TW200808766A - Novel insecticides - Google Patents
Novel insecticides Download PDFInfo
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- TW200808766A TW200808766A TW096105429A TW96105429A TW200808766A TW 200808766 A TW200808766 A TW 200808766A TW 096105429 A TW096105429 A TW 096105429A TW 96105429 A TW96105429 A TW 96105429A TW 200808766 A TW200808766 A TW 200808766A
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- alkyl
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- 239000002917 insecticide Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 410
- 239000004480 active ingredient Substances 0.000 claims abstract description 47
- 150000003839 salts Chemical class 0.000 claims abstract description 42
- 239000000460 chlorine Substances 0.000 claims description 175
- -1 tri-substituted phenyl Chemical group 0.000 claims description 150
- 239000000203 mixture Substances 0.000 claims description 132
- 125000000217 alkyl group Chemical group 0.000 claims description 84
- 239000002253 acid Substances 0.000 claims description 56
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 150000002367 halogens Chemical class 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 241000238631 Hexapoda Species 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 229910052717 sulfur Inorganic materials 0.000 claims description 28
- 239000011593 sulfur Substances 0.000 claims description 28
- 150000001412 amines Chemical class 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 239000001301 oxygen Substances 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 25
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 25
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 125000001188 haloalkyl group Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 229920006395 saturated elastomer Polymers 0.000 claims description 16
- 239000005864 Sulphur Substances 0.000 claims description 14
- 241000607479 Yersinia pestis Species 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 10
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 9
- 125000002950 monocyclic group Chemical group 0.000 claims description 9
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 150000002923 oximes Chemical class 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 7
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000005265 dialkylamine group Chemical group 0.000 claims description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 5
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- 241001529936 Murinae Species 0.000 claims description 3
- 150000003973 alkyl amines Chemical class 0.000 claims description 3
- 238000001354 calcination Methods 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 239000012752 auxiliary agent Substances 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 2
- 229940067157 phenylhydrazine Drugs 0.000 claims description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 claims 1
- 206010035148 Plague Diseases 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
- 125000001909 leucine group Chemical group [H]N(*)C(C(*)=O)C([H])([H])C(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 230000001850 reproductive effect Effects 0.000 claims 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- 238000003419 tautomerization reaction Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 271
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 182
- 238000002360 preparation method Methods 0.000 description 125
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 120
- 235000019439 ethyl acetate Nutrition 0.000 description 112
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 70
- 239000007787 solid Substances 0.000 description 69
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 67
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 61
- 230000000694 effects Effects 0.000 description 59
- 239000002585 base Substances 0.000 description 58
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 56
- 238000006243 chemical reaction Methods 0.000 description 53
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 48
- 238000003818 flash chromatography Methods 0.000 description 40
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- 239000000047 product Substances 0.000 description 37
