GB783281A - New pesticidal basic esters of phosphorothiolothionic acid - Google Patents
New pesticidal basic esters of phosphorothiolothionic acidInfo
- Publication number
- GB783281A GB783281A GB2321254A GB2321254A GB783281A GB 783281 A GB783281 A GB 783281A GB 2321254 A GB2321254 A GB 2321254A GB 2321254 A GB2321254 A GB 2321254A GB 783281 A GB783281 A GB 783281A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphorothiolothionate
- atom
- diethyl
- attached
- formula
- 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
- 150000002148 esters Chemical class 0.000 title abstract 4
- 230000000361 pesticidal effect Effects 0.000 title abstract 3
- 239000002253 acid Substances 0.000 title 1
- -1 alkyl radicals Chemical class 0.000 abstract 8
- 125000004432 carbon atom Chemical group C* 0.000 abstract 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 6
- 229910052757 nitrogen Inorganic materials 0.000 abstract 6
- 229910052799 carbon Inorganic materials 0.000 abstract 5
- 235000015097 nutrients Nutrition 0.000 abstract 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 abstract 4
- 125000001931 aliphatic group Chemical group 0.000 abstract 4
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 4
- 239000012752 auxiliary agent Substances 0.000 abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 abstract 4
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 3
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 3
- 125000004437 phosphorous atom Chemical group 0.000 abstract 3
- 229910052698 phosphorus Inorganic materials 0.000 abstract 3
- 229920006395 saturated elastomer Polymers 0.000 abstract 3
- OZGAJMXOQKGWKB-UHFFFAOYSA-N 1-(dipropylamino)-3-ethylsulfanylpropan-2-ol Chemical compound C(C)SCC(CN(CCC)CCC)O OZGAJMXOQKGWKB-UHFFFAOYSA-N 0.000 abstract 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 abstract 2
- 239000004141 Sodium laurylsulphate Substances 0.000 abstract 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 239000000440 bentonite Substances 0.000 abstract 2
- 229910000278 bentonite Inorganic materials 0.000 abstract 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 abstract 2
- 239000004202 carbamide Substances 0.000 abstract 2
- 239000000969 carrier Substances 0.000 abstract 2
- 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 2
- 239000003292 glue Substances 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 abstract 2
- 235000019341 magnesium sulphate Nutrition 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 230000001931 phytocidal effect Effects 0.000 abstract 2
- 239000011347 resin Substances 0.000 abstract 2
- 229920005989 resin Polymers 0.000 abstract 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- 239000000454 talc Substances 0.000 abstract 2
- 229910052623 talc Inorganic materials 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 210000002268 wool Anatomy 0.000 abstract 2
- IQHIFJVDTZSMEK-UHFFFAOYSA-N 1-chloro-3-ethylsulfanylpropan-2-ol Chemical compound CCSCC(O)CCl IQHIFJVDTZSMEK-UHFFFAOYSA-N 0.000 abstract 1
- JVPSQYCVDARKSD-UHFFFAOYSA-N 2-chloro-3-ethylsulfanyl-N,N-dipropylpropan-1-amine Chemical compound ClC(CN(CCC)CCC)CSCC JVPSQYCVDARKSD-UHFFFAOYSA-N 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 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 phosphorothiolothionic esters of the formula: S = P(OR1)(OR2)-S-LX wherein R1 and R2 are alkyl radicals, L is a saturated aliphatic hydrocarbon radical in which the carbon atoms may be interrupted by an oxygen atom, a sulphur atom or an N-Alkyl substituent, and X represents a secondary aliphatic or heterocyclic amino radical attached to L through the amine nitrogen atom, said nitrogen atom not being attached to the same carbon atom as the sulphur atom linking L with the phosphorus atom. The compounds are prepared (1) by reacting an alkali metal salt of a dialkyl phosphorothiolothionate of the formula: S = P(OR1)(OR2)-S Met wherein Met represents an alkali metal, with an aminoalkyl derivative of formula YLX1, wherein Y represents halogen and X1 represents a secondary aliphatic or heterocyclic amino radical not attached to the same carbon atom as Y; and (2) by reacting a dialkyl phosphorohalidothionate of the formula: S = P(OR1)(OR2)-Z wherein Z represents halogen, with an aminoalkyl mercaptan of the formula MetSLX1, X1 not being attached to the same carbon atom as the mercapto group. The examples describe the preparation of o:o1-diethyl S-b -diethylaminoethyl phosphorothiolothionate, o:o1 - diethyl S - 1 - di - n - propylaminoprop - 2 - yl phosphorothiolothionate, o:o1 - diethyl S - 1 - diethylamino - 3 - ethoxy - prop - 2 - yl phosphorothiolothionate, o:o1 - diethyl S - b - di-n - propylaminoethyl phosphorothiolothionate, o:o1 - diethyl S - 1 - diethylaminoprop - 2 - yl phosphorothiolothionate o:o1 - diethyl S - b -di - n - butylaminoethyl phosphorothiolothionate, o:o1 - diethyl S - 3 - diethylaminopropyl phosphorothiolothionate, o:o1 - diethyl S - b -piperidinoethyl phosphorothiolothionate, o:o1-di - n - propyl S - b - diethylaminoethyl phosphorothiolothionate, o:o1 - di - n - propyl S-b - piperidinoethyl phosphorothiolothionate, o - ethyl o1 - n - propyl S - b - diethylaminoethyl phosphorothiolothionate, o:o1 - diethyl S-[1 - di - n - propylamino - 3 - ethylthio] - prop-2 - yl phosphorothiolothionate and o:o1 - diisopropyl S - b - dimethylaminoethyl phosphorothiolothionate. 