CA2222199C - Dispositif externe anti-parasitaire pour bovins a base de n-phenylpyrazole, en particulier boucles auriculaires - Google Patents
Dispositif externe anti-parasitaire pour bovins a base de n-phenylpyrazole, en particulier boucles auriculaires Download PDFInfo
- Publication number
- CA2222199C CA2222199C CA002222199A CA2222199A CA2222199C CA 2222199 C CA2222199 C CA 2222199C CA 002222199 A CA002222199 A CA 002222199A CA 2222199 A CA2222199 A CA 2222199A CA 2222199 C CA2222199 C CA 2222199C
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- haloalkyl
- radical
- use according
- halogen atom
- 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.)
- Expired - Lifetime
Links
- 241000283690 Bos taurus Species 0.000 title claims abstract description 15
- WITMXBRCQWOZPX-UHFFFAOYSA-N 1-phenylpyrazole Chemical compound C1=CC=NN1C1=CC=CC=C1 WITMXBRCQWOZPX-UHFFFAOYSA-N 0.000 title description 5
- 230000002141 anti-parasite Effects 0.000 title description 3
- 239000003096 antiparasitic agent Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 241000257232 Haematobia irritans Species 0.000 claims abstract description 21
- 239000013543 active substance Substances 0.000 claims abstract description 20
- 239000011159 matrix material Substances 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000001188 haloalkyl group Chemical group 0.000 claims description 42
- 125000005843 halogen group Chemical group 0.000 claims description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 241001465754 Metazoa Species 0.000 claims description 19
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- -1 4,5-dicyanoimidazol-2-yl Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 230000008030 elimination Effects 0.000 claims description 3
- 238000003379 elimination reaction Methods 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000006414 CCl Chemical group ClC* 0.000 claims 1
- 244000045947 parasite Species 0.000 abstract description 22
- 239000004014 plasticizer Substances 0.000 description 9
- 229940126062 Compound A Drugs 0.000 description 7
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 7
- 239000002917 insecticide Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 5
- 241000255925 Diptera Species 0.000 description 4
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 241000238631 Hexapoda Species 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 244000309465 heifer Species 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000005944 Chlorpyrifos Substances 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 2
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 210000004209 hair Anatomy 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- 238000009304 pastoral farming Methods 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 230000005180 public health Effects 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- QZCLKYGREBVARF-UHFFFAOYSA-N Acetyl tributyl citrate Chemical compound CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 description 1
- 239000005946 Cypermethrin Substances 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- 239000005906 Imidacloprid Substances 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 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 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229960005424 cypermethrin Drugs 0.000 description 1
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229960002380 dibutyl phthalate Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000001489 hematophagic effect Effects 0.000 description 1
- 229940056881 imidacloprid Drugs 0.000 description 1
