GB2176107A - Pyrethroid compositions - Google Patents
Pyrethroid compositions Download PDFInfo
- Publication number
- GB2176107A GB2176107A GB08613018A GB8613018A GB2176107A GB 2176107 A GB2176107 A GB 2176107A GB 08613018 A GB08613018 A GB 08613018A GB 8613018 A GB8613018 A GB 8613018A GB 2176107 A GB2176107 A GB 2176107A
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- GB
- United Kingdom
- Prior art keywords
- parts
- polyethylene glycol
- composition according
- glycol
- average
- 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.)
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
-
- 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
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- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Pesticidal composition for controlling harmful insects and/or mites, which is liquid at room temperature, contains at least one pyrethroid as active ingredient and at least one of polyethylene glycol and polypropylene glycol as solvent. This composition has markedly decreased toxicity and has little danger of fire due to ignition of the solvent.
Description
SPECIFICATION
Pyrethroid compositions and method for controlling harmful insects and/or mites therewith
Background of the invention
This invention relates to pesticidal-composition which is liquid at room temperature and which contains pyrethroids as active ingredients and polyethylene glycol or polypropylene glycol as solvent.
Pesticides are usually formulated in various forms so that the active ingredient is easily and efficiently applied to plants and activity ofthe pesticides is fully performed. Oftheseformulations, oil formulation and emulsifiable concentrate are prepared by dissolving an active ingredient in aromatic hydrocarbons such as xylene orthe like with optional addition of synthetic surfactants. The oil formulation can be applied as it is and as emulsifiable concentrate which is diluted with waterto emulsion forapplication.
Generally, the conventional oil formulation and emulsifiable concentrate comprise pesticidal active ingredients, synthetic surfactants and a large amount of aromatic hydrocarbons such as xylene. These formulations have sometimes such problems as inflammability and maloder ofthe solvent such asxylene, toxicity and irritation due to the synthetic surfactants and the solvents to mammals and small animals and phytotoxityto crops. Even oil formulation and emulisifiable concentrate of pyrethroids which have recently been used as pesticides have the same problems as above. Thus, formulations with less problems are in great demand.
During the inventors' intensive researches on less-toxic formulations of pyrethroids, it has been found that use of polyethylene glycol or polypropylene glycol as solvent with pyrethroids as active ingredients gives a saferformulation which shows lower toxicity, and high flash point.
Summary ofthe invention
This invention provides pesticidal composition which is liquid at room temperature and contains pyrethroids as active ingredients and polyethylene glycol or polypropylene glycol as solvents.
Description ofthe invention
The compositions ofthis invention will be explained below.
As examples of the pyrethroids used in this invention, thefollowing compounds may be mentioned, butdo not limitthis invention thereto. Optically active isomers thereof are also included.
Compound No. Name ofcompound
(1) a-cyano-3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutyrate
(2) (S)-α-cyano-3-phenoxybenzyl(S)-2-(4-chlorophenyl)-3-methylbutyrate (3) α-cyano-3-phenoxybenzyl2,2,3,3-tetramethylcyclopropanecarboxylate (4) 3-phenoxybenzyl3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
(5) 3-phenoxybenzyl chrysanthemate (6) ol-cyano-3-phenoxybenzyl 3-(2,2-dichlorovinyl) 2,2-dimethyl-1 -cyclopropanecarboxylate
(7) a-cyano-3-(4-bromophenoxy)benzyl 2,2-dimethyl-3-(2,2-dichlorovinyl) cyclopropanecarboxylate
(8) α-cyano-3-(4-fluorophenoxy)benzyl2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate (9) α;-cyano-3-(4-bromophenoxy)benzyl2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate (10) a-cyano-3-(4-ch lorophenoxy)benzyl 2,2-dimethyl-3-(2,2-dichlorovi nyl )cyclopropanecarboxylate (11) α-cyano-3-(4-bromophenoxy)benzyl2,2-dimethyl-3-(2,2-dibromovinyl)cyclopropanecarboxylate (12) α;-cyano-3-phenoxenzylchrysanthemate (13) a-cyano-3-(4-bromophenoxy) benzyl 2-(4-chlorophenyl)-3-methylbutyrate
(14) a-cyano-3-(3-bromophenoxy) benzyl 2-(4-chlorophenyl)-3-methylbutyrate
(15) o-cyano-3-(4-chlorophenoxy)benzyl 2-(4-chlorophenyl)-3-methylbutyrate
