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DE1137013B - Process for the preparation of dithiophosphonic acid esters - Google Patents

Process for the preparation of dithiophosphonic acid esters

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Publication number
DE1137013B
DE1137013B DEF31541A DEF0031541A DE1137013B DE 1137013 B DE1137013 B DE 1137013B DE F31541 A DEF31541 A DE F31541A DE F0031541 A DEF0031541 A DE F0031541A DE 1137013 B DE1137013 B DE 1137013B
Authority
DE
Germany
Prior art keywords
ecm
methyl
preparation
acid esters
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
DEF31541A
Other languages
German (de)
Inventor
Dr Reiner Coelln
Dr Walter Lorenz
Dr Hanshelmut Schloer
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
Priority to NL130558D priority Critical patent/NL130558C/xx
Priority to NL266412D priority patent/NL266412A/xx
Priority to BE605593D priority patent/BE605593A/xx
Application filed by Bayer AG filed Critical Bayer AG
Priority to DEF31541A priority patent/DE1137013B/en
Priority to CH725761A priority patent/CH409954A/en
Priority to GB23303/61A priority patent/GB920142A/en
Priority to FR866644A priority patent/FR1294428A/en
Publication of DE1137013B publication Critical patent/DE1137013B/en
Pending legal-status Critical Current

Links

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
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07F9/6533—Six-membered rings
    • 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
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
    • 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
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4075—Esters with hydroxyalkyl compounds
    • 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
    • C07F9/59—Hydrogenated pyridine rings

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)

Description

BUNDESREPUBLIK DEUTSCHLAND KL.12o 26/01FEDERAL REPUBLIC OF GERMANY KL.12o 26/01

INTERNAT. KL. C 07 fINTERNAT. KL. C 07 f

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

AUSLEGESCHRIFT 1137 013EXPLAINING EDITORIAL 1137 013

F 31541 IVb/12 οF 31541 IVb / 12 ο

ANMELDETAG: 39. JUNI 1960 REGISTRATION DATE: JUNE 39, 1960

BEKANNTMACHUNG DER ANMELDUNG UNDAUSGABE DE» AUSLEGESCHRIFT: 27. SEPTEMBER 1962 NOTICE OF NOTIFICATION AND ISSUE DE »EDITORIAL: SEPTEMBER 27, 1962

Die Erfindung betrifft ein Verfahren zur Herstellung von Dithiophosphonsäureestern der allgemeinen FormelThe invention relates to a process for the preparation of dithiophosphonic esters of the general formula

R1 R 1

S OR2
II/
P
\S OR 2
II /
P.
\ CHCH — CO-- CO- /
N
\/
N
\ R4 R 4 \
s — \
s - R3 R 3 \
R5 \
R 5

In vorgenannter Formel steht Ri für einen niederen Alkylrest und R2 für einen Alkylrest mit 1 bis 8 Kohlenstoffatomen, während R3 Wasserstoff bzw. den Methyl-, Äthyl- oder Propylrest bedeutet und R4 und R5 Wasserstoff oder Alkylreste darstellen.In the above formula, Ri represents a lower alkyl radical and R 2 represents an alkyl radical having 1 to 8 carbon atoms, while R 3 represents hydrogen or the methyl, ethyl or propyl radical and R4 and R5 represent hydrogen or alkyl radicals.

Die erfindungsgemäßen Dithiophosphonsäureester werden erhalten, wenn man alkyl-O-alkylthionothiolphosphonsaure Salze der allgemeinen FormelThe dithiophosphonic acid esters according to the invention are obtained when using alkyl-O-alkylthionothiolphosphonic acid Salts of the general formula

R,R,

S OR2 S OR 2

II/
ρ II /
ρ

SMeSMe

Verfahren zur Herstellung von DithiophosphonsäureesternProcess for the preparation of dithiophosphonic acid esters

Anmelder:Applicant:

Farbenfabriken Bayer Aktiengesellschaft, LeverkusenPaint factories Bayer Aktiengesellschaft, Leverkusen

