KR900011726A - 3-아릴-피롤리딘-2.4-디온 유도체 및 이의 제조방법 - Google Patents
3-아릴-피롤리딘-2.4-디온 유도체 및 이의 제조방법 Download PDFInfo
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- KR900011726A KR900011726A KR1019900000102A KR900000102A KR900011726A KR 900011726 A KR900011726 A KR 900011726A KR 1019900000102 A KR1019900000102 A KR 1019900000102A KR 900000102 A KR900000102 A KR 900000102A KR 900011726 A KR900011726 A KR 900011726A
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- 238000002360 preparation method Methods 0.000 title claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 41
- 150000002367 halogens Chemical group 0.000 claims 41
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 13
- 229910052801 chlorine Inorganic materials 0.000 claims 13
- 239000000460 chlorine Chemical group 0.000 claims 13
- 229910052731 fluorine Inorganic materials 0.000 claims 13
- 239000011737 fluorine Chemical group 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 11
- -1 C1-C 6 -alkyl Inorganic materials 0.000 claims 10
- 150000002431 hydrogen Chemical group 0.000 claims 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 230000009467 reduction Effects 0.000 claims 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 7
- 229910052794 bromium Inorganic materials 0.000 claims 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 7
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 239000001301 oxygen Substances 0.000 claims 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 125000001188 haloalkyl group Chemical group 0.000 claims 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 5
- 241000196324 Embryophyta Species 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000004434 sulfur atom Chemical group 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 241000239223 Arachnida Species 0.000 claims 3
- 241000233866 Fungi Species 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 239000003085 diluting agent Substances 0.000 claims 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims 2
- 241000238631 Hexapoda Species 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 230000000895 acaricidal effect Effects 0.000 claims 2
- 239000000642 acaricide Substances 0.000 claims 2
- 239000011230 binding agent Substances 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
- 125000004438 haloalkoxy group Chemical group 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
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 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
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000006482 condensation reaction Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 230000000855 fungicidal effect Effects 0.000 claims 1
- 239000000417 fungicide Substances 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 239000008233 hard water Substances 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 claims 1
- 239000004009 herbicide Substances 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 239000002917 insecticide Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000000575 pesticide Substances 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
-
- 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
-
- 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
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
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Description
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Claims (13)
1. 일반식(I)의 3-아릴-피롤리딘-2,4-디온 유도체 및 거울상입체 이성적으로 순수한 형태의 일반식(I)의 화합물.
상기식에서,X는 알킬, 할로겐 또는 알콕시이고, Y는 수소, 알킬, 할로겐, 알콕시 또는 할로게노알킬이며, Z는 알킬, 할로겐 또는 알콕시이고, n 은 0내지 3이며, R은 수소, 그룹-CO-R' [여기에서, R¹은 알킬, 알케닐, 알콕시알킬, 알킬티오알킬, 폴리알콕시알킬 또는 헤테로원자에 의해 차된될 수 있는 사이클로알킬 (이들 라디칼 각각은 할로겐으로 임의로 치환된다) 이거나, 임의로 치환된 페닐, 임의로 치환된 페닐알킬, 치환된 헤트아릴, 치환된 페녹시알킬 또는 치환된 헤트아릴옥시알킬이다], 또는-CO-O-R² [여기에서, R²는 알킬, 알케닐, 알콕시알킬, 폴리알콕시알킬, 임의로 치환된 페닐 또는 사이클로알킬(이들 라디칼 각각은 할로겐으로 임의로 치환된다)이다]이고, A는 알킬, 알케닐, 알키닐알콕시알킬, 폴리알콕시알킬, 알킬티오알킬, 또는 헤테로원자에 의해 임의로 차단된 사이클로알킬(이들 라디칼 각각은 할로겐에 의해 임의로 치환된다)이거나, 할로겐, 알킬, 할로게노 알킬, 알콕시 또는 니트로로 임의로 치환된 아릴 알킬이다)이며, B 및 C＊는 서로 독립적으로 수소, 알킬 또는 알콕시알킬이다.