(16) a-cyano-3-(44luorophenoxy)benzyl 2-(4-chlorophenyl)-3-methylbutyrate
(17) a-cyano-3-phenoxybenzyl 2r(4-bromophenyl)-3-methylbutyrate (18) a-cyano-3-phenoxybenzyl 2-(4-tert-butyl-phenyl)-3-methyl butyrate
(19) a-cyano-3-phenoxybenzyl 2-(3,4-methylenedioxyphenyl)-3-methylbutyrate
(20) (S)-a-cyano-m-phenoxybenzyl (1 R,3R)-3-(2,2-dibrommovinyl)-2,2-dimethylcyclopropanecarboxylate
(21) a-cyano-4-fiuoro-3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethyl cyclopropanecarboxylate
(22) a-cyano-3-phenoxybenzyl 2-ch loro-4-(trifl uo romethyl)anil ino-3-methyl butyrate (23) o-cyano-3-phenoxybenzyl 2-(4-difluoromethoxyphyenyl)-3-methylbutyrate
(24) cyano(5-phenoxy-2-pyridyl)methyl 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate (25) a-cyano-3-phenoxybenzyl 2,2-dimethyl-3-(1 ,2,2,2-tetrabromoethyl )cyclopropaneca rboxyl ate (26) α-cyano-3-phenoxybenzyl2,2-dimetthyl-3-(1,2-dichlor-3,3-dibromo)cyclopropanecarboxylate (27) α;-cyano-3-phenoxybenzyl1-(4-ethoxyphenyl)-2,2-dichlorocyclopropane-1-carboxylate (28) a-cyano-3-phenoxybenzyl 2,2-dimethyl-3-(2-chloro-3-trifluoromethylvinyl)
cyclopropanecarboxylate
(29) 1 -(3-phenoxybenzyloxy)-2-methyl-2-(4-ethoxyphenyl)propane
One or two or more of these pyrethroids may be used in combination. Furthermore, these compounds may be used in combination with other pesticides such as organo-phosphorous insecticides and carbamate insecticides, and soon.
The polyethylene glycols used in this invention include from those of low molecular weight such as diethylene glycol and triethylene glycol to those of 10,000, preferably 200 - 600, in terms of average molecular weight
As the polypropylene glycols used in this invention,there may be used those having an average molecular weight of up to 4,000, including dipropylene glycol. Those of 134-300 in terms of average molecularweight are preferred for an emulsifiable concentrate, taking into accountthe emulsifiability and solubility.
The pesticidal composition of this invention generally contain 0.1-50% byweight, preferably 0.1 -20%by weight, of pyrethroids as active ingredients for an emulsifiable concentrate. On the other hand, it contains 50 99 % byweight, preferably 80 - 99 % byweight, of polyethylene glycol or polypropylene glycol as solvents.
In the composition ofthis invention, if desired, polyethylene glycol and polypropylene glycol may be used in combination. Furthermore, other solvents, surfactants, stabilizers, etc. may be used as adjuvants therewith.
The composition ofthis invention can be used as it is and as emulsifiable concentrate which is diluted with waterto emulsion for application.
The present composition is liquid when it is applied, preferably at a temperature of 20 C or higher, more prefemblyatOt or higher.
As compared with the compositions oftheconventional formulation,the composition ofthis invention has been markedly improved in safety, namely, smaller danger of fire and smaller inhalation or contacttoxicityat the time of preparation and application ofthe composition and besides itis good in insecticidal andlor miticidal activity, emulsion stability and the storage stability of the active ingredient
The following Examples and Test Examples further illustrate this invention.
The pyrethroids used as active ingredients are indicated bythe number ofthe compounds enumerated hereinbefore and the part is by weight.
Example 1
To 5 parts or 10 parts ofcompound (1) was added diethylene glycol,triethylene glycol, polyethylene glycol (average molecular weig ht 200), polyethylene glycol (average molecularweight300) or polyethylene glycol (average molecularweight600) to make up 100 parts, respectively. Each was well stirred to obtain the compositions ofthis invention containing 5% and 10% of the active ingredient.
Example2
To 20 parts, 30 parts, 40 parts or 50 parts of compound (1) was added polyethylene glycol (average molecular weight 200), polyethylene glycol (average molecularweight300) or polyethylene glycol (average molecularweight 600) to make up 100 parts, respectively. Each was well stirred to obtain the compositions of this invention containing 20%, 30%, 40% or 50% ofthe active ingredient.
Example 3
To 5 parts or 10 parts of compound (2), (3), (4), (5) or (6) was added polyethylene glycol (average molecular weight 200), polyethylene glycol (average molecularweight300) or polyethylene glycol (average molecular weight 600) to make up 100 parts, respectively. Each was well stirred to obtain the compositions ofthis invention containing 5% or 10% ofthe active ingredient.
