GB1024032A - New dithiophosphoric acid esters and pesticidal compositions containing them - Google Patents
New dithiophosphoric acid esters and pesticidal compositions containing themInfo
- Publication number
- GB1024032A GB1024032A GB2392062A GB2392062A GB1024032A GB 1024032 A GB1024032 A GB 1024032A GB 2392062 A GB2392062 A GB 2392062A GB 2392062 A GB2392062 A GB 2392062A GB 1024032 A GB1024032 A GB 1024032A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diethyl
- phosphorodithioate
- ethyl
- sulphur
- oxygen
- 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
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 System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6539—Five-membered rings
-
- 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 System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
- C07F9/653—Five-membered rings
Abstract
The invention comprises organo-phosphorus compounds of formula <FORM:1024032/C2/1> wherein R1 and R2 are the same or different C1 to C3 alkyl groups, X and Y are either both oxygen, both sulphur, or X is oxygen and Y is sulphur. The compounds are prepared:-(A) when X and Y are both oxygen or both sulphur, by reaction of an N-2-haloethyl-substituted oxalidinone or thiazolidonone with an O,O-dialkyl phosphorodithioate, or (B) when X is O and Y is S, by partial oxidation of the corresponding thiazolidinthione. In reaction (A), the dithioate is that of a monovalent cation such as ammonium or alkali metal, or the free acid, and the reaction may be performed in an organic solvent (e.g. benzene, tetrahydrofuran, lower alkanol), at elevated temperature; when the acid is used, zinc chloride may be used as a catalyst. Reaction (B) is suitably performed at about 25 DEG C. using, as oxidizing agent, H2O2 in glacial acetic acid. Examples are given for the preparation of: (1) (i) N-2-hydroxy-ethyl-2-thiazolidinthione from diethanolamine and CS2 in aqueous alkali; (ii) chlorination of the said product of (i) with thionyl chloride; (iii) reaction of the chlorinated product with O,O-diethyl-dithio phosphoric acid ammonium salt to give O,O-diethyl-S-b -(thiazolid-2-thione-3-yl) - ethyl phosphorodithioate; (2) the corresponding preparation of the dimethyl analogue of (1) (iii), using O,O-dimethyl phosphorodithioate ammonium salt; (3) preparation of N-2-hydroxyethyl-2-oxazolidonone from diethanolamine and ethyl trichloroacetate, followed by reactions analogous to (1) (ii) and (1) (iii) to give O,O - diethyl - S - b - (oxazolid - 2 - one - 3 - yl) - ethyl phosphorodithioate; and (4) partial oxidation of O,O-diethyl-S-b -(thiazolid-2-thione-3-yl)-ethyl phosphorodithioate to give O,O-diethyl - S - b (thiazolid - 2 - one - 3 - yl) ethyl phosphorodithioate, using H2O2 and glacial acetic acid. The compounds are useful as pesticides (see Division A5).ALSO:Pesticidal compositions comprise compounds of formula <FORM:1024032/A5-A6/1> wherein R1 and R2 are the same or different C1 to C3 alkyl groups, X and Y are either both oxygen, both sulphur, or X is oxygen and Y is sulphur (see Division C2), together with an acceptable carrier. Other ingredients which may be present are dispersing, wetting or surface active agents, stickers, thickening agents, and emulsifying agents. Forms taken by the compositions include granules, dust (suitably in a wettable or dispersible powder form), spray or drench in water, or water/oil emulsion, or together with a thermoplastic or thermosetting resin. Examples are given for (1) a miscible oil composition, of O, O-diethyl-S-b -(thiazolid-2-thione-3-yl)-ethyl phosphorodithioate, with methyl naphthalenes, and, as emulsifier, a mixture of an alkylaryl-polyethylene oxide condensate and a calcium alkylaryl sulphonate; (2) a dispersible powder, comprising the same active ingredient as (1), with a kieselguhr absorbent and disodium methylene dinaphthalene sulphonic acid as a surface active agent.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2392062A GB1024032A (en) | 1962-06-21 | 1962-06-21 | New dithiophosphoric acid esters and pesticidal compositions containing them |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2392062A GB1024032A (en) | 1962-06-21 | 1962-06-21 | New dithiophosphoric acid esters and pesticidal compositions containing them |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1024032A true GB1024032A (en) | 1966-03-30 |