Dr. Reiner Colin, Wuppertal-Elberfeld,Dr. Reiner Colin, Wuppertal-Elberfeld,

Dr. Walter Lorenz, Wuppertal-Vohwinkel,Dr. Walter Lorenz, Wuppertal-Vohwinkel,

und Dr. Hanshelmut Schlör, Wuppertal-Barmen, sind als Erfinder genannt wordenand Dr. Hanshelmut Schlör, Wuppertal-Barmen, have been named as inventors

nach prinzipell bekannten Methoden mit α-Halogen- umsetzt, wobei in den letztgenannten Formeln alkancarbonamiden der Formel die Reste Rj bis R5 die weiter oben angegebeneis reacted according to known methods prinzipell with α-halogen, where, in the last-mentioned formulas, the formula alkancarbonamiden the radicals R j to R 5 indicated further above

30 Bedeutung haben, während Hai für ein Halogenatom R4 steht und Me ein Alkalimetall oder die Ammonium-30 have meaning, while Hai stands for a halogen atom R4 and Me an alkali metal or the ammonium

/ gruppe bedeutet. / group means.

Hai — CH — CO — N Der Verlauf der verfahrensgemäßen UmsetzungHai - CH - CO - N The course of the procedural implementation

I \ sei an Hand des nachfolgenden FormelschemasI \ sei on the basis of the following formula scheme

R3 R5 35 näher erläutert:R 3 R 5 35 explained in more detail:

S OR2 R4 S OR 2 R 4

II/ /II / /

Ri-P + Hal —CH-CO —NRi-P + Hal -CH-CO -N

SMe R3 R5 SMe R 3 R 5

►R, — P►R, - P

S OR2 S OR 2

II/II /

R4 + MeHaIR 4 + MeHaI

S —CH-CO —NS —CH-CO —N

R3 R 3

Die erfindungsgemäße Reaktion wird bevorzugt 50 Vervollständigung der Umsetzung notwendig ist, in inerten organischen Lösungsmitteln bzw. in das Reaktionsgemisch kurze Zeit auf leicht erhöhte wäßrigem Medium durchgeführt, wobei es zur Temperatur zu erwärmen.The reaction according to the invention is preferably 50 completion of the reaction is necessary in inert organic solvents or in the reaction mixture for a short time to slightly increased aqueous medium carried out, heating it to temperature.

209 658/424209 658/424

Den erfindungsgemäßen Verbindungen entsprechende Dithiophosphorsäureester sind bereits in der Literatur beschrieben. Im Vergleich zu diesen bekannten Produkten analoger Zusammensetzung zeichnen sich die gemäß vorliegender Erfindung erhältlichen Substanzen durch wesentlich bessere insektizide Eigenschaften aus. Vor allem besitzen die erfindungsgemäßen Verbindungen eine sehr guteDithiophosphoric acid esters corresponding to the compounds according to the invention are already available described in the literature. Compared to these known products of an analogous composition the substances obtainable according to the present invention are distinguished by significantly better ones insecticidal properties. Above all, the compounds according to the invention have a very good one

Wirkung gegenüber solchen Schadinsekten, die gegen die aus der zitierten Patentschrift bekannten Dithiophosphorsäureester Resistenzerscheinungen zeigen. Diese technische Überlegenheit der Verfahrensprodukte geht aus den im folgenden tabellarisch zusammengestellten Ergebnissen von Vergleichsversuchen hervor:Effect on such harmful insects, those known from the patent cited Dithiophosphoric acid ester show signs of resistance. This technical superiority of the process products is based on the results of comparative tests compiled in the following table emerge:

