KR20140008471A - 살진균 활성을 갖는 티에노-피리미딘 화합물 - Google Patents
살진균 활성을 갖는 티에노-피리미딘 화합물 Download PDFInfo
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- KR20140008471A KR20140008471A KR1020137034724A KR20137034724A KR20140008471A KR 20140008471 A KR20140008471 A KR 20140008471A KR 1020137034724 A KR1020137034724 A KR 1020137034724A KR 20137034724 A KR20137034724 A KR 20137034724A KR 20140008471 A KR20140008471 A KR 20140008471A
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- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 13
- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical class C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 179
- 239000000203 mixture Substances 0.000 claims description 98
- -1 methoxy, ethoxy, benzyloxy, phenoxy Chemical group 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 239000002689 soil Substances 0.000 claims description 15
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 230000002538 fungal effect Effects 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 230000002401 inhibitory effect Effects 0.000 claims description 9
- 125000002619 bicyclic group Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 125000000335 thiazolyl group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 3
- 230000005764 inhibitory process Effects 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- BOIUBJYPHIFHEJ-UHFFFAOYSA-N 2,4-difluoro-1,3-benzodioxole Chemical compound C1=CC(F)=C2OC(F)OC2=C1 BOIUBJYPHIFHEJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 125000004970 halomethyl group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000005647 linker group Chemical group 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- DDWBRNXDKNIQDY-UHFFFAOYSA-N thieno[2,3-d]pyrimidine Chemical class N1=CN=C2SC=CC2=C1 DDWBRNXDKNIQDY-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 87
- 241000196324 Embryophyta Species 0.000 description 81
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 69
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- 239000011734 sodium Substances 0.000 description 43
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 41
- 239000007787 solid Substances 0.000 description 40
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 39
- 239000002904 solvent Substances 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 150000001412 amines Chemical class 0.000 description 33
- 239000012267 brine Substances 0.000 description 33
- 239000000047 product Substances 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 30
- 201000010099 disease Diseases 0.000 description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
- 235000019439 ethyl acetate Nutrition 0.000 description 23
- 238000009472 formulation Methods 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 20
- 239000003921 oil Substances 0.000 description 20
- 235000019198 oils Nutrition 0.000 description 20
- 239000000741 silica gel Substances 0.000 description 19
- 229910002027 silica gel Inorganic materials 0.000 description 19
- 238000012360 testing method Methods 0.000 description 19
- 239000000725 suspension Substances 0.000 description 17
- 239000000417 fungicide Substances 0.000 description 16
- 241000209140 Triticum Species 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 14
