GB808259A - Thiophosphoric acid esters - Google Patents
Thiophosphoric acid estersInfo
- Publication number
- GB808259A GB808259A GB1297457A GB1297457A GB808259A GB 808259 A GB808259 A GB 808259A GB 1297457 A GB1297457 A GB 1297457A GB 1297457 A GB1297457 A GB 1297457A GB 808259 A GB808259 A GB 808259A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- radical
- sulphur
- methyl
- propyl
- 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
- 150000003580 thiophosphoric acid esters Chemical class 0.000 title 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 11
- -1 alkyl radical Chemical group 0.000 abstract 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 5
- 239000005864 Sulphur Chemical group 0.000 abstract 5
- 229910052760 oxygen Inorganic materials 0.000 abstract 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 4
- 239000001301 oxygen Substances 0.000 abstract 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000005840 aryl radicals Chemical class 0.000 abstract 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract 2
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical class OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 abstract 2
- 239000000443 aerosol Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000000440 bentonite Substances 0.000 abstract 1
- 229910000278 bentonite Inorganic materials 0.000 abstract 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- 238000010410 dusting Methods 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 229920000151 polyglycol Polymers 0.000 abstract 1
- 239000010695 polyglycol Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 238000005507 spraying Methods 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
Classifications
-
- 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
-
- 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
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises esters of formula <FORM:0808259/IV (b)/1> where R is an alkyl radical, an aryl radical which may be substituted, e.g. by halogen, nitro or alkoxy, a polycyclic radical or a heterocyclic radical, R1 is a C1-4 alkyl radical, and X is oxygen or sulphur. They may be prepared by reacting salts of O,O-dialkyl thiol- or thionothiol-phosphoric acids with N-acyl-chloroacetamides, generally in an inert solvent such as water, alcohols and ketones, and preferably between about room temperature and 60-80 DEG C. Specified acyl radicals are those derived from acetic, propionic, butyric, isobutyric, valeric, phenylacetic, benzoic, o-, m-and p-chlorobenzoic, the nitrobenzoic, toluic, naphthoic, pyridinic and quinolinic acids. Examples describe the preparation by the above method of compounds in which (1) R is methyl, X is sulphur and R1 is ethyl, propyl or butyl; (2) R1 is methyl, X is sulphur and R is methyl, ethyl or propyl; (3) X is oxygen, R is methyl when R1 is methyl, ethyl or propyl, ethyl when R1 is ethyl, or propyl when R1 is ethyl; (4) R is phenyl, X is sulphur and R1 is ethyl; (5) R is phenyl, X is oxygen and R1 is ethyl; (6) R is p-chlorophenyl, X is sulphur and R1 is ethyl; (7) R is p-chlorophenyl, X is oxygen and R1 is ethyl.ALSO:Insecticidal compositions comprise thiophosphoric esters of formula <FORM:0808259/VI/1> where R is an alkyl or aryl radical which may be substituted, e.g. by halogen, nitro or alkoxy, a polycyclic radical or a heterocyclic radical, R1 is a C1-4 alkyl radical and X is O or S. Specified R-CO- radicals are those derived from acetic, propionic, butyric, isobutyric, valeric, phenylacetic, benzoic, chlorobenzoic, nitrobenzoic, toluic, naphthoic, pyridinic and quinolinic acids. They may be applied in concentrations from 0.001 to 1 per cent, diluted with solid or liquid carriers such as talc, chalk, bentonite, clay, water and organic solvents. Aerosols may be used or they may be applied by dusting or spraying. In an example the compound in which R is CH3, R1 is C2H5 and X is S is dissolved in acetone and diluted to 0.01 per cent with water in the presence of an emulsifier such as a polyglycol ether of benzyl-hydroxydiphenyl.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF20108A DE1022579B (en) | 1956-04-21 | 1956-04-21 | Process for the preparation of insecticidally active thiophosphoric acid esters or dithiophosphoric acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB808259A true GB808259A (en) | 1959-01-28 |
Family
ID=7089559
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1297457A Expired GB808259A (en) | 1956-04-21 | 1957-04-23 | Thiophosphoric acid esters |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1022579B (en) |
| GB (1) | GB808259A (en) |
| NL (1) | NL107328C (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU36138A1 (en) * | 1957-06-03 | |||
| NL133769C (en) * | 1960-02-24 | |||
| DE1183082B (en) * | 1963-07-17 | 1964-12-10 | Bayer Ag | Process for the production of thiol or thionothiolphosphonic acid esters |
-
1956
- 1956-04-21 DE DEF20108A patent/DE1022579B/en active Pending
-
1957
- 1957-04-16 NL NL216389A patent/NL107328C/xx active
- 1957-04-23 GB GB1297457A patent/GB808259A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1022579B (en) | 1958-01-16 |
| NL107328C (en) | 1964-01-17 |
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