GB2052988A - Compositions for the control of parasites in warm-blooded animals - Google Patents
Compositions for the control of parasites in warm-blooded animals Download PDFInfo
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- GB2052988A GB2052988A GB8021250A GB8021250A GB2052988A GB 2052988 A GB2052988 A GB 2052988A GB 8021250 A GB8021250 A GB 8021250A GB 8021250 A GB8021250 A GB 8021250A GB 2052988 A GB2052988 A GB 2052988A
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- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
-
- 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
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Emergency Medicine (AREA)
- Plant Pathology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Dermatology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Compositions adapted for administration to a portion of the surface of the body of a warm-blooded animal comprise, as active ingredient, at least one compound of formula I <IMAGE> wherein X1 represents a hydrogen, fluorine, chlorine or bromine atom; X2 represents a fluorine, chlorine or bromine atom, X3 represents a chlorine, bromine or iodine atom and R represents a benzyl radical (optionally substituted by one or more substituents from C1-4 alkyl radicals, C2-6 alkenyl radicals, C2-6 alkenyloxy radicals, C4-8 alkadienyl radicals, methylenedioxy radicals, benzyl radicals and halogen atoms); a group of formula: <IMAGE> a group of formula: <IMAGE> or a group of formula: <IMAGE> or a group of formula: <IMAGE> (in which the symbol S/I indicates an aromatic ring or dihydro or tetrahydro analogue thereof); said active ingredient being in association with a vehicle capable of permitting passage of the active ingredient through the skin barrier of the animal, R1-R9 being defined as in Claim 1.
Description
SPECIFICATION
Compositions for the control of parasites in warm-blooded animals
This invention relates to new compositions adapted for administration to a portion of the surface of the body of warm-blooded animals for controlling parasites on the said animals as well as to methods of using such compositions.
The compounds of general formula I,
wherein
X1 represents a hydrogen, fluorine, chlorine or bromine atom;
X2 represents a fluorine, chlorine or bromine atom;
X3 represents a chlorine, bromine or iodine atom; and
R represents a benzyl radical (optionally substituted by one or more substituents selected from
C1-4 alkyl radicals, C2-6 alkenyl radicals, C2-6 alkenyloxy radicals, C4-8 alkedienyl radicals, methylenedioxy radicals, benzyl radicals and halogen atoms); a group of formula:
(in which R1 represents a hydrogen atom or a methyl radical and R2 represents a monocyclic aryl group or a group of formula -CH2-C=-CH), especially a 5-benzyl-3-furylmethyl group; a group of formula:
(in which R3 represents an organic C28 aliphatic radical containing one or more carbon-carbon unsaturations, especially a vinyl, propen-1-yl, buta-1,3-dienyl or buten-1-yl radical); a group of formula:
(in which R4 represents a hydrogen atom or a group of formula -C=N or -C=-CH, R5 represents a chlorine atom or a methyl radical and n is O, 1 or 2), especially a 3-phenoxybenzyl, a-cyano-3phenoxybenzyl or a-ethynyl-3-phenoxybenzyl group; or a group of formula:
(in which R6, R7, R8 and R9, which may be the same or different, each represents a hydrogen atom, a chlorine atom or a methyl radical and the symbol S/I indicates an aromatic ring or a dihydro or tetrahydro analogue thereof), are known products which can be prepared according to the processes described in British Patent Specifications Nos. 1,561,469 and 2,016,447 (New Zealand Patent Specification Nos. 185,226 and 189,552).
The compounds of general formula I, which may be present in one or more isomeric forms as well as mixtures, thereof, show remarkable pesticidal properties and especially excellent insecticidal, acaricidal, nematocidal and fungicidal properties.
Hitherto the methods of administration known for the compounds of formula I in their use to control parasites of warm-blooded animals were methods of administration by digestive, parenteral or topical routes and consequently only the corresponding compositions were known.
We have now found that it is possible to obtain excellent results in the control of parasites on warm-blooded animals by administering these compounds of general formula I according to a method known as the "pour on" method which consists of painting a small surface, and preferably the backbone, of the body of the animal with a solution containing the active product whereby the active product is caused to pass into the general circulation system of the animal and thus obtain an effect over the whole body of the animal. The painting can also be carried out on the ears of the animal.
