KR930000480A - 치환된 1h-3-아릴-피롤리딘-2,4-디온 유도체 - Google Patents
치환된 1h-3-아릴-피롤리딘-2,4-디온 유도체 Download PDFInfo
- Publication number
- KR930000480A KR930000480A KR1019920011297A KR920011297A KR930000480A KR 930000480 A KR930000480 A KR 930000480A KR 1019920011297 A KR1019920011297 A KR 1019920011297A KR 920011297 A KR920011297 A KR 920011297A KR 930000480 A KR930000480 A KR 930000480A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- alkoxy
- halogen
- substituted
- optionally
- Prior art date
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- 229910052736 halogen Inorganic materials 0.000 claims 45
- 150000002367 halogens Chemical group 0.000 claims 45
- 125000000217 alkyl group Chemical group 0.000 claims 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 23
- 229910052760 oxygen Inorganic materials 0.000 claims 23
- 239000001301 oxygen Substances 0.000 claims 23
- 125000003545 alkoxy group Chemical group 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- 239000001257 hydrogen Substances 0.000 claims 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 15
- 229910052801 chlorine Inorganic materials 0.000 claims 15
- 239000000460 chlorine Substances 0.000 claims 15
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 15
- 229910052731 fluorine Inorganic materials 0.000 claims 14
- 239000011737 fluorine Substances 0.000 claims 14
- -1 alkenyl radical Chemical class 0.000 claims 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 13
- 229910052794 bromium Inorganic materials 0.000 claims 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 11
- 239000011593 sulfur Substances 0.000 claims 11
- 125000001188 haloalkyl group Chemical group 0.000 claims 9
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 7
- 239000003085 diluting agent Substances 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 150000001721 carbon Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 5
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- 239000011230 binding agent Substances 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- 241000238876 Acari Species 0.000 claims 3
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims 3
- 241000196324 Embryophyta Species 0.000 claims 3
- 241000238631 Hexapoda Species 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 230000000895 acaricidal effect Effects 0.000 claims 2
