UA73519C2 - Heterocyclic aromatic amide, fungicide mixture based thereon and a method for control or prevention of fungous affection - Google Patents
Heterocyclic aromatic amide, fungicide mixture based thereon and a method for control or prevention of fungous affection Download PDFInfo
- Publication number
- UA73519C2 UA73519C2 UA2002021418A UA2002021418A UA73519C2 UA 73519 C2 UA73519 C2 UA 73519C2 UA 2002021418 A UA2002021418 A UA 2002021418A UA 2002021418 A UA2002021418 A UA 2002021418A UA 73519 C2 UA73519 C2 UA 73519C2
- Authority
- UA
- Ukraine
- Prior art keywords
- mixture
- solution
- alkyl
- compound according
- aryl
- Prior art date
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 title claims abstract description 17
- 239000000203 mixture Substances 0.000 title claims description 346
- 238000000034 method Methods 0.000 title claims description 90
- 230000000855 fungicidal effect Effects 0.000 title claims description 14
- 239000000417 fungicide Substances 0.000 title claims description 14
- 230000002265 prevention Effects 0.000 title 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 226
- -1 arthropodicides Substances 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 43
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 125000003342 alkenyl group Chemical group 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000000304 alkynyl group Chemical group 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 20
- 125000004104 aryloxy group Chemical class 0.000 claims description 18
- 125000001188 haloalkyl group Chemical group 0.000 claims description 17
- 125000005110 aryl thio group Chemical group 0.000 claims description 15
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 12
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 12
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 125000004423 acyloxy group Chemical group 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 230000002538 fungal effect Effects 0.000 claims description 9
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 8
- 125000003368 amide group Chemical group 0.000 claims description 8
- 125000003435 aroyl group Chemical class 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004093 cyano group Chemical class *C#N 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 4
- 230000003902 lesion Effects 0.000 claims description 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 3
- 230000000895 acaricidal effect Effects 0.000 claims description 2
- 239000000642 acaricide Substances 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 claims description 2
- 239000003899 bactericide agent Substances 0.000 claims description 2
- 239000002917 insecticide Substances 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- 239000005645 nematicide Substances 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 241001026509 Kata Species 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 239000004009 herbicide Substances 0.000 claims 1
- 230000001069 nematicidal effect Effects 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 150000001408 amides Chemical group 0.000 abstract description 5
- 229940121375 antifungal agent Drugs 0.000 abstract description 5
- 239000003429 antifungal agent Substances 0.000 abstract description 3
- 239000000126 substance Substances 0.000 description 251
- 239000007787 solid Substances 0.000 description 245
- 239000000243 solution Substances 0.000 description 225
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 208
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 144
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 120
- 150000001412 amines Chemical class 0.000 description 91
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 91
- 239000003921 oil Substances 0.000 description 90
- 235000019198 oils Nutrition 0.000 description 90
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 84
- 230000012010 growth Effects 0.000 description 71
- 239000011541 reaction mixture Substances 0.000 description 71
