KR910019982A - 시아노퀴놀린 화합물 - Google Patents
시아노퀴놀린 화합물 Download PDFInfo
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- KR910019982A KR910019982A KR1019910007170A KR910007170A KR910019982A KR 910019982 A KR910019982 A KR 910019982A KR 1019910007170 A KR1019910007170 A KR 1019910007170A KR 910007170 A KR910007170 A KR 910007170A KR 910019982 A KR910019982 A KR 910019982A
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- alkyl
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- -1 Cyanoquinoline Compound Chemical class 0.000 title claims 21
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- 150000002431 hydrogen Chemical group 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 claims 4
- 230000002363 herbicidal effect Effects 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- WDXARTMCIRVMAE-UHFFFAOYSA-N quinoline-2-carbonitrile Chemical class C1=CC=CC2=NC(C#N)=CC=C21 WDXARTMCIRVMAE-UHFFFAOYSA-N 0.000 claims 4
- 150000001768 cations Chemical class 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 238000002360 preparation method Methods 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 150000005634 haloquinolines Chemical class 0.000 claims 2
- 239000004009 herbicide Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 229910052709 silver Inorganic materials 0.000 claims 2
- 239000004332 silver Substances 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- UDAIGHZFMLGNDQ-UHFFFAOYSA-N 2-nitroquinoline Chemical compound C1=CC=CC2=NC([N+](=O)[O-])=CC=C21 UDAIGHZFMLGNDQ-UHFFFAOYSA-N 0.000 claims 1
- ZBJJDYGJCNTNTH-UHFFFAOYSA-N Betahistine mesilate Chemical group CS(O)(=O)=O.CS(O)(=O)=O.CNCCC1=CC=CC=N1 ZBJJDYGJCNTNTH-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 230000003042 antagnostic effect Effects 0.000 claims 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 150000001934 cyclohexanes Chemical class 0.000 claims 1
- 239000012039 electrophile Substances 0.000 claims 1
- 230000035784 germination Effects 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 230000008635 plant growth Effects 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 238000009331 sowing Methods 0.000 claims 1