제1항에 있어서, X가 C₁-C6-알킬, 할로겐 또는 C₁-C6-알콕시이고, Y가 수소, C₁-C6- 알킬, 할로겐, C₁-C6-알콕시 또는 C₁-C₃-할로게노알킬이며, Z가 C₁-C6-알킬, 할로겐 또는 C₁-C6-알콕시이고,n이 0내지 3이며, R이 수소(Ia), 일반식-CO-R¹(Ib)[여기에서, R¹은 C₁-C20-알킬, C₂-C20-알케닐, C₁-C8-알콕시-C₂-C8-알킬, C₁-C8-알킬티오-C₂-C8-알킬, C₁-C8-폴리알콕시 또는 3내지 8개의 환원을 가지며 산소 및/또는 황에 의해 임의로 치환될 수 있다)이거나, 할로겐, 니트로, C₁-C6-알킬, C₁-C6-알콕시, C₁-C6-할로게노알킬, 또는 C₁-C6-할로게노알콕시에 의해 차단될수 있는 사이클로 알킬(이들 라디칼 각각은 할로겐에 의해 임의로 치환된 페닐이거나, 할로겐, C₁-C6-알킬, C₁-C6-알콕시, C₁-C6-할로게노알킬 또는 C₁-C6-할로게노알콕시에 의해 임의로 치환된 페닐-C₁-C6-알킬이거나, 할로겐 및 C₁-C6-알킬로 임의로 치환된 헤트아릴이거나, 할로겐 및 C₁-C6-알킬에 의해 임의로 치환된 페녹시-C₁-C6-알킬이거나, 할로겐, 아미노 및 C₁-C6-알킬로 임의로 치환된 헤트아릴옥시-C1-C6-알킬이다], 또는 -CO-O-R²(Ic)의 그룹 [여기에서, R²는 C₁-C20-알킬, C₂-C20-알케닐, C₁-C8-알콕시-C₂-C8-알킬 또는 C₁-C8-폴리알콕시-C₂-C8-알킬(이들 라디칼 각각은 할로겐으로 임의로 치환된다)이거나, 3내지 8개의 환원을 가지는 페닐 또는 사이클로알킬 (이들 라디칼 각각은 할로겐, 니트로, C₁-C6-알킬, C₁-C6-알콕시 또는 C₁-C6-할로게노알킬로 임의로 치환된다)이다]이고, A가 직쇄 또는 측쇄 C₁-C12-알킬, C₃-C8-알케닐 C₃-C8-알키닐, C₁-C10-알콕시-C₂-C8-알킬, C₁-C8-폴리알콕시-C₂-C8-알킬 또는 3내지 8개의 환원을 가지며 산소 및/또는 황으로 차단될 수 있는 사이클로알킬 (이들 라디칼 각각은 할로겐으로 임의 치환된다)이거나, 할로겐, C₁-C6-알킬-C₁-C6-할로알킬, C₁-C6-알킬이고, B 및 C*가 서로 독립적으로 수소, 직쇄 또는 측쇄 C₁-C12-알킬 또는 C₁-C8-알콕시알킬인 일반식(I)의 3-아릴-피롤리딘-2,4-디온 유도체 및 거울상 입체 이성적으로 순수한 형태의 일반식(I)의 화합물.
제1항에 있어서, X가 C₁-C₄-알킬, 할로겐 또는 C₁-C₄-알콕시이며, Y가 수소 C₁-C6-알킬, 할로겐, C₁-C₄-알콕시 또는 C₁-C₂-할로게노알킬이고, Z가 C₁-C₄-알킬, 할로겐 또는 C₁-C₄-알콕시이며, n이 0내지 3이고, R이 수소(Ia), 일반식 -CO-R¹(Ib) [여기에서 R¹은 C₁-C10-알킬, C₂-C10-알케닐. C₁-C6-알콕시-C₂-C6-알킬, C₁-C6-알킬티오-C₂-C6-알킬, C1-C6-폴리알콕실, C2-C6-알킬, 또는 3내지 7개의 환원을 가지며 1내지 2개의 산소 및/또는 황원자에 의해 차단될 수 있는 사이클로알킬(이들 라디칼중 각각은 할로겐으로 임의로 치환된다)이거나, 할로겐, 니트로, C₁-C₄-알킬, C₁-C₄-알콕시, C₁-C₃-할로게노알킬 또는 C₁-C₃-할로게노알콕시로 임의로 치환된 페닐이거나, 할로겐, C₁-C₄-알킬, C₁-C₄-알콕시, C₁-C₃-할로게노알킬 또는 C₁-C₃-할로게노알콕시로 임의로 치환된 페닐-C₁-C₄-알킬 이거나, 할로겐 및 C₁-C6-알킬로 임의로 치환된 헤트아릴이거나, 할로겐 및 C₁-C₄-알킬로 임의로 치환된 페녹시-C₁-C5-알킬이거나, 할로겐, 아미노 및 C₁-C₄-알킬로 임의로 치환된 헤트아릴옥시-C₁-C5-알킬이다]. 또는 -CO-O-R²(Ic)의 그룹[여기에서, R²는 C₁-C₁6-알킬, C₁-C16-알케닐, C₂-C16-알콕시-C₂-C6-알킬 또는 C₁-C6-폴리알콕시-C₂-C6-알킬(이들 라디칼 각각은 할로겐으로 임의로 치환된다)이거나, 페닐 또는 3내지 7개의 환원을 갖는 사이클로알킬(이들 라디칼 각각은 할로겐, 니트로, C₁-C₄-알킬, C₁-C₃-알콕시 또는 C₁-C₃-할로게노알킬로 임의로 치환된다)이다]이며, A가 직쇄 또는 측쇄 C₁-C10-알킬, C₃-C6-알케닐, C₃-C6-알키닐, C₁-C8-알콕시-C₂-C6-알킬, C₁-C6-폴리알콕시-C₂-C|6-알킬, C₁-C8-알킬티오-C₂-C6-알킬, 또는 3내지 7개의 환원을 가지며 1내지 2개의 산소 및/ 또는 황원자에 의해 차단될 수 있는 사이클로알킬(이들 라디칼 각각은 할로겐으로 임의로 치환된다)이거나, 할로겐, C₁-C₄-알킬,C₁-C₄-할로알킬-C₁-C₄-알콕시 또는 니트로로 임의로 치환된 아릴-C₁-C₄-알킬이고, B 및 C*는 서로 독립적으로 수소, 직쇄 또는 측쇄 C₁-C10-알킬 및 C₁-C6-알콕시알킬인 일반식(I)의 3-아릴피롤리딘-2,4-디온 유도체 및 거울상입체이성적으로 순수한 일반식(I)의 화합물.
