JP6066910B2 - 殺菌・殺カビ性ピラゾール - Google Patents
殺菌・殺カビ性ピラゾール Download PDFInfo
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- JP6066910B2 JP6066910B2 JP2013527253A JP2013527253A JP6066910B2 JP 6066910 B2 JP6066910 B2 JP 6066910B2 JP 2013527253 A JP2013527253 A JP 2013527253A JP 2013527253 A JP2013527253 A JP 2013527253A JP 6066910 B2 JP6066910 B2 JP 6066910B2
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- Prior art keywords
- compound
- alkyl
- independently
- methyl
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- 230000000855 fungicidal effect Effects 0.000 title description 127
- 230000000844 anti-bacterial effect Effects 0.000 title description 36
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims description 685
- -1 cyanomethyl Chemical group 0.000 claims description 205
- 125000001424 substituent group Chemical group 0.000 claims description 139
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 85
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 83
- 229910052736 halogen Inorganic materials 0.000 claims description 73
- 150000002367 halogens Chemical class 0.000 claims description 70
- 229910052799 carbon Inorganic materials 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 56
- 125000004970 halomethyl group Chemical group 0.000 claims description 50
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 44
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 37
- 229910052760 oxygen Inorganic materials 0.000 claims description 35
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 35
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 31
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 30
- 125000004414 alkyl thio group Chemical group 0.000 claims description 29
- 229910052794 bromium Inorganic materials 0.000 claims description 27
- 229910052801 chlorine Inorganic materials 0.000 claims description 27
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 27
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 22
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 21
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 18
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 17
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 17
- 125000004076 pyridyl group Chemical group 0.000 claims description 17
- 125000001188 haloalkyl group Chemical group 0.000 claims description 15
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 12
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 11
- 125000002883 imidazolyl group Chemical group 0.000 claims description 10
- 229910052700 potassium Inorganic materials 0.000 claims description 10
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 229910052744 lithium Inorganic materials 0.000 claims description 5
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 4
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 4
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000000417 fungicide Substances 0.000 description 314
- 239000000203 mixture Substances 0.000 description 146
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 132
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 82
- 230000009471 action Effects 0.000 description 68
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- 239000011541 reaction mixture Substances 0.000 description 55
- 238000002360 preparation method Methods 0.000 description 52
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 46
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 37
- 239000000047 product Substances 0.000 description 32
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 201000010099 disease Diseases 0.000 description 30
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
