DE1025882B - Process for the preparation of thionophosphoric acid esters - Google Patents
Process for the preparation of thionophosphoric acid estersInfo
- Publication number
- DE1025882B DE1025882B DEF20780A DEF0020780A DE1025882B DE 1025882 B DE1025882 B DE 1025882B DE F20780 A DEF20780 A DE F20780A DE F0020780 A DEF0020780 A DE F0020780A DE 1025882 B DE1025882 B DE 1025882B
- Authority
- DE
- Germany
- Prior art keywords
- acid esters
- acid
- preparation
- thionophosphoric acid
- formula
- 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
- 150000002148 esters Chemical class 0.000 title claims description 13
- 239000002253 acid Substances 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- -1 alkyl radicals Chemical class 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000012964 benzotriazole Substances 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- DMSSTTLDFWKBSX-UHFFFAOYSA-N 1h-1,2,3-benzotriazin-4-one Chemical compound C1=CC=C2C(=O)N=NNC2=C1 DMSSTTLDFWKBSX-UHFFFAOYSA-N 0.000 claims description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000003578 thiophosphoric acid amides Chemical class 0.000 description 3
- 150000003580 thiophosphoric acid esters Chemical class 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MBWRLGQNVZIZBI-UHFFFAOYSA-N chloro-diethyl-dihydroxy-$l^{5}-phosphane Chemical compound CCP(O)(O)(Cl)CC MBWRLGQNVZIZBI-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- UTMDJGPRCLQPBT-UHFFFAOYSA-N 4-nitro-1h-1,2,3-benzotriazole Chemical compound [O-][N+](=O)C1=CC=CC2=NNN=C12 UTMDJGPRCLQPBT-UHFFFAOYSA-N 0.000 description 1
- AOCDQWRMYHJTMY-UHFFFAOYSA-N 5-nitro-2h-benzotriazole Chemical compound C1=C([N+](=O)[O-])C=CC2=NNN=C21 AOCDQWRMYHJTMY-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 231100000926 not very toxic Toxicity 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
- C07F9/6518—Five-membered rings
- C07F9/65188—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
-
- 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
- C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
- C07F9/6521—Six-membered rings
- C07F9/65218—Six-membered rings condensed with carbocyclic rings or carbocyclic ring systems
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
BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY
DEUTSCHESGERMAN
kl. 12 p 10kl. 12 p 10
INTERNAT. KL. C 07 fINTERNAT. KL. C 07 f
PATENTAMTPATENT OFFICE
F 20780 IVb/12 ρ ANMELDETAG: 13.JULI1956F 20780 IVb / 12 ρ REGISTRATION DATE: JULY 13, 1956
B EKANNTMACHUNG
DER ANMELDUNG
UND AUSGABE DER
AUSLEGESCHRIFT: 13.MÄRZ1958NOTICE
THE REGISTRATION
AND ISSUE OF THE
EDITORIAL: MARCH 13, 1958
Es wurde gefunden, daß man Thionophosphorsäureester der FormelIt has been found that thionophosphoric acid esters of the formula
,OR1 , OR 1
,ρ:, ρ:
OR2 OR 2
z:'z: '
Verfahren zur Herstellung
von ThionophosphorsäureesternMethod of manufacture
of thionophosphoric acid esters
Anmelder:Applicant:
Farbenfabriken Bayer Aktiengesellschaft, Leverkusen-BayerwerkPaint factories Bayer Aktiengesellschaft, Leverkusen-Bayerwerk
IOIO
in der Z für die Atome steht, die zur Bildung eines Benzotriazols bzw. Benzazimids erforderlich sind, und R1 und R2 für Alkylreste stehen, erhalten kann, wenn man cyclische Stickstoffverbindungen der Formelin which Z stands for the atoms which are necessary for the formation of a benzotriazole or benzazimide, and R 1 and R 2 stand for alkyl radicals, can be obtained if cyclic nitrogen compounds of the formula
in der Z die oben angegebene Bedeutung hat, in Gegenwart eines Lösungsmittels und einer säurebindenden Verbindung mit einem Dialkylphosphorigsäuremonochlorid umsetzt und auf die so erhaltene Verbindung anschließend die für die Bildung der Thionophosphorsäureester erforderliche Menge Schwefel einwirken läßt.in which Z has the meaning given above, in the presence of a solvent and an acid-binding one Reacts compound with a Dialkylphosphorigsäuremonochlorid and on the compound thus obtained then the amount of sulfur required for the formation of the thionophosphoric acid ester is allowed to act.