- 239000000642 acaricide Substances 0.000 claims 2
- 125000005108 alkenylthio group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000005109 alkynylthio group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 239000004009 herbicide Substances 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 239000002917 insecticide Substances 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000004999 nitroaryl group Chemical group 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims 1
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical compound [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 claims 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 230000000903 blocking effect Effects 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- NBYQXBYMEUOBON-UHFFFAOYSA-N carbamothioyl chloride Chemical compound NC(Cl)=S NBYQXBYMEUOBON-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000002085 enols Chemical class 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Chemical group CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Chemical group C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 150000003852 triazoles Chemical group 0.000 claims 1
- SMBZJSVIKJMSFP-UHFFFAOYSA-N trifluoromethyl hypofluorite Chemical compound FOC(F)(F)F SMBZJSVIKJMSFP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/36—Oxygen or sulfur atoms
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
- A01N57/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34 containing aromatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/38—2-Pyrrolones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/54—Spiro-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
- C07F9/5728—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
Abstract
내용 없음
Description
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Claims (10)
- 일반식(I)의 치환된 3-아릴-피롤리딘-2,4-디온 유도체 및 일반식(I)의 화합물의 순수한 거울상 이성체 형태.상기 식에서, X는 알킬, 할로겐 또는 알콕시를 나타내고, Y는 수소, 알킬, 할로겐, 알콕시 또는 할로게노알킬을 나타내며, Z는 알킬, 할로겐 또는 알콕시를 나타내고, n은 0 내지 3의 숫자를 나타내며, A는 수소를 나타내거나, 또는 각각 임의로 할로겐으로 치환된 알킬, 알콕시알킬 또는 알킬티오알킬, 헤테로원자로 임의로 차단된 시클로알킬을 나타내거나, 또는 각각 할로겐, 알킬, 할로게노알킬, 알콕시 또는 니트로로 임의로 치환된 아릴, 아릴알킬 또는 헤트아릴을 나타내고, B는 수소, 알킬 또는 알콕시알킬을 나타내거나, 또는 A 및 B는 이들이 결합된 탄소원자와 함께, 임의로 치환된, 산소 및/또는 황으로 차단될 수 있는 포화 또는 불포화환을 형성하며, R은 일반식 (a), (b), (c) 또는 (d)로 표시되는 그룹을 나타내고,상기 식에서, L 및 M은 산소 또는 황을 나타내고, 단 L 및 M은 동시에 산소를 나타내지 