CZ291264B6 - Kondenzované bicyklické pyrimidinony, fungicidní prostředek a způsob potlačování padlí travního - Google Patents
Kondenzované bicyklické pyrimidinony, fungicidní prostředek a způsob potlačování padlí travního Download PDFInfo
- Publication number
- CZ291264B6 CZ291264B6 CZ19952803A CZ280395A CZ291264B6 CZ 291264 B6 CZ291264 B6 CZ 291264B6 CZ 19952803 A CZ19952803 A CZ 19952803A CZ 280395 A CZ280395 A CZ 280395A CZ 291264 B6 CZ291264 B6 CZ 291264B6
- Authority
- CZ
- Czechia
- Prior art keywords
- bromo
- compounds
- powdery mildew
- hydrogen
- wheat
- Prior art date
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- -1 bicyclic pyrimidinones Chemical class 0.000 title claims abstract description 26
- 241000209140 Triticum Species 0.000 title claims abstract description 24
- 235000021307 Triticum Nutrition 0.000 title claims abstract description 24
- 241000221785 Erysiphales Species 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims abstract description 16
- 239000000417 fungicide Substances 0.000 title claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 7
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 38
- 125000001246 bromo group Chemical group Br* 0.000 claims description 32
- 241000196324 Embryophyta Species 0.000 claims description 29
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- YCIPQJTZJGUXND-UHFFFAOYSA-N Aglaia odorata Alkaloid Natural products C1=CC(OC)=CC=C1C1(C(C=2C(=O)N3CCCC3=NC=22)C=3C=CC=CC=3)C2(O)C2=C(OC)C=C(OC)C=C2O1 YCIPQJTZJGUXND-UHFFFAOYSA-N 0.000 claims description 13
- 125000002619 bicyclic group Chemical group 0.000 claims description 13
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 11
- 230000000855 fungicidal effect Effects 0.000 claims description 9
- 239000004094 surface-active agent Substances 0.000 claims description 9
- 230000009471 action Effects 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- FLVBXVXXXMLMOX-UHFFFAOYSA-N proquinazid Chemical compound C1=C(I)C=C2C(=O)N(CCC)C(OCCC)=NC2=C1 FLVBXVXXXMLMOX-UHFFFAOYSA-N 0.000 claims description 3
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 2
- QQLGQHGKSPJXTO-UHFFFAOYSA-N 6,8-diiodo-2-propoxy-3-propylquinazolin-4-one Chemical compound C1=C(I)C=C2C(=O)N(CCC)C(OCCC)=NC2=C1I QQLGQHGKSPJXTO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- GZLYSDJGEXGQDO-UHFFFAOYSA-N C1=CC=CC2=NCNC=C21 Chemical compound C1=CC=CC2=NCNC=C21 GZLYSDJGEXGQDO-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 3
- 150000002367 halogens Chemical class 0.000 abstract description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052794 bromium Inorganic materials 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- 239000000725 suspension Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
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- 229920006395 saturated elastomer Polymers 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002540 isothiocyanates Chemical class 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
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- 238000000605 extraction Methods 0.000 description 3
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
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- 238000004809 thin layer chromatography Methods 0.000 description 3
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 3
- XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 description 2
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 description 2
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 2
