CA2826067A1 - Isoxazoline derivatives for controlling invertebrate pests - Google Patents
Isoxazoline derivatives for controlling invertebrate pests Download PDFInfo
- Publication number
- CA2826067A1 CA2826067A1 CA2826067A CA2826067A CA2826067A1 CA 2826067 A1 CA2826067 A1 CA 2826067A1 CA 2826067 A CA2826067 A CA 2826067A CA 2826067 A CA2826067 A CA 2826067A CA 2826067 A1 CA2826067 A1 CA 2826067A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- mono
- halogen
- cyano
- alkoxy
- 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.)
- Abandoned
Links
- 150000002547 isoxazolines Chemical class 0.000 title abstract description 5
- 241000607479 Yersinia pestis Species 0.000 title description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 95
- 241001465754 Metazoa Species 0.000 claims abstract description 46
- 150000003839 salts Chemical group 0.000 claims abstract description 20
- 244000045947 parasite Species 0.000 claims abstract description 19
- -1 hydroxy- Chemical class 0.000 claims description 118
- 229910052736 halogen Inorganic materials 0.000 claims description 76
- 150000002367 halogens Chemical class 0.000 claims description 76
- 239000000203 mixture Substances 0.000 claims description 58
- 150000003254 radicals Chemical class 0.000 claims description 51
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 48
- 239000004480 active ingredient Substances 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 32
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 25
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000004076 pyridyl group Chemical group 0.000 claims description 19
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 18
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 18
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 18
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 17
- 150000001204 N-oxides Chemical class 0.000 claims description 16
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 15
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 14
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 14
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 13
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 13
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 12
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 12
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 12
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 11
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 10
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000000335 thiazolyl group Chemical group 0.000 claims description 9
- 125000002053 thietanyl group Chemical group 0.000 claims description 9
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 8
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 8
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 6
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 6
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 229910052721 tungsten Inorganic materials 0.000 claims description 6
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims description 5
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 5
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000004306 triazinyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 244000078703 ectoparasite Species 0.000 abstract description 9
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 26
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- 239000007787 solid Substances 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
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- 238000009472 formulation Methods 0.000 description 18
- 125000001424 substituent group Chemical group 0.000 description 18
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 17
- 230000000694 effects Effects 0.000 description 16
- 125000000623 heterocyclic group Chemical group 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
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- 229920006395 saturated elastomer Polymers 0.000 description 14
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- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 12
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