- 238000005507 spraying Methods 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000004962 sulfoxyl group Chemical group 0.000 claims 1
- 229910052717 sulfur Chemical group 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (9)
- 하기 일반식(Ⅰa)또는 (Ⅰb)의 시아노퀴놀린 화합물과, 염기성 질소 치환기 또는 산성 히드록시 치환기를 포함하는 화합물(Ⅰa)과 (Ⅰb)의 농업적으로 사용가능한 염;상기식에서, R1은 CH=C(CN)2;CN=N-N=CH-(5-퀴놀린일);메틸술슐포닐;CH=NOH;할로겐;히드록실;니트로;시아노;시아노,히드록실,카르복실 또는 C1-C4-알콕시 카르보닐에 의해 단일 치환될 수도 있는 C1-C4-알킬티오;롤록리딘일;피페리딘일;르그폴린일;티오모르폴리일;1개 내지 3개의 다음 기: 할로겐 C1-C4-알킬, C1-C4-할로알킬, C1-C4-알콕시, C1-C4-알킬티오, C2-C4-알켄일, 니트로, 아미노, 니트로 C2-C4-알켄일 및/또는 벤질과 치환될 수 있는 페닐, 페녹시, 페닐티오, 페닐디티올일, 페닐술포닐 또는 피롤일이고; m은 0,1,2또는 3이고 m이 2또는 3일때 기들 R1은 다를수도 있고, R2는 수소;히드록실; 할로겐, C1-C4-알콕시; -NR3R4;NR5-CXR6또는 -N=CR7R8이고 R3수소, 또는 1개 내지 5개의 할로겐원자와 치환될수 있고 및/또는 1개의 다음기;히드록실, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬이오, 아미노, C1-C4-아킬아미노 또는 디-C1-C4-알킬아미노와 치완될수도 있는C1-C4-알킬이고; R4는 R3에 대해 규정된 1개의 기;C1-C4-알킬아미노;디-C1-C4-알킬아미노;1개의 다음기; C1-C4-알콕시카르보닐, 1-피롤리딘일 또는 1-이미다졸일과 치환된 C1-C4-알킬;CN-N-(3-시아노-2-퀴놀린일)이고, 또는 R3와 R4는 산소 또는 질소원이 끼어들수도 있는 C4- 또는 C5-알킬렌사슬을 형성하거나(여기서 질소원자는 차례로 C1-C4-알킬 또는 아미노- C1-C4-알킬기와 치환될수 있다). 또는 1개 또는 2개의 R1에 대해 규정된 기 또는 포름일과 치환될 수도 있는 1,3-부타디엔일 사슬을 형성 할수도 있고; R5는 수소 또는 C1-C4-알킬이고; R6은 R5에대해 규정된 1개의 기; 1개의 다음기; C1-C4-알콕시, C1-C4-알킬 카르보닐 또는 C1-C4-알콕시카르보닐과 치환된 C1-C4-알킬; C3-C7-시클로알킬; C1-C4-알콕시카르보닐; 1개 내지 3개의 R1에 대해 구성된 기와 치환될 수도 있는 페닐고리; 아미노; C1-C4-알킬 아미노; 디-C1-C4-알킬 아미노;C3-C7-시클로알킬아미노 또는 페닐아미노이고(여기서 방향족 고리는 1개 내지 3개의 R1에 대해 규정된 기와 치환될 수도 있다); X는 산소 또는 황이며; R7및 R5에 대해 규정된 1개의 기이고; R8은 R6에 대해 규정된 1개의 기이고, 그리고 m이 0일때 R2는 수소, 히드록실 또는 아미노가 아니고 R2가 수소이고 m이 1일때 R1은 메톡시가 아니다.
- 하기 일반식(Ⅱa) 또는 (Ⅱb)의 할로퀴놀린이 하기 일반식(Ⅲ)의 무시 시안화물과 통상적인 방법으로 염기의 존재하에 반응되는 제1항에 따르는 화합물(Ⅰa),또는 (Ⅰb)의 제조방법.상기식에서, M은 1당량의 금속 양이온이다.
- 하기 0-아미노벤즈알데히드(Ⅳ)가 하기 일반식(Ⅴa) 또는(Ⅴb)의 아세토니트릴과 통상적인 방법으로 비활성 유기용매중에서 염기의 존재하에 핵융합 반응되는 R2가 히드록실 또는 아미노인 제1항에 따르는 화합물(Ⅰa)의 제조방법:상기식에서, 일반식(Ⅴb)중의 R은 C1-C4-알킬이다.
- 하기 일반식(Ⅵa)또는 (Ⅵb)니트로퀴놀린이 제3항에 따르는 일반식(Ⅴb)의 아세토니트릴과 비활성 유기 용매중에서 염기의 존재하에 통상적인 방법으로 반응되는 제1항에 따른 화합물(Ⅰa)또는 (Ⅰb)의 제조방법;
- R2가 NH2인 하기 아미노-치환된 시아노퀴놀린 화합물(Ⅰa)또는 (Ⅰb)의 하기 일반식(Ⅶa), (Ⅶb), (Ⅶc)또는 (Ⅷd)의 대응하는 친전자체 또는 하기 키르보닐 화합물(Ⅶ)과 반응되는, R2는 -NH2가 아니고 -NR3R4이거나 또는 -NR5-CHR6또는 -N=CR7R8인 제1항에 따르는 화합물(Ⅰa)또는 (Ⅰb)의 제조방법;상기식에서 R3R4및 R5는 수소가 아니고, Nu1,Nu2,Nu3및 Nu4는 각각 친핵성 이탈기이다.