VergleichsversucheComparative experiments

Verbindung
Nr.link
No. Konstitutionconstitution CH3OCH 3 O Anwendung
gegenuse
against 11 Q\i
P-S-CH2-CO-NH-CH3
C2H5O Q \ i
PS-CH 2 -CO-NH-CH 3
C 2 H 5 O (erfindungsgemäß, Beispiel 3)(according to the invention, example 3) Blattläuse
SpinnmilbenAphids
Spider mites (erfindungsgemäß, Beispiel 2)(according to the invention, example 2) SS. SS. (CH3O2) — P — S — CH2 — CO — NH2 (CH 3 O 2 ) - P - S - CH 2 - CO - NH 2 22 (C2H5O)2 — P — S — CH2 — CO — NH6CH5 (C 2 H 5 O) 2 - P - S - CH 2 - CO - NH 6 CH 5 (bekannt aus deutscher Patentschrift 819 998)(known from German patent specification 819 998) BlattläuseAphids (bekannt aus deutscher Patentschrift 819 998,
Beispiel 2)(known from German patent specification 819 998,
Example 2) CH3 SCH 3 S SpinnmilbenSpider mites CH3 S .CH 3 S. P-S-CH2-CO-NH-CH3
CH3OPS-CH 2 -CO-NH-CH 3
CH 3 O 33 P-S-CH2-CO-NH2 PS-CH 2 -CO-NH 2 (erfindungsgemäß, Beispiel 4)(according to the invention, example 4) BlattläuseAphids SS. (C2H5O)2 — P — S — CH2 — CO — NHCH3 (C 2 H 5 O) 2 - P - S - CH 2 - CO - NHCH 3 (bekannt aus deutscher Patentschrift 819 998,
Beispiel 1)(known from German patent specification 819 998,
Example 1) 44th CH3 SCH 3 S BlattläuseAphids P-S-CH2-CONH2
C2H5OPS-CH 2 -CONH 2
C 2 H 5 O SpinnmilbenSpider mites (erfindungsgemäß, Beispiel 1)(according to the invention, example 1) 55 Blattläuse
SpinnmilbenAphids
Spider mites 66th BlattläuseAphids SpinnmilbenSpider mites 77th Blattläuse
SpinnmilbenAphids
Spider mites

Wirkstoffkonzentration Active ingredient concentration

0,001
0,00010.001
0.0001

0,1
0,10.1
0.1

0,0010.001

0,001
0,010.001
0.01

0,001
0,0010.001
0.001

0,001
0,10.001
0.1

0,001
0,00010.001
0.0001

AbtötungMortification

der Schädlingethe pests

in o/o in o / o

100 100100 100

0 00 0

100100

0 500 50

100 100100 100

0 800 80

80 10080 100

Auf Grund ihrer hervorragenden Insektiziden
Wirksamkeit werden d';s Verfahrensprodukte als
Schädlingsbekämpfungsmittel besonders im Pflanzenschutz eingesetzt.Because of their excellent insecticides
Effectiveness will be d '; s process products as
Pesticides used especially in crop protection.

Die Anwendung der erfindungsgemäßen Verbindungen für den genannten Zweck geschieht auf prinzipiell bekannte Weise, d. h. bevorzugt in Kombination mit geeigneten festen oder flüssigenThe compounds according to the invention are used for the stated purpose in principle known way, d. H. preferably in combination with suitable solid or liquid

Streck- bzw. Verdünnungsmitteln, vor allem in Form wäßriger Emulsionen, gegebenenfalls unter Mitverwendung handelsüblicher Emulgatoren.Extenders or diluents, especially in the form of aqueous emulsions, optionally under Use of commercially available emulsifiers.

Die folgenden Beispiele vermitteln einen Überblick über das beanspruchte Verfahren:The following examples provide an overview of the claimed method:

