KR910000678A - 신규의 티아졸릴알콕시아크릴레이트, 그의 제조방법, 살진균제로서의 용도 및 중간체 생성물 - Google Patents
신규의 티아졸릴알콕시아크릴레이트, 그의 제조방법, 살진균제로서의 용도 및 중간체 생성물 Download PDFInfo
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- KR910000678A KR910000678A KR1019900008254A KR900008254A KR910000678A KR 910000678 A KR910000678 A KR 910000678A KR 1019900008254 A KR1019900008254 A KR 1019900008254A KR 900008254 A KR900008254 A KR 900008254A KR 910000678 A KR910000678 A KR 910000678A
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- thiazolyl
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- 239000000417 fungicide Substances 0.000 title claims 3
- 238000000034 method Methods 0.000 title claims 3
- 239000013067 intermediate product Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 12
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 6
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 6
- 125000003118 aryl group Chemical group 0.000 claims abstract 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract 4
- 150000002367 halogens Chemical class 0.000 claims abstract 4
- 239000000203 mixture Substances 0.000 claims abstract 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 3
- 125000004104 aryloxy group Chemical group 0.000 claims abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims abstract 2
- 125000005309 thioalkoxy group Chemical group 0.000 claims abstract 2
- 125000005000 thioaryl group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 15
- 125000004432 carbon atom Chemical group C* 0.000 claims 13
- -1 Thiazolyl alkoxy acrylate compound Chemical class 0.000 claims 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- 239000004480 active ingredient Substances 0.000 claims 2
- 230000000855 fungicidal effect Effects 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000006017 1-propenyl group Chemical group 0.000 claims 1
- GPIIIOMWTNQGFI-UHFFFAOYSA-N 2-(1,3-thiazol-4-yl)-1,3-thiazole Chemical compound C1=CSC(C=2N=CSC=2)=N1 GPIIIOMWTNQGFI-UHFFFAOYSA-N 0.000 claims 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- XBECWGJPSXHFCS-UHFFFAOYSA-N imidazole-1-carbaldehyde Chemical compound O=CN1C=CN=C1 XBECWGJPSXHFCS-UHFFFAOYSA-N 0.000 claims 1
- FHAUSBQADNEBFC-AVWDGMTFSA-N methyl (Z)-2-[[(Z)-2-fluoro-3-(1,3-thiazol-4-yl)prop-2-enoyl]-methylamino]-3-methoxyprop-2-enoate Chemical compound COC(/C(=C/OC)/N(C)C(/C(=C/C=1N=CSC=1)/F)=O)=O FHAUSBQADNEBFC-AVWDGMTFSA-N 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- GPTFURBXHJWNHR-UHFFFAOYSA-N protopine Chemical compound C1=C2C(=O)CC3=CC=C4OCOC4=C3CN(C)CCC2=CC2=C1OCO2 GPTFURBXHJWNHR-UHFFFAOYSA-N 0.000 claims 1
- 125000004001 thioalkyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
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- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5456—Arylalkanephosphonium compounds
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- C07—ORGANIC CHEMISTRY
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- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
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- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
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- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
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- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/34—Oxygen atoms
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- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/36—Sulfur atoms
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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Abstract
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Claims (21)
- 하기 일반식(Ⅰ)로 표시되는 티아졸릴알콕시아크릴레이트 화합물.상기 식중, R1및 R2는 서로 동일하거나 또는 상이한 것으로서, 수소원자, 할로겐원자, CF3기, 최대로 8개의 탄소원자를 갖는 알킬기, 알케닐기, 알키닐기 또는 티오알킬기, 최대로 8개의 탄소원자를 갖는 알콕시기, 티오알콕시기 또는 SO2알킬기, 임의로 치환되고 최대로 18개의 탄소원자를 갖는 아릴기, 아릴옥시기 또는 티오아릴기, 임의로 치환된 헤테로아릴기 또는 헤테로아릴옥시기, 또는 임의로 치환된 5원 또는 6원의 헤테로시클릭기를 나타내고, R3는 최대로 8개의 탄소 원자를 갖는 알킬기, 알케닐기 또는 알키닐기, 또는 최대로 18개의 탄소원자를 갖는 아릴기, 또는 최대로 14개의 탄소원자를 갖는 알콕시알콕시알킬기를 나타내고, X는 산소원자, 황원자 또는 NR4기를 나타내고, 여기서 R4는 수소 원자 또는 최대로 8개의 탄소원자를 갖는 알킬기, 알케닐기, 알키닐기, SO2-알킬기, SO2알케닐기 또는 SO2-알키닐기, 또는 임의로 치환되고, 최대로 18개의 탄소원자를 갖는 아릴기 또는 SO2-아릴기를 나타내며, n은 0 또는 1을 나타내고, A는 다음과 같은 기들로 되는 군 중에서 선택된 기이고,여기서, Y는 수소원자, 할로겐원자, CF3기, 최대로 8개의 탄소원자를 갖는 알킬기 또는 알콕시기를 나타내고, Z는 수소원자 또는 할로겐 원자를 나타내며, 이중 결합의 기하학적 구조는 E 또는 Z, 또는 E 및 Z의 혼성 구성이다.