Example 4
To 5 parts, 10 parts, 20 parts, 30 parts, 40 parts or 50 parts of compound (1), (2), (3) or (6) was added polypropylene glycol (average molecularweight 200)to make up 100 parts, respectively. Each was well stirred to obtain the compositions ofthis invention containing 5%, 10%, 20%, 40%, or 50% ofthe active ingredient
Example5
5 parts of compound (1) was mixed with 90 parts of polyethylene glycol (average molecular weight 200) and 5 parts of polyethylene glycol (average molecular weight 6,000) to obtain the composition ofthis invention.
Example 6
5 parts of compound (1) was mixed with 80 parts of diethylene glycol and 15 parts of polyethylene glycol (average molecularweight 6,000) to obtain the composition ofthis invention.
Example 7
5 parts of compound (1), 5 parts of O,O-dimethyl-O-(3-methyl-4-nitrophenyl) phosphorothioate and 90 parts of polyethylene glycol (average molecularweight200) were mixed to obtain the composition ofthis invention.
Example 8
5 parts of compound (2), 50 parts of polyethylene glycol (average molecularweight300) and 45 parts of polypropylene glycol (average molecularweight200)were mixed to obtain the composition of this invention.
Example 9
5 parts of compound (2), 90 parts of polyethylene glycol (average molecular weight 300) and 5 parts of polypropylene glycol (average molecular weight 400) to obtain the composition ofthis invention.
Example 10
To 20 parts or 30 parts of compound (3) was added polyethylene glycol (average molecularweight 600)to make up 100 parts, respectively. Each ofthe mixtureswaswell stirred to obtain the compositions ofthis invention containing 20% or 30% of the active ingredient.
Example 11
20 parts of compound (4) was mixed with 80 parts of polyethylene glycol (average molecu lay wig ht 200, 300 or 600) to obtain each ofthe compositions ofthis invention containing 20% ofthe active ingredient, respectively.
Example 12
To 20 parts or 30 parts of compound (5) was added polyethylene glycol (average molecular weight 600) to make up 100 parts, respectively. Each was well stirred to obtain the compositions of this invention containing 20% or 30% of the active ingredient.
Example 13
To 20 parts, 30 parts, 40 parts or 50 parts of compound (6) was added polyethylene glycol (average molecularweight 200,300 or 600) to make up 100 parts, respectively. Each was well stirred to obtain the compositions of this invention containing 20%, 30%, 40% or 50% of the active ingredient.
Test Example 1
The pesticidal composition ofthis invention obtained in the above Examples were tested with respectto emulsion stability by the test method as described below.
100 ml of hard water (3 H) was added into a 250 ml glass stoppered measuring cylinder, to which was poured 0.1 ml of the pesticidal composition ofthis invention as shown in the following table. This cylinder was repeatedly tumbled thirty times for one minute to emulsify the composition. Then, the cylinderwas immersed in the water bath of 20 C for 15 minutes and thereafter emulsion stability was examined. The results ofthe examination were shown by the follolwing marks: "#" indicates that substantially no separation of oily cream was observed and "0" indicates that somewhat oily cream was recognized, but practically no problems.
The results are shown in Table 1.
Table 1
Content Solvent
Test of com- active Diethyl Tri- Polyethylene Polyethylene Polypropylene pounds ingre- ene ethyl- glycol(aver- glycol(aver- glycol(averdient glycol ene age molecular age molecular age molecular age molecular glycol weight 200) weight 300) weight 600) weight 200)
5% # # # # # # (1) 10% # # # # # # 20% - - # # # # 5% - - # # # # (2) 10% - - # # # # 20% - - - - - # 5% - - # # # # (3) 10% - - # # # # 20% - - - - # # 5% - - # # # # (4) 10% - - # # # 20% - - # # # 5% - - # # # (5) 10% - - # # # 20% - - - - # 5% - - # # # # (6) 10% - - # # # # 20% - - # # # # Test Example 2
The pesticidal compositions ofthis invention obtained in the above Examples 5 - 8 were tested with respect to emulsion stability bythesametest method as in Test Example 1. The results are shown in Table 2.
Table 2
Composition Emulsion stability Example 5 #
Example 6 #
Example7 Example 8 # Test Example 3
The pesticidal compositions ofthis invention were tested with respect to acute oral toxicity using ICR strain male mice of 6 weeks old to obtain LD50.
Furthermore, control tests were effected using emulsifiable concentrates prepared by the following conventional formulation (A).