CH3 SCH 3 S

C2H5OC 2 H 5 O

Beispiel 1example 1

P-S-CH2-CO NH-CH3 PS-CH 2 -CO NH-CH 3

Beispiel 2Example 2

C2H5 SC 2 H 5 S

P — S · CH2 · CO · NH · CH3 P - S • CH 2 • CO • NH • CH 3

C2H5OC 2 H 5 O

30 g (0,2 Mol) Bromessigsäuremonomethylamid und 46 g (0,22 Mol) des Kaliumsalzes der Äthylthionophosphon-O-äthyk .ter-thiolsäure werden in 70 ecm Wasser gelöst. Man erwärmt 1 Stunde auf 50 bis 60° C. Nach Erkalten wird das Öl in Benzol aufgenommen, mit Wasser und Natriumbikarbonatlösung gewaschen und über Natriumsulfat getrocknet. Nach Abdestillieren des Lösungsmittels hinterbleiben 40 g des neuen Esters als hellgelbes Öl. Ausbeute 83% der Theorie.30 g (0.2 mol) of bromoacetic acid monomethylamide and 46 g (0.22 mol) of the potassium salt of ethylthionophosphon-O-ethy .ter-thiol acid are dissolved in 70 ecm of water. The mixture is warmed up for 1 hour 50 to 60 ° C. After cooling, the oil is taken up in benzene, with water and sodium bicarbonate solution washed and dried over sodium sulfate. Remain after distilling off the solvent 40 g of the new ester as a light yellow oil. Yield 83% of theory.

Mol 241,3:Mol 241.3:

Berechnet N 5,81%, S 26,57<y0, P 12,840/0;Calculated N 5.81%, S 26.57 <y 0 , P 12.840 / 0 ;

gefunden N 5,93<>/0, S 26,53< >/0, P 12,86<y0.found N 5.93 <> / 0 , S 26.53 <> / 0 , P 12.86 <y 0 .

DL50 Ratte per os 2,5 mg/kg.DL 50 rat orally 2.5 mg / kg.

Beispiel 3Example 3

CH3OCH 3 O

■ S · CH2 · CO · NH2 ■ S · CH 2 · CO · NH 2

Beispiel 4
CH3 SExample 4
CH 3 S

\ll\ ll

P-S-CH2-CO NH-CH3
CH3OPS-CH 2 -CO NH-CH 3
CH 3 O

30 g (0,2 Mol) Bromessigsäuremonomethylamid und 36 g (0,22 Mol) des Kaliumsalzes der Methylthionophosphon-O-äthylester-thiolsäure werden in 70 ecm Wasser gelöst und 1 Stunde auf 50° C erwärmt. Das erhaltene Öl kristallisiert beim Erkalten. Aus Benzol—Petroläther erhält man Kristalle vom Fp. 65° C. Ausbeute 31 g (68,5% der Theorie).30 g (0.2 mol) of bromoacetic acid monomethylamide and 36 g (0.22 mol) of the potassium salt of methylthionophosphono-O-ethyl ester thiolic acid are dissolved in 70 ecm of water and heated to 50 ° C for 1 hour. The oil obtained crystallizes on cooling. Crystals with a melting point of 65 ° C. are obtained from benzene petroleum ether. Yield 31 g (68.5% of theory).

Mol 227,3:Mol 227.3:

Berechnet N 6,16<>/0, S 28,21 o/o;Calculated N 6.16 / 0 , S 28.21 o / o ;

gefunden N 6,39%, S 28,01<>/0.found N 6.39%, S 28.01 <> / 0 .

Die DL5Q an der Ratte per os beträgt 2,5 mg/kg.The DL 5 Q in the rat per os is 2.5 mg / kg.

ίο 36 g (0,2 Mol) methyl-thionophosphon-O-methylester-thiolsaures Kalium werden in 100 ecm Acetonitril gelöst. Dazu gibt man unter Rühren 30 g Bromessigsäuremonomethylamid. Man erwärmt 1 Stunde auf 50 bis 60° C und arbeitet dann wieίο 36 g (0.2 mol) methyl-thionophosphon-O-methylester-thiolic acid Potassium are dissolved in 100 ecm acetonitrile. To this, 30 g are added with stirring Bromoacetic acid monomethylamide. The mixture is heated to 50 to 60 ° C for 1 hour and then works as

is im Beispiel 1 auf. Es werden auf diese Weise 34 g des neuen Esters in Form eines gelblichen, viskosen Öles erhalten. Ausbeute 80% der Theorie.is shown in example 1. In this way 34 g of the new ester obtained in the form of a yellowish, viscous oil. Yield 80% of theory.