않으며, R1, R2및 R3는 독립적으로 각각 임의로 할로겐 치환된 알킬, 알콕시, 알킬아미노, 디알킬아미노, 알킬티오, 알케닐티오, 알키닐티오 및 시클로알킬티오를 나타내고, 또한 각각 임의로 치환된 페닐, 벤질, 페녹시 또는 페닐티오를 나타내고, R4및 R5는 독립적으로 각각 수소를 나타내거나, 또는 각각 임의로 할로겐으로 치환된 알킬, 알케닐, 알콕시 또는 알콕시알킬을 나타내거나, 또는 임의로 치환된 페닐 또는 임의로 치환된 벤질을 나타내거나, 또는 R4및 R5는 함꼐 임의로 산소원자로 차단된 알케닐 라디칼을 나타내며, R6는 임의로 할로겐으로 치환되고, 산소로 차단될 수 있는 알킬을 나타내거나, 또는 임의로 할로겐, 할로게노알킬 또는 알콕시로 치환된 페닐을 나타내거나, 또는 임의로 할로겐, 할로게노느알킬, 알킬 및 알콕시로 치환된 벤질을 나타내거나, 또는 알케닐 또는 알키닐을 나타낸다.
- 일반식(Ia) 내지 (Id)의 치환된 3-아릴-피롤리딘-2,4-디은-유도체.상기 식에서, A, B, L, M, X, Y, Zn, R1, R2, R3, R4, R5및 R6는 특허청구범위 제1항에서 주어진 의미를 가진다.
- 제1항에 있어서, X가 C1-C6-알킬, 할로겐 또는 C1-C6-알콕시를 나타내고, Y가 수소, C1-C6-알킬, 할로겐 C1-C6-알콕시 또는 C1-C3-할로게노알킬을 나타내며, Z가 C1-C6-알킬, 할로겐 또는 C1-C6-알콕시를 나타내고, n이 0 내지 3의 숫자를 나타내며, A가 수소 또는 각각 임의로 할로겐으로 치환된, 각각 직쇄 또는 측쇄의 C1-C12-알킬, C3-C8-알케닐, C3-C8-알키닐, C1-C10-알콕시-C2-C8-알킬, C1-C8-폴리알콕시-C2-C8-알킬 및 C1-C10-알킬티오-C2-C8-알킬을 나타내거나, 또는 3 내지 8개의 환원자를 가지며, 산소 및/또는 황으로 차단될 수 있는 시클로 알킬을 나타내거나, 또는 각각 임의로 할로겐, C1-C6-알킬, C1-C6-할로알킬, C1-C6-알콕시 또는 니트로로 치환된 아릴, 헤트아릴 또는 아릴-C1-C6-알킬을 나타내고, B가 수소 또는 직쇄 또는 측쇄의 C1-C12-알킬 또는 C1-C8-알콕시알킬을 나타내거나, 또는 A 및 B가 이들이 결합된 탄소원자와 함께, 각각 임의로 할로겐화된 알킬, 알콕시 또는 페닐 및 할로겐으로 치환될 수 있고, 산소 및/또는 황으로 차단될 수 있는 3- 내지 8-원의 포화 또는 불포화환을 형성하며, R이 일반식 (a), (b), (c) 또는 (d)로 표시되는 그룹을 나타내고,L 및 M은 각각 산소 또는 황을 나타내고, 단 L 및 M은 동시에 산소를 나타내지 않으며, R1, R2및 R3가 개개 독립적으로 각각 임의로 할로겐 치환된 C1-C8-알킬, C1-C8-알콕시, C1-C8-알킬아미노, 디-(C1-C8)-알킬아미노, C1-C8-알킬티오, C2-C5-알케닐티오, C2-C5-알키닐티오 및 C3-C7-시클로알킬티오를 나타내거나, 또는 각각 임의로 할로겐, 니트로, 시아노, C1-C4-알콕시, C1-C4-할로게노알콕시, C1-C4-알킬티오, C1-C4-알로게노 알킬티오, C1-C4-알킬 또는 C1-C4-할로게노알킬로 치환된 페닐, 벤질, 페녹시 또는 페닐티오를 나타내고, R4및 R5가 개개 독립적으로 각각 임의로 할로겐 치환된 C1-C20-알킬, C1-C20-알콕시, C2-C8-알케닐 또는 C1-C20-알콕시-C1-C20-알킬을 나타내거나, 또는 임의로 할로겐, C1-C20-할로게노알킬, C1-C20-알킬 또는 C1-C20-알콕시로 치환된 페닐을 나타내거나, 또는 임의로 할로겐, C1-C20-알킬, C1-C20-할로게노알킬 또는 C1-C20-알콕시로 치환된 벤질을 나타내거나, 또는 R4및 R5가 함께 임의로 산소원자로 차단된 C2-C8-알킬렌환을 나타내며, R6가 임의로 할로겐으로 치환되고, 산소로 차단될 수 있는 C1-C20-알킬을 나타내거나, 또는 임의로 할로겐, C1-C20-할로게노알킬 또는 C1-C20-알콕시로 치환된 페닐을 나타내거나, 임의로 할로겐, C1-C20-할로게노알킬 또는 C1-C20-알콕시로 치환된 벤질을 나타내거나, 또는 C2-C8-알케닐 또는 C2-C5-알키닐을 나타내는 일반식(I)의 치환된 3-아릴-피롤리딘-2,4-디온유도체 및 일반식(I)의 화합물의 순수한 거울상 이성체 형태.
