GB2282534A - Insect repellent compositions - Google Patents
Insect repellent compositions Download PDFInfo
- Publication number
- GB2282534A GB2282534A GB9320776A GB9320776A GB2282534A GB 2282534 A GB2282534 A GB 2282534A GB 9320776 A GB9320776 A GB 9320776A GB 9320776 A GB9320776 A GB 9320776A GB 2282534 A GB2282534 A GB 2282534A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cis
- diol
- trans
- insect repellent
- menthane
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 37
- 239000000077 insect repellent Substances 0.000 title claims abstract description 18
- LMXFTMYMHGYJEI-UHFFFAOYSA-N p-menthane-3,8-diol Chemical class CC1CCC(C(C)(C)O)C(O)C1 LMXFTMYMHGYJEI-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229930006948 p-menthane-3,8-diol Natural products 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 241000255925 Diptera Species 0.000 claims description 7
- 241000238631 Hexapoda Species 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 5
- 239000000443 aerosol Substances 0.000 claims description 3
- 239000006210 lotion Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000007921 spray Substances 0.000 claims description 3
- 150000002009 diols Chemical class 0.000 claims description 2
- -1 roll-on Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001846 repelling effect Effects 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 11
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 4
- 210000000245 forearm Anatomy 0.000 description 4
- 239000000463 material Substances 0.000 description 3
- 239000005871 repellent Substances 0.000 description 3
- 230000002940 repellent Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 2
- 230000002045 lasting effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000013598 vector Substances 0.000 description 2
- 241000256111 Aedes <genus> Species 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 241000256113 Culicidae Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 1
- 244000166124 Eucalyptus globulus Species 0.000 description 1
- 208000004554 Leishmaniasis Diseases 0.000 description 1
- 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 1
- 241000255129 Phlebotominae Species 0.000 description 1
- 241000722350 Phlebotomus <genus> Species 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 206010042618 Surgical procedure repeated Diseases 0.000 description 1
- 208000003152 Yellow Fever Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000010632 citronella oil Substances 0.000 description 1
- 229930003633 citronellal Natural products 0.000 description 1
- 235000000983 citronellal Nutrition 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000007682 dermal toxicity Effects 0.000 description 1
- 229960001673 diethyltoluamide Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000010642 eucalyptus oil Substances 0.000 description 1
- 229940044949 eucalyptus oil Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000013020 final formulation Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000012678 infectious agent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000013383 initial experiment Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 231100000438 skin toxicity Toxicity 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000440 toxicity profile Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/06—Oxygen or sulfur directly attached to a cycloaliphatic 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)
Abstract
An insect repellent composition contains one or both isomers of p-menthane-3,8-diol which has been extracted from a natural oil or synthesised chemically, and a carrier.
Description
INSECT REPELLENT COMPOSITIONS
This invention relates to insect repellent compositions.
Diethyl toluamide is a widely used insect repellent. There are also a number of natural products which show insect repellency to a greater or lesser degree.
Among these is citronella oil which is obtained from certain grasses. Also, certain species of Eucalyptus contain a natural product in their leaves which displays insect repellent properties.
We have made an investigation of these naturally occurring products to try to isolate and identify the active material which gives rise to the insect repellent properties. After considerable work, we have found that the active material is p-menthane-3,8-diol. The material can be extracted and purified from its naturally occurring sources.
Alternatively, it can be synthesised chemically as described, for example, by Zimmerman and English in J.A.C.S.
75 (1953) pp 2367-2370.
In one aspect, the present invention provides an insect repellent composition which comprises p-menthane-3,8diol and a physiologically acceptable carrier therefor, the said diol having been extracted from a natural oil or having been synthesised chemically.
It is to be understood that the invention does not extend to the use, as an insect repellent, of the p-menthane -3,8-diol containing natural oils themselves. Rather, in the compositions of the invention, any naturally occurring p-menthane-3,8-diol (hereinafter abbreviated to '1PMD") has been extracted from a natural source and thus has been at least partly separated from other substances in admixture with which it naturally occurs. The PMD can be very pure or it can still contain other materials from its source.
We have further investigated PMD and its insect repellency properties (particularly towards mosquitoes).
PMD can exist in two geometric isomeric forms, namely the cis and the trans isomers. We have separated PMD into its component isomers and have tested each, and mixtures, to determine their insect repellent properties. We have found that the isomers display different insect repellent properties and, in particular, that the trans isomer initially has the better repellency, whereas the cis isomer has a longer lasting effect.
