GB839924A - New compounds of o, o-dialkylphosphoric or -thiophosphoric acids and a process for their production - Google Patents
New compounds of o, o-dialkylphosphoric or -thiophosphoric acids and a process for their productionInfo
- Publication number
- GB839924A GB839924A GB861058A GB861058A GB839924A GB 839924 A GB839924 A GB 839924A GB 861058 A GB861058 A GB 861058A GB 861058 A GB861058 A GB 861058A GB 839924 A GB839924 A GB 839924A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- different
- same
- acid
- formula
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- 150000002431 hydrogen Chemical group 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 230000000749 insecticidal effect Effects 0.000 abstract 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- 241001124076 Aphididae Species 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 241000257226 Muscidae Species 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 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
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/095—Compounds containing the structure P(=O)-O-acyl, P(=O)-O-heteroatom, P(=O)-O-CN
- C07F9/096—Compounds containing the structure P(=O)-O-C(=X)- (X = O, S, Se)
-
- 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
- C07F9/1654—Compounds containing the structure P(=X)n-X-acyl, P(=X)n-X-heteroatom, P(=X)n-X-CN (X = O, S, Se; n = 0, 1)
- C07F9/1656—Compounds containing the structure P(=X)n-X-C(=X)- (X = O, S, Se; n = 0, 1)
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (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)
Abstract
The invention comprises compounds of the general formula <FORM:0839924/IV (b)/1> in which R1 and R2 are alkyl radicals, R3 is hydrogen, a dialkoxyphosphoric acid acyl radical or a dialkoxythiophosphoric acid acyl radical, X is an oxygen or sulphur atom, n represents a number from 0 to 6 and each Y which may be the same or different is selected from hydrogen, alkyl, aryl, cycloalkyl or halogen and when n is 2 or more the groups (CY2) may be the same or different. They may be obtained by reacting a compound of the formula <FORM:0839924/IV (b)/2> in which Hal is a halogen atom with a dicarboxylic acid of the formula <FORM:0839924/IV (b)/3> or a salt thereof, preferably an alkali metal, alkaline earth metal or lead salt. The reaction is preferably carried out in the presence of an organic solvent, e.g. a hydrocarbon, chloro-hydrocarbon, an ether, e.g. tetrahydrofurane or dioxane, a ketone or an alcohol. Suitable reaction temperatures are between -10 DEG and 120 DEG C. and preferably between 20 DEG and 60 DEG C. When the free dicarboxylic acid is used it is preferred to carry out the reaction in the presence of an agent which binds hydrogen halide, e.g. triethylamine, pyridine or an alkali metal carbonate or bicarbonate. A liquid base may wholly or partly replace the solvent. The products have good insecticidal properties (see Group VI).ALSO:An insecticidal composition comprises as active ingredient a compound of the general formula. <FORM:0839924/VI/1> in which R1 and R2 are alkyl radicals, R3 is hydrogen, a dialkoxyphosphoric acid radical or a dialkoxythiophosphoric acid radical, X is oxygen or sulphur, n is a number from 0 to 6 and each Y which may be the same or different, is selected from hydrogen, alkyl, aryl, cycloalkyl or halogen, and when n is 2 or more the groups (CY2) may be the same or different. A table is given to show the insecticidal effect on house flies and plant lice of acetonic solutions or aqueous emulsions of various products of the above formula.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB43979A DE1044073B (en) | 1957-03-20 | 1957-03-20 | Process for the preparation of O, O-dialkylphosphoric acid or thiophosphoric acid compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB839924A true GB839924A (en) | 1960-06-29 |
Family
ID=6967206
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB861058A Expired GB839924A (en) | 1957-03-20 | 1958-03-18 | New compounds of o, o-dialkylphosphoric or -thiophosphoric acids and a process for their production |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH368789A (en) |
| DE (1) | DE1044073B (en) |
| FR (1) | FR1193478A (en) |
| GB (1) | GB839924A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5279751A (en) * | 1990-10-01 | 1994-01-18 | Mobil Oil Corporation | Reaction products of sulfur-containing diacyl halides with phosphorodithioic acid and phenols or thiazoles as multifunctional lubricant additives |
| AU658821B2 (en) * | 1990-03-14 | 1995-05-04 | University Of Toronto Innovations Foundation, The | Acyl phosphate esters and modification of proteins therewith |
-
1957
- 1957-03-20 DE DEB43979A patent/DE1044073B/en active Pending
-
1958
- 1958-03-13 CH CH5700958A patent/CH368789A/en unknown
- 1958-03-18 GB GB861058A patent/GB839924A/en not_active Expired
- 1958-03-20 FR FR1193478D patent/FR1193478A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU658821B2 (en) * | 1990-03-14 | 1995-05-04 | University Of Toronto Innovations Foundation, The | Acyl phosphate esters and modification of proteins therewith |
| US5279751A (en) * | 1990-10-01 | 1994-01-18 | Mobil Oil Corporation | Reaction products of sulfur-containing diacyl halides with phosphorodithioic acid and phenols or thiazoles as multifunctional lubricant additives |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1044073B (en) | 1958-11-20 |
| FR1193478A (en) | 1959-11-03 |
| CH368789A (en) | 1963-04-30 |
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