DE1046062B - Process for the preparation of insecticidally active dialkyl-thionothiolphosphoric acid esters - Google Patents

Process for the preparation of insecticidally active dialkyl-thionothiolphosphoric acid esters

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Publication number
DE1046062B
DE1046062B DEF22472A DEF0022472A DE1046062B DE 1046062 B DE1046062 B DE 1046062B DE F22472 A DEF22472 A DE F22472A DE F0022472 A DEF0022472 A DE F0022472A DE 1046062 B DE1046062 B DE 1046062B
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DE
Germany
Prior art keywords
diethyl
solution
acid
nitrophenyldithiophosphate
mol
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.)
Pending
Application number
DEF22472A
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German (de)
Inventor
Dr Walter Lorenz
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
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Publication date
Application filed by Bayer AG filed Critical Bayer AG
Priority to DEF22472A priority Critical patent/DE1046062B/en
Publication of DE1046062B publication Critical patent/DE1046062B/en
Pending legal-status Critical Current

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    • 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
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/60—Quinoline or hydrogenated quinoline ring systems
    • 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
    • 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
    • A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic 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
    • C07F9/06—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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  • 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)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY

DEUTSCHESGERMAN

KL. 12 qKL. 12 q

INTERNAT. KL. C 07 f '-" INTERNAT. KL. C 07 f '- "

PATENTAMTPATENT OFFICE

AUSLEGESCHRIFT 1046 062EXPLAINING PUBLICATION 1046 062

F 22472 IVb/12 qF 22472 IVb / 12 q

ANMELDETAG: 1.MÄRZ1957REGISTRATION DATE: MARCH 1, 1957

BEKANNTMACHUNG DERANMELDUNG UND AUSGABE DER AUSLEGESCHRIFT: 11. DEZEMBER 1958NOTIFICATION OF REGISTRATION AND EDITION OF THE EDITORIAL: DECEMBER 11, 1958

In der deutschen Patentschrift 1 026 323 wird ein Verfahren zur Herstellung von Thionothiolphosphorsäureestern beschrieben, das dadurch gekennzeichnet ist, daß Dialkylthionophosphorsäurechloride mit Nitrophenylmercaptanen umgesetzt werden. Man erhält hierbei die bisher nicht bekannten 0,0-Dialkyl-S-nitrophenyl-thionothiolphosphorsäureester. German Patent 1,026,323 describes a process for the preparation of thionothiol phosphoric acid esters described, which is characterized in that dialkylthionophosphoric acid chlorides with nitrophenyl mercaptans implemented. This gives the previously unknown 0,0-dialkyl-S-nitrophenyl-thionothiolphosphoric acid esters.

In der deutschen Patentschrift 817 753 wird ferner schon die Herstellung von S-Nitro-phenyl-O.O-dialkylthionophosphaten durch Umsetzung von Nitro- ίο phenylsulfensäurechloriden mit Diestern der phosphorigen Säure schon beschrieben.The German patent 817 753 also describes the production of S-nitro-phenyl-O.O-dialkylthionophosphates by reacting nitro- ίο phenylsulfensäurechloriden with diesters of phosphorous Acid already described.

Es wurde nun gefunden, daß auch Dialkyl-thionophosphite in an sich bekannter Weise mit Nitrophenylsulfensäurechloriden so reagieren, daß insecticid wirksame 0,0 -Dialkyl-S-nitrophenylthionothiolphosphorsäureester erhalten werden. Die Herstellung der genannten Dialkyl thionophosphite ist von Kabachnik und Mastrjukowa (Bull. Acad. Sei. USSR, Div. Chem., 1952, S. 727 bis 735) beschrieben.It has now been found that dialkyl thionophosphites can also be treated with nitrophenylsulfenic acid chlorides in a manner known per se react so that insecticidally effective 0,0 -dialkyl-S-nitrophenylthionothiolphosphoric acid ester can be obtained. The manufacture of the dialkyl thionophosphites mentioned is from Kabachnik and Mastryukova (Bull. Acad. Sci. USSR, Div. Chem., 1952, pp. 727 to 735).

