GB825477A - Thiophosphoric acid esters - Google Patents
Thiophosphoric acid estersInfo
- Publication number
- GB825477A GB825477A GB1941258A GB1941258A GB825477A GB 825477 A GB825477 A GB 825477A GB 1941258 A GB1941258 A GB 1941258A GB 1941258 A GB1941258 A GB 1941258A GB 825477 A GB825477 A GB 825477A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bis
- methylene
- acid esters
- iodide
- bromide
- 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- 230000000749 insecticidal effect Effects 0.000 abstract 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 150000003863 ammonium salts Chemical class 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 238000007865 diluting Methods 0.000 abstract 1
- 239000003085 diluting agent Substances 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
- 125000003827 glycol group Chemical group 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- -1 methylene halide Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 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
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000000243 solution Substances 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
- C07F9/1652—Polyol derivatives esterified at least twice by thiophosphoric acid groups
-
- 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
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 methylene-bis-(thionothiol-phosphoric acid esters) of the general formula <FORM:0825477/IV (b)/1> wherein R1 and R2 are like or unlike C1-C4 alkyl radicals. They may be obtained by reacting a methylene halide (e.g. chloride, bromide or iodide) with a salt, preferably an alkali metal or ammonium salt, of an appropriate O,O-dialkyl dithio phosphoric acid in aqueous solution at an elevated temperature. Specified products are the bis-(O,O-dimethyl), bis-(O,O-diethyl), bis-(O,O-di-isopropyl) and bis-(O,O-di-n-propyl) esters. If the reaction of methylene chloride, bromide or iodide with the alkali metal or ammonium salts is carried out in an organic solvent (e.g. an alcohol or ketone) instead of in aqueous solution, the yields are stated to be unsatisfactory. The products have good insecticidal properties (see Group VI).ALSO:An insecticidal composition comprises a solid or liquid carrier or diluent and one or more methylene - bis - (thionothiolphosphoric acid esters) of the formula <FORM:0825477/VI/1> wherein R1 and R2 are C1-C4 alkyl radicals which may be the same or different (see Group IV (b)). An example is given to show the insecticidal effect of a solution prepared by mixing an ester of the above formula in which R1 and R2 are ethyl with dimethyl formamide and then adding a benzyl hydroxy diphenyl polyglycol ether containing about 10 to 15 glycol residues (as emulsifier) and diluting with water.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0023315 | 1957-06-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB825477A true GB825477A (en) | 1959-12-16 |
Family
ID=7090791
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1941258A Expired GB825477A (en) | 1957-06-24 | 1958-06-17 | Thiophosphoric acid esters |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE568696A (en) |
| CH (1) | CH378308A (en) |
| DE (1) | DE1418193A1 (en) |
| FR (1) | FR1198263A (en) |
| GB (1) | GB825477A (en) |
-
0
- BE BE568696D patent/BE568696A/xx unknown
-
1957
- 1957-06-24 DE DE19571418193 patent/DE1418193A1/en active Pending
-
1958
- 1958-06-06 CH CH6030558A patent/CH378308A/en unknown
- 1958-06-17 GB GB1941258A patent/GB825477A/en not_active Expired
- 1958-06-17 FR FR1198263D patent/FR1198263A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE568696A (en) | |
| CH378308A (en) | 1964-06-15 |
| DE1418193A1 (en) | 1968-11-21 |
| FR1198263A (en) | 1959-12-07 |
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