GB808879A - Thiophosphoric acid esters - Google Patents
Thiophosphoric acid estersInfo
- Publication number
- GB808879A GB808879A GB21241/57A GB2124157A GB808879A GB 808879 A GB808879 A GB 808879A GB 21241/57 A GB21241/57 A GB 21241/57A GB 2124157 A GB2124157 A GB 2124157A GB 808879 A GB808879 A GB 808879A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diethyl
- methylmercapto
- methylbenzyl
- phosphorothiolothionate
- phosphorothiolate
- 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
- -1 2 - ethylmercapto - 5 - methylbenzyl Chemical group 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 229910001868 water Inorganic materials 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- XPKDQBYOXNXKGG-UHFFFAOYSA-N 2-(chloromethyl)-4-methyl-1-methylsulfanylbenzene Chemical compound CSC1=CC=C(C)C=C1CCl XPKDQBYOXNXKGG-UHFFFAOYSA-N 0.000 abstract 1
- FFAQJRFGTTWEQZ-UHFFFAOYSA-N 2-(chloromethyl)-4-methyl-1-methylsulfonylbenzene Chemical compound CC1=CC=C(S(C)(=O)=O)C(CCl)=C1 FFAQJRFGTTWEQZ-UHFFFAOYSA-N 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000000443 aerosol Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 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
- 239000004305 biphenyl Substances 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 abstract 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 abstract 1
- 239000012895 dilution Substances 0.000 abstract 1
- 238000010790 dilution Methods 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 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
- 238000000034 method Methods 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 229920000151 polyglycol Polymers 0.000 abstract 1
- 239000010695 polyglycol Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001174 sulfone group Chemical group 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 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
- C07F9/1653—Esters of thiophosphoric acids with arylalkanols
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises thiophosphoric esters of the general formula: <FORM:0808879/IV (b)/1> where R, R1, R2 and R3 are C1-4 alky groups and Z is 0, 1 or 2. They are prepared by reacting (1-alkylmercapto)- or (1-alkylsulphoxyl)- or (1-alkylsulphonyl)-2-halomethyl-4-alkyl benzenes with salts (especially alkali metal or ammonium salts) of o,o-dialkylthioor thionothiolphosphoric acids, preferably at slightly elevated temperatures, e.g. 20-80 DEG C., and in the presence of an inert solvent such as a lower aliphatic alcohol, lower aliphatic ketone or aromatic hydrocarbon. The chloromethyl compounds are preferred. The 1-alkylmercapto - 2 - halomethyl - 4 - alkylbenzenes may be obtained by reaction of 1-alkylmercapto-4-alkylbenzenes with formaldehyde and a hydrohalic acid. They may be oxidized to the sulphoxides and sulphones by known methods. Alternatively the oxidation may be effected on the thiophosphoric ester reaction products. The products are insecticides (see Group VI). Examples describe the preparation of: O,O-dimethyl-, -diethyl-, and -diisopropyl-S-(2-methylmercapto - 5 - methylbenzyl) phosphorothiolate; O,O-diethyl-S-(2-methylmercapto-5-ethylbenzyl) phosphorothiolate; O,O-diethyl-S - (2 - ethylmercapto - 5 - methylbenzyl) phosphorothiolate; O,O-dimethyl-, -diethyl- and -diisopropyl - S - (2 - methylmercapto - 5 - methyl) phosphorothiolothionate; O,O-diethyl-S - (2 - ethylmercapto - 5 - methylbenzyl) phosphorothiolothionate; O,O-diethyl-S-(2-methylmercapto - 5 - ethylbenzyl) phosphorothiolothionate; O,O-diethyl-S-(2-methylsulphonyl-5-methylbenzyl) phosphorothiolate; and O,O-diethyl - S - (2 - methylsulphoxyl - 5 - methyl) phosphorothiolothionate. 