DK165434B - Stabiliserede pesticide midler - Google Patents
Stabiliserede pesticide midler Download PDFInfo
- Publication number
- DK165434B DK165434B DK490686A DK490686A DK165434B DK 165434 B DK165434 B DK 165434B DK 490686 A DK490686 A DK 490686A DK 490686 A DK490686 A DK 490686A DK 165434 B DK165434 B DK 165434B
- Authority
- DK
- Denmark
- Prior art keywords
- amitraz
- agent according
- aluminum
- pesticide agents
- alkoxide
- Prior art date
Links
- 239000000575 pesticide Substances 0.000 title claims abstract description 4
- 239000003795 chemical substances by application Substances 0.000 title claims description 12
- QXAITBQSYVNQDR-ZIOPAAQOSA-N amitraz Chemical compound C=1C=C(C)C=C(C)C=1/N=C/N(C)\C=N\C1=CC=C(C)C=C1C QXAITBQSYVNQDR-ZIOPAAQOSA-N 0.000 claims abstract description 19
- 229960002587 amitraz Drugs 0.000 claims abstract description 19
- -1 aluminium alkoxides Chemical class 0.000 claims abstract description 17
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims description 16
- RDYMFSUJUZBWLH-SVWSLYAFSA-N endosulfan Chemical compound C([C@@H]12)OS(=O)OC[C@@H]1[C@]1(Cl)C(Cl)=C(Cl)[C@@]2(Cl)C1(Cl)Cl RDYMFSUJUZBWLH-SVWSLYAFSA-N 0.000 claims description 5
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 1
- 230000000087 stabilizing effect Effects 0.000 claims 1
- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 claims 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 239000012669 liquid formulation Substances 0.000 abstract 1
- 238000009472 formulation Methods 0.000 description 7
- 230000015556 catabolic process Effects 0.000 description 6
- 238000006731 degradation reaction Methods 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 241000158500 Platanus racemosa Species 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- LRJOXARIJKBUFE-UHFFFAOYSA-N 1,2-diethyl-3-methylbenzene Chemical class CCC1=CC=CC(C)=C1CC LRJOXARIJKBUFE-UHFFFAOYSA-N 0.000 description 1
- QFMDFTQOJHFVNR-UHFFFAOYSA-N 1-[2,2-dichloro-1-(4-ethylphenyl)ethyl]-4-ethylbenzene Chemical compound C1=CC(CC)=CC=C1C(C(Cl)Cl)C1=CC=C(CC)C=C1 QFMDFTQOJHFVNR-UHFFFAOYSA-N 0.000 description 1
- BAMWORSGQSUNSC-UHFFFAOYSA-N 1-ethyl-2,3,4-trimethylbenzene Chemical class CCC1=CC=C(C)C(C)=C1C BAMWORSGQSUNSC-UHFFFAOYSA-N 0.000 description 1
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical class CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 description 1
- JYCQQPHGFMYQCF-UHFFFAOYSA-N 4-tert-Octylphenol monoethoxylate Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCO)C=C1 JYCQQPHGFMYQCF-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- WRMFBHHNOHZECA-UHFFFAOYSA-N butan-2-olate Chemical compound CCC(C)[O-] WRMFBHHNOHZECA-UHFFFAOYSA-N 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 150000005195 diethylbenzenes Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XLDBGFGREOMWSL-UHFFFAOYSA-N n,n'-bis[2,6-di(propan-2-yl)phenyl]methanediimine Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N=C=NC1=C(C(C)C)C=CC=C1C(C)C XLDBGFGREOMWSL-UHFFFAOYSA-N 0.000 description 1
- 229920002113 octoxynol Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- BEZDDPMMPIDMGJ-UHFFFAOYSA-N pentamethylbenzene Chemical class CC1=CC(C)=C(C)C(C)=C1C BEZDDPMMPIDMGJ-UHFFFAOYSA-N 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005201 tetramethylbenzenes Chemical class 0.000 description 1
- 150000005199 trimethylbenzenes Chemical class 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 150000003738 xylenes Chemical class 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
- 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
- A01N25/22—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 ingredients stabilising the active ingredients
-
- 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
- A01N37/52—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 groups, e.g. carboxylic acid amidines
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compounds Of Unknown Constitution (AREA)
- Prostheses (AREA)
- Superconductors And Manufacturing Methods Therefor (AREA)
Description
Opfindelsen angår pesticide midler indeholdende amitraz.
