KR20100119552A - 살균제 복소환 화합물 - Google Patents
살균제 복소환 화합물 Download PDFInfo
- Publication number
- KR20100119552A KR20100119552A KR1020107018519A KR20107018519A KR20100119552A KR 20100119552 A KR20100119552 A KR 20100119552A KR 1020107018519 A KR1020107018519 A KR 1020107018519A KR 20107018519 A KR20107018519 A KR 20107018519A KR 20100119552 A KR20100119552 A KR 20100119552A
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- KR
- South Korea
- Prior art keywords
- alkyl
- independently
- haloalkyl
- compound
- formula
- 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.)
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 618
- 230000000855 fungicidal effect Effects 0.000 title claims description 96
- 238000000034 method Methods 0.000 claims abstract description 89
- 150000003839 salts Chemical class 0.000 claims abstract description 46
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 33
- 201000010099 disease Diseases 0.000 claims abstract description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 25
- -1 cyano, hydroxy Chemical group 0.000 claims description 282
- 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 277
- 239000000417 fungicide Substances 0.000 claims description 194
- 125000001424 substituent group Chemical group 0.000 claims description 137
- 229910052799 carbon Inorganic materials 0.000 claims description 123
- 125000000217 alkyl group Chemical group 0.000 claims description 112
- 229910052736 halogen Inorganic materials 0.000 claims description 112
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 110
- 150000002367 halogens Chemical class 0.000 claims description 109
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 83
- 125000003545 alkoxy group Chemical group 0.000 claims description 78
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 72
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 68
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 61
- 125000001072 heteroaryl group Chemical group 0.000 claims description 60
- 150000001721 carbon Chemical group 0.000 claims description 50
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 48
- 125000000623 heterocyclic group Chemical group 0.000 claims description 47
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 45
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 44
- 125000001188 haloalkyl group Chemical group 0.000 claims description 44
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 125000001624 naphthyl group Chemical group 0.000 claims description 40
- 229910052760 oxygen Inorganic materials 0.000 claims description 40
- 239000007787 solid Substances 0.000 claims description 39
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 38
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 37
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 33
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 32
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 32
- 125000004414 alkyl thio group Chemical group 0.000 claims description 31
- 229920006395 saturated elastomer Polymers 0.000 claims description 31
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 30
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- 125000003282 alkyl amino group Chemical group 0.000 claims description 29
- 229910052717 sulfur Inorganic materials 0.000 claims description 29
- 125000004429 atom Chemical group 0.000 claims description 28
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 27
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 26
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 claims description 26
- 229910052801 chlorine Inorganic materials 0.000 claims description 25
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 24
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 24
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 23
- 125000005842 heteroatom Chemical group 0.000 claims description 23
- 239000007788 liquid Substances 0.000 claims description 23
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 22
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 22
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 21
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 19
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 19
- 239000003085 diluting agent Substances 0.000 claims description 19
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 19
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 18
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 18
- 125000002619 bicyclic group Chemical group 0.000 claims description 18
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 18
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 17
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 17
- 239000004094 surface-active agent Substances 0.000 claims description 17
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 16
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 16
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 16
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 16
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
- 230000000844 anti-bacterial effect Effects 0.000 claims description 15
- 125000003386 piperidinyl group Chemical group 0.000 claims description 15
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 15
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 14
- 125000006765 (C2-C6) haloalkenyloxy group Chemical group 0.000 claims description 14