- 1또는 그 이상의 하기 일반식(ⅠA) 또는 (ⅠB)의 시아노퀴놀린 및 염기성 질소 치환기 또는 산성 히드록실 치환기를 포함하는 일반식(ⅠA) 또는 (ⅠB)의 농업적으로 사용가능 염 및 1또는 그 이상의 하기 일반식(ⅠX)a)2-(4-헤타릴옥시) 또는 2-(4-아릴옥시)-페녹시아세트산유도체와 하기 일반식(Ⅹ)의 b)시클로헥산온 옥심 에테르로 이루어진 기로부터 제초적 성분을 포함하는 제초제;상기식에서, R1과 R2및 지수는 제1항에 규정된 의미를 갖고 나아가 R2는 m이 0일때 수소, 히드록실 또는 아미노민고 R1은 m이 1이고 R2가 수소일때 메톡시이다; a)하기 일반식(ⅠX)의 2-(4-해타릴옥시)-또는2-(4-아릴옥시)-페녹시아세트산 유도체상기식에서, Ra는 페닐고리, 피리딜고리, 벤조옥사질기, 벤조티아졸기 또는 벤조피라진일기 이고 (여기서 방향조 고리계는 2개 이하의 다음기; 할로겐 니트로 C1-C4-알킬, C1-C4-할로알킬 및 C1-C4-할로알콕시와 치환될 수도있다), Rb은 수소, C1-C4-알킬 또는 1당량의 식물에 잘 견디는 양이온이고, Rc는 수소 또는 메틸이다; 및 b)하기 일반식(X)의 시클로헥산온 옥심 에테르상기식에서 Rd는 C1-C4-알킬이고; Re는 할로겐원자와 치환될 수도 있는 C1-C4-알킬, C3- 또는 C4-알켄일, C3- 또는 C4-알킨일 C3- 또는 C4-할로알킬렌 또는 텐일; 1개 내지 3개의 다음기; 할로겐, C1-C4-알킬, C1-C4-알콕시, C1-C4-할로알킬, C1-C4-할로알콕시와 치환될 수도 있는 페닐기와 치환된 C3- 또는 C4-알켄일이고; Rf는 C1-C4-알킬티오 또는 C1-C4-알콕시와 단일 치환 또는 2중 치환될 수도 있는 C1-C4-알킬; 탄소원 이외에 산소 또는 황원자 또는 술폭실 또는 술포닐기를 포함할 수도 있는 5-원 또는 6-원 포화된 또는 단일 포화된 고리계(이 고리는 3개 이하의 다음기;히드록실, 할로겐, C1-C4-알킬, C1-C4-할로알킬, C1-C4-알콕시 및/또는 C1-C4-알킬티오와 치환될 수 있다); 2개의 산소 또는 황원자를 포함하고 3개 이하의 C1-C4-알킬기 및/또는 메톡시기와 치환될 수도 있는 10-원 포화된 또는 단일 포화된 헤테로고리구조; 3개 이하의 다음기; C1-C4-알킬, C1-C4-할로알킬, C1-C4-알콕시 C1-C4-알킬티오, C3-C6-알켄일옥시, C3-C6-알킨일옥시, C1-C4-알콕시 C1-C4-알킬 ,C1-C4-디알콕시-C1-C4-알킬, 포름일, 할로겐 및/또는 벤질아미노와 치환될 수도 있는 페닐, 피리딜, 티아졸일, 피라졸일, 피롤일 또는 이소옥사졸일기이고; Rg는 수소, 히드록실 또는 만약 Rf가 C1-C6-알킬이면, C1-C6-알킬기이고; Rh는 수소, 시아노, 할로겐, C1-C4-알콕시카르보닐 또는 C1-C4-알킬케특심이고 Rf는 수소 또는 1당량의 환경적으로 적합한 양이온이다.
- 제6항에 있어서, 시아노퀴놀린 화합물(ⅠA)또는 (ⅠB)과 제초적 유효성분 a)또는 b)의 중량비가 0.01:1내지 10:1인 것을 특징으로 하는 제초제.