- 241000233866 Fungi Species 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 125000003342 alkenyl group Chemical group 0.000 description 13
- 125000000304 alkynyl group Chemical group 0.000 description 13
- 238000001816 cooling Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- 229940086542 triethylamine Drugs 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 235000021307 Triticum Nutrition 0.000 description 10
- 238000003818 flash chromatography Methods 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000004587 chromatography analysis Methods 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 239000012230 colorless oil Substances 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000003415 peat Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- 240000008067 Cucumis sativus Species 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000004495 emulsifiable concentrate Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 230000000749 insecticidal effect Effects 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000009331 sowing Methods 0.000 description 6
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 5
- 241000221785 Erysiphales Species 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- IKCKRHCJPVDELP-UHFFFAOYSA-N 5-bromo-4-chlorothieno[2,3-d]pyrimidine Chemical compound ClC1=NC=NC2=C1C(Br)=CS2 IKCKRHCJPVDELP-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000004438 haloalkoxy group Chemical group 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- IWTFOFMTUOBLHG-UHFFFAOYSA-N 2-methoxypyridine Chemical compound COC1=CC=CC=N1 IWTFOFMTUOBLHG-UHFFFAOYSA-N 0.000 description 3
- INQKRFIZSFXMLG-UHFFFAOYSA-N 4-chloro-5-methylsulfanylthieno[2,3-d]pyrimidine Chemical compound C1=NC(Cl)=C2C(SC)=CSC2=N1 INQKRFIZSFXMLG-UHFFFAOYSA-N 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 208000031888 Mycoses Diseases 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 240000003768 Solanum lycopersicum Species 0.000 description 3
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
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- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 3
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- 239000006185 dispersion Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 150000002466 imines Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000003032 phytopathogenic effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 125000000168 pyrrolyl group Chemical group 0.000 description 3
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 3
- 238000004007 reversed phase HPLC Methods 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- 239000003039 volatile agent Substances 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- AYKYOOPFBCOXSL-UHFFFAOYSA-N (4-hydroxyphenyl)acetonitrile Chemical compound OC1=CC=C(CC#N)C=C1 AYKYOOPFBCOXSL-UHFFFAOYSA-N 0.000 description 2
- JDNPUJCKXLOHOW-UHFFFAOYSA-N 1-(bromomethyl)-4-(trifluoromethoxy)benzene Chemical compound FC(F)(F)OC1=CC=C(CBr)C=C1 JDNPUJCKXLOHOW-UHFFFAOYSA-N 0.000 description 2
- 229940044613 1-propanol Drugs 0.000 description 2
- ATRQECRSCHYSNP-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CC=N1 ATRQECRSCHYSNP-UHFFFAOYSA-N 0.000 description 2