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- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 239000004540 pour-on Substances 0.000 description 11
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- 239000004544 spot-on Substances 0.000 description 10
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- 229910052794 bromium Inorganic materials 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
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- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- QGLITUFXHVRMGV-UHFFFAOYSA-M sodium;tetratriacontyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCOS([O-])(=O)=O QGLITUFXHVRMGV-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000001590 sorbitan monolaureate Substances 0.000 description 1
- 235000011067 sorbitan monolaureate Nutrition 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 239000003351 stiffener Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004548 suspo-emulsion Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 229960001479 tosylchloramide sodium Drugs 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000005019 zein Substances 0.000 description 1
- 229940093612 zein Drugs 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
-
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A01N43/80—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- 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
- A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- 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
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (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 |
|---|---|---|---|
| CH2472011 | 2011-02-10 | ||
| CH00247/2011 | 2011-02-10 | ||
| PCT/EP2012/052241 WO2012107533A1 (en) | 2011-02-10 | 2012-02-09 | Isoxazoline derivatives for controlling invertebrate pests |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2826067A1 true CA2826067A1 (en) | 2012-08-16 |
Family
ID=45607737
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2826067A Abandoned CA2826067A1 (en) | 2011-02-10 | 2012-02-09 | Isoxazoline derivatives for controlling invertebrate pests |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US20130324538A1 (enExample) |
| EP (1) | EP2673273A1 (enExample) |
| JP (1) | JP2014505089A (enExample) |
| CN (1) | CN103347880B (enExample) |
| AR (1) | AR085354A1 (enExample) |
| AU (1) | AU2012215440B2 (enExample) |
| BR (1) | BR112013020520A2 (enExample) |
| CA (1) | CA2826067A1 (enExample) |
| CL (1) | CL2013002296A1 (enExample) |
| CO (1) | CO6731114A2 (enExample) |
| MX (1) | MX2013009211A (enExample) |
| RU (1) | RU2013141413A (enExample) |
| TW (1) | TWI511966B (enExample) |
| WO (1) | WO2012107533A1 (enExample) |
| ZA (1) | ZA201305226B (enExample) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UY33403A (es) * | 2010-06-17 | 2011-12-30 | Novartis Ag | Compuestos orgánicos con novedosas isoxazolinas, sus n-óxidos, s-óxidos y sales |
| AR086113A1 (es) * | 2011-04-30 | 2013-11-20 | Abbott Lab | Isoxazolinas como agentes terapeuticos |
| WO2012155352A1 (en) * | 2011-05-19 | 2012-11-22 | Eli Lilly And Company | Dihydroisoxazole compounds, parasiticidal uses and formulations thereof |
| AP2014007874A0 (en) | 2012-02-06 | 2014-08-31 | Merial Ltd | Parasiticidal oral veterinary compositions comprising systemetically- acting active agents, methods and uses thereof |
| JO3626B1 (ar) | 2012-02-23 | 2020-08-27 | Merial Inc | تركيبات موضعية تحتوي على فيبرونيل و بيرميثرين و طرق استخدامها |
| PT2953942T (pt) | 2013-02-06 | 2018-01-17 | Bayer Cropscience Ag | Derivados de pirazol substituídos com halogéneo como agentes pesticidas |
| WO2014206909A1 (en) | 2013-06-24 | 2014-12-31 | Basf Se | Thiophene- or furan-substituted isothiazoline compounds as pesticides |
| WO2015066277A1 (en) | 2013-11-01 | 2015-05-07 | Merial Limited | Antiparisitic and pesticidal isoxazoline compounds |
| MX373872B (es) | 2013-12-20 | 2020-03-26 | Intervet Int Bv | Composiciones de isoxazolina y uso de las mismas en la prevención o tratamiento de infestaciones parasitarias en animales. |
