JP5529044B2 - 殺菌性複素環化合物 - Google Patents
殺菌性複素環化合物 Download PDFInfo
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- JP5529044B2 JP5529044B2 JP2010544413A JP2010544413A JP5529044B2 JP 5529044 B2 JP5529044 B2 JP 5529044B2 JP 2010544413 A JP2010544413 A JP 2010544413A JP 2010544413 A JP2010544413 A JP 2010544413A JP 5529044 B2 JP5529044 B2 JP 5529044B2
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- 230000000844 anti-bacterial effect Effects 0.000 title claims description 50
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 659
- -1 cyano, hydroxy Chemical group 0.000 claims description 270
- 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 106
- 229910052799 carbon Inorganic materials 0.000 claims description 94
- 229910052736 halogen Inorganic materials 0.000 claims description 93
- 150000002367 halogens Chemical class 0.000 claims description 93
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 92
- 238000000034 method Methods 0.000 claims description 75
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 64
- 150000003839 salts Chemical class 0.000 claims description 46
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 43
- 150000001721 carbon Chemical group 0.000 claims description 42
- 229910052760 oxygen Inorganic materials 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 150000001204 N-oxides Chemical class 0.000 claims description 31
- 229910052717 sulfur Inorganic materials 0.000 claims description 30
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 29
- 201000010099 disease Diseases 0.000 claims description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 24
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 21
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 244000000004 fungal plant pathogen Species 0.000 claims description 6
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
- MHHBHSAYGWOQIM-UHFFFAOYSA-N n'-(2,5-dimethylphenyl)-4-[4-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidine-1-carboximidamide Chemical compound CC1=CC=C(C)C(NC(=N)N2CCC(CC2)C=2SC=C(N=2)C=2CC(ON=2)C=2C=CC=CC=2)=C1 MHHBHSAYGWOQIM-UHFFFAOYSA-N 0.000 claims description 4
- 241000233654 Oomycetes Species 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 1
- 230000011987 methylation Effects 0.000 claims 1
- 238000007069 methylation reaction Methods 0.000 claims 1
- 239000000417 fungicide Substances 0.000 description 286
- 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 description 262
- 230000000855 fungicidal effect Effects 0.000 description 128
- 125000001424 substituent group Chemical group 0.000 description 123
- 239000000203 mixture Substances 0.000 description 114
- 125000000217 alkyl group Chemical group 0.000 description 101
- 125000003545 alkoxy group Chemical group 0.000 description 68
- 230000009471 action Effects 0.000 description 65
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 59
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 48
- 238000002360 preparation method Methods 0.000 description 48
- 150000001412 amines Chemical class 0.000 description 47
- 238000006243 chemical reaction Methods 0.000 description 44
- 241000196324 Embryophyta Species 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 42
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 41
- 239000003899 bactericide agent Substances 0.000 description 40
- 125000001188 haloalkyl group Chemical group 0.000 description 40
- 125000000623 heterocyclic group Chemical group 0.000 description 40
- 239000007787 solid Substances 0.000 description 39
- 125000004122 cyclic group Chemical group 0.000 description 38
- 125000004433 nitrogen atom Chemical group N* 0.000 description 37
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 239000002253 acid Substances 0.000 description 36
- 125000001624 naphthyl group Chemical group 0.000 description 34
- 239000000243 solution Substances 0.000 description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 33
- 239000011541 reaction mixture Substances 0.000 description 33
- 239000002904 solvent Substances 0.000 description 33
- 125000004663 dialkyl amino group Chemical group 0.000 description 31
- 229920006395 saturated elastomer Polymers 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 30
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 29
- 230000015572 biosynthetic process Effects 0.000 description 29
- 239000000460 chlorine Substances 0.000 description 29
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 29
- 125000004429 atom Chemical group 0.000 description 28
- 238000009472 formulation Methods 0.000 description 27
- 239000000047 product Substances 0.000 description 27
- 230000002829 reductive effect Effects 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000002585 base Substances 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- 125000004438 haloalkoxy group Chemical group 0.000 description 25
- 125000004414 alkyl thio group Chemical group 0.000 description 24
- 239000007788 liquid Substances 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 23
- 229910052801 chlorine Inorganic materials 0.000 description 23
- 241000233866 Fungi Species 0.000 description 22
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 21
- 230000002538 fungal effect Effects 0.000 description 21
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 20
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 20
- 125000003282 alkyl amino group Chemical group 0.000 description 20
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 description 20
- 229910052794 bromium Inorganic materials 0.000 description 20
- 239000003085 diluting agent Substances 0.000 description 20
- 230000012010 growth Effects 0.000 description 20
