CA2393197C - Control of arthropods in animals with 1-arylpyrazoles - Google Patents
Control of arthropods in animals with 1-arylpyrazoles Download PDFInfo
- Publication number
- CA2393197C CA2393197C CA002393197A CA2393197A CA2393197C CA 2393197 C CA2393197 C CA 2393197C CA 002393197 A CA002393197 A CA 002393197A CA 2393197 A CA2393197 A CA 2393197A CA 2393197 C CA2393197 C CA 2393197C
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- Prior art keywords
- animal
- compounds
- compound
- formula
- haloalkyl
- 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
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- 241001465754 Metazoa Species 0.000 title claims abstract description 78
- 125000004961 1-arylpyrazolyl group Chemical group 0.000 title claims abstract description 8
- 241000238421 Arthropoda Species 0.000 title description 12
- 244000045947 parasite Species 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims description 105
- 150000003839 salts Chemical class 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 125000001188 haloalkyl group Chemical group 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 11
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 10
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 229910052717 sulfur Chemical group 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
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- 125000005842 heteroatom Chemical group 0.000 claims description 6
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- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 5
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
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- 125000006193 alkinyl group Chemical group 0.000 claims description 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 18
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- 125000006414 CCl Chemical group ClC* 0.000 description 15
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- 125000004093 cyano group Chemical group *C#N 0.000 description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 14
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 6
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- 235000019198 oils Nutrition 0.000 description 6
- 239000000575 pesticide Substances 0.000 description 6
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 102220042509 rs112033303 Human genes 0.000 description 5
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 5
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- 241000282412 Homo Species 0.000 description 4
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- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 244000144972 livestock Species 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 102220050625 rs193920967 Human genes 0.000 description 4
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical class OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 206010061217 Infestation Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241001674048 Phthiraptera Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000002285 corn oil Substances 0.000 description 3
- 235000005687 corn oil Nutrition 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 235000012054 meals Nutrition 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
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- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical group O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
-
- 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
- A01N47/08—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 one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/28—Two oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16865899P | 1999-12-02 | 1999-12-02 | |
| US60/168,658 | 1999-12-02 | ||
| PCT/EP2000/012100 WO2001040195A2 (en) | 1999-12-02 | 2000-12-01 | Control of arthropods in animals |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2393197A1 CA2393197A1 (en) | 2001-06-07 |
| CA2393197C true CA2393197C (en) | 2009-03-03 |
Family
ID=22612402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002393197A Expired - Lifetime CA2393197C (en) | 1999-12-02 | 2000-12-01 | Control of arthropods in animals with 1-arylpyrazoles |