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 14
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 14
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 14
- 125000002757 morpholinyl group Chemical group 0.000 claims description 14
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 13
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 13
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 12
- AIKKULXCBHRFOS-UHFFFAOYSA-N Formothion Chemical compound COP(=S)(OC)SCC(=O)N(C)C=O AIKKULXCBHRFOS-UHFFFAOYSA-N 0.000 claims description 12
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 12
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 12
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 11
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 11
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims description 11
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 11
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 11
- 125000004461 halocycloalkylalkyl group Chemical group 0.000 claims description 11
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 10
- 125000002837 carbocyclic group Chemical group 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000005203 haloalkylcarbonyloxy group Chemical group 0.000 claims description 10
- 125000006769 halocycloalkoxy group Chemical group 0.000 claims description 10
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 10
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 9
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 9
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 9
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 8
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 8
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 8
- 125000004702 alkoxy alkyl carbonyl group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000006798 (C1-C6) haloalkylamino group Chemical group 0.000 claims description 7
- 125000006767 (C2-C6) haloalkynyloxy group Chemical group 0.000 claims description 7
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
- 244000000004 fungal plant pathogen Species 0.000 claims description 7
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 7
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 6
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 6
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 5
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 5
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 5
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 5
- 125000004992 haloalkylamino group Chemical group 0.000 claims description 5
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 5
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 4
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
- 125000006815 (C4-C10) cycloalkylaminocarbonyl group Chemical group 0.000 claims description 4
- 125000006781 (C4-C10) cycloalkylcarbonyl group Chemical group 0.000 claims description 4
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000005082 alkoxyalkenyl group Chemical group 0.000 claims description 4
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims description 4
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 4
- 125000005130 alkyl carbonyl thio group Chemical group 0.000 claims description 4
- 125000005243 carbonyl alkyl group Chemical group 0.000 claims description 4
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 4
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 4
- 125000006825 (C2-C5) haloalkyl group Chemical group 0.000 claims description 3
- 125000005102 carbonylalkoxy group Chemical group 0.000 claims description 3
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 3
- 125000004664 haloalkylsulfonylamino group Chemical group 0.000 claims description 3
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 3
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 2
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 2
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 2
- 125000004983 dialkoxyalkyl group Chemical group 0.000 claims description 2
- 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims description 2
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004443 haloalkoxycarbonylamino group Chemical group 0.000 claims description 2
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 2
- FWAKQFRJEBLKAJ-UHFFFAOYSA-N methyl 4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]-n-(2,5-dimethylphenyl)piperidine-1-carboximidate Chemical compound C1CC(C=2SC=C(N=2)C=2CC(ON=2)C=2C(=CC=CC=2F)F)CCN1C(OC)=NC1=CC(C)=CC=C1C FWAKQFRJEBLKAJ-UHFFFAOYSA-N 0.000 claims description 2
- MDLFARDSAJZUFT-UHFFFAOYSA-N methyl 4-[4-[5-(2-cyanophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]-n-(2,5-dimethylphenyl)piperidine-1-carboximidate Chemical compound C1CC(C=2SC=C(N=2)C=2CC(ON=2)C=2C(=CC=CC=2)C#N)CCN1C(OC)=NC1=CC(C)=CC=C1C MDLFARDSAJZUFT-UHFFFAOYSA-N 0.000 claims description 2
- WRQMRBCEVAMVGQ-UHFFFAOYSA-N methyl n-(2,5-dimethylphenyl)-4-(4-spiro[1,2-dihydroindene-3,5'-4h-1,2-oxazole]-3'-yl-1,3-thiazol-2-yl)piperidine-1-carboximidate Chemical compound C1CC(C=2SC=C(N=2)C=2CC3(C4=CC=CC=C4CC3)ON=2)CCN1C(OC)=NC1=CC(C)=CC=C1C WRQMRBCEVAMVGQ-UHFFFAOYSA-N 0.000 claims description 2