- 230000004224 protection Effects 0.000 description 70
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 64
- 238000002360 preparation method Methods 0.000 description 64
- 239000002904 solvent Substances 0.000 description 55
- 239000010410 layer Substances 0.000 description 47
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- 238000003756 stirring Methods 0.000 description 43
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 42
- 238000004949 mass spectrometry Methods 0.000 description 42
- 241000196324 Embryophyta Species 0.000 description 41
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 37
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical class C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 37
- 239000012074 organic phase Substances 0.000 description 36
- 239000000741 silica gel Substances 0.000 description 36
- 229910002027 silica gel Inorganic materials 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
- 239000012044 organic layer Substances 0.000 description 35
- 238000005160 1H NMR spectroscopy Methods 0.000 description 34
- 235000019439 ethyl acetate Nutrition 0.000 description 34
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 29
- 239000003480 eluent Substances 0.000 description 28
- 229920006395 saturated elastomer Polymers 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 25
- 238000004587 chromatography analysis Methods 0.000 description 25
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 24
- 239000013078 crystal Substances 0.000 description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 22
- 150000002500 ions Chemical class 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- 239000001257 hydrogen Substances 0.000 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 239000012261 resinous substance Substances 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 19
- 238000001819 mass spectrum Methods 0.000 description 19
- 239000002253 acid Substances 0.000 description 18
- 239000007864 aqueous solution Substances 0.000 description 18
- 150000002923 oximes Chemical class 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 17
- 239000008346 aqueous phase Substances 0.000 description 17
- 239000000284 extract Substances 0.000 description 17
- 239000000725 suspension Substances 0.000 description 17
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 16
- MCNQUWLLXZZZAC-UHFFFAOYSA-N 4-cyano-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-n-piperidin-1-ylpyrazole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=C(C#N)C(C(=O)NN2CCCCC2)=NN1C1=CC=C(Cl)C=C1Cl MCNQUWLLXZZZAC-UHFFFAOYSA-N 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 15
- 150000001793 charged compounds Chemical class 0.000 description 15
- 239000012230 colorless oil Substances 0.000 description 15
- 238000001816 cooling Methods 0.000 description 15
- 239000000543 intermediate Substances 0.000 description 15
- 239000007788 liquid Substances 0.000 description 15
- 238000000746 purification Methods 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 14
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 14
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 241000209140 Triticum Species 0.000 description 13
- 239000012299 nitrogen atmosphere Substances 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 235000021307 Triticum Nutrition 0.000 description 12
- 239000012267 brine Substances 0.000 description 12
- 238000003818 flash chromatography Methods 0.000 description 12
- 150000002576 ketones Chemical class 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
- 239000012298 atmosphere Substances 0.000 description 11
- 201000010099 disease Diseases 0.000 description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 241000233866 Fungi Species 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
- 229910052794 bromium Inorganic materials 0.000 description 10
- 230000005764 inhibitory process Effects 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 239000012047 saturated solution Substances 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 9
