GB822477A - Thiophosphoric acid esters and a process for their production - Google Patents
Thiophosphoric acid esters and a process for their productionInfo
- Publication number
- GB822477A GB822477A GB39262/57A GB3926257A GB822477A GB 822477 A GB822477 A GB 822477A GB 39262/57 A GB39262/57 A GB 39262/57A GB 3926257 A GB3926257 A GB 3926257A GB 822477 A GB822477 A GB 822477A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphur
- aliphatic
- compounds
- alkyl radical
- aromatic
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- 150000001875 compounds Chemical class 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
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 abstract 4
- 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- 239000007788 liquid Substances 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 239000011230 binding agent Substances 0.000 abstract 2
- 239000002917 insecticide Substances 0.000 abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- -1 mercapto-1-cyano isopropyl halide Chemical class 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- WLHCBQAPPJAULW-UHFFFAOYSA-N 4-methylbenzenethiol Chemical compound CC1=CC=C(S)C=C1 WLHCBQAPPJAULW-UHFFFAOYSA-N 0.000 abstract 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 239000003337 fertilizer Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 230000000749 insecticidal 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
- 229920000151 polyglycol Polymers 0.000 abstract 1
- 239000010695 polyglycol Substances 0.000 abstract 1
- 239000001103 potassium chloride Substances 0.000 abstract 1
- 235000011164 potassium chloride Nutrition 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 150000003573 thiols Chemical class 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:0822477/IV (a)/1> in which R is an alkyl radical, especially a C1-C4 alkyl radical, R1 is an aliphatic or aromatic radical and X is oxygen or sulphur, at least one X being sulphur. They may be obtained by reacting a 3-aliphatic (or aromatic)-mercapto - 1 - cyano - isopropyl alcohol with a halide of an O,O-dialkyl thiophosphoric acid or by reacting a 3-aliphatic (or aromatic) mercapto-1-cyano isopropyl halide with a salt (e.g. an alkali metal or ammonium salt) of an O,O-dialkyl thiol (or thionothiol-) phosphoric acid or with the free acid in the presence of an acid-binding agent. The first-mentioned reaction yields compounds in which one X is oxygen and is preferably carried out in an inert organic solvent and in the presence of an acid binding agent, especially a tertiary amine such as pyridine. The second type of reaction is also advantageously carried out in the presence of an inert organic solvent. Specified reaction temperatures in each case are between 0 DEG and 150 DEG C. Examples are given for the production of compounds in which each R is C2H5, each X is sulphur and R1 is C2H5, and CH (CH3)2 respectively and the compounds <FORM:0822477/IV (a)/2> and <FORM:0822477/IV (a)/3> The products are stated to be effective as insecticides (see Group VI). The compound C2H5SCH2CH(OH)(CH2CN) used as a starting material is obtained by adding g -chloro-b -hydroxy butyronitrile to a solution of potassium hydroxide and ethyl mercaptan in methanol and removing the precipitated potassium chloride. The compounds p-CH3.C6H4.SCH2CH(OH)(CH2CN) and (CH3)2CH.SCH2CH(OH)CH2CN are obtained similarly using p-thiocresol and isopropyl mercaptan respectively instead of ethyl mercaptan. Also the chlorides corresponding to each of these mercapto alcohols are obtained by reacting the latter with thionyl chloride in the presence of chloroform.ALSO:An insecticidal composition comprises a solid or liquid carrier and one or more thiophosphoric acid esters of the formula <FORM:0822477/VI/1> in which R is an alkyl radical, especially a C1-C4 alkyl radical, R1 is an aliphatic or aromatic radical, and X is oxygen or sulphur, at least one X being sulphur (see Group IV (b)). A specified composition comprises an aqueous solution comprising the compound <FORM:0822477/VI/2> acetone and benzyl hydroxy diphenyl polyglycol ether as emulsifier. Other liquid diluents specified are methanol, ethanol, methyl ethyl ketone and liquid hydrocarbons. Known insecticides and/or fertilizers may also be present.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE822477X | 1956-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB822477A true GB822477A (en) | 1959-10-28 |
Family
ID=6743302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB39262/57A Expired GB822477A (en) | 1956-12-21 | 1957-12-17 | Thiophosphoric acid esters and a process for their production |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB822477A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102308788A (en) * | 2011-07-07 | 2012-01-11 | 中国农业大学 | Insecticidal agricultural pesticide preparation using ionic liquid as cosolvent and method for preparing insecticidal agricultural pesticide preparation |
-
1957
- 1957-12-17 GB GB39262/57A patent/GB822477A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102308788A (en) * | 2011-07-07 | 2012-01-11 | 中国农业大学 | Insecticidal agricultural pesticide preparation using ionic liquid as cosolvent and method for preparing insecticidal agricultural pesticide preparation |
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