Für das erfindungsgemäße Verfahren geeignete Lösungsmittel sind z. B. Dimethylformamid, Aceton, Methyläthylketon, Toluol oder Xylol. Als säurebindende Mittel haben sich besonders tertiäre Basen, wie Pyridin, Triäthylamin oder Dimethylanilin, bewährt.Suitable solvents for the process according to the invention are, for. B. dimethylformamide, acetone, methyl ethyl ketone, Toluene or xylene. Tertiary bases such as pyridine, Triethylamine or dimethylaniline, proven.
Die Umsetzung der cyclischen Stickstoffverbindungen mit den Dialkylphosphorigsäurechloriden nimmt man vorteilhafterweise in inerter Atmosphäre, z. B. unter Stickstoff, bei Zimmertemperatur oder nur schwach erhöhter Temperatur vor. Die anschließende Umsetzung mit dem Schwefel erfolgt zweckmäßigerweise bei etwas erhöhter Temperatur, z. B. im "Bereich von 60 bis 80°C.The reaction of the cyclic nitrogen compounds with the dialkylphosphorous acid chlorides is used advantageously in an inert atmosphere, e.g. B. under nitrogen, at room temperature or only weakly elevated temperature. The subsequent reaction with the sulfur is expediently carried out with something elevated temperature, e.g. B. in the "range of 60 to 80 ° C.
Die Verfahrensprodukte sind nicht sehr toxisch und zeichnen sich durch insektizide Wirksamkeit aus.The products of the process are not very toxic and are distinguished by their insecticidal activity.
Aus den deutschen Patentschriften 927 270 und 933 627 sind schon Thiophosphorsäureester bekannt, in denen ein Esterrest eine N-Methylen-benzotriazol- bzw. N-Methylen-benzazimid-Gruppe ist.From the German patents 927 270 and 933 627 thiophosphoric acid esters are already known in which an ester residue an N-methylene-benzotriazole or N-methylene-benzazimide group is.
Verglichen wurden nun die erfmdungsgemäßen Thiophosphorsäureamide mit den aus den deutschen Patentschriften 933 627 und 927270 her bekannten Thiophosphorsäureestern. The thiophosphoric acid amides according to the invention have now been compared with the thiophosphoric acid esters known from German patents 933 627 and 927270.
Dr. Gerhard Schrader, Wuppertal-Cronenberg, ist als Erfinder genannt wordenDr. Gerhard Schrader, Wuppertal-Cronenberg, has been named as the inventor
1. Erfindungsgemäße Thiophosphorsäureamide: S1. Thiophosphoric acid amides according to the invention: S.
-OC2H5 -OC 2 H 5
1OC9H, 1 OC 9 H,
Fliegen: 0,001% 100%Flying: 0.001% 100%
coco
-OC2H5 -OC 2 H 5
p;p;
Fliegen: 0,001% 100%Flying: 0.001% 100%
OC2H,OC 2 H,
Fliegen: 0,001% 100%Flying: 0.001% 100%
NO9 NO 9
= p:= p:
.OC2H5 .OC 2 H 5
OC2H5 OC 2 H 5
Fliegen: 0,0001% 100%Flying: 0.0001% 100%
709 909/393709 909/393
2. Bekannte Thiophosphorsäureester:2. Known thiophosphoric acid esters:
a) aus der deutschen Patentschrift 933 627a) from German patent specification 933 627
Fliegen: 0,2% 100°/0 Flying: 0.2% 100 ° / 0
Fliegen: 0,1% 100%Flying: 0.1% 100%
wird. Nach dem Abklingen der Reaktion gibt man auf einmal 8 g Schwefel zu. Die Reaktionstemperatur steigt von selbst auf 600C. Man hält bei 7O0C noch V2 Stunde, kühlt dann ab und arbeitet, wie im Beispiel 1 beschrieben, auf.will. After the reaction has subsided, 8 g of sulfur are added all at once. The reaction temperature rises by itself at 60 0 C. at 7O 0 C is maintained even V 2 hours, then cooled and worked as described in Example 1 on.