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 9
- 238000009739 binding Methods 0.000 description 9
- 238000009833 condensation Methods 0.000 description 9
- 230000005494 condensation Effects 0.000 description 9
- 238000005984 hydrogenation reaction Methods 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 230000002401 inhibitory effect Effects 0.000 description 9
- 238000006268 reductive amination reaction Methods 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 9
- 239000004473 Threonine Substances 0.000 description 8
- 239000007900 aqueous suspension Substances 0.000 description 8
- 235000013405 beer Nutrition 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- SOONMTSDZMMKLJ-UHFFFAOYSA-N 6-bromo-4-methoxy-3-phenylmethoxypyridine-2-carbonyl chloride Chemical compound COC1=CC(Br)=NC(C(Cl)=O)=C1OCC1=CC=CC=C1 SOONMTSDZMMKLJ-UHFFFAOYSA-N 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 239000013543 active substance Substances 0.000 description 7
- 235000019270 ammonium chloride Nutrition 0.000 description 7
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 7
- 238000011161 development Methods 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 239000012259 ether extract Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 230000005484 gravity Effects 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 7
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- 239000012258 stirred mixture Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 208000031888 Mycoses Diseases 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 150000001241 acetals Chemical class 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 239000012300 argon atmosphere Substances 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000013504 emergency use authorization Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 235000013305 food Nutrition 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 238000007429 general method Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- 239000003415 peat Substances 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 239000011343 solid material Substances 0.000 description 6
- 238000009736 wetting Methods 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 5
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 5
- DVKWJLMEZRXDHI-UHFFFAOYSA-N 7-(furan-2-yl)-3-methyl-2,3-dihydrochromen-4-one Chemical compound C=1C=C2C(=O)C(C)COC2=CC=1C1=CC=CO1 DVKWJLMEZRXDHI-UHFFFAOYSA-N 0.000 description 5
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 5
- 239000005695 Ammonium acetate Substances 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- 101000939500 Homo sapiens UBX domain-containing protein 11 Proteins 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- 102100029645 UBX domain-containing protein 11 Human genes 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 235000019257 ammonium acetate Nutrition 0.000 description 5
- 229940043376 ammonium acetate Drugs 0.000 description 5
- 150000001540 azides Chemical class 0.000 description 5
- PEHLCCGXTLWMRW-UHFFFAOYSA-N bis-lactone Chemical compound C1CC2OC(=O)C3C1OC(=O)C32 PEHLCCGXTLWMRW-UHFFFAOYSA-N 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 229940125851 compound 27 Drugs 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 239000010779 crude oil Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 150000001261 hydroxy acids Chemical class 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 239000012280 lithium aluminium hydride Substances 0.000 description 5
- 239000002808 molecular sieve Substances 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 5
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- DNRFJJMFYWJGIY-UHFFFAOYSA-N trimethyl-[2-(pyridin-3-yloxymethoxy)ethyl]silane Chemical compound C[Si](C)(C)CCOCOC1=CC=CN=C1 DNRFJJMFYWJGIY-UHFFFAOYSA-N 0.000 description 5
- 235000014101 wine Nutrition 0.000 description 5
- 239000002023 wood Substances 0.000 description 5