- 제1항에 있어서, 하기의 기에 있어서, CO2CH3와 OR3가 서로에 대하여 트란스 배열인 일반식(Ⅰ)의 화합물.
- 제1항 또는 2항에 있어서, X가 황원자인 일반식(Ⅰ)의 화합물.
- 제1항 내지 3항중 어느 하나의 항에 있어서, A가 하기의 기를 나타내는 일반식(Ⅰ)의 화합물.
- 제4항에 있어서, 이중결합의 기하학적 구조가 E인 일반식(Ⅰ)의 화합물.
- 제1항 내지 3항중 어느 하나의 항에 있어서, A가 하기의 기를 나타내는 일반식(Ⅰ)의 화합물.
- 제1항 내지 3항중 어느 하나의 항에 있어서, A가 하기의 기를 나타내는 일반식(Ⅰ)의 화합물.
- 제7항에 있어서, 이중 결합의 기하학적 구조가 A1기에서 Z이고, A2기에서 E인 일반식(Ⅰ)의 화합물.
- 제1항 내지 6항중 어느 하나의 항에 있어서, n이 0을 나타내는 일반식(Ⅰ)의 화합물.
- 제1항 내지 9항중 어느 하나의 항에 있어서, R1이 수소원자, 염소 원자, 최대로 5개의 탄소원자를 갖는 알킬기 또는 알케닐기, 최대로 5개의 탄소원자를 갖는 알콕시기 또는 하기의 기인 일반식(Ⅰ)인 화합물.
- 제1항 내지 제10항중 어느 하나의 항에 있어서, R2가 수소원자인 일반식(Ⅰ)의 화합물.
- 제1항 내지 9항중 어느 하나의 항에 있어서, R1및 (또는)R2가 임의로 치환된 아릴기인 일반식(Ⅰ)의 화합물.
- 제1항 내지 9항중 어느 하나에 항에 있어서, R1이 SCH3기이고, R2가 CH3기인 일반식(Ⅰ)의 화합물.
- 제12항 또는 13항에 있어서, 알콕시아크릴레이트기가 5번 위치에 존재하는 일반식(Ⅰ)의 화합물.
- 제1항에 있어서, 화합물이 다음과 같은 일반식(Ⅰ)의 화합물, 메틸(E,Z) 3-메톡시-[2-메틸-[1-옥소-3-(4-티아졸릴)-2-프로페닐]-아미노]-2-프로페노에이트, 메틸 2-(2-메틸티오-4-메틸-5-티아졸릴)-3-메톡시-2-프로페노에이트, 메틸 2-[N-[3-[2′-에틸-(2,4′-비티아졸)-4-일]-1-옥소-2-(E)-프로페닐]-메틸]-아미노]-3-(Z)-메톡시 프로페노에이트, 메틸 2-[N-[3-[2′-에틸-(2,4′-비티아졸)-4-일]- -2-(Z)-플루오로프로페닐]메틸아미노]-3-메톡시-(Z)-프로페노에이트, 메틸 (Z,Z)-2-[(2-플루오로-1-옥소-3-(4-티아졸릴)-2-프로페닐)-N-메틸-아미노]-3-메톡시-2-프로페노에이트, 메틸(E,E)-알파-(메톡시 메틸렌)-2-[2-(4-티아졸릴)-에테닐]-벤젠 아세테이트, 메틸 2-(E)-[[[2′-에틸-(2,4′-비티아졸)-4-일]-에테닐]-2-페닐]-3-메톡시-2-(E)-프로페노에이트, 메틸(E,Z)-3-(메톡시-2-[메틸-[1-옥소-3-[2-(트리플루오로메틸)-4-티아졸릴]-2-프로페닐]-아미노]-2-프로페노에이트, 메틸 알파-(메톡시메틸렌)-2-[(2-페닐-4-티아졸릴)-메톡시]-벤젠 