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- 238000012360 testing method Methods 0.000 description 27
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- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 25
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 25
- 239000003899 bactericide agent Substances 0.000 description 25
- 229940126086 compound 21 Drugs 0.000 description 25
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- 239000000725 suspension Substances 0.000 description 25
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 24
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 24
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 24
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 24
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 24
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 24
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- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 24
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- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 23
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Classifications
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- 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
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- 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
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- 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
- C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- 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
- C07D231/18—One oxygen or sulfur atom
-
- 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
- C07D231/38—Nitrogen atoms
-
- 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
- C07D401/02—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 two hetero rings
- C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
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- 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
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- 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37915910P | 2010-09-01 | 2010-09-01 | |
| US61/379,159 | 2010-09-01 | ||
| PCT/US2011/049908 WO2012030922A1 (en) | 2010-09-01 | 2011-08-31 | Fungicidal pyrazoles |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013536856A JP2013536856A (ja) | 2013-09-26 |
| JP2013536856A5 JP2013536856A5 (enExample) | 2014-10-09 |
| JP6066910B2 true JP6066910B2 (ja) | 2017-01-25 |
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| EP (1) | EP2611297B1 (enExample) |
| JP (1) | JP6066910B2 (enExample) |
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| WO (1) | WO2012030922A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR075713A1 (es) | 2009-03-03 | 2011-04-20 | Du Pont | Pirazoles fungicidas |
| TWI504350B (zh) | 2010-09-01 | 2015-10-21 | Du Pont | 殺真菌吡唑及其混合物 |
| TWI568721B (zh) | 2012-02-01 | 2017-02-01 | 杜邦股份有限公司 | 殺真菌之吡唑混合物 |
| US20140235689A1 (en) * | 2013-02-20 | 2014-08-21 | E I Du Pont De Nemours And Company | Fungicidal pyrazoles |
| WO2014157569A1 (ja) | 2013-03-28 | 2014-10-02 | 武田薬品工業株式会社 | 複素環化合物 |
| TWI652012B (zh) * | 2013-05-20 | 2019-03-01 | 杜邦股份有限公司 | 殺真菌吡唑的固態形式 |
| WO2015026646A1 (en) | 2013-08-20 | 2015-02-26 | E. I. Du Pont De Nemours And Company | Fungicidal pyrazoles |
| EA201690737A1 (ru) | 2013-12-05 | 2016-10-31 | Куреха Корпорейшн | Сельскохозяйственное или садоводческое химическое средство, способ борьбы с болезнями растений и продукт для борьбы с болезнями растений |
| WO2015083437A1 (ja) * | 2013-12-05 | 2015-06-11 | 株式会社クレハ | 農園芸用薬剤、植物病害防除方法および植物病害防除用製品 |
| WO2015089800A1 (en) | 2013-12-19 | 2015-06-25 | Eli Lilly And Company | Fluorophenyl pyrazol compounds |