- LQDARGUHUSPFNL-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COC(F)(F)C(F)F)CN1C=NC=N1 LQDARGUHUSPFNL-UHFFFAOYSA-N 0.000 description 2
- MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 description 2
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 2
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 2
- LHZQTWZRKDRJGT-UHFFFAOYSA-N 2-methylsulfanyl-1h-quinazolin-4-one Chemical compound C1=CC=C2C(=O)NC(SC)=NC2=C1 LHZQTWZRKDRJGT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000895502 Blumeria graminis f. sp. tritici Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000005756 Cymoxanil Substances 0.000 description 2
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
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- CIEXPHRYOLIQQD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-2-furoylalaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)C1=CC=CO1 CIEXPHRYOLIQQD-UHFFFAOYSA-N 0.000 description 1
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- KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
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- 238000003359 percent control normalization Methods 0.000 description 1
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- 235000020030 perry Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 1
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
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- 229910052717 sulfur Inorganic materials 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
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- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
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- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms
-
- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6062993A | 1993-05-12 | 1993-05-12 | |
| US14490493A | 1993-10-28 | 1993-10-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ280395A3 CZ280395A3 (en) | 1996-03-13 |
| CZ291264B6 true CZ291264B6 (cs) | 2003-01-15 |
Family
ID=26740142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ19952803A CZ291264B6 (cs) | 1993-05-12 | 1994-05-10 | Kondenzované bicyklické pyrimidinony, fungicidní prostředek a způsob potlačování padlí travního |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US5747497A (en, 2012) |
| EP (1) | EP0698013B1 (en, 2012) |
| JP (1) | JPH08510243A (en, 2012) |
| CN (1) | CN1050355C (en, 2012) |
| AT (1) | ATE206406T1 (en, 2012) |
| AU (1) | AU6944394A (en, 2012) |
| BR (1) | BR9406662A (en, 2012) |
| CA (1) | CA2162846A1 (en, 2012) |
| CZ (1) | CZ291264B6 (en, 2012) |
| DE (1) | DE69428533T2 (en, 2012) |
| DK (1) | DK0698013T3 (en, 2012) |
| ES (1) | ES2163445T3 (en, 2012) |
| FR (1) | FR09C0038I2 (en, 2012) |
| GR (1) | GR3036942T3 (en, 2012) |
| HU (1) | HU218381B (en, 2012) |
| LV (1) | LV11464B (en, 2012) |
| NZ (1) | NZ267222A (en, 2012) |
| PL (1) | PL174704B1 (en, 2012) |
| PT (1) | PT698013E (en, 2012) |
| RU (1) | RU2139862C1 (en, 2012) |
| SI (1) | SI9420029A (en, 2012) |
| SK (1) | SK140295A3 (en, 2012) |
| WO (1) | WO1994026722A1 (en, 2012) |
Families Citing this family (77)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SK140295A3 (en) * | 1993-05-12 | 1996-09-04 | Du Pont | Condensed bicyclic pyrimidinones, fungicidal agents on their base and inhibition method of plant deseases by using them |
| USH1829H (en) * | 1994-11-02 | 2000-01-04 | E. I. Du Pont De Nemours And Company | Fungicidal fused bicyclic pyrimidinones |
| WO1996020178A1 (en) * | 1994-12-27 | 1996-07-04 | Warner-Lambert Company | Novel heterocycles as cholecystokinin (cck) ligands |