아세테이트, 메틸 (E) 2-[[2′-에틸-(2,4′-비티아졸)-4-일]-메톡시-알파-(메톡시메틸렌)-벤젠 아세테이트, 메틸 알파(E)-(메톡시메틸렌)-2-(E)-[[2-(2-펜틸)-4-티아졸릴]-에테닐]-벤젠 아세테이트, 메틸 (E)-알파-(메톡시메틸렌)-2-[(4-티아졸릴-2-메틸에틸]-메톡시]-벤젠 아세테이트, 메틸 E,E-알파-(메톡시메틸렌)-2-[2-(2-메틸에틸-4-티아졸릴)-에테닐]-벤젠 아세테이트, 메틸 E,Z-알파-(메톡시메틸렌)-2-[2-(2-메틸에틸-4-티아졸릴)-에테닐]-벤젠 아세테이트, 메틸 알파 (Z)-(메톡시메틸렌)-2-(E)-[[2-(2-펜틸)-4-티아졸릴]-에테닐]-벤젠 아세테이트, 메틸 알파-(메톡시메틸렌)-2-[(2-메틸-4-티아졸릴)-메톡시]-벤젠 아세테이트.
- 하기 구조식(Ⅱ)(상기 식에서, X,R,R2,A 및 n은 제1항에서 정의한 바와 같음)의 화합물을 강염기 및 알킬 포르메이트 또는 N-포르밀이미다졸과 반응시켜 하기 구조식(Ⅲ)의 화합물을 얻고, 이 화합물을 R3기를 도입시킬 수 있는 시약과 반응시켜서 제1항에서 정의한 일반식(Ⅰ)의 상응하는 화합물을 얻고, 필요에 따라 여러 가지 이성질체들을 분리시킴을 특징으로 하는 상기 일반식(Ⅰ)의 화합물의 제조방법.
- 하기구조식(Ⅳ)(식중 x,R1및 R2는 제1항에서 정의한 바와 같음)의 화합물 또는 그의 관능성 유도체를 하기 구조식(Ⅴ)(식중, R3는 제1항에서 정의한 바와 같고, alK1은 최대로 8개의 탄소원자를 갖는 알킬기를 나타냄)의 화합물과 반응시켜 하기 구조식(Ⅳ)의 화합물을 얻고, 이 화합물을 alk1-OH 알콜 잔기의 제거제와 반응시켜서 하기 일반식(IA)의 상응하는 화합물을 얻는 것을 특징으로 하는, A기가 제7항에서 정의한 A1기를 나타내는 제1항에서 정의한 일반식(Ⅰ)의 화합물의 제조방법.
- 제16항에 있어서, 위티그-호르너 반응에 의해 하기 구조식(Ⅶ)(식중, X,R1및 R2는 제1항에서 정의한 바와 같음)의 화합물을 하기 구조식(Ⅷ)(식중, Y 및 R3는 제1항에서 정의한 바와 같고, alk2및 alk3는 서로 동일하거나 또는 상이한 것으로서, 최대로 8개의 탄소원자를 갖는 알킬기를 나타냄)의 화합물과 반응시켜 하기 구조식(ⅠB)의 상응하는 화합물을 얻고, 필요에 따라서 이 화합물을 단리시키거나, 또는 접촉 수소첨가반응시켜서 하기 일반식(Ⅰc)의 화합물을 얻는 것을 특징으로 하는, A가 하기의 기를 나타내는 일반식(Ⅰ)의 화합물의 제조방법.
- 16항에서 정의한 구조식(Ⅱ) 및 (Ⅲ)의 화합물과 제17항에서 정의한 구조식(Ⅳ) 및 (Ⅵ)의 화합물.
- 유효 성분으로서 제1항 내지 14항중 어느 하나의 항에서 정의된 일반식(Ⅰ)의 화합물을 적어도 1개 이상 함유하는 살진균제 조성물.
