GB705807A - O,o-di(4-chlorophenyl) n-alkylamidothiophosphates - Google Patents
O,o-di(4-chlorophenyl) n-alkylamidothiophosphatesInfo
- Publication number
- GB705807A GB705807A GB1601952A GB1601952A GB705807A GB 705807 A GB705807 A GB 705807A GB 1601952 A GB1601952 A GB 1601952A GB 1601952 A GB1601952 A GB 1601952A GB 705807 A GB705807 A GB 705807A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- alkyl radical
- compounds
- nr1r11
- reacting
- 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
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000000417 fungicide Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000002917 insecticide Substances 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- GRUHOZGDHNDMQM-UHFFFAOYSA-N N-[(4-chlorophenoxy)-hydroxyphosphinothioyl]methanamine Chemical compound CNP(O)(=S)OC1=CC=C(Cl)C=C1 GRUHOZGDHNDMQM-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- -1 alkali metal 4-chlorophenolate Chemical class 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- JLYVRXJEQTZZBE-UHFFFAOYSA-N ctk1c6083 Chemical compound NP(N)(N)=S JLYVRXJEQTZZBE-UHFFFAOYSA-N 0.000 abstract 1
- 125000005265 dialkylamine group Chemical group 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000000314 lubricant Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007921 spray Substances 0.000 abstract 1
- 238000009736 wetting Methods 0.000 abstract 1
- 239000000080 wetting agent Substances 0.000 abstract 1
- 235000011845 white flour Nutrition 0.000 abstract 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
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/242—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of hydroxyaryl compounds
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)
Abstract
The invention comprises compounds of the formula <FORM:0705807/IV (b)/1> wherein R1 represents an alkyl radical and R11 represents hydrogen or an alkyl radical. They may be prepared by reacting an alkali metal 4-chlorophenolate with an N-alkyl dichlorothiophosphoramide of the formula <FORM:0705807/IV (b)/2> preferably in an inert solvent, e.g. benzene or methyl or ethyl alcohol. The product may be extracted from the crude reaction mixture with, e.g. benzene, ether or methylene dichloride. The N-alkyl dichlorothiophosphoramides are obtained by reacting a salt of a mono- or dialkyl-amine with excess (e.g. 2 to 4 molecular proportions) of thiosphosphoryl chloride (PSCl3). In an example (1) O, O-di (4-chlorophenyl) N-methylamido-thiophosphate is prepared by reacting 4-chlorophenol and potassium hydroxide in methyl alcohol with N-methyl dichlorothiophosphoramide. In a similar manner there are prepared from the appropriate thiophosphoramide and 4-chlorophenol compounds represented by the above formula when -NR1R11 represents (2) N-ethylamido; (3) N-isopropylamido; (4) N, N-dimethyl-amido; (5) N, N-diethylamido. Also mentioned are such compounds when -NR1R11 represents an N, N-di-sec-butyl amido, N-dodecylamido, N-n-butyl-N-n-hexylamido, or an N-n-octyl radical. The products are of use in insecticides and fungicides (see Group VI), plastic compositions, and extreme pressure lubricants.ALSO:Amido - thiophosphates having the formula <FORM:0705807/VI/1> wherein R1 represents an alkyl radical and R11 represents hydrogen or an alkyl radical are used in insecticides and fungicides. They may be employed in aqueous spray compositions with wetting and emulsifying agents or as mixtures with white flour. Specifically mentioned are compounds represented by the above formula when NR1R11 represents a methylamido, ethylamido, isopropylamido, dimethylamido, diethylamido, di-sec-butylamido, dodecylamido, p N-n-butyl-N-n-hexylamido or an n-octylamido group. The preparation of the first five of these compounds is described (see Group IV(b)).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1601952A GB705807A (en) | 1952-06-25 | 1952-06-25 | O,o-di(4-chlorophenyl) n-alkylamidothiophosphates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1601952A GB705807A (en) | 1952-06-25 | 1952-06-25 | O,o-di(4-chlorophenyl) n-alkylamidothiophosphates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB705807A true GB705807A (en) | 1954-03-17 |
Family
ID=10069695
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1601952A Expired GB705807A (en) | 1952-06-25 | 1952-06-25 | O,o-di(4-chlorophenyl) n-alkylamidothiophosphates |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB705807A (en) |
-
1952
- 1952-06-25 GB GB1601952A patent/GB705807A/en not_active Expired
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