| EP0836602B1 (en) * | 1995-07-05 | 2002-01-30 | E.I. Du Pont De Nemours And Company | Fungicidal pyrimidinones |
| US6897213B1 (en) | 1995-11-21 | 2005-05-24 | Warner-Lambert Company | Heterocycles as cholecystokinin (CCK) ligands |
| CZ288498A3 (cs) | 1996-03-11 | 1998-12-16 | Novartis Ag | Deriváty pyrimidin-4-onu jako pesticidní látky, způsob jejich přípravy a agrochemické prostředky, které je obsahují |
| EP1344775B1 (en) * | 1996-06-18 | 2006-11-29 | E.I. Du Pont De Nemours And Company | Preparation of fungicidal quinazolinones and useful intermediates |
| TW434228B (en) * | 1996-06-18 | 2001-05-16 | Du Pont | Preparation of fungicidal quinazolinones and useful intermediates |
| BR9714222A (pt) * | 1996-12-17 | 2000-04-18 | Du Pont | Método para o controle de doenças de plantas |
| EP1310169A3 (en) * | 1997-01-30 | 2003-08-27 | E.I. Du Pont De Nemours And Company | Fungicidal mixture |
| ZA9711323B (en) * | 1997-01-30 | 1999-06-17 | I E Du Pont De Nemours And Com | Fungicidal mixtures |
| WO1998040363A1 (de) * | 1997-03-07 | 1998-09-17 | Lonza Ag | Verfahren zur herstellung von chinazol-4-onen |
| GB9718737D0 (en) | 1997-09-04 | 1997-11-12 | Ciba Geigy Ag | Pesticide |
| GB9719411D0 (en) * | 1997-09-12 | 1997-11-12 | Ciba Geigy Ag | New Pesticides |
| EP1035774A1 (en) * | 1997-12-01 | 2000-09-20 | Novartis AG | Fungicidal combinations comprising quinazolinone |
| US6255311B1 (en) * | 1998-01-14 | 2001-07-03 | E. I. Du Pont De Nemours And Company | Fungicidal fused bicyclic pyrimidinones |
| GB9802355D0 (en) | 1998-02-04 | 1998-04-01 | Ciba Geigy Ag | Organic compounds |
| WO1999067202A1 (en) * | 1998-06-19 | 1999-12-29 | Syngenta Participations Ag . | Process for preparation of pyrimidinone derivatives |
| US6337332B1 (en) * | 1998-09-17 | 2002-01-08 | Pfizer Inc. | Neuropeptide Y receptor antagonists |
| GB9827162D0 (en) * | 1998-12-10 | 1999-02-03 | Novartis Ag | Organic compounds |
| WO2000051992A1 (en) * | 1999-03-04 | 2000-09-08 | E.I. Du Pont De Nemours And Company | Fused bicyclic oxazinone and thiazinone fungicides |
| CO5170526A1 (es) * | 1999-05-28 | 2002-06-27 | Smithkline Beecham Corp | Nuevos compuestos de guanidina ciclica utiles como antagonis tas del receptor de la il-8 |
| DE60121695T2 (de) | 2000-02-22 | 2007-08-30 | Daiichi Asubio Pharma Co., Ltd. | Arzneimittel mit chymaseinhibitoren als wirksames mittel zur behandlung von dermatitis mit zweiphasigen hautreaktionen |
| CN1245978C (zh) | 2000-02-22 | 2006-03-22 | 第一阿斯比奥制药株式会社 | 含有胃促胰酶抑制剂作为活性成分的预防和治疗各种与嗜酸性粒细胞增多有关的疾病的药物 |
| US20040033555A1 (en) * | 2001-07-20 | 2004-02-19 | Shawn Louise Anderson | Methods using light emission for determining the effeciveness of plant treatment agents in controlling plant disease organisms |
| TW200306155A (en) | 2002-03-19 | 2003-11-16 | Du Pont | Benzamides and advantageous compositions thereof for use as fungicides |
| KR100967280B1 (ko) * | 2002-06-11 | 2010-07-01 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 흰가루병을 방제하는데 유용한 융합된 피리미디논과디니트로페놀 화합물의 혼합물 |
| ES2274242T3 (es) * | 2002-06-11 | 2007-05-16 | E.I. Du Pont De Nemours And Company | Mezclas de pirimidinonas combinadas y compuestos dinitrofenolicos utiles para controlar el moho. |
| EP1407774A1 (en) * | 2002-09-10 | 2004-04-14 | LION Bioscience AG | 2-Amino-4-quinazolinones as LXR nuclear receptor binding compounds |
| AU2003278066A1 (en) * | 2002-10-28 | 2004-05-25 | Basf Aktiengesellschaft | Fungicide mixtures containing oxazinone |
| GB0227555D0 (en) * | 2002-11-26 | 2002-12-31 | Syngenta Ltd | Fungicides |
| DE60335028D1 (de) * | 2002-12-23 | 2010-12-30 | Icagen Inc | Quinazolinone als kaliumkanalmodulatoren |