Amitraz er trivialnavnet for insekticidet og aca-ricidet, hvis kemiske navn er N-methylbis(2,4-xylylimi-5 nomethyl)amin. Denne forbindelse formuleres i almindelighed som et emulgerbart koncentrat, men i denne form kan der ske nedbrydning, især under varme og/eller fugtige betingelser. Det er derfor ofte nødvendigt at tilsætte en stabilisator. En særlig værdifuld stabilisator 10 har været epichlorhydrin, men anvendelsen af denne stabilisator er forbudt i nogle lande. I ansøgerens britiske patentansøgning nr. 2058570 gøres der krav på anvendelse af visse carbodiimider, specielt di-(2,6-diiso-propylphenyl)carbodiimid, som stabilisatorer, men disse 15 forbindelser lider af visse ulemper. Således har visse myndigheder indtil nu ikke tilladt deres anvendelse, og de stabiliserer endvidere ikke formuleringer, hvortil endosulfan er tilsat, tilstrækkeligt.
Det har nu vist sig, at aluminiumalkoxider kan 20 virke som meget gode stabilisatorer for amitraz.
Midlet indeholder sædvanligvis fra 0,5 til 50% (vægt/vol), f.eks. 5 til 30%, især 10 til 20% amitraz, fra 0,1 til 5%, f.eks. 0,5 til 2%, aluminiumalkoxid og eventuelt indtil 35% overfladeaktivt middel, fortrins-25 vis fra 5 til 25%. Som tidligere angivet er aluminiumalkoxider særligt værdifulde, når endosulfan også er til stede, f.eks. i mængder fra 10 til 40%, især 20 til 30% (vægt/vol).
Egnede opløsningsmidler omfatter f.eks. aromati-30 ske carbonhydrider, såsom alkylbenzener, herunder de forskellige trimethylbenzener, methylethylbenzener, di-methylbenzener, diethylbenzener, tetramethylbenzener, trimethylethylbenzener, methyldiethylbenzener, pentame-thylbenzener, naphthalen og forskellige methylnephthale-35 ner og blandinger deraf; chlorerede carbonhydrider, såsom chlorerede alkaner, chlorerede alkener og chloreret
DK 165434B
2 benzen, og chlorerede alkylbenzener; ketonopløsningsmid-ler, såsom cyclohexanon, isophoron, N-methyl-pyrrolidon, diisobutylketon og methylis obu tylketon.
De overfladeaktive midler kan være alle dem, der 5 sædvanligvis anvendes indenfor teknikken, fortrinsvis ikke-ioniske, anioniske eller en blanding af ikke-ioni-ske og anioniske overfladeaktive midler.
Ikke-ioniske overfladeaktive midler omfatter f.eks. ethoxylerede alkylphenoler, såsom eventuelt ter-10 minalt blokerede alkylphenolethoxylater; ethoxylerede alifatiske alkoholer; ethoxylerede aminer; ethoxylerede fedtsyrer og fede syrer og estere af fedtsyrer og fede syrer; ethoxylerede alkylolamider; blokpolymere/copoly-mere af ethylenoxid og propylenoxid; alkylolamider og 15 ethoxylerede/propoxylerede alkylphenoler eller fedtal-koholer.
Anioniske forbindelser omfatter f.eks. sulfonater, såsom alkylarylsulfonater eller råoliesulfonater; sulfater, såsom alkoholsulfater eller andre sulfater, 20 phosphatestere eller sulfosuccinater.
Aluminiumalkoxidet er i almindelighed et C^g-alkoxid. Blandinger af alkoxider kan anvendes, og en særligt egnet blanding er blandingen af isopropoxidet og sec-butoxidet.
25 Andre pesticider kan inkorporeres i midlerne ifølge opfindelsen, især endosulfan.
Skønt opfindelsen er særligt anvendelig i forbindelse med stabilisering af emulgerbare koncentrater, dvs. en koncentrat, som fortyndes med vand inden anven-30 delsen, til dannelse af en emulsion af den aktive komponent i vand, kan andre flydende midler, indeholdende amitraz, stabiliseres i overensstemmelse med opfindelsen. F.eks. kan en ULV-formulering (formulering med meget lavt volumen), omfattende en opløsning af amitraz og 35 aluminiumoxidet(erne) i et passende opløsningsmiddel, fremstilles til direkte sprøjtning uden fortynding,
DK 165434B
3 eller et overhældningspræparat til dyr kan fremstilles til direkte påføring til dyrene ved opløsning af amitraz og alkoxidet i et oliemedium, som eventuelt indeholder et coopløsningsmiddel.