That this method would be suitable and indeed advantageous for the compounds of general formula I could not have been predicted since this method is of course not generally applicable to any active product by can be applied only to chemical compounds capable of passing through the skin barrier and of entering into the general circulation system whilst either keeping their activity, that is to say without being degraded, or of being degraded into metabolites which are themselves active. Nothing in the prior art suggests the use of the compounds of general formula I in such a method.
According to one feature of the present invention there are provided compositions adapted for administration to a portion of the surface of the body of a warm-blooded animal comprising, as active ingredient, at least one compound of formula I as hereinbefore defined said active ingredient being in association with a vehicle capable of permitting passage of the active ingredient through the skin barrier of the animal.
According to a further feature of the present invention there is provided a method of treating or preventing an infestation by parasites of a warm-blooded animal which comprises applying to a portion of the surface of the said animal a composition as hereinbefore defined containing at least one compound of formula
As described above the compositions according to the invention can be applied to animals by the "pour on" method and thus, due to this unexpected finding, such compositions are of great interest industrially as they enable excellent pesticidal results to be obtained very quickly and in a lasting manner using very small amounts of the compounds of general formula I.
The compositions according to the invention permit simple, clean and economic application of the compounds of general formula I, showing a number of advantages over the hitherto known compositions for administration by other methods. Thus, whilst administration by the digestive route gives good results, it must be discarded if possible for it can cause gastric disorders and must be reserved particularly for the control of parasites located in the stomach.
Administration by the use of baths also gives quite good results. Unfortunately, however, it requires a fairly large amount of active product and, particularly in the case of pyrethrinoids it is necessary to renew the bath often since these compounds, generally speaking, are easily degraded.
Administration by the parenteral route is to be avoided wherever possible, since it is not easy to inject all the animals of a group.
The compositions according to the invention, however, may easily and quickly be painted on a portion of the body surface of the animal. They can be applied to all warm-blooded animals and especially stock animals such as, for example, cattle, sheep or pigs.
The compositions according to the invention enable parasites to be combatted, whether they be internal or external parasites. They permit especially the control of acarids e.g. ticks and scabies, helminths, warble maggots and various kinds of stinging flies.
Among the compositions according to the invention, preferred compositions are those which contain at least one compound corresponding to the formula IA
(in which X represents a chlorine or bromine atom) in one or more of its possible isomeric forms and among these latter, may be mentioned (S) a-cyano-3-phenoxybenzyl (1 R, cis)-2,2-dimethyl3-(2, 2-dichloro- 1, 2-dibromoethyl)-cyclopropane-1 -carboxylate (denoted hereinafter product A) and (S) a-cyano-3-phenoxybenzyl (1 R, cis)-2,2-dimethyl-3-(1 ,2,2,2-tetrabromo-ethyl)-cyclopro- pane-1-carboxylate. The preparation of these compounds of formula 1A is described in British
Patent Specification No. 1,561,469 in Examples 1 and 2.
The amount of active product of formula I to be applied to the animal will vary depending upon the condition of the animal to be treated, the species, the environment as well as result sought. In general, however it will be desirable to administer from 0.5 to 10 mg of the compound of formula I per kg of bodyweight of the treated animal. The number of treatments which should be carried out will also vary depending upon the same parameters as those which have been set out above to determine the amount of product to be administered. As illustrated hereinafter, however, excellent results may be obtained with a single application.
The compositions according to the invention contain a vehicle permitting passage of the active ingredient through the skin barrier. Particular vehicles which may be mentioned are solutions, preferably oily solutions, of a dispersing agent, such as, for example, dimethylformamide, dimethylsulphoxide or dimethylacetamide as well as other dispersing agents known in the pharmaceutical industry to facilitate passage through the skin barrier, insofar as the solubility of the compounds of general formula I in these agents permits it. The oily solutions used preferably contain a vegetable oil such as e.g. olive or ground-nut oil.
A particularly preferred vehicle for the compositions according to the invention is an oily solution of dimethylformamide.
The compositions according to the invention may, if desired, include an emulsifying agent and/or a surface-active agent.
The use and activity of the compositions according to the invention may be illustrated as follows:
Test 1: Test on "Boophilus microplus"
A young bull weighing 340 kg is infected deliberately with ticks of the species Boophilus microplus.
The ticks are in all stages of development. The backbone of the animal is painted on day D with a solution containing 5 mg of product A per kg of body-weight of the treated animal in a mixture of dimethylformamide and olive oil (1:1). 1.7 g of product A in 80 ml of oily solution are thus used.