- UNNNAIWPDLRVRN-UHFFFAOYSA-N 1-fluoro-4-(trifluoromethyl)benzene Chemical compound FC1=CC=C(C(F)(F)F)C=C1 UNNNAIWPDLRVRN-UHFFFAOYSA-N 0.000 description 4
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- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 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
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- 238000013207 serial dilution Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
- 229910001958 silver carbonate Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
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- ADNPLDHMAVUMIW-CUZNLEPHSA-N substance P Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CCCN=C(N)N)C1=CC=CC=C1 ADNPLDHMAVUMIW-CUZNLEPHSA-N 0.000 description 1
- JOKPITBUODAHEN-UHFFFAOYSA-N sulfanylideneplatinum Chemical compound [Pt]=S JOKPITBUODAHEN-UHFFFAOYSA-N 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 239000000057 synthetic resin Substances 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005607 tigloyl group Chemical group 0.000 description 1
- 238000004448 titration Methods 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
- ZGYICYBLPGRURT-UHFFFAOYSA-N tri(propan-2-yl)silicon Chemical compound CC(C)[Si](C(C)C)C(C)C ZGYICYBLPGRURT-UHFFFAOYSA-N 0.000 description 1
- SANWDQJIWZEKOD-UHFFFAOYSA-N tributyl(furan-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CO1 SANWDQJIWZEKOD-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 235000016788 valerian Nutrition 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- 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
- C07D495/08—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US14467699P | 1999-07-20 | 1999-07-20 | |
PCT/US2000/019794 WO2001005769A2 (en) | 1999-07-20 | 2000-07-20 | Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation |
Publications (1)
Publication Number | Publication Date |
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UA73519C2 true UA73519C2 (en) | 2005-08-15 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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UA2002021418A UA73519C2 (en) | 1999-07-20 | 2000-07-20 | Heterocyclic aromatic amide, fungicide mixture based thereon and a method for control or prevention of fungous affection |
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Country | Link |
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US (3) | US6521622B1 (ko) |
EP (1) | EP1196388A2 (ko) |
JP (1) | JP2003528806A (ko) |
KR (1) | KR100743262B1 (ko) |
CN (1) | CN1208321C (ko) |
AU (1) | AU780698B2 (ko) |
BR (1) | BR0012615A (ko) |
CA (1) | CA2374995C (ko) |
CR (1) | CR6557A (ko) |
CZ (1) | CZ2002219A3 (ko) |
DK (1) | DK1516874T3 (ko) |
ES (1) | ES2546386T3 (ko) |
HU (1) | HUP0301764A3 (ko) |
PL (1) | PL206415B1 (ko) |
TR (1) | TR200200587T2 (ko) |
UA (1) | UA73519C2 (ko) |
WO (1) | WO2001005769A2 (ko) |
ZA (1) | ZA200200436B (ko) |
Families Citing this family (96)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20020177578A1 (en) | 1999-07-20 | 2002-11-28 | Ricks Michael J. | Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation |
US6355660B1 (en) | 1999-07-20 | 2002-03-12 | Dow Agrosciences Llc | Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation |
JP2003507474A (ja) * | 1999-08-20 | 2003-02-25 | フレッド ハッチンソン キャンサー リサーチ センター | bcl−2ファミリーメンバータンパク質を過剰発現する細胞においてアポトーシスを調節するための組成物および方法 |
EP1234827A3 (en) * | 1999-08-20 | 2003-06-18 | Dow AgroSciences LLC | Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation |
CZ2002487A3 (cs) * | 1999-08-20 | 2002-06-12 | Dow Agrosciences Llc | Fungicidní heterocyklické aromatické amidy, prostředky na jejich bázi, způsoby jejich pouľití a přípravy |
FR2803592A1 (fr) * | 2000-01-06 | 2001-07-13 | Aventis Cropscience Sa | Nouveaux derives de l'acide 3-hydroxypicolinique, leur procede de preparation et compositions fongicides les contenant. |
US7241804B1 (en) | 2000-08-18 | 2007-07-10 | Fred Hutchinson Cancer Research Center | Compositions and methods for modulating apoptosis in cells over-expressing Bcl-2 family member proteins |