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- BQJPYFZVTRGPOT-UHFFFAOYSA-N 4-chloro-5-ethoxythieno[2,3-d]pyrimidine Chemical compound C1=NC(Cl)=C2C(OCC)=CSC2=N1 BQJPYFZVTRGPOT-UHFFFAOYSA-N 0.000 description 2
- ONDSYCIJLUONNJ-UHFFFAOYSA-N 4-chloro-5-fluorothieno[2,3-d]pyrimidine Chemical compound C1=NC(Cl)=C2C(F)=CSC2=N1 ONDSYCIJLUONNJ-UHFFFAOYSA-N 0.000 description 2
- KMQCGVZKCHEYNQ-UHFFFAOYSA-N 4-chloro-5-iodothieno[2,3-d]pyrimidine Chemical compound ClC1=NC=NC2=C1C(I)=CS2 KMQCGVZKCHEYNQ-UHFFFAOYSA-N 0.000 description 2
- IEXAORIOILUYOZ-UHFFFAOYSA-N 4-chloro-5-methylsulfonylthieno[2,3-d]pyrimidine Chemical compound C1=NC(Cl)=C2C(S(=O)(=O)C)=CSC2=N1 IEXAORIOILUYOZ-UHFFFAOYSA-N 0.000 description 2
- NZCRUBBNZGVREM-UHFFFAOYSA-N 4-chlorothieno[2,3-d]pyrimidine Chemical compound ClC1=NC=NC2=C1C=CS2 NZCRUBBNZGVREM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 241000228437 Cochliobolus Species 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IMQLKJBTEOYOSI-UHFFFAOYSA-N Diphosphoinositol tetrakisphosphate Chemical compound OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 description 2
- WCSVJXNKXSJDLQ-UHFFFAOYSA-N F[S+](C=CC1=NC=N2)C1=C2Cl Chemical compound F[S+](C=CC1=NC=N2)C1=C2Cl WCSVJXNKXSJDLQ-UHFFFAOYSA-N 0.000 description 2
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SAHQRQLWFUVHML-UHFFFAOYSA-N N1=CN=CC2=C1SC(=C2)C(=O)OCC Chemical compound N1=CN=CC2=C1SC(=C2)C(=O)OCC SAHQRQLWFUVHML-UHFFFAOYSA-N 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 241000736122 Parastagonospora nodorum Species 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 241000233622 Phytophthora infestans Species 0.000 description 2
- 241001246061 Puccinia triticina Species 0.000 description 2
- XYONNSVDNIRXKZ-UHFFFAOYSA-N S-methyl methanethiosulfonate Chemical compound CSS(C)(=O)=O XYONNSVDNIRXKZ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
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- DYGBNAYFDZEYBA-UHFFFAOYSA-N n-(cyclopropylmethyl)-2-[4-(4-methoxybenzoyl)piperidin-1-yl]-n-[(4-oxo-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-2-yl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(CC(=O)N(CC2CC2)CC=2NC(=O)C=3COCCC=3N=2)CC1 DYGBNAYFDZEYBA-UHFFFAOYSA-N 0.000 description 1
- IHCHOVVAJBADAH-UHFFFAOYSA-N n-[2-hydroxy-4-(1h-pyrazol-4-yl)phenyl]-6-methoxy-3,4-dihydro-2h-chromene-3-carboxamide Chemical compound C1C2=CC(OC)=CC=C2OCC1C(=O)NC(C(=C1)O)=CC=C1C=1C=NNC=1 IHCHOVVAJBADAH-UHFFFAOYSA-N 0.000 description 1
- YRCHYHRCBXNYNU-UHFFFAOYSA-N n-[[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]carbamothioyl]-2-(4-fluorophenyl)acetamide Chemical compound N1=CC(CNCCOC)=CC=C1C1=CC2=NC=CC(OC=3C(=CC(NC(=S)NC(=O)CC=4C=CC(F)=CC=4)=CC=3)F)=C2S1 YRCHYHRCBXNYNU-UHFFFAOYSA-N 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- UEICEJLUNGARHQ-UHFFFAOYSA-N pentane-1,4-diamine Chemical compound CC(N)CCCN UEICEJLUNGARHQ-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- LRYYUQJFQWSHNC-UHFFFAOYSA-N phenyl(4-phenylphosphanylbutyl)phosphane Chemical compound C=1C=CC=CC=1PCCCCPC1=CC=CC=C1 LRYYUQJFQWSHNC-UHFFFAOYSA-N 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920001521 polyalkylene glycol ether Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- GAPYKZAARZMMGP-UHFFFAOYSA-N pyridin-1-ium;acetate Chemical compound CC(O)=O.C1=CC=NC=C1 GAPYKZAARZMMGP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 1