| ES2874054T3 (es) | 2013-12-20 | 2021-11-04 | Intervet Int Bv | Uso de derivados de isoxazolina para el tratamiento o la prevención de la infestación con artrópodos en aves de corral |
| WO2015101622A1 (de) | 2014-01-03 | 2015-07-09 | Bayer Cropscience Ag | Neue pyrazolyl-heteroarylamide als schädlingsbekämpfungsmittel |
| JP6682719B2 (ja) | 2014-04-17 | 2020-04-15 | ベーリンガー インゲルハイム アニマル ヘルス ユーエスエイ インコーポレイテッド | 寄生生物から動物を保護するためのマロノニトリル化合物の使用 |
| JP2017521441A (ja) | 2014-07-15 | 2017-08-03 | バイエル・アニマル・ヘルス・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ａｎｉｍａｌ Ｈｅａｌｔｈ Ｇｍｂｈ | 有害生物防除剤としてのアリール−トリアゾリルピリジン類 |
| US20170232024A1 (en) | 2014-08-04 | 2017-08-17 | Jerry Tan Eye Surgery Pte Ltd | Pharmaceutical compositions for demodex related blepharitis and eyelid crusting |
| EP3018129A1 (en) * | 2014-11-10 | 2016-05-11 | Novartis Tiergesundheit AG | Diaryl isoxazoline compound |
| UY36570A (es) * | 2015-02-26 | 2016-10-31 | Merial Inc | Formulaciones inyectables de acción prolongada que comprenden un agente activo isoxazolina, métodos y usos de las mismas |
| CA2981797C (en) * | 2015-04-08 | 2023-11-21 | Merial, Inc. | Extended release injectable formulations comprising an isoxazoline active agent, methods and uses thereof |
| RS62130B1 (sr) | 2015-05-20 | 2021-08-31 | Boehringer Ingelheim Animal Health Usa Inc | Antihelmintička depsipeptidna jedinjenja |
| UY37137A (es) | 2016-02-24 | 2017-09-29 | Merial Inc | Compuestos antiparasitarios de isoxazolina, formulaciones inyectables de acción prolongada que los comprenden, métodos y usos de los mismos |
| EP3497101B1 (de) * | 2016-08-10 | 2020-12-30 | Bayer CropScience Aktiengesellschaft | Substituierte 2-heterocyclyl-imidazolyl-carboxamide als schädlingsbekämpfungsmittel |
| JP2019535655A (ja) | 2016-10-14 | 2019-12-12 | ベーリンガー インゲルハイム アニマル ヘルス ユーエスエイ インコーポレイテッド | 殺虫性及び殺寄生虫性ビニルイソオキサゾリン化合物 |
| BR112019009977A2 (pt) | 2016-11-16 | 2019-08-27 | Boehringer Ingelheim Animal Health Usa Inc | compostos depsipeptídicos anti-helmínticos |
| WO2018166855A1 (en) | 2017-03-16 | 2018-09-20 | Basf Se | Heterobicyclic substituted dihydroisoxazoles |
| MX2020001724A (es) | 2017-08-14 | 2020-07-29 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos de pirazol-isoxazolina plaguicidas y parasiticidas. |
| CN119157876A (zh) | 2017-12-15 | 2024-12-20 | 塔苏斯制药有限公司 | 用于治疗睑炎的异恶唑啉驱虫剂制剂和方法 |
| TWI812673B (zh) * | 2018-02-12 | 2023-08-21 | 美商富曼西公司 | 用於防治無脊椎害蟲之萘異噁唑啉化合物 |
| MX2021000293A (es) | 2018-07-09 | 2021-07-15 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos heterociclicos antihelminticos. |
| EP3846793B1 (en) | 2018-09-07 | 2024-01-24 | PIC Therapeutics, Inc. | Eif4e inhibitors and uses thereof |
| US11773066B2 (en) | 2018-11-20 | 2023-10-03 | Boehringer Ingelheim Animal Health USA Inc. | Indazolylcyanoethylamino compound, compositions of same, method of making, and methods of using thereof |
| KR20220002890A (ko) | 2019-03-19 | 2022-01-07 | 뵈링거 잉겔하임 애니멀 헬스 유에스에이 인코포레이티드 | 구충성 아자-벤조티오펜 및 아자-벤조푸란 화합물 |
| US12502377B2 (en) | 2019-04-04 | 2025-12-23 | Tarsus Pharmaceuticals, Inc. | Method of eradicating ticks that attach to humans using lotilaner formulations |
| US20220249445A1 (en) * | 2019-06-19 | 2022-08-11 | Tarsus Pharmaceuticals, Inc. | Isoxazoline parasiticide formulations and methods for treating blepharitis |
| JP2022537389A (ja) * | 2019-06-19 | 2022-08-25 | ターサス ファーマシューティカルズ， インコーポレイテッド | 眼瞼炎を治療するためのイソキサゾリン寄生虫駆除剤の処方及び方法 |
| TW202142235A (zh) * | 2020-01-29 | 2021-11-16 | 德商拜耳動物保健有限公司 | 用於控制非人類生物體上之寄生蟲之醫藥組成物 |
| AR121506A1 (es) | 2020-03-03 | 2022-06-08 | Pic Therapeutics Inc | Inhibidores del eif4e y sus usos |
| BR112022024156A2 (pt) | 2020-05-29 | 2023-02-14 | Boehringer Ingelheim Animal Health Usa Inc | Compostos heterocílicos antelmínticos |
| US12655090B2 (en) | 2021-01-27 | 2026-06-16 | Intervet Inc. | Cyclopropylamide compounds against parasites in fish |
| US20240316045A1 (en) | 2021-01-27 | 2024-09-26 | Intervet Inc. | Cyclopropylamide compounds against parasites in fish |
| CA3224701A1 (en) * | 2021-08-11 | 2023-02-16 | Jingdan Hu | Process for making diaryl isoxazoline derivative |
| IL310924A (en) | 2021-08-25 | 2024-04-01 | Pic Therapeutics Inc | Eif4e inhibitors and uses thereof |
| US12157732B2 (en) | 2021-08-25 | 2024-12-03 | PIC Therapeutics, Inc. | eIF4E inhibitors and uses thereof |