- 유효 성분으로서 제15항에 정의된 화합물을 적어도 1개 이상의 함유하는 살진균제 조성물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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FR8907438A FR2647787B1 (fr) | 1989-06-06 | 1989-06-06 | Nouveaux thiazolylalkoxyacrylates, leur procede de preparation, leur application comme fongicides et leurs intermediaires de preparation |
FR89-07438 | 1989-06-06 |
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KR910000678A true KR910000678A (ko) | 1991-01-30 |
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KR1019900008254A KR910000678A (ko) | 1989-06-06 | 1990-06-05 | 신규의 티아졸릴알콕시아크릴레이트, 그의 제조방법, 살진균제로서의 용도 및 중간체 생성물 |
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EP (1) | EP0402246B1 (ko) |
JP (1) | JPH03101669A (ko) |
KR (1) | KR910000678A (ko) |
CN (1) | CN1048386A (ko) |
AT (1) | ATE110374T1 (ko) |
BR (1) | BR9002662A (ko) |
CA (1) | CA2018284A1 (ko) |
DE (1) | DE69011752T2 (ko) |
DK (1) | DK0402246T3 (ko) |
ES (1) | ES2058842T3 (ko) |
FR (3) | FR2647787B1 (ko) |
HU (1) | HU207720B (ko) |
RU (1) | RU2036916C1 (ko) |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
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US5194622A (en) * | 1990-11-21 | 1993-03-16 | Roussel Uclaf | Process for preparation of thiazolylalkoxy acrylates |
EP0489660B1 (fr) * | 1990-12-06 | 1994-11-02 | Roussel-Uclaf | Utilisation de thiazolylalkoxy acrylates pour la fabrication de compositions insecticides et/ou acaricides |
FR2674246B1 (fr) * | 1991-03-21 | 1993-07-09 | Roussel Uclaf | Nouveaux derives de l'acide alpha-methylene 5-thiazolacetique, leur procede de preparation et les intermediaires de ce procede, leur application a titre de fongicides et les compositions les renfermant. |
FR2675142B1 (fr) * | 1991-04-10 | 1993-06-25 | Roussel Uclaf | Nouveaux derives de l'acide alpha-methylene 4-[(phenoxy) methyl] 5-thiazolacetique, leur procede de preparation et les intermediaires de ce procede et leur application a titre de fongicides. |
DE4126994A1 (de) * | 1991-08-16 | 1993-02-18 | Basf Ag | (alpha)-arylacrylsaeurederivate, ihre herstellung und verwendung zur bekaempfung von schaedlingen und pilzen |
FR2682382B1 (fr) * | 1991-10-11 | 1995-04-07 | Roussel Uclaf | Nouveaux derives de l'acide 1-naphtalene acetique, leur procede de preparation et leur application comme pesticides. |
FR2684100B1 (fr) * | 1991-11-26 | 1994-02-18 | Roussel Uclaf | Nouveaux derives de l'acide alpha-methylene 6-styryl acrylique, leur procede de preparation et leur application comme pesticides. |
IT1254198B (it) * | 1992-02-06 | 1995-09-14 | Ministero Dell Uni E Della | Derivati acrilici di 2-tiazolilpirroli ad attivita' fungicida |
JP3217191B2 (ja) * | 1992-07-16 | 2001-10-09 | ビーエーエスエフ アクチェンゲゼルシャフト | ヘテロ芳香族化合物およびこれを含有する植物保護剤 |
AU5118893A (en) * | 1992-10-13 | 1994-05-09 | Nippon Soda Co., Ltd. | Oxazole and thiazole derivatives |
AU2630595A (en) * | 1994-06-09 | 1996-01-04 | Nippon Soda Co., Ltd. | Imidazole derivative, production process, and herbicide |
WO1996038411A1 (de) * | 1995-05-30 | 1996-12-05 | Bayer Aktiengesellschaft | Substituierte carbamide und ihre verwendung als pflanzenschutzmittel, insbesondere als fungizide |
ATE451346T1 (de) * | 1998-03-10 | 2009-12-15 | Ono Pharmaceutical Co | Carbonsäurederivate und medikamente die diese als aktiven wirkstoff enthalten |
