DE1109680B - Process for the preparation of alkylphosphonic acid-O-alkyl-thiolesters - Google Patents
Process for the preparation of alkylphosphonic acid-O-alkyl-thiolestersInfo
- Publication number
- DE1109680B DE1109680B DEF24306A DEF0024306A DE1109680B DE 1109680 B DE1109680 B DE 1109680B DE F24306 A DEF24306 A DE F24306A DE F0024306 A DEF0024306 A DE F0024306A DE 1109680 B DE1109680 B DE 1109680B
- Authority
- DE
- Germany
- Prior art keywords
- water
- solution
- ecm
- acid
- alkyl radical
- 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
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- -1 N-methylaminocarbonyl-methyl Chemical group 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 125000001930 alkyl chloride group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- QLQIPARPOAWVAC-UHFFFAOYSA-N (3-methylthiophen-2-yl)phosphonic acid Chemical compound CC=1C=CSC=1P(O)(O)=O QLQIPARPOAWVAC-UHFFFAOYSA-N 0.000 claims 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- WJXGTMBHOPEHGM-UHFFFAOYSA-N Cl.CCOP(C)(O)=S Chemical compound Cl.CCOP(C)(O)=S WJXGTMBHOPEHGM-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- GXARYKPKHLXCPD-UHFFFAOYSA-N (3-ethylthiophen-2-yl)phosphonic acid Chemical compound C(C)C1=C(SC=C1)P(O)(=O)O GXARYKPKHLXCPD-UHFFFAOYSA-N 0.000 description 1
- QBUKAFSEUHGMMX-MTJSOVHGSA-N (5z)-5-[[3-(1-hydroxyethyl)thiophen-2-yl]methylidene]-10-methoxy-2,2,4-trimethyl-1h-chromeno[3,4-f]quinolin-9-ol Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=C(O)C=CC=1O\C2=C/C=1SC=CC=1C(C)O QBUKAFSEUHGMMX-MTJSOVHGSA-N 0.000 description 1
- HOZLOOPIXHWKCI-UHFFFAOYSA-N 2-chloro-n-methylacetamide Chemical compound CNC(=O)CCl HOZLOOPIXHWKCI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- C07F9/28—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
-
- 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
-
- 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
-
- 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
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4015—Esters of acyclic unsaturated acids
-
- 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
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4018—Esters of cycloaliphatic acids
-
- 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
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4021—Esters of aromatic acids (P-C aromatic linkage)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
Description
Es wurde gefunden, daß man Alkylphosphonsäure-O-alkylthiolester der allgemeinen FormelIt has been found that one alkylphosphonic acid-O-alkyl thiol esters of the general formula
R-P'R-P '
OR1 OR 1
SR3 SR 3
in der R ein Alkylrest, R1 ein Alkylrest mit Vorzugsweise 1 bis 4 Kohlenstoffatomen und R2 ein substituierter Alkylrest ist, dadurch herstellen kann, indem man Alkylthionophosphonsäureesterchloride der allgemeinen Formelin which R is an alkyl radical, R 1 is an alkyl radical preferably having 1 to 4 carbon atoms and R 2 is a substituted alkyl radical, can be prepared by using alkylthionophosphonic acid ester chlorides of the general formula
15 S 15 p
R—p;R-p;
in der R und R1 die vorstehend genannte Bedeutung haben, mit Alkalihydroxyd verseift und die entstandenen Verseifungsprodukte mit Alkylchloridgruppen enthaltenden Verbindungen umsetzt.in which R and R 1 have the meaning given above, saponified with alkali metal hydroxide and the saponification products formed are reacted with compounds containing alkyl chloride groups.
