DE1022579B - Process for the preparation of insecticidally active thiophosphoric acid esters or dithiophosphoric acid esters - Google Patents
Process for the preparation of insecticidally active thiophosphoric acid esters or dithiophosphoric acid estersInfo
- Publication number
- DE1022579B DE1022579B DEF20108A DEF0020108A DE1022579B DE 1022579 B DE1022579 B DE 1022579B DE F20108 A DEF20108 A DE F20108A DE F0020108 A DEF0020108 A DE F0020108A DE 1022579 B DE1022579 B DE 1022579B
- Authority
- DE
- Germany
- Prior art keywords
- acid esters
- preparation
- dithiophosphoric acid
- insecticidally active
- 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
Links
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 150000003580 thiophosphoric acid esters Chemical class 0.000 title 1
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 claims description 5
- 150000003863 ammonium salts Chemical class 0.000 claims description 5
- -1 alkyl radicals Chemical class 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical class NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 241000700159 Rattus Species 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241001124076 Aphididae Species 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 241001454295 Tetranychidae Species 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 231100000518 lethal Toxicity 0.000 description 3
- 230000001665 lethal effect Effects 0.000 description 3
- AYETZOVOIOQESV-UHFFFAOYSA-N n-acetyl-2-chloroacetamide Chemical compound CC(=O)NC(=O)CCl AYETZOVOIOQESV-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- MFPAFLUPDLDNJL-UHFFFAOYSA-N 4-chloro-n-(2-chloroacetyl)benzamide Chemical compound ClCC(=O)NC(=O)C1=CC=C(Cl)C=C1 MFPAFLUPDLDNJL-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- ZDAYXLBYGPADRK-UHFFFAOYSA-N n-(2-chloroacetyl)benzamide Chemical compound ClCC(=O)NC(=O)C1=CC=CC=C1 ZDAYXLBYGPADRK-UHFFFAOYSA-N 0.000 description 2
- 230000003151 ovacidal effect Effects 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241000239290 Araneae Species 0.000 description 1
- CZGGKXNYNPJFAX-UHFFFAOYSA-N Dimethyldithiophosphate Chemical group COP(S)(=S)OC CZGGKXNYNPJFAX-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 150000003855 acyl compounds Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000009885 systemic effect Effects 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
- 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
-
- 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
DEUTSCHESGERMAN
Acylverbindungen des Chloracetamids der allgemeinen FormelAcyl compounds of chloroacetamide of the general formula
R — CO — NH — CO — CH2 — ClR - CO - NH - CO - CH 2 - Cl
in der R für einen beliebig substituierten Alkyl- oder Arylrest steht, sind bekannt.in which R stands for any substituted alkyl or aryl radical are known.
IDs wurde nun gefunden, daß sich die genannten Verbindungen leicht mit den Alkali- bzw. Ammoniumsalzen der Thio- bzw. Dithiophosphorsäure-O.O-dialkylester umsetzen lassen, wobei Phosphorsäureester folgender allgemeiner Konstitution erhalten werden:IDs have now been found that the compounds mentioned easily react with the alkali or ammonium salts the thio- or dithiophosphoric acid O.O-dialkyl ester let react, whereby phosphoric acid esters of the following general constitution are obtained:
R —CO—NH —CO-CH9-S-P-R —CO — NH —CO-CH 9 -SP-
O (S)
OR1
OR,O (S)
OR 1
OR,
Verfahren zur Herstellung von insektizid wirksamen Thiophosphorsäure-
bzw. DithiophosphorsäureesternProcess for the production of insecticidally active thiophosphoric acid
or dithiophosphoric acid esters
Anmelder:Applicant:
Farbenfabriken Bayer Aktiengesellschaft, Leverkusen-BayerwerkPaint factories Bayer Aktiengesellschaft, Leverkusen-Bayerwerk
Dr. Gerhard Schrader, Wuppertal-Cronenberg,Dr. Gerhard Schrader, Wuppertal-Cronenberg,
und Dr. Walter Lorenz, Wuppertal-Elberfeld,and Dr. Walter Lorenz, Wuppertal-Elberfeld,
sind als Erfinder genannt wordenhave been named as inventors
in denen R die oben angegebene Bedeutung hat und worin R1 und R2 für Alkylreste mit höchstens 4 C-Atomen stehen.in which R has the meaning given above and in which R 1 and R 2 are alkyl radicals with a maximum of 4 carbon atoms.