WO2002022583A2 (en) * | 2000-09-18 | 2002-03-21 | E. I. Du Pont De Nemours And Company | Pyridinyl amides and imides for use as fungicides |
WO2002080928A1 (en) * | 2001-04-03 | 2002-10-17 | Merck & Co., Inc. | N-substituted nonaryl-heterocyclo amidyl nmda/nr2b antagonists |
FR2827286A1 (fr) | 2001-07-11 | 2003-01-17 | Aventis Cropscience Sa | Nouveaux composes fongicides |
US6987123B2 (en) | 2001-07-26 | 2006-01-17 | Cadila Healthcare Limited | Heterocyclic compounds, their preparation, pharmaceutical compositions containing them and their use in medicine |
EP1412351A4 (en) * | 2001-07-31 | 2005-04-06 | Dow Agrosciences Llc | REDUCTIVE CLEAVAGE OF THE EXOCYCLIC ESTERS OF UK 2A OR BZW. DERIVATIVES AND PRODUCTS MADE THEREFROM |
DE10161765A1 (de) | 2001-12-15 | 2003-07-03 | Bayer Cropscience Gmbh | Substituierte Phenylderivate |
WO2003059258A2 (en) | 2001-12-21 | 2003-07-24 | Cytokinetics, Inc. | Compositions and methods for treating heart failure |
EP2130820A1 (en) * | 2002-02-19 | 2009-12-09 | Shionogi & Co., Ltd. | Antipruritics |
EP1587796A1 (en) * | 2003-01-31 | 2005-10-26 | AstraZeneca AB | Saturated quinoxaline derivatives and their use as metabotropic glutamate receptor ligands |
BRPI0413324A (pt) * | 2003-08-06 | 2006-10-10 | Senomyx Inc | receptores de paladar hetero-oligoméricos t1r, linhas de células que expressam os ditos receptores, e compostos de paladar |
WO2005042524A1 (en) * | 2003-10-30 | 2005-05-12 | Virochem Pharma Inc. | Pyridine carboxamide and methods for inhibiting hiv integrase |
EP1548007A1 (en) | 2003-12-19 | 2005-06-29 | Bayer CropScience S.A. | 2-Pyridinylethylcarboxamide derivatives and their use as fungicides |
KR100857312B1 (ko) * | 2004-01-28 | 2008-09-05 | 미쓰이 가가쿠 가부시키가이샤 | 아미드 유도체 및 그 제조 방법 및 그의 살충제로서의 사용 방법 |
EP1574511A1 (en) * | 2004-03-03 | 2005-09-14 | Bayer CropScience S.A. | 2-Pyridinylethylcarboxamide derivatives and their use as fungicides |
US7459562B2 (en) * | 2004-04-23 | 2008-12-02 | Bristol-Myers Squibb Company | Monocyclic heterocycles as kinase inhibitors |
TW200538453A (en) * | 2004-04-26 | 2005-12-01 | Bristol Myers Squibb Co | Bicyclic heterocycles as kinase inhibitors |
US20050288290A1 (en) | 2004-06-28 | 2005-12-29 | Borzilleri Robert M | Fused heterocyclic kinase inhibitors |
US7432373B2 (en) * | 2004-06-28 | 2008-10-07 | Bristol-Meyers Squibb Company | Processes and intermediates useful for preparing fused heterocyclic kinase inhibitors |
US7439246B2 (en) * | 2004-06-28 | 2008-10-21 | Bristol-Myers Squibb Company | Fused heterocyclic kinase inhibitors |
WO2006105217A2 (en) | 2005-03-31 | 2006-10-05 | Schering Corporation | Spirocyclic thrombin receptor antagonists |
EP1887002B1 (en) * | 2005-05-31 | 2015-08-26 | Sumitomo Chemical Company, Limited | Carboxamide compound and use thereof |
US8067638B2 (en) * | 2005-06-21 | 2011-11-29 | Mitsui Chemicals, Inc. | Amide derivative and insecticide containing the same |
JP5003014B2 (ja) * | 2005-07-14 | 2012-08-15 | 住友化学株式会社 | カルボキサミド化合物及びその植物病害防除用途 |
CA2616749C (en) * | 2005-07-27 | 2012-01-03 | Mitsui Chemicals, Inc. | Composition for preventing harmful organisms |
WO2007107470A2 (en) | 2006-03-22 | 2007-09-27 | F. Hoffmann-La Roche Ag | Pyrazoles as 11-beta-hsd-1 |
EP2089364B1 (en) * | 2006-11-08 | 2013-06-12 | Bristol-Myers Squibb Company | Pyridinone compounds |
JP2010534722A (ja) * | 2007-07-27 | 2010-11-11 | ブリストル−マイヤーズ スクイブ カンパニー | 新規グルコキナーゼ活性化薬およびその使用方法 |
US20100286131A1 (en) * | 2007-08-03 | 2010-11-11 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
CA2693997C (en) * | 2007-08-03 | 2013-01-15 | Pierre L. Beaulieu | Viral polymerase inhibitors |
EP2234977A4 (en) * | 2007-12-19 | 2011-04-13 | Boehringer Ingelheim Int | VIRAL POLYMERASE INHIBITORS |
KR101596527B1 (ko) * | 2008-01-23 | 2016-02-22 | 브리스톨-마이어스 스큅 컴퍼니 | 4-피리디논 화합물 및 암에 대한 그의 용도 |
CA2722621A1 (en) * | 2008-03-26 | 2009-10-01 | Orthologic Corp. | Thrombin derived peptides for smooth muscle relaxation |