1 - Methylsulphoxyl - and 1 - methylsulphonyl-2-chloromethyl-4-methylbenzene used as starting materials are prepared by the action of H2O2 in glacial acetic acid at 0 DEG and 50 DEG C. respectively or 2 - chloromethyl - 4 - methylthioanisole.ALSO:Insecticidal and plant-protecting compositions comprise thiophosphoric esters of the general formula <FORM:0808879/VI/1> where R, R1, R2 and R3 are C1-4 alkyl groups and Z is 0, 1 or 2. (For preparation see Group IV (b)). They may be applied in dilution or solution with solid or liquid carriers such as chalk, talc, bentonite, water, alcohols and liquid hydrocarbons, or as aerosols. They may be combined with other pesticides. Generally, concentrations of 0.0001 to 1 per cent are used. In an example, a composition containing 0.01 per cent of O,O-diisopropyl-S-(2-methylmercapto - 5 - methylbenzyl) dithiophosphate, dimethyl formamide, a benzyl hydroxy diphenyl polyglycol ether, and water is prepared.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0024992 | 1958-02-06 | ||
| DEF20758A DE1035153B (en) | 1958-02-06 | 1958-02-06 | Process for the preparation of insecticidally active thiophosphoric acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB808879A true GB808879A (en) | 1959-02-11 |
Family
ID=25973980
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21241/57A Expired GB808879A (en) | 1958-02-06 | 1957-07-04 | Thiophosphoric acid esters |
| GB4006/59A Expired GB864433A (en) | 1958-02-06 | 1959-02-04 | Thiophosphoric acid esters |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4006/59A Expired GB864433A (en) | 1958-02-06 | 1959-02-04 | Thiophosphoric acid esters |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2938919A (en) |
| CH (2) | CH359146A (en) |
| DE (2) | DE1035153B (en) |
| FR (1) | FR1178349A (en) |
| GB (2) | GB808879A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL136286C (en) * | 1962-01-24 | |||
| NL302624A (en) * | 1963-01-04 | |||
| US3933947A (en) * | 1970-03-25 | 1976-01-20 | Bayer Aktiengesellschaft | O-ethyl-S-propyl-S-benzyl-phosphorodithiolates |
| JPS57183796A (en) * | 1981-04-06 | 1982-11-12 | Nippon Tokushu Noyaku Seizo Kk | Preparation of organophosphoric acid ester substituted with alkylsulfinyl group |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE830509C (en) * | 1950-05-24 | 1952-02-04 | Bayer Ag | Process for the preparation of neutral esters of thiophosphoric acid |
| DE885176C (en) * | 1951-10-02 | 1953-08-03 | Bayer Ag | Pest repellants |
| NL95652C (en) * | 1955-03-05 | |||
| DE949231C (en) * | 1955-05-03 | 1956-09-13 | Bayer Ag | Process for the preparation of chlorinated benzyl esters of thiol or thionothiol phosphoric acids |
| DE1018053B (en) * | 1955-10-29 | 1957-10-24 | Bayer Ag | Process for the preparation of S-chlorobenzyl esters of O, O-dialkyl-thiolphosphoric acid |
-
0
- DE DENDAT1074034D patent/DE1074034B/en active Pending
-
1957
- 1957-06-21 CH CH359146D patent/CH359146A/en unknown
- 1957-07-04 GB GB21241/57A patent/GB808879A/en not_active Expired
- 1957-07-10 FR FR1178349D patent/FR1178349A/en not_active Expired
-
1958
- 1958-02-06 DE DEF20758A patent/DE1035153B/en active Pending
-
1959
- 1959-01-23 CH CH6868459A patent/CH367832A/en unknown
- 1959-01-27 US US789259A patent/US2938919A/en not_active Expired - Lifetime
- 1959-02-04 GB GB4006/59A patent/GB864433A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH359146A (en) | 1961-12-31 |
| FR1178349A (en) | 1959-05-06 |
| CH367832A (en) | 1963-03-15 |
| DE1074034B (en) | 1960-01-28 |
| GB864433A (en) | 1961-04-06 |
| US2938919A (en) | 1960-05-31 |
| DE1035153B (en) | 1958-07-31 |
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