GB811268A - Sulphinyl-phosphoric acid esters and a process for their production - Google Patents
Sulphinyl-phosphoric acid esters and a process for their productionInfo
- Publication number
- GB811268A GB811268A GB37825/57A GB3782557A GB811268A GB 811268 A GB811268 A GB 811268A GB 37825/57 A GB37825/57 A GB 37825/57A GB 3782557 A GB3782557 A GB 3782557A GB 811268 A GB811268 A GB 811268A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- radicals
- chlorophenyl
- phenyl
- chloronitrophenyl
- 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
- -1 C1-4 alkyl radicals Chemical class 0.000 abstract 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000005840 aryl radicals Chemical group 0.000 abstract 2
- 125000000068 chlorophenyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000003995 emulsifying agent Substances 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 125000006501 nitrophenyl group Chemical group 0.000 abstract 2
- 125000003944 tolyl group Chemical group 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 239000000443 aerosol Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 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
- 239000011230 binding agent Substances 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- YTNUGSXQPKDMDA-UHFFFAOYSA-N dimethoxyphosphoryl 4-chlorobenzenesulfinate Chemical compound P(=O)(OS(=O)C1=CC=C(C=C1)Cl)(OC)OC YTNUGSXQPKDMDA-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 150000003014 phosphoric acid esters Chemical class 0.000 abstract 1
- 229920000151 polyglycol Polymers 0.000 abstract 1
- 239000010695 polyglycol Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000007921 spray Substances 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
-
- 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
- C07F9/1654—Compounds containing the structure P(=X)n-X-acyl, P(=X)n-X-heteroatom, P(=X)n-X-CN (X = O, S, Se; n = 0, 1)
-
- 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
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises phosphoric acid esters of the formula <FORM:0811268/IV (b)/1> where R is an alkyl or aryl radical and R1 and R2 are C1-4 alkyl radicals. Specific R radicals mentioned are C1-4 alkyl, phenyl, tolyl, chlorophenyl, nitrophenyl, methoxyphenyl and chloronitrophenyl radicals. They may be prepared by reacting aliphatic or aromatic sulphinic acids or their salts with O,O-dialkyl phosphorous acid halides. The free acids are used in combination with organic acid-binding agents such as tertamines, e.g. pyridine. Inert solvents such as methanol, ethanol, acetone, methyl ethyl ketone, dimethyl formamide, benzene or toluene are generally used and temperatures of 0-100 DEG C., preferably 40-60 DEG C. The products are insecticides. Examples describe the preparation of compounds where R is phenyl or p-chlorophenyl and R1 and R2 are methyl or ethyl.ALSO:Insecticidal compositions comprise sulphinylphosphoric esters of formula <FORM:0811268/VI/1> wherein R is an alkyl or aryl radical and R1 and R2 are C1-4 alkyl radicals. Specified R groups include C1-4 alkyl, phenyl, tolyl, chlorophenyl, nitrophenyl, methoxyphenyl and chloronitrophenyl groups. They may be used with solid or liquid carriers such as talc, chalk, bentonite, water, alcohols, liquid hydrocarbons or ketones. Emulsifiers may be added and the compounds applied as dusts, sprays, aerosols or in other manner. In an example, compositions comprising p-chlorophenylsulphinyl dimethyl phosphate, dimethylformamide, a benzyl hydroxy diphenyl polyglycol ether emulsifier and water are prepared.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF24038A DE1058050B (en) | 1957-09-26 | 1957-09-26 | Process for the production of thiophosphoric acid esters or phosphoric acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB811268A true GB811268A (en) | 1959-04-02 |
Family
ID=7091077
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB37825/57A Expired GB811268A (en) | 1957-09-26 | 1957-12-04 | Sulphinyl-phosphoric acid esters and a process for their production |
| GB38898/57A Expired GB812045A (en) | 1957-09-26 | 1957-12-13 | Sulphinyl-phosphoric and-thiophosphoric acid esters |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB38898/57A Expired GB812045A (en) | 1957-09-26 | 1957-12-13 | Sulphinyl-phosphoric and-thiophosphoric acid esters |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US2910500A (en) |
| BE (1) | BE562136A (en) |
| CH (1) | CH368156A (en) |
| DE (1) | DE1058050B (en) |
| FR (1) | FR1216922A (en) |
| GB (2) | GB811268A (en) |
| NL (2) | NL99399C (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3179688A (en) * | 1962-06-20 | 1965-04-20 | Monsanto Co | Phosphonyl- and thiophosphonyl-thio-nylamines and process of preparing |
| US3328360A (en) * | 1962-07-06 | 1967-06-27 | Exxon Research Engineering Co | Polymers containing phosphorus |
| US4155958A (en) * | 1977-09-26 | 1979-05-22 | Standard Oil Company (Indiana) | Beta-phosphosulfoxy alcohols |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL82724C (en) * | 1951-06-19 | |||
| US2690451A (en) * | 1951-09-28 | 1954-09-28 | Allied Chem & Dye Corp | Method for preparation of sulfur-containing esters of phosphoric acid |
| US2828241A (en) * | 1954-05-25 | 1958-03-25 | Monsanto Chemicals | O,o-dialkyl s-arylmercapto phosphoro-dithioate compositions and method of destroyinginsects |
-
0
- BE BE562136D patent/BE562136A/xx unknown
- NL NL222488D patent/NL222488A/xx unknown
- NL NL99399D patent/NL99399C/xx active
-
1957
- 1957-09-26 DE DEF24038A patent/DE1058050B/en active Pending
- 1957-10-21 FR FR749821A patent/FR1216922A/en not_active Expired
- 1957-10-30 CH CH5211457A patent/CH368156A/en unknown
- 1957-11-13 US US696029A patent/US2910500A/en not_active Expired - Lifetime
- 1957-12-04 GB GB37825/57A patent/GB811268A/en not_active Expired
- 1957-12-13 GB GB38898/57A patent/GB812045A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL222488A (en) | |
| FR1216922A (en) | 1960-04-29 |
| DE1058050B (en) | 1959-05-27 |
| BE562136A (en) | |
| GB812045A (en) | 1959-04-15 |
| CH368156A (en) | 1963-03-31 |
| NL99399C (en) | |
| US2910500A (en) | 1959-10-27 |
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