KR870001225A - (티오노)포스포르산 에스테르의 제조방법 - Google Patents
(티오노)포스포르산 에스테르의 제조방법 Download PDFInfo
- Publication number
- KR870001225A KR870001225A KR1019860005414A KR860005414A KR870001225A KR 870001225 A KR870001225 A KR 870001225A KR 1019860005414 A KR1019860005414 A KR 1019860005414A KR 860005414 A KR860005414 A KR 860005414A KR 870001225 A KR870001225 A KR 870001225A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- optionally substituted
- pyrimidin
- iii
- formula
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000003014 phosphoric acid esters Chemical class 0.000 title claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 6
- -1 alkaline earth metal salt Chemical class 0.000 claims abstract 6
- 150000001412 amines Chemical class 0.000 claims abstract 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000002619 bicyclic group Chemical group 0.000 claims abstract 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 4
- 239000001301 oxygen Substances 0.000 claims abstract 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 3
- 150000004820 halides Chemical class 0.000 claims abstract 3
- 239000002253 acid Substances 0.000 claims abstract 2
- 239000003054 catalyst Substances 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims abstract 2
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 6
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- 239000000460 chlorine Substances 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 5
- 229910052717 sulfur Chemical group 0.000 claims 5
- 239000011593 sulfur Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims 2
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000012973 diazabicyclooctane Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 하기 일반식(II)의 하이드록실 유도체 또는 이의 적절한 암모늄염, 알칼리금속염 또는 알칼리 토금속염을 촉매로서 비사이클릭 유기 아민의 존재하에 필요시 산 수용체의 존재하에 및 희석제의 존재하에 0 내지 120℃에서 하기 일반식(III)의 (티오노)포스포릭 할라이드와 반응시킴을 특징으로 하여 하기 일반식(I)의 (티오노)포스포르산 에스테르를 제조하는 방법.상기 식에서, X는 산소 또는 황이고, R 및 R1은 동일하거나 상이하며 알킬을 나타내고, R2는 임의로 치환된 아릴이거나 하나 이상의 질소원자를 갖는 임의로 치환된 헤트아릴이며, Hal은 할로겐이다.
- 제1항에 있어서, 일반식(I),(II) 및 (III)에서 X가 산소 또는 황이고, R 및 R1이 동일하거나 상이하며 C1내지 C6알킬을 나타내고, R2가 불소, 염소, 브롬, 니트로, 시아노, C1내지 C4알킬, C1내지 C4알콕시, 페닐 C1내지 C4알킬티오, 할로게노-C1내지 C4알킬, 할로게노-C1내지 C4알콕시, 할로게노-C1내지 C4알킬티오 C1내지 C4알킬-설피닐, C1내지 C4알킬설포닐, C1내지 C2 알킬설피닐 -C1내지 C4알킬, C1내지 C2 알킬설포닐 C1내지 C4알킬 및/또는 C1내지 C4알콕시카보닐에 의해 1 내지 3번 임의로 치환된 페닐; 염소, 브롬, C1내지 C4알킬, C1내지 C4알콕시, C1내지 C4알킬티오, C3내지 C6사이클로알킬, 페닐, 디-(C1내지 C4)알킬아미노, C1내지 C2알콕시 -C1내지 C4알킬, C1내지 C2알킬티오-C1내지 C4알킬, C1내지 C2알킬티오-C1내지 C4알콕시, C1내지 C2-알킬설피닐 -C1내지 C4알킬 및 또는 C1내지 C2알킬설포닐 -C1내지 C4알킬에 의해 1 내지 3번 임의로 치환된 피리미딘 -2-일, 피리미딘-4-일 또는 피리미딘-5-일; C1내지 C4알킬 및 또는 페닐에 의해 1 또는 2번 임의로 치환된 1,2,4-트리아졸-3-일; 및 염소, 브롬 및 또는 할로게노-C1내지 C2알킬에 의해 1 내지 3번 임의로 치환된 피리드-2-일을 나타내고, Hal이 염소를 나타내는 방법.
- 제1항에 있어서, 일반식(I),(II) 및 (III)에서 X가 산소 또는 황이고, R 및 R1이 동하거나 상이하며 C1내지 C4알킬(바람직하게는, 에틸 또는 i-프로필)을 나타내고, R2가 4-니트로페닐, 피리미딘-2-일, 5-브로모-피리미딜-2-일, 5-3-급-부틸-피리미딘-2-일, 2-i-프로필-4-메틸-피리미딘-6-일 또는 2,3,5-트리클로로피리딘-6-일이며, Hal이 염소를 나타내는 방법.
- 제1 내지 3항중 어느 한 항에 있어서, 일반식(I) 및 (III)에서 X가 황인 방법.
- 제1항 내지 3항중 어느 한 항에 있어서, 일반식(I),(II) 및 (III)에서 X가 황이고, R이 에틸이며, R1이 i-프로필이고, R2가 5-3-급-부틸-피리미딘-2-일이며 Hal이 염소인 방법.
- 제1항 내지 5항중 어느 한 항에 있어서, 반응을 20 내지 100℃에서 수행하는 방법.