- 제1항에 있어서, X가 C1-C6-알킬, 할로겐 또는 C1-C6-알콕시를 나타내고, Y가 수소, C1-C6-알킬, 할로겐 C1-C4-알콕시 또는 C1-C2-할로게노알킬을 나타내며, Z가 C1-C4-알킬, 할로겐 또는 C1-C4-알콕시를 나타내고, n이 0 내지 3의 숫자를 나타내며, A가 수소 또는 각각 임의로 할로겐으로 치환된, 각각 직쇄 또는 측쇄의 C1-C20-알킬, C3-C8-알케닐, C3-C8-알키닐, C1-C8-알콕시-C2-C8-알킬, C1-C8-폴리알콕시-C2-C8-알킬 및 C1-C8-알킬티오-C2-C8-알킬을 나타내거나, 또는 3 내지 7개의 환원자로 가지며, 1내지 2개의 산소 및/또는 황원자로 차단될 수 있는 시클로 알킬을 나타내거나, 또는 각각 임의로 할로겐, C1-C4-알킬, C1-C4-할로알킬, C1-C4-알콕시 또는 니트로로 치환된 아릴, 헤트아릴 또는 아릴-C1-C4-알킬을 나타내고, B가 수소 또는 직쇄 또는 측쇄의 C1-C10-알킬 또는 C1-C6-알콕시알킬을 나타내거나, 또는 A 및 B가 이들이 결합된 탄소원자와 함께, C1-C6-알킬, C1-C6-알콕시, C1-C3-할로알콕시, 불소, 염소 및 치환된 페닐로 치환될 수 있고, 산소 및/또는 황으로 차단될 수 있는 3- 내지 7-원의 포화 또는 불포화환을 형성하며, R이 일반식 (a), (b), (c) 또는 (d)로 표시되는 그룹을 나타내고,상기식에서 L 및 M은 각각 산소 또는 황을 나타내고, 단 L 및 M은 동시에 산소를 나타내지 않으며, R1, R2및 R3가 개개 독립적으로 각각 임의로 할로겐 치환된 C1-C6-알킬, C1-C6-알콕시, C1-C6-알킬아미노, 디-(C1-C8)-알킬아미노, C1-C8-알킬티오, C3-C4-알케닐티오, C3-C4-알키닐티오 및 C3-C6-시클로알킬티오를 나타내거나, 또는 각각 임의로 불소, 염소, 브롬, 니트로, 시아노, C1-C3-알콕시, C1-C3-알로게노알콕시, C1-C3-알킬티오, C1-C3-알로게노 알킬티오, C1-C3-알킬 또는 C1-C3-할로게노알킬로 치환된 페닐, 벤질, 페녹시 또는 페닐티오를 나타내고, R4및 R5가 개개 독립적으로 각각 임의로 할로겐 치환된 C1-C20-알킬, C1-C20-알콕시, C2-C8-알케닐 또는 C1-C20-알콕시-C1-C20-알킬을 나타내거나, 또는 임의로 할로겐, C1-C5-알로게노알킬, C1-C5-알킬 또는 C1-C5-알콕시로 치환된 페닐을 나타내거나, 또는 임의로 할로겐, C1-C5-알킬, C1-C5-할로게노알킬 또는 C1-C5-알콕시로 치환된 벤질을 나타내거나, 또는 R6가 임의로 할로겐으로 치환되고, 산소로 차단될 수 있는 C1-C20-알킬을 나타내거나, 또는 임의로 할로겐, C1-C5-할로게노알킬 또는 C1-C5-알콕시로 치환된 페닐을 나타내거나, 임의로 할로겐, C1-C5-할로게노알킬 또는 C1-C5-알콕시로 치환된 벤질을 나타내는, 일반식(I)의 치환된 3-아릴-피롤리딘-2,4-디온유도체 및 일반식(I)의 화합물의 순수한 거울상 이성체 형태.
- 제1항에 있어서, X가 메틸, 에틸, 프로필, i-프로필, 불소, 염소, 브롬, 메톡시 및 에톡시를 나타내고, Y가 수소, 메틸, 에틸, i-프로필, 부틸, i-부틸, 3급-부틸, 불소, 염소, 브롬, 메톡시, 에톡시 및 트리플루오로 메틸을 나타내고, Z가 메틸, 에틸, i-프로필, 부틸, i-부틸, 3급-부틸, 불소, 염소, 브롬, 메톡시 및 에톡시를 나타내고, n이 0 내지 3의 숫자를 나타내고, A가 수소를 나타내거나, 또는 각각의 경우에서 각각 임의로 할로겐으로 치환된, 각각 직쇄 또는 측쇄의 C1-C8-알킬, C3-C4-알케닐, C3-C4-알키닐, C1-C6-알콕시-C2-C4-알킬, C1-C4-폴리옥콕시-C2-C4-알킬 및 C1-C6-알킬티오-C2-C4-알킬을 나타내거나, 또는 1 내지 2개의 산소 및/또는 황원자으로 차단될 수 있는 시클로 알킬을 나타내거나, 또는 각각 임의로 불소, 염소, 브롬, 메틸, 에틸, 프로필, i-프로필, 메톡시, 에톡시, 트리플루오로메틸 또는 니트로로 치환된 아릴, 피리딘, 이미다졸, 피라졸, 트리아졸, 인돌, 티아졸 또는 아릴-C1-C3-알킬을 나타내고, B가 수소 또는 각각의 경우에서 직쇄 또는 측쇄의 C1-C8-알킬 또는 C1-C4-알콕시알킬을 나타내거나, 또는 A 및 B가 이들이 결합된 탄소원자와 함께, C1-C4-알킬, C1-C4-알콕시, 트리플루오로메틸, 트리플루오로메톡시, 불소, 염소 및 치환된 페닐로 치환될 수 있고, 산소 및/또는 황으로 차단될 수 있는 3 내지 6원의 포화 또는 불포화환을 형성하며, R이 일반식 (a), (b), (c) 또는 (d)로 표시되는 그룹을 나타내고,상기식에서, L 및 M은 각각 산소 또는 황을 나타내고, 단 L 및 M은 동시에 산소를 나타내지 않으며, R1, R2및 R3가 개개 독립적으로 각각 임의로 불소 또는 염소로 치환된 C1-C4-알킬, C1-C4-알콕시, C1-C4-알킬아미노, 디-(C1-C4)아미노, 또는 C1-C4-알킬티오를 나타내거나, 또는 각각 임의로 불소, 브롬, 니트로, 시아노, C1-C2-알콕시, C1-C4-플루오로알콕시, C1-C2-클로로알콕시, C1-C2-알킬티오, C1-C2-플루오로 알킬티오, C1-C2-클로로알킬티오 또는 C1-C3-알킬로 치환된 페닐, 벤질, 페녹시 또는 페닐티오를 