Die neuen Ester des Verfahrens sind hervorragende Schädlingsbekämpfungsmittel, vor allem insektentötende Mittel, die in der für Phosphorsäureester enthaltende Schädlingsbekämpfungsmittel bekannten Art und Weise, vorzugsweise in Verbindung mit flüssigen oder festen Verdünnungsmitteln oder Streckmitteln angewendet werden. Als flüssiges Verdünnungsmittel wird vor allem Wasser, dies in Verbindung mit geeigneten handelsüblichen Emulgiermitteln und unter Zusatz von Lösungsvermittlern, wie Dimethylformamid oder Aceton, verwendet. Feste Verdünnungsoder Streckmittel sind Talkum, Kreide, Kohle oder Ruß, die gegebenenfalls auch unter Zusatz von Emulgiermitteln verwendet werden, um die Herstellung von Aufschlämmungen zu ermöglichen.The new esters of the process are excellent pesticides, especially insecticides, which are used in the manner known for pesticides containing phosphoric acid esters, preferably in conjunction with liquid or solid diluents or extenders. The liquid diluent used is primarily water, in conjunction with suitable commercially available emulsifiers and with the addition of solubilizers such as dimethylformamide or acetone. Solid diluents or extenders are talc, chalk, coal or carbon black, which may also be used with the addition of emulsifiers in order to enable the production of slurries.
Die nachfolgenden Beispiele erläutern das Verfahren.The following examples explain the process.
CH3-P:CH 3 -P:
Beispiel 1
/C — CH3
S — CH2 — CH2 — S — C2H=example 1
/ C - CH 3
S - CH 2 - CH 2 - S - C 2 H =
Man löst 73 g Methylthionophosphonsäure-O-methylesterchlorid
vom Kp.u = 53 0C in 250 ecm Methyl-Verfahren
zur Herstellung
von Alkylphosphonsäure-O-alkyl-thiolesternDissolve 73 g Methylthionophosphonsäure-O-methylesterchlorid from Kp. U = 53 0 C in 250 cc of methyl process for preparing
of alkylphosphonic acid O-alkyl thiol esters
Anmelder:Applicant:
Farbenfabriken Bayer Aktiengesellschaft,
Leverkusen-BayerwerkPaint factories Bayer Aktiengesellschaft,
Leverkusen-Bayerwerk
Dr. Dr. h. c. Gerhard Schrader,Dr. Dr. H. c. Gerhard Schrader,
Wuppertal-Cronenberg,
ist als Erfinder genannt wordenWuppertal-Cronenberg,
has been named as the inventor
alkohol, gibt dazu 40 ecm Wasser und anschließend unter Rühren eine Lösung von 58 g Kaliumhydroxyd in 120 ecm Wasser. Man erwärmt die Mischung 2 Stunden auf 700C und gibt 63 g ß-Chloräthylthioäthyläther. Anschließend hält man die Mischung 2 Stunden bei 70 bis 80° C und arbeitet sie wie im Beispiel 2 auf. Es werden 78 g des Esters vom Kp.0,01 = 93°C erhalten; die Ausbeute beträgt 62%; eine 0,001 %ige Lösung tötet Spinnmilben 100%ig.alcohol, add 40 ecm of water and then, while stirring, a solution of 58 g of potassium hydroxide in 120 ecm of water. The mixture was heated for 2 hours at 70 0 C., and 63 g of .beta.-Chloräthylthioäthyläther. The mixture is then kept at 70 to 80 ° C. for 2 hours and worked up as in Example 2. There are 78 g of the ester, bp 0 obtained 01 = 93 ° C. the yield is 62%; a 0.001% solution kills spider mites 100%.
(j /0-C3H5 (j / 0-C 3 H 5
Mn5' ^vM n 5 '^ v
S-CH3-CNS-CH 3 -CN
Man löst 44 g (0,25 Mol) Äthylthionophosphon-O-äthylesterchlorid vom Kp.x = 48°C in 100 ecm Alkohol, gibt dazu 20 ecm Wasser und anschließend eine Lösung von 30 g Kaliumhydroxyd in 50 ecm Wasser. Man hält die Mischung 1 Stunde bei 80° C und gibt dazu bei 80°C 19 g (0,25 Mol) Monochloracetonitril. Man hält die Mischung 1 Stunde bei 80° C, kühlt sie dann auf Zimmertemperatur ab, nimmt sie in 400 ecm Benzol auf und wäscht die benzolische Lösung mit Wasser neutral. Durch Destillieren der Lösung erhält man 24 g des Esters vom Kp.0,01 = 90° C; die Ausbeute beträgt 50%; eine 0,01 %ige Lösung tötet Blattläuse 100%ig.Dissolve 44 g (0.25 mol) Äthylthionophosphon-O-äthylesterchlorid from Kp. X = 48 ° C in 100 cc of alcohol, are to 20 cc of water and then a solution of 30 g potassium hydroxide in 50 cc of water. The mixture is kept at 80 ° C. for 1 hour and 19 g (0.25 mol) of monochloroacetonitrile are added at 80 ° C. The mixture is kept at 80 ° C. for 1 hour, then cooled to room temperature, taken up in 400 ecm of benzene and the benzene solution is washed neutral with water. By distilling the solution obtained 24 g of the ester, bp 0, 01 = 90 ° C. the yield is 50%; a 0.01% solution kills aphids 100%.