제1항에 있어서, X가 메틸, 에틸, 프로필, i-프로필, 불소, 염소, 브롬, 메톡시 또는 에톡시이고, Y가 수소, 메틸, 에틸, 프로필, i-프로필, 부틸, i-부틸, 3급-부틸, 불소, 염소, 브롬, 메톡시, 에톡시 또는 트리플루오로케틸이며, Z가 메틸, 에틸,i-프로필, 부틸, i-부틸, 3급-부틸, 불소, 염소, 브롬, 메톡시 또는 에톡시이고, n이 0내지 2이며, R이 수소(Ia), 일반식 -CO-R¹(Ib) [여기에서, R¹은 C₁-C₄-알킬, C₂-C14-알케닐, C₁-C4-알콕시-C₂-C6-알킬, C₁-C₄-알킬티오-C₂-C6-알킬, C₁-C₄-폴리알콕시-C₂-C₄-알킬, 또는 3내지 6개의 환원을 가지며 1내지 2개의 산소 및/또는 황원자로 차단될 수 있는 사이클로알킬(이들 라디칼 각각은 불소 또는 염소로 임의로 치환되다)이거나, 불소, 염소, 브롬, 메틸, 에틸, 프로필, i-프로필, 메톡시, 에톡시, 트리플루오로메틸, 트리플루오로메톡시 또는 니트로로 임의로 치환된 페닐이거나, 불소, 염소, 브롬, 메틸, 에틸, 프로필, i-프로필, 메톡시, 에톡시, 트리플루오로메틸 또는 트리플루오로 메톡시로 임의로 치환된 페닐-C₁-C₃-알킬이거나, 피리딜, 피리미딜, 티아졸릴 및 피라졸릴(이들 라디칼 각각은 불소, 염소, 브롬, 메틸 또는 에틸로 임의로 치환되다)이거나, 불소, 염소, 메틸 또는 에틸로 임의로 치환된 페녹시-C₁-C₄-알킬이거나 피리딜옥시-C₁-C₄-알킬, 피리미딜옥시-C₁-C₄-알킬 또는 티아졸릴옥시-C₁-C₄-알킬(이들 라디칼 각각은 불소, 염소, 아미노, 메틸 또는 에틸로 임의로 치환된다)이다] 또는 일반식-CO-O-R²(Ic) [여기에서, R²는 C₁-C₄-알킬, C₂-C14-알케닐,C₁-C₄-알콕시-C₂-C6-알킬 또는C₁-C₄-폴리 알콕시-C₂-C6-알킬(이들 라디칼 각각은 불소 또는 염소로 임의로 치환된 라디칼이다)이거나, 페닐 또는 3내지 6개의 환원을 가지는 사이클로알킬(이들 라디칼 각각은 불소, 염소, 니트로, 메틸. 에틸프로필, i-프로필, 메톡시, 에톡시 또는 트리플루오로메틸에 의해 임의로 치환된다)이다]이며, A가 직쇄 또는 측쇄 C₁-C8-알킬, C₃-C₄-알케닐, C₃-C₄-알키닐, C₁-C6-알콕시-C₂-C₄-알킬, C₁-C₄-폴리알콕시-C₂-C₄-알킬, C₁-C6-알킬티오-C₂-C₄-알킬, 또는 3내지 6개의 환원을 가지며 1내지 2개의 산소및/또는 황원자에 의해 차단될 수 있는 사이클로알킬(이들 라디칼 각각은 할로겐에 의해 임의로 치환된다)이거나, 불소, 염소, 브롬, 메틸, 에틸, 프로필, 이소프로필, 메톡시, 에톡시, 트리플루오로메틸 또는 니트로로 임의로 치환된 아릴-C₁-C₃-알킬이며, B 및 C*가 서로독립적으로 수소, 직쇄 또는 측쇄C₁-C8-알킬 및 C₁-C₄-알콕시알킬인 일반식(I)의 3-아릴피롤리딘-2,4-디온 유도체 및 거울상 입체이성적으로 순수한 형태의 일반식(I)의 화합물.