Zur Illustration sei die Reaktion des p-Nitrophenylsulfensäurechlorids mit Diäthylthionophosphit im Formelbild beschrieben, wobei das S-4-Nitrophenyl-O,O-diäthylthionophosphat entsteht:The reaction of p-nitrophenylsulfenic acid chloride is an illustration with diethylthionophosphite described in the formula, the S-4-nitrophenyl-O, O-diethylthionophosphate arises:

Verfahren zur Herstellung von insecticid wirksamen Dialkyl-thionothiol-Process for the production of insecticidally active dialkyl thionothiol

phosphorsäureesternphosphoric acid esters

Anmelder:Applicant:

Farbenfabriken Bayer Aktiengesellschaft, Leverkus en-B ay er werkPaint factories Bayer Aktiengesellschaft, Leverkus en-B ay erwerk

Dr. Walter Lorenz, Wuppertal-Vohwinkel, ist als Erfinder genannt wordenDr. Walter Lorenz, Wuppertal-Vohwinkel, has been named as the inventor

.0C.H,.0C.H,

0„N-0 "N-

S -Cl + HS — P.S -Cl + HS - P.

OC2Hn OC 2 H n

O9N-O 9 N-

— S—P- S-P

OC2H5 OC 2 H 5

OC9H, gegen Warmblüter aus, wie aus der folgenden Gegenüberstellung hervorgeht.OC 9 H, against warm-blooded animals, as can be seen from the following comparison.

Verglichen wurden der erfindungsgemäße Dithiophosphorsäureester (I)The dithiophosphoric acid ester according to the invention (I) were compared

+ HCl -S-P-(OC2HB)2 + HCl -SP- (OC 2 H B ) 2

NO,NO,

Die stark exotherm verlaufenden Umsetzungen werden vorteilhaft in Gegenwart eines geeigneten Lösemittels bei 30 bis 40° C durchgeführt. Als Lösemittel haben sich bewährt: Kohlenwasserstoffe und chlorierte Kohlenwasserstoffe, wie z. B. Benzol, Toluol, Chloroform und Tetrachlorkohlenstoff. Die bei der Reaktion frei werdende Salzsäure kann nachträglich durch Waschen mit Wasser oder durch Zugabe eines Säurebindemittels, wie Pyridin, gebunden werden. Die Verfahrensprodukte fallen praktisch rein an. Eine weitere Reinigung ist meist nicht nötig.The strongly exothermic reactions are advantageous in the presence of a suitable Solvent carried out at 30 to 40 ° C. The following have proven to be solvents: hydrocarbons and chlorinated hydrocarbons, such as. B. benzene, toluene, chloroform and carbon tetrachloride. The at the Hydrochloric acid released from the reaction can be subsequently washed with water or by adding a Acid binder, such as pyridine, are bound. The process products are practically pure. One further cleaning is usually not necessary.

Die erfindungsgemäßen neuen Dithiophosphorsäureester zeichnen sich den aus der deutschen Patentschrift 817 753 her bekannten entsprechenden Monothiophosphorsäureestern sowie den aus der deutschen Patentschrift 885 176 her bekannten ähnlich gebauten Dithiophosphorsäureestern gegenüber durch bessere insecticide Eigenschaften bei niedrigerer Toxizität mit dem aus der deutschen Patentschrift 817 753 her bekannten Ester (II)The new dithiophosphoric acid esters according to the invention are distinguished from the German patent 817 753 ago known corresponding monothiophosphoric acid esters and from the German Patent specification 885 176 ago known similarly constructed dithiophosphoric acid esters compared with better ones Insecticidal properties with lower toxicity with those from German patent 817 753 known ester (II)

-S- P-(OC2H5),-S- P- (OC 2 H 5 ),

NO9 NO 9

und dem aus der deutschen Patentschrift 885 176 her bekannten Ester (III)and the ester (III) known from German patent specification 885 176

C2H5OC 2 H 5 O

C2H5O'C 2 H 5 O '

. -t O \. -t O \

OCH,OCH,

809 698/566809 698/566

Claims (1)

