GB947156A - Improvements in or relating to processes for the preparation of phosphorus-containing heterocyclic compounds - Google Patents
Improvements in or relating to processes for the preparation of phosphorus-containing heterocyclic compoundsInfo
- Publication number
- GB947156A GB947156A GB597460A GB597460A GB947156A GB 947156 A GB947156 A GB 947156A GB 597460 A GB597460 A GB 597460A GB 597460 A GB597460 A GB 597460A GB 947156 A GB947156 A GB 947156A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxygen
- represent
- sulphur
- compound
- heterocyclic nucleus
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 title abstract 2
- 239000011574 phosphorus Substances 0.000 title abstract 2
- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 7
- 229910052760 oxygen Inorganic materials 0.000 abstract 7
- 239000001301 oxygen Substances 0.000 abstract 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 6
- 239000005864 Sulphur Chemical group 0.000 abstract 6
- 125000000623 heterocyclic group Chemical group 0.000 abstract 6
- 229910052799 carbon Inorganic materials 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 239000011230 binding agent Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 abstract 2
- 125000004122 cyclic group Chemical group 0.000 abstract 2
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- PEQJBOMPGWYIRO-UHFFFAOYSA-N n-ethyl-3,4-dimethoxyaniline Chemical compound CCNC1=CC=C(OC)C(OC)=C1 PEQJBOMPGWYIRO-UHFFFAOYSA-N 0.000 abstract 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- 230000000361 pesticidal effect Effects 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- 150000003512 tertiary amines Chemical class 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- 150000003973 alkyl amines Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 abstract 1
- 229960000956 coumarin Drugs 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 229910052725 zinc 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/6552—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring
-
- 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
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
-
- 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
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/6552—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring
- C07F9/65522—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring condensed with carbocyclic rings or carbocyclic ring systems
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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention comprises compounds of the general formula: <FORM:0947156/C2/1> in which Q is the residue of a compound QH having a cyclic oxygen-containing heterocyclic nucleus including one carbon atom carrying a double-bonded oxygen atom, X1 is oxygen or sulphur, X2 is oxygen or sulphur, R1, R2, R3 and R4 each represent a C1-C6 alkyl group and X1 is bound to a carbon atom in the heterocyclic nucleus of Q. They may be obtained by reacting a compound QX1H preferably in the presence of a halogen hydracid binding agent or a compound QX1M in which Q and X1 are as defined above and M is a metal atom, e.g. Na or K, with a compound of the formula: <FORM:0947156/C2/2> wherein Hlg is a halogen atom preferably Cl and Y1 and Y2 both represent halogen, preferably Cl atoms or represent the groups NR1R2 and NR3R4 respectively wherein R1, R2, R3\t and R4 are as defined above and n is one or zero. When Y1 and Y2 are halogen atoms the resulting product is reacted with an appropriate alkylamine, and when n is zero the tervalent phosphorus is converted to the pentavalent state in the amidated intermediate product by oxidation with hydrogen peroxide if X2 is to represent oxygen or by reaction with elemental sulphur if X2 is to represent sulphur. Specified halogen-hydracid binding agents are amines, especially tertiary amines including pyridine and its homologues, metal salts of weak acids and alkaline compounds of Na, K, Mg, Ca, Ba or Zn. The reaction is preferably carried out in the presence of a solvent, e.g. an aliphatic or aromatic hydrocarbon, an ether, tertiary amine, nitrile, ketone, ester, nitrobenzene or carbon tetrachloride. Q may suitably be the radical of tetronic acid, 1,2-pyrone, 1,4-benzopyrone, 1,2-benzopyrone or 2,3-benzopyrone and the heterocyclic nucleus of Q may be substituted e.g. by alkyl or alkoxy groups. R1, R2, R3 and R4 are preferably methyl groups. The products have pesticidal properties. (see Division A5). Specificacations 713,278 and 940,921 are referred to.ALSO:A pesticidal composition contains as active ingredient a compound of the general formula <FORM:0947156/A5-A6/1> in which Q is the residue of a compound QH having a cyclic oxygen-containing heterocyclic nucleus including one carbon atom carrying a double bonded oxygen atom, X1 is oxygen or sulphur, X2 is oxygen or sulphur, R1, R2, R3 and R4 each represent a C1-C6 alkyl group and X1 is bound to a carbon atom in the heterocyclic nucleus of Q (see Division C2). Q may suitably be the radical of tetronic acid, 1,2-pyrone, or 1,2-, 2,3-, or 1,4-benzopyrone and the heterocyclic nucleus of Q may be substituted, e.g. by alkyl or alkoxy groups. R1, R2, R3 and R4 are preferably methyl groups. The composition may be obtained by the methods disclosed in Specification 940,921. Specification 713,278 also is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL236443 | 1959-02-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB947156A true GB947156A (en) | 1964-01-22 |
Family
ID=19751587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB597460A Expired GB947156A (en) | 1959-02-23 | 1960-02-19 | Improvements in or relating to processes for the preparation of phosphorus-containing heterocyclic compounds |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT219618B (en) |
| BE (1) | BE587903A (en) |
| CH (1) | CH411453A (en) |
| DK (1) | DK96092C (en) |
| FR (1) | FR1288728A (en) |
| GB (1) | GB947156A (en) |
-
1960
- 1960-02-19 GB GB597460A patent/GB947156A/en not_active Expired
- 1960-02-20 DK DK65560A patent/DK96092C/en active
- 1960-02-20 CH CH189660A patent/CH411453A/en unknown
- 1960-02-22 BE BE587903A patent/BE587903A/en unknown
- 1960-02-22 AT AT134160A patent/AT219618B/en active
- 1960-02-23 FR FR819253A patent/FR1288728A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT219618B (en) | 1962-02-12 |
| BE587903A (en) | 1960-08-22 |
| FR1288728A (en) | 1962-03-30 |
| DK96092C (en) | 1963-05-27 |
| CH411453A (en) | 1966-04-15 |
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