(A) 일반식(II)의 N-아실아미노산 에스테르를 희석제 및 염기의 존재하에 분자내 축합반응에 적용시켜 일반식(Ia)의 화합물을 수득하거나, (B) 일반식(Ia)의 화합물을 a)필요한 경우 희석제의 존재하에 및 필요한 경수 산결합제의 존재하에 일반식(III)의 산할라이드 또는 b) 필요한 경우 희석제 및 필요한 경우 산-결합제의 존재하에 일반식(IV)의 카복실산 무수물과 반응시켜 일반식(Ib)의 화합물을 수득하거나 (C) 일반식(Ia)의 화합물을 필요한 경우 희석제 및 필요한 경우 산-결합제의 존재하에 일반식(V)의 클로로포름산 에스테르와 반응시켜 일반식(Ic)의 화합물을 수득함을 특징으로 하여, 일반식(I)의 3-아릴-피롤리딘-2,4-디온 유도체를 제조하는 방법.
상기식에서, X는 알킬, 할로겐 또는 알콕시이고, Y는 수소 알킬, 할로겐 알콕시 또는 할로게노알킬이며,Z는 알킬, 할로겐 또는 알콕시이고, n은 0내지 3이며, R은 수소, 그룹 -CO-R¹ [여기에서, R¹은 알킬, 알케닐, 알콕시알킬, 알킬티오알킬, 폴리알콕시알킬 또는 헤테로원자에 의해 차단될 수 있는 사이클로알킬 (이들 라디칼 각각은 할로겐으로 임의로 치환된다)이거나, 임의로 치환된 페닐, 임의로 치환된 페닐 알킬, 치환된 헤테아릴, 치환된 페녹시알킬 또는 치환된 헤트아릴알킬이다], 또는 -CO-O-R² [여기에서, R²는 알킬, 알케닐, 알콕시알킬, 폴리알콕시알킬, 임의로 치환된 페닐 또는 사이클로알킬(이들 라디칼 각각은 할로겐으로 임의로 치환된다)이다]이고, A는 알킬, 알케닐, 알키닐, 알콕시알킬, 폴리알콕시알킬, 알킬티오알킬, 또는 헤테로원자에 의해 임의로 차단된 사이클로알킬(이들 라디칼 각각은 할로겐에 의해 임의로 치환되거나, 할로겐, 알킬, 할로게노알킬, 알콕시 또는 니트로로 임의로 치환된 아릴 알킬이다)이며, B 및 C*는 서로 독립적으로 수소, 알킬 또는 알콕시알킬이고,R3는 알킬이며, Hal은 할로겐, 특히 염소 및 불소이다.
적어도 하나의 일반식(I)의 3-아릴-피롤리딘-2,4-디온 유도체를 함유함을 특징으로 하는 살충제, 살비제 및/또는 제초제.
일반식(I)의 3-아릴-피롤리딘-2,4-디온 유도체를 거미류, 잡초 및/또는 이들의 서식지에 적용시킴을 특징으로 하여, 곤충, 거미류 및/또는 잡초를 방제하는 방법.
곤충, 거미류 및/또는 잡초를 방제하기 위한 일반식(I)의 3-아릴-피로리딘-2,4-디온 유도체의 용도.
일반식(I)의 3-아릴-피롤리딘-2,4-디온 유도체를 중량제 및/또는 계면활성제와 혼합시킴을 특징으로 하여, 살충제, 살비제 및/또는 잡초를 제조하는 방법.
제1항 내지 4항중 어느 한 항에 있어서, 진균류를 방제하기 위한 3-아릴-피롤리딘-2,4-디온 유도체.
제1항 내지 4항중 어느 한 항에 있어서, 살진균제를 함유하는 3-아릴-피롤리딘-2,4-디온 유도체.
진균류를 방제하기 위한 제1항 내지 4항중 어느 한 항에 따른 3-아릴-피롤리딘-2,4-디온 유도체의 용도.
진균류 방제용 약제의 제조를 위한 제1항 내지 4항중 어느 한 항에 따른 3-아릴-피롤리딘-2,4-디온 유도체의 용도.
