DE830509C - Process for the preparation of neutral esters of thiophosphoric acid - Google Patents
Process for the preparation of neutral esters of thiophosphoric acidInfo
- Publication number
- DE830509C DE830509C DEF1499A DEF0001499A DE830509C DE 830509 C DE830509 C DE 830509C DE F1499 A DEF1499 A DE F1499A DE F0001499 A DEF0001499 A DE F0001499A DE 830509 C DE830509 C DE 830509C
- Authority
- DE
- Germany
- Prior art keywords
- thiophosphoric acid
- preparation
- alkyl
- neutral esters
- water
- 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
Links
- 150000002148 esters Chemical class 0.000 title claims description 6
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 3
- 230000007935 neutral effect Effects 0.000 title claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 150000003839 salts Chemical class 0.000 description 6
- 239000011734 sodium Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000007970 thio esters Chemical class 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- YMPPRYJBYFNJTO-UHFFFAOYSA-M sodium;diethoxy-oxido-sulfanylidene-$l^{5}-phosphane Chemical compound [Na+].CCOP([O-])(=S)OCC YMPPRYJBYFNJTO-UHFFFAOYSA-M 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VFQYMJYUSRAJCZ-UHFFFAOYSA-N 1-(chloromethylsulfanyl)-4-methylbenzene Chemical compound CC1=CC=C(SCCl)C=C1 VFQYMJYUSRAJCZ-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- NFORZJQPTUSMRL-UHFFFAOYSA-N dipropan-2-yl hydrogen phosphite Chemical compound CC(C)OP(O)OC(C)C NFORZJQPTUSMRL-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003580 thiophosphoric acid esters Chemical class 0.000 description 1
Classifications
-
- 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
-
- 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
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Es wurde gefunden, daß man neutrale Ester der Thiophosphorsäure erhält, wenn man Verbindungen der allgemeinen Formel:It has been found that neutral esters of thiophosphoric acid are obtained when compounds the general formula:
Cl- Alkyl — S-RCl- alkyl - S-R
mit Alkalidialkylthiophosphaten umsetzt. In der angegebenen Formel steht R für einen Alkyl-, Aryl- oder Aralkylrest. Die zur Umsetzung verwendeten Alkalidialkylthiophosphate reagieren im vorliegenden Fall in der unten angegebenen tautomeren Form 2:with alkali dialkyl thiophosphates. In the formula given, R stands for an alkyl, aryl or aralkyl radical. The alkali dialkyl thiophosphates used for the reaction react in the present Case in the tautomeric form 2 given below:
Alkyl O
»5 Alkyl CrAlkyl O
»5 alkyl Cr
Alkyl CK
Alkyl OAlkyl CK
Alkyl O
.0.0
^S —Na^ S —Na
(T. W. Mastin, G. R. Norman und E. A. Weilmuenster, Journal of the American Chemical Society, Bd. 67 [1945], S. 1662 bis 1664), so daß bei dieser Umsetzung Ester der Thiophosphorsäure entstehen.(T. W. Mastin, G. R. Norman and E. A. Weilmuenster, Journal of the American Chemical Society, vol. 67 [1945], pp. 1662 to 1664) so that in this reaction, thiophosphoric acid esters are formed.
Die Umsetzung der oben durch die allgemeine Formel gekennzeichneten Chloride mit den Alkali- as salzen der Dialkylthiophosphorsäure kann in Gegenwart von inerten Lösungsmitteln, z. B. Benzol, Toluol, Chlorbenzol, vorgenommen werden; außerdem sind für die Umsetzung als Lösungsmittel aber auch sehr gut Ketone, ζ. B. Methyläthylketon, Methylpropylketon u. a., geeignet.The reaction of the chlorides characterized above by the general formula with the alkali as salts of dialkylthiophosphoric acid can in the presence of inert solvents, eg. B. benzene, Toluene, chlorobenzene, can be made; also are for the implementation as a solvent but also very good ketones, ζ. Methyl ethyl ketone, methyl propyl ketone and others are suitable.
Die nach dem Verfahren erhältlichen neuen Verbindungen zeichnen sich durch hervorragende kontaktinsekticide Wirkungen und durch ebensolche chemotherapeutische Wirkungen auf die lebende Pflanze aus.The new compounds obtainable by the process are characterized by and excellent contact insecticidal effects chemotherapeutic effects on the living plant.