- 제6항에 청구된 바와 같은 일반식(ⅠA)또는 (ⅠB) 시아노퀴놀린과 제6항에 청구된 바와 같은 일반식(ⅠX)의 2-(4-헤타릴옥시)-또는 2-(4-아릴옥시)-페녹시아세트산 유도체 또는 일반식(Ⅹ)의 시클로헥산은 유도체를 작물의 파종전, 동안 또는 후에 또는 작물의 발아전 또는 동안, 동시에 또는 연이어 살포하는 것으로 이루어지는 제거할 식물의 성장을 선택적으로 억제하는 방법.
- 작물의 종자를 제6항에 청구된 바와 같은 일반식(ⅠA)또는 (ⅠB) 시아노퀴놀린의 적대 작용적인 양으로 처리하는 것으로 이루어지는 제6항에 청구된 바와 같은 일반식(ⅠX)의 제초적2-(4-헤타릴옥시)-또는2-(4-아릴옥시)-페녹시아세트산 유도체 또는 일반식(X)의 시클로헥산은 유도체에 의한 작물에 대한 손상 보호 방법※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4014171.3 | 1990-05-03 | ||
| DE4014171A DE4014171A1 (de) | 1990-05-03 | 1990-05-03 | Cyanochinolinverbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR910019982A true KR910019982A (ko) | 1991-12-19 |
Family
ID=6405624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019910007170A KR910019982A (ko) | 1990-05-03 | 1991-05-03 | 시아노퀴놀린 화합물 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5565408A (ko) |
| EP (1) | EP0459140B1 (ko) |
| JP (1) | JPH04225960A (ko) |
| KR (1) | KR910019982A (ko) |
| CA (1) | CA2041684A1 (ko) |
| DE (2) | DE4014171A1 (ko) |
| ES (1) | ES2091258T3 (ko) |
| HU (1) | HU209438B (ko) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4201720A1 (de) * | 1992-01-23 | 1993-07-29 | Basf Ag | Thiochromenonderivate als antidots und sie enthaltende herbizide mittel |
| DE4227896A1 (de) * | 1992-08-22 | 1994-02-24 | Basf Ag | Cyclohexenonoximether, ihre Herstellung und ihre Verwendung |
| JP2000514048A (ja) | 1996-06-20 | 2000-10-24 | ボード オブ リージェンツ，ザ ユニバーシティ オブ テキサス システム | 薬理学的活性調製物を提供するための化合物および方法ならびにそれらの使用 |
| US7157408B2 (en) * | 2003-12-11 | 2007-01-02 | Valent Biosciences Corporation | Quinoline fungicides |
| JP5758801B2 (ja) * | 2008-07-22 | 2015-08-05 | トラスティーズ・オブ・ダートマス・カレッジＴｒｕｓｔｅｅｓ ｏｆ Ｄａｒｔｍｏｕｔｈ Ｃｏｌｌｅｇｅ | 単環式シアノエノンおよびその使用方法説明 |
| EA025568B1 (ru) | 2010-12-17 | 2017-01-30 | Рита Фармасьютикалз, Инк. | Пиразолильные и пиримидинильные трициклические еноны в качестве антиоксидантных модуляторов воспаления |
| WO2014028829A1 (en) | 2012-08-16 | 2014-02-20 | The Scripps Research Institute | Novel kappa opioid ligands |
| EP3662751B1 (en) * | 2015-05-26 | 2021-10-13 | Kaohsiung Medical University | Pyrazolo[4,3-c]quinoline derivatives for inhibition of b-glucuronidase |
| KR102443575B1 (ko) | 2015-07-06 | 2022-09-16 | 길리애드 사이언시즈, 인코포레이티드 | Cot 조정제 및 그의 사용 방법 |
| TWI770527B (zh) | 2019-06-14 | 2022-07-11 | 美商基利科學股份有限公司 | Cot 調節劑及其使用方法 |
| CN114793434A (zh) | 2019-10-18 | 2022-07-26 | 加利福尼亚大学董事会 | 作为用于治疗病原性血管病症的药剂的3-苯基磺酰基-喹啉衍生物 |
| CA3175541A1 (en) | 2020-03-30 | 2021-10-07 | Gilead Sciences, Inc. | Solid forms of (s)-6-(((1-(bicyclo[1.1.1]pentan-1-yl)-1h-1,2,3-triazol-4-yl)2-methyl-1-oxo-1,2- dihydroisoquinolin-5-yl)methyl)))amino)8-chloro-(neopentylamino)quinoline-3-carb onitrile a cot inhibitor compound |
