GB2072013A - Louse-killing composition containing a pyrethroid - Google Patents
Louse-killing composition containing a pyrethroid Download PDFInfo
- Publication number
- GB2072013A GB2072013A GB8105466A GB8105466A GB2072013A GB 2072013 A GB2072013 A GB 2072013A GB 8105466 A GB8105466 A GB 8105466A GB 8105466 A GB8105466 A GB 8105466A GB 2072013 A GB2072013 A GB 2072013A
- Authority
- GB
- United Kingdom
- Prior art keywords
- composition according
- louse
- pyrethroid
- composition
- photostable
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 24
- 239000002728 pyrethroid Substances 0.000 title claims abstract description 7
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229960000490 permethrin Drugs 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims abstract description 8
- 239000003599 detergent Substances 0.000 claims abstract description 7
- 235000015112 vegetable and seed oil Nutrition 0.000 claims abstract description 7
- 239000008158 vegetable oil Substances 0.000 claims abstract description 7
- 239000012153 distilled water Substances 0.000 claims abstract description 6
- 230000002195 synergetic effect Effects 0.000 claims abstract description 6
- 125000002091 cationic group Chemical group 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 3
- DVBJBNKEBPCGSY-UHFFFAOYSA-M cetylpyridinium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 DVBJBNKEBPCGSY-UHFFFAOYSA-M 0.000 claims description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 235000019438 castor oil Nutrition 0.000 claims description 9
- 239000004359 castor oil Substances 0.000 claims description 9
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 9
- 239000003139 biocide Substances 0.000 claims description 7
- 239000013543 active substance Substances 0.000 claims description 3
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 claims description 2
- 239000007921 spray Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 239000003205 fragrance Substances 0.000 abstract 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 8
- 229960001777 castor oil Drugs 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 241001674048 Phthiraptera Species 0.000 description 6
- 238000003197 gene knockdown Methods 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- QAQSNXHKHKONNS-UHFFFAOYSA-N 1-ethyl-2-hydroxy-4-methyl-6-oxopyridine-3-carboxamide Chemical compound CCN1C(O)=C(C(N)=O)C(C)=CC1=O QAQSNXHKHKONNS-UHFFFAOYSA-N 0.000 description 2
- 241000517307 Pediculus humanus Species 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- -1 Lauryl Glycerin pyridinium monostearate Chemical compound 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241001581579 Mussa Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- VXSIXFKKSNGRRO-MXOVTSAMSA-N [(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1.CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VXSIXFKKSNGRRO-MXOVTSAMSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- OCLXJTCGWSSVOE-UHFFFAOYSA-N ethanol etoh Chemical compound CCO.CCO OCLXJTCGWSSVOE-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000000622 irritating effect Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 208000028454 lice infestation Diseases 0.000 description 1
- 229940032007 methylethyl ketone Drugs 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
-
- 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
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Epidemiology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Emergency Medicine (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cosmetics (AREA)
Abstract
A louse-killing composition of synergistic effect, contains 0.1-0.5% of photostable pyrethroid, preferably permethrin, dekamethrin and/or Fenvalerat, 0.2-10% vegetable oil(s) and/or 0.6- 60.0% cationic or non-ionic detergent(s) as synergising substances and 25-80% lower alkanol(s) as solvent, with, optionally 13-40% distilled water. An odouring substance fragrance may also be added.
Description
SPECIFICATION
Louse-killing composition or agent
The invention relates to a louse-killing agent or composition of synergistic effect. The agent or composition according to the invention is more effective than hitherto known agents and has no irritating effect on the skin.
Unfortunately, head-lice and crab-lice have recently become more and more widespread. Currently commercially available louse-killing agents (mostly in solution form e.g. "EGRO" and "NEOCIKLOTOX" manufactured by the firm BIOGAL, Debrecen, Hungary) have the disadvantage that they have to be removed after application, i.e. after rubbing in into the hair or the body, by washing or rinsing. By washing the hair or bathing the louse-killing effect also disappears and so persons who have been treated in this way may within a short time become lice-infested again.
The aim of the invention is to provide a louse-killing composition or agent which, in spite of containing the active substance or ingredient in a lower concentration, reliably and quickly kills the lice and nits (eggs of lice), possibly within minutes, and when applied to the head or hair or body hair or to clothing remains effective for a long period, does not irritate the skin and the eyes and does not need to be washed off after application.
As the active substance, compounds should be chosen which, in the range of concentration applied, are non-toxic and are not absorbed by the skin.
