GB822476A - Thionophosphoric acid esters and a process for their production - Google Patents
Thionophosphoric acid esters and a process for their productionInfo
- Publication number
- GB822476A GB822476A GB3840657A GB3840657A GB822476A GB 822476 A GB822476 A GB 822476A GB 3840657 A GB3840657 A GB 3840657A GB 3840657 A GB3840657 A GB 3840657A GB 822476 A GB822476 A GB 822476A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- butyl
- ethyl
- compound
- 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
- 239000002253 acid Substances 0.000 title abstract 4
- 150000002148 esters Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 4
- 239000007788 liquid Substances 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 229930195733 hydrocarbon Natural products 0.000 abstract 3
- 150000002430 hydrocarbons Chemical class 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
- AFVJGYRAILXFPC-UHFFFAOYSA-N [chlorosulfinyl(methyl)amino]methane Chemical compound CN(C)S(Cl)=O AFVJGYRAILXFPC-UHFFFAOYSA-N 0.000 abstract 2
- 229960000583 acetic acid Drugs 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 2
- 239000012362 glacial acetic acid Substances 0.000 abstract 2
- 239000002917 insecticide Substances 0.000 abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- GXVWJQNUQYSLNR-UHFFFAOYSA-N butoxy(butylsulfanyl)phosphinous acid Chemical class P(SCCCC)(OCCCC)O GXVWJQNUQYSLNR-UHFFFAOYSA-N 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 239000003337 fertilizer Substances 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 1
- 229920000151 polyglycol Polymers 0.000 abstract 1
- 239000010695 polyglycol Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1658—Esters of thiopolyphosphoric acids or anhydrides
-
- 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
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 thionophosphoric ester derivatives of the formula (RO)2P(S).SO.P(S)(OR)2 wherein R is an alkyl radical, preferably containing up to 6 carbon atoms. They may be obtained by reacting a dialkylaminosulphinic acid chloride with a dialkyl-thiophosphite in an inert organic solvent, e.g. a hydrocarbon such as benzene, toluene, or ligroin, or by oxidizing a tetra-alkyl thionophosphoric acid disulphide of the formula (RO)2P(S)S.S.P(S)(OR)2, preferably with hydrogen peroxide in a weakly acid medium. The reaction with hydrogen peroxide is preferably carried out in an inert organic solvent and at a temperature of 40 DEG to 70 DEG C. Glacial acetic acid is a particularly suitable solvent but a liquid hydrocarbon may also be used as solvent if the reaction is carried out in the presence of a small amount of sulphuric acid. Examples are given for the production of compounds of the above formula in which each R is ethyl, methyl, n-propyl, and iso-propyl, respectively, the compound in which each R is ethyl being obtained by oxidation of the corresponding disulphide by means of 37.5% hydrogen peroxide in the presence of glacial acetic acid at 40 DEG C. and the other compounds being obtained by reacting dimethylamino-sulphinic acid chloride with the appropriate dialkyl thiophosphite in the presence of benzene. An example is also given in which the compound in which each R is ethyl is obtained by the latter method and it is stated that compounds in which each R stands for n-butyl, iso-butyl, sec.-butyl and tert.-butyl may also be obtained from the corresponding dibutyl thiophosphites and dimethylaminosulphinic acid chloride. In the example given for the production of the compound in which each R is isopropyl some tetraisopropyl thiono-phosphoric acid disulphide is obtained as a by-product. The sulphoxide products are stated to be useful as insecticides (see Group VI).ALSO:An insecticidal composition comprises a solid or liquid carrier or diluent and one or more thionophosphoric acid esters of the formula <FORM:0822476/VI/1> wherein R is an alkyl radical, preferably containing up to 6 carbon atoms. In an example a compound of the above formula in which each R is ethyl, is dissolved in dimethyl formamide and benzyl hydroxy diphenyl polyglycol ether is added as emulsifier, the resulting mixture being then diluted with water. Other liquid diluents specified are methanol, ethanol, acetone, dimethyl ketone and liquid hydrocarbons. Known insecticides and fertilizers may also be present.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF21904A DE1040542B (en) | 1956-12-11 | 1956-12-11 | Process for the preparation of thionophosphoric acid esters |