※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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| DE3900301 | 1989-01-07 | ||
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| Country | Link |
|---|---|
| US (1) | US5045560A (ko) |
| EP (1) | EP0377893B1 (ko) |
| JP (1) | JP2839167B2 (ko) |
| KR (1) | KR900011726A (ko) |
| AU (1) | AU620193B2 (ko) |
| BR (1) | BR9000040A (ko) |
| CA (1) | CA2007239A1 (ko) |
| DE (1) | DE58907411D1 (ko) |
| ES (1) | ES2063108T3 (ko) |
Families Citing this family (99)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5186737A (en) * | 1989-01-07 | 1993-02-16 | Bayer Aktiengesellschaft | Pesticidal 3-aryl-pyrrolidine-2,4-diones |
| DE58907411D1 (de) * | 1989-01-07 | 1994-05-11 | Bayer Ag | 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 |
| DE4102339A1 (de) * | 1991-01-26 | 1992-07-30 | Bayer Ag | Substituierte 3-phenyl-4-hydroxy-(delta)(pfeil hoch)3(pfeil hoch)-pyrrolin-2-one |
| US5811374A (en) * | 1991-02-07 | 1998-09-22 | Bayer Aktiengesellschaft | 3-aryl-pyrrolidine-2,4-dione derivatives |
| CA2106302A1 (en) * | 1991-03-19 | 1992-09-20 | Frederik Cederbaum | Herbicidally, acaricidally and insecticidally active compounds |
| DE4121365A1 (de) * | 1991-06-28 | 1993-01-14 | Bayer Ag | Substituierte 1-h-3-aryl-pyrrolidin-2,4-dion-derivate |
| DE4141399A1 (de) * | 1991-12-16 | 1993-06-17 | Bayer Ag | 4-(substituierte)amino-3-arylpyrrolinon-derivate |
| DE4223015A1 (de) * | 1992-07-13 | 1994-01-20 | Bayer Ag | Substituierte 3-Benzoyl-pyrrolidin-2,4-dion-Derivate |
| JPH06172306A (ja) * | 1992-10-05 | 1994-06-21 | Nissan Chem Ind Ltd | 環状アミド化合物および除草剤 |
| BR9407046A (pt) | 1993-07-02 | 1996-08-13 | Bayer Ag | Derivados de 1h-3-aril-pirrolidina-2,4-diona espiroheterociclicos substituidos processos para sua preparaçao e seu uso como pesticidas |
| AU7072694A (en) * | 1993-07-05 | 1995-02-06 | Bayer Aktiengesellschaft | Substituted aryl-keto-enolic heterocycles |
| DE4402403A1 (de) * | 1994-01-27 | 1995-08-03 | Bayer Ag | Verfahren zur Herstellung von substituierten Phenylessigsäurederivaten und neue Zwischenprodukte |
| DE4431730A1 (de) * | 1994-02-09 | 1995-08-10 | Bayer Ag | Substituierte 1H-3-Aryl-pyrrolidin-2,4-dion-Derivate |
| DE19520816A1 (de) * | 1995-05-30 | 1996-12-05 | Hoechst Schering Agrevo Gmbh | Herbizide Pyrrolinone |
| WO1997036868A1 (de) | 1996-04-02 | 1997-10-09 | Bayer Aktiengesellschaft | Substituierte phenylketoenole als schädlingsbekämpfungsmittel und herbizide |
| CN100339352C (zh) | 1996-08-05 | 2007-09-26 | 拜尔公司 | 2－和2,5－取代的苯基酮烯醇 |
| GB2322300A (en) * | 1997-02-20 | 1998-08-26 | Reckitt & Colman Inc | Miticidal and disinfectant composition |
| DE19808261A1 (de) * | 1998-02-27 | 1999-10-28 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
| DE19813354A1 (de) * | 1998-03-26 | 1999-09-30 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
| DE19818732A1 (de) * | 1998-04-27 | 1999-10-28 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
| AU4315700A (en) * | 1999-05-11 | 2000-11-21 | Nippon Kayaku Co. Ltd. | N-substituted dihydropyrrole derivatives |
| DE19935963A1 (de) | 1999-07-30 | 2001-02-01 | Bayer Ag | Biphenylsubstituierte cyclische Ketoenole |
| DE19946625A1 (de) | 1999-09-29 | 2001-04-05 | Bayer Ag | Trifluormethylsubstituierte spirocyclische Ketoenole |
| DE10016544A1 (de) * | 2000-04-03 | 2001-10-11 | Bayer Ag | C2-phenylsubstituierte Ketoenole |
| AR029677A1 (es) * | 2000-06-29 | 2003-07-10 | Bayer Ag | Combinaciones de compuestos activos con propiedades insecticidas y acaricidas |
| DE10055941A1 (de) | 2000-11-10 | 2002-05-23 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE10062422A1 (de) * | 2000-12-14 | 2002-06-20 | Bayer Ag | Verwendung von Acetyl-CoA Carboxylase zum Identifizieren von insektizid wirksamen Verwendung |