7 g feingepulvertes Natrium werden in 100 ecm Toluol angeschlämmt. Dazu gibt man bei 400 43 g7 g of finely powdered sodium are suspended in 100 ecm of toluene. Add 43 g at 40 0
Diäthylphosphit. Die Temperatur von 400 wird V2 Stunde lang gehalten. Es hat sich dann das Natrium gelöst. Dann fügt man unter Rühren zu dem Reaktionsprodukt 10 g Schwefel bei 6o° und erwärmt 1 Stunde auf 1050. Auf das nun in feinster Verteilung vorliegende Natriumdiäthylthiophosphat läßt man bei 550 34 g Chlormethyläthylsulfid (Berichte der Deutschen Chemischen Gesellschaft, Bd. 69, [1936], S. 1612) einwirken. Man hält die Temperatur des Reaktionsgemisches noch 1 Stunde bei 55°, gibt dann 8 ecm Wasser hinzu, um die entstandenen Sailze anzudösen, hebt die Toluolschicht und fraktioniert sie. Es werden 40 g des neuen Esters erhalten. Ausbeute entsprechend 6o°/o der Theorie. Der neue Thioester ist wasserunlöslich und siedet unter einem Druck von 1,5 mm Hg bei 129 bis 1300.Diethyl phosphite. The temperature of 40 0 is held for 2 hours. The sodium has then dissolved. Is then added with stirring to the reaction product, 10 g sulfur at 6o ° and heated for 1 hour at 105 0th To the now present in suspension Natriumdiäthylthiophosphat allowed at 55 0 34 g Chlormethyläthylsulfid (Reports of the German Chemical Society, Vol. 69, [1936], p 1612) interact. The temperature of the reaction mixture is kept at 55 ° for 1 hour, then 8 ecm of water is added to dissolve the resulting sailze, the toluene layer is lifted and it is fractionated. 40 g of the new ester are obtained. Yield corresponding to 60% of theory. The new thioester is insoluble in water and boiling under a pressure of 1.5 mm Hg at 129-130 0th
Wie in Beispiel 1 wird aus den gleichen Gewichtsmengen das fein verteilte Natriumdiäthylthiophosphat hergestellt. Zu dieser Anschlämmung gibt man 52 g Chlormethyl-4-methylphenylsulfid (Berichte der Deutschen Chemischen Gesellschaft Bd. 69 [1936], S. 1612). Das Reaktionsgemisch wird 4 Stunden auf 105° erwärmt; man bringt dann die entstandenen Salze mit 10 ecm Wasser in eine filtrierbare Form, trennt die Toluolschicht ab und fraktioniert. Man erhält 60 g des neuen Thioesters vom Kp 0,5 1780 entsprechend einer Ausbeute von 65%. Die neue Substanz ist ein wasserunlösliches, farbloses öl.As in Example 1, the finely divided sodium diethyl thiophosphate is prepared from the same amounts by weight. 52 g of chloromethyl-4-methylphenyl sulfide are added to this suspension (reports from the German Chemical Society, vol. 69 [1936], p. 1612). The reaction mixture is heated to 105 ° for 4 hours; the resulting salts are then brought into a filterable form with 10 ecm of water, the toluene layer is separated off and fractionated. 60 g of the new thioester with a boiling point of 0.5 178 0 are obtained, corresponding to a yield of 65%. The new substance is a water-insoluble, colorless oil.
Wie in Beispiel 1 wird aus den gleichen Mengen das Natriumdiäthylthiophosphat hergestellt. Zu diesem Salz gibt man unter Rühren bei 700 37 g /J-Chloräthyläthylsulfid (Liebigs Annalen der Chemie Bd. 240 [1887], S. 310). Man erwärmt das Reaktionsgemisch dann noch 2 Stunden auf 1500 und entfernt wie in den vorhergehenden Beispielen die Salze mit Wasser. Beim Fraktionieren der Toluolschicht werden 54 g des neuen Thioesters erhalten entsprechend einer Ausbeute von 70 °/o.As in Example 1, the sodium diethyl thiophosphate is prepared from the same amounts. To the salt is added with stirring at 70 0 37 g / J-Chloräthyläthylsulfid (Liebigs Annalen der Chemie, Vol. 240 [1887], p 310). Heating the reaction mixture then for 2 hours at 150 0 and removed as in the previous examples, the salts with water. When the toluene layer is fractionated, 54 g of the new thioester are obtained, corresponding to a yield of 70%.
