DE818352C - Process for the preparation of neutral esters of thiophosphoric acid - Google Patents
Process for the preparation of neutral esters of thiophosphoric acidInfo
- Publication number
- DE818352C DE818352C DEP41994A DEP0041994A DE818352C DE 818352 C DE818352 C DE 818352C DE P41994 A DEP41994 A DE P41994A DE P0041994 A DEP0041994 A DE P0041994A DE 818352 C DE818352 C DE 818352C
- Authority
- DE
- Germany
- Prior art keywords
- sodium
- thiophosphoric acid
- preparation
- acid
- neutral esters
- 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
- 238000000034 method Methods 0.000 title claims description 5
- 230000007935 neutral effect Effects 0.000 title claims description 5
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- -1 alkali metal salts Chemical class 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 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 12
- 229910052708 sodium Inorganic materials 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- 238000010626 work up procedure Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- OZQIAFAGANDINY-UHFFFAOYSA-N CCCCCCCCCCCC[S+]=P(O)(O)O Chemical compound CCCCCCCCCCCC[S+]=P(O)(O)O OZQIAFAGANDINY-UHFFFAOYSA-N 0.000 description 1
- IGMUCFGALMRFIK-UHFFFAOYSA-N CCCCCC[S+]=P(O)(O)O Chemical compound CCCCCC[S+]=P(O)(O)O IGMUCFGALMRFIK-UHFFFAOYSA-N 0.000 description 1
- HMANYETUONUMIX-UHFFFAOYSA-N CCC[S+]=P(O)(O)O Chemical compound CCC[S+]=P(O)(O)O HMANYETUONUMIX-UHFFFAOYSA-N 0.000 description 1
- BZYBZYFEGNHVLH-UHFFFAOYSA-N CC[S+]=P(O)(O)O Chemical compound CC[S+]=P(O)(O)O BZYBZYFEGNHVLH-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VXRRIYKDFNOWTC-UHFFFAOYSA-N OP(O)(O)=[S+]CC1=CC=CC=C1 Chemical compound OP(O)(O)=[S+]CC1=CC=CC=C1 VXRRIYKDFNOWTC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- ABNDFSOIUFLJAH-UHFFFAOYSA-N benzyl thiocyanate Chemical compound N#CSCC1=CC=CC=C1 ABNDFSOIUFLJAH-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- WFCLYEAZTHWNEH-UHFFFAOYSA-N ethylthiocyanate Chemical compound CCSC#N WFCLYEAZTHWNEH-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- VYHVQEYOFIYNJP-UHFFFAOYSA-N methyl thiocyanate Chemical compound CSC#N VYHVQEYOFIYNJP-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003580 thiophosphoric acid esters Chemical class 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
-
- 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
- A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
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
Verfahren zur Herstellung von neutralen Estern der Thiophosphorsäure Es ist bekannt, daß sich Salze der Thiophosphorsäureester folgender Konstitution: mit Alkylhalogeniden zu den entsprechenden neutralen Estern umsetzen lassen. In vielen Fällen führt dieses Verfahren aber nur dann zum Ziel, wenn als Salze die der Schwerrnetalle, wie Blei oder Silber, und als Alkylhalogenide die Jodide gewählt werden. Es wurde nun gefunden, daß sich die neutralen Ester der Thiophosphorsäure leicht herstellen lassen, wenn beliebige Alkylrhodanide, die im Alkylrest in beliebiger Weise substituiert sein können, mit den technisch leicht herstellbaren Alkalisalzen der Dialkylphosphite zur Umsetzung gebracht werden. Unter Abspaltung von Alkalicyanid bilden sich die gewünschten Ester. Es war nicht vorauszusehen, daß die Reaktion diesen Verlauf nehmen: würde. Das Schema der Reaktion ist folgendes: Die Alkylreste R können gleich oder verschieden sein. Es lassen sich nach dem neuen Verfahren Verbindungen herstellen, die sich durch stärkste kontaktinsektizide Wirkungen auszeichnen. An folgenden Beispielen soll das Wesen der neuen Reaktion erläutert werden. Beispiel i 70 g Diäthylphosphit werden Mit 2 ccm absolutem Alkohol vermischt und mit ioo ccm Toluol verdünnt. Auf diese Lösung läßt m-an 12 g Natrium einwirken. Nach