JP5715646B2 - 殺菌・殺カビ性ヘテロ環式化合物 - Google Patents
殺菌・殺カビ性ヘテロ環式化合物 Download PDFInfo
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- JP5715646B2 JP5715646B2 JP2012548142A JP2012548142A JP5715646B2 JP 5715646 B2 JP5715646 B2 JP 5715646B2 JP 2012548142 A JP2012548142 A JP 2012548142A JP 2012548142 A JP2012548142 A JP 2012548142A JP 5715646 B2 JP5715646 B2 JP 5715646B2
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- 230000000844 anti-bacterial effect Effects 0.000 title claims description 89
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- -1 cyano, hydroxy Chemical group 0.000 claims description 230
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- 150000002367 halogens Chemical class 0.000 claims description 68
- 125000003545 alkoxy group Chemical group 0.000 claims description 60
- 150000001721 carbon Chemical group 0.000 claims description 59
- 150000003839 salts Chemical class 0.000 claims description 36
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 239000004094 surface-active agent Substances 0.000 claims description 20
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
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- LUWYYWRUWNBSGP-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]diazinan-1-yl]-2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]ethanone Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1NCC(C=2SC=C(N=2)C=2CC(ON=2)C=2C(=CC=CC=2F)F)CC1 LUWYYWRUWNBSGP-UHFFFAOYSA-N 0.000 claims description 2
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- OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 description 129
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- 125000001424 substituent group Chemical group 0.000 description 86
- 229910052799 carbon Inorganic materials 0.000 description 71
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 62
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- 125000000623 heterocyclic group Chemical group 0.000 description 49
- 150000001412 amines Chemical class 0.000 description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 47
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
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- 125000004122 cyclic group Chemical group 0.000 description 34
- 239000003921 oil Substances 0.000 description 34
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- 230000002829 reductive effect Effects 0.000 description 34
- 125000001624 naphthyl group Chemical group 0.000 description 33
- 239000000047 product Substances 0.000 description 33
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 29
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- 125000004432 carbon atom Chemical group C* 0.000 description 28
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
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- 241000233866 Fungi Species 0.000 description 26
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
- 239000002585 base Substances 0.000 description 26
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- 125000001188 haloalkyl group Chemical group 0.000 description 25
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 238000012360 testing method Methods 0.000 description 23
- 229940125782 compound 2 Drugs 0.000 description 22
- 230000012010 growth Effects 0.000 description 22
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000004480 active ingredient Substances 0.000 description 21
- 229940125904 compound 1 Drugs 0.000 description 21
- 229940126214 compound 3 Drugs 0.000 description 21
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 20
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 19
- 229910052717 sulfur Inorganic materials 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 230000002538 fungal effect Effects 0.000 description 18
- 125000004434 sulfur atom Chemical group 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 17
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 17
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- 239000000725 suspension Substances 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 15
- 125000004663 dialkyl amino group Chemical group 0.000 description 15
- 125000004438 haloalkoxy group Chemical group 0.000 description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 15
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
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- 125000002619 bicyclic group Chemical group 0.000 description 14
