DE1080109B - Verfahren zur Herstellung von Aminophosphorsaeure-O-alkyl-thiolestern - Google Patents
Verfahren zur Herstellung von Aminophosphorsaeure-O-alkyl-thiolesternInfo
- Publication number
- DE1080109B DE1080109B DEF26444A DEF0026444A DE1080109B DE 1080109 B DE1080109 B DE 1080109B DE F26444 A DEF26444 A DE F26444A DE F0026444 A DEF0026444 A DE F0026444A DE 1080109 B DE1080109 B DE 1080109B
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- acid
- preparation
- water
- thiolesters
- 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 9
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 2
- ZOYYLYJJZVGFJC-UHFFFAOYSA-N o-dihydroxyphosphinothioylhydroxylamine Chemical compound NOP(O)(O)=S ZOYYLYJJZVGFJC-UHFFFAOYSA-N 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- JZTPOMIFAFKKSK-UHFFFAOYSA-N O-phosphonohydroxylamine Chemical compound NOP(O)(O)=O JZTPOMIFAFKKSK-UHFFFAOYSA-N 0.000 claims 1
- 241001124076 Aphididae Species 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 241001454295 Tetranychidae Species 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000009885 systemic effect Effects 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 239000000839 emulsion Substances 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- ZZPRJXDNBLEXHH-UHFFFAOYSA-N N-dihydroxyphosphinothioyloxy-N-methylmethanamine Chemical compound CN(C)OP(O)(O)=S ZZPRJXDNBLEXHH-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000003151 ovacidal effect Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 241000861718 Chloris <Aves> Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- JKPAIQYTAZUMKI-UHFFFAOYSA-N N[P] Chemical compound N[P] JKPAIQYTAZUMKI-UHFFFAOYSA-N 0.000 description 1
- 241000488583 Panonychus ulmi Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 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
- 241001454294 Tetranychus Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- -1 alkyl mercaptoalkyl mercaptans Chemical class 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- RPXCCPFIMAPSKP-UHFFFAOYSA-N dimethylamino dihydrogen phosphate Chemical compound CN(C)OP(O)(O)=O RPXCCPFIMAPSKP-UHFFFAOYSA-N 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000006887 os medium Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000007970 thio 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
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL242465D NL242465A (en, 2012) | 1958-08-20 | ||
| BE581822D BE581822A (en, 2012) | 1958-08-20 | ||
| BE581812D BE581812A (en, 2012) | 1958-08-20 | ||
| DEF26444A DE1080109B (de) | 1958-08-20 | 1958-08-20 | Verfahren zur Herstellung von Aminophosphorsaeure-O-alkyl-thiolestern |
| CH7618459A CH401965A (de) | 1958-08-20 | 1959-07-24 | Verfahren zur Herstellung von Aminophosphorsäureestern |
| GB2644159A GB885491A (en) | 1958-08-20 | 1959-07-31 | Dialkyl-amino-thiolphosphoric acid esters |
| US830740A US2971020A (en) | 1958-08-20 | 1959-07-31 | Amino-thiophosphoric acid esters and a process for their production |
| DK293059A DK99014C (da) | 1958-08-20 | 1959-08-15 | Fremgangsmåde til fremstilling af aminophosphorsyreestere. |
| FR803060A FR1233343A (fr) | 1958-08-20 | 1959-08-18 | Nouveaux esters aminophosphoriques et procédé pour leur préparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF26444A DE1080109B (de) | 1958-08-20 | 1958-08-20 | Verfahren zur Herstellung von Aminophosphorsaeure-O-alkyl-thiolestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1080109B true DE1080109B (de) | 1960-04-21 |
Family
ID=7092027
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF26444A Pending DE1080109B (de) | 1958-08-20 | 1958-08-20 | Verfahren zur Herstellung von Aminophosphorsaeure-O-alkyl-thiolestern |
Country Status (7)
| Country | Link |
|---|---|
| BE (2) | BE581822A (en, 2012) |
| CH (1) | CH401965A (en, 2012) |
| DE (1) | DE1080109B (en, 2012) |
| DK (1) | DK99014C (en, 2012) |
| FR (1) | FR1233343A (en, 2012) |
| GB (1) | GB885491A (en, 2012) |
| NL (1) | NL242465A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3309266A (en) * | 1965-07-01 | 1967-03-14 | Chevron Res | Insecticidal compositions containing oalkyl-s-alkyl phosphoroamidothioates and methods for killing insects therewith |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1032247B (de) | 1954-12-04 | 1958-06-19 | Bayer Ag | Verfahren zur Herstellung von organischen Phosphorverbindungen |
-
0
- BE BE581812D patent/BE581812A/xx unknown
- BE BE581822D patent/BE581822A/xx unknown
- NL NL242465D patent/NL242465A/xx unknown
-
1958
- 1958-08-20 DE DEF26444A patent/DE1080109B/de active Pending
-
1959
- 1959-07-24 CH CH7618459A patent/CH401965A/de unknown
- 1959-07-31 GB GB2644159A patent/GB885491A/en not_active Expired
- 1959-08-15 DK DK293059A patent/DK99014C/da active
- 1959-08-18 FR FR803060A patent/FR1233343A/fr not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1032247B (de) | 1954-12-04 | 1958-06-19 | Bayer Ag | Verfahren zur Herstellung von organischen Phosphorverbindungen |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3309266A (en) * | 1965-07-01 | 1967-03-14 | Chevron Res | Insecticidal compositions containing oalkyl-s-alkyl phosphoroamidothioates and methods for killing insects therewith |
Also Published As
| Publication number | Publication date |
|---|---|
| NL242465A (en, 2012) | |
| DK99014C (da) | 1964-06-15 |
| CH401965A (de) | 1965-11-15 |
| FR1233343A (fr) | 1960-10-12 |
| BE581812A (en, 2012) | |
| GB885491A (en) | 1961-12-28 |
| BE581822A (en, 2012) |
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