DE1063148B - Process for the preparation of O, O-dialkyl-S-propargyl-thio- or -dithiophosphoric acid esters - Google Patents
Process for the preparation of O, O-dialkyl-S-propargyl-thio- or -dithiophosphoric acid estersInfo
- Publication number
- DE1063148B DE1063148B DEF24013A DEF0024013A DE1063148B DE 1063148 B DE1063148 B DE 1063148B DE F24013 A DEF24013 A DE F24013A DE F0024013 A DEF0024013 A DE F0024013A DE 1063148 B DE1063148 B DE 1063148B
- Authority
- DE
- Germany
- Prior art keywords
- propargyl
- thio
- dialkyl
- acid esters
- dithiophosphoric acid
- 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 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 229910052760 oxygen Inorganic materials 0.000 title description 2
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims 1
- 125000003186 propargylic group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- 241001454295 Tetranychidae Species 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 3
- -1 propargyl halides Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 241000256113 Culicidae Species 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241000109852 Macrosiphoniella sanborni Species 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
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/173—Esters of thiophosphoric acids with unsaturated acyclic alcohols
-
- 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
DEUTSCHESGERMAN
DEUTSCHLANDGERMANY
PATENTAMTPATENT OFFICE
kl. kl.
F24013IVb/12oF24013IVb / 12o
ANMELDE TA G: 24. SEPTEMBER 1957REGISTRATION DAY: SEPTEMBER 24, 1957
B EKANNTMACHUNG PER ANMELDUNG UND AUSGABE DER AUSLEGESCHRIFT:NOTICE BY REGISTRATION AND ISSUE OF THE EDITORIAL:
13. AIJ G U ST 19 S 913. AIJ G U ST 19 S 9
Die Erfindung betrifft ein Verfahren zur Herstellung von 0,0-Dialkyl-S-propargyl-thio- oder -dithiophosphorsäureestern der allgemeinen FormelThe invention relates to a process for the preparation of 0,0-dialkyl-S-propargyl-thio- or -dithiophosphoric acid esters the general formula
RORO
RORO
O (S)O (S)
Verfahren zur HerstellungMethod of manufacture
von O.O-Dialkyl-S-propargyl-thio- oder -dithiophosphorsäureesternof O.O-Dialkyl-S-propargyl-thio- or phosphorodithioic acid esters
in welcher R für bevorzugt niedere Alkylreste steht.in which R is preferably lower alkyl radicals.
Die Herstellung dieser Verbindung geschieht nach an sich bekannten Methoden durch Umsetzung von Propargylhalogeniden, insbesondere Propargylchlorid oder Propargylbromid, mit Salzen von Ο,Ο-Dialkylthio- oder -dithiophosphorsäuren. Geeignete Salze sind beispielsweise die Alkalisalze, besonders jedoch die leicht zugänglichen Ammoniumsalze der obengenannten Säuren. Die erfindungsgemäßen Verbindungen zeichnen sich durch eine gute Spinnmilben- und Blattläusewirkung aus und besitzen zum Teil svstemische Eigenschaften. Sie werden in der für andere Phosphorsäureester üblichen Art und Weise angewandt, d. h. bevorzugt in Verbindung mit den üblichen festen oder flüssigen Streck- bzw. Verdünnungsmitteln. Feste Streckmittel sind z. B. Talkum, Kreide, Bentonit, Tonerde, Kaolin. Als flüssiges Verdünnungsmittel kommt vor allem Wasser in Frage, worin die obengenannten Verbindungen zweckmäßig unter Verwendung eines Hilfslösemittels, wie Dimethylformamid oder Aceton, und eines handelsüblichen ümulgators einemulgiert werden.This compound is prepared by methods known per se by reacting propargyl halides, in particular propargyl chloride or propargyl bromide, with salts of Ο, Ο-dialkylthio- or dithiophosphoric acids. Suitable salts are, for example, the alkali metal salts, but especially the readily available ammonium salts of the abovementioned acids. The compounds according to the invention are distinguished by a good action of spider mites and aphids and some of them have synthetic properties. They are used in the manner customary for other phosphoric acid esters, ie preferably in conjunction with the customary solid or liquid extenders or diluents. Solid extenders are e.g. B. talc, chalk, bentonite, clay, kaolin. A particularly suitable liquid diluent is water, into which the abovementioned compounds are expediently emulsified using an auxiliary solvent, such as dimethylformamide or acetone, and a commercially available emulsifier.