The ticks are counted and the stages of development are observed:
Days before and after treatment
D-2 D-1 D D+1 D+2 D+3 D+4
Number of ticks 16 21 71 13 13 0 0 % inhibition of O 0 0 38 23 - - the laying of eggs
Stage of All stages of Some ticks All the development. development are alive ticks are
are found. but others dead
are dead
Conclusion: Product A shows remarkable activity.
Test 2: Test on Boophilus microplus, strain Mexico
Young bulls infected deliberately with "Boophilus microplus" ticks are used. A control bath does not receive any treatment.
One batch is painted on day D with 100 cm3 of a solution identical to that used in Test 1 containing 5 mg of product A per kg of weight of treated animal.
The ticks are counted before and after treatment. The number of ticks on the treated animals and those on the controls is counted.
The results obtained are as follows:
NUMBER OF TICKS
Product A 5 mg/kg Control batch
Days 1 2 3 1 2 3 D-2 3 3 1 2 1 3 D-1 99 80 172 106 76 64
O Treatment
1 53 60 50 152 94 525
2 4 0 2 38 28 306
3 0 1 4 47 27 101
4 10 0 1 128 81 82
5 4 0 0 97 76 165
6 0 0 0 21 71 125
7 1 0 1 116 96 173
8 1 0 0 57 60 145
9 0 0 0 31 19 75 10 0 0 0 77 127 49 11 0 0 0 174 200 111 12 1 0 0 60 87 144 13 1 0 0 339 242 114 14 0 0 0 450 378 75 15 0 0 0 166 96 67 16 0 0 0 36 18 27 17 0 0 0 41 5 103 18 0 0 0 636 92 960 19 1 0 0 601 291 1076 20 0 0 0 133 242 316 21 0 0 0 12 137 29 1-21 195 10644
Efficacy 98.2 =0
Conclusion: product A shows remarkable activity.
Test 3: Test on Boophilus microplus (strain Mexico)
8 young bulls were infected with larvae of Boophilus microplus (sensitive strain Mexico), so that at the moment of treatment all the stages of development are represented on the animals.
Product A was administered at doses of 5, 2.5 and 1 mg per kg of weight of treated animal, in solution in a mixture composed of 85 g of dimethylformamide, 7 g of Emulsogen and 3 g of
Arcopal so that the volume to be applied is 40 or 30 cm3. (Arcopal is a surface-active agent constituted by a non-ionic alkylphenol polyglycol ether. Emulsogen is an emulsifying agent for oils, paraffins and other organic solvents).
The ticks are counted before and after treatment and the number of ticks on the treated animals is compared with that on the control animals. The percentage activity of the product is determined.
The results obtained are as follows: NUMBER OF TICKS
Dose of product A 5 mg/kg (40 cm ) 2.5 mg/kg (30 cm ) 1 mg/kg (30 cm ) Control batch
Days 1 2 3 4 5 6 7 8
D - 3 1 0 0 0 0 0 0 0
D - 2 136 0 23 0 21 10 36 0
D - 1 320 0 234 0 103 26 128 0
D TREATMENT
D + 1 2 0 7 0 26 8 63 5
D + 2 0 0 4 0 2 3 2 0
D + 3 0 0 1 0 4 0 38 1
D + 4 1 0 7 0 12 1 262 5
D + 5 2 0 1 0 8 1 67 2
D + 6 0 0 1 0 1 3 11 2
D + 7 0 0 1 0 1 4 3 11
D + 8 0 0 0 0 0 2 8 10
D + 9 0 0 0 0 1 2 1 3
D + 10 1 0 0 0 0 1 11 6
D + 11 0 0 0 0 0 0 67 65 Continued
NUMBER OF TICKS
Dose of product A 5 mg/kg (40 cm ) 2.5 mg/kg (30 cm ) 1 mg/kg (30 cm ) Control batch
Days 1 2 3 4 5 6 7 8
D TREATMENT
D + 12 0 0 0 0 1 2 44 27
D + 13 0 0 0 0 1 0 29 35
D + 14 0 0 0 0 0 2 39 39
D + 15 0 0 0 0 2 7 74 21
D + 16 0 0 0 0 1 0 4 6
D + 17 0 0 0 0 0 2 16 9
D + 18 0 0 0 0 0 0 43 49
D + 19 0 0 0 0 0 3 103 39
D + 20 0 0 0 0 0 2 40 10
D + 21 0 0 0 0 0 3 7 1 1 - 21 6 0 22 0 60 46 932 346 At doses of 5 mg/kg, 2.4 mg/kg and 1 mg/kg the percentage efficacy of product A is determined to be effectively 99.4%, 97.6% and 94.3%.