Der neue Ester ist ein wasserunlösliches, farbloses öl, das unter einem Druck von 1 mm bei 132 bis 1330 siedet.The new ester is a water-insoluble, colorless oil that boils at 132 to 133 0 under a pressure of 1 mm.
In ähnlicher Weise kann z. B. folgende Verbindung hergestellt werden:Similarly, e.g. B. the following connection can be established:
QH5O.QH 5 O.
C2H5O'C 2 H 5 O '
.0.0
S-S-
C-* ΓΙ 2C- * ΓΙ 2
O · 0 ΓΙ οO · 0 ΓΙ ο
Kp2 134°Kp 2 134 °
7 g Natriumpulver werden in 100 ecm Toluol angeschlämmt. Dazu gibt man 42 g Diisopropylphosphit bei 500 und erwärmt so lange, bis das Natrium gelöst ist. Dann fügt man 9 g Schwefel hinzu und erwärmt noch 1 Stunde auf 90 bis 950. Man kühlt dann auf 500 ab und läßt bei dieser Temperatur 37 S ß-Chloräthyläthylsulfid zutropfen. Das Reaktionsprodukt wird dann noch unter Rühren 4 Stunden bei 90 bis 950 gehalten. Die entstandenen Salze werden darauf durch Xugabe von 5 ecm Wasser in eine filtrierbare Form gebracht. Nach dem Absaugen der Salze wird die Toluollösung vom Lösungsmittel befreit. Das zurückbleibende Rohprodukt wird unter einem Druck von 2 mm bei einer Innentemperatur von 120° 10 Minuten gehalten, um die Reste der flüchtigen Lösungsmittel zu beseitigen. Man erhält den neuen Ester auf diese Weise als braungelbes, wasserunlösliches öl (60 g). Bei einem Druck von 2 mm Hg läßt sich der EsteT nur unter starker Zersetzung destillieren.7 g of sodium powder are suspended in 100 ecm of toluene. To this are added 42 g of diisopropyl phosphite at 50 ° and heated until the sodium has dissolved. Then one adds 9 grams of sulfur and heated for 1 hour at 90 to 95 0th It is then cooled to 0 and 50 can at this temperature for 37 S ß-Chloräthyläthylsulfid added dropwise. The reaction product is then held still with stirring for 4 hours at 90 to 95 0th The resulting salts are then converted into a filterable form by adding 5 ecm of water. After the salts have been filtered off with suction, the toluene solution is freed from the solvent. The remaining crude product is kept under a pressure of 2 mm at an internal temperature of 120 ° for 10 minutes in order to remove the residues of the volatile solvents. The new ester is obtained in this way as a brown-yellow, water-insoluble oil (60 g). At a pressure of 2 mm Hg, the EsteT can only be distilled with severe decomposition.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF1499A DE830509C (en) | 1950-05-24 | 1950-05-24 | Process for the preparation of neutral esters of thiophosphoric acid |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF1499A DE830509C (en) | 1950-05-24 | 1950-05-24 | Process for the preparation of neutral esters of thiophosphoric acid |
Publications (1)
Publication Number | Publication Date |
---|---|
DE830509C true DE830509C (en) | 1952-02-04 |
Family
ID=7082897
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEF1499A Expired DE830509C (en) | 1950-05-24 | 1950-05-24 | Process for the preparation of neutral esters of thiophosphoric acid |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE830509C (en) |
Cited By (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE917668C (en) * | 1952-08-01 | 1954-09-09 | Bayer Ag | Process for the preparation of neutral esters of dithiophosphoric acid |
DE942988C (en) * | 1953-12-11 | 1956-05-09 | Bayer Ag | Process for the preparation of thiolphosphoric acid triesters |
DE957213C (en) * | 1954-06-10 | 1957-01-31 | Geigy Ag J R | Process for the preparation of new thiolthionophosphoric acid esters |
DE961083C (en) * | 1954-08-02 | 1957-04-04 | Bayer Ag | Process for the preparation of S-ª ‰ -Merkapto-aethyl-O, O-dialkyl-thiol-phosphoric acid esters |
DE964045C (en) * | 1955-05-14 | 1957-05-16 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
DE1014107B (en) * | 1954-12-28 | 1957-08-22 | Wolfen Filmfab Veb | Process for the preparation of esters of phosphorus-containing acids |