나타내고, R4및 R5가 개개 독립적으로 각각 임의로 불소, 염소 또는 브롬으로 치환된 C1-C10-알킬, C1-C10-알콕시, 또는 C1-C10-알콕시-(C1-C10)알킬을 나타내거나, 또는 임의로 불소, 염소, 브롬, C1-C20-할로게노알킬, C1-C20-알킬 또는 C1-C4-알콕시로 치환된 페닐을 나타내거나, 또는 임의로 불소, 염소, 브롬, C1-C4-알킬, C1-C4-할로게노알킬 또는 C1-C4-알콕시로 치환된 벤질을 나타내고, R6가 임의로 불소, 염소 또는 브롬으로 치환되고, 산소로 차단될 수 있는 C1-C120-알킬을 나타내거나, 또는 임의로 불소, 염소, 브롬, C1-C4-할로게노알킬 또는 C1-C4-알콕시로 치환된 페닐을 나타내거나, 임의로 불소, 염소, 브롬, C1-C4-할로게노알킬 또는 C1-C4-알콕시로 치환된 벤질을 나타내는 일반식(I)의 치환된 3-아릴-피롤리딘-2,4-디온유도체 및 일반식(I)의 화합물의 순수한 거울상 이성체 형태.
- (A)일반식(II)의 3-아릴-피롤리딘-2,4-디온 또는 그의 엔올을 경우에 따라 희석제의 존재하에서, 경우에 따라 산-결합제의 존재하에서 및 경우에 따라 상-이동 촉매의 존재하에서 일반식(III)인 인화합물과 반응시켜 일반식(Ia)의 치환된 3-아릴-피롤리딘-2,4-디온을 수득하거나, (B)일반식(II)의 화합물을 경우에 따라 희석제의 존재하에서 및 경우에 따라 산-결합제의 존재하에서 일반식(IV)의 술포닐클로라이드와 반응시켜 일반식(Ib)의 화합물을 수득하거나, (C)일반식(II)의 화합물을 α)경우에 따라 희석제의 존재하에서 및 경우에 따라 촉매의 존재하에서 일반식(V)의 이소시아네이트와 반응시키거나, β)경우에 따라 희석제의 존재하에서 및 경우에 따라 산-결합제의 존재하에서 일반식(VI)의 카르밤산클로라이드 또는 티오카르밤산 클로라이드와 반응시켜, 일반식(Ic)의 화합물을 α)경우에 따라 희석제의 존재하에서 및 경우에 따라 산-결합제의 일반식(VII)의 클로로 모노티오포름산 에스테르, 클로로포름산티오에스테르 또는 클로로디티오포름산 에스테르와 반응시키거나, β)이황화탄소와 반응시키고, 계속해서 일반식(VIII)의 알킬할라이드와 반응시켜, 일반식(Id)의 화합물을 수득함을 특징으로 하여 일반식(I)의 치환된 3-아릴-피롤리딘-2,4-디온 유도체를 제조하는 방법.상기 식에서, X는 알킬, 할로겐 또는 알콕시를 나타내고, Y는 수소, 알킬, 할로겐, 알콕시 또는 할로게알킬을 나타내며, Z는 알킬, 할로겐 또는 알콕시를 나타내고, n은 0 내지 3의 숫자를 나타내며, A는 수소를 나타내거나, 또는 각각 임의로 할로겐으로 치환된 알킬, 알콕시알킬 또는 알킬티오알킬, 헤테로원자로 임의로 차단된 시클로알킬을 나타내거나, 또는 각각 할로겐, 알킬, 할로게노알킬, 알콕시 또는 니트로로 임의로 치환된 아릴, 아릴알킬 또는 헤트아릴을 나타내고, B는 수소, 알킬 또는 알콕시알킬을 나타내거나, 또는 A 및 B는 이들이 결합된 탄소원자와 함께, 임의로 치환된, 산소 및/또는 황으로 차단될 수 있는 포화 또는 불포화환을 형성하며, R은 일반식 (a),(b),(c)또는 (d)로 표시되는 그룹을 나타내고,상기 식에서, L 및 M은 산소 또는 황을 나타내고, 단 L 및 M은 동시에 산소를 나타내지 않으며, R1, R2및 R3는 독립적으로 각각 임의로 할로겐 치환된 알킬, 알콕시, 알킬아미노, 디알킬아미노, 알킬티오, 알케닐티오, 알키닐티오 및 시클로알킬티오를 나타내고, 또한 각각 임의로 치환된 페닐, 벤질, 페녹시 또는 페닐티오를 나타내고, R4및 R5는 독립적으로 각각 수소를 나타내거나, 또는 각각 임의로 할로겐으로 치환된 알킬, 알케닐, 알콕시 또는 알콕시알킬을 나타내거나, 또는 임의로 치환된 페닐 또는 임의로 치환된 벤질을 나타내거나, 또는 R4및 R5는 함께 임의로 산소원자로 차단된 알케닐 라디칼을 나타내며, R6는 임의로 할로겐으로 치환되고, 산소로 차단될 수 있는 알킬을 나타내거나, 또는 임의로 할로겐, 할로게노알킬 또는 알콕시로 치환된 페닐을 나타내거나, 또는 임의로 할로겐, 할로게노알킬, 알킬 및 알콕시로 치환된 벤질을 나타내거나, 또는 알케닐 또는 알키닐을 나타내고, 일반식(III)에서 Hal은 할로겐, 특히 염소 및 브롬을 나타내며, 일반식(VIII)에서 Hal은 염소, 브롬 또는 요오드를 나타낸다.
- 적어도 하나의 일반식(I)의 3-아릴-피롤리딘-2,4-디온 유도체를 함유함을 특징으로 하는 살충, 살비 및 제초제.
- 일반식(I)의 3-아릴-피롤리딘-2,4-디온 유도체를 곤충 및/또는 진드기 및/또는 잡초 및/또는 이들의 환경에 적응시킴을 특징으로 하는 곤충 및/또는 진드기 및/또는 잡초를 구제하는 방법.
- 곤충 및/또는 진드기 및/또는 잡초를 구제하기 위한 일반식(I)의 3-아릴-피롤리딘-2,4-디온 유도체의 용도.
