GB832990A - New basic ester of phosphorothiolic acid and pesticidal compositions containing it - Google Patents
New basic ester of phosphorothiolic acid and pesticidal compositions containing itInfo
- Publication number
- GB832990A GB832990A GB3187456A GB3187456A GB832990A GB 832990 A GB832990 A GB 832990A GB 3187456 A GB3187456 A GB 3187456A GB 3187456 A GB3187456 A GB 3187456A GB 832990 A GB832990 A GB 832990A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sodium
- formula
- oet
- mixture
- compound
- 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
- 239000002253 acid Substances 0.000 title abstract 10
- 239000000203 mixture Substances 0.000 title abstract 9
- 150000002148 esters Chemical class 0.000 title abstract 5
- 230000000361 pesticidal effect Effects 0.000 title abstract 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 8
- 229910052708 sodium Inorganic materials 0.000 abstract 8
- 239000011734 sodium Substances 0.000 abstract 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 6
- 238000010438 heat treatment Methods 0.000 abstract 6
- 229910052751 metal Inorganic materials 0.000 abstract 5
- 239000002184 metal Substances 0.000 abstract 5
- 238000010992 reflux Methods 0.000 abstract 5
- 150000003839 salts Chemical class 0.000 abstract 5
- 239000011230 binding agent Substances 0.000 abstract 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 229940075930 picrate Drugs 0.000 abstract 3
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 abstract 2
- 229910019142 PO4 Inorganic materials 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- 239000012752 auxiliary agent Substances 0.000 abstract 2
- 239000003701 inert diluent Substances 0.000 abstract 2
- 239000004615 ingredient Substances 0.000 abstract 2
- 235000015097 nutrients Nutrition 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 2
- 239000010452 phosphate Substances 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- -1 sodium Chemical class 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- XRIBIDPMFSLGFS-UHFFFAOYSA-N 2-(dimethylamino)-2-methylpropan-1-ol Chemical compound CN(C)C(C)(C)CO XRIBIDPMFSLGFS-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 abstract 1
- 239000004141 Sodium laurylsulphate Substances 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- 150000001340 alkali metals 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
- 239000004202 carbamide Substances 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- PHHWLDOIMGFHOZ-UHFFFAOYSA-L disodium;dinaphthalen-1-ylmethanedisulfonate Chemical compound [Na+].[Na+].C1=CC=C2C(C(C=3C4=CC=CC=C4C=CC=3)(S(=O)(=O)[O-])S([O-])(=O)=O)=CC=CC2=C1 PHHWLDOIMGFHOZ-UHFFFAOYSA-L 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 239000000428 dust Substances 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000003292 glue Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 abstract 1
- 235000019341 magnesium sulphate Nutrition 0.000 abstract 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 1
- 230000001931 phytocidal effect Effects 0.000 abstract 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 238000009736 wetting Methods 0.000 abstract 1
- 210000002268 wool Anatomy 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises O,O1-diethyl S-(b -dimethylamino - b - methyl) propyl phosphorothiolate of the formula <FORM:0832990/IV (b)/1> and acid addition salts thereof. Specified acid addition salts are the hydrogen oxalate, toluene-p-sulphonate, hydrochloride, phosphate and picrate. The ester may be obtained by heating a compound of the formula S : P(OET)(OET)Y wherein Y is a halogen atom either with a compound of the formula <FORM:0832990/IV (b)/2> wherein, of R3 and R4, one is hydrogen and the other a methyl radical, in the presence of an acid binding agent, or with a metal derivative of the said compound of the formula <FORM:0832990/IV (b)/3> wherin M is a metal atom and R3 and R4 are as defined above. Suitable acid binding agents are alkali metal carbonates, e.g. sodium carbonate and a suitable metal derivative is an alkali metal, e.g. sodium, derivative. The reaction may be carried out in an inert diluent e.g. benzene. The ester may also be obtained by heating a compound of the formula <FORM:0832990/IV (b)/4> wherein Y, R3 and R4 are as defined above either with a compound of the formula O= P(OET)(OET)SH in the presence of an acid binding agent or with a metal derivative of such compound of the formula O : P(OET)(OET) SM wherein M is a metal atom, especially sodium. The reaction may be carried out in the presence of an inert diluent, e.g. ethanol. In examples the ester is obtained by (1) heating a mixture of 1-dimethylamino-2-methylpropanol-2, sodium and benzene under reflux until the sodium no longer effervesces, removing residual traces of sodium by filtration, and then adding O,O1 - diethyl - phosphorochloridothionate to the filtrate and heating the mixture under reflux for 4 hours; (2) heating a mixture of 2-dimethylamino - 2 - methyl - propanol - 1, sodium and toluene under reflux until the sodium is dissolved, cooling to 20-25 DEG C. and then adding dropwise O,O1-diethylphosphorochloridothionate and refluxing the mixture for 2 hours; and (3) by keeping a mixture of basic chloride (prepared by reacting thionyl chloride and 2 - dimethylamino - 2 - methyl propanol-1), sodium O,O1 - diethylphosphorothiolate and ethanol at 18-23 DEG C. for 18 hours and then heating the mixture under reflux for 6 hours. In each case the product after separation from the reaction mixture is treated with picric acid in ethanol to form the picrate. The other specified acid addition salts may be obtained in a similar manner by mixing equimolar amounts of the basic ester and the appropriate acid in a mutual organic solvent with subsequent evaporation of the solvent where necessary. The products have pesticidal properties (see Group VI). Specifications 738,839 and 772,731 are referred to.ALSO:A pesticidal composition comprises O,O1-diethyl S - (b - dimethylamino - b - methyl) - propyl phosphorothioate of the formula <FORM:0832990/VI/1> and/or acid addition salt thereof (see Group IV (b)) as the active pesticidal ingredient or ingredients. Specified acid addition salts are the hydrogen oxalate, the toluene-p-sulphonate, the hydrochloride, phosphate and picrate. The pesticidal composition may contain a carrier and, if desired, an auxiliary agent and/or a plant nutrient. Specified carriers are talc, kieselguhr, bentonite, powdered chalk, water, and non-phytocidal organic solvents. Specified auxiliary agents are dust binding agents, e.g. spindle oil, glycerol and wool fat, wetting, spreading and dispersing agents, e.g. sodium dinaphthylmethane disulphonate and sodium lauryl sulphate and sticking agents, e.g. glue and resin. Specified plant nutrients are urea and magnesium sulphate. Specifications 738,839 and 772,731 are referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3187456A GB832990A (en) | 1956-10-19 | 1956-10-19 | New basic ester of phosphorothiolic acid and pesticidal compositions containing it |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3187456A GB832990A (en) | 1956-10-19 | 1956-10-19 | New basic ester of phosphorothiolic acid and pesticidal compositions containing it |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB832990A true GB832990A (en) | 1960-04-21 |
Family
ID=10329691
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3187456A Expired GB832990A (en) | 1956-10-19 | 1956-10-19 | New basic ester of phosphorothiolic acid and pesticidal compositions containing it |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB832990A (en) |
-
1956
- 1956-10-19 GB GB3187456A patent/GB832990A/en not_active Expired
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