- 제1항 내지 6항중 어느 한 항에 있어서, 일반식(II)의 하이드록실 화합물 1mole당 0.8 내지 1.5mole의 일반식(III)의 화합물을 사용하는 방법.
- 제1항 내지 7항중 어느 한 항에 있어서, 일반식(II)의 화합물 1mole당 0.005 내지 0.5mole의 비사이클릭 유기아민을 촉매로서 사용하는 방법.
- 제1항 내지 8항중 어느 한 항에 있어서, 비사이클릭 유기아민으로서 1,4-디아자비사이클로-(2,2,2)-옥탄(DABCO)을 사용하는 방법.
- 제1항 내지 9항중 어느 한 항에 있어서, 산수용체로서 탄산칼륨을 사용하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3524055.5 | 1985-07-05 | ||
| DE19853524055 DE3524055A1 (de) | 1985-07-05 | 1985-07-05 | Verfahren zur herstellung von (thiono)phosphorsaeureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR870001225A true KR870001225A (ko) | 1987-03-12 |
Family
ID=6275033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019860005414A KR870001225A (ko) | 1985-07-05 | 1986-07-04 | (티오노)포스포르산 에스테르의 제조방법 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4772702A (ko) |
| EP (1) | EP0207412B1 (ko) |
| JP (1) | JPS6277395A (ko) |
| KR (1) | KR870001225A (ko) |
| AT (1) | ATE51625T1 (ko) |
| BR (1) | BR8603137A (ko) |
| DD (1) | DD248123A5 (ko) |
| DE (2) | DE3524055A1 (ko) |
| DK (1) | DK166543C (ko) |
| HU (1) | HUT42777A (ko) |
| IL (1) | IL79322A (ko) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3524055A1 (de) * | 1985-07-05 | 1987-01-08 | Bayer Ag | Verfahren zur herstellung von (thiono)phosphorsaeureestern |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1525066A (fr) * | 1965-12-18 | 1968-05-17 | Dynamit Nobel Ag | Procédé de préparation d'esters halogénés d'acides phosphoriques |
| US4092312A (en) * | 1975-07-31 | 1978-05-30 | The Dow Chemical Company | Process for preparing phosphorothioates and phenylphosphonothioates |
| JPS5920680B2 (ja) * | 1975-08-04 | 1984-05-15 | ザ ダウ ケミカル カンパニ− | ホスホロチオエ−トまたはフエニルホスホロチオエ−トを製造する方法 |
| NL186814C (nl) * | 1975-08-07 | 1991-03-01 | Dow Chemical Co | Werkwijze ter bereiding van een fosforthioaat of fenylfosfonothioaat. |
| US4357328A (en) * | 1979-10-15 | 1982-11-02 | The Dow Chemical Co. | Heterocyclic substituted triazolyl phosphorous compounds and their use as insecticides |
| DE3524055A1 (de) * | 1985-07-05 | 1987-01-08 | Bayer Ag | Verfahren zur herstellung von (thiono)phosphorsaeureestern |
-
1985
- 1985-07-05 DE DE19853524055 patent/DE3524055A1/de not_active Withdrawn
-
1986
- 1986-06-17 US US06/875,426 patent/US4772702A/en not_active Expired - Fee Related
- 1986-06-23 AT AT86108513T patent/ATE51625T1/de not_active IP Right Cessation
- 1986-06-23 EP EP86108513A patent/EP0207412B1/de not_active Expired - Lifetime
- 1986-06-23 DE DE8686108513T patent/DE3670084D1/de not_active Expired - Lifetime
- 1986-07-01 JP JP61152836A patent/JPS6277395A/ja active Pending
- 1986-07-02 IL IL79322A patent/IL79322A/xx unknown
- 1986-07-04 DD DD86292184A patent/DD248123A5/de not_active IP Right Cessation
- 1986-07-04 HU HU862822A patent/HUT42777A/hu unknown
- 1986-07-04 KR KR1019860005414A patent/KR870001225A/ko not_active Application Discontinuation
- 1986-07-04 DK DK318386A patent/DK166543C/da not_active IP Right Cessation
- 1986-07-04 BR BR8603137A patent/BR8603137A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DD248123A5 (de) | 1987-07-29 |
| EP0207412A2 (de) | 1987-01-07 |
| DE3524055A1 (de) | 1987-01-08 |
| JPS6277395A (ja) | 1987-04-09 |
| DK318386A (da) | 1987-01-06 |
| IL79322A0 (en) | 1986-10-31 |
| DK166543B (da) | 1993-06-07 |
| EP0207412A3 (en) | 1988-08-03 |
| ATE51625T1 (de) | 1990-04-15 |
| HUT42777A (en) | 1987-08-28 |
| DK166543C (da) | 1993-10-25 |
| DE3670084D1 (de) | 1990-05-10 |
| IL79322A (en) | 1990-12-23 |
| US4772702A (en) | 1988-09-20 |
| BR8603137A (pt) | 1987-02-24 |
| EP0207412B1 (de) | 1990-04-04 |
| DK318386D0 (da) | 1986-07-04 |
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