3 - Ethylthio - 1 - di - n - propylamino - propane - 2 - ol is prepared by condensing 1 - chloro - 3 - ethylthiopropan - 2 - ol with di - n-propylamine. 2 - Chloro - 1 - di - n - propylamino - 3 - ethylthiopropane is prepared by reacting thionyl chloride with 3-ethylthio-1-di-n-propylaminopropane-2-ol. Reference has been directed by the Comptroller to Specification 740,563.ALSO:A combined plant nutrient and pesticidal composition comprises a phosphorothiolothionic ester of the formula: S = P(OR1)(OR2)-S-LX wherein R1 and R2 are alkyl radicals, L is a saturated aliphatic hydrocarbon radical in which the carbon atoms may be interrupted by an oxygen atom, a sulphur atom or an N-Alkyl substituent, and X represents a secondary aliphatic or heterocyclic amino radical attached to L through the amine nitrogen atom, said nitrogen atom not being attached to the same carbon atom as the sulphur atom linking L with the phosphorus atom, together with a plant nutrient and, if desired, a solid or liquid carrier and/or an auxiliary agent. Specified plant nutrients are urea and magnesium sulphate. Specified carriers are water, non-phytocidal organic solvents, talc, kieselguhr, bentonite, other colloidal clays and powdered chalk. Specified auxiliary agents are spindle oil, glycerol, wool fat, sodium dinaphthylmethane disulphonate, sodium lauryl sulphate, glue and resin. Reference has been directed by the Comptroller to Specification 740,563 [Group VI].ALSO:A pesticidal composition comprises a phosphorothiolothianic ester of the formula S=P(OR1)(OR2)-S-LX, wherein R1 and R2 are alkyl radicals, L is a saturated aliphatic hydrocarbon radical n which the carbon atoms may be interrupted by an oxygen atom, a sulphur atom or an N-Alkyl substituent, and X represents a secondary aliphatic or heterocyclic amino radical attached to L through the amine nitrogen atom, said nitrogen atom not being attached to the same carbon atom as the sulphur atom linking L with the phosphorus atom, together with a solid or liquid carrier and, if desired, an auxiliary agent and/or a plant nutrient. Specified carriers are water, non-phytocidal organic solvents, talc, kieselguhr, bentonite, other colloidal clays and powdered chalk. Specified auxiliary agents are spindle oil, glycerol, wool fat, sodium dinaphthylmethane disulphonate, sodium lauryl sulphate, glue and resin. Specified plant nutrients are urea and magnesium sulphate. Reference has been directed by the Comptroller to Specification 740,563.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE537490D BE537490A (en) | 1954-08-10 | ||
| GB2321254A GB783281A (en) | 1954-08-10 | 1954-08-10 | New pesticidal basic esters of phosphorothiolothionic acid |
| ES0221370A ES221370A1 (en) | 1954-08-10 | 1955-04-23 | New pesticidal basic esters of phosphorothiolothionic acid |
| DEI10479A DE1062254B (en) | 1954-08-10 | 1955-07-28 | Process for the preparation of new, insecticidally effective, basic thiophosphoric acid esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2321254A GB783281A (en) | 1954-08-10 | 1954-08-10 | New pesticidal basic esters of phosphorothiolothionic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB783281A true GB783281A (en) | 1957-09-18 |
Family
ID=10191970
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2321254A Expired GB783281A (en) | 1954-08-10 | 1954-08-10 | New pesticidal basic esters of phosphorothiolothionic acid |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE537490A (en) |
| DE (1) | DE1062254B (en) |
| ES (1) | ES221370A1 (en) |
| GB (1) | GB783281A (en) |
-
0
- BE BE537490D patent/BE537490A/xx unknown
-
1954
- 1954-08-10 GB GB2321254A patent/GB783281A/en not_active Expired
-
1955
- 1955-04-23 ES ES0221370A patent/ES221370A1/en not_active Expired
- 1955-07-28 DE DEI10479A patent/DE1062254B/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BE537490A (en) | |
| ES221370A1 (en) | 1955-11-16 |
| DE1062254B (en) | 1959-07-30 |
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