| RU2275362C2 (ru) * | 2004-05-14 | 2006-04-27 | Петр Сергеевич Хохлов | 3-гидрокси-2-тиоксо-4(3н)-хиназолинон, обладающий фунгицидными и росторегулирующими свойствами, и способ его получения |
| GB0418047D0 (en) | 2004-08-12 | 2004-09-15 | Syngenta Participations Ag | Fungicidal compositions |
| GB0422401D0 (en) | 2004-10-08 | 2004-11-10 | Syngenta Participations Ag | Fungicidal compositions |
| GB0426373D0 (en) * | 2004-12-01 | 2005-01-05 | Syngenta Ltd | Fungicides |
| AR053563A1 (es) * | 2005-03-21 | 2007-05-09 | Basf Ag | Mezclas insecticidas |
| DE102005015677A1 (de) | 2005-04-06 | 2006-10-12 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| KR20080018943A (ko) | 2005-06-09 | 2008-02-28 | 바이엘 크롭사이언스 아게 | 활성 물질 배합물 |
| DE102005026482A1 (de) | 2005-06-09 | 2006-12-14 | Bayer Cropscience Ag | Wirkstoffkombinationen |
| DE102006023263A1 (de) * | 2006-05-18 | 2007-11-22 | Bayer Cropscience Ag | Synergistische Wirkstoffkombinationen |
| WO2008013622A2 (en) | 2006-07-27 | 2008-01-31 | E. I. Du Pont De Nemours And Company | Fungicidal azocyclic amides |
| CL2007003256A1 (es) * | 2006-11-15 | 2008-07-25 | Du Pont | Mezcla fungicida que comprende al menos tres compuestos diferentes; composicion fungicida que comprende dicha mezcla; y metodo para controlar una enfermedad en plantas causada por el patogeno fungico vegetal que comprende aplicar una cantidad de la m |
| CN101622245B (zh) | 2007-01-25 | 2014-09-10 | 纳幕尔杜邦公司 | 杀真菌酰胺 |
| US20080200461A1 (en) * | 2007-02-20 | 2008-08-21 | Cropsolution, Inc. | Modulators of acetyl-coenzyme a carboxylase and methods of use thereof |
| DE102007045920B4 (de) | 2007-09-26 | 2018-07-05 | Bayer Intellectual Property Gmbh | Synergistische Wirkstoffkombinationen |
| BRPI0905759A2 (pt) | 2008-01-25 | 2015-07-14 | Du Pont | Composto selecionado a partir dos compostos de fórmula 1 e n óxidos e sais dos mesmos, método para controlar doenças de planta causadas por patógenos de planta fúngicos oomycota e composição fungicida |
| EP2358709B1 (en) | 2008-12-02 | 2014-01-22 | E. I. du Pont de Nemours and Company | Fungicidal heterocyclic compounds |
| EP2430179A4 (en) * | 2009-02-27 | 2014-01-08 | Syngenta Participations Ag | DETECTION METHOD |
| AR075713A1 (es) | 2009-03-03 | 2011-04-20 | Du Pont | Pirazoles fungicidas |
| UA104887C2 (uk) | 2009-03-25 | 2014-03-25 | Баєр Кропсаєнс Аг | Синергічні комбінації активних речовин |
| CN102510721B (zh) | 2009-07-16 | 2014-11-19 | 拜尔农作物科学股份公司 | 含苯基三唑的协同活性物质结合物 |
| BR112012002765A2 (pt) | 2009-08-07 | 2017-06-13 | Du Pont | composto, composição-fungicida e método de controle de doenças das plantas causadas por patógenos vegetais fúngicos |
| JP6267863B2 (ja) * | 2009-10-16 | 2018-01-24 | メリンタ セラピューティクス，インコーポレイテッド | 抗微生物性化合物および抗微生物性化合物の製造方法および使用方法 |
| SG10201406634VA (en) * | 2009-10-16 | 2014-11-27 | Melinta Therapeutics Inc | Antimicrobial compounds and methods of making and using the same |
| PH12012500734A1 (en) | 2009-10-16 | 2012-11-26 | Melinta Therapeutics Inc | Antimicrobial compounds and methods of making and using the same |
| EA023350B1 (ru) | 2009-10-16 | 2016-05-31 | Мелинта Терапьютикс, Инк. | Противомикробные соединения, способы их получения и применение |
| TW201116212A (en) | 2009-10-29 | 2011-05-16 | Du Pont | Heterobicycle-substituted azolyl benzene fungicides |
| WO2011051958A1 (en) | 2009-10-30 | 2011-05-05 | E.I. Du Pont De Nemours And Company | Fungicidal pyrazolones |
| RU2562527C9 (ru) | 2009-12-16 | 2016-07-10 | Байер Интеллектуэль Проперти Гмбх | Комбинации активных веществ, содержащие проквиназид, биксафен и/или протиоконазол |
