GB823732A - Thiophosphoric acid esters - Google Patents
Thiophosphoric acid estersInfo
- Publication number
- GB823732A GB823732A GB35752/56A GB3575256A GB823732A GB 823732 A GB823732 A GB 823732A GB 35752/56 A GB35752/56 A GB 35752/56A GB 3575256 A GB3575256 A GB 3575256A GB 823732 A GB823732 A GB 823732A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- reaction
- dialkyl
- acids
- thiophosphoric
- 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
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 4
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- -1 sulphonyl- Chemical group 0.000 abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Chemical group 0.000 abstract 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 abstract 1
- 235000011007 phosphoric acid Nutrition 0.000 abstract 1
- 150000003016 phosphoric acids Chemical class 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 150000003582 thiophosphoric acids 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)
Abstract
The invention comprises thiophosphoric esters of formula <FORM:0823732/IV (b)/1> wherein R and R2 are C1-4 alkyl, R1= C1-4 alkyl which may be substituted by chlorine, A is alkylene containing at least 2 carbon atoms, X is oxygen or sulphur and Y is S, SO or SO2. Preparative methods include: reaction of salts of O,O-dialkyl thiophosphoric acids with alkyl-mercapto- (or sulphoxyl- or sulphonyl-) alkyl halides; reaction of dialkyl phosphites with alkylrhodanides; reaction of dialkyl phosphoric or thionophosphoric acid halides with alkyl-mercaptoalkyl mercaptans; reaction of 5 - (b - haloalkyl -) - O,O - dialkylthiophosphates with mercaptans; addition of O,O-dialkylthiophosphoric acids to vinylalkylsulphones; reaction of alkylsulphonyl-alkyl-sulphohalides with O,O-dialkyl phosphoric acids. The sulphoxyl and sulphonyl compounds may be prepared by oxidizing the corresponding mercapto compounds, e.g. as in Specifications 795,860 and 804,141 respectively. The products are insecticides (see Group VI). Specifications 691,374, 795,340 and 815,960 also are referred to.ALSO:Pesticidal compositions comprise thiophosphoric esters of formula <FORM:0823732/VI/1> wherein R and R2 are C1-4 alkyl, R1 is C1-4 alkyl which may be substituted by chlorine, A is alkylene containing at least 2 carbon atoms, X is oxygen or sulphur and Y is S, SO or SO2 along with solid or liquid carriers. Concentrations of 0.00001 to about 1% are generally effective.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE350963X | 1955-11-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB823732A true GB823732A (en) | 1959-11-18 |
Family
ID=6265505
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB35752/56A Expired GB823732A (en) | 1955-11-22 | 1956-11-22 | Thiophosphoric acid esters |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2952700A (en) |
| BE (1) | BE552774A (en) |
| CH (1) | CH350963A (en) |
| FR (1) | FR1168934A (en) |
| GB (1) | GB823732A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115232164A (en) * | 2022-07-04 | 2022-10-25 | 新乡医学院 | Preparation method of sulfuryl-substituted thiophosphate compound |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3151147A (en) * | 1961-10-12 | 1964-09-29 | Shell Oil Co | Omicron, omicron-dialkyl omicron-1-sulfonylvinyl and omicron, omicron-dialkyl omicron-1-sulfinylvinyl phosphates |
| BE618390A (en) * | 1961-06-03 | |||
| BE622125A (en) * | 1961-09-06 | |||
| US3660543A (en) * | 1969-03-04 | 1972-05-02 | Exxon Research Engineering Co | S-2-hydrocarbylthio-alkyl esters of thiophosphorus acids |
| US3742097A (en) * | 1969-12-10 | 1973-06-26 | Exxon Research Engineering Co | Process for preparing diadducts of hydrocarbylthiophosphoric acids |
| US3878267A (en) * | 1973-05-09 | 1975-04-15 | American Cyanamid Co | Oxygenated derivatives of s-(tert-butylthio)methyl o,o-diethyl phosphorodithioate and phosphorothioate |
| US3939263A (en) * | 1973-05-09 | 1976-02-17 | American Cyanamid Company | Methods of combatting insects and acarina using oxygenated derivatives of S-(tert-bulythio)methyl O,O-diethyl phosphorodithioate and phosphorothioate |
| US4299783A (en) * | 1980-04-28 | 1981-11-10 | Chevron Research Company | 1-Alkylsulfonyl-3-substituted phosphinylthio- or phosphinothioylthio-propenes |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2565920A (en) * | 1948-03-26 | 1951-08-28 | American Cyanamid Co | Triesters of dithiophosphoric acid |
| US2565921A (en) * | 1948-03-26 | 1951-08-28 | American Cyanamid Co | Condensation of o, o-diesters of dithiophosphoric acid and aliphatic alcohols or mercaptans with higher aliphatic aldehydes |
| US2596076A (en) * | 1948-03-26 | 1952-05-06 | American Cyanamid Co | Dithiophosphate esters as insecticides |
| US2597534A (en) * | 1949-05-07 | 1952-05-20 | Bayer Ag | Neutral esters of thiolphosphoric acid |
| DE836349C (en) * | 1950-05-10 | 1952-04-10 | Bayer Ag | Process for the preparation of neutral esters of thiophosphoric acid |
| DE876691C (en) * | 1951-07-06 | 1953-05-18 | Bayer Ag | Process for the preparation of dithiophosphoric acid esters |
| DE876692C (en) * | 1951-07-07 | 1953-05-18 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
| NL184060B (en) * | 1952-12-31 | Basf Ag | PROCESS FOR THE PROCESSING OF CYCLOHEXANOL AND CYCLOHEXANONE CONTAINING REACTION MIXTURES. |
-
0
- BE BE552774D patent/BE552774A/xx unknown
-
1956
- 1956-11-12 CH CH350963D patent/CH350963A/en unknown
- 1956-11-22 FR FR1168934D patent/FR1168934A/en not_active Expired
- 1956-11-22 GB GB35752/56A patent/GB823732A/en not_active Expired
-
1957
- 1957-03-12 US US645403A patent/US2952700A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115232164A (en) * | 2022-07-04 | 2022-10-25 | 新乡医学院 | Preparation method of sulfuryl-substituted thiophosphate compound |
Also Published As
| Publication number | Publication date |
|---|---|
| CH350963A (en) | 1960-12-31 |
| US2952700A (en) | 1960-09-13 |
| BE552774A (en) | |
| FR1168934A (en) | 1958-12-18 |
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