Die neuen Phosphorsäureester zeichnen sich bei geringer Toxizität gegen Warmblüter durch eine hervorragende Wirkung gegen Spinnmilben aus. Es ist besonders hervorzuheben, daß in der genannten Stoffklasse Verbindungen zu finden sind, die eine ausgesprochene ovizide Wirkung bei Spinnmilben besitzen. Zum Teil haben die Verbindungen auch eine innertherapeutische Wirkung bei lebenden Pflanzen.The new phosphoric acid esters are characterized by an excellent, low toxicity against warm-blooded animals Effect against spider mites. It should be particularly emphasized that in the class of substances mentioned Compounds can be found that have a pronounced ovicidal effect on spider mites. Partly the compounds also have an therapeutic effect on living plants.
CH^-CO-NH-CO-CHo-S-PCH ^ -CO-NH-CO-CHo-S-P
OC2H5 OC 2 H 5
OCH,OCH,
CH3-Cp-NH-CO-CH2-S-PCH 3 -Cp-NH-CO-CH 2 -SP
OCH,OCH,
OCH,OCH,
68 g N-Acetyl-chloracetamid werden in 250 ecm 50%-igem Alkohol gelöst (0,5 Mol). Bei 50° tropft man nun eine wäßrige Lösung zu, die 0,5 Mol des Natriumsalzes des Dithiophosphorsäure-O,O-dimethylesters enthält. Man erwärmt 1 Stunde auf 60° und arbeitet dann, wie im Beispiel 1 angegeben, auf. Es werden 64 g des neuen Esters, entsprechend 50% der Theorie, erhalten.68 g of N-acetyl-chloroacetamide are in 250 ecm 50% Dissolved alcohol (0.5 mol). An aqueous solution containing 0.5 mol of the sodium salt is then added dropwise at 50 ° of the dithiophosphoric acid O, O-dimethyl ester. The mixture is heated to 60 ° for 1 hour and then works as indicated in Example 1 on. 64 g of the new ester, corresponding to 50% of theory, are obtained.
1000 mg/kg des neuen Esters zeigen an der Ratte per os nur vereinzelte Todesfälle. 0,01 %ige wäßrige Lösungen töten Blattläuse zu 100% ab. Die Verbindung zeigt eine ausgesprochene innertherapeutische Wirkung.1000 mg / kg of the new ester showed only isolated deaths in rats orally. 0.01% aqueous solutions kill aphids 100%. The compound shows a pronounced internal therapeutic effect.
56 g N-Acetylchloracetamid (Fp. 105°; 0,41 Mol) werden in 200 ecm 50%igem Alkohol gelöst. Dazu tropft man eine wäßrige Lösung, die 0,41 Mol des Natriumsalzes des Dithiophosphorsäure-0,0-diäthylesters enthält. Innerhalb einer Stunde erwärmt man unter Rühren auf 60°. Man hält die Temperatur noch 1 Stunde bei 60° und kühlt dann ab. Das Reaktionsprodukt wird mit 50 ecm Benzol durchgeschüttelt. Die Benzollösung wird abgetrennt, mit Wasser gewaschen und dann mit Natriumsulfat getrocknet. Nach dem Abdestillieren des Benzols bleiben 83 g des neuen Esters als gelbes, wasserunlösliches Öl zurück. Ausbeute 71 % der Theorie.56 g of N-acetylchloroacetamide (melting point 105 °; 0.41 mol) are dissolved in 200 ecm 50% alcohol. An aqueous solution containing 0.41 mol of the sodium salt is added dropwise of the dithiophosphoric acid-0,0-diethyl ester contains. The mixture is heated to 60 ° over the course of an hour while stirring. The temperature is kept at 60 ° for a further hour and then cooled. The reaction product is with 50 ecm Benzene shaken. The benzene solution is separated off, washed with water and then with sodium sulfate dried. After the benzene has been distilled off, 83 g of the new ester remain as a yellow, water-insoluble ester Oil back. Yield 71% of theory.