| CN106458925A (zh) * | 2014-05-06 | 2017-02-22 | 杜邦公司 | 杀真菌吡唑类 |
| JP2017522334A (ja) | 2014-07-24 | 2017-08-10 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 殺真菌性ピラゾール誘導体 |
| EP3271336A1 (en) | 2015-03-19 | 2018-01-24 | E. I. du Pont de Nemours and Company | Fungicidal pyrazoles |
| WO2016201662A1 (en) * | 2015-06-18 | 2016-12-22 | Eli Lilly And Company | Fluoropyridyl pyrazol compounds |
| EP3412658A1 (en) * | 2017-06-09 | 2018-12-12 | Solvay Sa | Processes for the manufacture of sulfur-substitued pyrazole derivatives |
| BR112022007294A2 (pt) * | 2019-10-18 | 2022-07-05 | Fmc Corp | Métodos para a preparação de ácido 5-bromo-2-(3-cloro-piridin-2-il)-2h-pirazol-3-carboxílico |
| IL291939B2 (en) * | 2019-10-18 | 2023-04-01 | Fmc Corp | Method for preparing 5-bromo-2-(3-chloro-pyridin-2-yl)-2h-pyralose-3-carboxylic acid |
| TW202241859A (zh) * | 2021-01-29 | 2022-11-01 | 美商富曼西公司 | 用於製備5-溴-2-(3-氯-吡啶-2-基)-2h-吡唑-3-甲酸之方法 |
| WO2024150100A1 (en) * | 2023-01-09 | 2024-07-18 | Fluorinnovation L.L.C-Fz | New process for manufacturing of 3-halomethyl-substituted 1-methyl-1h-pyrazole-4-carbonitriles and of derivatives thereof, and intermediates therefore |
| CN116606263B (zh) * | 2023-05-26 | 2025-06-13 | 青岛科技大学 | 一种含氟苯联噻唑双酯类化合物及其用途 |
| WO2025168620A1 (en) * | 2024-02-07 | 2025-08-14 | Bayer Aktiengesellschaft | Heteroaryl-substituted 4,5-dihydro-1h-2,4,5-oxadiazines as novel fungicides |
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| US3235361A (en) | 1962-10-29 | 1966-02-15 | Du Pont | Method for the control of undesirable vegetation |
| US3060084A (en) | 1961-06-09 | 1962-10-23 | Du Pont | Improved homogeneous, readily dispersed, pesticidal concentrate |
| US3299566A (en) | 1964-06-01 | 1967-01-24 | Olin Mathieson | Water soluble film containing agricultural chemicals |
| US3309192A (en) | 1964-12-02 | 1967-03-14 | Du Pont | Method of controlling seedling weed grasses |
| US4144050A (en) | 1969-02-05 | 1979-03-13 | Hoechst Aktiengesellschaft | Micro granules for pesticides and process for their manufacture |
| US3920442A (en) | 1972-09-18 | 1975-11-18 | Du Pont | Water-dispersible pesticide aggregates |
| JPS5527916B2 (enExample) * | 1973-02-05 | 1980-07-24 | ||
| CA1060892A (en) * | 1974-11-06 | 1979-08-21 | Parke, Davis And Company | Diazepine compounds and method for their production |
| US4172714A (en) | 1976-12-20 | 1979-10-30 | E. I. Du Pont De Nemours And Company | Dry compactible, swellable herbicidal compositions and pellets produced therefrom |
| DE3246493A1 (de) | 1982-12-16 | 1984-06-20 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von wasserdispergierbaren granulaten |
| AU559935B2 (en) * | 1983-02-04 | 1987-03-26 | Warner-Lambert Company | Imidazolyl-pyrazolyl methanone derivatives |
| JPS6253970A (ja) * | 1985-09-03 | 1987-03-09 | Nippon Nohyaku Co Ltd | ピラゾ−ル誘導体及びその製法 |
| US5180587A (en) | 1988-06-28 | 1993-01-19 | E. I. Du Pont De Nemours And Company | Tablet formulations of pesticides |
| DK0415688T3 (da) | 1989-08-30 | 1999-08-23 | Aeci Ltd | Fremgangsmåde til fremstilling af et doseringssystem samt fremgangsmåde til behandling af en genstand eller et locus |
| JPH03141276A (ja) * | 1989-10-24 | 1991-06-17 | Nissan Chem Ind Ltd | 置換ピラゾール誘導体および農園芸用殺菌剤 |
| PL167613B1 (pl) | 1990-03-12 | 1995-09-30 | Du Pont | Granulowana kompozycja rozpuszczalna lub dyspergowalna w wodzie PL |
| US5189040A (en) * | 1990-05-28 | 1993-02-23 | Sumitomo Chemical Company, Limited | Pyrazole derivatives, method for producing the same and agricultural and/or horticultural fungicides containing the same as active ingredient |
| JPH04356480A (ja) * | 1990-05-28 | 1992-12-10 | Sumitomo Chem Co Ltd | ピラゾール誘導体、その製造法およびそれを有効成分とする農園芸用殺菌剤 |
| EP0480679B1 (en) | 1990-10-11 | 1996-09-18 | Sumitomo Chemical Company Limited | Pesticidal composition |