The conventional formulation (A)-(1)
10 parts of compound (1), (3), (4), (5) or (6), 10 parts of Sorpol 3005X (emulsifier manufactured byToho
Chemical Co., Ltd.) and 80 parts ofxylene were mixed to obtain emulsifiable concentrates of the conventional formulation.
The conventional formulation (A)-(2)
5 parts of compound (2), 7 parts of Sorpol 3005X and 88 parts of xylene were mixed to obtain emulsifiable
concentrates ofthe conventional formulation.
The results are shown inTable3.
Table 3
Test compounds LD50
Compound Content Solvents (mglKg) No. ( /O) Polyethylene glycol
(average molecularweight 200) > 2,000
(1) 10
Polyethylene glycol
(average molecularweight 600) > 2,000
Polyethylene glycol
(average molecularweight 200) > 370
(3) 10
Polyethylene glycol
(average molecular weight 600) > 370
Polyethylene glycol
(average molecularweight200) > 7,500
(4) 10
Polyethylene glycol
(average molecularweight 600) > 7,500
Polyethylene glycol
(averagemolecularweight200) > 10,000
(5) 10
Polyethylene glycol (average molecularweig ht 600) > 10,000
Polyethylene glycol
(average molecular weight 200) > 1,600
(6) 10
Polyethylene glycol
(average molecular weight 600) > 1,600
Polypropylene glycol
(2) 5 (averagemolecularweight200) 615
(1) 10 XyleneandSorpol3005X 1,350
(3) 10 XyleneandSorpol3005X 250
(4) 10 Xylene and Sorpol 3005X 3,000
(5) 10 Xylene and Sorpol 3005X 2,500
(6) 10 Xylene and Sorpol 3005X 800
(2) 5 Xylene and Sorpol 3005X 325
Test Example 4
The following pesticidal compositions ofthis invention were subjected to heat stability test and decomposition percentage ofthe active ingredientwas measured.
The results are shown in Table 4.
Table 4
Content Decomposition percentage
Test of of active ingredient /O/oJ com- active Solvents pounds ingre- 40 C 50 C 60 C
dient after after after {%) I 1 1
month month month
5 Polyethylene glycol 0 1 4
10 (average molecular 0 1 4
20 weight 200) 0 0 2
5 Polyethylene glycol 0 1 1
(1) 10 (average molecular 0 1 1
20- weight 600) 0 3 3
5 Diethylene 0 0 1
10 glycol 0 4 4
Polypropylene
(3) 5 glycol 4 - 6
(average molecular
weight 200) Test Example 5 After diluting the composition ofthis invention with water to 25 ppm active ingredients; each ofthem was sprayed onto a potted cabbage at an application rate of 40 ml/pot by a spray gun.After drying with air, a leafof the cabbage was cut off and put in a polyethylene cup of 9.0 cm in diametertogetherwith 10 larvae (third instar) oftobacco cutworm (Spodoptera litura Fabricius). After3 days,the dead, moribund and living insects were counted and mortality was calculated.
Atthe same time, control tests were conducted with the emulsifiable concentrates prepared by the above-stated conventional formulation (A)-(2) and the following conventional formulation (B).
The conventional formulation (B)
5 parts of compound (3), 10 parts ofSolpol H770 (emulsifier manufactured by Toho Chemical Co., Ltd.) and 85parts of xylene were mixed to obtain the emulsifiable concentrate of the conventional formulation.
The results are shown in Table 5.
Table 5
Content
Test of Mortality active Solventandothers { /O) compounds ingre
dient (%)
Polyethylene glycol
(2) 5 (average molecular 93
weight 300)
(3) 5 " 93
Polypropylene glycol
(3) 5 (average molecular 97
weight 200)
(2) 5 Xylene and emulsifier 93
(3) 5 " 87
As compared with pesticidal compositions of the conventional formulations, those ofthis invention have a iowertoxicity and safer with smaller danger of fire caused by ignition of solvent They are also good in insecticidal and/or miticidal activity, emulsion stability and the storage stability of active ingredients.
Claims (11)
1. A pesticidal composition which is liquid at room temperature (20 C) and contains at least one pyrethroid as active ingredient and at least one polyethylene glycol or polypropylene glycol as solvent.
2. A composition according to claim 1 which comprises a polyethylene glycol having an average molecular weight of 100 - 10,000.
3. A composition according to claim 2 wherein the average molecularweight of the polyethylene glycol is 200-600.
4. A composition according to claim 1 which comprises a polypropylene glycol having an average molecularweightof 134-4000.
5. A composition according to claim 4wherein the average molecular weight of the polypropylene glycol is 134-300.
6. A composition according to any one of the preceding claims wherein content of the pyrethroid is 0.1 50% by weight and content of solvent is 50 - 99% by weight.