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- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 14
- 125000000753 cycloalkyl group Chemical group 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 125000003282 alkyl amino group Chemical group 0.000 description 12
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
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- 239000004308 thiabendazole Substances 0.000 description 1
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- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 125000001391 thioamide group Chemical group 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- XQJQCBDIXRIYRP-STQMWFEESA-N trans-(1S,2R)-sedaxane Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1[C@H]1[C@H](C2CC2)C1 XQJQCBDIXRIYRP-STQMWFEESA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical group CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ZDRNMODJXFOYMN-UHFFFAOYSA-N tridecyl acetate Chemical compound CCCCCCCCCCCCCOC(C)=O ZDRNMODJXFOYMN-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000004072 triols Chemical group 0.000 description 1
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- 241000701447 unidentified baculovirus Species 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 1
- 229940045145 uridine Drugs 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical group N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 238000006175 van Leusen reaction Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 230000009105 vegetative growth Effects 0.000 description 1
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- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- PQHXFGUTAAIHOC-XZZSYSLUSA-N α-(methoxyimino)-n-methyl-2-[[[1-[3-(trifluoromethyl)phenyl]ethoxy]imino]methyl]benzeneacetamide Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1\C=N\OC(C)C1=CC=CC(C(F)(F)F)=C1 PQHXFGUTAAIHOC-XZZSYSLUSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A01N43/80—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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- 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
- 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)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29309510P | 2010-01-07 | 2010-01-07 | |
| US61/293,095 | 2010-01-07 | ||
| PCT/US2011/020473 WO2011085170A1 (en) | 2010-01-07 | 2011-01-07 | Fungicidal heterocyclic compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013516483A JP2013516483A (ja) | 2013-05-13 |
| JP2013516483A5 JP2013516483A5 (OSRAM) | 2014-02-20 |
| JP5715646B2 true JP5715646B2 (ja) | 2015-05-13 |
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| JP2012548142A Expired - Fee Related JP5715646B2 (ja) | 2010-01-07 | 2011-01-07 | 殺菌・殺カビ性ヘテロ環式化合物 |
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| EP (1) | EP2521450B1 (OSRAM) |
| JP (1) | JP5715646B2 (OSRAM) |
| KR (1) | KR20120112755A (OSRAM) |
| CN (1) | CN102791133B (OSRAM) |
| AU (1) | AU2011204323B2 (OSRAM) |
| BR (1) | BR112012016733A2 (OSRAM) |
| CL (1) | CL2012001805A1 (OSRAM) |
| ES (1) | ES2534516T3 (OSRAM) |
| IN (1) | IN2012DN05233A (OSRAM) |
| MX (1) | MX2012007935A (OSRAM) |
| PL (1) | PL2521450T3 (OSRAM) |
| WO (1) | WO2011085170A1 (OSRAM) |
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| US10004232B2 (en) | 2011-09-15 | 2018-06-26 | Bayer Intellectual Property Gmbh | Piperidine pyrazoles as fungicides |
| PE20190342A1 (es) | 2012-02-27 | 2019-03-07 | Bayer Ip Gmbh | Combinaciones de compuestos activos |
| PL2861566T3 (pl) | 2012-06-13 | 2017-06-30 | F.Hoffmann-La Roche Ag | Nowy diazaspirocykloalkan i azaspirocykloalkan |
| MX2014015511A (es) * | 2012-06-22 | 2015-03-19 | Du Pont | Compuestos fungicidas heterociclicos. |
| ES2588386T3 (es) | 2012-08-30 | 2016-11-02 | Bayer Cropscience Ag | Procedimiento de descarboxilación de derivados de ácido 3,5-bis(haloalquil)-pirazol-4-carboxílico |
| PL2900669T3 (pl) | 2012-09-25 | 2020-01-31 | F. Hoffmann-La Roche Ag | Pochodne heksahydropirolo[3,4-C]pirolu i związki pokrewne jako inhibitory autotaksyny (ATX) oraz inhibitory produkcji kwasu lizofosfatydowego (LPA) do leczenia np. chorób nerek |
| AR095079A1 (es) | 2013-03-12 | 2015-09-16 | Hoffmann La Roche | Derivados de octahidro-pirrolo[3,4-c]-pirrol y piridina-fenilo |
| US9540324B2 (en) | 2013-09-26 | 2017-01-10 | Luc Therapeutics, Inc. | Selective octahydro-cyclopenta[C] pyrrole negative modulators of NR2B |