5 Opfindelsen belyses nærmere ved hjælp af de føl gende eksempler.
Eksempel 1
Et emulgerbart koncentrat blev formuleret som 10 følger: % væqt/vol amitraz 15 endosulfan 28
Triton®CF 101 13 15 Aerosol OT-S* 10
Aliso B* 1
Solvesso®2002 til 100 * Benzylblokeret octylphenol-ethoxylat 20 3 4 = Dioctylnatriumsulfosuccinat (70% i carbon- 2 = Methylnaphthalenfraktion 25 Til sammenligning oparbejdedes en lignende formu lering under udeladelse af Aliso B. Prøver blev. opbeva-
O
ret i IL-beholdere ved temperaturer på 40 og 50 C. Vand tilsattes til hver formulering til sikring af et begyndelsesvandindhold på 0,1%. Efter to måneder blev portio-30 ner af hver prøve analyseret for nedbrydning af amitraz ved gas-væskechromatografi.
3 hydridopløsningsmiddel) 4 = 50:50 blanding af aluminiumisopropoxid og see.-butoxid
DK 165434 B
4
Resultaterne er som følger: % nedbrydning af amitraz
Temperatur Formulering ifølge Sammenligning 5 opfindelsen 40°C 0 10 50 °C 0 12
Det kan ses, at aluminiumalkoxiderne formindskede amitraznedbrydningen væsentligt.
10
Eksempel 2
Et emulgerbart koncentrat formuleredes som følger: % vsgt/vol 15 amitraz 12,5
Ethylan®KEO5 20
Aliso B 1
Solvesso®200 til 100 20 * = Nonylphenylethoxylat
Dette blev testet på sammen måde som i eksempel 1 (bortset fra at der ikke tilsattes ekstra vand) og sammenlignet med en formulering uden Aliso B.
Resultaterne efter tre måneders opbevaring var 25 som følger: % nedbrydning af amitraz
Temperatur Formulering ifølge Sammenligning
O
C_ opfindelsen 20 0 3 30 40 0 .6 50 0 3 .
50 18
Det kan ses, at aluminiumalkoxiderne igen for-35 mindsker amitraznedbrydningen væsentligt.
Claims (8)
1. Et flydende pesticidt middel, kendetegnet ved, at det indeholder en opløsning af amitraz i et organisk opløsningsmiddel og en stabiliserende mængde af et eller flere aluminiumalkoxider.
2. Middel ifølge krav 1, kendetegnet ved, at aluminiumalkoxidet omfatter en blanding af alu-miniumisopropoxid og aluminium-sec-butoxid.
3. Middel ifølge krav i eller 2, kendetegnet ved, at det indeholder 0,5 ti 50% vægt/vol 10 amitraz.
4. Middel ifølge krav 3, kendetegnet ved, at det indeholder fra 5 til 30% vægt/vol amitraz.
5. Middel ifølge krav 4, kendetegnet ved, at det indeholder fra 10 til 20% vægt/vol amitraz.
6. Middel ifølge et vilkårligt af de foregående krav, kendetegnet ved, at det indeholder fra 0,1 til 5% vægt/vol aluminiumalkoxid.
7. Middel ifølge krav 5, kendetegnet ved, at det indeholder fra 0,5 til 2% vægt/vol alumi- 20 niumalkoxid.
8. Middel ifølge et vilkårligt af de foregående krav, kendetegnet ved, at det desuden inde- · holder fra 10 til 40% vægt/vol endosulfan.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB858525447A GB8525447D0 (en) | 1985-10-16 | 1985-10-16 | Pesticidal compositions |
| GB8525447 | 1985-10-16 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| DK490686D0 DK490686D0 (da) | 1986-10-14 |
| DK490686A DK490686A (da) | 1987-04-17 |
| DK165434B true DK165434B (da) | 1992-11-30 |
| DK165434C DK165434C (da) | 1993-04-13 |
Family
ID=10586716
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK490686A DK165434C (da) | 1985-10-16 | 1986-10-14 | Stabiliserede pesticide midler |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US4710512A (da) |
| EP (1) | EP0226285B1 (da) |
| JP (1) | JPH0751483B2 (da) |
| KR (1) | KR950009174B1 (da) |
| CN (1) | CN1017957B (da) |
| AT (1) | ATE59528T1 (da) |
| AU (1) | AU570596B2 (da) |
| BR (1) | BR8605037A (da) |
| CA (1) | CA1266229A (da) |
| CS (1) | CS258491B2 (da) |
| DD (1) | DD250042A5 (da) |
| DE (1) | DE3676466D1 (da) |
| DK (1) | DK165434C (da) |
| EG (1) | EG18048A (da) |
| FI (1) | FI83470C (da) |