DE1016260B (en) * | 1956-03-09 | 1957-09-26 | Bayer Ag | Process for the production of O, O-dialkyl-thiol-phosphoric acid-S-mercaptomethyl-triesters |
DE1018053B (en) * | 1955-10-29 | 1957-10-24 | Bayer Ag | Process for the preparation of S-chlorobenzyl esters of O, O-dialkyl-thiolphosphoric acid |
DE1032247B (en) * | 1954-12-04 | 1958-06-19 | Bayer Ag | Process for the production of organic phosphorus compounds |
DE1035153B (en) * | 1958-02-06 | 1958-07-31 | Bayer Ag | Process for the preparation of insecticidally active thiophosphoric acid esters |
DE1036846B (en) * | 1956-12-21 | 1958-08-21 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
US2854469A (en) * | 1956-03-02 | 1958-09-30 | Stauffer Chemical Co | Pesticidal composition of matter |
DE1056121B (en) * | 1957-02-27 | 1959-04-30 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
DE1062239B (en) * | 1956-07-28 | 1959-07-30 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
DE1063153B (en) * | 1956-12-10 | 1959-08-13 | Bayer Ag | Process for the preparation of esters of thiophosphoric acid containing sulfide, sulfoxide or sulfone groups |
DE1068699B (en) * | 1955-01-21 | 1959-11-12 | Sandoz A.G., Basel (Schweiz) | Process for the preparation of thiol or thionothiol phosphoric acid esters |
DE1083809B (en) * | 1957-06-14 | 1960-06-23 | Bayer Ag | Process for the preparation of thiolphosphoric acid esters |
DE1100019B (en) * | 1959-09-05 | 1961-02-23 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
DE1105231B (en) * | 1958-08-08 | 1961-04-20 | Ciba Geigy | Pest repellent with insecticidal and acaricidal effects |
DE1109672B (en) * | 1959-09-04 | 1961-06-29 | Bayer Ag | Process for the production of dithiolphosphoric acid esters |
DE1115243B (en) * | 1959-09-15 | 1961-10-19 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
DE1185858B (en) * | 1960-08-18 | 1965-01-21 | Basf Ag | Insecticides |
DE1212777B (en) * | 1963-11-07 | 1966-03-17 | Bayer Ag | Fungitoxic agents |
DE1213664B (en) * | 1963-10-19 | 1966-03-31 | Bayer Ag | Fungitoxic agents |
EP0027230A1 (en) * | 1979-10-13 | 1981-04-22 | Bayer Ag | Process for preparing thiophosphoric acid esters |
-
1950
- 1950-05-24 DE DEF1499A patent/DE830509C/en not_active Expired
Cited By (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE917668C (en) * | 1952-08-01 | 1954-09-09 | Bayer Ag | Process for the preparation of neutral esters of dithiophosphoric acid |
DE942988C (en) * | 1953-12-11 | 1956-05-09 | Bayer Ag | Process for the preparation of thiolphosphoric acid triesters |
US2891984A (en) * | 1954-06-10 | 1959-06-23 | Geigy Ag J R | New dithiophosphoric acid esters and their use for the control of mites |
DE957213C (en) * | 1954-06-10 | 1957-01-31 | Geigy Ag J R | Process for the preparation of new thiolthionophosphoric acid esters |
DE961083C (en) * | 1954-08-02 | 1957-04-04 | Bayer Ag | Process for the preparation of S-ª ‰ -Merkapto-aethyl-O, O-dialkyl-thiol-phosphoric acid esters |
DE1032247B (en) * | 1954-12-04 | 1958-06-19 | Bayer Ag | Process for the production of organic phosphorus compounds |
DE1014107B (en) * | 1954-12-28 | 1957-08-22 | Wolfen Filmfab Veb | Process for the preparation of esters of phosphorus-containing acids |
DE1068699B (en) * | 1955-01-21 | 1959-11-12 | Sandoz A.G., Basel (Schweiz) | Process for the preparation of thiol or thionothiol phosphoric acid esters |
DE964045C (en) * | 1955-05-14 | 1957-05-16 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
DE1018053B (en) * | 1955-10-29 | 1957-10-24 | Bayer Ag | Process for the preparation of S-chlorobenzyl esters of O, O-dialkyl-thiolphosphoric acid |
US2854469A (en) * | 1956-03-02 | 1958-09-30 | Stauffer Chemical Co | Pesticidal composition of matter |
DE1016260B (en) * | 1956-03-09 | 1957-09-26 | Bayer Ag | Process for the production of O, O-dialkyl-thiol-phosphoric acid-S-mercaptomethyl-triesters |
DE1062239B (en) * | 1956-07-28 | 1959-07-30 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