109 619/449109 619/449
C2Hg P-C 2 Hg P-
,0-C2H, 0-C 2 H
2H3 2 H 3
S — CH2- CH2-S - CH 2 - CH 2 -
,C2H5 , C 2 H 5
C2H5 C 2 H 5
CH3-P::CH 3 -P ::
Q-OC2H5 Q-OC 2 H 5
S — CH2 — CO — NH —S - CH 2 - CO - NH -
C2H5-P^C 2 H 5 -P ^
-Q-C2H5 -QC 2 H 5
S-CH2-CO-NH-CH3 S-CH 2 -CO-NH-CH 3
Man löst 44 g (0,25 Mol) Äthylthionophosphon-O-äthylesterchlorid in 100 ecm Alkohol, gibt dazu 20 ecm Wasser und anschließend eine Lösung von 30 g Kaliumhydroxyd in 50 ecm Wasser. Man hält die Mischung 1 Stunde bei 800C und gibt dazu unter Rühren bei 70° C 35 g (0,25 Mol) N-Diäthyl-ß-aminoäthylchlorid. Man hält die Mischung 1 Stunde bei 70 bis 75°C, kühlt sie dann auf Zimmertemperatur ab und nimmt sie in 400 ecm Benzol auf. Die entstandene Benzollösung wird mit wenig Wasser gewaschen, über Natriumsulfat getrocknet und anschließend fraktioniert destilliert. Man erhält 20 g des Esters vom Kp.0,01 = 94°C, der in Wasser löslich ist; die Ausbeute beträgt 32%; eine 0,001 °/oige Lösung tötet Blattläuse 1000/„ig.44 g (0.25 mol) of ethylthionophosphon-O-ethyl ester chloride are dissolved in 100 ecm of alcohol, 20 ecm of water are added and then a solution of 30 g of potassium hydroxide in 50 ecm of water. The mixture is maintained for 1 hour at 80 0 C., and thereto with stirring at 70 ° C 35 g (0.25 mol) of N-diethyl-.beta.-aminoäthylchlorid. The mixture is kept at 70 to 75 ° C. for 1 hour, then cooled to room temperature and taken up in 400 ecm of benzene. The resulting benzene solution is washed with a little water, dried over sodium sulfate and then fractionally distilled. 20 g of the ester with a boiling point of 0.01 = 94 ° C., which is soluble in water, are obtained; the yield is 32%; a 0,001 ° / o solution kills aphids 100 0 / "ig.
Man löst 44g (0,25MoI) Äthyl-thionophosphonsäure-O-äthylesterchlorid
in 100 ecm Äthanol, fügt unter Rühren zunächst 20 ecm Wasser, darauf eine
Lösung von 15 g Kaliumhydroxyd in 50 ecm Wasser zum Reaktionsgemisch, erhitzt dieses 1 Stunde auf
800C und tropft anschließend bei dieser Temperatur 38 g Chloressigsäuremethylamid — gelöst in 50 ecm
Acetonitril — ein. Danach wird die Mischung zur Vervollständigung der Umsetzung noch 1 bis 2 Stunden
auf 70 bis 800C erwärmt und schließlich in 500 ecm Benzol aufgenommen. Man arbeitet das Reaktionsgemisch wie im Beispiel 2 beschrieben auf und erhält
30 g (52 % der Theorie) Äthylthiolphosphonsäure-O - äthyl- S - (N- methylaminocarbonyl- methyl) - ester in
Form eines wasserlöslichen, gelben Öles.