An der Ratte per os wirken erst 250 mg/kg der neuen Verbindung tödlich. 0,01 %ige Lösungen töten mit Sicherheit Blattläuse ab. Spinnmilben und Spinnmilbeneier werden mit 0,01%igen Lösungen sicher abgetötet.Only 250 mg / kg of the new compound are lethal in rats per os. 0.01% solutions kill with Safety aphids off. Spider mites and spider mite eggs are safely killed with 0.01% solutions.
CH,-CO-NH-CO-CH0-S-PCH, -CO-NH-CO-CH 0 -SP
OCoH,OCoH,
27 g N-Acetyl-chloracetamid (0,2 Mol) werden in 200 ecm 50%igem Alkohol gelöst. Dazu gibt man 38 g des Ammoniumsalzes des Thiophosphorsäure-O.O-diäthylesters, das in 200 ecm Wasser gelöst ist. Unter Rühren hält man die Temperatur 1 Stunde bei 60°. Dann kühlt man auf Zimmertemperatur ab, verdünnt mit Eiswasser und nimmt das ausgeschiedene Öl in Äther auf. Nach dem Trocknen der Ätherlösung wird der Äther im Vakuum abdestilliert. Es bleiben 45 g des neuen Esters als wasserunlösliches Öl zurück.27 g of N-acetyl-chloroacetamide (0.2 mol) are dissolved in 200 ecm of 50% alcohol. Add 38 g of the ammonium salt of thiophosphoric acid O.O-diethyl ester, which is dissolved in 200 ecm of water. The temperature is maintained at 60 ° for 1 hour while stirring. Then cool it is reduced to room temperature, diluted with ice water and the separated oil is taken up in ether. To After drying the ethereal solution, the ether is distilled off in vacuo. There remain 45 g of the new ester as water-insoluble oil back.
709 849/412709 849/412
An der Ratte per os wirkt die Verbindung mit 50 mg/kg tödlich. 0,01 %ige Lösungen töten mit Sicherheit Blattläuse ab. O,l°/Oige Lösungen haben bei Spinnmilben eine 100°/oige ovizide Wirkung. Außerdem zeigt die Verbindung starke innertherapeutische Wirkung.The compound is lethal at 50 mg / kg in rats orally. 0.01% solutions are sure to kill aphids. O, l ° / O by weight solutions have a spider mites at 100 ° / o strength ovicidal action. In addition, the compound shows a strong therapeutic effect.
-C-NH-CO-CH0-S-P-C-NH-CO-CH 0 -SP
OC2H5 OC 2 H 5
-C-NH-CO-CH9-S-P-C-NH-CO-CH 9 -SP
OCoH,OCoH,
OC9Hn In eine konzentriert wäßrige Lösung, die 0,2 Mol des Natriumsalzes des Dithiophosphorsäure-0,0-diäthylesters enthält, werden bei 50° 46 g (0,2 Mol) N-Chloracetylp-chlorbenzamid eingetragen. Nach 3 Stunden Stehenlassen bei 60° arbeitet man in der oben beschriebenen Weise auf Fp. (aus Benzol — Petroläther) 127 bis 128°. Ausbeute: 72 g, das sind 95 °/0 der Theorie.OC 9 H n 46 g (0.2 mol) of N-chloroacetylp-chlorobenzamide are introduced into a concentrated aqueous solution containing 0.2 mol of the sodium salt of dithiophosphoric acid 0,0-diethyl ester at 50 °. After standing at 60 ° for 3 hours, the process is carried out in the manner described above to melting point (from benzene-petroleum ether) 127 ° to 128 °. Yield: 72 g, that is 95 ° / 0 of theory.