Mol 213:Mol 213:

zo Berechnet P 14,53 %, N 6,57<y0;zo calculates P 14.53 %, N 6.57 <y 0 ;

gefunden P 13,9%, N 6,50/0.found P 13.9%, N 6.50 / 0 .

DL50 Ratte per os 10 mg/kg.DL 50 rat orally 10 mg / kg.

Beispiel 5Example 5

C2H5O S CH3 C 2 H 5 OS CH 3

P-S-CH-CO-NH-CH3 PS-CH-CO-NH-CH 3

CH3 CH 3

59 g (0,33MoI) Kaliumsalz des Methyldithiophosphonsäureäthylesters und 50 g (0,3 Mol) (dl)-a-Brompropionsäuremonomethylamid (Κρ.χ 88 bis 900C; Fp. 410C) werden in 200 ecm Wasser gelöst und 15 Minuten auf 900C erwärmt. Das dabei ausgeschiedene Öl wird in Benzol aufgenommen, zunächst mit Wasser und kurz mit Natriumbicarbonatlösung gewaschen. Nach dem Trocknen über Natriumsulfat destilliert man das Lösungsmittel ab. Der Rückstand erstarrt rasch beim Erkalten. Fp. 62° C. Ausbeute 60 g (83,3 o/o der Theorie).59 g (0.33MoI) potassium salt of methyldithiophosphonic acid ethyl ester and 50 g (0.3 mol) (dl) -a-bromopropionic acid monomethylamide (Κρ.χ 88 to 90 0 C; mp. 41 0 C) are dissolved in 200 ecm of water and 15 Heated to 90 0 C minutes. The oil which separates out is taken up in benzene and washed first with water and briefly with sodium bicarbonate solution. After drying over sodium sulfate, the solvent is distilled off. The residue solidifies quickly when it cools. Mp. 62 ° C. Yield 60 g (83.3 o / o of theory).

Mol 241,3:Mol 241.3:

Berechnet N 5,8io/o, S 26,57%, P 12,84°/0;Calculated N 5,8io / o, S 26.57%, P 12.84 ° / 0;

gefunden N 5,91%, S 26,44<V0, P 12,53O/o.found N 5.91%, S 26.44 <V 0 , P 12.53O / o .

3535

4040

4545

Claims (1)

