KR830006235A - 퀴녹살리닐옥시 에테르의 제조방법 - Google Patents
퀴녹살리닐옥시 에테르의 제조방법 Download PDFInfo
- Publication number
- KR830006235A KR830006235A KR1019810002262A KR810002262A KR830006235A KR 830006235 A KR830006235 A KR 830006235A KR 1019810002262 A KR1019810002262 A KR 1019810002262A KR 810002262 A KR810002262 A KR 810002262A KR 830006235 A KR830006235 A KR 830006235A
- Authority
- KR
- South Korea
- Prior art keywords
- carbon atoms
- alkyl
- formula
- general formula
- och
- Prior art date
Links
- GODNVFJAQGXRLR-UHFFFAOYSA-N 2-quinoxalin-2-yloxyperoxyquinoxaline Chemical compound C1=CC=CC2=NC(OOOC=3N=C4C=CC=CC4=NC=3)=CN=C21 GODNVFJAQGXRLR-UHFFFAOYSA-N 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 15
- 125000000217 alkyl group Chemical group 0.000 claims 10
- -1 alkali metal salt Chemical class 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 229910052783 alkali metal Inorganic materials 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims 3
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 claims 1
- BYHVGQHIAFURIL-UHFFFAOYSA-N 2-chloroquinoxaline Chemical compound C1=CC=CC2=NC(Cl)=CN=C21 BYHVGQHIAFURIL-UHFFFAOYSA-N 0.000 claims 1
- XFFJRQBCOOVRTD-UHFFFAOYSA-N 4-quinoxalin-2-yloxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CN=C(C=CC=C2)C2=N1 XFFJRQBCOOVRTD-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 230000026030 halogenation Effects 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 claims 1
- 230000036571 hydration Effects 0.000 claims 1
- 238000006703 hydration reaction Methods 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 150000002690 malonic acid derivatives Chemical class 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 150000004965 peroxy acids Chemical class 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229920000915 polyvinyl chloride Polymers 0.000 claims 1
- 239000004800 polyvinyl chloride Substances 0.000 claims 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
- 239000012266 salt solution Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
- C07D241/52—Oxygen 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
- 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
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—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
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (1)