Conclusion: Compound A shows remarkable activity.
Test 4: Test on Rhipicephalus appendiculatus, Rhipicephalus evertsi, Rhipicephalus simus,
Amblyomma Hebraeum and Hyalomma Species
Product A was administered at doses of 5, 2.5 and 1 mg/kg of weight of treated animal.
The animals were heavily infected naturally with several species of ticks.
The results obtained 1, 2 and 3 days after treatment are summarised in the table below:
NUMBER OF TICKS
Body day of the test
No. of weight before after treatment the animal Dose (kg) treatment
1 2 3
1 5 40 > 200 2 10 9
2 5 40 > 200 0 10 6
3 5 40 > 200 0 10 6
4 2.5 40 > 200 1 15 2
5 2.5 80 > 200 0 5 2
6 2.5 40 > 100 0 6 0
7 1 40 > 200 6 10 19
8 1 230 > 200 0 31 12
9 1 270 > 200 - 42 41 10 1 110 > 100 2 9 7 11 1 130 > 200 9 - 3 12 1 240 > 200 0 24 10 13 1 130 > 100 0 0 6
Conclusion: Under conditions of natural infestation with several different species of ticks, compound A shows remarkable activity.
Test 5: Test on stock animals covered with ticks, in Africa
Adult cows and calves of about 8 months are used. These animals are covered with ticks.
They are treated using a solution containing either 4 mg, 5 mg or 10 mg of product A per kg of weight of treated animal.
The ticks are counted on the day of treatment and on the following days.
The results are as follows: Animal Weight of Dose Volume Number of ticks
Treated the animal mg/kg Administration applied D D + 1 D + 2 D + 3
Cow 300 kg 4 parnting 20 ml 68/P: + 0 1 3
Calf 120 kg 5 the 10 ml 71/P: + + + + 0 4 1
Calf 156 kg 10 backbone 26 ml 153/p: + + + + 0 3 1
P = Pupae only in the folds of the ears.
Conclusion: product A shows remarkable activity.
Example 1: Example of composition
Compositions were prepared corresponding to the following formulation: -Product A 1.7 g -Dimethylformamide 40 cm "live oil 40 cm3
Example 2: Example of composition =
Compositions were prepared corresponding to the following formulation: -Produt A 1.6 g -Dimethylformamide 85 cm -Emulsogen 7 9 -Arcopal 3 g.
Claims (24)
1. Compositions adapted for administration to a portion of the surface of the body of a warm-blooded animal comprising, as active ingredient, at least one compound of formula I
wherein
X1 represents a hydrogen, fluorine, chlorine or bromine atom;
X2 represents a fluorine, chlorine or bromine atom,
X3 represents a chlorine, bromine or iodine atom and
R represents a benzyl radical (optionally substituted by one or more substituents selected from C14 alkyl radicals, C2-6 alkenyl radicals, C2-6 alkenyloxy radicals, C4-8 alkadienyl radicals, methylenedioxy radicals, benzyl radicals and halogen atoms); a group of formula:
(in which R1 represents a hydrogen atom or a methyl radical and R2 represents a monocyclic aryl group or a group of formula -CH2-C-=CH); a group of formula:
(in which R3 represents an organic C26 aliphatic radical containing one or more carbon-carbon unsaturations); a group of formula:
(in which R4 represents a hydrogen atom or a group of formula -CN or -CrCH, R5 represents a chlorine atom or a methyl radical and n is 0, 1 or 2); or a group of formula
(in which R6, R7, R8 and R9, which may be the same or different, each represents a hydrogen atom, a chlorine atom or a methyl radical and the symbol S/I indicates an aromatic ring or dihydro or tetrahydro analogue thereof); said active ingredient being in association with a vehicle capable of permitting passage of the active ingredient through the skin barrier of the animal.
2. Compositions as claimed in claim 1 wherein, in the compound of formula I, R represents a 5-benzyl-3-furylmethyl group; a group of formula
(in which R3 represents a vinyl, propen-1-yl, buta-1,3-dienyl or buten-1-yl radical); or a 3phenoxybenzyl, a-cyano-3-phenoxybenzyl or a-ethynyl-3-phenoxybenzyl group.