dem Lösen des Natriums werden unter Rühren bei 40' 37 9 Methylrhodanid zugetropft. Man läßt noch 2 Stunden bei 40' rühren, gibt dann 15 ccm Wasser zu dem Reaktionsprodukt und trennt durch Filtrieren von den ausgeschiedenen Salzen. Das Filtrat wird fraktioniert. Man erhält 48 9 des S-Methylthiophosphorsäure-o,o-dimethylesters vom Kpl,4 112 bis 113'. Die Substanz ist wasserlöslich.Process for the preparation of neutral esters of thiophosphoric acid It is known that salts of thiophosphoric acid esters of the following constitution are: let react with alkyl halides to the corresponding neutral esters. In many cases, however, this process only works if the salts of heavy metals, such as lead or silver, and the iodides are selected as the alkyl halides. It has now been found that the neutral esters of thiophosphoric acid can be easily prepared if any alkyl rhodanides, which can be substituted in any way in the alkyl radical, are reacted with the alkali metal salts of dialkyl phosphites, which are easy to prepare industrially. The desired esters are formed with elimination of alkali metal cyanide. It was not foreseeable that the reaction would take this course: would. The scheme of the reaction is as follows: The alkyl radicals R can be identical or different. According to the new process, compounds can be produced which are characterized by the strongest contact insecticidal effects. The nature of the new reaction is to be explained using the following examples. Example i 70 g of diethyl phosphite are mixed with 2 cc of absolute alcohol and diluted with 100 cc of toluene. 12 g of sodium are allowed to act on this solution. After the sodium has dissolved, 37 9 of methyl rhodanide are added dropwise with stirring at 40 '. The mixture is stirred for a further 2 hours at 40 ', then 15 cc of water are added to the reaction product and the salts which have separated out are separated off by filtration. The filtrate is fractionated. Are obtained 48 9 of the S-Methylthiophosphorsäure-o, o-dimethyl ester from the Kpl, 4112-113 '. The substance is soluble in water.
Beispiel 2 Das wie in Beispiel i aus 12 g Natrium und 70 9 Diäthylphosphit in Benzol hergestellte N.atriumsalz wird unter Rühren auf 45 bis 5o' erwärmt. In ioMinuten läßt man unterKühlenbeiderangegebenen Temperatur 44 g Athylrhodanid- dazutropfen. Dann wird das Reaktionsgernisch noch i Stunde auf 55' erwärmt. Nach dem üblichen Aufarbeiten erhält man 35 g des S-Äthylthiophosphorsäure-o, o-diäthylesters vom Kp. 98'. Die neue Substanz ist begrenzt wasserlöslich.Example 2 The N sodium salt prepared as in Example 1 from 12 g of sodium and 70 % of diethyl phosphite in benzene is heated to 45 to 50 ° with stirring. In the course of 10 minutes, 44 g of ethylrhodanide are added dropwise while cooling at the stated temperature. The reaction mixture is then heated to 55 'for a further hour. After the usual work-up, 35 g of the S-ethylthiophosphoric acid o, o-diethyl ester with a boiling point of 98 'are obtained. The new substance has limited water solubility.
Beispiel 3 Auf das nach Beispiel i aus 12 g Natrium und 70 g Diäthylphosphit in Benzol hergestellte Natriumsalz läßt man bei 40' 52 g n-Prophylrhodanid einwirken. Das Reaktionsgernisch wird i Stunde bei 55' gehalten und dann wie üblich aufgearbeitet. Man erhält 40 g des S-Prophylthiophosphorsäureo, o-diäthylesters vom Kp, 103 bis io5'. Die Substanz ist wasserunlöslich. EXAMPLE 3 The sodium salt prepared in accordance with Example 1 from 12 g of sodium and 70 g of diethyl phosphite in benzene is allowed to act at 40 '52 g of n-prophylrhodanide. The reaction mixture is kept at 55 ' for 1 hour and then worked up as usual. 40 g of S-propylthiophosphoric acid, o-diethyl ester with a boiling point of 103 to io5 'are obtained. The substance is insoluble in water.