- 239000000126 substance Substances 0.000 description 37
- 239000003053 toxin Substances 0.000 description 37
- 231100000765 toxin Toxicity 0.000 description 37
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- 241000196324 Embryophyta Species 0.000 description 33
- 239000002904 solvent Substances 0.000 description 33
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 32
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 19
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 18
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
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- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 13
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 13
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- WCZKTXKOKMXREO-UHFFFAOYSA-N triethylsulfanium Chemical class CC[S+](CC)CC WCZKTXKOKMXREO-UHFFFAOYSA-N 0.000 description 1
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- GOTIICCWNAPLMN-UHFFFAOYSA-M trimethylsulfanium;bromide Chemical compound [Br-].C[S+](C)C GOTIICCWNAPLMN-UHFFFAOYSA-M 0.000 description 1
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- 229940071559 trioxin Drugs 0.000 description 1
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- FVECELJHCSPHKY-JLSHOZRYSA-N veratridine Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)O[C@@H]1[C@@]2(O)O[C@]34C[C@@]5(O)[C@H](CN6[C@@H](CC[C@H](C)C6)[C@@]6(C)O)[C@]6(O)[C@@H](O)C[C@@]5(O)[C@@H]4CC[C@H]2[C@]3(C)CC1 FVECELJHCSPHKY-JLSHOZRYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- 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
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
-
- 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
- A01N43/74—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 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- 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
- A01N43/72—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
- A01N43/86—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 1,3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- C07D417/14—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)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06003094 | 2006-02-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200808766A true TW200808766A (en) | 2008-02-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| TW096105429A TW200808766A (en) | 2006-02-16 | 2007-02-14 | Novel insecticides |
Country Status (21)
| Country | Link |
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| EP (1) | EP1984354B1 (https=) |
| JP (1) | JP2009526798A (https=) |
| KR (1) | KR20080093045A (https=) |
| CN (1) | CN101426779B (https=) |
| AR (1) | AR059494A1 (https=) |
| AT (1) | ATE438643T1 (https=) |
| AU (1) | AU2007214661B2 (https=) |
| BR (1) | BRPI0709555B1 (https=) |
| CA (1) | CA2640307A1 (https=) |
| DE (1) | DE602007001870D1 (https=) |
| EG (1) | EG25368A (https=) |
| ES (1) | ES2331437T3 (https=) |
| IL (1) | IL192930A0 (https=) |
| MA (1) | MA30262B1 (https=) |
| NZ (1) | NZ570099A (https=) |
| RU (1) | RU2437881C2 (https=) |
| TW (1) | TW200808766A (https=) |
| UA (1) | UA91406C2 (https=) |
| WO (1) | WO2007093402A1 (https=) |
| ZA (1) | ZA200806326B (https=) |
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| ATE498311T1 (de) | 2007-04-25 | 2011-03-15 | Syngenta Participations Ag | Fungizidzusammensetzungen |
| US8399490B2 (en) * | 2007-07-16 | 2013-03-19 | Syngenta Crop Protection Llc | Insecticides |
| WO2009021717A2 (en) * | 2007-08-14 | 2009-02-19 | Syngenta Participations Ag | Pesticidal formulation |
| GB0716414D0 (en) | 2007-08-22 | 2007-10-03 | Syngenta Participations Ag | Novel insecticides |
| TWI411395B (zh) * | 2007-12-24 | 2013-10-11 | Syngenta Participations Ag | 殺蟲化合物 |
| EP2331536B1 (en) | 2008-08-22 | 2013-08-21 | Syngenta Participations AG | Insecticidal compounds |
| JP2012500782A (ja) * | 2008-08-22 | 2012-01-12 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | 殺虫化合物類 |
| JP2012501989A (ja) * | 2008-09-04 | 2012-01-26 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | 殺虫化合物 |
| GB2463318A (en) * | 2008-09-12 | 2010-03-17 | Syngenta Participations Ag | Preparation of anthranilamide derivatives containing a pyridinylpyrazole moiety |