According to a further aspect of the invention, there is provided an insect repellent composition which comprises only one of the isomers of PMD, with a carrier therefor.
In accordance with a highly preferred feature of the invention, the relative quantities of cis and trans PMD isomers can be adjusted to provide the desired effect. For example, for high repellency immediately after application, the ratio cis:trans should be low (i.e. there is more trans than cis). For a long lasting effect, however, the cis:trans ratio should be high (more cis than trans).
The invention thus includes an insect repellent composition comprising a mixture of the cis and trans isomers of PDG, wherein the cis:trans ratio has been chosen to provide the desired insect repellency property.
These compositions can be made by mixing previously separated PDG isomers in the appropriate ratio, or by adjusting the ratio in a mixture of naturally occurring or synthetic source.
We have found that, for general purposes, the range of cis:trans ratios will be (by weight) from about 1.5:1 to about 6:1. The best range is from about 2:1 to about 3:1, with 2.5:1 being most preferred.
The invention thus includes an insect repellent composition which comprises the cis and trans isomers of PDG in a weight of cis:trans from 2:1 to 3:1, with a carrier therefor.
The compositions of the invention have been described above comprising a carrier. It is to be understood that the invention also encompasses the use of
PDG and of its isomers (individually or in admixture) for insect repellency purposes with or without a carrier.
For normal use, the compositions of the invention will be formulated as sprayable liquids (e.g. solutions of
PDG in suitable solvents such as alcohols), pressurised aerosols, lotions, creams, roll-ons or solid sticks, although other formulations can of course be used. It will be well understood by those skilled in the art as to how these formulations are made.
In order that the invention can be more fully understood, the following Examples are given by way of illustration only.
Examnle 1
Separation of the isomers of PMD
PMD was synthesised as described in the literature from citronellal by reaction with 5% sulphuric acid. The product was chromatographed on a silica gel column, eluting with 9:1 cyclohexane-ethyl acetate (200ml), then with an equal amount of 4:1 of the same mixture. Evaporation of the appropriate fractions (as determined by thin layer chromatography) yielded two products. 13 CNMR spectrum of the fractions confirmed them as the pure cis and trans isomers of p-menthane-3.8-diol along with a little cyclohexane (the chromatography solvent). The physical properties of these isomers were: 1. Colourless, very viscous, glycerol-like liquid
with a faint citrus odour 2. Limited solubility in water but miscible with
ethanol, ether and (warm) petrol solvents 3.Boiling point between 129-142"C at 5mm Hg 4. Density less than 1 5. Not light sensitive and temperature stability is
high.
The chemical structures were:
trans cis
C1S Example 2 Repellency Tests
In order to establish the most efficient mix of isomers for final formulation, we undertook repellency testing using human volunteers and live hungry female mosquitos.
Test Procedure
Both right and left forearms of human volunteers were washed with 2ml of industrial alcohol. The right forearm was used as a control and the left forearm for testing. An assistant wearing a fresh pair of rubber gloves on each occasion applied the test material to the left forearm in the quantity described. The control arm was first introduced into a cage of hungry, mainly female mosquitoes. The number of mosquitoes probing at 45 seconds was counted. The mosquitoes were then shaken off and the arm withdrawn (the mosquitoes did not have sufficient time to actually feed and become satiated). The test arm was then introduced and the procedure repeated. The test arm was evaluated every hour for the test period and the control arm was retested at the end of the period to confirm that biting drive remained high.
We undertook the following experiments to compare the efficacy and longevity of each of the isomers: 1. Minimum effective dose
After initial control readings on both untreated
arms, 0.04 ml of a 17.9% solution of the pure cis
isomer in ethanol was applied and tested.
Incremental increases were applied until total
repellency was achieved. Hourly testing was then
carried out to measure the decay of repellent
action. The same procedure was followed with a
7.4% solution of the trans isomer.
Results:
The total dose of cis isomer required to just
achieve full repellency was 0.12ml of 17.9%
solution or 21.5mg. Repellency was 50% at 1 hour
and 11% at 2 hours. The total dose of trans
isomer required to just achieve full repellency
was 0.3ml of 7.4% solution or 22.2mg. Repellency
was lost after 1 hour.
