DE961352C - Process for the preparation of the O, O-dimethyl-O- (3-nitro-4-chlorophenyl) -thiophosphoric acid ester - Google Patents
Process for the preparation of the O, O-dimethyl-O- (3-nitro-4-chlorophenyl) -thiophosphoric acid esterInfo
- Publication number
- DE961352C DE961352C DEF18069A DEF0018069A DE961352C DE 961352 C DE961352 C DE 961352C DE F18069 A DEF18069 A DE F18069A DE F0018069 A DEF0018069 A DE F0018069A DE 961352 C DE961352 C DE 961352C
- Authority
- DE
- Germany
- Prior art keywords
- nitro
- acid ester
- dimethyl
- chlorophenyl
- thiophosphoric acid
- 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
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- -1 ester chloride Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000003580 thiophosphoric acid esters Chemical class 0.000 description 3
- JUIKCULGDIZNDI-UHFFFAOYSA-N 4-chloro-3-nitrophenol Chemical compound OC1=CC=C(Cl)C([N+]([O-])=O)=C1 JUIKCULGDIZNDI-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- IOJBNVBZZYSKNG-UHFFFAOYSA-N C[ClH]P(=S)(Cl)[ClH]C Chemical compound C[ClH]P(=S)(Cl)[ClH]C IOJBNVBZZYSKNG-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000563 toxic property Toxicity 0.000 description 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
- C07F9/06—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
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)
Description
Verfahren zur Herstellung des O, O-Dimethyl-O-(3-nitro-4-chlorphenyl)-thiophosphorsäureesters Aus der deutschen Patentschrift gei 87o ist die Herstellung des 0, 0-Dimethyl-0-(q.-nitro-3-chlorphenyl)-thiophosphorsäureesters bekannt.Process for the preparation of the O, O-dimethyl-O- (3-nitro-4-chlorophenyl) -thiophosphoric acid ester The German patent gei 87o describes the production of 0, 0-dimethyl-0- (q.-nitro-3-chlorophenyl) thiophosphoric acid ester known.
Es wurde nun gefunden, daB der isomere 0, 0-Dimethyl-0-(q.-chlor-3-nitrophenyl)-thiophosphorsäureester erheblich bessere Eigenschaften besitzt als die bekannte 4-Nitro-3-chlor-Verbindung. Die neue Verbindung zeichnet sich durch eine verbesserte Pflanzenverträglichkeit der 4-Nitro-3-chlor-Verbindung gegenüber aus. Weiter ist sie hydrolytischen Einflüssen gegenüber erheblich beständiger. Die Giftigkeit der neuen Verbindung ist niedriger, während die biologische Wirkung gleich der Wirkung der 4-Nitro-3-chlor-Verbindung ist. Gegenüber dem bekannten 0, 0-Diäthyl-0-(3-nitro-4.-chlor-phenyl)-thiophosphorsäureester zeichnet sich der neue Dimethylester durch eine fünf- bis zehnfach geringere Toxizität aus.It has now been found that the isomeric 0, 0-dimethyl-0- (q.-chloro-3-nitrophenyl) thiophosphoric acid ester has considerably better properties than the well-known 4-nitro-3-chloro compound. The new compound is characterized by improved plant tolerance the 4-nitro-3-chloro compound compared to. Next it is hydrolytic influences considerably more resistant to. The toxicity of the new compound is lower, while the biological effect is equal to the effect of the 4-nitro-3-chloro compound is. Compared to the known 0, 0-diethyl-0- (3-nitro-4.-chloro-phenyl) -thiophosphoric acid ester the new dimethyl ester is characterized by a five to ten-fold lower toxicity the end.
Die Herstellung des neuen Thiophosphorsäureesters geschieht nach an sich bekannten Methoden durch Reaktion des 0, 0-Dimethylthiophosphorsäureesterchlorids mit 3-Nitro-4-chlorphenol.The preparation of the new thiophosphoric acid ester happens after known methods by reacting the 0, 0-dimethylthiophosphoric acid ester chloride with 3-nitro-4-chlorophenol.
Beispiel iq.o g 4-Chlor-3-nitrophenol werden in i2oo ccm Toluol angeschlämmt. Dazu gibt man i5o g getrocknetes und gesiebtes Kaliumcarbonat, das mit q. g Kupfer vermischt ist. Man erwärmt diese Mischung unter Rühren i/E Stunde auf 85°. Dann tropft man bei dieser Temperatur 177 g Dimethyl-thionophosphorsäurechlorid zu und hält die Temperatur unter weiterem Rühren noch 2 Stunden auf 9o°. Es wird dann auf Zimmertemperatur abgekühlt, die Salze werden abgesaugt, und das Filtrat wird zweimal mit 250 ccm einer 5°/jgen wäBrigen Bicarbonatlösung gewaschen. Man erhält nach dem Abdestillieren des Lösungsmittels 28o g des rohen Esters. Bei o,ot mm destilliert der neue Ester bei i22°.Example iq.og 4-chloro-3-nitrophenol are suspended in i2oo ccm of toluene. To this are added 150 g of dried and sieved potassium carbonate, which is marked with q. g of copper is mixed. This mixture is heated to 85 ° for 1/3 hour while stirring. 177 g of dimethylthionophosphoric acid chloride are then added dropwise at this temperature and the temperature is maintained at 90 ° for a further 2 hours with continued stirring. It is then cooled to room temperature, the salts are filtered off with suction, and the filtrate is washed twice with 250 cc of a 5% aqueous bicarbonate solution. After distilling off the solvent, 28o g of the crude ester are obtained. At o, ot mm, the new ester distills at i22 °.
ToxischeEigenschaftenRatte per os : 500 mg/kg 3/5/5.Toxic properties Rat orally: 500 mg / kg 3/5/5.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF18069A DE961352C (en) | 1955-07-30 | 1955-07-30 | Process for the preparation of the O, O-dimethyl-O- (3-nitro-4-chlorophenyl) -thiophosphoric acid ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF18069A DE961352C (en) | 1955-07-30 | 1955-07-30 | Process for the preparation of the O, O-dimethyl-O- (3-nitro-4-chlorophenyl) -thiophosphoric acid ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE961352C true DE961352C (en) | 1957-04-04 |
Family
ID=7088813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF18069A Expired DE961352C (en) | 1955-07-30 | 1955-07-30 | Process for the preparation of the O, O-dimethyl-O- (3-nitro-4-chlorophenyl) -thiophosphoric acid ester |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE961352C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1212555B (en) * | 1963-02-23 | 1966-03-17 | Bayer Ag | Process for the preparation of a thionophosphoric acid ester |
-
1955
- 1955-07-30 DE DEF18069A patent/DE961352C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1212555B (en) * | 1963-02-23 | 1966-03-17 | Bayer Ag | Process for the preparation of a thionophosphoric acid ester |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2033359A1 (en) | Acylpropanediol (1,3) phosphoric acid mono chohnester and process for their preparation | |
| DE961352C (en) | Process for the preparation of the O, O-dimethyl-O- (3-nitro-4-chlorophenyl) -thiophosphoric acid ester | |
| DE1047776B (en) | Process for the preparation of thionophosphoric acid esters | |
| DE2033357C3 (en) | Palmitoyl-propandioKl 3) -phosphoric acid-S-trimethylaminophenyl ester and process for its preparation | |
| CH395967A (en) | Process for the preparation of racemic and optically active 2,3-dimercaptosuccinic acid | |
| DE921870C (en) | Process for the preparation of 0, 0-dimethyl-0-4-nitro-3-chlorophenyl thiophosphate | |
| DE963872C (en) | Process for the preparation of thiophosphoric acid esters | |
| DE2033361C3 (en) | Acylpropanediol- (13) -phosphoric acid choline ester and process for their preparation | |
| CH414621A (en) | Process for the preparation of phosphonic acid esters | |
| CH369446A (en) | Process for the preparation of thiophosphoric acid esters | |
| AT338255B (en) | PROCESS FOR THE PREPARATION OF NEW 2- (2'-NITROACETYL) -BENZO ACID ESTERS | |
| AT218537B (en) | Process for the production of new phosphonic acid esters | |
| AT222271B (en) | Process for the preparation of new, therapeutically effective sulfonamide complex compounds | |
| DE1245977B (en) | Process for the preparation of 1,3,2-benzodioxaphosphoranes | |
| AT214454B (en) | Process for the preparation of new phosphinic acid derivatives | |
| AT130458B (en) | Process for the preparation of aromatic arsinic acids. | |
| AT210438B (en) | Process for the production of new phosphonic or thiophosphonic acid esters | |
| DE3205456A1 (en) | Halogenated 1-hydroxypyrazoles and processes for their preparation | |
| DE1014105B (en) | Process for the preparation of O, O-dialkyl-thiophosphoric acid triesters | |
| DE1125442B (en) | Process for the production of DL-threonine | |
| CH410949A (en) | Process for the production of phosphonic acid esters or thiophosphonic acid esters | |
| DE1117110B (en) | Process for the preparation of thionophosphoric acid esters | |
| DE1083809B (en) | Process for the preparation of thiolphosphoric acid esters | |
| CH342214A (en) | Process for the preparation of compounds having a fungicidal effect | |
| DEF0018069MA (en) |