Beispiel 4 Auf das nach Beispiel i aus 12 g Natrium und 70 g Diäthyl-phosphit bereitete Natriumsalz läßt man 57,5 9 Isobutylrhodanid bei 40' einwirken. Man hält das Reaktionsgemisch i Stunde bei 55' und arbeitet dann in der üblichen Weise auf. Es werden 74g des S-Isobutylthiophosphorsäure-o, o-diäthylesters vom Kp", io51 erhalten. Die Substanz ist wasserunlöslich.Example 4 The sodium salt prepared according to Example 1 from 12 g of sodium and 70 g of diethyl phosphite is allowed to act at 57.5 g of isobutylrhodanide at 40 '. The reaction mixture is kept at 55 'for 1 hour and then worked up in the usual manner. There are 74g of S-Isobutylthiophosphorsäure-o, o-diäthylesters of boiling point, "receive io51. The substance is water insoluble.
B eispiel 5 Auf das nach Beispiel i aus 12 g Natrium und 70 g Diäthylphosphit hergestellte Natriumsalz läßt man 65 g n-Hexylrhodanid bei 4o' einwirken. Man erwärmt i Stunde bei 55 bis 6o' und arbeitet dann in üblicher Weise auf. Es werden 48 g des S-Hexylthiophosphorsäure-o, o-diäthylesters vom Kp, 125 bis 130' erhalten.EXAMPLE 5 65 g of n-hexylrhodanide are allowed to act at 40 'on the sodium salt prepared according to Example 1 from 12 g of sodium and 70 g of diethyl phosphite. The mixture is heated at 55 to 60 'for 1 hour and then worked up in the usual way. 48 g of S-hexylthiophosphoric acid o, o-diethyl ester with a bp 125 to 130 ' are obtained.
Beispiel 6 Auf das nach Beispiel i aus 12 g Natrium und 70 g Diäthylphosphit hergestellte Natriumsalz läßt man bei 5o' i 15 g Dodecylrhodanid einwirken. Man hält i Stunde bei 55 bis 60' und arbeitet dann in der üblichen Weise auf. Es werden 6o g des S-Dodecylthiophosphorsäure-o, o-diäthylesters vom Kpo"5 185 bis igo' erhalten. EXAMPLE 6 The sodium salt prepared according to Example 1 from 12 g of sodium and 70 g of diethyl phosphite is allowed to act at 50 '1 5 g of dodecyl rhodanide. It is held at 55 to 60 minutes for an hour and then worked up in the usual way. 60 g of the S-dodecylthiophosphoric acid o, o-diethyl ester from Kpo "5 185 to igo 'are obtained.
Beispiel 7 Das nach Beispiel i aus 12 g Natrium und 70 9 Diäthylphosphit hergestellte Natriumsalz wird auf 45' erwärmt. Bei dieser Temperatur läßt man unter Rühren 76 g Benzylrhodanid zutropfen. Man hält 3/2 Stunde auf 40' und arbeitet dann in üblicher Weise auf. Man erhält 70 g des S-Benzylthiophosphorsäure-o, o-diäthylesters vom KP2 165 bis 170'. Beispiel 8 Auf das gemäß Beispiel i aus io g Natrium, 75 ccm Benzol und 56 g Diäthylphosphit in Gegenwart von 2 ccm absolutem Alkohol hergestellte Natriumsalz läßt man 29 g des in 250 ccm Benzol ge- lösten Athylen-dirhodanids bei 5o' eintropfen. Man hält i Stunde bei 6o' und arbeitet dann in der üb- lichen Weise auf. Es werden 15 g des S-Äthylendithiophosphorsäure-o,o-diäthylestersvomKpo"q igo9 erhalten. Die Substanz ist wasserunlöslich.Example 7 The sodium salt prepared according to Example 1 from 12 g of sodium and 70 % of diethyl phosphite is heated to 45 °. At this temperature, 76 g of benzyl rhodanide are added dropwise with stirring. It is held at 40 'for 3/2 hour and then worked up in the usual way. 70 g of the S-benzylthiophosphoric acid o, o-diethyl ester of KP2 165 to 170 'are obtained. Example 8 In the accordance of i io g sodium, 75 cc of benzene and 56 g of diethyl phosphite in the presence of 2 cc absolute alcohol sodium salt prepared is allowed dropwise 29 g of the sample in 250 cc of benzene overall dissolved ethylene-dirhodanids at 5o '. Hold at 60 'for an hour and then work up in the usual way. 15 g of the S-ethylenedithiophosphoric acid o, o-diethyl ester from Kpo "q igo9 are obtained. The substance is insoluble in water.