| KR20120112755A (ko) | 2010-01-07 | 2012-10-11 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 살진균제 복소환 화합물 |
| WO2012023143A1 (en) | 2010-08-19 | 2012-02-23 | E. I. Du Pont De Nemours And Company | Fungicidal pyrazoles |
| RU2013114710A (ru) | 2010-09-03 | 2014-10-10 | Байер Интеллектуэль Проперти Гмбх | Замещенные конденсированные пиримидиноны и дигидропиримидиноны |
| CN103827118B (zh) * | 2011-07-27 | 2016-03-09 | 葛兰素集团有限公司 | 双环嘧啶酮化合物 |
| CN103554038B (zh) * | 2013-06-19 | 2015-10-14 | 云南大学 | 多卤代苯腈喹唑啉酮化合物及其制备方法和用途 |
| US9937183B2 (en) | 2013-09-09 | 2018-04-10 | Melinta Therapeutics, Inc. | Antimicrobial compounds and methods of making and using the same |
| CN106103442A (zh) | 2013-09-09 | 2016-11-09 | 梅琳塔治疗公司 | 抗微生物化合物及制备和使用其的方法 |
| WO2015189113A1 (en) | 2014-06-11 | 2015-12-17 | Bayer Cropscience Aktiengesellschaft | Active compound combinations comprising proquinazid and spiroxamine and optionally prothioconazole |
| HK1249758A1 (zh) | 2015-03-11 | 2018-11-09 | Melinta Therapeutics, Inc. | 抗微生物化合物及其制备和使用方法 |
| EP2910126A1 (en) | 2015-05-05 | 2015-08-26 | Bayer CropScience AG | Active compound combinations having insecticidal properties |
| CA3023317A1 (en) | 2016-05-06 | 2017-11-09 | Melinta Therapeutics, Inc. | Antimicrobials and methods of making and using same |
| ES2968172T3 (es) | 2016-10-24 | 2024-05-08 | Fmc Corp | Oxadiazoles que tienen actividad fungicida |
| CN106417303A (zh) * | 2016-12-05 | 2017-02-22 | 湖南泽丰农化有限公司 | 一种含有丙氧喹啉的高效杀菌组合物 |
| CN108358856B (zh) * | 2018-01-08 | 2019-09-13 | 牡丹江医学院 | 一种防治消化性溃疡的药物以及其制备方法和用途 |
| CN109748910B (zh) * | 2018-12-17 | 2021-04-30 | 徐州医科大学 | 一种喹唑啉酮类化合物、其制备方法及医药用途 |
| CN110950863B (zh) * | 2019-11-15 | 2021-04-02 | 中山大学 | 一种喹唑啉酮类化合物及其制备方法和应用 |
| EP4311829A1 (en) | 2022-07-28 | 2024-01-31 | Nodus Oncology Limited | Substituted bicyclic heteroaryl sulfonamide derivatives for the treatment of cancer |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE210452C (en, 2012) * | ||||
| DE253622C (en, 2012) * | ||||
| US3560619A (en) * | 1967-01-03 | 1971-02-02 | Mead Johnson & Co | Aminoquinazolines and quinazolones in treatment of coccidiosis |
| DE1962605C2 (de) * | 1969-12-13 | 1983-09-08 | Agfa-Gevaert Ag, 5090 Leverkusen | Photographisches Aufzeichnungsmaterial |
| US3755582A (en) * | 1971-03-04 | 1973-08-28 | Du Pont | Quinazolinone fungicides |
| US3714354A (en) * | 1971-07-06 | 1973-01-30 | Pfizer | Bronchodilator activity of substituted quinazolinecarboxylic acid esters |
| US3775582A (en) * | 1971-12-09 | 1973-11-27 | North American Rockwell | Proximity control using microwave techniques |
| DE2218301A1 (de) * | 1972-04-15 | 1973-10-25 | Bayer Ag | Verfahren zur herstellung von 2trifluormethylimino-derivaten von sechsring-heterocyclen |
| US3867384A (en) * | 1972-09-01 | 1975-02-18 | Greg A Bullock | 2-Amino-4(3H)-quinazolinones |
| US3784693A (en) * | 1972-10-18 | 1974-01-08 | Sandoz Ag | 3-substituted phenyl-quinazoline-4(3h)-ones as sedative hypnotics |
| NZ192392A (en) * | 1978-12-19 | 1983-02-15 | M Ishikawa | 3-(substituted (phenyl or pyridyl)) -3,4-dihydroquinazolin-4-ones |
| DE3228871A1 (de) * | 1982-08-03 | 1984-02-09 | Bayer Ag, 5090 Leverkusen | Oxochinazolin-carbaminsaeureester |
| SU1325048A1 (ru) * | 1986-02-11 | 1987-07-23 | Ташкентский государственный медицинский институт | 3-Метил-2 @ -метилакрилоиламидо @ хиназолон-4 как термо- и светостабилизатор поливинилхлорида |
| JPH0749423B2 (ja) * | 1987-01-30 | 1995-05-31 | 日清製粉株式会社 | ２−アルキルスルフイニル−４（３ｈ）−キナゾリノン誘導体、その製造方法およびそれを有効成分とする抗潰瘍薬 |
| JPH07107056B2 (ja) * | 1987-01-30 | 1995-11-15 | 日清製粉株式会社 | ４（３ｈ）−キナゾリノン誘導体、その製造方法およびそれを有効成分とする抗潰瘍剤 |