2. LonRevitv of action
We took equal quantities of the cis and trans
isomers being 0.75ml of 17.9% cis in ethanol and 1.8ml of 7.4% trans in ethanol. giving the
equivalent of 130mg of each isomer for each test.
This was considered to be the appropriate amount
that would be applied in practice by an individual
wishing to apply repellent for protection.
Results:
Time % Repellencv against control Control no. of bites (hrs) Cis Trans Cis Trans
0 91.3 97.1 30 34
1 91.3 76.5
2 85.5 70.6
3 76.8 41.2
4 56.5 29.7 39 38
From these results, it can be seen that although the cis isomer had some initial repellency, the trans isomer was even better. The cis clearly outlasted the trans, however, in longevity of action.
We therefore concluded that a cis:trans ratio in the region of between 2:1 and 3:1 would prove the best repellent for practical use, combining high initial efficacy with the longest lasting action.
ODtimum Concentration Formulation
Having decided upon the best cis:trans ratio, we looked at the highest concentration of active ingredient that could be achieved in a practical preparation. Encouraged by the lack of any evidence of dermal toxicity in an initial experiment and with the known safe toxicity profile of Eucalyptus oil derivatives over many years, we felt that a high concentration was achievable. Because of the physical properties and requirements for dispersal as a spray, we felt that a 50% solution in ethanol should be tested.
We proceeded to test the efficacy of this 50% concentrate of a 2.5:1 cis:trans mixture of p-menthane-3,8diol in alcohol. We tested against 2 different strains of mosquito, (AnoDheles stephensi and Aedes aegyDti) noted for their different biting patterns vectors respectively of the infectious agents of malaria and yellow fever, and against the sandfly (Phlebotomus Sod. ) vectors of Leishmaniasis infection. We achieved 100% repellency against all types for at least 6 hours and in some cases 8 hours.
Example 3
As previously stated, our tests have used a 50% concentration of the 2.5:1 cis:trans mixture in ethanol for pump spray application. This same mixture is effective in butane pressurised aerosols, lotions, roll-ons, solid sticks, gels etc.
Claims (11)
1. An insect repellent composition which comprises pmenthane-3,8-diol and a carrier therefor, the said diol having been extracted from a natural oil or having been synthesised chemically.
2. An insect repellent composition which comprises only one of the isomers of p-menthane-3,8-diol.
3. An insect repellent composition which comprises a mixture of the cis and trans isomers of p-menthane-3,8-diol, the cis:trans ratio having been chosen to provide the desired insect repellency property.
4. A method of making an insect repellent composition which comprises providing a mixture of the cis and trans isomers of p-menthane-3,8-diol in a ratio predetermined to provide the desired insect repellency property.
5. A composition according to claim 1 or 3 wherein the cis:trans ratio is from 2:1 to 3:1 by weight.
6. A composition according to any of claims 1,2,3 or 5, which comprises an alcohol as a carrier for the p menthane-3 , 8-diol.
7. A composition according to claim 6, wherein the pmenthane-3,8-diol is in solution in ethanol.
8. A composition according to claim 7, wherein the solution is 50% by weight p-menthane-3,8-diol.
9. A composition according to claim 6,7 or 8, which is in a spray container.
10. A formulation of a composition as claimed in any of claims 1,2,3 or 5 to 8, in the form of a sprayable solution, an aerosol, a lotion, roll-on, solid stick or gel.