| JPH0532662A (ja) * | 1990-11-09 | 1993-02-09 | Nissan Chem Ind Ltd | 置換ピラゾール誘導体および農園芸用殺菌剤 |
| JPH0551304A (ja) | 1991-06-10 | 1993-03-02 | Nippon Bayeragrochem Kk | 除草剤組成物 |
| JPH05279339A (ja) * | 1992-01-22 | 1993-10-26 | Nissan Chem Ind Ltd | 置換ピラゾール誘導体および農園芸用殺菌剤 |
| JPH0665237A (ja) * | 1992-05-07 | 1994-03-08 | Nissan Chem Ind Ltd | 置換ピラゾール誘導体および農園芸用殺菌剤 |
| US5939559A (en) * | 1995-02-07 | 1999-08-17 | Nissan Chemical Industries, Ltd. | Pyrazole derivative and herbicidal composition |
| JP2865599B2 (ja) | 1995-10-09 | 1999-03-08 | 株式会社横井製作所 | 埋設物の探査方法 |
| DE10136065A1 (de) | 2001-07-25 | 2003-02-13 | Bayer Cropscience Ag | Pyrazolylcarboxanilide |
| TW200724033A (en) | 2001-09-21 | 2007-07-01 | Du Pont | Anthranilamide arthropodicide treatment |
| CA2652859A1 (en) | 2006-06-21 | 2007-12-27 | E.I. Du Pont De Nemours And Company | Pyrazinones as cellular proliferation inhibitors |
| GB0713479D0 (en) | 2007-07-11 | 2007-08-22 | Syngenta Participations Ag | Substituted aromatic heterocyclic compounds as fungicides |
| PE20091953A1 (es) * | 2008-05-08 | 2010-01-09 | Du Pont | Azoles sustituidos como fungicidas |
| AR075713A1 (es) | 2009-03-03 | 2011-04-20 | Du Pont | Pirazoles fungicidas |
| WO2012023143A1 (en) | 2010-08-19 | 2012-02-23 | E. I. Du Pont De Nemours And Company | Fungicidal pyrazoles |
| TWI504350B (zh) | 2010-09-01 | 2015-10-21 | Du Pont | 殺真菌吡唑及其混合物 |
-
2011
- 2011-08-26 TW TW100130635A patent/TW201245155A/zh unknown
- 2011-08-31 BR BR122017015898-8A patent/BR122017015898B1/pt not_active IP Right Cessation
- 2011-08-31 CN CN201180042397.5A patent/CN103079406B/zh not_active Expired - Fee Related
- 2011-08-31 UY UY33582A patent/UY33582A/es not_active Application Discontinuation
- 2011-08-31 MX MX2013002400A patent/MX2013002400A/es not_active Application Discontinuation
- 2011-08-31 KR KR20137008060A patent/KR20130139892A/ko not_active Withdrawn
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- 2011-08-31 CN CN201510578968.7A patent/CN105130900B/zh not_active Expired - Fee Related
- 2011-08-31 JP JP2013527253A patent/JP6066910B2/ja not_active Expired - Fee Related
- 2011-08-31 US US13/816,847 patent/US8754115B2/en not_active Expired - Fee Related
- 2011-08-31 WO PCT/US2011/049908 patent/WO2012030922A1/en not_active Ceased
- 2011-08-31 EP EP11757463.2A patent/EP2611297B1/en not_active Not-in-force
- 2011-08-31 BR BR112013004835-2A patent/BR112013004835B1/pt not_active IP Right Cessation
- 2011-08-31 AU AU2011295998A patent/AU2011295998A1/en not_active Abandoned
- 2011-08-31 PL PL11757463T patent/PL2611297T3/pl unknown
- 2011-09-01 AR ARP110103199 patent/AR082869A1/es unknown
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2014
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Also Published As
| Publication number | Publication date |
|---|---|
| BR112013004835A2 (pt) | 2016-05-31 |
| PL2611297T3 (pl) | 2015-11-30 |
| US20130143940A1 (en) | 2013-06-06 |
| BR112013004835B1 (pt) | 2018-01-09 |
| EP2611297A1 (en) | 2013-07-10 |
| KR20130139892A (ko) | 2013-12-23 |
| TW201245155A (en) | 2012-11-16 |
| UY33582A (es) | 2012-03-30 |
| CN105130900A (zh) | 2015-12-09 |
| CN103079406B (zh) | 2016-03-30 |
| US9131693B2 (en) | 2015-09-15 |
| AU2011295998A1 (en) | 2013-02-21 |
| US8754115B2 (en) | 2014-06-17 |
| JP2013536856A (ja) | 2013-09-26 |
| US20140221448A1 (en) | 2014-08-07 |
| WO2012030922A1 (en) | 2012-03-08 |
| MX2013002400A (es) | 2013-06-05 |
| BR122017015898B1 (pt) | 2018-05-15 |
| ES2546671T3 (es) | 2015-09-25 |
| AR082869A1 (es) | 2013-01-16 |
| EP2611297B1 (en) | 2015-06-17 |
| CN103079406A (zh) | 2013-05-01 |
| CN105130900B (zh) | 2018-05-22 |
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