ES2552820T3 (es) * | 2008-05-30 | 2015-12-02 | Dow Agrosciences Llc | Métodos para combatir patógenos fúngicos QoI-resistentes |
EP3153020B1 (en) * | 2009-10-07 | 2018-11-28 | Dow AgroSciences LLC | Synergistic fungicidial mixtures for fungal control in cereals |
EP2485732A4 (en) * | 2009-10-07 | 2013-10-09 | Dow Agrosciences Llc | SYNERGISTIC FUNGICIDE COMPOSITION CONTAINING 5-FLUOROCYTOSINE FOR CONTROL OF CEREAL FUNGI |
WO2011156174A1 (en) * | 2010-06-07 | 2011-12-15 | Dow Agrosciences Llc | Pyrazinyl carboxamides as fungicides |
CN102351783B (zh) * | 2011-08-23 | 2015-11-18 | 李建东 | 1-苄基-3-哌啶酮盐酸盐的合成方法 |
WO2013150988A1 (ja) | 2012-04-03 | 2013-10-10 | 三井化学アグロ株式会社 | アルキル化芳香族アミド誘導体の製造方法 |
RU2014149186A (ru) | 2012-05-07 | 2016-06-27 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Макроциклические пиколинамиды в качестве фунгицидов |
AU2013259790B2 (en) | 2012-05-07 | 2016-09-08 | Corteva Agriscience Llc | Use of pro-fungicides of UK-2A for control of Black Sigatoka |
EP2847187A4 (en) | 2012-05-07 | 2015-10-28 | Dow Agrosciences Llc | MACROCYCLIC PICOLINAMIDE AS FUNGICIDES |
ES2666144T3 (es) | 2012-12-28 | 2018-05-03 | Dow Agrosciences Llc | Mezclas fungicidas sinérgicas para control fúngico en cereales |
US9482661B2 (en) | 2012-12-31 | 2016-11-01 | Dow Agrosciences Llc | Synthesis and use of isotopically labeled macrocyclic compounds |
PL2938190T3 (pl) | 2012-12-31 | 2018-05-30 | Dow Agrosciences Llc | Makrocykliczne pikolinamidy jako fungicydy |
US9439422B2 (en) | 2013-10-01 | 2016-09-13 | Dow Agrosciences Llc | Use of macrocyclic picolinamides as fungicides |
CN105705502A (zh) * | 2013-10-01 | 2016-06-22 | 美国陶氏益农公司 | 具有杀真菌活性的大环吡啶酰胺化合物 |
CN103651352B (zh) * | 2013-11-18 | 2015-05-13 | 四川大学 | N-(2-苯氧基苯)苯甲酰胺类化合物作为农用杀菌剂的新用途 |
CN103664844A (zh) * | 2013-11-18 | 2014-03-26 | 四川大学 | N-(2-苯氧基苯)呋喃甲酰胺类化合物及其制备方法和杀菌活性 |
US9247741B2 (en) | 2013-12-26 | 2016-02-02 | Dow Agrosciences Llc | Use of macrocyclic picolinamides as fungicides |
US9549556B2 (en) | 2013-12-26 | 2017-01-24 | Dow Agrosciences Llc | Macrocyclic picolinamides as fungicides |
CN106061260A (zh) | 2013-12-31 | 2016-10-26 | 美国陶氏益农公司 | 用于谷类中真菌防治的协同杀真菌混合物 |
US20150322051A1 (en) | 2014-05-06 | 2015-11-12 | Dow Agrosciences Llc | Macrocyclic picolinamides as fungicides |
CN106660959B (zh) * | 2014-07-08 | 2019-12-03 | 美国陶氏益农公司 | 3-羟基吡啶甲酸的制备方法 |
JP6513178B2 (ja) | 2014-07-08 | 2019-05-15 | ダウ アグロサイエンシィズ エルエルシー | 4−アルコキシ−3−ヒドロキシピコリン酸の製造方法 |
EP3166936A4 (en) | 2014-07-08 | 2017-11-22 | Dow AgroSciences LLC | Macrocyclic picolinamides as fungicides |
BR112017000104A2 (pt) | 2014-07-08 | 2017-10-31 | Dow Agrosciences Llc | picolinamidas macrocíclicas como fungicidas |
WO2016069370A1 (en) * | 2014-10-28 | 2016-05-06 | Dow Agrosciences Llc | Macrocyclic picolinamides as fungicides |
RU2703402C2 (ru) | 2014-12-30 | 2019-10-16 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Пиколинамиды с фунгицидной активностью |
RU2702697C2 (ru) * | 2014-12-30 | 2019-10-09 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Использование пиколинамидных соединений с фунгицидной активностью |
AU2015374458B2 (en) * | 2014-12-30 | 2018-02-15 | Dow Agrosciences Llc | Use of picolinamide compounds with fungicidal activity |
CA2972091A1 (en) | 2014-12-30 | 2016-07-07 | Dow Agrosciences Llc | Fungicidal compositions comprising a derivative of uk-2a |
US20180002320A1 (en) * | 2014-12-30 | 2018-01-04 | Dow Agrosciences Llc | Use of macrocyclic picolinamides as fungicides |
WO2016109305A1 (en) | 2014-12-30 | 2016-07-07 | Dow Agrosciences Llc | Use of picolinamides as fungicides |
CA2972405A1 (en) | 2014-12-30 | 2016-07-07 | Dow Agrosciences Llc | Use of picolinamide compounds as fungicides |
WO2016109290A1 (en) * | 2014-12-30 | 2016-07-07 | Dow Agrosciences Llc | Macrocyclic picolinamide compounds with fungicidal activity |
BR112018008947A8 (pt) * | 2015-11-04 | 2019-02-26 | Syngenta Participations Ag | derivados de anilida microbiocidas |
CA3011928A1 (en) | 2016-01-22 | 2017-07-27 | Dow Agrosciences Llc | Process for the preparation of 4-alkoxy-3-hydroxypicolinic acids |