DE1063153B (en) * | 1956-12-10 | 1959-08-13 | Bayer Ag | Process for the preparation of esters of thiophosphoric acid containing sulfide, sulfoxide or sulfone groups |
DE1036846B (en) * | 1956-12-21 | 1958-08-21 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
DE1056121B (en) * | 1957-02-27 | 1959-04-30 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
DE1083809B (en) * | 1957-06-14 | 1960-06-23 | Bayer Ag | Process for the preparation of thiolphosphoric acid esters |
DE1035153B (en) * | 1958-02-06 | 1958-07-31 | Bayer Ag | Process for the preparation of insecticidally active thiophosphoric acid esters |
DE1105231B (en) * | 1958-08-08 | 1961-04-20 | Ciba Geigy | Pest repellent with insecticidal and acaricidal effects |
DE1109672B (en) * | 1959-09-04 | 1961-06-29 | Bayer Ag | Process for the production of dithiolphosphoric acid esters |
DE1136328B (en) * | 1959-09-04 | 1962-09-13 | Bayer Ag | Process for the production of dithiolphosphoric acid esters |
DE1100019B (en) * | 1959-09-05 | 1961-02-23 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
DE1115243B (en) * | 1959-09-15 | 1961-10-19 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
DE1185858B (en) * | 1960-08-18 | 1965-01-21 | Basf Ag | Insecticides |
DE1213664B (en) * | 1963-10-19 | 1966-03-31 | Bayer Ag | Fungitoxic agents |
DE1212777B (en) * | 1963-11-07 | 1966-03-17 | Bayer Ag | Fungitoxic agents |
US3357882A (en) * | 1963-11-07 | 1967-12-12 | Bayer Ag | Thiol-phosphoric acid esters fungitoxic agents |
EP0027230A1 (en) * | 1979-10-13 | 1981-04-22 | Bayer Ag | Process for preparing thiophosphoric acid esters |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE830509C (en) | Process for the preparation of neutral esters of thiophosphoric acid | |
DE807687C (en) | Process for the preparation of esters of phosphoric or thiophosphoric acid | |
DE836349C (en) | Process for the preparation of neutral esters of thiophosphoric acid | |
DE917668C (en) | Process for the preparation of neutral esters of dithiophosphoric acid | |
DE947368C (en) | Process for the preparation of esters of phosphoric and thiophosphoric acids containing sulfoxide groups | |
DE1052981B (en) | Process for the preparation of oxime phosphates | |
DE876691C (en) | Process for the preparation of dithiophosphoric acid esters | |
DE830508C (en) | Process for the preparation of neutral esters of thiophosphoric acid | |
DE818352C (en) | Process for the preparation of neutral esters of thiophosphoric acid | |
CH426776A (en) | Process for the preparation of O, O-dialkyl-S-alkylthiol phosphates | |
DE1062237B (en) | Process for the preparation of O, O-dialkylthiolphosphoric acid and -thiolthionophosphoric acid-S-gamma-cyanallyl esters | |
DE947369C (en) | Process for the production of neutral thionothiolphosphoric acid esters | |
DE871448C (en) | Process for the preparation of esters of monothiophosphoric acid | |
DE951717C (en) | Process for the production of thionothiol-phosphoric acid triesters | |
DE921870C (en) | Process for the preparation of 0, 0-dimethyl-0-4-nitro-3-chlorophenyl thiophosphate | |
DE961083C (en) | Process for the preparation of S-ª ‰ -Merkapto-aethyl-O, O-dialkyl-thiol-phosphoric acid esters | |
DE1215711B (en) | Process for the preparation of dialkyltin bis-phenolates | |
DE949650C (en) | Process for the preparation of derivatives of cyanophosphoric acid | |
DE962525C (en) | Process for the production of xanthogenic acid esters | |
DE1443264C (en) | Thiol or thionothiolphosphorus or -phosphonic acid esters and process for their preparation | |
DE1092464B (en) | Process for the preparation of O, S-dialkylthiophosphoric acid chlorides | |
DE1045391B (en) | Process for the preparation of thiophosphoric acid esters | |
DE964678C (en) | Process for the production of pest repellants | |
DE1129484B (en) | Process for the simultaneous production of substituted thioamides and thiophosphorus - (- one, -in) acid halides | |
DE954415C (en) | Process for the preparation of neutral esters of thiolphosphoric acid |