- 다음 일반식(a)화합물의 알카리 금속염을 다음 일반식(b)의 2-할로퀴녹살린과 반응시키거나, 다음 일반식(c)의 2-(4-하이드록시페녹시)-퀴녹살린을 다음 일반식(d)의 알킬브로모알케노에이트와 알카리 금속수소화를 존재하에 반응시키거나, 일반식(c)의 알카리 금속염을 다음 일반식(e)의 할로겐화말론산 유도체와 반응시키거나, 다음 일반식(f)의 2-클로로퀴녹살린을 다음 일반식(g)의 알킬 4-(4-하이드록시페녹시)알카노에이트와 반응시키거나, 다음일반식 h의 화합물을 산수용체와 반응시켜 사이클로탈수소 할로겐화한 다음 이어서 하나 또는 그 이상의 다음과 같은 반응을 임의로 수행하는데 즉,1) 염기성 또는 산성 가수분해한 다음 임의로 과량의티오닐클로라이드로 처리한 후, 이어서 임의로 R2및 R3가 H인 일반식 NHR2R3의 아민 2몰과 반응시키고 이어서 임의로 트리플르오로메탄 설포닐클로라이드와 반응시키거나, 적합한 알콜 및 R1이 하기에서 정의된 바와 같은 일반식 R1SH 또는 R1OH인 티올, 페놀 또는 티오페놀과 반응시키거나 또는 R6및 R7이 하기에서 정의된 바와같은 일반식 HN=CR6R7의 옥심과 동몰량의 산수용체 존재하에 반응시키거나(2) 알칼리 또는 알칼리 토금속염, 암모늄염, 아민염과 4급 암모늄염의 용액으로 처리하거나(3) 과산으로 처리하여 Y 또는 Z 또는 둘다 N→O인 화합물을 생성시킴을 특징으로 하여 다음 일반식(I)의 퀴녹살리닐옥시 에테르를 제조하는 방법.상기 일반식에서A는 H 또는 탄소수 1 내지 4의 알킬이고E는 H,Cl,Br,F,CF3,CH3또는 OCH3이고G는 H 또는 Cl이고D는 H,CH3또는 CO2R8이고(일반식(a) 및 (g)에서 D는 H또는 CH3임)L은 H,CH3또는 C2H5이고Q는 -CH=CH-또는 -CH2CH2-이고n은 0 또는 1이고W은 CN 또는 C(0)R 또는이고(일반식(g)에서 W는 CN 또는 COOR1임)W'는 CN 또는 COOR1이고(여기에서 R1은 탄소수 1내지 4의 알킬임)R은 Cl,XR1,NR2R3, OH 또는 OM이고M은 농업적으로 무독한 염이고X는 O 또는 S이고R1은 탄소수 1 내지 18의 알킬, 벤질, 페닐, 탄소수 5내지 8의 사이클로알킬, CH2CH2OCH3,CH2CH2OCH2CH3,CH2CH2CH2OCH3,CH2CH2CH2OCH2CH2OC2H5, -N=CR6R7탄소수 3내지 4의 알케닐, 탄소수 3 내지 4의 알키닐 또는 하나의 Cl로 임의로 치환된 탄소수 3내지 4의 알케닐 또는 알키닐이고(일반식(d) 및 (g)에서 R1은 탄소수 1 내지 4의 알킬임)R2는 수소, 탄소수 1 내지 4의 알킬, 탄소수 5 내지 8의 사이클로알킬, 벤질,OCH3, 탄소수 3 내지 4의 알케닐, -CH2CH2NR4R5,-SO2CF3HOCH2CH2,ClCH2또는 BrCH2CH2이고R3는 H, 또는 탄소수 1내지 4의 알킬 또는R2및 R3는 함께 -(CH2)2-C-(CH2)2-,-(CH2)4-,-(CH2)5-,-(CH2)6- 또는 -(CH2)2-N(CH3)-(CH2)2-가 될 수 있으며R4및 R5는 각각 CH3또는 C2H5이고R6는 H, 탄소수 1내지 4의 알킬 또는 SR9이고R7은 H, 탄소수 1내지 4또는R6및 R7은 함께 -(CH2)4-가 될 수 있으며 -(CH2)5-또는-(CH2)4이고R8및 R9는 각각 탄소수 1내지 4의 알킬이고V는 F,Cl,Br 탄소수 1내지 4의 알콕시, 탄소수 1내지 4의 알킬, CF2,NO2또는 탄소수 1내지 알킬티오이고m은 0,1,2 또는 3이고Y 및 Z은 N 또는 N→O이다.단; (a) D가 CO2R8이면 n은 0이고 L은 CH3이며(b) R1이 -N=CR6R7이면 X는 0이며(c) R6와 R7중 하나는 H가 아이며(d) E가 H 또는 Cl이 아닐 경우 G는 H이며(e) W가 CN 또는이면 A는 H이며(f) E 또는 G가 H가 아닐 경우 A는 또는 CH3이고(g) W가이면 n은 0이고 D는 H이며(h) m가 3이면 V는 Cl,Br,F 또는 CH3이며(i) R2가 SO2CF3이면 R3는 H이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US161,940 | 1980-06-23 | ||
| US06/161,940 US4609396A (en) | 1980-06-23 | 1980-06-23 | Quinoxalinyloxy ethers as selective weed control agents |
| US25013281A | 1981-04-03 | 1981-04-03 | |
| US250,132 | 1981-04-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830006235A true KR830006235A (ko) | 1983-09-20 |
| KR860000321B1 KR860000321B1 (ko) | 1986-04-09 |
Family
ID=26858285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019810002262A KR860000321B1 (ko) | 1980-06-23 | 1981-06-22 | 퀴녹살리닐옥시 에테르의 제조방법 |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0042750B1 (ko) |
| KR (1) | KR860000321B1 (ko) |
| AU (1) | AU7208481A (ko) |
| CA (1) | CA1317299C (ko) |
| ES (1) | ES503307A0 (ko) |
| GR (1) | GR74945B (ko) |
| PH (1) | PH18167A (ko) |
| PL (1) | PL231822A1 (ko) |
| PT (1) | PT73244B (ko) |
| SU (1) | SU1227102A3 (ko) |
| TR (1) | TR21454A (ko) |