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- 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 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000384 rearing effect Effects 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Le dispositif externe tel que boucle, notamment boucle auriculaire, destinée à l'élimination des parasites des bovins, en particulier Haematobia irritans, formée d'une matrice incluant de 0,1 à 40 %, de préférence de 2,5 à 10 % en poids par rapport à la boucle auriculaire, d'une substance active qui est au moins un composé de formule (I), ce dispositif externe étant conçu pour assurer une efficacité de plus de 30 semaines.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9604207 | 1996-03-29 | ||
| FR9604207A FR2746584B1 (fr) | 1996-03-29 | 1996-03-29 | Dispositif externe anti-parasitaire pour bovins a base de n-phenylpyrazole, en particulier boucles auriculaires |
| US69211296A | 1996-08-05 | 1996-08-05 | |
| US08/692112 | 1996-08-05 | ||
| PCT/FR1997/000539 WO1997036483A1 (fr) | 1996-03-29 | 1997-03-26 | Dispositif externe anti-parasitaire pour bovins a base de n-phenylpyrazole, en particulier boucles auriculaires |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2222199A1 CA2222199A1 (fr) | 1997-10-09 |
| CA2222199C true CA2222199C (fr) | 2007-11-13 |
Family
ID=26232630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002222199A Expired - Lifetime CA2222199C (fr) | 1996-03-29 | 1997-03-26 | Dispositif externe anti-parasitaire pour bovins a base de n-phenylpyrazole, en particulier boucles auriculaires |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE1010477A3 (fr) |
| BR (1) | BR9702178A (fr) |
| CA (1) | CA2222199C (fr) |
| FR (1) | FR2746596B1 (fr) |
| GR (1) | GR970100096A (fr) |
| IE (1) | IE970224A1 (fr) |
| IT (1) | ITTO970267A1 (fr) |
| NL (1) | NL1005671C2 (fr) |
| WO (1) | WO1997036483A1 (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW524667B (en) | 1996-12-05 | 2003-03-21 | Pfizer | Parasiticidal pyrazoles |
| GB0329314D0 (en) | 2003-12-18 | 2004-01-21 | Pfizer Ltd | Substituted arylpyrazoles |
| US7514464B2 (en) | 2003-12-18 | 2009-04-07 | Pfizer Limited | Substituted arylpyrazoles |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8713768D0 (en) * | 1987-06-12 | 1987-07-15 | May & Baker Ltd | Compositions of matter |
| DE3719732A1 (de) * | 1987-06-12 | 1989-01-05 | Bayer Ag | Substituierte 5-methylamino-1-arylpyrazole |
| NO179282C (no) * | 1991-01-18 | 1996-09-11 | Rhone Poulenc Agrochimie | Nye 1-(2-pyridyl)pyrazolforbindelser til kontroll av skadeinsekter |
| US5411737A (en) * | 1991-10-15 | 1995-05-02 | Merck & Co., Inc. | Slow release syneresing polymeric drug delivery device |
| MX9206034A (es) * | 1991-10-24 | 1993-05-01 | Roussel Uclaf | Sistema para el control de plagas. |
| US5321040A (en) * | 1993-06-02 | 1994-06-14 | Rhone-Poulenc Inc. | Pesticidal 1-aryl-5-(substituted N-cinnamylideneimino) pyrazoles |
| US5472955A (en) * | 1994-06-07 | 1995-12-05 | Y-Tex Corporation | Insecticide mixture for ear tags |
-
1997
- 1997-03-17 GR GR970100096A patent/GR970100096A/el unknown
- 1997-03-21 IE IE970224A patent/IE970224A1/en not_active Application Discontinuation
- 1997-03-26 BR BR9702178A patent/BR9702178A/pt not_active IP Right Cessation
- 1997-03-26 CA CA002222199A patent/CA2222199C/fr not_active Expired - Lifetime
- 1997-03-26 FR FR9703706A patent/FR2746596B1/fr not_active Expired - Lifetime
- 1997-03-26 WO PCT/FR1997/000539 patent/WO1997036483A1/fr not_active Ceased
- 1997-03-27 NL NL1005671A patent/NL1005671C2/nl not_active IP Right Cessation
- 1997-03-27 BE BE9700274A patent/BE1010477A3/fr not_active IP Right Cessation
- 1997-03-28 IT ITTO970267 patent/ITTO970267A1/it not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| MX9708994A (es) | 1998-10-31 |
| FR2746596A1 (fr) | 1997-10-03 |
| ITTO970267A1 (it) | 1997-09-29 |
| BR9702178A (pt) | 1999-03-16 |
| WO1997036483A1 (fr) | 1997-10-09 |
| NL1005671A1 (nl) | 1997-09-30 |
| NL1005671C2 (nl) | 1997-11-06 |
| CA2222199A1 (fr) | 1997-10-09 |
| BE1010477A3 (fr) | 1998-09-01 |
| IE970224A1 (en) | 1997-10-08 |
| FR2746596B1 (fr) | 1999-12-31 |
| GR970100096A (el) | 1997-11-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20170327 |