Aus der USA.-Patentschrift 2 693 483 sind Thionophosphorsäureester bekannt, die neben einem sauerstoffgebundenen Propargylesterrest einen Trichlorphenylesterrest im Molekül enthalten. Während die erfindungsgemäß erhältlichen Verbindungen eine ausgezeichnete insektizide Wirkung gegen Kartoffelkäfer, Fliegen, Blattläuse, Spinnmilben und Mttckenlarven besitzen, kommt diese breite insektizide Wirkung den aus der LJSA.-Patentschrift 2 693 483 bekannten Verbindungen nicht zu. Darüber hinaus besitzen die erfindungsgemäß erhältlichen Verbindungen eine systemische Wirksamkeit, d. h., sie vermögen aus dem Pflanzensystem heraus fressende Insekten abzutöten, wenn wäßrige Emulsionen der erfindungsgemäß erhältKchen Verbindungen über die Wurzeln von den zu schützenden Pflanzen aufgenommen werden. Eine solche Wirksamkeit geht den Verbindungen der obengenannten USA.-Patentschrift ab.US Pat. No. 2,693,483 discloses thionophosphoric acid esters which, in addition to an oxygen-bound propargyl ester residue, contain a trichlorophenyl ester residue in the molecule. While the compounds obtainable according to the invention have an excellent insecticidal effect against potato beetles, flies, aphids, spider mites and mosquito larvae, the compounds known from LJSA. Patent 2,693,483 do not have this broad insecticidal effect. In addition, the compounds obtainable according to the invention have a systemic activity, ie they are able to kill insects eating out of the plant system if aqueous emulsions of the compounds obtained according to the invention are taken up via the roots of the plants to be protected. The compounds of the above-mentioned USA patent specification lack such effectiveness.
Anmelder:Applicant:
Farbenfabriken Bayer Aktiengesellsdiaft, Leverkusen-BayerwerkFarbenfabriken Bayer Aktiengesellsdiaft, Leverkusen-Bayerwerk
Dr. Dr. h. c. Gerhard Schrader, Wuppertal-Cronenberg, ist als Erfinder genannt wordenDr. Dr. H. c. Gerhard Schrader, Wuppertal-Cronenberg, has been named as the inventor
»5 Sl g des Ammoniumsalzes der Ο,Ο-Diäthyldithiophosphorsäure werden in 150 ecm Methyläthylketon gelöst. Bei 800C werden 19 g Propargylchlorid zugetropft. Die Temperatur wird 1 Stunde beibehalten, wobei die Reaktion unter ständigem Rühren beendet wird. Nach Absaugen vom gebildeten Ammoniumchlorid wird das Lösemittel abdestilliert, der Rückstand in Äther aufgenommen und die ätherische Schicht zweimal mit je SO ecm Wasser gewaschen. Nach dem Trocknen der ätherischen Schicht mit Natriumsulfat wird der Äther abdestilliert und der Rückstand im Hochvakuum rektifiziert. Der Ester siedet bei 0,1 mm bei 660C. Die Ausbeute beträgt 4Ig = 73°/„ der Theorie.»5 Sl g of the ammonium salt of Ο, Ο-diethyldithiophosphoric acid are dissolved in 150 ecm of methyl ethyl ketone. At 80 ° C., 19 g of propargyl chloride are added dropwise. The temperature is maintained for 1 hour, the reaction being terminated with constant stirring. After the ammonium chloride formed has been filtered off with suction, the solvent is distilled off, the residue is taken up in ether and the ethereal layer is washed twice with 50% of water each time. After the ethereal layer has been dried with sodium sulfate, the ether is distilled off and the residue is rectified in a high vacuum. The ester boils at 0.1 mm at 66 0 C. The yield is 4Ig = 73 ° / "of the theoretical.