Analyse (für ein Molgewicht von 225):Dissolve 44g (0,25MoI) ethyl thionophosphonsäure-O-äthylesterchlorid in 100 cc of ethanol, with stirring, first 20 cc of water, then a solution of 15 g potassium hydroxide in 50 cc of water to the reaction mixture, heated, this 1 hour at 80 0 C. and then 38 g of methyl chloroacetamide - dissolved in 50 ecm of acetonitrile - are added dropwise at this temperature. Thereafter, the mixture to complete the reaction a further 1 to 2 hours and heated at 70 to 80 0 C finally taken up in 500 cc of benzene. The reaction mixture is worked up as described in Example 2 and 30 g (52% of theory) of ethylthiolphosphonic acid O-ethyl-S (N-methylaminocarbonyl-methyl) ester are obtained in the form of a water-soluble, yellow oil.
Analysis (for a molecular weight of 225):
Berechnet ... N 6,2%, S 14,2%, P 13,8%;Calculated ... N 6.2%, S 14.2%, P 13.8%;
gefunden ... N 5,9%, S 14,4%, P 13,7%.found ... N 5.9%, S 14.4%, P 13.7%.
Claims (1)
Analyse (für ein Molgewicht von 211):40 g (0.25 mol) of methyl thionophosphonic acid O-ethyl ester chloride are dissolved in 100 ecm of methanol. The solution obtained is first mixed with 20 cc of water, then with a solution of 15 g potassium hydroxide in 50 cc of water and the mixture heated for 1 hour at 8O 0 C. Subsequently, at 70 to 8O 0 C with stirring, a solution of 38 g Chloressigsäuremethylamid in 50 ecm acetonitrile was added to the reaction mixture, the latter was stirred for a further 1 to 2 hours at the specified temperature to complete the reaction and then taken up in 500 ecm benzene. The benzene solution is washed with water and worked up as described in Example 2. 22 g (corresponding to 42% of theory) of methylthiolphosphonic acid O-ethyl-S- (N-methylaminocarbonyl-methyl) ester are obtained in the form of a water-soluble, yellow oil.
Analysis (for a molecular weight of 211):
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF24306A DE1109680B (en) | 1957-06-24 | 1957-11-02 | Process for the preparation of alkylphosphonic acid-O-alkyl-thiolesters |
| CH6525158A CH414621A (en) | 1957-06-24 | 1958-10-21 | Process for the preparation of phosphonic acid esters |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2992265X | 1957-06-24 | ||
| DEF24305A DE1053503B (en) | 1957-11-02 | 1957-11-02 | Process for the production of sulfur-containing phosphonic acid esters |
| DEF24306A DE1109680B (en) | 1957-06-24 | 1957-11-02 | Process for the preparation of alkylphosphonic acid-O-alkyl-thiolesters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1109680B true DE1109680B (en) | 1961-06-29 |
Family
ID=32397424
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF24306A Pending DE1109680B (en) | 1957-06-24 | 1957-11-02 | Process for the preparation of alkylphosphonic acid-O-alkyl-thiolesters |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH414621A (en) |
| DE (1) | DE1109680B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1156070B (en) * | 1961-11-28 | 1963-10-24 | Bayer Ag | Process for the production of phosphorus, phosphonic, phosphine or thiophosphorus, phosphonic and phosphinic acid esters |
| US3150162A (en) * | 1959-09-03 | 1964-09-22 | Bayer Ag | Thiophosphonic acid esters |
| DE1212777B (en) * | 1963-11-07 | 1966-03-17 | Bayer Ag | Fungitoxic agents |
-
1957
- 1957-11-02 DE DEF24306A patent/DE1109680B/en active Pending
-
1958
- 1958-10-21 CH CH6525158A patent/CH414621A/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3150162A (en) * | 1959-09-03 | 1964-09-22 | Bayer Ag | Thiophosphonic acid esters |
| DE1156070B (en) * | 1961-11-28 | 1963-10-24 | Bayer Ag | Process for the production of phosphorus, phosphonic, phosphine or thiophosphorus, phosphonic and phosphinic acid esters |
| DE1212777B (en) * | 1963-11-07 | 1966-03-17 | Bayer Ag | Fungitoxic agents |
Also Published As
| Publication number | Publication date |
|---|---|
| CH414621A (en) | 1966-06-15 |
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