KR100392075B1 (ko) * | 2000-09-25 | 2003-07-22 | 한국화학연구원 | 살균효과를 가지는 옥사졸 유도체 |
KR100392074B1 (ko) * | 2000-09-25 | 2003-08-19 | 한국화학연구원 | 살균효과를 가지는 싸이아졸 유도체 |
BRPI0719053B1 (pt) | 2006-09-01 | 2016-09-27 | Dow Agrosciences Llc | inseticidas alquil sulfoximinas (1,3-tiazol 2-substituido) n-substituídas, bem como composição e método para controle de insetos |
EP1939180A1 (en) | 2006-12-20 | 2008-07-02 | sanofi-aventis | Heteroarylacrylamides and their use as pharmaceuticals for the stimulation of the expression of endothelial NO synthase |
GB0712653D0 (en) | 2007-06-28 | 2007-08-08 | Syngenta Ltd | Novel herbicides |
GB0717082D0 (en) | 2007-09-03 | 2007-10-10 | Syngenta Ltd | Novel herbicides |
EP2510787A1 (en) * | 2011-04-15 | 2012-10-17 | Bayer Cropscience AG | Propenoates as fungicides |
CN103130740A (zh) * | 2011-11-29 | 2013-06-05 | 长江大学 | 拌种灵的氨基酸衍生物及其作为杀菌剂的用途 |
CN109627211A (zh) * | 2018-12-24 | 2019-04-16 | 合肥利夫生物科技有限公司 | 一锅法制备啶氧菌酯的方法 |
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NZ213630A (en) * | 1984-10-19 | 1990-02-26 | Ici Plc | Acrylic acid derivatives and fungicidal compositions |
GB8619236D0 (en) * | 1986-08-06 | 1986-09-17 | Ici Plc | Fungicides |
YU47288B (sh) * | 1987-07-11 | 1995-01-31 | Schering Agrochemicals Limited | Akrilatni fungicidi i postupak za njihovo dobijanje |
-
1989
- 1989-06-06 FR FR8907438A patent/FR2647787B1/fr not_active Expired - Fee Related
-
1990
- 1990-06-05 BR BR909002662A patent/BR9002662A/pt not_active Application Discontinuation
- 1990-06-05 CA CA002018284A patent/CA2018284A1/fr not_active Abandoned
- 1990-06-05 KR KR1019900008254A patent/KR910000678A/ko not_active Application Discontinuation
- 1990-06-05 HU HU903483A patent/HU207720B/hu not_active IP Right Cessation
- 1990-06-06 DK DK90401532.8T patent/DK0402246T3/da active
- 1990-06-06 EP EP90401532A patent/EP0402246B1/fr not_active Expired - Lifetime
- 1990-06-06 CN CN90103388A patent/CN1048386A/zh active Pending
- 1990-06-06 JP JP2146387A patent/JPH03101669A/ja active Pending
- 1990-06-06 DE DE69011752T patent/DE69011752T2/de not_active Expired - Fee Related
- 1990-06-06 AT AT90401532T patent/ATE110374T1/de active
- 1990-06-06 ES ES90401532T patent/ES2058842T3/es not_active Expired - Lifetime
- 1990-11-21 FR FR909014496A patent/FR2669334B2/fr not_active Expired - Lifetime
- 1990-12-06 FR FR909015289A patent/FR2670087B1/fr not_active Expired - Fee Related
-
1991
- 1991-10-24 RU SU915001835A patent/RU2036916C1/ru active
Also Published As
Publication number | Publication date |
---|---|
HU903483D0 (en) | 1990-10-28 |
HU207720B (en) | 1993-05-28 |
FR2669334A2 (fr) | 1992-05-22 |
RU2036916C1 (ru) | 1995-06-09 |
DE69011752T2 (de) | 1995-01-12 |
FR2670087A1 (fr) | 1992-06-12 |
JPH03101669A (ja) | 1991-04-26 |
DK0402246T3 (da) | 1994-11-14 |
BR9002662A (pt) | 1991-08-20 |
CA2018284A1 (fr) | 1990-12-06 |
HUT54120A (en) | 1991-01-28 |
DE69011752D1 (de) | 1994-09-29 |
FR2647787A1 (fr) | 1990-12-07 |
CN1048386A (zh) | 1991-01-09 |
EP0402246B1 (fr) | 1994-08-24 |
FR2669334B2 (fr) | 1993-01-15 |
EP0402246A1 (fr) | 1990-12-12 |
FR2647787B1 (fr) | 1991-09-27 |
FR2670087B1 (fr) | 1993-01-15 |
ES2058842T3 (es) | 1994-11-01 |
ATE110374T1 (de) | 1994-09-15 |
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