TW201733985A (zh) * | 2016-02-29 | 2017-10-01 | 陶氏農業科學公司 | 用於製備4-烷氧基-3-羥基吡啶甲酸之方法 |
WO2018045003A1 (en) | 2016-08-30 | 2018-03-08 | Dow Agrosciences Llc | Picolinamide n-oxide compounds with fungicidal activity |
US10334852B2 (en) | 2016-08-30 | 2019-07-02 | Dow Agrosciences Llc | Pyrido-1,3-oxazine-2,4-dione compounds with fungicidal activity |
US10231452B2 (en) | 2016-08-30 | 2019-03-19 | Dow Agrosciences Llc | Thiopicolinamide compounds with fungicidal activity |
WO2018044996A1 (en) | 2016-08-30 | 2018-03-08 | Dow Agrosciences Llc | Picolinamides as fungicides |
WO2018081167A1 (en) | 2016-10-24 | 2018-05-03 | Yumanity Therapeutics | Compounds and uses thereof |
BR102018000183B1 (pt) | 2017-01-05 | 2023-04-25 | Dow Agrosciences Llc | Picolinamidas, composição para controle de um patógeno fúngico, e método para controle e prevenção de um ataque por fungos em uma planta |
TWI774761B (zh) | 2017-05-02 | 2022-08-21 | 美商科迪華農業科技有限責任公司 | 用於穀物中的真菌防治之協同性混合物 |
EP3618626A4 (en) | 2017-05-02 | 2020-12-02 | Dow Agrosciences LLC | USE OF AN ACYCLIC PICOLINAMIDE COMPOUND AS A FUNGICIDE FOR FUNGAL GRASS INFESTATION |
TW201842851A (zh) | 2017-05-02 | 2018-12-16 | 美商陶氏農業科學公司 | 用於穀類中的真菌防治之協同性混合物 |
CA3083000A1 (en) | 2017-10-24 | 2019-05-02 | Yumanity Therapeutics, Inc. | Compounds and uses thereof |
US11365175B2 (en) | 2017-11-03 | 2022-06-21 | Isagro S.P.A. | Aromatic amides having a fungicidal activity, their agronomic compositions and relative preparation method |
BR112020009659A2 (pt) * | 2017-11-15 | 2020-11-10 | Syngenta Participations Ag | derivados picolinamida microbiocidas |
BR102019004480B1 (pt) | 2018-03-08 | 2023-03-28 | Dow Agrosciences Llc | Picolinamidas como fungicidas |
CN110776457B (zh) * | 2018-07-26 | 2023-07-14 | 华中师范大学 | 含三氟甲基吡啶酰胺类化合物及其制备方法和应用以及杀菌剂 |
CA3115684A1 (en) | 2018-10-15 | 2020-04-23 | Dow Agrosciences Llc | Methods for sythesis of oxypicolinamides |
CA3127791A1 (en) | 2019-01-24 | 2020-07-30 | Yumanity Therapeutics, Inc. | Compounds and uses thereof |
IT201900006543A1 (it) | 2019-05-06 | 2020-11-06 | Isagro Spa | Composti ad attività fungicida, relative composizioni agronomiche e uso per il controllo di funghi fitopatogeni |
IT201900011127A1 (it) | 2019-07-08 | 2021-01-08 | Isagro Spa | Composti ad attività fungicida, relative composizioni agronomiche e uso per il controllo di funghi fitopatogeni |
IT201900021960A1 (it) | 2019-11-22 | 2021-05-22 | Isagro Spa | Composti ad attività fungicida, loro composizioni agronomiche e relativo metodo di preparazione |
IT202000007234A1 (it) | 2020-04-06 | 2021-10-06 | Isagro Spa | Composti ad attività fungicida, relative composizioni agronomiche e uso per il controllo di funghi fitopatogeni |
CN116874541B (zh) * | 2023-07-17 | 2024-02-20 | 潍坊市阳光化工股份有限公司 | 一种植物生长调节剂及其制备方法 |
Family Cites Families (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH415630A (de) | 1962-09-26 | 1966-06-30 | Geigy Ag J R | Verfahren zur Herstellung von Picolinsäurederivaten |
DE1217385B (de) * | 1962-11-09 | 1966-05-26 | J. R. Geigy A.-G., Basel (Schweiz) | Verfahren zur Herstellung von neuen Picolinsäurederivafen |
BE639691A (ko) * | 1963-11-08 | |||
DE2150772A1 (de) | 1971-10-12 | 1973-04-19 | Cassella Farbwerke Mainkur Ag | Verfahren zur herstellung von 6-hydroxy-2-pyridon-3-carbonsaeureamidverbindungen |
US4202900A (en) * | 1972-09-27 | 1980-05-13 | Ciba-Geigy Corporation | Derivatives of penam-3-carboxylic acid and a pharmaceutical composition containing the same |
DE3513259A1 (de) | 1985-04-13 | 1986-10-23 | Bayer Ag, 5090 Leverkusen | Heterocyclische amid-derivate |
DE3687123T2 (de) | 1986-01-24 | 1993-05-13 | Terumo Corp | Ionenempfindlicher fet-fuehler. |
US5495023A (en) * | 1991-11-15 | 1996-02-27 | Fujisawa Pharmaceutical Co., Ltd. | Nitro compounds, process for preparation thereof and use thereof |
DE4138819A1 (de) | 1991-11-26 | 1993-05-27 | Basf Ag | Hydroxypyridoncarbonsaeureamide, deren herstellung und verwendung |
DE4227747A1 (de) * | 1992-08-21 | 1994-02-24 | Basf Ag | Heteroaromatisch kondensierte Hydroxypyridoncarbonsäureamide, deren Herstellung und Verwendung |