- QXYHGGCEZDOTRE-UHFFFAOYSA-N methyl n-(2,5-dimethylphenyl)-4-[4-[5-(2-fluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidine-1-carboximidate Chemical compound C1CC(C=2SC=C(N=2)C=2CC(ON=2)C=2C(=CC=CC=2)F)CCN1C(OC)=NC1=CC(C)=CC=C1C QXYHGGCEZDOTRE-UHFFFAOYSA-N 0.000 claims description 2
- AGYVSBQQNSDGIS-UHFFFAOYSA-N methyl n-(2,5-dimethylphenyl)-4-[4-[5-(2-oxo-1,3-benzoxazol-3-yl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidine-1-carboximidate Chemical compound C1CC(C=2SC=C(N=2)C=2CC(ON=2)N2C(OC3=CC=CC=C32)=O)CCN1C(OC)=NC1=CC(C)=CC=C1C AGYVSBQQNSDGIS-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 107
- 244000053095 fungal pathogen Species 0.000 abstract 1
- 230000009471 action Effects 0.000 description 54
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 48
- 150000001412 amines Chemical class 0.000 description 47
- 238000006243 chemical reaction Methods 0.000 description 43
- 239000000243 solution Substances 0.000 description 43
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- 241000196324 Embryophyta Species 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 239000002253 acid Substances 0.000 description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 238000009472 formulation Methods 0.000 description 32
- 239000011541 reaction mixture Substances 0.000 description 32
- 238000002360 preparation method Methods 0.000 description 31
- 239000002904 solvent Substances 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 30
- 239000000460 chlorine Substances 0.000 description 29
- 230000002829 reductive effect Effects 0.000 description 29
- 239000002585 base Substances 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000003921 oil Substances 0.000 description 22
- 235000019198 oils Nutrition 0.000 description 22
- 241000233866 Fungi Species 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 21
- 125000004122 cyclic group Chemical group 0.000 description 21
- 230000012010 growth Effects 0.000 description 20
- 229910052794 bromium Inorganic materials 0.000 description 19
- 239000003054 catalyst Substances 0.000 description 19
- 230000002538 fungal effect Effects 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 235000011181 potassium carbonates Nutrition 0.000 description 18
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 239000003112 inhibitor Substances 0.000 description 14
- 229910052740 iodine Inorganic materials 0.000 description 14
- 150000003254 radicals Chemical class 0.000 description 14
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 13
- 230000008878 coupling Effects 0.000 description 13
- 238000010168 coupling process Methods 0.000 description 13
- 238000005859 coupling reaction Methods 0.000 description 13
- 230000008569 process Effects 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 150000002545 isoxazoles Chemical group 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
- 239000002516 radical scavenger Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 150000001408 amides Chemical class 0.000 description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 150000003871 sulfonates Chemical class 0.000 description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 10
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
- 101150065749 Churc1 gene Proteins 0.000 description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 9
- 102100038239 Protein Churchill Human genes 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 230000005764 inhibitory process Effects 0.000 description 9
- 230000008099 melanin synthesis Effects 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 102000004190 Enzymes Human genes 0.000 description 8
- 108090000790 Enzymes Proteins 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
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- CRFYLQMIDWBKRT-LPYMAVHISA-N pyribencarb Chemical compound C1=C(Cl)C(CNC(=O)OC)=CC(C(\C)=N\OCC=2N=C(C)C=CC=2)=C1 CRFYLQMIDWBKRT-LPYMAVHISA-N 0.000 description 1
- QDGHXQFTWKRQTG-UHFFFAOYSA-N pyrimidin-2-ylhydrazine Chemical class NNC1=NC=CC=N1 QDGHXQFTWKRQTG-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- WRPIRSINYZBGPK-UHFFFAOYSA-N quinoxyfen Chemical compound C1=CC(F)=CC=C1OC1=CC=NC2=CC(Cl)=CC(Cl)=C12 WRPIRSINYZBGPK-UHFFFAOYSA-N 0.000 description 1
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- DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 description 1
- 229960002722 terbinafine Drugs 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- XLGKMJFDRZHAEV-UHFFFAOYSA-N tert-butyl 4-(4-formyl-1,3-thiazol-2-yl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=NC(C=O)=CS1 XLGKMJFDRZHAEV-UHFFFAOYSA-N 0.000 description 1
- CCKFYPVQHIBLPF-UHFFFAOYSA-N tert-butyl 4-[4-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=NC(C=2CC(ON=2)C=2C=CC=CC=2)=CS1 CCKFYPVQHIBLPF-UHFFFAOYSA-N 0.000 description 1
- SCGQNJHAAYUQOO-UHFFFAOYSA-N tert-butyl 4-carbamothioylpiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(C(N)=S)CC1 SCGQNJHAAYUQOO-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical group 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- 125000001391 thioamide group Chemical group 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
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-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
- 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
- 230000009466 transformation Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- 229960003567 tribenoside Drugs 0.000 description 1