- 일반식(I)의 3-아릴-피롤리딘-2,4-디온 유도체를 중량제 및/또는 계면활성제와 혼합함을 특징으로 하여 살충 및/또는 살비 및/또는 제초제를 제조하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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DE4107394A1 (de) * | 1990-05-10 | 1991-11-14 | Bayer Ag | 1-h-3-aryl-pyrrolidin-2,4-dion-derivate |
AU666040B2 (en) * | 1992-10-28 | 1996-01-25 | Bayer Aktiengesellschaft | Substituted 1-H-3-aryl-pyrrolidine-2,4-dione derivatives |
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BR112012020084B1 (pt) | 2010-02-10 | 2017-12-19 | Bayer Intellectual Property Gmbh | A process for the preparation of pesticides and / or herbicides and / or fungi and / or fungi and / or fungicides and / or fungicides and / or fungicides and / or fungicides. METHOD FOR INCREASING THE ACTION OF PESTICIDES AND / OR HERBICIDES AND / OR FUNGICIDES COMPREHENDING SUCH COMPOUNDS |
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KR101789527B1 (ko) | 2011-03-01 | 2017-10-25 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 2-아실옥시피롤린-4-온 |
DE102011080406A1 (de) | 2011-08-04 | 2013-02-07 | Bayer Pharma AG | Substituierte 3-(Biphenyl-3-yl)-4-hydroxy-8-methoxy-1-azaspiro8[4.5]dec-3-en-2-one |
CN104066332B (zh) | 2012-01-26 | 2016-10-26 | 拜耳知识产权有限责任公司 | 用于控制鱼类寄生虫的苯基取代的酮烯醇 |
BR112018014326B1 (pt) | 2016-01-15 | 2021-11-16 | Bayer Cropscience Aktiengesellschaft | Processo para preparaqao de 2-aril-etanois substituidos |
WO2019197620A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Cropscience Aktiengesellschaft | Verwendung von tetramsäurederivaten zur bekämpfung von speziellen insekten |
AU2019250592A1 (en) | 2018-04-13 | 2020-10-22 | Bayer Aktiengesellschaft | Use of tetramic acid derivatives for controlling pests by watering or droplet application |
WO2019197652A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Aktiengesellschaft | Feststoff-formulierung insektizider mischungen |
MX2020010794A (es) | 2018-04-13 | 2020-10-28 | Bayer Cropscience Ag | Uso de derivados del acido tetramico para combatir insectos especiales. |
WO2019197617A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Cropscience Aktiengesellschaft | Verwendung von tetramsäurederivaten zur bekämpfung von tierischen schädlingen durch angiessen, tröpfchenapplikation. pflanzlochbehandlung oder furchenapplikation |