- 125000004665 trialkylsilyl group Chemical group 0.000 description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 19
- 239000003921 oil Substances 0.000 description 19
- 235000019198 oils Nutrition 0.000 description 19
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 18
- 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
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 18
- 125000005842 heteroatom Chemical group 0.000 description 18
- 239000004094 surface-active agent Substances 0.000 description 18
- 238000003786 synthesis reaction Methods 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
- 125000003118 aryl group Chemical group 0.000 description 17
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 17
- 125000005347 halocycloalkyl group Chemical group 0.000 description 17
- 235000011181 potassium carbonates Nutrition 0.000 description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 17
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 17
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 description 16
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000004480 active ingredient Substances 0.000 description 16
- 125000000753 cycloalkyl group Chemical group 0.000 description 16
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 16
- 150000003254 radicals Chemical class 0.000 description 16
- 238000006467 substitution reaction Methods 0.000 description 16
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 15
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 125000000000 cycloalkoxy group Chemical group 0.000 description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 15
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 14
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 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
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 14
- 125000002619 bicyclic group Chemical group 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- 229910052740 iodine Inorganic materials 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 13
- 239000002516 radical scavenger Substances 0.000 description 13
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 229930182558 Sterol Natural products 0.000 description 12
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 12
- 150000001408 amides Chemical class 0.000 description 12
- 238000010168 coupling process Methods 0.000 description 12
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 description 12
- 239000003112 inhibitor Substances 0.000 description 12
- 125000003386 piperidinyl group Chemical group 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- 150000003432 sterols Chemical class 0.000 description 12
- 235000003702 sterols Nutrition 0.000 description 12
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 11
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 11
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 description 11
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 11
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 11
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 11
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 description 11
- 125000000262 haloalkenyl group Chemical group 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 230000005764 inhibitory process Effects 0.000 description 11
- 125000002757 morpholinyl group Chemical group 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 description 10
- 125000006765 (C2-C6) haloalkenyloxy group Chemical group 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 10
- 230000008878 coupling Effects 0.000 description 10
- 238000005859 coupling reaction Methods 0.000 description 10
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 description 10
- 125000000232 haloalkynyl group Chemical group 0.000 description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 9
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 description 9
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical class O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 9
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 9
- 125000003320 C2-C6 alkenyloxy group Chemical group 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
- 238000007792 addition Methods 0.000 description 9
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 9
- 238000011161 development Methods 0.000 description 9
- 230000018109 developmental process Effects 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
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- 125000004994 halo alkoxy alkyl group Chemical group 0.000 description 9
- 125000000842 isoxazolyl group Chemical group 0.000 description 9
- 230000008099 melanin synthesis Effects 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- 230000001954 sterilising effect Effects 0.000 description 9
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 8
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- AIKKULXCBHRFOS-UHFFFAOYSA-N Formothion Chemical compound COP(=S)(OC)SCC(=O)N(C)C=O AIKKULXCBHRFOS-UHFFFAOYSA-N 0.000 description 8
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 8
- 150000001336 alkenes Chemical class 0.000 description 8
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 8
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 description 8
- 239000000645 desinfectant Substances 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 150000004820 halides Chemical class 0.000 description 8
- 150000002545 isoxazoles Chemical group 0.000 description 8
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 8
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 7
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 125000004702 alkoxy alkyl carbonyl group Chemical group 0.000 description 7