| YU (1) | YU43020B (ko) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4655819A (en) * | 1979-07-17 | 1987-04-07 | Ici Australia Limited | Quinoxalinyloxy phenoxy proprionic acid derivatives as selective herbicides |
| US4803273A (en) * | 1979-07-17 | 1989-02-07 | Ici Australia Limited | 2-quinoxalinyloxy phenoxy compounds |
| US5364831A (en) * | 1980-08-06 | 1994-11-15 | Nissan Chemical Industries Ltd. | Quinoxaline derivatives and herbicidal composition |
| IL67463A (en) * | 1981-12-17 | 1985-12-31 | Du Pont | 2-alkoxyethoxyethyl 2-(4-(6-halo-2-quinoxy alinyloxy)phenoxy)propanoates and herbicidal compositions containing them |
| JPS5929604A (ja) * | 1982-08-13 | 1984-02-16 | Nissan Chem Ind Ltd | 水性懸濁除草組成物 |
| US4440930A (en) * | 1982-10-25 | 1984-04-03 | Ppg Industries, Inc. | Herbicidally active quinoline or quinoxaline acetophenone oxime derivatives |
| US4528025A (en) * | 1982-10-25 | 1985-07-09 | Ppg Industries, Inc. | Herbicidally active quinoline or quinoxaline acetophenone oxime derivatives |
| US4464533A (en) * | 1982-11-08 | 1984-08-07 | Ppg Industries, Inc. | Herbicidally active quinoline or quinoxaline benzoate derivatives |
| US4968343A (en) * | 1985-09-16 | 1990-11-06 | The Dow Chemical Company | Fluoroalkyl anilide derivatives of 2-(4-aryloxyphenoxy)alkanoic or alkenoic acids as selective herbicides |
| JPS62190172A (ja) * | 1986-02-14 | 1987-08-20 | Teijin Ltd | フエノキシ脂肪族カルボン酸誘導体および除草剤 |
| ATE70976T1 (de) * | 1987-03-18 | 1992-01-15 | American Home Prod | Sulfonylcarboxamide. |
| US5114464A (en) * | 1990-09-27 | 1992-05-19 | Uniroyal Chemical Company, Inc. | 4-quinoxalinyloxyphenoxyalkylinitrile herbicides |
| DE4042098C2 (de) * | 1990-12-28 | 1993-10-07 | Hoechst Ag | Verfahren zur Herstellung optisch aktiver Chinoxalinyloxy-phenoxypropionsäureester |
| JPH06509357A (ja) * | 1991-08-01 | 1994-10-20 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | 除草剤性のキノキサリニルオキシエーテル類 |
| EP0580932A1 (en) * | 1992-07-29 | 1994-02-02 | E.I. Du Pont De Nemours And Company | Herbicidal quinoxalinyloxy ethers |
| WO1994013647A1 (en) * | 1992-12-15 | 1994-06-23 | The Du Pont Merck Pharmaceutical Company | (2-quinoxalinyloxy)phenoxypropanoic acids and related derivatives as anticancer agents |
| KR100776625B1 (ko) * | 2006-08-20 | 2007-11-16 | 주식회사 나노미 | 도정기 및 이를 이용한 배아미 가공장치 |
| CN103965123B (zh) * | 2013-01-31 | 2016-05-25 | 湖南化工研究院 | 具有生物活性的n-氧基稠杂氧苯氧羧酸酰胺类化合物及其制备方法 |
| CN103086985A (zh) * | 2013-02-01 | 2013-05-08 | 湖南大学 | 2-[4-(喹喔啉-2-基氧基)苯氧基]烷酰胺及其应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2640730C2 (de) * | 1976-09-10 | 1983-08-25 | Hoechst Ag, 6230 Frankfurt | Benzoxazolyloxy- und Benzothiazolyloxy-phenoxy-Verbindungen und diese enthaltende herbizide Mittel |