PATENTANSPRUCH:PATENT CLAIM: Verfahren zur Herstellung von Dithiophosphonsäureestern, dadurch gekennzeichnet, daß man alkyl-O-alkylthionothiolphosphonsaure Salze der allgemeinen FormelProcess for the preparation of dithiophosphonic acid esters, characterized in that one uses alkyl-O-alkylthionothiolphosphonic acid salts of the general formula 5555 45 g (0,25 Mol) methyl-thionophosphon-O-methylester-thiolsaures Kalium werden in 100 ecm Acetonitril gelöst. Dazu gibt man unter Rühren 23,4 g Chloracetamid und hält 1 Stunde bei 60° C. Das Reaktionsprodukt wird in 100 ecm Eiswasser gegeben und mit 300 ecm Benzol aufgenommen. Die benzolische Lösung wird mit Natriumsulfat getrocknet. Beim Abdestillieren des Lösemittels hinterbleiben 23 g des neuen Esters als farbloses Öl, das nach kurzer Zeit kristallin erstarrt.45 g (0.25 mol) of methyl thionophosphonic O-methyl ester thiolic acid Potassium are dissolved in 100 ecm acetonitrile. 23.4 g are added with stirring Chloracetamide and holds at 60 ° C. for 1 hour. The reaction product is poured into 100 ecm of ice water and taken up with 300 ecm benzene. The benzene solution is dried with sodium sulfate. When the solvent is distilled off, 23 g of the new ester remain as a colorless oil, the solidified in crystalline form after a short time. DL50 Ratte per os 10 mg/kg.DL 50 rat orally 10 mg / kg. R1-PR 1 -P S OR2 S OR 2 II/II / SMeSMe in der R1 für einen niederen Alkylrest und R2 für einen Alkylrest mit 1 bis 8 Kohlenstoffatomen steht, während Me ein Alkalimetall oder die Ammoniumgruppe bedeutet, mit a-Halogenalkancarbonsäureamiden der allgemeinen Formelin which R 1 is a lower alkyl radical and R 2 is an alkyl radical having 1 to 8 carbon atoms, while Me is an alkali metal or the ammonium group, with α-haloalkanecarboxamides of the general formula 7 87 8 R4 S OR2 R 4 S OR 2 / II// II / Hal —CH-CP-N R1-P R4 Hal -CH-CP-N R 1 -PR 4 R3 R5 5 s —CH-CO —NR 3 R 5 5 s —CH — CO —N R3 R5 R 3 R 5 worin R3 für Wasserstoff bzw. den Methyl-, umsetzt, wobei die Reste R1 bis R4 die obenwherein R 3 is hydrogen or methyl, reacts, the radicals R 1 to R 4 as above Äthyl- oder Propylrest steht, R4 und R5 Wasser- io angegebene Bedeutung haben.Ethyl or propyl radical, R 4 and R 5 water io have the meaning given. stoff oder Alkylreste bedeuten und Hai ein Substance or alkyl radicals and Hai mean Halogenatom ist, zu Verbindungen der all- In Betracht gezogene Druckschriften:Halogen atom is, to compounds of the all- Considered publications: gemeinen Formel Deutsche Patentschrift Nr. 819 998.common formula German patent specification No. 819 998. O 209 658/424 9.62O 209 658/424 9.62
DEF31541A 1960-06-30 1960-06-30 Process for the preparation of dithiophosphonic acid esters Pending DE1137013B (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
NL130558D NL130558C (en) 1960-06-30
NL266412D NL266412A (en) 1960-06-30
BE605593D BE605593A (en) 1960-06-30
DEF31541A DE1137013B (en) 1960-06-30 1960-06-30 Process for the preparation of dithiophosphonic acid esters
CH725761A CH409954A (en) 1960-06-30 1961-06-21 Process for the preparation of thiophosphonic acid esters
GB23303/61A GB920142A (en) 1960-06-30 1961-06-27 Dithiophosphonic acid esters
FR866644A FR1294428A (en) 1960-06-30 1961-06-30 Process for the preparation of thiophosphonic esters

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF31541A DE1137013B (en) 1960-06-30 1960-06-30 Process for the preparation of dithiophosphonic acid esters

Publications (1)

Publication Number Publication Date
DE1137013B true DE1137013B (en) 1962-09-27

Family

ID=7094237

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF31541A Pending DE1137013B (en) 1960-06-30 1960-06-30 Process for the preparation of dithiophosphonic acid esters

Country Status (5)

Country Link
BE (1) BE605593A (en)
CH (1) CH409954A (en)
DE (1) DE1137013B (en)
GB (1) GB920142A (en)
NL (2) NL266412A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1192647B (en) * 1963-08-31 1965-05-13 Bayer Ag Process for the production of thiol or thionothiolphosphonic acid esters

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE819998C (en) * 1948-02-04 1951-11-08 American Cyanamid Co Process for the preparation of esters of phosphoric or thiophosphoric acid

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE819998C (en) * 1948-02-04 1951-11-08 American Cyanamid Co Process for the preparation of esters of phosphoric or thiophosphoric acid

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1192647B (en) * 1963-08-31 1965-05-13 Bayer Ag Process for the production of thiol or thionothiolphosphonic acid esters

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NL266412A (en) 1900-01-01
GB920142A (en) 1963-03-06
CH409954A (en) 1966-03-31
NL130558C (en) 1900-01-01
BE605593A (en) 1900-01-01

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