| YU47288B (sh) * | 1987-07-11 | 1995-01-31 | Schering Agrochemicals Limited | Akrilatni fungicidi i postupak za njihovo dobijanje |
| DD287033A5 (de) * | 1989-08-17 | 1991-02-14 | Akademie Der Wissenschaften Der Ddr,De | Verfahren zur herstellung von 2-alkoxy-4-oxo-chinazolin-3-yl-alkansaeuren |
| US5276038A (en) * | 1992-06-01 | 1994-01-04 | American Cyanamid Company | 1-aryl-3-(3,4-dihydro-4-oxo-3-quinazolinyl)urea fungicidal agents |
| SK140295A3 (en) * | 1993-05-12 | 1996-09-04 | Du Pont | Condensed bicyclic pyrimidinones, fungicidal agents on their base and inhibition method of plant deseases by using them |
-
1994
- 1994-05-10 SK SK1402-95A patent/SK140295A3/sk unknown
- 1994-05-10 HU HU9503173A patent/HU218381B/hu active Protection Beyond IP Right Term
- 1994-05-10 AU AU69443/94A patent/AU6944394A/en not_active Abandoned
- 1994-05-10 EP EP94917917A patent/EP0698013B1/en not_active Expired - Lifetime
- 1994-05-10 CN CN94192068A patent/CN1050355C/zh not_active Expired - Lifetime
- 1994-05-10 DE DE69428533T patent/DE69428533T2/de not_active Expired - Lifetime
- 1994-05-10 PT PT94917917T patent/PT698013E/pt unknown
- 1994-05-10 CA CA002162846A patent/CA2162846A1/en not_active Abandoned
- 1994-05-10 JP JP6525540A patent/JPH08510243A/ja active Pending
- 1994-05-10 ES ES94917917T patent/ES2163445T3/es not_active Expired - Lifetime
- 1994-05-10 CZ CZ19952803A patent/CZ291264B6/cs not_active IP Right Cessation
- 1994-05-10 BR BR9406662A patent/BR9406662A/pt not_active Application Discontinuation
- 1994-05-10 PL PL94311641A patent/PL174704B1/pl unknown
- 1994-05-10 RU RU95121800A patent/RU2139862C1/ru active Protection Beyond IP Right Term
- 1994-05-10 AT AT94917917T patent/ATE206406T1/de active
- 1994-05-10 WO PCT/US1994/004965 patent/WO1994026722A1/en active IP Right Grant
- 1994-05-10 US US08/545,827 patent/US5747497A/en not_active Expired - Lifetime
- 1994-05-10 DK DK94917917T patent/DK0698013T3/da active
- 1994-05-10 SI SI9420029A patent/SI9420029A/sl unknown
- 1994-05-10 NZ NZ267222A patent/NZ267222A/en not_active IP Right Cessation
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1995
- 1995-11-10 LV LVP-95-339A patent/LV11464B/en unknown
-
1998
- 1998-01-14 US US09/007,336 patent/US5945423A/en not_active Expired - Lifetime
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2001
- 2001-10-18 GR GR20010401811T patent/GR3036942T3/el unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| CN1050355C (zh) | 2000-03-15 |
| BR9406662A (pt) | 1996-02-06 |
| CA2162846A1 (en) | 1994-11-24 |
| PL174704B1 (pl) | 1998-09-30 |
| LV11464A (lv) | 1996-08-20 |
| HU9503173D0 (en) | 1995-12-28 |
| DE69428533D1 (de) | 2001-11-08 |
| US5747497A (en) | 1998-05-05 |
| JPH08510243A (ja) | 1996-10-29 |
| NZ267222A (en) | 1996-10-28 |
| HU218381B (hu) | 2000-08-28 |
| HUT72829A (en) | 1996-05-28 |
| ES2163445T3 (es) | 2002-02-01 |
| CN1123028A (zh) | 1996-05-22 |
| AU6944394A (en) | 1994-12-12 |
| WO1994026722A1 (en) | 1994-11-24 |
| FR09C0038I2 (en, 2012) | 2010-06-11 |
| DK0698013T3 (da) | 2001-12-10 |
| RU2139862C1 (ru) | 1999-10-20 |
| PT698013E (pt) | 2002-01-30 |
| FR09C0038I1 (en, 2012) | 2009-09-25 |
| LV11464B (en) | 1997-02-20 |
| ATE206406T1 (de) | 2001-10-15 |
| CZ280395A3 (en) | 1996-03-13 |
| EP0698013B1 (en) | 2001-10-04 |
| PL311641A1 (en) | 1996-03-04 |
| SK140295A3 (en) | 1996-09-04 |
| EP0698013A1 (en) | 1996-02-28 |
| SI9420029A (en) | 1996-10-31 |
| US5945423A (en) | 1999-08-31 |
| GR3036942T3 (en) | 2002-01-31 |
| DE69428533T2 (de) | 2002-05-23 |
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