| DE10139465A1 (de) * | 2001-08-10 | 2003-02-20 | Bayer Cropscience Ag | Selektive Herbizide auf Basis von substituierten, cayclischen Ketoenolen und Safenern |
| DE10311300A1 (de) | 2003-03-14 | 2004-09-23 | Bayer Cropscience Ag | 2,4,6-Phenylsubstituierte cyclische Ketoenole |
| DE10326386A1 (de) | 2003-06-12 | 2004-12-30 | Bayer Cropscience Ag | N-Heterocyclyl-phenylsubstituierte cyclische Ketoenole |
| DE10330724A1 (de) | 2003-07-08 | 2005-01-27 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE10351647A1 (de) * | 2003-11-05 | 2005-06-09 | Bayer Cropscience Ag | 2-Halogen-6-alkyl-phenyl substituierte Tetramsäure-Derivate |
| DE10354628A1 (de) * | 2003-11-22 | 2005-06-16 | Bayer Cropscience Ag | 2-Ethyl-4,6-dimethyl-phenyl-substituierte Tetramsäure-Derivate |
| DE10354629A1 (de) | 2003-11-22 | 2005-06-30 | Bayer Cropscience Ag | 2-Ethyl-4,6-dimethyl-phenyl substituierte spirocyclische Tetramsäure-Derivate |
| AU2004294259C1 (en) | 2003-12-04 | 2014-07-10 | Bayer Cropscience Aktiengesellschaft | Active substance combination having insecticidal and acaricidal properties |
| DE102004014620A1 (de) | 2004-03-25 | 2005-10-06 | Bayer Cropscience Ag | 2,4,6-phenylsubstituierte cyclische Ketoenole |
| DE102004035133A1 (de) * | 2004-07-20 | 2006-02-16 | Bayer Cropscience Ag | Selektive Insektizide auf Basis von substituierten, cyclischen Ketoenolen und Safenern |
| DE102004044827A1 (de) | 2004-09-16 | 2006-03-23 | Bayer Cropscience Ag | Jod-phenylsubstituierte cyclische Ketoenole |
| DE102004053191A1 (de) * | 2004-11-04 | 2006-05-11 | Bayer Cropscience Ag | 2,6-Diethyl-4-methyl-phenyl substituierte Tetramsäure-Derivate |
| DE102004053192A1 (de) * | 2004-11-04 | 2006-05-11 | Bayer Cropscience Ag | 2-Alkoxy-6-alkyl-phenyl substituierte spirocyclische Tetramsäure-Derivate |
| DE102005008021A1 (de) | 2005-02-22 | 2006-08-24 | Bayer Cropscience Ag | Spiroketal-substituierte cyclische Ketoenole |
| DE102005008033A1 (de) * | 2005-02-22 | 2006-08-24 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| CN1752075A (zh) * | 2005-09-26 | 2006-03-29 | 南京农业大学 | 一种生物源化合物的结构修饰产品及其用于除草 |
| WO2007046554A1 (ja) * | 2005-10-21 | 2007-04-26 | Sumitomo Chemical Company, Limited | ジベンゾオキセピノピロール化合物の製造方法、その中間体及び該中間体の製造方法 |
| DE102005059469A1 (de) | 2005-12-13 | 2007-06-14 | Bayer Cropscience Ag | Insektizide Zusammensetzungen mit verbesserter Wirkung |
| DE102006007882A1 (de) | 2006-02-21 | 2007-08-30 | Bayer Cropscience Ag | Cycloalkyl-phenylsubstituierte cyclische Ketoenole |
| DE102006018828A1 (de) * | 2006-04-22 | 2007-10-25 | Bayer Cropscience Ag | Alkoxyalkyl-substituierte cyclische Ketoenole |
| DE102006025874A1 (de) | 2006-06-02 | 2007-12-06 | Bayer Cropscience Ag | Alkoxyalkyl-substituierte cyclische Ketoenole |
| DE102006027731A1 (de) | 2006-06-16 | 2007-12-20 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE102006050148A1 (de) | 2006-10-25 | 2008-04-30 | Bayer Cropscience Ag | Trifluormethoxy-phenylsubstituierte Tetramsäure-Derivate |
| DE102006057037A1 (de) | 2006-12-04 | 2008-06-05 | Bayer Cropscience Ag | cis-Alkoxyspirocyclische biphenylsubstituierte Tetramsäure-Derivate |
| DE102006057036A1 (de) | 2006-12-04 | 2008-06-05 | Bayer Cropscience Ag | Biphenylsubstituierte spirocyclische Ketoenole |
| DE102007009957A1 (de) * | 2006-12-27 | 2008-07-03 | Bayer Cropscience Ag | Verfahren zur verbesserten Nutzung des Produktionsptentials transgener Pflanzen |
| EP2014169A1 (de) | 2007-07-09 | 2009-01-14 | Bayer CropScience AG | Wasserlösliche Konzentrate von 3-(2-Alkoxy-4-chlor-6-alkyl-phenyl)-substituierten Tetramaten und ihren korrespondierenden Enolen |
| EP2020413A1 (de) | 2007-08-02 | 2009-02-04 | Bayer CropScience AG | Oxaspirocyclische-spiro-substituierte Tetram- und Tetronsäure-Derivate |