| CA1247625A (en) * | 1977-07-22 | 1988-12-28 | Howard Johnston | Trifluoromethyl pyridinyloxyphenoxy propanoic acids and propanols and derivatives thereof and methods of herbicidal use |
| GB2026865A (en) * | 1978-03-01 | 1980-02-13 | Ici Ltd | Herbicides |
| JPS6033389B2 (ja) * | 1979-02-22 | 1985-08-02 | 日産化学工業株式会社 | 複素環エ−テル系フェノシキ脂肪酸誘導体、その製造法および該誘導体を含有する除草剤 |
| NZ194196A (en) * | 1979-07-17 | 1983-07-15 | Ici Australia Ltd | -(quinoxalin-2-yl(oxy or thio) phen (oxy or ylthio)-alkanoic acid derivatives or precursors |
| BR8005226A (pt) * | 1979-08-23 | 1981-03-04 | Du Pont | Composto herbicida, composicao e processo para o controle de vegetacao indesejavel, composicao e processo para o controle de er vas gramineas em plantas de folhas grandes e processo para preparar um composto herbicida |
| US4358307A (en) * | 1979-10-02 | 1982-11-09 | Ici Australia Limited | Herbicidal quinoxaline carboxylic acid derivatives |
| EP0045740A1 (en) * | 1980-02-11 | 1982-02-17 | Glyco Chemicals, Inc. | Low temperature bleaching |
| EP0046768A1 (en) * | 1980-02-26 | 1982-03-10 | JOHNSON, Albert Joseph Forest Farm Research Station | An improved skirt hanger |
-
1981
- 1981-06-18 CA CA000380097A patent/CA1317299C/en not_active Expired - Fee Related
- 1981-06-22 PT PT73244A patent/PT73244B/pt unknown
- 1981-06-22 GR GR65309A patent/GR74945B/el unknown
- 1981-06-22 YU YU1555/81A patent/YU43020B/xx unknown
- 1981-06-22 EP EP81302801A patent/EP0042750B1/en not_active Expired
- 1981-06-22 TR TR21454A patent/TR21454A/xx unknown
- 1981-06-22 KR KR1019810002262A patent/KR860000321B1/ko active
- 1981-06-22 PH PH25790A patent/PH18167A/en unknown
- 1981-06-22 SU SU813304452A patent/SU1227102A3/ru active
- 1981-06-23 AU AU72084/81A patent/AU7208481A/en not_active Abandoned
- 1981-06-23 ES ES503307A patent/ES503307A0/es active Granted
- 1981-06-23 PL PL23182281A patent/PL231822A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU7208481A (en) | 1982-01-07 |
| CA1317299C (en) | 1993-05-04 |
| KR860000321B1 (ko) | 1986-04-09 |
| PL231822A1 (ko) | 1982-08-16 |
| ES8303361A1 (es) | 1983-02-01 |
| ES503307A0 (es) | 1983-02-01 |
| YU43020B (en) | 1989-02-28 |
| PH18167A (en) | 1985-04-09 |
| EP0042750B1 (en) | 1986-04-30 |
| PT73244B (en) | 1985-11-12 |
| TR21454A (tr) | 1984-06-06 |
| EP0042750A3 (en) | 1982-01-13 |
| GR74945B (ko) | 1984-07-12 |
| PT73244A (en) | 1981-07-01 |
| SU1227102A3 (ru) | 1986-04-23 |
| EP0042750A2 (en) | 1981-12-30 |
| YU155581A (en) | 1983-10-31 |
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| Publication | Publication Date | Title |
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