| GB2463736A (en) * | 2008-09-30 | 2010-03-31 | Syngenta Participations Ag | Process for the preparation of ortho amino-substituted aromatic carboxylic acids |
| WO2010083199A1 (en) * | 2009-01-19 | 2010-07-22 | Abbott Laboratories | Benzthiazole inhibitors of poly(adp-ribose)polymerase |
| KR20120089626A (ko) * | 2009-06-22 | 2012-08-13 | 신젠타 리미티드 | 살충제 화합물 |
| EP2531491A1 (en) | 2010-02-04 | 2012-12-12 | Syngenta Participations AG | Pyridazine derivatives, processes for their preparation and their use as fungicides |
| WO2011104183A1 (en) | 2010-02-24 | 2011-09-01 | Syngenta Participations Ag | Novel microbicides |
| CN103153958A (zh) | 2010-07-02 | 2013-06-12 | 先正达参股股份有限公司 | 新颖的杀微生物的二肟醚衍生物 |
| CN103038217A (zh) | 2010-07-29 | 2013-04-10 | 先正达参股股份有限公司 | 新颖的杀微生物的二肟醚衍生物 |
| WO2012066122A1 (en) | 2010-11-18 | 2012-05-24 | Syngenta Participations Ag | 2 - (pyridin- 2 -yl) -quinazoline derivatives and their use as microbicides |
| WO2012069652A2 (en) | 2010-11-26 | 2012-05-31 | Syngenta Participations Ag | Fungicide mixtures |
| WO2013011010A1 (en) | 2011-07-19 | 2013-01-24 | Syngenta Participations Ag | Fungizide mixtures |
| BR112014003186A2 (pt) | 2011-08-12 | 2017-04-04 | Basf Se | composto da fórmula geral (i), combinação pesticida, composição agrícola ou veterinária, método para combater ou controlar pragas invertebradas, método para a proteção de plantas e sementes, semente, uso de um composto e método para tratar um animal |
| UY34279A (es) | 2011-08-23 | 2013-04-05 | Syngenta Participations Ag | Compuestos heterocíclicos activos como microbiocidas, intermediarios, composiciones y usos |
| WO2014128136A1 (en) | 2013-02-20 | 2014-08-28 | Basf Se | Anthranilamide compounds and their use as pesticides |
| EP2964629A1 (de) | 2013-03-06 | 2016-01-13 | Bayer CropScience Aktiengesellschaft | Alkoximino substituierte anthranilsäurediamide als pestizide |
| RU2743074C2 (ru) | 2014-08-01 | 2021-02-15 | Нуэволюшон А/С | Соединения, активные по отношению к бромодоменам |
| CR20170418A (es) | 2015-03-27 | 2017-11-09 | Syngenta Participations Ag | Derivados heterobicíclicos microbicidas |
| UA125650C2 (uk) | 2016-09-09 | 2022-05-11 | Інсайт Корпорейшн | Регулятори нрk1 на основі похідних піразолопіридину та їх застосування для лікування раку |
| TW201811799A (zh) | 2016-09-09 | 2018-04-01 | 美商英塞特公司 | 吡唑并嘧啶化合物及其用途 |
| WO2018049214A1 (en) | 2016-09-09 | 2018-03-15 | Incyte Corporation | Pyrazolopyridine derivatives as hpk1 modulators and uses thereof for the treatment of cancer |
| US20180228786A1 (en) | 2017-02-15 | 2018-08-16 | Incyte Corporation | Pyrazolopyridine compounds and uses thereof |
| US10722495B2 (en) | 2017-09-08 | 2020-07-28 | Incyte Corporation | Cyanoindazole compounds and uses thereof |
| EP3728256B1 (en) | 2017-12-20 | 2024-10-02 | PI Industries Ltd. | Pyrazolopyridine-diamides, their use as insecticide and processes for preparing the same |
| WO2019123194A1 (en) | 2017-12-20 | 2019-06-27 | Pi Industries Ltd. | Anthranilamides, their use as insecticide and processes for preparing the same. |
| WO2019150220A1 (en) | 2018-01-30 | 2019-08-08 | Pi Industries Ltd. | Novel anthranilamides, their use as insecticide and processes for preparing the same. |
| WO2019164847A1 (en) | 2018-02-20 | 2019-08-29 | Incyte Corporation | Indazole compounds and uses thereof |
| US10745388B2 (en) | 2018-02-20 | 2020-08-18 | Incyte Corporation | Indazole compounds and uses thereof |
| US10800761B2 (en) | 2018-02-20 | 2020-10-13 | Incyte Corporation | Carboxamide compounds and uses thereof |
| US11299473B2 (en) | 2018-04-13 | 2022-04-12 | Incyte Corporation | Benzimidazole and indole compounds and uses thereof |
| US10899755B2 (en) | 2018-08-08 | 2021-01-26 | Incyte Corporation | Benzothiazole compounds and uses thereof |
| ES2973117T3 (es) | 2018-09-25 | 2024-06-18 | Incyte Corp | Compuestos de pirazolo[4,3-d]pirimidina como moduladores de ALK2 y/o FGFR |
| WO2021007477A1 (en) | 2019-07-11 | 2021-01-14 | E-Scape Bio, Inc. | Indazoles and azaindazoles as lrrk2 inhibitors |
| TWI904095B (zh) * | 2019-07-25 | 2025-11-11 | 印度商裘拉德製藥私人有限公司 | 乙醯輔酶a合成酶短鏈2(acss2)之小分子抑制劑 |
| MX2022001562A (es) | 2019-08-06 | 2022-04-26 | Incyte Corp | Formas solidas de un inhibidor de la cinasa 1 del progenitor hematopoyetico (hpk1). |
