GB854351A - New phosphorus esters and process for their preparation - Google Patents
New phosphorus esters and process for their preparationInfo
- Publication number
- GB854351A GB854351A GB27676/58A GB2767658A GB854351A GB 854351 A GB854351 A GB 854351A GB 27676/58 A GB27676/58 A GB 27676/58A GB 2767658 A GB2767658 A GB 2767658A GB 854351 A GB854351 A GB 854351A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- products
- ethylene oxide
- esters
- specified
- 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
- 150000003017 phosphorus Chemical class 0.000 title 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- -1 hydroxy pyridine compound Chemical class 0.000 abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 230000000361 pesticidal effect Effects 0.000 abstract 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- PKAUZTQOCSCVLK-UHFFFAOYSA-N 2,6-dimethyl-3-nitro-1h-pyridin-4-one Chemical compound CC1=CC(=O)C([N+]([O-])=O)=C(C)N1 PKAUZTQOCSCVLK-UHFFFAOYSA-N 0.000 abstract 1
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 abstract 1
- 239000005995 Aluminium silicate Substances 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 239000002250 absorbent Substances 0.000 abstract 1
- 230000002745 absorbent Effects 0.000 abstract 1
- 239000000443 aerosol Substances 0.000 abstract 1
- 235000012211 aluminium silicate Nutrition 0.000 abstract 1
- 239000010775 animal oil Substances 0.000 abstract 1
- 150000004945 aromatic hydrocarbons 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
- 239000001506 calcium phosphate Substances 0.000 abstract 1
- 239000006229 carbon black Substances 0.000 abstract 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 239000007799 cork Substances 0.000 abstract 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 239000000428 dust Substances 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 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
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000002480 mineral oil Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- 150000003580 thiophosphoric acid esters Chemical class 0.000 abstract 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 abstract 1
- 229940078499 tricalcium phosphate Drugs 0.000 abstract 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 abstract 1
- 235000019731 tricalcium phosphate Nutrition 0.000 abstract 1
- 235000015112 vegetable and seed oil Nutrition 0.000 abstract 1
- 239000008158 vegetable oil Substances 0.000 abstract 1
- 238000009736 wetting Methods 0.000 abstract 1
- 239000000080 wetting agent Substances 0.000 abstract 1
- 239000008096 xylene Substances 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
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 esters of the formula: <FORM:0854351/IV(b)/1> in which R1 and R2 are the same or different C1-C4 alkyl radicals. They may be obtained by reacting a halogenothiophosphate of the formula Hal P(S) (OR1)(OR2) in which Hal is a halogen atom, preferably chlorine with the corresponding 4-hydroxy-3-nitro-2, 6-dimethyl-pyridine. The reaction is preferably carried out in an organic solvent medium e.g. an aliphatic alcohol or ketone or a chlorinated hydrocarbon below 150 DEG C. in the presence of an alkaline condensing agent, e.g. an alkali metal or derivative thereof e.g. hydroxide or carbonate. Instead of the free hydroxy pyridine compound an alkali metal derivative thereof may be used in which case no condensing agent is necessary. Specified products are those in which X is sulphur and R1 and R2 are each methyl, ethyl and isopropyl respectively. The products have pesticidal properties (see Group VI).ALSO:A pesticidal composition comprises one or more thiophosphoric acid esters of the formula: <FORM:0854351/VI/1> in which R1 and R2 are the same or different and are C1-C4 alkyl radicals (see Group IV (b)) in association with one or more diluents compatible with the said esters. Specified diluents are solids, e.g. talc, calcined magnesia, kieselguhr, tricalcium phosphate, cork dust, absorbent carbon black, kaolin and bentonite, and liquids such as aromatic hydrocarbons, e.g. toluene or xylene, or mineral, animal or vegetable oils or mixtures of such liquids, and acetone or dimethylacetonyl carbinol. The compositions may be in the form of aerosols or may be suspensions, emulsions or solutions in organic or aqueous organic media. Wetting, dispersing or emulsifying agents of ionic or non-ionic type, may be present, e.g. sulphated ricinoleates, quaternary ammonium derivatives or products based on condensates of ethylene oxide, e.g. the condensates of ethylene oxide with octyl phenol, or the fatty acid esters of anhydrosorbitols which have been rendered soluble by condensation of the free hydroxyl groups with ethylene oxide. Specified ester products are those in which R1 and R2 in the formula are each methyl, ethyl, and isopropyl.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR854351X | 1957-09-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB854351A true GB854351A (en) | 1960-11-16 |
Family
ID=9327706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27676/58A Expired GB854351A (en) | 1957-09-27 | 1958-08-28 | New phosphorus esters and process for their preparation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB854351A (en) |
-
1958
- 1958-08-28 GB GB27676/58A patent/GB854351A/en not_active Expired
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