An der Ratte per os wirkt die Verbindung noch mit 100 mg'kg vereinzelt tödlich.The compound is still fatal in isolated cases at 100 mg / kg in rats per os.
1515th
Zu einer konzentriert wäßrigen Lösung, die 0,25 Mol des Natriumsalzes des Dithiophosphorsäure-OjO-diäthylesters enthält, werden 300 ecm Aceton gegeben. Man erwärmt auf 50° und gibt dann 49 g (0,25 Mol) N-Chloracetyl-benzamid hinzu. Nach 3 Stunden Stehen bei 60° kühlt man ab, verdünnt mit Eiswasser und trennt das ausgeschiedene Öl ab. Man äthert die wäßrige Lösung gut aus, gibt die Ätherschicht zum abgetrennten Öl und trocknet diese Ätherlösung mit Natriumsulfat. Man filtriert und destilliert den Äther ab. Das Produkt erstarrt. Fp. (aus Essigester) 79°. Ausbeute: 70 g, das sind 80% der Theorie.To a concentrated aqueous solution containing 0.25 mol of the sodium salt of dithiophosphoric acid-OjO-diethyl ester contains, 300 ecm of acetone are given. The mixture is heated to 50 ° and then 49 g (0.25 mol) of N-chloroacetylbenzamide are added added. After standing at 60 ° for 3 hours, the mixture is cooled, diluted with ice water and separated excreted oil. The aqueous solution is thoroughly etherified, the ether layer is added to the separated oil and dries this ethereal solution with sodium sulfate. It is filtered and the ether is distilled off. The product solidifies. Mp (from ethyl acetate) 79 °. Yield: 70 g, that is 80% of theory.
An der Ratte per os wirkt die Verbindung mit 250 mg/kg tödlich. 0,l%ige Lösungen besitzen noch eine systemische Wirkung gegenüber Blattläusen.The compound is lethal at 250 mg / kg in rats orally. 0.1% solutions still have a systemic one Effect on aphids.
Cl-Cl-
O OO O
!! il!! il
-C-NH-CO-CH2-S-P-C-NH-CO-CH 2 -SP
OC2H5 OC 2 H 5
OC2H5 OC 2 H 5
In 400 ecm Aceton werden 57 g (0,3 Mol) des Ammoniumsalzes des Thiophosphorsäure-0,0-diäthylesters gelöst und bei 50° 59 g (0,3 Mol) N-Chloracetylbenzamid zugegeben. Man erwärmt noch 3 Stunden auf 60°, kühlt ab, verdünnt mit Eiswasser und arbeitet in der oben beschriebenen Weise auf. Die Umkristallisation erfolgt am besten aus Essigester — Petroläther. Fp. 56 bis 58°. Ausbeute: 51 g, das sind 51 % der Theorie.57 g (0.3 mol) of the ammonium salt are dissolved in 400 ecm of acetone of the thiophosphoric acid-0,0-diethyl ester dissolved and at 50 ° 59 g (0.3 mol) of N-chloroacetylbenzamide admitted. The mixture is heated to 60 ° for a further 3 hours, cooled, diluted with ice water and worked in the above described way. Recrystallization is best done from ethyl acetate - petroleum ether. Mp. 56 to 58 °. Yield: 51 g, that is 51% of theory.
Ratten werden per os mit 100 mg/kg abgetötet. 0,l%ige Lösungen töten Blattläuse und Spinnmilben zu 100% ab. Außerdem zeigt die Verbindung innertherapeutische Wirkung.Rats are killed orally at 100 mg / kg. 0.1% solutions kill aphids and spider mites 100% off. In addition, the compound shows a therapeutic effect.