| CN110483403A (zh) * | 2019-09-02 | 2019-11-22 | 南通大学 | 一种5-溴-4-甲氧基-1h-吲唑的合成方法 |
| US11618751B1 (en) | 2022-03-25 | 2023-04-04 | Ventus Therapeutics U.S., Inc. | Pyrido-[3,4-d]pyridazine amine derivatives useful as NLRP3 derivatives |
| US11319319B1 (en) | 2021-04-07 | 2022-05-03 | Ventus Therapeutics U.S., Inc. | Compounds for inhibiting NLRP3 and uses thereof |
| CN115572282B (zh) * | 2021-07-05 | 2024-07-09 | 华东理工大学 | 含芳杂环结构的吡唑酰胺类化合物及其制备方法和应用 |
| EP4376616A1 (en) | 2021-07-27 | 2024-06-05 | Syngenta Crop Protection AG | Method for controlling diamide resistant pests & compounds therefor |
| US20240308988A1 (en) | 2021-08-05 | 2024-09-19 | Syngenta Crop Protection Ag | Method For Controlling Diamide Resistant Pests and Compounds Therefor |
| AU2022331725A1 (en) | 2021-08-19 | 2024-03-07 | Syngenta Crop Protection Ag | Method for controlling diamide resistant pests & compounds therefor |
| US12331048B2 (en) | 2022-10-31 | 2025-06-17 | Ventus Therapeutics U.S., Inc. | Pyrido-[3,4-d]pyridazine amine derivatives useful as NLRP3 inhibitors |
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| US674047A (en) * | 1900-04-19 | 1901-05-14 | Henry N Samstag | Engine. |
| RU2283840C2 (ru) * | 2001-08-13 | 2006-09-20 | Е.И.Дюпон Де Немур Энд Компани | Антраниламидное соединение, композиция для борьбы с насекомыми, композиция для борьбы с беспозвоночными вредителями, способы борьбы с насекомыми, промежуточные соединения |
| AR048669A1 (es) * | 2004-03-03 | 2006-05-17 | Syngenta Ltd | Derivados biciclicos de bisamida |
| GB0422556D0 (en) * | 2004-10-11 | 2004-11-10 | Syngenta Participations Ag | Novel insecticides |
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2007
- 2007-02-14 CA CA002640307A patent/CA2640307A1/en not_active Abandoned
- 2007-02-14 UA UAA200811094A patent/UA91406C2/ru unknown
- 2007-02-14 NZ NZ570099A patent/NZ570099A/en not_active IP Right Cessation
- 2007-02-14 AR ARP070100621A patent/AR059494A1/es not_active Application Discontinuation
- 2007-02-14 TW TW096105429A patent/TW200808766A/zh unknown
- 2007-02-14 AT AT07703468T patent/ATE438643T1/de not_active IP Right Cessation
- 2007-02-14 DE DE602007001870T patent/DE602007001870D1/de active Active
- 2007-02-14 JP JP2008554669A patent/JP2009526798A/ja active Pending
- 2007-02-14 EP EP07703468A patent/EP1984354B1/en not_active Not-in-force
- 2007-02-14 CN CN2007800110090A patent/CN101426779B/zh not_active Expired - Fee Related
- 2007-02-14 BR BRPI0709555A patent/BRPI0709555B1/pt not_active IP Right Cessation
- 2007-02-14 ES ES07703468T patent/ES2331437T3/es active Active
- 2007-02-14 WO PCT/EP2007/001283 patent/WO2007093402A1/en not_active Ceased
- 2007-02-14 AU AU2007214661A patent/AU2007214661B2/en not_active Expired - Fee Related
- 2007-02-14 US US12/278,807 patent/US8658801B2/en not_active Expired - Fee Related
- 2007-02-14 KR KR1020087019833A patent/KR20080093045A/ko not_active Ceased
- 2007-02-14 RU RU2008136750/04A patent/RU2437881C2/ru not_active IP Right Cessation
-
2008
- 2008-07-21 ZA ZA200806326A patent/ZA200806326B/xx unknown
- 2008-07-21 IL IL192930A patent/IL192930A0/en unknown
- 2008-08-13 EG EG2008081372A patent/EG25368A/xx active
- 2008-09-05 MA MA31211A patent/MA30262B1/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EG25368A (en) | 2011-12-20 |
| DE602007001870D1 (de) | 2009-09-17 |
| AU2007214661B2 (en) | 2012-05-17 |
| NZ570099A (en) | 2010-08-27 |
| JP2009526798A (ja) | 2009-07-23 |
| WO2007093402A1 (en) | 2007-08-23 |
| AU2007214661A1 (en) | 2007-08-23 |
| EP1984354B1 (en) | 2009-08-05 |
| CA2640307A1 (en) | 2007-08-23 |
| ES2331437T3 (es) | 2010-01-04 |
| CN101426779B (zh) | 2013-08-21 |
| US8658801B2 (en) | 2014-02-25 |
| RU2008136750A (ru) | 2010-03-27 |
| AR059494A1 (es) | 2008-04-09 |
| ATE438643T1 (de) | 2009-08-15 |
| ZA200806326B (en) | 2009-07-29 |
| CN101426779A (zh) | 2009-05-06 |
| KR20080093045A (ko) | 2008-10-17 |
| BRPI0709555A2 (pt) | 2011-07-19 |
| EP1984354A1 (en) | 2008-10-29 |
| US20090298816A1 (en) | 2009-12-03 |
| BRPI0709555B1 (pt) | 2015-11-03 |
| RU2437881C2 (ru) | 2011-12-27 |
| IL192930A0 (en) | 2009-02-11 |
| MA30262B1 (fr) | 2009-03-02 |
| UA91406C2 (ru) | 2010-07-26 |
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