These requirements can be met with pyrethroids. Pyrethroids are synthetic analogues of pyrethrins, the insecticidal effect of which is known (see M. Elliott, N. F. Janes "Pyrethroids - A new class of insecticide",
Chem. Soc. Review, Vol. 7 Issue 4, (1978)).
It has now surprisingly been found that the insecticidal effect of the pyrethroids may considerably be increased when they are used in conjunction with vegetable oils and/or detergents.
The invention concerns a louse-killing agent. The agent according to the invention is characterised in that it contains 0.1-5.0% photostable pyrethroids and as a synergism-promoting substance 0.2 - 10.0% vegetable oils and/or 0.6% - 60% cationic or non-ionic detergents, further as organic solvents 25-80% lower alkanols, optionally 13-70% distilled water and, if so desired 0.1 - 1.0% odorising substances.
From amongst photostable pyrethroids, permethrin, Dekamethrin and Fenvalerat are particularly preferred. The agent according to the invention contains one or more pyrethroids in a concentration of 0.1 5.0%, preferably about 0.5%.
As synergising vegetable oil, castor oil is preferred and synergising detergent Sterogenol (Cetylpyridinium-bromide) is preferred. A particularly good effect is achieved by the simultaneous application of the two synergising substances although the individual components when used alone also have an appreciable effect.
To avoid allergy symptoms and irritation of the skin, the organic solvent and water content of the compounds according to the invention is fairly high. A combination of 96% ethanol, isopropanol and water in a ratio of about 54:25:13 has proved to be particularly effective. (The 96% ethanol mentioned in all subsequent Examples, formulations and substantive indications is Spiritus concentratissimus as defined by the Pharmacopoeia Hungarica Ph.Hg.VI)
The Sterogenol has in itself an insignificant insecticidal effect that has no influence on the effect of the compound according to the invention.
The synergistic effect of vegetable oils and detergents has been proved by a model experiment. Five different solutions were used of which, in addition to the solvents, the first solution contained castor oil and sterogenol, the second solution contained only permethrin, the third solution contained permethrin and castor oil, the fourth solution contained permethrin and sterogenol, and the fifth solution permethrin, castor oil and sterogenol. The composition of these solutions is given in the following Table:
Component Solution No.
1 2 3 4 5
Permethrin (g) - 0.5 0.5 0.5 0.5
Castoroil(g) 1.0 - 1.0 - 1.0
Sterogenol (g) 0.6 - - 0.6 0.6
Ethanol (96%) (ml) 59.4 61 60.0 55.0 54.0
Isopropanol (ml) 25.0 25.0 25.0 25.0 25.0
Distilled water (ml) 13.0 13.0 13.0 13.0 13.0
(Sterogenol is a commercially available 10% alcoholic solution of cetyl pyridinium-bromide).
Pieces of fabric, on which numerous nits of lice (Pediculus humanus vestimenti) have been laid, were then dipped into these solutions. Subsequently the pieces of cloth were dried at room temperature and incubated under thermostatic control at 30for eight days. Thereafter the total number of nits on each piece of cloth and the number of destroyed nits were ascertained by counting. (The nits are cask shaped and when the nits are destroyed the tops of the casks are not open). The degree of destruction is defined as the ratio of the nits destroyed to the total number of nits. The results are shown in Table I below:
Solution Total No.Number of Mortality
No. of nits destroyed nits
1 213 32 15.0
2 186 96 51.0
3 197 117 59.4
4 225 182 80.9
5 196 191 97.4
It can be seen from Table I that castor oil as well as sterogenol substantially improve the degree of destruction achievable by permethrin; the best result is, however, obtained if both synergistic substance are applied together.
As a result of tests carried out on live lice it has been established that the synergistic additives also increase the so called "knock-down" effect of the pyrethroids. The "knock-down" effect has been checked in the following way:
A solution of 0.1 mg and 0.0333 mg permethrin, respectively, prepared with 2 ml methyl-ethyl-ketone has been poured into a polished Petri dish with a diameter of 9.5 cm. Furthermore, Petri dishes containing, in addition to permethrin, sterogenol in various quantities were prepared. The following ratios of permethrin sterogenolweretested: 1:0.5; 1 :1; 1:2; 1 1:4; and 1:8.