| DEF23319A DE1046034B (en) | 1956-12-11 | 1957-06-24 | Process for the preparation of thionophosphoric acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB822476A true GB822476A (en) | 1959-10-28 |
Family
ID=25974004
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3840657A Expired GB822476A (en) | 1956-12-11 | 1957-12-10 | Thionophosphoric acid esters and a process for their production |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE562442A (en) |
| CH (2) | CH374650A (en) |
| DE (2) | DE1040542B (en) |
| FR (1) | FR1190076A (en) |
| GB (1) | GB822476A (en) |
| NL (1) | NL97805C (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1188859B (en) * | 1960-12-10 | 1965-03-11 | Basf Ag | Preparations for the control of insects |
| NL135594C (en) * | 1961-06-06 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE820001C (en) * | 1949-09-07 | 1951-11-08 | Bayer Ag | Process for the preparation of thiopyrophosphoric acid esters |
| US2705694A (en) * | 1952-06-24 | 1955-04-05 | Exxon Research Engineering Co | Insecticidal compositions comprising diethyl thiophosphoric acid disulfide |
-
0
- NL NL97805D patent/NL97805C/xx active
- BE BE562442D patent/BE562442A/xx unknown
-
1956
- 1956-12-11 DE DEF21904A patent/DE1040542B/en active Pending
-
1957
- 1957-06-24 DE DEF23319A patent/DE1046034B/en active Pending
- 1957-11-18 CH CH294563A patent/CH374650A/en unknown
- 1957-11-18 CH CH5277457A patent/CH368157A/en unknown
- 1957-11-19 FR FR1190076D patent/FR1190076A/en not_active Expired
- 1957-12-10 GB GB3840657A patent/GB822476A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE562442A (en) | |
| DE1040542B (en) | 1958-10-09 |
| NL97805C (en) | |
| CH368157A (en) | 1963-03-31 |
| CH374650A (en) | 1964-01-31 |
| FR1190076A (en) | 1959-10-09 |
| DE1046034B (en) | 1958-12-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB834354A (en) | Esters of thiophosphoric acids containing sulphoxide groups | |
| US3086988A (en) | 2-hydroxy-4-(2-hydroxyalkoxy) benzophenones and their lower alkanoic acid esters | |
| GB932011A (en) | Improvements in or relating to dithiophosphonic acid ester derivatives suitable for use as insecticides | |
| GB893234A (en) | Phosphonic acid esters | |
| GB822476A (en) | Thionophosphoric acid esters and a process for their production | |
| GB816286A (en) | Thiophosphoric acid esters and process for their manufacture | |
| KR830007554A (en) | Method for preparing indolinone | |
| GB977071A (en) | Hydroxylamine derivatives and process for making them | |
| GB860944A (en) | Thiophosphoric acid esters | |
| GB874570A (en) | Thiophosphoric acid esters | |
| GB833244A (en) | Thiolphosphoric acid esters and their production | |
| GB841671A (en) | Phosphonic acid esters | |
| GB881977A (en) | Thiophosphonic acid esters | |
| GB921801A (en) | Dithiophosphoric acid esters | |
| GB808879A (en) | Thiophosphoric acid esters | |
| GB815218A (en) | New thiophosphoric acid esters and a process for their production | |
| US3357992A (en) | Process for preparing sultones | |
| GB811268A (en) | Sulphinyl-phosphoric acid esters and a process for their production | |
| GB845373A (en) | Dithiophosphoric acid esters and process for their production | |
| GB834331A (en) | Thiophosphoric acid esters and their production | |
| GB924034A (en) | Thiophosphoric acid esters | |
| GB834117A (en) | Thiophosphoric acid esters and process for their production | |
| GB929216A (en) | Process for the production of thiol-and thionothiol-phosphoric and -phosphinic acid esters | |
| GB754295A (en) | Preparation of ª -chloro-ª -methyl aliphatic acids and acid chlorides | |
| GB793279A (en) | Process for the manufacture of phosphoric and thiophosphoric acid ester derivatives containing sulphoxide groups |