GB2011417A - Process for the Production of 1,3,4-Thiadiazol-5(4H)-Onyl(4)- Methyl Dithiophosphoric Acid Esters - Google Patents
Process for the Production of 1,3,4-Thiadiazol-5(4H)-Onyl(4)- Methyl Dithiophosphoric Acid EstersInfo
- Publication number
- GB2011417A GB2011417A GB7849803A GB7849803A GB2011417A GB 2011417 A GB2011417 A GB 2011417A GB 7849803 A GB7849803 A GB 7849803A GB 7849803 A GB7849803 A GB 7849803A GB 2011417 A GB2011417 A GB 2011417A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- onyl
- thiadiazol
- methyl
- acid esters
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- MEBQXILRKZHVCX-UHFFFAOYSA-N methidathion Chemical compound COC1=NN(CSP(=S)(OC)OC)C(=O)S1 MEBQXILRKZHVCX-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 abstract 1
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 238000006482 condensation reaction Methods 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 229920002866 paraformaldehyde Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 abstract 1
- 150000003582 thiophosphoric acids Chemical class 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
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6539—Five-membered rings
- C07F9/65392—Five-membered rings containing two nitrogen atoms
- C07F9/65395—Five-membered rings containing two nitrogen atoms having the two nitrogen atoms in positions 1 and 2
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)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Abstract
1,3,4-Thiadiazol-5(4H)-onyl-(4)- methyl dithiophosphoric acid esters are prepared by adding a thiophosphate acid, or an alkali metal or ammonium salt thereof, and 1,2,4-thiadiazole to an aqueous medium consisting essentially of 60- 98 wt.% of sulfuric acid, the amount of sulfuric acid is at least 0.7 mol per mol of free thiophosphoric acid, if free acid is used, and 1.7 per mol of thiophosphoric acid salt; adding paraformaldehyde to this reaction mixture; extracting the acid ester reaction product after the condensation reaction is completed with a solvent, followed by two water washes including neutralization with the last wash; and stripping the solvent and by co-distillation drying the acid ester reaction product and recovering it in melt form. This process is particularly useful in the preparation of O,O-dimethyl-S-[2- methoxy-1,3,4-thiadiazol-5(4H)-onyl- (4)-methyl]dithiophosphate (methidathion).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86546277A | 1977-12-29 | 1977-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2011417A true GB2011417A (en) | 1979-07-11 |
Family
ID=25345564
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7849803A Withdrawn GB2011417A (en) | 1977-12-29 | 1978-12-22 | Process for the Production of 1,3,4-Thiadiazol-5(4H)-Onyl(4)- Methyl Dithiophosphoric Acid Esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2011417A (en) |
-
1978
- 1978-12-22 GB GB7849803A patent/GB2011417A/en not_active Withdrawn
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |