GB977819A - New thiol phosphoric acid esters - Google Patents
New thiol phosphoric acid estersInfo
- Publication number
- GB977819A GB977819A GB3042/63A GB304263A GB977819A GB 977819 A GB977819 A GB 977819A GB 3042/63 A GB3042/63 A GB 3042/63A GB 304263 A GB304263 A GB 304263A GB 977819 A GB977819 A GB 977819A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- alkyl
- pinacolyl
- isopropyl
- sec
- 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 thiol phosphoric acid esters Chemical class 0.000 title abstract 13
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 abstract 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Substances 0.000 abstract 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 abstract 2
- 125000000278 alkyl amino alkyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 2
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 2
- WTJUKRMAHQEZNU-UHFFFAOYSA-N 3,3-dimethylbutan-2-yloxy-hydroxy-methylperoxy-sulfanylidene-lambda5-phosphane Chemical class COOP(OC(C)C(C)(C)C)(O)=S WTJUKRMAHQEZNU-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 239000003337 fertilizer 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
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical group [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 abstract 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 150000003580 thiophosphoric acid esters Chemical class 0.000 abstract 1
- 150000003582 thiophosphoric acids Chemical class 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01R—ELECTRICALLY-CONDUCTIVE CONNECTIONS; STRUCTURAL ASSOCIATIONS OF A PLURALITY OF MUTUALLY-INSULATED ELECTRICAL CONNECTING ELEMENTS; COUPLING DEVICES; CURRENT COLLECTORS
- H01R33/00—Coupling devices specially adapted for supporting apparatus and having one part acting as a holder providing support and electrical connection via a counterpart which is structurally associated with the apparatus, e.g. lamp holders; Separate parts thereof
- H01R33/05—Two-pole devices
- H01R33/06—Two-pole devices with two current-carrying pins, blades or analogous contacts, having their axes parallel to each other
- H01R33/08—Two-pole devices with two current-carrying pins, blades or analogous contacts, having their axes parallel to each other for supporting tubular fluorescent lamp
-
- 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
-
- 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
- A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
-
- 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
-
- 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
-
- 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
- C07F9/1653—Esters of thiophosphoric acids with arylalkanols
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises compounds of formula <FORM:0977819/C1/1> where R is secondary alkyl, R1 is C1- 4 primary alkyl and R2 is unsubstituted or substituted alkyl or aralkyl. They are prepared by reacting a phosphite (RO)(R1O)P(O)H with sulphur and an alkali to give the corresponding thiophosphoric acid salt which is then alkylated or aralkylated, e.g. with a halide or tosylate. Numerous examples are given in which R is isopropyl, sec-butyl or pinacolyl, R1 is methyl and R2 is ethylmercaptomethyl, ethylmercaptoethyl, cyanomethyl, cyanoethyl, p-chlorobenzyl, p-chlorophenylmercaptomethyl, N-methylcarbamoylmethyl, or 2-methylmercapto-5-methyl benzyl. R2 may also be arylmercaptoalkyl, alkylaminoalkyl, alkoxycarbonylalkyl, alkylmercaptocarbonylalkyl or dialkylcarbamoylalkyl. The products are pesticides. The ammonium salts of O-methyl-O-isopropyl, O-methyl-O-sec-butyl and O-methyl-O-pinacolyl thiophosphoric acids are prepared by reacting the corresponding secondary phosphites with sulphur and ammonia. Specification 685,737 is referred to.ALSO:Pesticidal compositions comprise thiophosphate esters of formula <FORM:0977819/A5-A6/1> where R is secondary alkyl, R1 is C1-4 primary alkyl and R2 is unsubstituted or substituted alkyl or aralkyl together with a solid or liquid carrier. Numerous examples are given in which R is isopropyl, sec-butyl or pinacolyl, R1 is methyl and R2 is ethylmercaptomethyl, ethylmercaptoethyl, cyanomethyl, cyanoethyl, p-chlorobenzyl, p-chlorophenylmercaptomethyl, N-methylcarbamoylmethyl, or 2-methylmercapto - 5 - methylbenzyl. R2 may also be arylmercaptoalkyl, alkylaminoalkyl, alkoxycarbonylalkyl, alkylmercaptocarbonyl-alkyl or dialkylcarbamoylalkyl. Other insecticides and/or fertilizers may be present. An emulsion containing a non-ionic emulsifying agent is specified. Specification 685,737 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF35839A DE1172667B (en) | 1962-01-24 | 1962-01-24 | Process for the preparation of O, O-dialkyl-S-alkylthiolphosphoric acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB977819A true GB977819A (en) | 1964-12-16 |