C2H8O,C 2 H 8 O,
P — S — CH2 — C = CHP - S - CH 2 - C = CH
C2H6O1 C 2 H 6 O 1
C2H8O'C 2 H 8 O '
P-S-CH2-C=CH C2H6O'PS-CH 2 -C = CH C 2 H 6 O '
41 g des Ammoniumsalzes der O.O-Diäthylthiolphosphorsäure werden in 125 ecm Äthanol gelöst. Bei 70° C werden sodann 20 g Propargylchlorid zugegeben. Unter beständigem Rühren wird bei der gleichen Temperatur innerhalb einer Stunde die Reaktion vervollständigt.41 g of the ammonium salt of O.O-diethylthiolphosphoric acid are dissolved in 125 ecm of ethanol. At 70 ° C., 20 g of propargyl chloride are then added. Under constant stirring, the reaction is completed within one hour at the same temperature.
Es wird, wie im Beispiel 1 angegeben, aufgearbeitet, wobei 25 g = 49% der Theorie des neuen Esters der oben angegebenen Formel erhalten werden. Der Ester siedet bei 0,01 mm bei 550C. Blattläuse und Spinnmilben werden von 0,l%igen Lösungen 100%ig abgetötet.It is worked up as indicated in Example 1, 25 g = 49% of the theory of the new ester of the formula given above being obtained. The ester boils at 0.01 mm at 55 ° C. Aphids and spider mites are 100% killed by 0.1% solutions.
909 607/413909 607/413
Claims (1)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL103634D NL103634C (en) | 1957-09-24 | ||
| BE571029D BE571029A (en) | 1957-09-24 | ||
| DEF24013A DE1063148B (en) | 1957-09-24 | 1957-09-24 | Process for the preparation of O, O-dialkyl-S-propargyl-thio- or -dithiophosphoric acid esters |
| CH6349358A CH374649A (en) | 1957-09-24 | 1958-09-01 | Process for the preparation of thiophosphoric acid esters |
| GB2848658A GB860944A (en) | 1957-09-24 | 1958-09-04 | Thiophosphoric acid esters |
| FR1203242D FR1203242A (en) | 1957-09-24 | 1958-09-08 | Process for preparing thiophosphoric esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF24013A DE1063148B (en) | 1957-09-24 | 1957-09-24 | Process for the preparation of O, O-dialkyl-S-propargyl-thio- or -dithiophosphoric acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1063148B true DE1063148B (en) | 1959-08-13 |
Family
ID=7091072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF24013A Pending DE1063148B (en) | 1957-09-24 | 1957-09-24 | Process for the preparation of O, O-dialkyl-S-propargyl-thio- or -dithiophosphoric acid esters |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE571029A (en) |
| CH (1) | CH374649A (en) |
| DE (1) | DE1063148B (en) |
| FR (1) | FR1203242A (en) |
| GB (1) | GB860944A (en) |
| NL (1) | NL103634C (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3019159A (en) * | 1960-05-11 | 1962-01-30 | American Cyanamid Co | Novel phosphorodithioates and methods for preparing the same |
| DE1173723B (en) * | 1960-09-21 | 1964-07-09 | Basf Ag | Preparations for the control of insects |
| DE1175938B (en) * | 1959-10-07 | 1964-08-13 | Montedison Spa | Insecticidal and acaricidal agents |
| DE1221627B (en) | 1960-11-08 | 1966-07-28 | Monsanto Co | Process for the preparation of carbamoylmethylthiophosphoric acid esters |
| CN112010894A (en) * | 2020-08-17 | 2020-12-01 | 湖州师范学院 | Sulfur phosphate compound, nonaqueous lithium ion battery electrolyte containing sulfur phosphate compound and lithium ion battery |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2727479A1 (en) * | 1977-06-18 | 1979-01-04 | Bayer Ag | INSECTICIDES AND ACARICIDES |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2693483A (en) * | 1952-03-06 | 1954-11-02 | Dow Chemical Co | Propynyl phosphate compounds |
-
0
- BE BE571029D patent/BE571029A/xx unknown
- NL NL103634D patent/NL103634C/xx active
-
1957
- 1957-09-24 DE DEF24013A patent/DE1063148B/en active Pending
-
1958
- 1958-09-01 CH CH6349358A patent/CH374649A/en unknown
- 1958-09-04 GB GB2848658A patent/GB860944A/en not_active Expired