Family
ID=10203436
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2392062A Expired GB1024032A (en) | 1962-06-21 | 1962-06-21 | New dithiophosphoric acid esters and pesticidal compositions containing them |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB1024032A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0146748A1 (en) * | 1983-11-11 | 1985-07-03 | Ishihara Sangyo Kaisha, Ltd. | Organophosphorus compound, process for its preparation and insecticidal, miticidal or nematicidal composition containing it |
CN101445491B (en) * | 2008-12-26 | 2011-08-17 | 山东师范大学 | Thiazolinone derivative and preparation method and application thereof |
-
1962
- 1962-06-21 GB GB2392062A patent/GB1024032A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0146748A1 (en) * | 1983-11-11 | 1985-07-03 | Ishihara Sangyo Kaisha, Ltd. | Organophosphorus compound, process for its preparation and insecticidal, miticidal or nematicidal composition containing it |
US4590182A (en) * | 1983-11-11 | 1986-05-20 | Ishihara Sangyo Kaisha Ltd. | Organophosphorus compound and insecticidal, miticidal or nematicidal composition containing it |
CN101445491B (en) * | 2008-12-26 | 2011-08-17 | 山东师范大学 | Thiazolinone derivative and preparation method and application thereof |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB1019570A (en) | Asymmetric thiol-and thionothiol-phosphoric acid esters | |
ES8200651A1 (en) | Urea derivatives, process for their preparation and their use as insecticides. | |
GB1024032A (en) | New dithiophosphoric acid esters and pesticidal compositions containing them | |
US3663665A (en) | O-cycloalkyl-s-alkyl-o-halophenyl-phosphorothiolates | |
GB844037A (en) | Compositions for combating rodents | |
GB977819A (en) | New thiol phosphoric acid esters | |
GB898418A (en) | Thiophosphoric acid esters | |
GB974561A (en) | Esters of phosphonothioic acids and compositions containing the same | |
US2999874A (en) | Esters of phosphoric and thiophosphoric acids containing sulfoxide groups and process for their production | |
GB1168644A (en) | Pesticidal Compositions | |
GB898910A (en) | Phosphorothioic esters and process for obtaining them | |
US2770568A (en) | P-chlorobenzyl p-chlorophenyl sulfide and acaricidal compositions containing the same | |
US2929759A (en) | Fluoro-substituted phosphonic ester pesticides | |
US3591682A (en) | Aminoalkyl phosphite fungicides and use thereof in agriculture | |
GB913229A (en) | Phosphonic thionophosphonic phosphinic and thionophosphinic acid esters of ª-- and ª--naphthols and processes for their production | |
US3488425A (en) | Process for combatting insects with bis - (heptafluoroisopropoxymethyl) benzene sulfonates | |
US2777792A (en) | Pest combating agents | |
US3201444A (en) | Omicron-alkyl-omicron-cycloalkyl thiophosphoric acid s-phenylesters | |
US3172804A (en) | Method of controlling nematodes | |
US3128225A (en) | Diphenylmethyl esters of o,o-dialkyl monothio- and dithiophosphoric acids and pesticidal methods using same | |
US3658873A (en) | Methylene-bis-(phenyl-sulfide)-4-phenylsulfonic acid esters | |
US3472933A (en) | Pesticidal preparations containing carbonyl and thiocarbonyl phosphates and method of employing the same | |
US3036952A (en) | Alkyne substituted phosphate and thiophosphate esters | |
GB1314494A (en) | Pyridazinothionophosphoric phosphonic acid esters process for their preparation and their use as insecticides and acaricides | |
IL69066A0 (en) | Thiolphosphoric acid esters,their preparation and pesticidal compositions containing them |