GB834117A - Thiophosphoric acid esters and process for their production - Google Patents
Thiophosphoric acid esters and process for their productionInfo
- Publication number
- GB834117A GB834117A GB3807357A GB3807357A GB834117A GB 834117 A GB834117 A GB 834117A GB 3807357 A GB3807357 A GB 3807357A GB 3807357 A GB3807357 A GB 3807357A GB 834117 A GB834117 A GB 834117A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphur
- compound
- oxygen
- compounds
- group
- 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 abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 12
- 239000005864 Sulphur Substances 0.000 abstract 11
- 150000001875 compounds Chemical class 0.000 abstract 10
- -1 C1-C4 alkyl radical Chemical group 0.000 abstract 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 6
- 229910052760 oxygen Inorganic materials 0.000 abstract 6
- 239000001301 oxygen Substances 0.000 abstract 6
- 125000001174 sulfone group Chemical group 0.000 abstract 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 abstract 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- 239000004480 active ingredient Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000005840 aryl radicals Chemical class 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000003995 emulsifying agent Substances 0.000 abstract 2
- 239000002917 insecticide Substances 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 150000004763 sulfides Chemical class 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003929 acidic solution Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 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
- 239000011230 binding agent Substances 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- 238000007865 diluting Methods 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 239000003337 fertilizer Substances 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 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
- 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
- 239000012286 potassium permanganate Substances 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 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
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
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)
Abstract
The invention comprises thiophosphoric acid esters of the formula <FORM:0834117/IV (b)/1> wherein R is a C1-C4 alkyl radical, R1 an R2 are identical or different alkyl or aryl radicals, either of which may be substituted, X and Y are oxygen or sulphur, at least one of them being sulphur and each A is a sulphoxide (S(O) group) or sulphone (SO2) group. Compounds in which each A is a sulphoxide group may be obtained by reacting the corresponding sulphide compound in which each A is a sulphur atom with hydrogen peroxide, preferably of 30% strength, whereas compounds in which each A is a sulphone group may be obtained by oxidizing the said corresponding sulphide compound with potassium permanganate in acidic solution, e.g. in an aqueous emulsion containing dilute sulphuric acid. The reaction with hydrogen peroxide is generally carried out at room temperature or lower, e.g. down to about 0 DEG C., and may be carried out in an inert solvent, e.g. an aliphatic carboxylic acid containing 1 to 4 carbon atoms, especially glacial acetic acid. Examples are given for the production of compounds in which X is oxygen, Y is sulphur, R1 and R2 are each ethyl and A is S(O) and SO2 respectively and in which X and Y are sulphur, R1 and R2 are ethyl and A is S(O). Other products specified are those in which X is sulphur, Y is oxygen, R1 and R2 are each ethyl and A is SO or SO2, and the compounds <FORM:0834117/IV (b)/2> and the corresponding sulphone compound, <FORM:0834117/IV (b)/3> and the corresponding sulphone compound, and <FORM:0834117/IV (b)/4> and the corresponding sulphone compound. The products are useful as insecticides (see Group VI). The sulphides (i.e. compounds in which A is sulphur, X is sulphur and Y is oxygen) used as starting materials may be obtained by reacting a compound of the formula (R1SCH2)(R2SCH2) CHOH with a compound of the formula (RO)2P(S)Hal optionally in the presence of an acid binding agent and the sulphides in which X is oxygen or sulphur and Y is sulphur may be obtained by reacting a compound of the formula (R1SCH2)(R2SCH2)CH.Hal with an ammonium or alkali metal salt of the appropriate thiol- or thionothiol-phosphoric acid.ALSO:An insecticidal composition contains as active ingredient one or more thiophosphoric acid esters of the formula <FORM:0834117/VI/1> wherein R is an alkyl radical containing up to 4 carbon atoms, R1 and R2 are identical or different alkyl or aryl radicals which radicals may be substituted or unsubstituted, each A is a sulphoxide or sulphone group and X and Y are oxygen or sulphur, at least one of them being sulphur (see Group IV (b)). The active ingredient may be diluted or extended with solid or liquid carriers or diluents, e.g. talc, chalk, bentonite, clay, water (if necessary with the addition of emulsifiers), alcohols, e.g. methanol or ethanol, ketones, e.g. acetone or methyl ethyl ketone, and liquid hydrocarbons. The compounds may be used in combination with known insecticides and/or fertilizers. A suitable composition is obtained by mixing the compound (C2H5O)2P(O)SCH(CH2S(O) C2H5)2 with acetone and a commercial emulsifier, e.g. benzyl hydroxy diphenyl polyglycol ether, and then diluting with water.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF21896A DE1063153B (en) | 1956-12-10 | 1956-12-10 | Process for the preparation of esters of thiophosphoric acid containing sulfide, sulfoxide or sulfone groups |
Publications (1)
Publication Number | Publication Date |
---|---|
GB834117A true GB834117A (en) | 1960-05-04 |
Family
ID=7090245
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3807357A Expired GB834117A (en) | 1956-12-10 | 1957-12-06 | Thiophosphoric acid esters and process for their production |
Country Status (4)
Country | Link |
---|---|
CH (1) | CH367823A (en) |
DE (1) | DE1063153B (en) |
FR (1) | FR1190063A (en) |
GB (1) | GB834117A (en) |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE836349C (en) * | 1950-05-10 | 1952-04-10 | Bayer Ag | Process for the preparation of neutral esters of thiophosphoric acid |
DE830509C (en) * | 1950-05-24 | 1952-02-04 | Bayer Ag | Process for the preparation of neutral esters of thiophosphoric acid |
CH311106A (en) * | 1952-08-22 | 1955-11-30 | Ciba Geigy | Pest control methods. |
NL191318A (en) * | 1953-10-07 | |||
DE947368C (en) * | 1954-11-06 | 1956-08-16 | Bayer Ag | Process for the preparation of esters of phosphoric and thiophosphoric acids containing sulfoxide groups |
DE949229C (en) * | 1955-02-03 | 1956-11-22 | Bayer Ag | Process for the preparation of esters of phosphoric and thiophosphoric acid containing sulfoxide groups |
-
1956
- 1956-12-10 DE DEF21896A patent/DE1063153B/en active Pending
-
1957
- 1957-11-11 CH CH5252757A patent/CH367823A/en unknown
- 1957-11-15 FR FR1190063D patent/FR1190063A/en not_active Expired
- 1957-12-06 GB GB3807357A patent/GB834117A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
FR1190063A (en) | 1959-10-09 |
DE1063153B (en) | 1959-08-13 |
CH367823A (en) | 1963-03-15 |
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