SI9420029A - Fungicidal fused bicyclic pyrimidinones - Google Patents
Fungicidal fused bicyclic pyrimidinones Download PDFInfo
- Publication number
- SI9420029A SI9420029A SI9420029A SI9420029A SI9420029A SI 9420029 A SI9420029 A SI 9420029A SI 9420029 A SI9420029 A SI 9420029A SI 9420029 A SI9420029 A SI 9420029A SI 9420029 A SI9420029 A SI 9420029A
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- SI
- Slovenia
- Prior art keywords
- alkyl
- optionally substituted
- haloalkyl
- cycloalkyl
- haloalkenyl
- Prior art date
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- -1 bicyclic pyrimidinones Chemical class 0.000 title claims description 127
- 230000000855 fungicidal effect Effects 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 124
- 239000000203 mixture Substances 0.000 claims abstract description 34
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 112
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 86
- 125000001188 haloalkyl group Chemical group 0.000 claims description 85
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 77
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 70
- 125000003342 alkenyl group Chemical group 0.000 claims description 68
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 58
- 125000000304 alkynyl group Chemical group 0.000 claims description 58
- 229910052736 halogen Inorganic materials 0.000 claims description 53
- 150000002367 halogens Chemical group 0.000 claims description 52
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 43
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 41
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 40
- 125000005452 alkenyloxyalkyl group Chemical group 0.000 claims description 37
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 125000001544 thienyl group Chemical group 0.000 claims description 29
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 26
- 125000004414 alkyl thio group Chemical group 0.000 claims description 26
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 25
- 125000004001 thioalkyl group Chemical group 0.000 claims description 25
- 125000005082 alkoxyalkenyl group Chemical group 0.000 claims description 23
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 125000002541 furyl group Chemical group 0.000 claims description 22
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 20
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 19
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 17
- 125000001624 naphthyl group Chemical group 0.000 claims description 17
- 125000004076 pyridyl group Chemical group 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 16
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 13
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 13
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 13
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 12
- 229910052740 iodine Inorganic materials 0.000 claims description 12
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 12
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 11
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 239000011630 iodine Substances 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 7
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 125000005108 alkenylthio group Chemical group 0.000 claims description 6
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 claims description 6
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 5
- 125000005109 alkynylthio group Chemical group 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
- 125000006226 butoxyethyl group Chemical group 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- FVQAEZOUDXAZGN-UHFFFAOYSA-N 6-bromo-2-propoxy-3-propylquinazolin-4-one Chemical compound C1=C(Br)C=C2C(=O)N(CCC)C(OCCC)=NC2=C1 FVQAEZOUDXAZGN-UHFFFAOYSA-N 0.000 claims description 3
- 241000221785 Erysiphales Species 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 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 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 2
- 244000000004 fungal plant pathogen Species 0.000 claims 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims 1
- CGVCBPKQFKNLDR-UHFFFAOYSA-N 6-bromo-3-(cyclopropylmethyl)-2-propoxyquinazolin-4-one Chemical group CCCOC1=NC2=CC=C(Br)C=C2C(=O)N1CC1CC1 CGVCBPKQFKNLDR-UHFFFAOYSA-N 0.000 claims 1
- 125000004650 C1-C8 alkynyl group Chemical group 0.000 claims 1
- 239000000417 fungicide Substances 0.000 abstract description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 714
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 140
- 101150065749 Churc1 gene Proteins 0.000 description 31
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 25
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 239000003921 oil Substances 0.000 description 21
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 18
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 18
- 241000196324 Embryophyta Species 0.000 description 17
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 16
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 12
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 102100038239 Protein Churchill Human genes 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 8
- 125000000484 butyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
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- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 6
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- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 5
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- 238000003889 chemical engineering Methods 0.000 description 1
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- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 1
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- 238000005187 foaming Methods 0.000 description 1
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- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 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
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- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
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- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 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
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- 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
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
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- 239000002023 wood Substances 0.000 description 1
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 (1)
| Publication Number | Publication Date |
|---|---|
| SI9420029A true SI9420029A (en) | 1996-10-31 |
Family
ID=26740142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9420029A SI9420029A (en) | 1993-05-12 | 1994-05-10 | Fungicidal fused bicyclic pyrimidinones |
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) |
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| 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 |
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| 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
-
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
-
2001
- 2001-10-18 GR GR20010401811T patent/GR3036942T3/el unknown
-
2009
- 2009-08-14 FR FR09C0038C patent/FR09C0038I2/fr active Active
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 |
| CZ291264B6 (cs) | 2003-01-15 |
| 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 |
| US5945423A (en) | 1999-08-31 |
| GR3036942T3 (en) | 2002-01-31 |
| DE69428533T2 (de) | 2002-05-23 |
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