3. Compositions as claimed in claim 2 wherein the active ingredient comprises a compound of formula IA,
(in which X represents a chlorine or bromine atom).
4. Compositions as claimed in claim 3 wherein the active ingredient comprises (S) oz-cyano- 3-phenoxybenzyl (1 R, cis)-2, 2-dimethyl-3-(2, 2-dichloro- 1 ,2-dibromoethyl)-cyclopropane-l -carboxylate.
5. Compositions as claimed in claim 3 wherein the active ingredient comprises (S) a-cyano3-phenoxybenzyl (1 R, cis)-2, 2-dimethyl-3-( 1 ,2, 2, 2-tetrabromoethyl)-cyclopropane- 1 -carboxylate.
6. Compositions as claimed in any pre'ceding claim wherein the vehicle comprises an oily solution of a dispersing agent.
7. Compositions as claimed in claim 6 wherein the dispersing agent comprises dimethylformamide, dimethyl-sulphoxide or dimethylacetamide.
8. Compositions as claimed in claim 6 or claim 7 wherein the oily solution comprises a vegetable oil.
9. Compositions as claimed in claim 8 wherein the vegetable oil is olive oil or ground-nut oil.
10. Compositions as claimed in any preceding claim including an emulsifying agent and/or a surface active agent.
11. Compositions as claimed in any preceding claim for use in the control of parasites.
1 2. Compositions as claimed in claim 11 for use in the control of acarids.
1 3. Compositions as claimed in any preceding claim adapted for administration to a part of the backbone of the animal.
14. Compositions as claimed in any preceding claim containing from 0.5 to 10 mg of active ingredient per kg of body weight of the animal.
1 5. Compositions as claimed in claim 1 substantially as herein described.
1 6. Compositions substantially as herein described in Example 1 or Example 2.
1 7. A method of treating or preventing an infestation by parasites of a warm-blooded animal which comprises applying to a portion of the surface of the body of the said animal a composition as claimed in claim 1.
1 8. A method as claimed in claim 17 wherein the composition is as defined in any one of claims 2 to 10.
1 9. A method as claimed in claim 1 7 or claim 18 wherein the composition is applied to the backbone of the animal or a part thereof.
20. A method as claimed in any one of claims 1 7 to 1 9 wherein from 0.5 to 10 mg of active ingredient of formula I are applied per kg bodyweight of the animal.
21. A method as claimed in any one of claims 17 to 20 for the treatment or prevention of an infestation by acarids.
22. A method as claimed in any one of claims 17 to 21 wherein the animal is selected from cattle, sheep and pigs.
23. A method as claimed in claim 1 7 substantially as herein described.
24. Each and every novel method, process, composition and product herein disclosed.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7916892A FR2484256B1 (en) | 1979-06-29 | 1979-06-29 | METHOD FOR CONTROLLING PEST OF HOT BLOOD ANIMALS |
Publications (2)
Publication Number | Publication Date |
---|---|
GB2052988A true GB2052988A (en) | 1981-02-04 |
GB2052988B GB2052988B (en) | 1983-04-07 |
Family
ID=9227301
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB8021250A Expired GB2052988B (en) | 1979-06-29 | 1980-06-27 | Compositions for the control of parasites in warm-blooded animals |
Country Status (9)
Country | Link |
---|---|
JP (1) | JPS568316A (en) |
AU (1) | AU541208B2 (en) |
CH (1) | CH645023A5 (en) |
DE (1) | DE3024323A1 (en) |
FR (1) | FR2484256B1 (en) |
GB (1) | GB2052988B (en) |
NZ (1) | NZ194171A (en) |
OA (1) | OA06524A (en) |
ZA (1) | ZA803621B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0088919A1 (en) * | 1982-03-09 | 1983-09-21 | Bayer Ag | Pesticidal pour-on formulations |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2471187A1 (en) * | 1979-12-10 | 1981-06-19 | Roussel Uclaf | NEW COMPOSITIONS FOR THE CONTROL OF PARASITES OF HOT-BLOOD ANIMALS |