- 229910000080 stannane Inorganic materials 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000004963 sulfonylalkyl group Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- ILNOTKMMDBWGOK-UHFFFAOYSA-N tert-butyl n-[2-(4-hydroxyphenyl)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCC1=CC=C(O)C=C1 ILNOTKMMDBWGOK-UHFFFAOYSA-N 0.000 description 1
- OBPIWKWNOASJDD-UHFFFAOYSA-N tert-butyl n-[2-[4-(2-oxopropoxy)phenyl]ethyl]carbamate Chemical compound CC(=O)COC1=CC=C(CCNC(=O)OC(C)(C)C)C=C1 OBPIWKWNOASJDD-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- DYTQGJLVGDSCLF-UHFFFAOYSA-N thieno[2,3-d]pyrimidin-4-amine Chemical compound NC1=NC=NC2=C1C=CS2 DYTQGJLVGDSCLF-UHFFFAOYSA-N 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical group CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylene diamine Substances C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- JQSHBVHOMNKWFT-DTORHVGOSA-N varenicline Chemical compound C12=CC3=NC=CN=C3C=C2[C@H]2C[C@@H]1CNC2 JQSHBVHOMNKWFT-DTORHVGOSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- 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
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62157704P | 2004-10-21 | 2004-10-21 | |
| US60/621,577 | 2004-10-21 | ||
| PCT/US2005/038145 WO2006047397A1 (en) | 2004-10-21 | 2005-10-21 | Thieno-pyrimidine compounds having fungicidal activity |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020077011335A Division KR101386797B1 (ko) | 2004-10-21 | 2005-10-21 | 살진균 활성을 갖는 티에노-피리미딘 화합물 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020147016709A Division KR20140094626A (ko) | 2004-10-21 | 2005-10-21 | 살진균 활성을 갖는 티에노-피리미딘 화합물 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20140008471A true KR20140008471A (ko) | 2014-01-21 |
Family
ID=35722379
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020137034724A Withdrawn KR20140008471A (ko) | 2004-10-21 | 2005-10-21 | 살진균 활성을 갖는 티에노-피리미딘 화합물 |
| KR1020147016709A Abandoned KR20140094626A (ko) | 2004-10-21 | 2005-10-21 | 살진균 활성을 갖는 티에노-피리미딘 화합물 |
| KR1020077011335A Expired - Fee Related KR101386797B1 (ko) | 2004-10-21 | 2005-10-21 | 살진균 활성을 갖는 티에노-피리미딘 화합물 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020147016709A Abandoned KR20140094626A (ko) | 2004-10-21 | 2005-10-21 | 살진균 활성을 갖는 티에노-피리미딘 화합물 |
| KR1020077011335A Expired - Fee Related KR101386797B1 (ko) | 2004-10-21 | 2005-10-21 | 살진균 활성을 갖는 티에노-피리미딘 화합물 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8008487B2 (https=) |
| EP (1) | EP1802632B1 (https=) |
| JP (2) | JP5122293B2 (https=) |
| KR (3) | KR20140008471A (https=) |
| CN (1) | CN101084224B (https=) |
| AT (1) | ATE516291T1 (https=) |
| BR (1) | BRPI0516242B1 (https=) |
| WO (1) | WO2006047397A1 (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8008487B2 (en) * | 2004-10-21 | 2011-08-30 | Dow Agrosciences Llc | Substituted thieno[2,3-D]pyrimidines as fungicides |
| EP1937691A1 (en) * | 2005-10-21 | 2008-07-02 | Dow Agrosciences LLC | Thieno-pyrimidine compounds having fungicidal activity |
| AP2008004687A0 (en) * | 2006-05-22 | 2008-12-31 | Basf Se | Insecticidal methods using 4-amino-5-chloro-thieno(2,3-d)-pyrimidine compounds |
| US8318384B2 (en) | 2007-04-30 | 2012-11-27 | The Governors Of The University Of Alberta | Anode catalyst and methods of making and using the same |