Twenty female housefly (Mussa domestica) were set in each Petri-dish and the number of fly killed was determined every five minutes. The value KD50 was determined by graph illustrating the mortality. KD50 is the time required for killing half the fly. Each test was repeated twice. The results are shown in the following
Table:
TABLE II
Permethrin, mg KD50 values, with a
per Petri-dish Permethrin to Sterogenol ratio
1:0 1:0.5 1:1 1:2 1:4 1:8
0.1 10.2 7.7 6.8 8.3 9.4 10.7
0.0333 14.2 11.9 9.5 10.5 12.1 15.3
Table II shows that the time for KDSo was substantially shortened i.e. the "knock-down" effect appeared more quickly by adding sterogenol. With a ratio of 1:1 the reduction of the KD50 value is about 30%. The same test was carried out with Dekametrin in lieu of permethrin with similar results. This was all the more surprising since our own experiments proved that the low "knock-down" effect of pyromethrin could not be increased even if a second pyrethroid with good "knock-down" property was added.
The agent according to the invention was tested under real or actual conditions, i.e. on people living in a lice-infested environment. Through application of the louse-killing agent according to Example 1, immediate full freedom from lice was achieved. If the people treated with the agent according to Example 1 did not have a hair wash for a while after completion of the treatment, this freedom from lice was maintained for several weeks, although the treated persons continued to live in the lice-infested environment mentioned above.
The composition of the agent according to the invention is illustrated by the following non-limiting examples:
Example 1 Example 2 Example 3 permethrintechn. 0.5% Dekamethrin 4.0% Fenvalerat 1.0%
Castor oil 1.0% Peanut oil 10.0% Castor oil 5.0%
Sterogenol 0.6% Lauryl Glycerin
pyridinium monostearate 10.0%
sulphate 20.0%
Ethanol (96%) 54.4% Ethanol Ethanol (96%) 20.0%
(96%) 50.0%
Isopropanol 25.0% Isopropanol 25.0%
Distilled water 13.0% Water 15.0% Odouring compound 1.0%
Bodietta odouring Odouring Distilled water 38.0%
subst. 0.5% composition 1.0%
These preparations may be stored for two years, if kept in dark bottles and in a cool place. The preparations may be bottled in spray bottles.
Claims (12)
1. Louse-killing agent or composition of synergistic effect, comprising
(a) as active substance, 0.1-5.0 of photostable pyrethroid(s),
(b) as synergising substance, 0.2-10.0% of vegetable oil(s) and/or 0.6-60.0% of cationic or non-ionic
detergent(s),
(c) 25-80% of lower alkanol(s) and optionally 13-40% of distilled water, and, if desired, 0.1-1.0% of
odouring substance(s).
2. A composition according to claim 1 wherein the photostable pyrethroid is permethrin.
3. A composition according to claim 1 or 2 wherein the photostable pyrethroid is Dekametrin.
4. A composition according to any preceding claim wherein the amount of photostable pyrethroid is 0.3-0.6%.
5. Acomposition according to any preceding claim wherein it contains 0.5-2.0 castor oil as vegetable oil.
6. A composition according to any preceding claim wherein it contains 0.5-1.0% sterogenol as cationic detergent.
7. A composition according to any preceding claim wherein it contains ethanol and/or isopropanol as lower alkanol.
8. A composition according to any preceding claim wherein it contains as solvent a mixture of methyl alcohol (96%), isopropanol and water in a ratio of 2.0-3.0: 0.5-1.5: 0.1-0.5.
9. A composition according to any preceding claim wherein it is bottled in spray bottles.
10. The use of a louse-killing agent or composition according to any preceding claim, wherein the agent or composition is brought into action on lice-infested organisms.
11. The use of a louse-killing agent or composition according to any of claims 1 - 9 wherein the agent or composition its action is exerted on lice-infested articles of clothing.