A . composition according to claim 6 wherein content ofthe pyrethroid is 0.1 -20% by weight and content of solvent is 80 - 99% by weight.
8. A composition according to any one of the preceding claims wherein the pyrethroid is used in combination with at least one other pesticide.
9. A composition according to claim 8 wherein said other pesticide is at least one organo-phosphorus insecticide or carbamate insecticide.
10. A composition according to claim 1 substantially as described with referenceto any one ofthe Examples.
11. A method for controlling harmful insects and/or mites which comprises applying to harmful insects and/or mites a pesticidal composition as claimed in any one ofthe preceding claims.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12082785 | 1985-06-03 | ||
| JP61066542A JPH07524B2 (en) | 1985-06-03 | 1986-03-24 | Pyrethroid pesticide composition |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8613018D0 GB8613018D0 (en) | 1986-07-02 |
| GB2176107A true GB2176107A (en) | 1986-12-17 |
| GB2176107B GB2176107B (en) | 1989-07-12 |
Family
ID=26407736
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8613018A Expired GB2176107B (en) | 1985-06-03 | 1986-05-29 | Pyrethroid compositions and method for controlling harmful insects and/or mites therewith |
Country Status (4)
| Country | Link |
|---|---|
| DK (1) | DK255686A (en) |
| FR (1) | FR2582481B1 (en) |
| GB (1) | GB2176107B (en) |
| SE (1) | SE8602465L (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992005699A1 (en) * | 1990-10-02 | 1992-04-16 | Alexander Alde | Insecticide composition |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1284651A (en) * | 1969-03-07 | 1972-08-09 | Scient Dev Company S A Proprie | Improvements in pesticidal concentrates and compositions |
| GB1516113A (en) * | 1974-07-26 | 1978-06-28 | Gerlach Gmbh Chem Fab E | Agent for destroying lice and their eggs(nits) |
| GB2024625A (en) * | 1978-06-12 | 1980-01-16 | Ciba Geigy Ag | Method of protecting keratinous material from attack by insects that feed on keratin |
| GB2065475A (en) * | 1979-12-10 | 1981-07-01 | Roussel Uclaf | Compositions for the control of parasites in warm-blooded animals |
| GB2117638A (en) * | 1982-03-16 | 1983-10-19 | Wellcome Australia | Pour-on formulation |
| GB2122493A (en) * | 1982-06-30 | 1984-01-18 | Dow Chemical Co | Increasing the effectiveness of synthetic organic oil soluble insecticides |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4048302A (en) * | 1974-06-03 | 1977-09-13 | Riviana Foods Inc. | Aqueous pesticidal solutions containing polyethylene glycol |
-
1986
- 1986-05-29 GB GB8613018A patent/GB2176107B/en not_active Expired
- 1986-05-29 FR FR8607717A patent/FR2582481B1/en not_active Expired - Lifetime
- 1986-05-30 SE SE8602465A patent/SE8602465L/en not_active Application Discontinuation
- 1986-05-30 DK DK255686A patent/DK255686A/en not_active Application Discontinuation
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1284651A (en) * | 1969-03-07 | 1972-08-09 | Scient Dev Company S A Proprie | Improvements in pesticidal concentrates and compositions |
| GB1516113A (en) * | 1974-07-26 | 1978-06-28 | Gerlach Gmbh Chem Fab E | Agent for destroying lice and their eggs(nits) |
| GB2024625A (en) * | 1978-06-12 | 1980-01-16 | Ciba Geigy Ag | Method of protecting keratinous material from attack by insects that feed on keratin |
| GB2065475A (en) * | 1979-12-10 | 1981-07-01 | Roussel Uclaf | Compositions for the control of parasites in warm-blooded animals |
| GB2117638A (en) * | 1982-03-16 | 1983-10-19 | Wellcome Australia | Pour-on formulation |
| GB2122493A (en) * | 1982-06-30 | 1984-01-18 | Dow Chemical Co | Increasing the effectiveness of synthetic organic oil soluble insecticides |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992005699A1 (en) * | 1990-10-02 | 1992-04-16 | Alexander Alde | Insecticide composition |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2582481B1 (en) | 1992-12-18 |
| DK255686D0 (en) | 1986-05-30 |
| SE8602465L (en) | 1986-12-04 |
| GB8613018D0 (en) | 1986-07-02 |
| FR2582481A1 (en) | 1986-12-05 |
| DK255686A (en) | 1986-12-04 |
| GB2176107B (en) | 1989-07-12 |
| SE8602465D0 (en) | 1986-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19960529 |