GB2011415A - Process for the Production of Thiophosphoric Acid Esters - Google Patents
Process for the Production of Thiophosphoric Acid EstersInfo
- Publication number
- GB2011415A GB2011415A GB7849246A GB7849246A GB2011415A GB 2011415 A GB2011415 A GB 2011415A GB 7849246 A GB7849246 A GB 7849246A GB 7849246 A GB7849246 A GB 7849246A GB 2011415 A GB2011415 A GB 2011415A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- thiophosphoric acid
- hydroxypyrimidine
- alkenyl
- condensation
- 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.)
- Granted
Links
- 150000003580 thiophosphoric acid esters Chemical class 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 abstract 2
- 159000000000 sodium salts Chemical class 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 230000000895 acaricidal effect Effects 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 abstract 1
- 150000003927 aminopyridines Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 239000003444 phase transfer catalyst Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 150000003581 thiophosphoric acid halides Chemical class 0.000 abstract 1
- 238000007039 two-step reaction Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
-
- 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
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Compounds of formula <IMAGE> (R1 is alkyl, alkenyl, alkoxyalkyl or alkylthioalkyl; R2 is H, alkyl or alkenyl; R3 and R4 are each alkyl) are prepared by reacting an O,O-dialkyl thiophosphoric acid halide with a substituted hydroxypyrimidine in a two-step reaction. In step (a) the hydroxypyrimidine is converted with the aid of sodium hydroxide and in the presence of a hydrocarbon solvent and a phase-transfer catalyst into the sodium salt while drying the reaction mixture by azeotropically removing water. In step (b) condensation of this sodium salt with the dialkyl thiophosphoric halide is carried out at room temperature to about 100 DEG C. The condensation step may be accelerated by addition of 4-bis(C1 to C4alkyl)aminopyridine as catalyst. A product of excellent quality and yield is obtained, and has insecticidal and acaricidal activity.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86509877A | 1977-12-27 | 1977-12-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2011415A true GB2011415A (en) | 1979-07-11 |
| GB2011415B GB2011415B (en) | 1982-06-30 |
Family
ID=25344713
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7849246A Expired GB2011415B (en) | 1977-12-27 | 1978-12-20 | Process for the production of thiophosphoric acid esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2011415B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0015503A1 (en) * | 1979-02-28 | 1980-09-17 | Consortium für elektrochemische Industrie GmbH | Process for preparing diazinone |
| EP0277292A1 (en) * | 1986-12-22 | 1988-08-10 | The Dow Chemical Company | Organic solvent-free process for preparing pyrimidinyl organophosphates |
| CN107011381A (en) * | 2017-04-27 | 2017-08-04 | 湖南化工研究院有限公司 | The control method of objectionable impurities in pirimiphos-methyl synthesis |
-
1978
- 1978-12-20 GB GB7849246A patent/GB2011415B/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0015503A1 (en) * | 1979-02-28 | 1980-09-17 | Consortium für elektrochemische Industrie GmbH | Process for preparing diazinone |
| US4323678A (en) * | 1979-02-28 | 1982-04-06 | Consortium Fur Elektrochemische Ind. Gmbh | Process for the manufacture of diazinon |
| EP0277292A1 (en) * | 1986-12-22 | 1988-08-10 | The Dow Chemical Company | Organic solvent-free process for preparing pyrimidinyl organophosphates |
| CN107011381A (en) * | 2017-04-27 | 2017-08-04 | 湖南化工研究院有限公司 | The control method of objectionable impurities in pirimiphos-methyl synthesis |
| CN107011381B (en) * | 2017-04-27 | 2019-11-22 | 湖南化工研究院有限公司 | The control method of objectionable impurities in pirimiphos-methyl synthesis |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2011415B (en) | 1982-06-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19941220 |