12. A composition according to claim 1 substantially as herein described in any one of the Examples.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU80430A HU182802B (en) | 1980-02-26 | 1980-02-26 | Fotostabil delousing (insecticide) composition containing synthetic piretroides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2072013A true GB2072013A (en) | 1981-09-30 |
| GB2072013B GB2072013B (en) | 1984-11-07 |
Family
ID=10949564
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8105466A Expired GB2072013B (en) | 1980-02-26 | 1981-02-20 | Louse-killing composition containing a pyrethroid |
Country Status (12)
| Country | Link |
|---|---|
| AT (1) | AT372244B (en) |
| BE (1) | BE887600A (en) |
| CH (1) | CH647650A5 (en) |
| CS (1) | CS226422B2 (en) |
| DD (1) | DD156511A5 (en) |
| DE (1) | DE3107129A1 (en) |
| FR (1) | FR2476486A1 (en) |
| GB (1) | GB2072013B (en) |
| HU (1) | HU182802B (en) |
| NL (1) | NL8100876A (en) |
| PL (1) | PL125709B1 (en) |
| RO (1) | RO81516B (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0088919A1 (en) * | 1982-03-09 | 1983-09-21 | Bayer Ag | Pesticidal pour-on formulations |
| JPS58162502A (en) * | 1982-03-09 | 1983-09-27 | バイエル・アクチエンゲゼルシヤフト | Insecticidal compositions |
| GB2137089A (en) * | 1983-03-31 | 1984-10-03 | T & R Chemicals Inc | Pyrethroid-containing pharmaceutical compositions |
| EP0262885A2 (en) * | 1986-09-29 | 1988-04-06 | Del Laboratories Incorporated | Pediculicidal/ovicidal shampoo composition |
| US6395776B1 (en) * | 1995-08-03 | 2002-05-28 | Bayer Aktiengesellschaft | Pesticides |
| CN115968876A (en) * | 2023-01-12 | 2023-04-18 | 中山榄菊日化实业有限公司 | Long-acting insecticidal ultra-low volume liquid and preparation method thereof |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB660131A (en) * | 1947-09-18 | 1951-10-31 | Mckesson & Robbins Inc | Parasiticidal lotions |
| US3492402A (en) * | 1967-02-01 | 1970-01-27 | Mclaughlin Gormley King Co | Pyrethroid insecticidal compositions containing an emulsifier and a bacterio-fungistat |
| US3864388A (en) * | 1970-12-29 | 1975-02-04 | Sumitomo Chemical Co | Alkynyl esters of {60 -alkoxy-{60 -phenyl alkenoic acid |
| GB1511646A (en) * | 1974-05-08 | 1978-05-24 | Wellcome Found | Method for insecticide use |
| US3966959A (en) * | 1975-02-13 | 1976-06-29 | American Cyanamid Company | Insecticidal and acaricidal, pyrethroid compounds |
| FR2341307A1 (en) * | 1976-02-19 | 1977-09-16 | Roussel Uclaf | PYRETHRINOIDS FOR MEDICINAL PRODUCTS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| GB1574609A (en) * | 1976-07-06 | 1980-09-10 | Inchcape Chemco Ltd | Pesticidal compositions |
| SE446527B (en) * | 1976-09-21 | 1986-09-22 | Roussel Uclaf | NEW CYCLOPROPANCARBOXYLIC ACID ESTERS WITH A POLYHALOGENATED SUBSTITUENT, SET FOR PREPARATION OF IT AND USE thereof IN PESTICIDE COMPOSITIONS |
| GB1591105A (en) * | 1976-12-24 | 1981-06-17 | Wellcome Found | Pest control |
| GB1591106A (en) * | 1976-12-24 | 1981-06-17 | Wellcome Found | Pest control |
| FR2377198A2 (en) * | 1977-01-13 | 1978-08-11 | Roussel Uclaf | Compsns. for topical treatment of cattle scabies - contg. an ester of 2,2-di:methyl 3-substd. vinyl cyclopropane carboxylic acid |
| DE2704066A1 (en) * | 1977-02-01 | 1978-08-03 | Neudorff & Co Chem Fab W | Insecticidal combinations of permethrin and pyrethroid(s) - for general use, having fast activity |
| GB1602971A (en) * | 1977-03-11 | 1981-11-18 | Wellcome Found | Synergistic pesticidal compositions |
| GB2012585B (en) * | 1977-12-20 | 1982-04-15 | Ici Ltd | Insecticidal formulations |
| GB2021416A (en) * | 1978-05-16 | 1979-12-05 | Wellcome Found | Pest control |