| US9077321B2 (en) | 2013-10-23 | 2015-07-07 | Corning Optical Communications Wireless Ltd. | Variable amplitude signal generators for generating a sinusoidal signal having limited direct current (DC) offset variation, and related devices, systems, and methods |
| HUE036117T2 (hu) | 2013-11-26 | 2018-06-28 | Hoffmann La Roche | Oktahidro-ciklobuta[1,2-C;3,4-C']dipirrol származékok, mint autotaxin inhibitorok |
| CN106132202B (zh) | 2014-03-20 | 2021-12-31 | 三井化学Agro株式会社 | 植物病害防除组合物及应用该组合物以防除植物病害的方法 |
| EA037928B1 (ru) | 2014-03-26 | 2021-06-08 | Ф. Хоффманн-Ля Рош Аг | Бициклические соединения в качестве ингибиторов продукции аутотаксина (atx) и лизофосфатидиловой кислоты (lpa) |
| JP6554481B2 (ja) | 2014-03-26 | 2019-07-31 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | オートタキシン（ａｔｘ）及びリゾホスファチジン酸（ｌｐａ）産生の阻害剤としての縮合［１，４］ジアゼピン化合物 |
| TWI665192B (zh) * | 2014-05-28 | 2019-07-11 | 德商拜耳作物科學股份有限公司 | 製備二氫異唑衍生物之方法 |
| WO2016024350A1 (ja) | 2014-08-13 | 2016-02-18 | 株式会社エス・ディー・エス バイオテック | 縮合１１員環化合物及びそれらを含有する農園芸用殺菌剤 |
| JO3579B1 (ar) | 2014-09-26 | 2020-07-05 | Luc Therapeutics Inc | مُعدِلات تفاغرية سالبة لمستقبل nr2b من المركب n-ألكيل أريل-5-أوكسي أريل-ثامن هيدرو-خماسي الحلقة [c] بيرول |
| US10189799B2 (en) | 2015-03-05 | 2019-01-29 | Bayer Cropscience Aktiengesellschaft | Process for preparing substituted phenylisoxazoline derivatives |
| MA41898A (fr) | 2015-04-10 | 2018-02-13 | Hoffmann La Roche | Dérivés de quinazolinone bicyclique |
| WO2016202761A1 (en) | 2015-06-17 | 2016-12-22 | Bayer Cropscience Aktiengesellschaft | Active compound combinations |
| CR20180058A (es) | 2015-09-04 | 2018-02-26 | Hoffmann La Roche | Nuevos derivados de fenoximetilo |
| KR20180054830A (ko) | 2015-09-24 | 2018-05-24 | 에프. 호프만-라 로슈 아게 | 오토탁신(atx) 억제제로서의 이환형 화합물 |
| EP3353178B1 (en) | 2015-09-24 | 2021-07-14 | F. Hoffmann-La Roche AG | Bicyclic compounds as dual atx/ca inhibitors |
| CN107922412B (zh) | 2015-09-24 | 2021-02-23 | 豪夫迈·罗氏有限公司 | 作为atx抑制剂的二环化合物 |
| MX2017015034A (es) | 2015-09-24 | 2018-04-13 | Hoffmann La Roche | Nuevos compuestos biciclicos como inhibidores duales de autotaxina (atx)/anhidrasa carbonica (ca). |
| CN108602765B (zh) | 2016-02-08 | 2022-05-03 | 高文有限公司 | 1,2-苯二甲醇化合物的制造方法 |
| CN108601353B (zh) | 2016-02-08 | 2024-04-05 | 高文作物保护公司 | 杀菌性组合物 |
| EP3596060B1 (en) | 2017-03-16 | 2023-09-20 | F. Hoffmann-La Roche AG | New bicyclic compounds as atx inhibitors |
| RU2019132254A (ru) | 2017-03-16 | 2021-04-16 | Ф. Хоффманн-Ля Рош Аг | Гетероциклические соединения, пригодные в качестве дуальных ингибиторов atx/ca |
| TW201838974A (zh) | 2017-04-19 | 2018-11-01 | 印度商Ｐｉ工業公司 | 具殺菌性質之雜環化合物 |
| WO2019048989A1 (en) | 2017-09-08 | 2019-03-14 | Pi Industries Ltd. | NOVEL FUNGICIDE HETEROCYCLIC COMPOUNDS |
| WO2019048988A1 (en) | 2017-09-08 | 2019-03-14 | Pi Industries Ltd. | Novel fungidal heterocyclic compounds |
| CN109516962A (zh) * | 2018-12-13 | 2019-03-26 | 天津雅奥泰克科技有限公司 | 一种合成2,6-二氟苯基-1-(4,5-二氢异恶唑)-3-乙基酮的新方法 |
| CN115594670B (zh) * | 2021-06-28 | 2025-07-04 | 浙江省化工研究院有限公司 | 一类含三氟甲基噁二唑类衍生物、其制备方法及应用 |
| EP4509511A1 (en) | 2023-08-17 | 2025-02-19 | Bayer Aktiengesellschaft | Substituted spiro-isoxazolinyl lactams, salts thereof and their use as herbicidally active substances |
| CN118878474B (zh) * | 2024-07-01 | 2025-10-28 | 盐城工学院 | 一种合成2,6-二氟苯基-1-(4,5-二氢异恶唑)-3-乙基酮的方法 |
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- 2011-01-07 BR BRBR112012016733-2A patent/BR112012016733A2/pt not_active Application Discontinuation
- 2011-01-07 KR KR1020127020596A patent/KR20120112755A/ko not_active Withdrawn
- 2011-01-07 EP EP11701172.6A patent/EP2521450B1/en not_active Not-in-force
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2521450A1 (en) | 2012-11-14 |
| WO2011085170A1 (en) | 2011-07-14 |
| BR112012016733A2 (pt) | 2015-09-01 |
| IN2012DN05233A (OSRAM) | 2015-10-23 |
| PL2521450T3 (pl) | 2015-07-31 |
| CN102791133B (zh) | 2015-09-23 |
| AU2011204323A1 (en) | 2012-06-28 |
| JP2013516483A (ja) | 2013-05-13 |
| CL2012001805A1 (es) | 2013-02-22 |
| US8835427B2 (en) | 2014-09-16 |
| EP2521450B1 (en) | 2015-02-25 |
| CN102791133A (zh) | 2012-11-21 |
| KR20120112755A (ko) | 2012-10-11 |
| AU2011204323B2 (en) | 2013-12-12 |
| MX2012007935A (es) | 2012-08-15 |
| US20120309752A1 (en) | 2012-12-06 |
| ES2534516T3 (es) | 2015-04-23 |
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