Es werden 40 g des neuen Esters der FormelThere will be 40 g of the new ester of the formula
COCO
OC2H8 OC 2 H 8
n — p :'n - p: '
OC2H5 OC 2 H 5
CH2-S-P;CH 2 -SP;
XOCH3 X OCH 3
b) aus der deutschen Patentschrift 927270 Sb) from German patent specification 927270 p
N-CH2-S-PN-CH 2 -SP
I/I /
OCH,OCH,
Fliegen: 0,1% OCH3 50 bis 100%Flying: 0.1% OCH 3 50 to 100%
Wie aus den Vergleichsversuchen deutlich zu ersehen ist, zeichnen sich die erfindungsgemäßen Thiophosphorsäureamide den durch einen gleichen stickstoffhaltigen Rest substituierten Estern gegenüber durch eine hervorragende Fliegenwirkung aus.As can be clearly seen from the comparative experiments, the thiophosphoric acid amides according to the invention are notable the esters substituted by an identical nitrogen-containing radical compared with an excellent one Fly effect off.
60 g Benzotriazol werden in 200 ecm Methyläthylketon gelöst. Dazu gibt man unter Rühren 42 g Pyridin. Dann leitet man einen Stickstoffstrom durch das Reaktionsprodukt und tropft unter weiterem Rühren bei 20 bis 30° C 80 g Diäthylphosphorigsäuremonochlorid zu. Unter exothermer Reaktion bildet sich der Phosphorigsäureester. Nach dem Abklingen der Wärmetönung gibt man auf einmal 16 g Schwefel zu. Die Temperatur des Reaktionsproduktes steigt auf 700C. Man erwärmt noch 1I2 Stunde auf 76° C und gibt dann das abgekühlte Reaktionsprodukt auf 200 ecm Eiswasser, dem 20 ecm Salzsäure zugesetzt waren. Die Methyläthylketonschicht wird in 300 ecm Äther aufgenommen, mit festem Bikarbonat entsäuert und mit Natriumsulfat getrocknet. Beim Abdestillieren der Lösungsmittel erhält man 80 g des neuen Esters der Formel60 g of benzotriazole are dissolved in 200 ecm of methyl ethyl ketone. 42 g of pyridine are added with stirring. A stream of nitrogen is then passed through the reaction product and 80 g of diethylphosphorous acid monochloride are added dropwise at 20.degree.-30.degree. C. while stirring. The phosphorous acid ester is formed with an exothermic reaction. After the heat dissipation has subsided, 16 g of sulfur are added all at once. The temperature of the reaction product increased to 70 0 C. It is heated for 1 I 2 hour at 76 ° C and then the cooled reaction product on 200 cc of ice-water, the 20 cc of hydrochloric acid were added. The methyl ethyl ketone layer is taken up in 300 ecm of ether, deacidified with solid bicarbonate and dried with sodium sulfate. When the solvent is distilled off, 80 g of the new ester of the formula are obtained
Il /OC2H5 als wasserunlösliches, gelbstichiges, viskoses Öl gewonnen. An der Ratte (per os) zeigt der neue Ester eine mittlere Toxizität von 25 mg/kg.II / OC 2 H 5 obtained as a water-insoluble, yellowish, viscous oil. In the rat (per os) the new ester shows an average toxicity of 25 mg / kg.
43 g 5-Nitrobenzotriazol werden in 250 ecm Methyläthylketon gelöst. Man gibt 21 g Pyridin zu und tropft bei 3O0C unter Stickstoff 40 g Diäthylphosphorigsäuremonochlorid — gelöst in 40 ecm Toluol — zu. Dann gibt man 8 g Schwefel zu und erwärmt 1 Stunde auf 700C. Nach dem üblichen Aufarbeiten erhält man 46 g eines rotstichiggelben, viskosen Öls, das in Wasser nicht löslich ist.43 g of 5-nitrobenzotriazole are dissolved in 250 ecm of methyl ethyl ketone. Are added to 21 g of pyridine and added dropwise at 3O 0 C under nitrogen, 40 g Diäthylphosphorigsäuremonochlorid - dissolved in 40 cc of toluene -. Then 8 g of sulfur are added and the mixture is heated to 70 ° C. for 1 hour. After the usual work-up, 46 g of a reddish-tinged yellow, viscous oil which is not soluble in water are obtained.