Family
ID=7096175
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3042/63A Expired GB977819A (en) | 1962-01-24 | 1963-01-24 | New thiol phosphoric acid esters |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3294874A (en) |
| BR (1) | BR6346394D0 (en) |
| CH (1) | CH426776A (en) |
| DE (1) | DE1172667B (en) |
| DK (1) | DK109851C (en) |
| GB (1) | GB977819A (en) |
| NL (2) | NL288076A (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2023034A1 (en) * | 1968-11-12 | 1970-08-07 | Sumitomo Chemical Co | |
| US3897552A (en) * | 1971-08-18 | 1975-07-29 | Bayer Ag | Fungicidal and bactericidal O-alkyl-O-cyclohexyl-S-alkyl-, haloalkyl-or alkenyl-phosphorothiolates |
| US3927148A (en) * | 1971-08-19 | 1975-12-16 | Exxon Research Engineering Co | O,S{40 -Dialkyl-S-hydrocarbylthioalkyl dithiophosphates |
| JPS51136654A (en) * | 1976-04-27 | 1976-11-26 | Nippon Tokushu Noyaku Seizo Kk | Process for preparation of o-cyclohexyl-o-alkyl-s-(halo or alkenyl)pho sphorothiolate |
| US4755311A (en) * | 1986-08-14 | 1988-07-05 | The Lubrizol Corporation | Phosphorus-, sulfur- and boron-containing compositions, and lubricant and functional fluid compositions containing same |
| US5449769A (en) * | 1989-03-06 | 1995-09-12 | Gen-Probe Incorporated | Method and reagent for sulfurization of organophosphorous compounds |
| AU642673B2 (en) * | 1990-09-04 | 1993-10-28 | Gen-Probe Incorporated | Method and reagent for sulfurization of organophosphorous compounds |
| DE19502197A1 (en) * | 1995-01-25 | 1996-08-01 | Bayer Ag | Process for the preparation of thiophosphoric acid-O, O'-diesters and their salts and their use |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA494562A (en) * | 1948-02-04 | 1953-07-21 | American Cyanamid Company | Carbamylalkyl phosphates and method of preparation |
| US2494284A (en) * | 1949-01-12 | 1950-01-10 | American Cyanamid Co | Cyanoalkyl phosphates and method of preparation |
| US2597534A (en) * | 1949-05-07 | 1952-05-20 | Bayer Ag | Neutral esters of thiolphosphoric acid |
| BE539661A (en) * | 1954-09-29 | |||
| DE949231C (en) * | 1955-05-03 | 1956-09-13 | Bayer Ag | Process for the preparation of chlorinated benzyl esters of thiol or thionothiol phosphoric acids |
| DE1024509B (en) * | 1956-03-03 | 1958-02-20 | Bayer Ag | Process for the preparation of O, O-dialkyl-thiol-phosphoric acid and thiol-thionophosphoric acid esters |
| DE1074034B (en) * | 1958-02-06 | 1960-01-28 | Farbenfabriken Bayer Aktiengesellschaft, Leverkusen-Bayerwerk | Process for the preparation of thiophosphoric acid esters |
| US3020305A (en) * | 1958-08-25 | 1962-02-06 | Monsanto Chemicals | Halogen substituted alkenylthioalkyl esters of phosphorus acids |
| DE1116657B (en) * | 1960-01-22 | 1961-11-09 | Bayer Ag | Process for the preparation of derivatives of the thioic acids of phosphorus |
-
0
- NL NL136286D patent/NL136286C/xx active
- NL NL288076D patent/NL288076A/xx unknown
-
1962
- 1962-01-24 DE DEF35839A patent/DE1172667B/en active Pending
-
1963
- 1963-01-07 CH CH11563A patent/CH426776A/en unknown
- 1963-01-22 US US253070A patent/US3294874A/en not_active Expired - Lifetime
- 1963-01-23 DK DK31963AA patent/DK109851C/en active
- 1963-01-24 GB GB3042/63A patent/GB977819A/en not_active Expired
- 1963-01-24 BR BR146394/63A patent/BR6346394D0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL136286C (en) | |
| DK109851C (en) | 1968-07-15 |
| US3294874A (en) | 1966-12-27 |
| DE1172667B (en) | 1964-06-25 |
| BR6346394D0 (en) | 1973-08-09 |
| NL288076A (en) | |
| CH426776A (en) | 1966-12-31 |
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