11. A formulation according to claim 10 for repelling mosquitoes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9320776A GB2282534A (en) | 1993-10-08 | 1993-10-08 | Insect repellent compositions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9320776A GB2282534A (en) | 1993-10-08 | 1993-10-08 | Insect repellent compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB9320776D0 GB9320776D0 (en) | 1993-12-01 |
| GB2282534A true GB2282534A (en) | 1995-04-12 |
Family
ID=10743224
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9320776A Withdrawn GB2282534A (en) | 1993-10-08 | 1993-10-08 | Insect repellent compositions |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2282534A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001005226A1 (en) * | 1999-07-21 | 2001-01-25 | Paul Douglas Clarke | Antiseptic composition |
| WO2005087209A1 (en) * | 2004-03-12 | 2005-09-22 | Paul Douglas Clarke | Antiviral composition comprising p-menthane-3, 8-diol |
| US7189421B2 (en) | 1999-07-21 | 2007-03-13 | Paul Douglas Clarke | Antiseptic composition |
| WO2009034352A1 (en) * | 2007-09-13 | 2009-03-19 | Ian Thomas Dell | Composition containing p-menthane-3, 8-diol and its use as insect repellent |
| US20130136704A1 (en) * | 2011-11-28 | 2013-05-30 | Takasago International Corporation | P-menthane-3,8-diol isomer mixture, composition comprising the same, and products comprising the mixture or composition |
| WO2024252135A1 (en) | 2023-06-08 | 2024-12-12 | University Of Leicester | Methods and compounds |
| EP4646930A1 (en) * | 2024-05-10 | 2025-11-12 | Glycoscience, S.L. | Long-duration formulation |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60199804A (en) * | 1984-03-26 | 1985-10-09 | Nippon Kayaku Co Ltd | Repellent for injurious organism |
| EP0367140A2 (en) * | 1988-10-31 | 1990-05-09 | Takiron Co. Ltd. | Controlled release insect pest repellent |
| WO1992002136A1 (en) * | 1990-08-06 | 1992-02-20 | R & C Products Pty. Limited | Insect repellent |
| JPH04352703A (en) * | 1991-05-28 | 1992-12-07 | Nippon Kayaku Co Ltd | Insect pest repellent microcapsule agent containing p-menthane derivative |
-
1993
- 1993-10-08 GB GB9320776A patent/GB2282534A/en not_active Withdrawn
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60199804A (en) * | 1984-03-26 | 1985-10-09 | Nippon Kayaku Co Ltd | Repellent for injurious organism |
| EP0367140A2 (en) * | 1988-10-31 | 1990-05-09 | Takiron Co. Ltd. | Controlled release insect pest repellent |
| WO1992002136A1 (en) * | 1990-08-06 | 1992-02-20 | R & C Products Pty. Limited | Insect repellent |
| JPH04352703A (en) * | 1991-05-28 | 1992-12-07 | Nippon Kayaku Co Ltd | Insect pest repellent microcapsule agent containing p-menthane derivative |
Non-Patent Citations (4)
| Title |
|---|
| Chemical Abstract 118(17):163281m & JP 04 352 703 A * |
| Chemical Abstracts 104(11): 83820g & JP 60 199 804 A * |
| Chemical Abstracts 108(25): 217808c & CN 86 105 233 A * |
| Chemical Abstracts 115(21):226183s & JP 3 133 906 A * |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001005226A1 (en) * | 1999-07-21 | 2001-01-25 | Paul Douglas Clarke | Antiseptic composition |
| AU773700B2 (en) * | 1999-07-21 | 2004-06-03 | Paul Douglas Clarke | Antiseptic composition |
| US7189421B2 (en) | 1999-07-21 | 2007-03-13 | Paul Douglas Clarke | Antiseptic composition |
| WO2005087209A1 (en) * | 2004-03-12 | 2005-09-22 | Paul Douglas Clarke | Antiviral composition comprising p-menthane-3, 8-diol |
| US7872051B2 (en) | 2004-03-12 | 2011-01-18 | Paul Douglas Clarke | Antiviral composition comprising p-menthane-3,8-diol |
| WO2009034352A1 (en) * | 2007-09-13 | 2009-03-19 | Ian Thomas Dell | Composition containing p-menthane-3, 8-diol and its use as insect repellent |
| US10391045B2 (en) | 2007-09-13 | 2019-08-27 | Ian Thomas Dell | Composition containing p-menthane-3, 8-diol and its use as insect repellant |
| US20130136704A1 (en) * | 2011-11-28 | 2013-05-30 | Takasago International Corporation | P-menthane-3,8-diol isomer mixture, composition comprising the same, and products comprising the mixture or composition |
| WO2024252135A1 (en) | 2023-06-08 | 2024-12-12 | University Of Leicester | Methods and compounds |
| EP4646930A1 (en) * | 2024-05-10 | 2025-11-12 | Glycoscience, S.L. | Long-duration formulation |
| WO2025233177A1 (en) * | 2024-05-10 | 2025-11-13 | Glycoscience, S.L. | Long-duration formulation |
Also Published As
| Publication number | Publication date |
|---|---|
| GB9320776D0 (en) | 1993-12-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |