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 ester

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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
Application number
DEF18069A
Other languages
German (de)
Inventor
Dr Rudolf Mersch
Dr Gerhard Schrader
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Priority to DEF18069A priority Critical patent/DE961352C/en
Application granted granted Critical
Publication of DE961352C publication Critical patent/DE961352C/en
Expired legal-status Critical Current

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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

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  • 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)

PATENTANSPRUCH: Verfahren zur Herstellung des O, O-Dimethyl-O-(3-nitro-q.-Chlorphenyl)-thiophosphorsäureesters, dadurch gekennzeichnet, daB 3-Nitro-¢-chlorphenol in an sich bekannter Weise mit O, O-Dimethylthiophosphorsäureesterchlorid umgesetzt wird. Claim: Process for the production of O, O-dimethyl-O- (3-nitro-q.-chlorophenyl) -thiophosphoric acid ester, characterized in that 3-nitro- ¢ -chlorophenol reacted in a manner known per se with O, O-dimethylthiophosphoric acid ester chloride will.
DEF18069A 1955-07-30 1955-07-30 Process for the preparation of the O, O-dimethyl-O- (3-nitro-4-chlorophenyl) -thiophosphoric acid ester Expired DE961352C (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (1)

* Cited by examiner, † Cited by third party
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

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