HU182802B (en) * | 1980-02-26 | 1984-03-28 | Biogal Gyogyszergyar | Fotostabil delousing (insecticide) composition containing synthetic piretroides |
FR2523444B1 (en) * | 1982-03-16 | 1987-07-24 | Wellcome Australia | LOCALLY APPLIED PEST CONTROL FORMULA FOR MAMMALS CONTAINING A COMBINATION OF A PYRETHROID AND A THIAZOLE |
FR2555449B1 (en) * | 1983-11-25 | 1986-11-14 | Applipharm Ctre Rech Applic P | PYRETHROID COMPOSITION FOR THE LOCAL TREATMENT OF SKIN PARASITOSIS |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL180633C (en) * | 1973-06-22 | 1900-01-01 | Bayer Ag | PROCESS FOR PREPARING AN ANTHELMINTIC EFFECTIVE VETERINARY Pour-on Preparation. |
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 |
FR2419932A2 (en) * | 1978-03-17 | 1979-10-12 | Roussel Uclaf | NEW ESTERS OF CYCLOPROPANE CARBOXYLIC ACIDS CONTAINING A POLYHALOGENIC SUBSTITUTE, PREPARATION PROCESS AND INSECTICIDE COMPOSITIONS CONTAINING THEM |
FR2398041A2 (en) * | 1977-07-19 | 1979-02-16 | Roussel Uclaf | CYCLOPROPANE CARBOXYLIC ACID ESTERS CONTAINING A POLYHALOGENIC SUBSTITUTE, PROCESS FOR PREPARATION AND THEIR APPLICATION AS INSECTICIDES, ACARICIDES, NEMATICIDES AND AS VETERINARY MEDICINAL PRODUCTS |
FR2364884A1 (en) * | 1976-09-21 | 1978-04-14 | Roussel Uclaf | Fungicidal bactericidal cyclopropane carboxylic acid derivs. - are intermediates in prepn. of insecticidal, acaricidal, nematocidal and antifungal ester(s) |
NZ186081A (en) * | 1976-12-24 | 1982-03-09 | Wellcome Found | Ectoparasiticidal compositions containing a pyrethroid and an organophosphorus compound |
GB1592056A (en) * | 1976-12-24 | 1981-07-01 | Wellcome Found | Synergistic parasiticidal compositions |
EG13121A (en) * | 1977-02-11 | 1981-03-31 | Ciba Geigy Ag | Process for preparing of cyclopanecarboxylic acid esters and their use in pest control |
DE2709264C3 (en) * | 1977-03-03 | 1982-01-21 | Bayer Ag, 5090 Leverkusen | Substituted phenoxybenzyloxycarbonyl derivatives, processes for their preparation and their use as insecticides and acaricides and new intermediates |
DE2730515A1 (en) * | 1977-07-06 | 1979-01-18 | Bayer Ag | SUBSTITUTED PHENOXYBENZYLOXYCARBONYL DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES AND ACARICIDES |
-
1979
- 1979-06-29 FR FR7916892A patent/FR2484256B1/en not_active Expired
-
1980
- 1980-04-29 OA OA57100A patent/OA06524A/en unknown
- 1980-06-17 ZA ZA00803621A patent/ZA803621B/en unknown
- 1980-06-27 CH CH498180A patent/CH645023A5/en not_active IP Right Cessation
- 1980-06-27 JP JP8667580A patent/JPS568316A/en active Granted
- 1980-06-27 DE DE19803024323 patent/DE3024323A1/en active Granted
- 1980-06-27 GB GB8021250A patent/GB2052988B/en not_active Expired
- 1980-06-27 NZ NZ194171A patent/NZ194171A/en unknown
- 1980-06-27 AU AU59736/80A patent/AU541208B2/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0088919A1 (en) * | 1982-03-09 | 1983-09-21 | Bayer Ag | Pesticidal pour-on formulations |
Also Published As
Publication number | Publication date |
---|---|
ZA803621B (en) | 1982-01-27 |
AU5973680A (en) | 1981-01-08 |
JPH0448775B2 (en) | 1992-08-07 |
DE3024323A1 (en) | 1981-01-22 |
FR2484256A1 (en) | 1981-12-18 |
AU541208B2 (en) | 1984-12-20 |
FR2484256B1 (en) | 1986-10-24 |
DE3024323C2 (en) | 1991-04-25 |
OA06524A (en) | 1981-07-31 |
NZ194171A (en) | 1985-01-31 |
CH645023A5 (en) | 1984-09-14 |
GB2052988B (en) | 1983-04-07 |
JPS568316A (en) | 1981-01-28 |
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Legal Events
Date | Code | Title | Description |
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PE20 | Patent expired after termination of 20 years |
Effective date: 20000626 |