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- 239000003153 chemical reaction reagent Substances 0.000 description 7
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- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 7
- 125000004461 halocycloalkylalkyl group Chemical group 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 150000002825 nitriles Chemical class 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 230000029058 respiratory gaseous exchange Effects 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- 235000017550 sodium carbonate Nutrition 0.000 description 7
- 125000004434 sulfur atom Chemical group 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 6
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 6
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 6
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 102000029749 Microtubule Human genes 0.000 description 6
- 108091022875 Microtubule Proteins 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 150000004716 alpha keto acids Chemical class 0.000 description 6
- 238000013459 approach Methods 0.000 description 6
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical group OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 6
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 6
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 238000007429 general method Methods 0.000 description 6
- 125000004995 haloalkylthio group Chemical group 0.000 description 6
- 150000004679 hydroxides Chemical class 0.000 description 6
- 125000002883 imidazolyl group Chemical group 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 210000004688 microtubule Anatomy 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- 150000003904 phospholipids Chemical class 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- YLZGKZDEFJIHIJ-UHFFFAOYSA-N (1-methylbenzimidazol-2-yl) carbamate Chemical compound C1=CC=C2N(C)C(OC(N)=O)=NC2=C1 YLZGKZDEFJIHIJ-UHFFFAOYSA-N 0.000 description 5
- 125000006798 (C1-C6) haloalkylamino group Chemical group 0.000 description 5
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- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical group CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
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- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical group OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
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- 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
- 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
- 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
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- 241000701447 unidentified baculovirus Species 0.000 description 1
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- 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
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- 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
- 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
-
- 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
- C07D417/02—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6239508P | 2008-01-25 | 2008-01-25 | |
| US61/062,395 | 2008-01-25 | ||
| PCT/US2009/031686 WO2009094445A2 (en) | 2008-01-25 | 2009-01-22 | Fungicidal hetercyclic compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011510928A JP2011510928A (ja) | 2011-04-07 |
| JP2011510928A5 JP2011510928A5 (enExample) | 2012-02-23 |
| JP5529044B2 true JP5529044B2 (ja) | 2014-06-25 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010544413A Expired - Fee Related JP5529044B2 (ja) | 2008-01-25 | 2009-01-22 | 殺菌性複素環化合物 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8349870B2 (enExample) |
| EP (2) | EP2402332A3 (enExample) |
| JP (1) | JP5529044B2 (enExample) |
| KR (2) | KR20100119552A (enExample) |
| CN (2) | CN101970432B (enExample) |
| AU (1) | AU2009206468B2 (enExample) |
| BR (1) | BRPI0905759A2 (enExample) |
| MX (1) | MX2010008102A (enExample) |
| WO (1) | WO2009094445A2 (enExample) |
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| CN101925598B (zh) | 2008-01-25 | 2014-03-05 | 杜邦公司 | 杀真菌酰胺 |
-
2009
- 2009-01-22 WO PCT/US2009/031686 patent/WO2009094445A2/en not_active Ceased
- 2009-01-22 KR KR1020107018519A patent/KR20100119552A/ko not_active Ceased
- 2009-01-22 BR BRPI0905759-5A patent/BRPI0905759A2/pt not_active Application Discontinuation
- 2009-01-22 MX MX2010008102A patent/MX2010008102A/es active IP Right Grant
- 2009-01-22 AU AU2009206468A patent/AU2009206468B2/en not_active Ceased
- 2009-01-22 JP JP2010544413A patent/JP5529044B2/ja not_active Expired - Fee Related
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- 2009-01-22 CN CN201410221847.2A patent/CN103965187A/zh active Pending
- 2009-01-22 EP EP11007851.6A patent/EP2402332A3/en not_active Withdrawn
- 2009-01-22 KR KR1020157014513A patent/KR20150065958A/ko not_active Ceased
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Also Published As
| Publication number | Publication date |
|---|---|
| CN103965187A (zh) | 2014-08-06 |
| WO2009094445A2 (en) | 2009-07-30 |
| BRPI0905759A2 (pt) | 2015-07-14 |
| MX2010008102A (es) | 2010-08-04 |
| EP2402332A3 (en) | 2014-10-29 |
| KR20150065958A (ko) | 2015-06-15 |
| US8349870B2 (en) | 2013-01-08 |
| JP2011510928A (ja) | 2011-04-07 |
| WO2009094445A3 (en) | 2010-08-26 |
| US20100292275A1 (en) | 2010-11-18 |
| CN101970432B (zh) | 2014-05-28 |
| AU2009206468A1 (en) | 2009-07-30 |
| EP2260032A2 (en) | 2010-12-15 |
| AU2009206468B2 (en) | 2014-01-09 |
| EP2402332A2 (en) | 2012-01-04 |
| CN101970432A (zh) | 2011-02-09 |
| KR20100119552A (ko) | 2010-11-09 |
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