3 43 4 Folgende Werte wurden gefunden:The following values were found: ■ Toxizität Ratte per os T Spinnmilben 0,001% 100%■ Toxicity rat per os T spider mites 0.001% 100% DL95 50 mg/kg Raupen 0,1 % 100%DL 95 50 mg / kg caterpillars 0.1% 100% Toxizität Ratte per os π Spinnmilben 0,01 % 100 %Toxicity rat per os π spider mites 0.01% 100% DL95 2,5 mg/kg Raupen 0,1 % keine WirkungDL 95 2.5 mg / kg caterpillars 0.1% no effect Toxizität Ratte per os jjj Spinnmilben ,. 0,005 % 100 %Toxicity rat per os jjj spider mites,. 0.005% 100% DL95 20 mg/kg Raupen keine WirkungDL 95 20 mg / kg caterpillars no effect Die folgenden Beispiele geben einen Überblick über io tropft man unter Kühlen bei 30 bis 35° C 38 gThe following examples give an overview of io, 38 g are added dropwise with cooling at 30 to 35 ° C das beanspruchte Verfahren: (0,247 Mol) Diäthylthionophosphit zu. Die Lösungthe claimed process: (0.247 moles) diethyl thionophosphite to. The solution . - -i * des Sulfensäurechlorides ist dann völlig entfärbt. Man. - -i * of the sulfenic acid chloride is then completely discolored. Man Beispiel 1 wäscht die Benzolschicht mit Wasser säurefrei,Example 1 washes the benzene layer acid-free with water, O5O-Diäthyl-S-2-nitrophenyldithiophosphat trocknet und destilliert. Das O,O-Diäthyl-S-3-nitro-O 5 O-diethyl-S-2-nitrophenyldithiophosphate is dried and distilled. The O, O-diethyl-S-3-nitro- „ 15 phenyldithiophosphat destilliert bei 0,01 mm/117° C"15 phenyldithiophosphate distilled at 0.01 mm / 117 ° C ■ι OCoH a*s hellgelbes Öl, das nicht kristallisiert. Ausbeute■ ι OCoH a * s light yellow oil that does not crystallize. yield Il / 96% der Theorie.
•S—P(II / 96% of theory.
• S — P ( \ Beispiel 3
OC H\ Example 3
OC H 2 5 so O,O-Diäthyl-S-4-nitrophenyldithiophosphat 2 5 so O, O-diethyl-S-4-nitrophenyldithiophosphate Zu einer Lösung von 38 g (0,2 Mol) 2-Nitrophenyl- n OC2H5
sulfensäurechlorid in 150 ecm Benzol tropft man 32 g J V "■!■>/"
(0,2MoI) Diäthylthionophosphit (Kp11 = SS0C) zu. JSiU2-<^ y— S — P
Die exotherm verlaufende Umsetzung hält man durch 25 OC H
Kühlen mit Wasser auf 30 bis 35° C. Die gelbe ^25
Lösung des 2-Nitrophenylsulfensäurechlorids hellt 31 g (0,1 Mol) 4,4'-Dinitrophenyldisulfid werden in sich dabei immer mehr auf und wird schließlich färb- 150 ecm Methylenchlorid gelöst und bei 25° C mit der los. Nach kurzemNachrühren wäscht man die Benzol- berechneten Menge Chlor in das 4-Nitrophenylsulfenschicht mit Wasser, bis das Waschwasser eben noch 30 säurechlorid übergeführt. Zu dieser orangegelben kongosauer reagiert. Man trocknet und destilliert, Losung tropft man unter Kühlen bei 30 bis 35° C wobei das O,O-Diäthyl-S-2-nitrophenyldithiophosphat 32 g (0,2 Mol) Diäthylthionophosphit Ist die Lösung bei 0,01 mm/106 ° C als blaßgelbes, rasch erstarrendes entfärbt, wäscht man-sie mit Wasser kongoneutral, öl übergeht. Fp. = 32° C. Ausbeute 46 g = 75 % der trocknet sie und destilliert das Lösemittel ab. Der Theorie. 35 Rückstand erstarrt und wird aus wenig Äther umBeispiel 2 kristallisiert. Man erhält 55 g O, O-Diäthyl-S-4-nitro-0,0-Diäthyl-S-3-nitrophenyldithiophosphat phenyldithiophosphat in blaßgelben Kristallen vomTo a solution of 38 g (0.2 mol) of 2-nitrophenyl- n OC 2 H 5
sulfenic acid chloride in 150 ecm benzene is added dropwise 32 g J V "■! ■>/"
(0.2MoI) diethylthionophosphite (bp 11 = SS 0 C). JSiU 2 - <^ y - S - P
The exothermic reaction is maintained at 25 OC H
Cool with water to 30 to 35 ° C. The yellow ^ 25
Solution of 2-nitrophenylsulfenic acid chloride brightens 31 g (0.1 mol) of 4,4'-dinitrophenyl disulfide more and more and is finally dissolved in 150 ecm of methylene chloride and at 25 ° C with the loose. After stirring for a short time, the benzene-calculated amount of chlorine is washed into the 4-nitrophenylsulphene layer with water until the wash water has just transferred acid chloride. To this orange-yellow Congo sour reacts. It is dried and distilled, the solution is added dropwise while cooling at 30 to 35 ° C, the O, O-diethyl-S-2-nitrophenyldithiophosphate 32 g (0.2 mol) of diethylthionophosphite. The solution is at 0.01 mm / 106 ° C as a pale yellow, rapidly solidifying discoloration, it is washed with water in a Congo-neutral manner, oil passes over. Melting point = 32 ° C. Yield 46 g = 75%, which dries them and distills off the solvent. The theory. 35 The residue solidifies and is crystallized around Example 2 from a little ether. 55 g of O, O-diethyl-S-4-nitro-0,0-diethyl-S-3-nitrophenyldithiophosphate phenyldithiophosphate are obtained in pale yellow crystals from ' Fp. = 49 bis 50° C. Ausbeute 89,5 % der Theorie.Melting point = 49 to 50 ° C. Yield 89.5% of theory. υ OC2H5 Patentanspruch:υ OC 2 H 5 claim: ■ S — P Verfahren zur Herstellung von insecticid wirk-■ S - P Process for the production of insecticidally effective r^n τχ ' ' samen Dialkyl-thionothiol-phosphorsäureestern, r ^ n τχ '' seeds dialkyl-thionothiol-phosphoric acid esters, 2 B dadurch gekennzeichnet, daß Dialkylthionophos- 2 B characterized in that dialkylthionophos- 2 phite mit Nitrophenylsulfensäurechloriden, ge-31 g (0,1 Mol) 3,3'-Dinitrodiphenyldisulfid werden 45 gebenenfalls in Gegenwart von Säurebindemitteln, 2 phites with nitrophenylsulfenic acid chlorides, ge-31 g (0.1 mol) of 3,3'-dinitrodiphenyl disulfide are 45 if necessary in the presence of acid binders, in 150 ecm Methylenchlorid gelöst. Unter Kühlen in an sich bekannter Weise umgesetzt werden.dissolved in 150 ecm of methylene chloride. Implemented with cooling in a manner known per se. leitet man die berechnete Menge Chlor ein und läßt the calculated amount of chlorine is introduced and left dabei die Temperatur nicht über 30° C steigen. In die In Betracht gezogene Druckschriften:the temperature does not rise above 30 ° C. In the publications considered: rotgelbe Lösung des 3-Nitrophenylsulfensäurechlorids Deutsche Patentschrift Nr. 817 753.red-yellow solution of 3-nitrophenylsulfenic acid chloride German Patent No. 817 753. © 809 698/566 12.08© 809 698/566 08/12
DEF22472A 1957-03-01 1957-03-01 Process for the preparation of insecticidally active dialkyl-thionothiolphosphoric acid esters Pending DE1046062B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF22472A DE1046062B (en) 1957-03-01 1957-03-01 Process for the preparation of insecticidally active dialkyl-thionothiolphosphoric acid esters