Country Status (20)
| Country | Link |
|---|---|
| US (4) | US6569886B2 (enExample) |
| EP (1) | EP1237873B1 (enExample) |
| JP (1) | JP2003516941A (enExample) |
| KR (1) | KR100816914B1 (enExample) |
| CN (2) | CN1939909A (enExample) |
| AR (1) | AR033504A1 (enExample) |
| AU (1) | AU784798B2 (enExample) |
| BR (1) | BR0015945A (enExample) |
| CA (1) | CA2393197C (enExample) |
| CO (1) | CO5261614A1 (enExample) |
| CZ (1) | CZ20021898A3 (enExample) |
| ES (1) | ES2409630T3 (enExample) |
| HU (1) | HUP0300357A3 (enExample) |
| IL (2) | IL149856A0 (enExample) |
| MX (1) | MXPA02005511A (enExample) |
| MY (1) | MY129771A (enExample) |
| PL (1) | PL364874A1 (enExample) |
| TW (1) | TWI290137B (enExample) |
| WO (1) | WO2001040195A2 (enExample) |
| ZA (1) | ZA200204336B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005063020A1 (en) | 2003-12-24 | 2005-07-14 | Bayer Cropscience Gmbh | Plant growth regulation |
| JP4883296B2 (ja) | 2004-03-05 | 2012-02-22 | 日産化学工業株式会社 | イソキサゾリン置換ベンズアミド化合物及び有害生物防除剤 |
| US20050234119A1 (en) * | 2004-04-16 | 2005-10-20 | Soll Mark D | Antiparasitical agents and methods for treating, preventing and controlling external parasites in animals |
| FR2869905B1 (fr) * | 2004-05-10 | 2008-09-05 | Sanofi Synthelabo | Procede de preparation d'ester de l'acide 1,5-diphenylpyrazole carboxylique. |
| GB0413970D0 (en) * | 2004-06-22 | 2004-07-28 | Syngenta Participations Ag | Chemical compounds |
| UY28617A1 (es) * | 2004-11-12 | 2006-06-30 | Popley Pharma Ltda | Nuevas composiciones |
| US7923465B2 (en) | 2005-06-02 | 2011-04-12 | Glenmark Pharmaceuticals S.A. | Cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation |
| LT2957284T (lt) | 2007-06-27 | 2018-04-10 | E. I. Du Pont De Nemours And Company | Kovos su gyvūnų kenkėjais būdas |
| EP2364147A2 (en) | 2008-11-19 | 2011-09-14 | Merial Limited | Compositions comprising 1-arylpyrazole alone or in combination with formamidine for the treatment of parasitic infection |
| EP2364300B1 (en) * | 2008-11-19 | 2016-10-19 | Merial, Inc. | Dimeric 1-arylpyrazole derivatives |
| UA108641C2 (uk) | 2010-04-02 | 2015-05-25 | Паразитицидна композиція, яка містить чотири активних агенти, та спосіб її застосування | |
| JP5743418B2 (ja) * | 2010-04-09 | 2015-07-01 | Ｏａｔアグリオ株式会社 | 新規なピラゾール化合物、その製造方法及び有害生物防除剤 |
| CN104023720B (zh) | 2011-11-17 | 2016-10-26 | 梅里亚有限公司 | 包含芳基吡唑和取代咪唑的组合物，其方法和用途 |
| TWI579274B (zh) | 2012-04-20 | 2017-04-21 | 龍馬躍公司 | 製備１－芳基－５－烷基吡唑化合物的改良方法 |
| JP5943387B2 (ja) * | 2012-10-25 | 2016-07-05 | 国立大学法人 名古屋工業大学 | 新規トリフロン誘導体及びその製造方法 |
| EP3211998B1 (en) | 2014-10-31 | 2021-04-07 | Boehringer Ingelheim Animal Health USA Inc. | Parasiticidal composition comprising fipronil |
| US10766866B2 (en) | 2017-10-30 | 2020-09-08 | University Of North Texas Health Science Center At Fort Worth | Deterrents for arthropods and marine organisms |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8713768D0 (en) | 1987-06-12 | 1987-07-15 | May & Baker Ltd | Compositions of matter |
| US5232940A (en) | 1985-12-20 | 1993-08-03 | Hatton Leslie R | Derivatives of N-phenylpyrazoles |
| DE3617554A1 (de) * | 1986-05-24 | 1987-11-26 | Bayer Ag | 5-oxy(thio)-pyrazol-derivate |
| DE3625686A1 (de) | 1986-07-30 | 1988-02-04 | Bayer Ag | 4-cyano(nitro)-5-oxy(thio)-pyrazol-derivate |
| CA2004776C (fr) | 1988-12-13 | 2000-04-25 | Claude Wakselman | Procede de preparation de perfluoroalkylthioethers |
| US5079370A (en) | 1989-03-02 | 1992-01-07 | Rhone-Poulenc Ag Company | 1-arylpyrazoles |
| US4918085A (en) * | 1989-03-02 | 1990-04-17 | Rhone-Poulenc Ag Company | Pesticidal 3-cyano-5-alkoxy-1-arylpyrazoles, compositions and use |
| DE4023488A1 (de) * | 1990-07-24 | 1992-01-30 | Bayer Ag | 1-(pyri(mi)dyl-(2)) -5-hydroxy-pyrazol-mikrobizide |
| GB9306184D0 (en) | 1993-03-25 | 1993-05-19 | Zeneca Ltd | Heteroaromatic compounds |
| GB9601128D0 (en) | 1995-08-11 | 1996-03-20 | Pfizer Ltd | Parasiticidal compounds |
| FR2739255B1 (fr) | 1995-09-29 | 1998-09-04 | Rhone Merieux | Composition antiparasitaire pour le traitement et la protection des animaux de compagnie |
| WO1997028126A1 (en) | 1996-01-30 | 1997-08-07 | Takeda Chemical Industries, Ltd. | Arylpyrazole insecticides |