- 230000004102 tricarboxylic acid cycle Effects 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound 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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-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
- 108010013280 ubiquinol oxidase Proteins 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 compound 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
- 230000002792 vascular Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- 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
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
-
- 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
- A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
-
- 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
- A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives thereof
-
- 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)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6239508P | 2008-01-25 | 2008-01-25 | |
| US61/062,395 | 2008-01-25 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| KR1020157014513A Division KR20150065958A (ko) | 2008-01-25 | 2009-01-22 | 살균제 복소환 화합물 |
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| Publication Number | Publication Date |
|---|---|
| KR20100119552A true KR20100119552A (ko) | 2010-11-09 |
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| KR1020107018519A Ceased KR20100119552A (ko) | 2008-01-25 | 2009-01-22 | 살균제 복소환 화합물 |
| KR1020157014513A Ceased KR20150065958A (ko) | 2008-01-25 | 2009-01-22 | 살균제 복소환 화합물 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
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| KR1020157014513A Ceased KR20150065958A (ko) | 2008-01-25 | 2009-01-22 | 살균제 복소환 화합물 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8349870B2 (enExample) |
| EP (2) | EP2260032A2 (enExample) |
| JP (1) | JP5529044B2 (enExample) |
| KR (2) | KR20100119552A (enExample) |
| CN (2) | CN103965187A (enExample) |
| AU (1) | AU2009206468B2 (enExample) |
| BR (1) | BRPI0905759A2 (enExample) |
| MX (1) | MX2010008102A (enExample) |
| WO (1) | WO2009094445A2 (enExample) |
Families Citing this family (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9090604B2 (en) | 2006-07-27 | 2015-07-28 | E I Du Pont De Nemours And Company | Fungicidal azocyclic amides |
| WO2008013622A2 (en) | 2006-07-27 | 2008-01-31 | E. I. Du Pont De Nemours And Company | Fungicidal azocyclic amides |
| US9643922B2 (en) | 2008-08-18 | 2017-05-09 | Yale University | MIF modulators |
| EP2326631A4 (en) * | 2008-08-18 | 2012-03-21 | Univ Yale | MIF MODULATORS |
| US9540322B2 (en) | 2008-08-18 | 2017-01-10 | Yale University | MIF modulators |
| ES2452299T3 (es) | 2008-12-02 | 2014-03-31 | E. I. Du Pont De Nemours And Company | Compuestos heterocíclicos fungicidas |
| CN102292334A (zh) | 2008-12-11 | 2011-12-21 | 拜尔农作物科学股份公司 | 噻唑基肟醚和腙植物保护剂 |
| US20100267706A1 (en) * | 2009-04-20 | 2010-10-21 | Institute For Oneworld Health | Compounds, Compositions and Methods Comprising Pyridazine Derivatives |
| AR076687A1 (es) * | 2009-05-18 | 2011-06-29 | Infinity Pharmaceuticals Inc | Isoxazolinas como inhibidores de la amidahidrolasa de acidos grasos y com-posiciones farmaceuticas que los contienen |
| US9149465B2 (en) | 2009-05-18 | 2015-10-06 | Infinity Pharmaceuticals, Inc. | Isoxazolines as inhibitors of fatty acid amide hydrolase |
| US8927551B2 (en) | 2009-05-18 | 2015-01-06 | Infinity Pharmaceuticals, Inc. | Isoxazolines as inhibitors of fatty acid amide hydrolase |
| US8557821B2 (en) * | 2009-08-12 | 2013-10-15 | Syngenta Crop Protection, Llc | Microbiocidal heterocycles |
| KR20120101019A (ko) | 2009-10-30 | 2012-09-12 | 바이엘 크롭사이언스 아게 | 헤테로아릴피페리딘 및 -피페라진 유도체 |
| BR112012013801A2 (pt) * | 2009-12-11 | 2019-09-24 | Du Pont | composto,método para inibir a atividade de hidrolase de amida de ácido graxo em um indivíduo,composição farmacêutica e método para tratar um individuo com dor |
| WO2011076699A1 (de) | 2009-12-21 | 2011-06-30 | Bayer Cropscience Ag | Bis(difluormethyl)pyrazole als fungizide |
| CN102791133B (zh) | 2010-01-07 | 2015-09-23 | 纳幕尔杜邦公司 | 杀真菌杂环化合物 |
| KR20130100903A (ko) | 2010-04-28 | 2013-09-12 | 바이엘 크롭사이언스 아게 | 살진균제로서의 케토헤테로아릴피페리딘 및 케토헤테로아릴피페라진 유도체 |
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2009
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- 2009-01-22 KR KR1020107018519A patent/KR20100119552A/ko not_active Ceased
- 2009-01-22 CN CN201410221847.2A patent/CN103965187A/zh active Pending
- 2009-01-22 AU AU2009206468A patent/AU2009206468B2/en not_active Ceased
- 2009-01-22 BR BRPI0905759-5A patent/BRPI0905759A2/pt not_active Application Discontinuation
- 2009-01-22 KR KR1020157014513A patent/KR20150065958A/ko not_active Ceased
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| US20100292275A1 (en) | 2010-11-18 |
| MX2010008102A (es) | 2010-08-04 |
| AU2009206468A1 (en) | 2009-07-30 |
| CN103965187A (zh) | 2014-08-06 |
| WO2009094445A2 (en) | 2009-07-30 |
| KR20150065958A (ko) | 2015-06-15 |
| EP2402332A3 (en) | 2014-10-29 |
| JP5529044B2 (ja) | 2014-06-25 |
| EP2402332A2 (en) | 2012-01-04 |
| CN101970432B (zh) | 2014-05-28 |
| WO2009094445A3 (en) | 2010-08-26 |
| EP2260032A2 (en) | 2010-12-15 |
| AU2009206468B2 (en) | 2014-01-09 |
| BRPI0905759A2 (pt) | 2015-07-14 |
| US8349870B2 (en) | 2013-01-08 |
| JP2011510928A (ja) | 2011-04-07 |
| CN101970432A (zh) | 2011-02-09 |
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