| GB (1) | GB8525447D0 (da) |
| GR (1) | GR3001672T3 (da) |
| HU (1) | HU203830B (da) |
| IE (1) | IE58898B1 (da) |
| IL (1) | IL80306A (da) |
| MW (1) | MW7086A1 (da) |
| NZ (1) | NZ217919A (da) |
| OA (1) | OA08428A (da) |
| PH (1) | PH21782A (da) |
| PT (1) | PT83545B (da) |
| RU (1) | RU1812944C (da) |
| TR (1) | TR22547A (da) |
| ZA (1) | ZA867811B (da) |
| ZM (1) | ZM9586A1 (da) |
| ZW (1) | ZW20786A1 (da) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7906128B2 (en) * | 2002-10-21 | 2011-03-15 | Wyeth Llc | Use of neuronal sodium channel antagonists for the control of ectoparasites in homeothermic animals |
| PE20060785A1 (es) * | 2004-10-08 | 2006-09-19 | Wyeth Corp | Composiciones de amitraz |
| US20080112993A1 (en) * | 2005-05-24 | 2008-05-15 | Wyeth | High-dose, long-lasting ectoparasiticide for extended control |
| TWI368505B (en) * | 2005-05-24 | 2012-07-21 | Wyeth Corp | Versatile high load concentrate compositions for control of ecto-parasites |
| TW200846029A (en) * | 2007-02-09 | 2008-12-01 | Wyeth Corp | High dose, long-acting ectoparasiticide for extended control |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1488906A (en) * | 1974-11-09 | 1977-10-19 | Boots Co Ltd | Pesticidal compositions |
| ZA804985B (en) * | 1979-09-20 | 1981-08-26 | Boots Co Ltd | Pesticidal compositions |
| GB2058570B (en) * | 1979-09-20 | 1983-02-23 | Boots Co Ltd | Pesticidal compositions |
| US4479968A (en) * | 1980-10-17 | 1984-10-30 | The Wellcome Foundation Ltd. | Control of ectoparasitic infestations of pigs |
-
1985
- 1985-10-16 GB GB858525447A patent/GB8525447D0/en active Pending
-
1986
- 1986-10-02 AT AT86307591T patent/ATE59528T1/de not_active IP Right Cessation
- 1986-10-02 DE DE8686307591T patent/DE3676466D1/de not_active Expired - Lifetime
- 1986-10-02 EP EP86307591A patent/EP0226285B1/en not_active Expired - Lifetime
- 1986-10-10 MW MW70/86A patent/MW7086A1/xx unknown
- 1986-10-13 ZW ZW207/86A patent/ZW20786A1/xx unknown
- 1986-10-13 OA OA58976A patent/OA08428A/xx unknown
- 1986-10-13 EG EG644/86A patent/EG18048A/xx active
- 1986-10-13 FI FI864116A patent/FI83470C/fi not_active IP Right Cessation
- 1986-10-13 ZM ZM95/86A patent/ZM9586A1/xx unknown
- 1986-10-14 CA CA000520358A patent/CA1266229A/en not_active Expired - Lifetime
- 1986-10-14 DK DK490686A patent/DK165434C/da not_active IP Right Cessation
- 1986-10-14 US US06/918,342 patent/US4710512A/en not_active Expired - Lifetime
- 1986-10-14 CS CS867418A patent/CS258491B2/cs not_active IP Right Cessation
- 1986-10-14 DD DD86295261A patent/DD250042A5/de not_active IP Right Cessation
- 1986-10-14 NZ NZ217919A patent/NZ217919A/xx unknown
- 1986-10-15 PT PT83545A patent/PT83545B/pt not_active IP Right Cessation
- 1986-10-15 BR BR8605037A patent/BR8605037A/pt not_active IP Right Cessation
- 1986-10-15 ZA ZA867811A patent/ZA867811B/xx unknown
- 1986-10-15 AU AU64125/86A patent/AU570596B2/en not_active Expired
- 1986-10-15 IE IE272386A patent/IE58898B1/en not_active IP Right Cessation
- 1986-10-15 JP JP61243306A patent/JPH0751483B2/ja not_active Expired - Fee Related
- 1986-10-15 IL IL80306A patent/IL80306A/xx not_active IP Right Cessation
- 1986-10-15 PH PH34372A patent/PH21782A/en unknown
- 1986-10-15 RU SU864028366A patent/RU1812944C/ru active
- 1986-10-15 HU HU864298A patent/HU203830B/hu unknown
- 1986-10-16 KR KR1019860008667A patent/KR950009174B1/ko not_active Expired - Lifetime
- 1986-10-16 TR TR38953/86A patent/TR22547A/xx unknown
- 1986-10-16 CN CN86106596A patent/CN1017957B/zh not_active Expired
-
1991
- 1991-03-27 GR GR91400385T patent/GR3001672T3/el unknown
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