| GB9625045D0 (en) | 1996-11-30 | 1997-01-22 | Pfizer Ltd | Parasiticidal compounds |
| DE19650197A1 (de) | 1996-12-04 | 1998-06-10 | Bayer Ag | 3-Thiocarbamoylpyrazol-Derivate |
| TW524667B (en) | 1996-12-05 | 2003-03-21 | Pfizer | Parasiticidal pyrazoles |
| PL193231B1 (pl) | 1996-12-24 | 2007-01-31 | Basf Ag | Pochodna 3-acetylo-1-arylo-pirazolu i kompozycja szkodnikobójcza |
| US6350771B1 (en) | 1996-12-24 | 2002-02-26 | Rhone-Poulenc, Inc. | Pesticidal 1-arylpyrazoles |
| AP1004A (en) | 1996-12-24 | 2001-08-28 | Rhone Poulenc Agrochimie | Pesticidal 1-aryl and pyridylpyrazole derivatives. |
| JPH11246555A (ja) * | 1997-10-31 | 1999-09-14 | Sumitomo Chem Co Ltd | フッ素置換ベンゾヘテロ環化合物 |
| JP2000169453A (ja) * | 1998-09-30 | 2000-06-20 | Mitsubishi Chemicals Corp | １―フェニルピラゾ―ル―３―カルボキサミド誘導体、その中間体およびこれを有効成分とする農薬 |
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2000
- 2000-12-01 MY MYPI20005663A patent/MY129771A/en unknown
- 2000-12-01 ES ES00993256T patent/ES2409630T3/es not_active Expired - Lifetime
- 2000-12-01 IL IL14985600A patent/IL149856A0/xx active IP Right Grant
- 2000-12-01 CN CNA2006101356663A patent/CN1939909A/zh active Pending
- 2000-12-01 EP EP00993256A patent/EP1237873B1/en not_active Expired - Lifetime
- 2000-12-01 PL PL00364874A patent/PL364874A1/xx not_active IP Right Cessation
- 2000-12-01 BR BR0015945-0A patent/BR0015945A/pt not_active Application Discontinuation
- 2000-12-01 AU AU28393/01A patent/AU784798B2/en not_active Expired
- 2000-12-01 CO CO00091998A patent/CO5261614A1/es not_active Application Discontinuation
- 2000-12-01 CA CA002393197A patent/CA2393197C/en not_active Expired - Lifetime
- 2000-12-01 KR KR1020027006979A patent/KR100816914B1/ko not_active Expired - Fee Related
- 2000-12-01 MX MXPA02005511A patent/MXPA02005511A/es active IP Right Grant
- 2000-12-01 CN CN00816524A patent/CN1402713A/zh active Pending
- 2000-12-01 JP JP2001541880A patent/JP2003516941A/ja active Pending
- 2000-12-01 HU HU0300357A patent/HUP0300357A3/hu unknown
- 2000-12-01 WO PCT/EP2000/012100 patent/WO2001040195A2/en not_active Ceased
- 2000-12-01 CZ CZ20021898A patent/CZ20021898A3/cs unknown
- 2000-12-02 TW TW089125709A patent/TWI290137B/zh not_active IP Right Cessation
- 2000-12-04 US US09/727,684 patent/US6569886B2/en not_active Expired - Lifetime
- 2000-12-04 AR ARP000106403A patent/AR033504A1/es unknown
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2002
- 2002-05-26 IL IL149856A patent/IL149856A/en unknown
- 2002-05-30 ZA ZA200204336A patent/ZA200204336B/xx unknown
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2003
- 2003-04-04 US US10/406,491 patent/US6992099B2/en not_active Expired - Lifetime
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2005
- 2005-09-27 US US11/235,087 patent/US20060020013A1/en not_active Abandoned
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2006
- 2006-09-29 US US11/529,778 patent/US7468381B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2003516941A (ja) | 2003-05-20 |
| US7468381B2 (en) | 2008-12-23 |
| US20020111352A1 (en) | 2002-08-15 |
| CN1402713A (zh) | 2003-03-12 |
| MXPA02005511A (es) | 2004-09-10 |
| WO2001040195A2 (en) | 2001-06-07 |
| US6569886B2 (en) | 2003-05-27 |
| ZA200204336B (en) | 2003-03-20 |
| PL364874A1 (en) | 2004-12-27 |
| AU2839301A (en) | 2001-06-12 |
| KR20030016204A (ko) | 2003-02-26 |
| CO5261614A1 (es) | 2003-03-31 |
| EP1237873B1 (en) | 2013-04-03 |
| CA2393197A1 (en) | 2001-06-07 |
| US20030176466A1 (en) | 2003-09-18 |
| MY129771A (en) | 2007-04-30 |
| ES2409630T3 (es) | 2013-06-27 |
| KR100816914B1 (ko) | 2008-03-26 |
| US20070078127A1 (en) | 2007-04-05 |
| AR033504A1 (es) | 2003-12-26 |
| CZ20021898A3 (cs) | 2003-04-16 |
| US6992099B2 (en) | 2006-01-31 |
| HUP0300357A3 (en) | 2009-01-28 |
| WO2001040195A3 (en) | 2001-11-08 |
| US20060020013A1 (en) | 2006-01-26 |
| AU784798B2 (en) | 2006-06-22 |
| HUP0300357A2 (hu) | 2003-07-28 |
| TWI290137B (en) | 2007-11-21 |
| EP1237873A2 (en) | 2002-09-11 |
| CN1939909A (zh) | 2007-04-04 |
| IL149856A0 (en) | 2002-11-10 |
| IL149856A (en) | 2009-02-11 |
| BR0015945A (pt) | 2002-11-12 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20201201 |