| EP2039248A1 (de) * | 2007-09-21 | 2009-03-25 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| EP2045240A1 (de) * | 2007-09-25 | 2009-04-08 | Bayer CropScience AG | Halogenalkoxyspirocyclische Tetram- und Tetronsäure-Derivate |
| EP2103615A1 (de) | 2008-03-19 | 2009-09-23 | Bayer CropScience AG | 4'4'-Dioxaspiro-spirocyclisch substituierte Tetramate |
| EP2127522A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| US8846946B2 (en) | 2008-12-02 | 2014-09-30 | Bayer Cropscience Ag | Germinal alkoxy/alkylspirocyclic substituted tetramate derivatives |
| US8389443B2 (en) | 2008-12-02 | 2013-03-05 | Bayer Cropscience Ag | Geminal alkoxy/alkylspirocyclic substituted tetramate derivatives |
| AR075126A1 (es) | 2009-01-29 | 2011-03-09 | Bayer Cropscience Ag | Metodo para el mejor uso del potencial de produccion de plantas transgenicas |
| AU2010223535B2 (en) | 2009-03-11 | 2015-09-10 | Bayer Intellectual Property Gmbh | Halogenalkylmethylenoxy-phenyl-substituted ketoenols |
| DE102009028001A1 (de) | 2009-07-24 | 2011-01-27 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| WO2011098440A2 (de) | 2010-02-10 | 2011-08-18 | Bayer Cropscience Ag | Biphenylsubstituierte cyclische ketoenole |
| EP2534147B1 (de) * | 2010-02-10 | 2015-06-17 | Bayer Intellectual Property GmbH | Spiroheterocyclisch-substituierte tetramsäure-derivate |
| DE102010008642A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
| DE102010008643A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
| DE102010008644A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
| WO2011131623A1 (de) | 2010-04-20 | 2011-10-27 | Bayer Cropscience Ag | Insektizide und/oder herbizide zusammensetzung mit verbesserter wirkung auf basis von spiroheterocyclisch-substituierten tetramsäure-derivaten |
| DE102011011040A1 (de) | 2011-02-08 | 2012-08-09 | Bayer Pharma Aktiengesellschaft | (5s,8s)-3-(4'-Chlor-3'-fluor-4-methylbiphenyl-3-yl)-4-hydroxy-8-methoxy-1-azaspiro[4.5]dec-3-en-2-on (Verbindung A) zur Therapie |
| WO2012110519A1 (de) | 2011-02-17 | 2012-08-23 | Bayer Cropscience Ag | Substituierte 3-(biphenyl-3-yl)-8,8-difluor-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-one zur therapie und halogensubstituierte spirocyclische ketoenole |
| DE102011080405A1 (de) | 2011-08-04 | 2013-02-07 | Bayer Pharma AG | Substituierte 3-(Biphenyl-3-yl)-8,8-difluor-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-one zur Therapie |
| WO2012116960A1 (de) | 2011-03-01 | 2012-09-07 | Bayer Cropscience Ag | 2-acyloxy-pyrrolin-4-one |
| 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 |
| CN103183628B (zh) * | 2011-12-30 | 2015-05-06 | 南京农业大学 | 一种含取代苯肼的吡咯烷-2,4-二酮类化合物、制备方法及应用 |
| UA113753C2 (xx) | 2012-01-26 | 2017-03-10 | Фенілзаміщені кетоеноли для боротьби з паразитами риб | |
| CN104610124A (zh) * | 2015-02-06 | 2015-05-13 | 南京农业大学 | 一种含吡咯烷二酮和苯肼基团的丁酸衍生物、制备方法及应用 |
| AR115088A1 (es) | 2018-05-15 | 2020-11-25 | Bayer Ag | Espirociclohexilpirrolin-2-onas y su uso como herbicidas |
| AR115086A1 (es) | 2018-05-15 | 2020-11-25 | Bayer Ag | Pirrolin-2-onas sustituidas con 2-bromo-6-alcoxifenilo y su uso como herbicidas |
| WO2019219585A1 (de) | 2018-05-15 | 2019-11-21 | Bayer Aktiengesellschaft | Neue 3-(4-alkinyl-6-alkoxy-2-chlorphenyl)-3-pyrrolin-2-one und deren verwendung als herbizide |
| AR115089A1 (es) | 2018-05-15 | 2020-11-25 | Bayer Ag | 2-alquil-6-alcoxifenil-3-pirrolin-2-onas especialmente sustituidas y su uso como herbicidas |
| WO2019228788A1 (de) | 2018-05-29 | 2019-12-05 | Bayer Aktiengesellschaft | 2-brom-6-alkoxyphenyl-substituierte pyrrolin-2-one und deren verwendung als herbizide |
| WO2019228787A1 (de) | 2018-05-29 | 2019-12-05 | Bayer Aktiengesellschaft | Speziell substituierte 2-alkyl-6-alkoxyphenyl-3-pyrrolin-2-one und deren verwendung als herbizide |