| CN102186479A (zh) * | 2008-09-10 | 2011-09-14 | 凯利普西斯公司 | 用于治疗疾病的组胺受体的氨基嘧啶抑制剂 |
| PL2455371T3 (pl) | 2009-07-16 | 2014-05-30 | Sds Biotech Corp | Pochodne 4-(3-butynylo)aminopirymidyny jako środki do zwalczania szkodników do stosowania w rolnictwie i ogrodnictwie |
| BR112012002164B1 (pt) | 2009-07-30 | 2021-04-20 | Merial, Inc | compostos inseticidas de 4-amino-tieno[2,3-d]-pirimidina e métodos para seu uso |
| AU2011354895B2 (en) | 2011-01-14 | 2016-05-05 | Sds Biotech K. K. | Agri-horticultural pest control compositions comprising 4- (3-butynyl)aminopyrimidine derivatives |
| ES2618813T3 (es) * | 2011-06-27 | 2017-06-22 | Merial, Inc. | Compuestos y composiciones de éter amido-piridílico y uso contra los parásitos |
| AR088218A1 (es) | 2011-07-19 | 2014-05-21 | Infinity Pharmaceuticals Inc | Compuestos heterociclicos utiles como inhibidores de pi3k |
| AR090037A1 (es) | 2011-11-15 | 2014-10-15 | Xention Ltd | Derivados de tieno y/o furo-pirimidinas y piridinas inhibidores de los canales de potasio |
| CN105315296B (zh) * | 2014-07-04 | 2018-04-03 | 沈阳中化农药化工研发有限公司 | 取代芳氧吡啶类化合物及其用途 |
| CN104725398B (zh) * | 2015-01-29 | 2017-01-18 | 杨威 | 一种jak/stat3磷酸化抑制剂及其制备方法与用途 |
| CN109776427B (zh) * | 2017-11-13 | 2022-08-23 | 沈阳中化农药化工研发有限公司 | 嘧啶双胺类化合物及其用途 |
| MX2021010319A (es) * | 2019-03-01 | 2021-12-10 | Revolution Medicines Inc | Compuestos biciclicos de heteroarilo y usos de estos. |
| CN115626893B (zh) * | 2022-10-10 | 2024-04-02 | 山西永津集团有限公司 | 一种2-羟基-5-羟甲基吡啶的合成方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1570494A (en) | 1975-11-28 | 1980-07-02 | Ici Ltd | Thienopyrimidine derivatives and their use as pesticides |
| US4196207A (en) * | 1977-05-23 | 1980-04-01 | Ici Australia Limited | Process for controlling eradicating or preventing infestations of animals by Ixodid ticks |
| GB2043061B (en) * | 1979-03-05 | 1983-05-11 | Ici Ltd | Thienopyrimidine and quinazoline derivatives |
| JPS5942387A (ja) * | 1982-07-21 | 1984-03-08 | Sankyo Co Ltd | チエノピリミジン誘導体および殺虫、殺ダニ剤 |
| EP0193885B1 (de) | 1985-03-02 | 1989-06-14 | BASF Aktiengesellschaft | Thiophenderivate |
| JPS6267A (ja) * | 1985-03-14 | 1987-01-06 | Sankyo Co Ltd | フエノキシアルキルアミン誘導体、その製法および殺虫殺ダニ剤 |
| US5141941A (en) * | 1988-11-21 | 1992-08-25 | Ube Industries, Ltd. | Aralkylamine derivatives, and fungicides containing the same |
| JPH0363265A (ja) * | 1989-08-02 | 1991-03-19 | Ube Ind Ltd | アルキルアミノピリミジン誘導体、その製造法及び殺虫・殺ダニ・殺線虫剤 |
| JPH075569B2 (ja) * | 1989-08-02 | 1995-01-25 | 宇部興産株式会社 | アラルキルアミン誘導体、その製法及び殺菌、殺虫剤 |
| US5124333A (en) * | 1989-08-02 | 1992-06-23 | Ube Industries, Ltd. | Aminopyrimidine derivatives and harmful organisms preventive agent |
| EP0424125A3 (en) | 1989-10-18 | 1991-10-09 | Ube Industries, Ltd. | Aralkylamine derivatives, preparation method thereof and fungicides containing the same |
| DE4008726A1 (de) * | 1990-03-19 | 1991-09-26 | Basf Ag | Thieno(2,3-d)pyrimidinderivate |
| US5137879A (en) * | 1990-03-30 | 1992-08-11 | Dowelanco | Furopyrimidin-4-imine derivatives |
| AU651337B2 (en) * | 1990-03-30 | 1994-07-21 | Dowelanco | Thienopyrimidine derivatives |
| JP2730019B2 (ja) * | 1990-04-06 | 1998-03-25 | 宇部興産株式会社 | アラルキルアミン誘導体，その製造法及び殺菌剤 |
| JP2762430B2 (ja) | 1991-01-18 | 1998-06-04 | 宇部興産株式会社 | アラルキルアミノピリミジン類の製法 |