| EP0006630A1 (en) * | 1978-07-03 | 1980-01-09 | Ciba-Geigy Ag | Alpha-phenyl-alpha-cyclopropane acetic acid esters, process for their preparation and their use as insecticides |
| DE2844271A1 (en) * | 1978-10-11 | 1980-04-24 | Bayer Ag | 3-CHLOROSTYRYL-2,2-DIMETHYL-CYCLOPROPANCARBONIC ACID (4-FLUORO-3-PHENOXY-ALPHA-CYANO-BENZYL) -ESTER, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS EECTOPARASITICIDES |
| FR2484256B1 (en) * | 1979-06-29 | 1986-10-24 | Roussel Uclaf | METHOD FOR CONTROLLING PEST OF HOT BLOOD ANIMALS |
| IT1123122B (en) * | 1979-09-12 | 1986-04-30 | Montedison Spa | INSECTICIDE LIQUID COMPOSITIONS CONTAINING SYNTHETIC PYRETROIDS |
-
1980
- 1980-02-26 HU HU80430A patent/HU182802B/en unknown
-
1981
- 1981-02-18 AT AT0073481A patent/AT372244B/en not_active IP Right Cessation
- 1981-02-20 GB GB8105466A patent/GB2072013B/en not_active Expired
- 1981-02-20 BE BE1/10146A patent/BE887600A/en not_active IP Right Cessation
- 1981-02-20 FR FR8103379A patent/FR2476486A1/en active Granted
- 1981-02-23 NL NL8100876A patent/NL8100876A/en not_active Application Discontinuation
- 1981-02-24 DD DD81227835A patent/DD156511A5/en not_active IP Right Cessation
- 1981-02-24 PL PL1981229837A patent/PL125709B1/en unknown
- 1981-02-25 RO RO103518A patent/RO81516B/en unknown
- 1981-02-25 CH CH1259/81A patent/CH647650A5/en unknown
- 1981-02-25 CS CS811351A patent/CS226422B2/en unknown
- 1981-02-26 DE DE19813107129 patent/DE3107129A1/en not_active Withdrawn
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0088919A1 (en) * | 1982-03-09 | 1983-09-21 | Bayer Ag | Pesticidal pour-on formulations |
| JPS58162503A (en) * | 1982-03-09 | 1983-09-27 | バイエル・アクチエンゲゼルシヤフト | Pour-on insecticidal compositions |
| JPS58162502A (en) * | 1982-03-09 | 1983-09-27 | バイエル・アクチエンゲゼルシヤフト | Insecticidal compositions |
| JPH0524121B2 (en) * | 1982-03-09 | 1993-04-06 | Bayer Ag | |
| US4675313A (en) * | 1983-03-31 | 1987-06-23 | T & R Chemicals, Inc. | Pyrethroid-containing pharmaceutical compositions |
| EP0121363A3 (en) * | 1983-03-31 | 1985-04-10 | T And R Chemicals, Inc. | Pyrethroid-containing pharmaceutical compositions |
| EP0121363A2 (en) * | 1983-03-31 | 1984-10-10 | T And R Chemicals, Inc. | Pyrethroid-containing pharmaceutical compositions |
| US4701446A (en) * | 1983-03-31 | 1987-10-20 | T & R Chemicals, Inc. | Pyrethroid containing pharmaceutical compositions |
| GB2137089A (en) * | 1983-03-31 | 1984-10-03 | T & R Chemicals Inc | Pyrethroid-containing pharmaceutical compositions |
| EP0262885A2 (en) * | 1986-09-29 | 1988-04-06 | Del Laboratories Incorporated | Pediculicidal/ovicidal shampoo composition |
| EP0262885A3 (en) * | 1986-09-29 | 1990-06-27 | Del Laboratories Incorporated | Pediculicidal/ovicidal shampoo composition |
| US6395776B1 (en) * | 1995-08-03 | 2002-05-28 | Bayer Aktiengesellschaft | Pesticides |
| CN115968876A (en) * | 2023-01-12 | 2023-04-18 | 中山榄菊日化实业有限公司 | Long-acting insecticidal ultra-low volume liquid and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2476486B1 (en) | 1984-11-23 |
| CH647650A5 (en) | 1985-02-15 |
| BE887600A (en) | 1981-08-20 |
| GB2072013B (en) | 1984-11-07 |
| DD156511A5 (en) | 1982-09-01 |
| CS226422B2 (en) | 1984-03-19 |
| DE3107129A1 (en) | 1981-12-24 |
| FR2476486A1 (en) | 1981-08-28 |
| AT372244B (en) | 1983-09-12 |
| PL125709B1 (en) | 1983-06-30 |
| NL8100876A (en) | 1981-09-16 |
| HU182802B (en) | 1984-03-28 |
| ATA73481A (en) | 1983-02-15 |
| PL229837A1 (en) | 1981-11-13 |
| RO81516A (en) | 1983-04-29 |
| RO81516B (en) | 1983-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19950220 |