DE1138047B - Verfahren zur Herstellung von Dithiophosphonsaeureestern - Google Patents
Verfahren zur Herstellung von DithiophosphonsaeureesternInfo
- Publication number
- DE1138047B DE1138047B DEF28059A DEF0028059A DE1138047B DE 1138047 B DE1138047 B DE 1138047B DE F28059 A DEF28059 A DE F28059A DE F0028059 A DEF0028059 A DE F0028059A DE 1138047 B DE1138047 B DE 1138047B
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- ester
- general formula
- lower alkyl
- 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 10
- FLQUDUCNBDGCRI-UHFFFAOYSA-N hydroxy-sulfanyl-sulfidophosphanium Chemical class SP(S)=O FLQUDUCNBDGCRI-UHFFFAOYSA-N 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 30
- 150000002148 esters Chemical class 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 9
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 229910052700 potassium Inorganic materials 0.000 claims description 8
- 239000011591 potassium Substances 0.000 claims description 8
- -1 cyano, phenyl Chemical group 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 241000700159 Rattus Species 0.000 description 8
- 230000001988 toxicity Effects 0.000 description 7
- 231100000419 toxicity Toxicity 0.000 description 7
- 241000255925 Diptera Species 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 230000000749 insecticidal effect Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 241001674044 Blattodea Species 0.000 description 2
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- HFVYUQVSWQURMK-UHFFFAOYSA-N (3-ethyl-1-sulfanylidenethiophen-2-yl)phosphonic acid Chemical compound C(C)C1=C(S(C=C1)=S)P(O)(=O)O HFVYUQVSWQURMK-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004849 alkoxymethyl group Chemical group 0.000 description 1
- 125000002521 alkyl halide group Chemical group 0.000 description 1
- 150000001356 alkyl thiols Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- IFQMTQSXPWHEEG-UHFFFAOYSA-N thiophen-2-ylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CS1 IFQMTQSXPWHEEG-UHFFFAOYSA-N 0.000 description 1
- 150000005691 triesters 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
-
- 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
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
-
- 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
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
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)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE589121D BE589121A (en, 2012) | 1959-03-28 | ||
| NL249895D NL249895A (en, 2012) | 1959-03-28 | ||
| NL125459D NL125459C (en, 2012) | 1959-03-28 | ||
| NL137850D NL137850C (en, 2012) | 1959-03-28 | ||
| DEF28059A DE1138047B (de) | 1959-03-28 | 1959-03-28 | Verfahren zur Herstellung von Dithiophosphonsaeureestern |
| CH320860A CH393322A (de) | 1959-03-28 | 1960-03-22 | Verfahren zur Herstellung von Derivaten der Dithiophosphonsäure |
| US17500A US3507953A (en) | 1959-03-28 | 1960-03-25 | Pesticidal dithiophosphonic acid esters |
| GB10945/60A GB898313A (en) | 1959-03-28 | 1960-03-28 | Derivatives of thionothiol phosphonic acid |
| FR822654A FR1261255A (fr) | 1959-03-28 | 1960-03-28 | Fabrication de dérivés de l'acide dithiophosphonique |
| NL6807950A NL6807950A (en, 2012) | 1959-03-28 | 1968-06-06 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF28059A DE1138047B (de) | 1959-03-28 | 1959-03-28 | Verfahren zur Herstellung von Dithiophosphonsaeureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1138047B true DE1138047B (de) | 1962-10-18 |
Family
ID=7092724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF28059A Pending DE1138047B (de) | 1959-03-28 | 1959-03-28 | Verfahren zur Herstellung von Dithiophosphonsaeureestern |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3507953A (en, 2012) |
| BE (1) | BE589121A (en, 2012) |
| CH (1) | CH393322A (en, 2012) |
| DE (1) | DE1138047B (en, 2012) |
| GB (1) | GB898313A (en, 2012) |
| NL (4) | NL6807950A (en, 2012) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1014105B (de) * | 1955-09-07 | 1957-08-22 | Bayer Ag | Verfahren zur Herstellung von O,O-Dialkyl-thiophosphorsaeuretriestern |
| DE1032247B (de) * | 1954-12-04 | 1958-06-19 | Bayer Ag | Verfahren zur Herstellung von organischen Phosphorverbindungen |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA494562A (en) * | 1948-02-04 | 1953-07-21 | American Cyanamid Company | Carbamylalkyl phosphates and method of preparation |
| US2494284A (en) * | 1949-01-12 | 1950-01-10 | American Cyanamid Co | Cyanoalkyl phosphates and method of preparation |
| US2611728A (en) * | 1949-11-01 | 1952-09-23 | Standard Oil Dev Co | Insecticidal compositions containing substituted aliphatic esters of diethyl dithiophosphoric acid |
| NL101816C (en, 2012) * | 1955-05-03 | |||
| US2884353A (en) * | 1955-08-30 | 1959-04-28 | Hercules Powder Co Ltd | Dithiophosphate insecticides |
| US2884354A (en) * | 1955-08-30 | 1959-04-28 | Hercules Powder Co Ltd | Dithiophosphate insecticides |
| US2908605A (en) * | 1955-11-03 | 1959-10-13 | Ciba Ltd | New organic phosphorus compounds and process for their manufacture |
| US2967884A (en) * | 1958-04-01 | 1961-01-10 | Union Carbide Corp | Preparation of acrylic acid esters |
| US3013047A (en) * | 1959-03-28 | 1961-12-12 | Bayer Ag | Phosphorus-containing derivatives of benzylmercaptan and process for their production |
| US3100735A (en) * | 1961-11-07 | 1963-08-13 | Stauffer Chemical Co | Bisorganophosphorus esters and their preparation |
-
0
- NL NL137850D patent/NL137850C/xx active
- NL NL125459D patent/NL125459C/xx active
- NL NL249895D patent/NL249895A/xx unknown
- BE BE589121D patent/BE589121A/xx unknown
-
1959
- 1959-03-28 DE DEF28059A patent/DE1138047B/de active Pending
-
1960
- 1960-03-22 CH CH320860A patent/CH393322A/de unknown
- 1960-03-25 US US17500A patent/US3507953A/en not_active Expired - Lifetime
- 1960-03-28 GB GB10945/60A patent/GB898313A/en not_active Expired
-
1968
- 1968-06-06 NL NL6807950A patent/NL6807950A/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1032247B (de) * | 1954-12-04 | 1958-06-19 | Bayer Ag | Verfahren zur Herstellung von organischen Phosphorverbindungen |
| DE1014105B (de) * | 1955-09-07 | 1957-08-22 | Bayer Ag | Verfahren zur Herstellung von O,O-Dialkyl-thiophosphorsaeuretriestern |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6807950A (en, 2012) | 1968-08-26 |
| GB898313A (en) | 1962-06-06 |
| NL125459C (en, 2012) | |
| NL249895A (en, 2012) | |
| US3507953A (en) | 1970-04-21 |
| BE589121A (en, 2012) | |
| CH393322A (de) | 1965-06-15 |
| NL137850C (en, 2012) |
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