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US4104043A (en) * | 1972-12-12 | 1978-08-01 | Union Carbide Corporation | Esters of 3-hydroxyindone compounds as herbicides and miticides |
US4925868A (en) * | 1986-08-29 | 1990-05-15 | Takeda Chemical Industries, Ltd. | 4-Hydroxy-3-pyrrolin-2-ones and treatment of circulatory disorders therewith |
US4985063A (en) * | 1988-08-20 | 1991-01-15 | Bayer Aktiengesellschaft | 3-aryl-pyrrolidine-2,4-diones |
DE58907411D1 (de) * | 1989-01-07 | 1994-05-11 | Bayer Ag | 3-Aryl-pyrrolidin-2,4-dion-Derivate. |
DE3928504A1 (de) * | 1989-08-29 | 1991-03-07 | Bayer Ag | 4-alkoxy- bzw. 4-(substituierte)amino-3-arylpyrrolinon-derivate |
DE4032090A1 (de) * | 1990-02-13 | 1991-08-14 | Bayer Ag | Polycyclische 3-aryl-pyrrolidin-2,4-dion-derivate |
DE4004496A1 (de) * | 1990-02-14 | 1991-08-22 | Bayer Ag | 3-aryl-pyrrolidin-2,4-dion-derivate |
DE4107394A1 (de) * | 1990-05-10 | 1991-11-14 | Bayer Ag | 1-h-3-aryl-pyrrolidin-2,4-dion-derivate |
-
1991
- 1991-06-28 DE DE4121365A patent/DE4121365A1/de not_active Withdrawn
-
1992
- 1992-06-16 ES ES92110119T patent/ES2120424T3/es not_active Expired - Lifetime
- 1992-06-16 DE DE59209490T patent/DE59209490D1/de not_active Expired - Fee Related
- 1992-06-16 EP EP92110119A patent/EP0521334B1/de not_active Expired - Lifetime
- 1992-06-24 JP JP18897492A patent/JP3178903B2/ja not_active Expired - Fee Related
- 1992-06-25 CA CA002072280A patent/CA2072280A1/en not_active Abandoned
- 1992-06-26 KR KR1019920011297A patent/KR100231804B1/ko not_active IP Right Cessation
- 1992-06-26 ZA ZA924746A patent/ZA924746B/xx unknown
- 1992-06-26 MX MX9203644A patent/MX9203644A/es unknown
- 1992-07-07 BR BR929202473A patent/BR9202473A/pt not_active IP Right Cessation
-
1995
- 1995-06-07 US US08/483,913 patent/US5589469A/en not_active Expired - Fee Related
-
1996
- 1996-06-03 US US08/657,076 patent/US5616536A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
BR9202473A (pt) | 1993-02-09 |
JPH05221971A (ja) | 1993-08-31 |
DE59209490D1 (de) | 1998-10-15 |
MX9203644A (es) | 1993-11-01 |
US5616536A (en) | 1997-04-01 |
ES2120424T3 (es) | 1998-11-01 |
US5589469A (en) | 1996-12-31 |
CA2072280A1 (en) | 1992-12-29 |
EP0521334A1 (de) | 1993-01-07 |
KR100231804B1 (ko) | 2000-02-01 |
ZA924746B (en) | 1993-03-31 |
DE4121365A1 (de) | 1993-01-14 |
EP0521334B1 (de) | 1998-09-09 |
JP3178903B2 (ja) | 2001-06-25 |
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