| US12053540B2 (en) | 2018-12-04 | 2024-08-06 | Virox Technologies Inc. | Antimicrobial compositions containing solvents including a C3-C5 N-alkyl-gamma-butyrolactam |
| US12052990B2 (en) | 2018-12-04 | 2024-08-06 | Virox Technologies Inc. | C3-C5 n-alkyl-gamma-butyrolactam containing antimicrobial compositions and methods of using same |
| US12532886B2 (en) | 2018-12-04 | 2026-01-27 | Virox Technologies Inc. | Method of killing microbes using C3-C5 n-alkyl-gamma-butyrolactams and antimicrobial compositions containing same |
| BR112021006553A2 (pt) | 2018-12-04 | 2021-07-13 | Virox Technologies Inc. | composições antimicrobianas contendo c3-c5 n-alquil-gama-butirolactama e usos dos mesmos |
| CA3133190A1 (en) | 2019-03-15 | 2020-09-24 | Bayer Aktiengesellschaft | Specifically substituted 3-(2-alkoxy-6-alkyl-4-propinylphenyl)-3-pyrrolin-2-ones and their use as herbicides |
| JP2022524874A (ja) | 2019-03-15 | 2022-05-10 | バイエル アクチェンゲゼルシャフト | 特異的に置換された３－（２－ハロゲン－６－アルキル－４－プロピニルフェニル）－３－ピロリン－２－オンおよび除草剤としてのその使用 |
| EA202192469A1 (ru) | 2019-03-15 | 2022-02-16 | Байер Акциенгезельшафт | 3-(2-бром-4-алкинил-6-алкоксифенил)-замещенные 5-спироциклогексил-3-пирролин-2-оны и их применение в качестве гербицидов |
| EP3938348A1 (de) | 2019-03-15 | 2022-01-19 | Bayer Aktiengesellschaft | Neue 3-(2-brom-4-alkinyl-6-alkoxyphenyl)-3-pyrrolin-2-one und deren verwendung als herbizide |
| EP3938347A1 (de) | 2019-03-15 | 2022-01-19 | Bayer Aktiengesellschaft | Speziell substituierte 3-phenyl-5-spirocyclopentyl-3-pyrrolin-2-one und deren verwendung als herbizide |
| WO2021204884A1 (de) | 2020-04-09 | 2021-10-14 | Bayer Aktiengesellschaft | 3-(4-alkenyl-phenyl)-3-pyrrolin-2-one und deren verwendung als herbizide |
| WO2021209486A1 (de) | 2020-04-15 | 2021-10-21 | Bayer Aktiengesellschaft | Speziell substituierte pyrrolin-2-one und deren verwendung als herbizide |
| TW202210489A (zh) | 2020-05-27 | 2022-03-16 | 德商拜耳廠股份有限公司 | 特定取代之吡咯啉－２－酮及其作為除草劑之用途 |
| WO2023274869A1 (de) | 2021-06-29 | 2023-01-05 | Bayer Aktiengesellschaft | 3-(4-alkenyl-phenyl)-3-pyrrolin-2-one und deren verwendung als herbizide |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3401176A (en) * | 1965-07-27 | 1968-09-10 | American Cyanamid Co | 4-alkoxy or aminoalkoxy-5-phenyl-3-pyrrolin-2-ones and their preparation |
| US4925868A (en) * | 1986-08-29 | 1990-05-15 | Takeda Chemical Industries, Ltd. | 4-Hydroxy-3-pyrrolin-2-ones and treatment of circulatory disorders therewith |
| DE58907411D1 (de) * | 1989-01-07 | 1994-05-11 | Bayer Ag | 3-Aryl-pyrrolidin-2,4-dion-Derivate. |
-
1989
- 1989-12-23 DE DE89123895T patent/DE58907411D1/de not_active Expired - Fee Related
- 1989-12-23 EP EP89123895A patent/EP0377893B1/de not_active Expired - Lifetime
- 1989-12-23 ES ES89123895T patent/ES2063108T3/es not_active Expired - Lifetime
-
1990
- 1990-01-02 US US07/460,208 patent/US5045560A/en not_active Expired - Lifetime
- 1990-01-04 AU AU47649/90A patent/AU620193B2/en not_active Ceased
- 1990-01-05 BR BR909000040A patent/BR9000040A/pt not_active IP Right Cessation
- 1990-01-05 CA CA002007239A patent/CA2007239A1/en not_active Abandoned
- 1990-01-06 JP JP2000906A patent/JP2839167B2/ja not_active Expired - Fee Related
- 1990-01-06 KR KR1019900000102A patent/KR900011726A/ko not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| BR9000040A (pt) | 1990-10-09 |
| EP0377893B1 (de) | 1994-04-06 |
| DE58907411D1 (de) | 1994-05-11 |
| JPH02225459A (ja) | 1990-09-07 |
| EP0377893A3 (de) | 1991-04-24 |
| AU620193B2 (en) | 1992-02-13 |
| JP2839167B2 (ja) | 1998-12-16 |
| AU4764990A (en) | 1990-07-19 |
| EP0377893A2 (de) | 1990-07-18 |
| US5045560A (en) | 1991-09-03 |
| CA2007239A1 (en) | 1990-07-07 |
| ES2063108T3 (es) | 1995-01-01 |
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