| WO2021202688A1 (en) | 2020-04-02 | 2021-10-07 | Gilead Sciences, Inc. | Process for preparing a cot inhibitor compound |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2507146A (en) * | 1946-03-12 | 1950-05-09 | Eastman Kodak Co | Method of making a 3-halo-2-methylquinoline |
| US2991285A (en) * | 1958-09-09 | 1961-07-04 | Rohm & Haas | Process of cyanation and nitriles produced thereby |
| DE1170955B (de) * | 1961-06-10 | 1964-05-27 | Bayer Ag | Verfahren zur Herstellung von 2-Methylmercapto-3-cyano-4-chlorchinolin |
| GB1207771A (en) * | 1968-03-18 | 1970-10-07 | Warner Lambert Pharmaceutical | Anti-virally active quinoline derivatives |
| LU65139A1 (ko) * | 1972-04-07 | 1973-10-22 | ||
| HU167910B (ko) * | 1972-11-22 | 1976-01-28 | ||
| SE406911B (sv) * | 1973-08-28 | 1979-03-05 | Chinoin Gyogyszer Es Vegyeszet | Sett att framstella nya kinolinderivat |
| DE2363459A1 (de) * | 1973-12-20 | 1975-06-26 | Basf Ag | Neue fluoreszierende chinolinverbindungen |
| US4362876A (en) * | 1978-08-11 | 1982-12-07 | The Sherwin-Williams Company | Preparation of dihydroxyquinoline and certain derivatives |
| US4488898A (en) * | 1978-08-31 | 1984-12-18 | Ciba-Geigy Corporation | Oxime derivatives for protecting plant crops |
| US4490167A (en) * | 1979-08-06 | 1984-12-25 | Ciba-Geigy Corporation | Oxime derivatives of diphenyl ethers and their use in herbicidal compositions |
| US4456468A (en) * | 1980-01-14 | 1984-06-26 | Ciba-Geigy Corporation | Aminoglyoxylonitrile oximiro carbamates for the protection of crops against injury by herbicides |
| US4497651A (en) * | 1982-02-17 | 1985-02-05 | Basf Aktiengesellschaft | Dichloroquinoline derivatives for use as herbicides |
| MA19709A1 (fr) * | 1982-02-17 | 1983-10-01 | Ciba Geigy Ag | Application de derives de quinoleine a la protection des plantes cultivees . |
| ATE13053T1 (de) * | 1982-03-15 | 1985-05-15 | Ciba Geigy Ag | Neue oximaether, verfahren zu ihrer herstellung, mittel die die neuen oximaether enthalten und ihre verwendung. |
| DE3210979A1 (de) * | 1982-03-25 | 1983-09-29 | Basf Ag, 6700 Ludwigshafen | 3-chlor-8-cyano-chinoline, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
| SE8206378L (sv) * | 1982-11-10 | 1984-05-11 | Sverker Hogberg | Nya kelatbildande kinolinforeningar |
| US4496569A (en) * | 1983-03-25 | 1985-01-29 | The Dow Chemical Company | Antiallergic (1H-tetrazol-5-yl)tetrazolo[1,5-a]quinolines and derivatives thereof |
| US4496725A (en) * | 1983-05-23 | 1985-01-29 | The Dow Chemical Company | Substituted 1,2,3-triazino[4',5':4,5]-thieno[2,3-B]quinolin-4(3H)-ones |
| US4540786A (en) * | 1983-08-22 | 1985-09-10 | The Dow Chemical Company | Preparation of 2-chloro-3-cyano-quinolines |
| DE3573511D1 (en) * | 1984-03-15 | 1989-11-16 | Ciba Geigy Ag | Use of quinoline derivatives to protect cultivated plants |