- 1958-09-08 FR FR1203242D patent/FR1203242A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2693483A (en) * | 1952-03-06 | 1954-11-02 | Dow Chemical Co | Propynyl phosphate compounds |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1175938B (en) * | 1959-10-07 | 1964-08-13 | Montedison Spa | Insecticidal and acaricidal agents |
| US3019159A (en) * | 1960-05-11 | 1962-01-30 | American Cyanamid Co | Novel phosphorodithioates and methods for preparing the same |
| DE1173723B (en) * | 1960-09-21 | 1964-07-09 | Basf Ag | Preparations for the control of insects |
| DE1221627B (en) | 1960-11-08 | 1966-07-28 | Monsanto Co | Process for the preparation of carbamoylmethylthiophosphoric acid esters |
| CN112010894A (en) * | 2020-08-17 | 2020-12-01 | 湖州师范学院 | Sulfur phosphate compound, nonaqueous lithium ion battery electrolyte containing sulfur phosphate compound and lithium ion battery |
| CN112010894B (en) * | 2020-08-17 | 2023-08-11 | 湖州师范学院 | A kind of phosphoric acid ester compound, non-aqueous lithium-ion battery electrolyte containing it and lithium-ion battery |
Also Published As
| Publication number | Publication date |
|---|---|
| CH374649A (en) | 1964-01-31 |
| NL103634C (en) | |
| GB860944A (en) | 1961-02-15 |
| BE571029A (en) | |
| FR1203242A (en) | 1960-01-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1063148B (en) | Process for the preparation of O, O-dialkyl-S-propargyl-thio- or -dithiophosphoric acid esters | |
| DE1062237B (en) | Process for the preparation of O, O-dialkylthiolphosphoric acid and -thiolthionophosphoric acid-S-gamma-cyanallyl esters | |
| DE1518692C3 (en) | Pesticides containing N- <2-ethyl-4-bromophenyl) -N ', N'-dimethylformamidine | |
| DE1071696B (en) | Process for the preparation of thiophosphoric acid esters | |
| DE1139492B (en) | Process for the production of dithiolphosphonic acid esters | |
| DE2034475C3 (en) | O-AlkyKAJkenyl, AJkinyD-S-alkyl (alkenyl-alkynyl) -N-monoalkyl- (alkenyl, alkynyl) -thionothiolphosphoric acid ester amides, processes for their preparation and their use as nematocides, insecticides and acaricides | |
| DE2037508C3 (en) | 19.01.70 Switzerland 674-70 Pyrimidylphosphoric acid ester amides, process for their preparation and agents containing them | |
| DE2118495C3 (en) | Insecticidal agent | |
| DE1083811B (en) | Process for the preparation of benzylthiomethyl ether thiophosphorus compounds | |
| DE1153747B (en) | Process for the production of phosphorus, phosphonic, phosphine or thiophosphorus, phosphonic and phosphinic acid esters | |
| DE1074034B (en) | Process for the preparation of thiophosphoric acid esters | |
| DE2014794C (en) | 0- (Thiocarbamoyl-pyridyl) -thionophosphoric acid esters and pesticides containing them | |
| DE1078117B (en) | Process for the preparation of thiophosphoric acid esters | |
| DE1793188C3 (en) | O-alkyl-0-phenyl-thiolphosphoric acid ester, process for their preparation and compositions containing them | |
| DE1642260C3 (en) | Thiophosphoric acid esters, process for their preparation and pesticides containing them | |
| DE1221627B (en) | Process for the preparation of carbamoylmethylthiophosphoric acid esters | |
| DE1204667C2 (en) | Process for the preparation of asymmetrical Thionothiolphorsphorsaeureestern | |
| DE1015794B (en) | Process for the preparation of chloromethylated O, O-dialkylthiophosphoric acid esters | |
| DE1178416B (en) | Process for the preparation of bis-dithiocarbamic acid ester derivatives | |
| AT230394B (en) | Process for the preparation of new organophosphorus compounds | |
| US3160554A (en) | Protecting plants from insects with 2-dimethyl-aminophenyl-nu-methyl-carbamate | |
| DE1063155B (en) | Process for the preparation of thiophosphoric acid esters | |
| DE2162238A1 (en) | Pyridine derivs - as herbicides, parasiticides etc | |
| DE1542715C (en) | Pesticides | |
| DE1071701B (en) | Process for the production of new dithiophosphonic acid esters |