| EP0519211A1 (de) * | 1991-05-17 | 1992-12-23 | Hoechst Schering AgrEvo GmbH | Substituierte 4-Aminopyrimidine, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel |
| JP3063266B2 (ja) | 1991-08-30 | 2000-07-12 | セイコーエプソン株式会社 | 液晶パネル及びその製造方法 |
| JPH0710712A (ja) * | 1993-06-25 | 1995-01-13 | Ube Ind Ltd | 花卉園芸用殺菌剤 |
| US5654307A (en) * | 1994-01-25 | 1997-08-05 | Warner-Lambert Company | Bicyclic compounds capable of inhibiting tyrosine kinases of the epidermal growth factor receptor family |
| GB9424676D0 (en) * | 1994-12-07 | 1995-02-01 | Sandoz Ltd | Organic compounds |
| US6232320B1 (en) * | 1998-06-04 | 2001-05-15 | Abbott Laboratories | Cell adhesion-inhibiting antiinflammatory compounds |
| AU4231299A (en) * | 1998-06-04 | 1999-12-20 | Abbott Laboratories | Cell adhesion-inhibiting antinflammatory compounds |
| CA2390948A1 (en) * | 1999-06-03 | 2000-12-14 | Abbott Laboratories | Cell adhesion-inhibiting antiinflammatory compounds |
| WO2003022214A2 (en) * | 2001-09-06 | 2003-03-20 | Millennium Pharmaceuticals, Inc. | Piperazine and homopiperazine compounds |
| AU2002357193A1 (en) | 2001-12-19 | 2003-07-09 | Smithkline Beecham Corporation | Thienopyrimidine compounds as protein tyrosine kinase inhibitors |
| WO2004092123A2 (en) * | 2003-04-10 | 2004-10-28 | Microbia, Inc. | Inhibitors of fungal invasion |
| ES2324536T7 (es) * | 2003-06-11 | 2012-03-16 | Xention Limited | Derivados de tenopirimidina como inhibidores de los canales de potasio. |
| GB0315950D0 (en) * | 2003-06-11 | 2003-08-13 | Xention Discovery Ltd | Compounds |
| US8008487B2 (en) * | 2004-10-21 | 2011-08-30 | Dow Agrosciences Llc | Substituted thieno[2,3-D]pyrimidines as fungicides |
-
2005
- 2005-10-21 US US11/256,117 patent/US8008487B2/en not_active Expired - Fee Related
- 2005-10-21 KR KR1020137034724A patent/KR20140008471A/ko not_active Withdrawn
- 2005-10-21 JP JP2007538127A patent/JP5122293B2/ja not_active Expired - Fee Related
- 2005-10-21 CN CN2005800440617A patent/CN101084224B/zh not_active Expired - Fee Related
- 2005-10-21 WO PCT/US2005/038145 patent/WO2006047397A1/en not_active Ceased
- 2005-10-21 KR KR1020147016709A patent/KR20140094626A/ko not_active Abandoned
- 2005-10-21 AT AT05812301T patent/ATE516291T1/de not_active IP Right Cessation
- 2005-10-21 BR BRPI0516242-4A patent/BRPI0516242B1/pt not_active IP Right Cessation
- 2005-10-21 KR KR1020077011335A patent/KR101386797B1/ko not_active Expired - Fee Related
- 2005-10-21 EP EP05812301A patent/EP1802632B1/en not_active Expired - Lifetime
-
2012
- 2012-05-01 JP JP2012104644A patent/JP5572664B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006047397A1 (en) | 2006-05-04 |
| JP2012180362A (ja) | 2012-09-20 |
| US8008487B2 (en) | 2011-08-30 |
| BRPI0516242A (pt) | 2008-08-26 |
| BRPI0516242B1 (pt) | 2014-10-07 |
| HK1118534A1 (en) | 2009-02-13 |
| ATE516291T1 (de) | 2011-07-15 |
| KR101386797B1 (ko) | 2014-04-21 |
| JP5122293B2 (ja) | 2013-01-16 |
| CN101084224B (zh) | 2013-12-04 |
| JP2008517936A (ja) | 2008-05-29 |
| JP5572664B2 (ja) | 2014-08-13 |
| US20060089370A1 (en) | 2006-04-27 |
| EP1802632B1 (en) | 2011-07-13 |
| CN101084224A (zh) | 2007-12-05 |
| KR20140094626A (ko) | 2014-07-30 |
| EP1802632A1 (en) | 2007-07-04 |
| KR20070063602A (ko) | 2007-06-19 |
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