GB860944A - Thiophosphoric acid esters - Google Patents
Thiophosphoric acid estersInfo
- Publication number
- GB860944A GB860944A GB2848658A GB2848658A GB860944A GB 860944 A GB860944 A GB 860944A GB 2848658 A GB2848658 A GB 2848658A GB 2848658 A GB2848658 A GB 2848658A GB 860944 A GB860944 A GB 860944A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphur
- acetone
- oxygen
- thiophosphoric acid
- sch2
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 3
- 239000005864 Sulphur Chemical group 0.000 abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 230000000749 insecticidal effect Effects 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 abstract 1
- 239000005995 Aluminium silicate Substances 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- 101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 abstract 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 235000012211 aluminium silicate Nutrition 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 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
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- -1 chalk Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000007865 diluting Methods 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 abstract 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 229920000151 polyglycol Polymers 0.000 abstract 1
- 239000010695 polyglycol Substances 0.000 abstract 1
- LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 235000012222 talc Nutrition 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
- C07F9/173—Esters of thiophosphoric acids with unsaturated acyclic alcohols
-
- 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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises thiophosphoric acid esters of the formula (RO)2P(X).S.CH2CCH wherein R is a C1-C6 alkyl radical and X is oxygen or sulphur. They may be obtained by reacting propargyl chloride or bromide with a salt of an O,O-dialkyl thio- or dithio-phosphoric acid. The salt used is preferably an alkali metal or ammonium salt and the reaction is generally carried out in an inert organic solvent, e.g. methanol, ethanol, acetone or methyl ethyl ketone, and at between 0 DEG and 100 DEG C., and preferably between 50 DEG and 90 DEG C. Specified products are those in which X is oxygen or sulphur and each R is methyl, ethyl and isopropyl respectively. The products have insecticidal properties (see Group VI).ALSO:An insecticidal composition comprises as active ingredient a thiophosphoric acid ester of the formula (RO)2P(X)SCH2-CCH wherein R is a C1-C6 alkyl radical and X is oxygen or sulphur (see Group IV (b)). Specified carriers or diluents are talcum, chalk, bentonite, alumina, kaolin, water, dimethyl formamide, and acetone. A typical composition is obtained by mixing a solution of the compound (C2H5O)2P(O)SCH2.CCH with acetone, adding benzyl hydroxy diphenyl polyglycol ether as emulsifier and then diluting with water.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF24013A DE1063148B (en) | 1957-09-24 | 1957-09-24 | Process for the preparation of O, O-dialkyl-S-propargyl-thio- or -dithiophosphoric acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB860944A true GB860944A (en) | 1961-02-15 |
Family
ID=7091072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2848658A Expired GB860944A (en) | 1957-09-24 | 1958-09-04 | Thiophosphoric acid esters |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE571029A (en) |
| CH (1) | CH374649A (en) |
| DE (1) | DE1063148B (en) |
| FR (1) | FR1203242A (en) |
| GB (1) | GB860944A (en) |
| NL (1) | NL103634C (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL134633C (en) * | 1959-10-07 | |||
| US3019159A (en) * | 1960-05-11 | 1962-01-30 | American Cyanamid Co | Novel phosphorodithioates and methods for preparing the same |
| DE1173723B (en) * | 1960-09-21 | 1964-07-09 | Basf Ag | Preparations for the control of insects |
| DE2727479A1 (en) * | 1977-06-18 | 1979-01-04 | Bayer Ag | INSECTICIDES AND ACARICIDES |
| CN112010894B (en) * | 2020-08-17 | 2023-08-11 | 湖州师范学院 | Phosphorothioate compound, nonaqueous lithium ion battery electrolyte containing phosphorothioate compound and lithium ion battery |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2693483A (en) * | 1952-03-06 | 1954-11-02 | Dow Chemical Co | Propynyl phosphate compounds |
-
0
- NL NL103634D patent/NL103634C/xx active
- BE BE571029D patent/BE571029A/xx unknown
-
1957
- 1957-09-24 DE DEF24013A patent/DE1063148B/en active Pending
-
1958
- 1958-09-01 CH CH6349358A patent/CH374649A/en unknown
- 1958-09-04 GB GB2848658A patent/GB860944A/en not_active Expired
- 1958-09-08 FR FR1203242D patent/FR1203242A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1063148B (en) | 1959-08-13 |
| NL103634C (en) | |
| BE571029A (en) | |
| FR1203242A (en) | 1960-01-15 |
| CH374649A (en) | 1964-01-31 |
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