as phthalic acid diethyl ester and/or phthalic acid dibutyl ester.
3. Insect repellant according to claim 2, characterised in this that the material phthalic acid diethyl ester, phthalic acid dibutyl ester, m-tolyl acid diethylamide and 2 - phenyl - cyclohexanol is incorporated in the proportions by weight 1:1:1:0.02.
4. Insect repellant according to one of the preced- ing claims, characterised in this that it contains as an additional active substance 2 - ethyl - 1,3 - hexanediol.
5. Insect repellant according to claim 4, characterised in this that the active substances phthalic acid diethyl ester, phthalic acid dibutyl ester, m-tolyl acid diethylamide, 2 - phenyl -cyclohexanol and 2 ethyl - 1,3 - hexanediol are incorporated in the proportions by weight 1:1:1:0.01:1.
6. Insect repellant according to one of the preceding claims, characterised in this that it includes as an additional active substance 2,2,4 -trimethyl - 1,3 pentanediol.
7. Insect repellant according to claim 6, characterised in this that the active substances phthalic acid diethyl ester, phthalic acid dibutyl ester, m-tolyl acid diethylamide, 2 - phenyl - cyclohexanol, 2 - ethyl - 1,3 - hexanediol and 2,2,4 -trimethyl - 1,3 - pentanediol are contained in the proportions by weight 1:1:1:0.02:1:1.
8. Insect repellant according to one of the preced- ing claims, characterised in this that it contains as an addition at least one etherial oil.
9. Insect repellant according to claim 8, characterised in this that it includes as the etherial oil lavender oil and/or cedarwood oil and/or oil of lemon.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2925589A DE2925589C2 (en) | 1979-06-25 | 1979-06-25 | Insect repellent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2054377A true GB2054377A (en) | 1981-02-18 |
| GB2054377B GB2054377B (en) | 1983-03-16 |
Family
ID=6074094
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8019578A Expired GB2054377B (en) | 1979-06-25 | 1980-06-16 | Insect repellant |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS568303A (en) |
| AT (1) | AT366882B (en) |
| BR (1) | BR8003939A (en) |
| DE (1) | DE2925589C2 (en) |
| FR (1) | FR2459616A1 (en) |
| GB (1) | GB2054377B (en) |
| IT (1) | IT1129017B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0090288A1 (en) * | 1982-03-30 | 1983-10-05 | Bayer Ag | Insect repellent |
| EP0097813A1 (en) * | 1982-06-03 | 1984-01-11 | Bayer Ag | Insect repellent |
| GB2183338A (en) * | 1985-11-19 | 1987-06-03 | Sclavo Spa | Self-mixing cell for photometric and turbidimetric measurements |
| US6646011B2 (en) | 1998-06-03 | 2003-11-11 | Johnson & Johnson Consumer Companies, Inc. | Insect repellant compositions |
| WO2007079822A1 (en) * | 2005-12-22 | 2007-07-19 | Merck Patent Gmbh | Insect repellent mixture |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3842232A1 (en) * | 1988-12-15 | 1990-06-21 | Silke Boehm | Insect repellent, in particular tick repellent |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2396013A (en) * | 1945-03-09 | 1946-03-05 | Howard A Jones | Insect repellent compositions |
-
1979
- 1979-06-25 DE DE2925589A patent/DE2925589C2/en not_active Expired
-
1980
- 1980-06-10 AT AT0304280A patent/AT366882B/en not_active IP Right Cessation
- 1980-06-16 GB GB8019578A patent/GB2054377B/en not_active Expired
- 1980-06-23 IT IT49037/80A patent/IT1129017B/en active
- 1980-06-24 BR BR8003939A patent/BR8003939A/en unknown
- 1980-06-24 JP JP8582280A patent/JPS568303A/en active Pending
- 1980-06-25 FR FR8014138A patent/FR2459616A1/en active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0090288A1 (en) * | 1982-03-30 | 1983-10-05 | Bayer Ag | Insect repellent |
| EP0097813A1 (en) * | 1982-06-03 | 1984-01-11 | Bayer Ag | Insect repellent |
| GB2183338A (en) * | 1985-11-19 | 1987-06-03 | Sclavo Spa | Self-mixing cell for photometric and turbidimetric measurements |
| US6646011B2 (en) | 1998-06-03 | 2003-11-11 | Johnson & Johnson Consumer Companies, Inc. | Insect repellant compositions |
| WO2007079822A1 (en) * | 2005-12-22 | 2007-07-19 | Merck Patent Gmbh | Insect repellent mixture |
Also Published As
| Publication number | Publication date |
|---|---|
| BR8003939A (en) | 1981-01-13 |
| IT8049037A0 (en) | 1980-06-23 |
| FR2459616A1 (en) | 1981-01-16 |
| DE2925589C2 (en) | 1982-10-14 |
| GB2054377B (en) | 1983-03-16 |
| DE2925589A1 (en) | 1981-01-08 |
| FR2459616B3 (en) | 1982-05-14 |
| JPS568303A (en) | 1981-01-28 |
| IT1129017B (en) | 1986-06-04 |
| AT366882B (en) | 1982-05-10 |
| ATA304280A (en) | 1981-10-15 |
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