38 g (0,2 Mol) des Ammoniumsalzes des Thiophosphorsäure-O,O-diäthylesters werden in 300 ecm Aceton gelöst. Bei 45° werden 46 g (0,2 Mol) N-Chloracetyl-p-chlorbenzamid eingetragen. Man hält die Temperatur noch 3 Stunden bei 60° und arbeitet dann in gewohnter Weise auf. Das erhaltene Öl erstarrt nach einiger Zeit. Fp. (aus Benzol — Petroläther) 72 bis 75°. Ausbeute: 55 g, das sind 75 % der Theorie.38 g (0.2 mol) of the ammonium salt of thiophosphoric acid O, O-diethyl ester are dissolved in 300 ecm acetone. At 45 ° there are 46 g (0.2 mol) of N-chloroacetyl-p-chlorobenzamide registered. The temperature is kept at 60 ° for a further 3 hours and then worked in the usual way on. The oil obtained solidifies after a while. Mp. (From benzene - petroleum ether) 72 to 75 °. Yield: 55 g, that are 75% of theory.
An der Ratte per os wirken 50 mg/kg noch mit Sicherheit tödlich. O,l%ige Lösungen töten Blattläuse zu 100% ab, die Verbindung zeigt außerdem innertherapeutische Wirkung.In rats per os, 50 mg / kg are definitely fatal. 0.1% solutions kill aphids 100% off, the compound also shows an internal therapeutic effect.
Claims (1)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF20108A DE1022579B (en) | 1956-04-21 | 1956-04-21 | Process for the preparation of insecticidally active thiophosphoric acid esters or dithiophosphoric acid esters |
| NL216389A NL107328C (en) | 1956-04-21 | 1957-04-16 | |
| GB1297457A GB808259A (en) | 1956-04-21 | 1957-04-23 | Thiophosphoric acid esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF20108A DE1022579B (en) | 1956-04-21 | 1956-04-21 | Process for the preparation of insecticidally active thiophosphoric acid esters or dithiophosphoric acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1022579B true DE1022579B (en) | 1958-01-16 |
Family
ID=7089559
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF20108A Pending DE1022579B (en) | 1956-04-21 | 1956-04-21 | Process for the preparation of insecticidally active thiophosphoric acid esters or dithiophosphoric acid esters |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1022579B (en) |
| GB (1) | GB808259A (en) |
| NL (1) | NL107328C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3013940A (en) * | 1957-06-03 | 1961-12-19 | Montedison Spa | Organo-mercapto-methyleneamides of o, o-dialkyl-thio(or dithio)-phosphorylacetic acids having pesticidal activity |
| DE1183082B (en) * | 1963-07-17 | 1964-12-10 | Bayer Ag | Process for the production of thiol or thionothiolphosphonic acid esters |
| DE1194633B (en) * | 1960-02-24 | 1965-06-10 | Ciba Geigy | Insecticidal and acaricidal agents |
-
1956
- 1956-04-21 DE DEF20108A patent/DE1022579B/en active Pending
-
1957
- 1957-04-16 NL NL216389A patent/NL107328C/xx active
- 1957-04-23 GB GB1297457A patent/GB808259A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3013940A (en) * | 1957-06-03 | 1961-12-19 | Montedison Spa | Organo-mercapto-methyleneamides of o, o-dialkyl-thio(or dithio)-phosphorylacetic acids having pesticidal activity |
| DE1194633B (en) * | 1960-02-24 | 1965-06-10 | Ciba Geigy | Insecticidal and acaricidal agents |
| DE1183082B (en) * | 1963-07-17 | 1964-12-10 | Bayer Ag | Process for the production of thiol or thionothiolphosphonic acid esters |
Also Published As
| Publication number | Publication date |
|---|---|
| GB808259A (en) | 1959-01-28 |
| NL107328C (en) | 1964-01-17 |
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