| WO2023073641A1 (en) | 2021-11-01 | 2023-05-04 | Boehringer Ingelheim Vetmedica Gmbh | Anthelmintic pyrrolopyridazine compounds |
| US12258193B2 (en) | 2022-02-17 | 2025-03-25 | Boehringer Ingelheim Vetmedica Gmbh | Method and system for providing a fluid product mailer |
| CN114853748A (zh) * | 2022-05-06 | 2022-08-05 | 武汉工程大学 | 一种含三氟甲烷异噁唑啉类衍生物、其制备方法和应用 |
| NO20240925A1 (en) | 2023-09-15 | 2025-03-17 | Evah Atlantic Inc | Dihydroisoxazole compound for use in reducing ectoparasite infestations on fish |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4026018A1 (de) * | 1990-08-17 | 1992-02-20 | Hoechst Ag | Isoxazoline oder isothiazoline enthaltende pflanzenschuetzende mittel und neue isoxazoline und isothiazoline |
| DE4331448A1 (de) * | 1993-09-16 | 1995-03-23 | Hoechst Schering Agrevo Gmbh | Substituierte Isoxazoline, Verfahren zu deren Herstellung, diese enthaltende Mittel und deren Verwendung als Safener |
| DE19935218A1 (de) * | 1999-07-27 | 2001-02-01 | Aventis Cropscience Gmbh | Isoxazolyl-substituierte Benzoylcyclohexandione, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| KR100606083B1 (ko) | 2004-11-04 | 2006-07-31 | 삼성전자주식회사 | 광대역 무선 접속 통신 시스템에서 부채널 할당 시스템 및 방법 |
| BRPI0617076B1 (pt) * | 2005-09-02 | 2021-07-06 | Nissan Chemical Corporation | Composto benzamida substituída por isoxazolina da fórmula (1) ou sal do mesmo; composto benzamida substituido por 4-hidroxiiminametila da fórmula (2) ou sal do mesmo; pesticida; agente agroquímico; parasiticida interno ou externo para mamíferos ou aves; inseticida ou acaricida |
| TW200803740A (en) * | 2005-12-16 | 2008-01-16 | Du Pont | 5-aryl isoxazolines for controlling invertebrate pests |
| TWI649303B (zh) | 2007-08-17 | 2019-02-01 | 杜邦股份有限公司 | 製備４-乙醯基-ｎ-〔２-側氧基-２-〔（２，２，２-三氟乙基）胺基〕乙基〕-１-萘甲醯胺之化合物及方法 |
| WO2009071500A2 (en) | 2007-12-03 | 2009-06-11 | Novartis Ag | Organic compounds |
| AR074790A1 (es) * | 2008-12-19 | 2011-02-09 | Novartis Ag | Derivados de isooxazol sustituidos, composiciones farmaceuticas y para el control de parasitos que los comprenden y su uso en metodos para controlar parasitos en y sobre animales de sangre caliente. |
-
2012
- 2012-02-09 CA CA2826067A patent/CA2826067A1/en not_active Abandoned
- 2012-02-09 RU RU2013141413/04A patent/RU2013141413A/ru not_active Application Discontinuation
- 2012-02-09 AU AU2012215440A patent/AU2012215440B2/en not_active Ceased
- 2012-02-09 CN CN201280008309.4A patent/CN103347880B/zh not_active Expired - Fee Related
- 2012-02-09 JP JP2013552962A patent/JP2014505089A/ja not_active Ceased
- 2012-02-09 AR ARP120100434A patent/AR085354A1/es unknown
- 2012-02-09 EP EP12704256.2A patent/EP2673273A1/en not_active Withdrawn
- 2012-02-09 WO PCT/EP2012/052241 patent/WO2012107533A1/en not_active Ceased
- 2012-02-09 MX MX2013009211A patent/MX2013009211A/es not_active Application Discontinuation
- 2012-02-09 US US13/984,701 patent/US20130324538A1/en not_active Abandoned
- 2012-02-09 BR BR112013020520A patent/BR112013020520A2/pt not_active IP Right Cessation
- 2012-02-10 TW TW101104306A patent/TWI511966B/zh not_active IP Right Cessation
-
2013
- 2013-07-11 ZA ZA2013/05226A patent/ZA201305226B/en unknown
- 2013-07-12 CO CO13165984A patent/CO6731114A2/es unknown
- 2013-08-07 CL CL2013002296A patent/CL2013002296A1/es unknown
-
2015
- 2015-10-01 US US14/872,669 patent/US20160024062A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| TWI511966B (zh) | 2015-12-11 |
| RU2013141413A (ru) | 2015-03-20 |
| CN103347880A (zh) | 2013-10-09 |
| JP2014505089A (ja) | 2014-02-27 |
| AR085354A1 (es) | 2013-09-25 |
| TW201309683A (zh) | 2013-03-01 |
| AU2012215440B2 (en) | 2015-08-27 |
| EP2673273A1 (en) | 2013-12-18 |
| US20130324538A1 (en) | 2013-12-05 |
| MX2013009211A (es) | 2013-08-29 |
| WO2012107533A1 (en) | 2012-08-16 |
| AU2012215440A1 (en) | 2013-08-01 |
| CO6731114A2 (es) | 2013-08-15 |
| US20160024062A1 (en) | 2016-01-28 |
| ZA201305226B (en) | 2014-03-26 |
| NZ613191A (en) | 2015-06-26 |
| CN103347880B (zh) | 2015-11-25 |
| CL2013002296A1 (es) | 2014-03-14 |
| BR112013020520A2 (pt) | 2016-07-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |
Effective date: 20180209 |