| EP0159290A1 (de) * | 1984-03-28 | 1985-10-23 | Ciba-Geigy Ag | Verwendung von Chinolinderivaten zum Schützen von Kulturpflanzen |
| DE3620856A1 (de) * | 1986-06-21 | 1987-12-23 | Basf Ag | 3-cyanchinolinderivate |
| EP0258184A3 (de) * | 1986-08-13 | 1988-11-30 | Ciba-Geigy Ag | Chinolinderivate als Herbizid- antagonisten für Kulturpflanzen |
| GB8702613D0 (en) * | 1987-02-05 | 1987-03-11 | Ici Plc | Compositions |
| US4920128A (en) * | 1987-07-08 | 1990-04-24 | Sterling Drug Inc. | Pyrazolo[3,4-b]quinolines and their use as antiviral agents |
| US4933447A (en) * | 1987-09-24 | 1990-06-12 | Ss Pharmaceutical Co., Ltd. | Quinoline derivatives |
| GB8727737D0 (en) * | 1987-11-26 | 1987-12-31 | Ici Plc | Antitumour agents |
| IE892088L (en) * | 1988-07-12 | 1990-01-12 | William Henry Deryk Morris | Quinoline derivatives, their production and use |
| DE3829851A1 (de) * | 1988-09-02 | 1990-03-08 | Basf Ag | Tetraazaporphyrine sowie strahlungsempfindliche beschichtungsfilme |
| DE3837926A1 (de) * | 1988-11-09 | 1990-05-17 | Basf Ag | Herbizide mittel, die 2-(4-heteroaryloxy)- oder 2-(4-aryloxy)-phenoxyessig- oder -propionsaeurederivate und/oder cyclohexenonderivate als herbizide wirkstoffe und naphthalinderivate als antidots enthalten, sowie ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
| DE3907938A1 (de) * | 1989-03-11 | 1990-09-13 | Basf Ag | 2,3-substituierte 1,8-naphthyridine, verfahren zu ihrer herstellung und ihre verwendung als antidots |
| US4929128A (en) * | 1989-06-23 | 1990-05-29 | Affleck Robert J | Masonry drill assembly |
-
1990
- 1990-05-03 DE DE4014171A patent/DE4014171A1/de not_active Withdrawn
-
1991
- 1991-04-24 ES ES91106568T patent/ES2091258T3/es not_active Expired - Lifetime
- 1991-04-24 EP EP91106568A patent/EP0459140B1/de not_active Expired - Lifetime
- 1991-04-24 DE DE59108164T patent/DE59108164D1/de not_active Expired - Lifetime
- 1991-04-26 JP JP3096845A patent/JPH04225960A/ja not_active Withdrawn
- 1991-05-02 HU HU911479A patent/HU209438B/hu not_active IP Right Cessation
- 1991-05-02 CA CA002041684A patent/CA2041684A1/en not_active Abandoned
- 1991-05-03 KR KR1019910007170A patent/KR910019982A/ko not_active Application Discontinuation
-
1995
- 1995-04-17 US US08/423,325 patent/US5565408A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0459140B1 (de) | 1996-09-11 |
| EP0459140A2 (de) | 1991-12-04 |
| DE4014171A1 (de) | 1991-11-07 |
| HU911479D0 (en) | 1991-11-28 |
| US5565408A (en) | 1996-10-15 |
| DE59108164D1 (de) | 1996-10-17 |
| CA2041684A1 (en) | 1991-11-04 |
| JPH04225960A (ja) | 1992-08-14 |
| EP0459140A3 (en) | 1992-05-20 |
| HU209438B (en) | 1994-06-28 |
| HUT57539A (en) | 1991-12-30 |
| ES2091258T3 (es) | 1996-11-01 |
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