An der Ratte (per os) zeigt der neue Ester der FormelOn the rat (per os) the new ester shows the formula
NO,NO,
,N,, N,
= ρ:= ρ:
,OC2H5 , OC 2 H 5
OC,HR OC, H R
eine mittlere Toxizität von 50 mg/kg. Beispiel 4a mean toxicity of 50 mg / kg. Example 4
43 g 4-Nitrobenzotriazol werden in 250 ecm Methyläthylketon gelöst. Man gibt 21 g Pyridin dazu und tropft unter Stickstoff 40 g Diäthylphosphorigsäuremonochlorid — gelöst in 40 ecm Toluol — bei 3O0C zu. Dann gibt man auf einmal 8 g Schwefel zu und hält noch 1 Stunde bei 76° C. Nach dem üblichen Aufarbeiten werden 38 g eines stark viskosen, rotbraunen Öls erhalten.43 g of 4-nitrobenzotriazole are dissolved in 250 ecm of methyl ethyl ketone. One gives 21 g of pyridine and added dropwise under nitrogen to 40 g Diäthylphosphorigsäuremonochlorid - dissolved in 40 cc of toluene - at 3O 0 C to. Then 8 g of sulfur are added all at once and the mixture is kept at 76 ° C. for a further hour. After the usual work-up, 38 g of a highly viscous, red-brown oil are obtained.
An der Ratte (per os) zeigt der neue Ester der FormelOn the rat (per os) the new ester shows the formula
NO2 NO 2
* OC2H5 * OC 2 H 5
5555
OC2HOC 2 H
2H6 2 H 6
als viskoses, gelbes, wasserunlösliches Öl.as a viscous, yellow, water-insoluble oil.
An der Ratte (per os) beträgt die mittlere Toxizität 25 mg/kg.The mean toxicity in rats (per os) is 25 mg / kg.
37 g Benzazimid werden in 250 ecm Methyläthylketon gelöst. Zu dieser Lösung gibt man 21 g Pyridin. Dann tropft man unter Rühren und gleichzeitigem Durchleiten von Stickstoff 40 g Diäthylphosphorigsäuremonochlorid, gelöst in 40 ecm Toluol, zu. Man sorgt durch Kühlen dafür, daß die Temperatur von 3O0C nicht überschritten OC2H8 eine mittlere Toxizität von 20 mg/kg.37 g of benzazimide are dissolved in 250 ecm of methyl ethyl ketone. 21 g of pyridine are added to this solution. 40 g of diethylphosphorous acid monochloride, dissolved in 40 ecm of toluene, are then added dropwise while stirring and at the same time nitrogen is passed through. Man ensures by cooling that the temperature of 3O 0 C is not exceeded OC 2 H 8 is a medium toxicity of 20 mg / kg.
Claims (2)
Deutsche Patentschriften Nr. 927 270, 933 627.Considered publications:
German patent specifications No. 927 270, 933 627.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF20780A DE1025882B (en) | 1956-07-13 | 1956-07-13 | Process for the preparation of thionophosphoric acid esters |
| FR1178350D FR1178350A (en) | 1956-07-13 | 1957-07-10 | Process for the preparation of thiophosphoric esters of nitrogenous cyclic compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF20780A DE1025882B (en) | 1956-07-13 | 1956-07-13 | Process for the preparation of thionophosphoric acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1025882B true DE1025882B (en) | 1958-03-13 |
Family
ID=7089810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF20780A Pending DE1025882B (en) | 1956-07-13 | 1956-07-13 | Process for the preparation of thionophosphoric acid esters |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1025882B (en) |
| FR (1) | FR1178350A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE927270C (en) * | 1953-02-26 | 1955-05-02 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
| DE933627C (en) * | 1953-02-10 | 1955-09-29 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
-
1956
- 1956-07-13 DE DEF20780A patent/DE1025882B/en active Pending
-
1957
- 1957-07-10 FR FR1178350D patent/FR1178350A/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE933627C (en) * | 1953-02-10 | 1955-09-29 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
| DE927270C (en) * | 1953-02-26 | 1955-05-02 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1178350A (en) | 1959-05-06 |
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