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF22472A DE1046062B (en) 1957-03-01 1957-03-01 Process for the preparation of insecticidally active dialkyl-thionothiolphosphoric acid esters

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1103324B (en) * 1959-10-20 1961-03-30 Bayer Ag Process for the production of sulfenylthiophosphoric acid esters or thiophosphonic acid esters
DE1138394B (en) * 1959-12-08 1962-10-25 Bayer Ag Process for the production of phosphonic acid esters
DE1215171B (en) * 1960-10-05 1966-04-28 Bayer Ag Process for the preparation of dithiophosphoric acid esters

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE817753C (en) * 1949-07-10 1951-10-18 Bayer Ag Process for the preparation of S-nitrophenyl-0, 0-dialkylthiophosphates

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE817753C (en) * 1949-07-10 1951-10-18 Bayer Ag Process for the preparation of S-nitrophenyl-0, 0-dialkylthiophosphates

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1103324B (en) * 1959-10-20 1961-03-30 Bayer Ag Process for the production of sulfenylthiophosphoric acid esters or thiophosphonic acid esters
DE1138394B (en) * 1959-12-08 1962-10-25 Bayer Ag Process for the production of phosphonic acid esters
DE1215171B (en) * 1960-10-05 1966-04-28 Bayer Ag Process for the preparation of dithiophosphoric acid esters

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