NZ270267A (en) | 1993-12-30 | 1997-03-24 | Hoechst Ag | 3-hydroxypyridin-2yl (and -quinolin-2-yl) carboxamide derivatives and pharmaceutical compositions |
JP3526602B2 (ja) * | 1994-02-24 | 2004-05-17 | サントリー株式会社 | 新規抗真菌化合物 |
JPH08152428A (ja) * | 1994-02-25 | 1996-06-11 | Fujisawa Pharmaceut Co Ltd | Noガス測定用試薬 |
US5616590A (en) * | 1994-06-30 | 1997-04-01 | Ciba-Geigy Corporation | Plant microbicides |
DE4425616A1 (de) | 1994-07-20 | 1996-01-25 | Basf Ag | Hydroxypyridoncarbonsäureamide, deren Herstellung und Verwendung |
JPH11510788A (ja) | 1995-05-24 | 1999-09-21 | ノバルティス アクチェンゲゼルシャフト | ピリジン殺菌剤 |
EP0848700B1 (de) | 1995-08-30 | 2003-07-02 | Bayer CropScience AG | Acylaminosalicylsäureamide und ihre verwendung als schädlingsbekämpfungsmittel |
EP0891975A4 (en) | 1996-04-05 | 2000-03-15 | Mitsubishi Chem Corp | PYRAZOLES AND CHEMICALS FOR AGRICULTURE THAT CONTAIN THEM AS ACTIVE INGREDIENTS |
DE69702094T2 (de) | 1996-06-28 | 2001-02-01 | Rohm And Haas Co., Philadelphia | N-Acetonylbenzamidverbindungen mit fungizider Aktivität |
DE19650215A1 (de) | 1996-12-04 | 1998-06-10 | Hoechst Ag | 3-Hydroxypyridin-2-carbonsäureamidester, ihre Herstellung und ihre Verwendung als Arzneimittel |
AU8887898A (en) * | 1997-08-29 | 1999-03-22 | Meiji Seika Kaisha Ltd. | Rice blast control agent and wheat scab control agent |
US6113778A (en) | 1997-11-03 | 2000-09-05 | Komline-Sanderson Limited | Pressure plate filter with horizontal filter plates |
NZ506249A (en) * | 1998-02-06 | 2003-04-29 | Meiji Seika Kaisha | Antifungal compounds and process for producing the same from UK-2 |
JPH11228542A (ja) * | 1998-02-10 | 1999-08-24 | Meiji Seika Kaisha Ltd | 新規抗真菌剤 |
JP2929006B1 (ja) | 1998-07-08 | 1999-08-03 | 工業技術院長 | 高品質結晶薄板材料の製造方法 |
WO2000026191A1 (fr) * | 1998-11-04 | 2000-05-11 | Meiji Seika Kaisha, Ltd. | Derives de picolinamide et pesticides contenant ces derives comme ingredient actif |
WO2000076979A1 (de) | 1999-06-09 | 2000-12-21 | Bayer Aktiengesellschaft | Pyridincarboxamide und ihre verwendung als pflanzenschutzmittel |
CZ2002487A3 (cs) * | 1999-08-20 | 2002-06-12 | Dow Agrosciences Llc | Fungicidní heterocyklické aromatické amidy, prostředky na jejich bázi, způsoby jejich pouľití a přípravy |
FR2803592A1 (fr) * | 2000-01-06 | 2001-07-13 | Aventis Cropscience Sa | Nouveaux derives de l'acide 3-hydroxypicolinique, leur procede de preparation et compositions fongicides les contenant. |
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- 2000-07-20 DK DK04027006.8T patent/DK1516874T3/en active
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- 2000-07-20 BR BR0012615-2A patent/BR0012615A/pt not_active Application Discontinuation
- 2000-07-20 AU AU63572/00A patent/AU780698B2/en not_active Ceased
- 2000-07-20 US US09/620,662 patent/US6521622B1/en not_active Expired - Lifetime
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- 2000-07-20 KR KR1020027000677A patent/KR100743262B1/ko not_active IP Right Cessation
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HUP0301764A3 (en) | 2004-06-28 |
EP1196388A2 (en) | 2002-04-17 |
KR20020040753A (ko) | 2002-05-30 |
KR100743262B1 (ko) | 2007-07-27 |
JP2003528806A (ja) | 2003-09-30 |
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CZ2002219A3 (cs) | 2002-10-16 |
AU780698B2 (en) | 2005-04-14 |
CN1450993A (zh) | 2003-10-22 |
US6927225B2 (en) | 2005-08-09 |
HUP0301764A2 (hu) | 2003-09-29 |
WO2001005769A3 (en) | 2001-11-22 |
US20040034025A1 (en) | 2004-02-19 |
US20040048864A1 (en) | 2004-03-11 |
CA2374995C (en) | 2010-12-07 |
TR200200587T2 (tr) | 2004-12-21 |
CR6557A (es) | 2008-09-22 |
WO2001005769A2 (en) | 2001-01-25 |
ZA200200436B (en) | 2004-05-26 |
PL206415B1 (pl) | 2010-08-31 |
CN1208321C (zh) | 2005-06-29 |
US7034035B2 (en) | 2006-04-25 |
ES2546386T3 (es) | 2015-09-23 |
BR0012615A (pt) | 2004-03-30 |
CA2374995A1 (en) | 2001-01-25 |
AU6357200A (en) | 2001-02-05 |
DK1516874T3 (en) | 2015-11-23 |
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