Beispiel 9 7 g Natrium werden in i5o ccm Toluol. angeschlämmt. Dazu gibt man 42 g Diäthylphosphit und rührt bei 4o bis 5o' so lange, bis alles Natrium in Lösung gegangen ist. Dann tropft man unter Rühren 44 g fl-Äthylmercaptoäthylrhodanid (Kp, go') bei 40' ein. Man hält i Stunde bei 5o' und arbeitet dann wie üblich auf. Es werden 28 g des S-ß-Äthylrnercaptoäthylthiophosphorsäure - o, o - diäthylesters vom Kp, 137 bis 14C erhalten. Es handelt sich um ein wasserunlösliches, hellgelbes 01. Example 9 7 g of sodium are dissolved in 150 cc of toluene. slurried. 42 g of diethyl phosphite are added and the mixture is stirred at 40 to 50 'until all of the sodium has dissolved. 44 g of fl-ethylmercaptoethylrhodanide (bp, go ') are then added dropwise with stirring at 40'. You hold it at 50 'for an hour and then work up as usual. 28 g of S-ß-Äthylrnercaptoäthylthiophosphorsäure - o, o - diethyl ester of bp 137 to 14C are obtained. It is a water-insoluble, light yellow 01.
Beispiel io In die nach Beispiel 9 hergestellte Natriumlösung tropft man unter Rühren bei 40' 40 9 ß-Methylmercaptoäthylrhodanid. Dann hält man die Ternperatur-noch i Stunde bei 5o' und arbeitet wie üb- lich auf. Man erhält 34 g des S-fl-Methylmercaptoäthylthiophosphorsäure-o, o-diäthylesters vom Kpi, 134 bis 138'. Die nach den Beispielen 9 und io erhaltenen neuen Substanzen zeichnen sich durch außerordentlich starke kontaktinsektizide Wirkungen aus.Example 10 ß-Methylmercaptoethylrhodanide is added dropwise to the sodium solution prepared according to Example 9 , while stirring at 40 '40 9. Then keep the temperature at 50 'for another hour and work up as usual . 34 g of S-fl-methylmercaptoethylthiophosphoric acid-o, o-diethyl ester of Kpi, 134 to 138 'are obtained. The new substances obtained according to Examples 9 and 10 are distinguished by extremely strong contact insecticidal effects.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP41994A DE818352C (en) | 1949-05-07 | 1949-05-08 | Process for the preparation of neutral esters of thiophosphoric acid |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE691374X | 1949-05-07 | ||
| DEP41994A DE818352C (en) | 1949-05-07 | 1949-05-08 | Process for the preparation of neutral esters of thiophosphoric acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE818352C true DE818352C (en) | 1951-10-25 |
Family
ID=25946323
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP41994A Expired DE818352C (en) | 1949-05-07 | 1949-05-08 | Process for the preparation of neutral esters of thiophosphoric acid |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE818352C (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE946056C (en) * | 1953-12-19 | 1956-07-26 | Bayer Ag | Process for the preparation of neutral esters of thiolphosphoric acid |
| DE954415C (en) * | 1953-12-19 | 1956-12-20 | Bayer Ag | Process for the preparation of neutral esters of thiolphosphoric acid |
| 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 |
| DE1014107B (en) * | 1954-12-28 | 1957-08-22 | Wolfen Filmfab Veb | Process for the preparation of esters of phosphorus-containing acids |
| DE1032247B (en) * | 1954-12-04 | 1958-06-19 | Bayer Ag | Process for the production of organic phosphorus compounds |
| DE1087591B (en) * | 1958-11-07 | 1960-08-25 | Bayer Ag | Process for the preparation of dithiophosphoric acid esters |
-
1949
- 1949-05-08 DE DEP41994A patent/DE818352C/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE946056C (en) * | 1953-12-19 | 1956-07-26 | Bayer Ag | Process for the preparation of neutral esters of thiolphosphoric acid |
| DE954415C (en) * | 1953-12-19 | 1956-12-20 | Bayer Ag | Process for the preparation of neutral esters of thiolphosphoric acid |
| 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 |
| DE1087591B (en) * | 1958-11-07 | 1960-08-25 | Bayer Ag | Process for the preparation of dithiophosphoric acid esters |
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