GB952294A - Phosphorus-containing hydroquinone and quinone derivatives - Google Patents
Phosphorus-containing hydroquinone and quinone derivativesInfo
- Publication number
- GB952294A GB952294A GB2418862A GB2418862A GB952294A GB 952294 A GB952294 A GB 952294A GB 2418862 A GB2418862 A GB 2418862A GB 2418862 A GB2418862 A GB 2418862A GB 952294 A GB952294 A GB 952294A
- Authority
- GB
- United Kingdom
- Prior art keywords
- quinone
- alkyl
- hydrogen
- alkylamino
- derivative
- 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
- 150000004059 quinone derivatives Chemical class 0.000 title abstract 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 title abstract 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title 1
- 229910052698 phosphorus Inorganic materials 0.000 title 1
- 239000011574 phosphorus Substances 0.000 title 1
- 125000005843 halogen group Chemical group 0.000 abstract 7
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 abstract 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 4
- 125000004122 cyclic group Chemical group 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 abstract 3
- 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 239000003085 diluting agent Substances 0.000 abstract 3
- 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
- 241000607479 Yersinia pestis Species 0.000 abstract 2
- 238000007259 addition reaction Methods 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 abstract 2
- 125000004104 aryloxy group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 2
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 abstract 2
- 239000003814 drug Substances 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- CZGGKXNYNPJFAX-UHFFFAOYSA-N Dimethyldithiophosphate Chemical compound COP(S)(=S)OC CZGGKXNYNPJFAX-UHFFFAOYSA-N 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 238000007865 diluting Methods 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- 229920000151 polyglycol Polymers 0.000 abstract 1
- 239000010695 polyglycol Substances 0.000 abstract 1
- IHSLHAZEJBXKMN-UHFFFAOYSA-L potassium nitrosodisulfonate Chemical compound [K+].[K+].[O-]S(=O)(=O)N([O])S([O-])(=O)=O IHSLHAZEJBXKMN-UHFFFAOYSA-L 0.000 abstract 1
- 150000004053 quinones Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 150000003580 thiophosphoric acid esters Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/60—Quinoline or hydrogenated quinoline ring systems
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises thiophosphoric acid esters of the general formula: <FORM:0952294/C2/1> wherein A is an aromatic or quinoid ring system, Alkyl is an alkyl radical containing up to 4 carbon atoms, X is a hydroxyl group in the case of an aromatic system or an oxygen atom in the case of a quinoid system and R1, R2 and R3 are hydrogen or halogen atoms or alkyl radicals containing up to 4 carbon atoms which may be substituted by halogen atoms, or are alkoxy, aryloxy, amino, alkylamino, dialkylamino, saturated heterocyclic amino, alkylcarbonylamino, alkylcarbonyl alkylamino, alkoxycarbonylamino or alkoxycarbonylalkylamino radicals or another SP(S)(OAlkyl)2 group or R2 and R3 may be linked together to form a saturated or unsaturated cyclic residue which may be interrupted by a hetero atom. They may be obtained by reacting a quinone of the general formula: <FORM:0952294/C2/2> wherein Y is a hydrogen or halogen atom and R1, R2 and R3 are as defined above with an appropriate thionothiolphosphoric acid O,O-dialkyl ester or with a salt thereof when Y is a halogen atom and, if desired, subsequently oxidising the hydroquinone derivative, when obtained, to form the quinone derivative. The reaction can be carried out in the presence of an organic solvent or diluent and generally proceeds at room temperature. Suitable solvents are methanol, ethanol, acetone, methyl ethyl ketone and benzene. When Y in the formula is hydrogen the reaction is an addition reaction and the product is a hydroquinone derivative although some quinone starting materials yield quinhydrones as products. The hydroquinones and quinhydrones can be oxidised to the corresponding quinone derivatives, specified oxidising agents being p-benzoquinone, Fremy's salt and lead dioxide. The oxidation is preferably carried out in a solvent or diluent at room temperature, with cooling, or at a slightly elevated temperature. When Y is halogen the reaction will either take place with the splitting off of hydrogen halide to form a quinone derivative or, in certain cases and provided the quinone nucleus contains at least one free position, an addition reaction takes place, thus O,O-dimethyldithiophosphate reacts with 2,5-dichloro-benzoquinone-(1, 4) by addition to form a hydroquinone derivative. The products are useful as intermediates for pharmaceuticals, as pest control agents and as ingredients of veterinary medicines (see Division A5).ALSO:A pest control or veterinary composition comprises a solid or liquid carrier, or diluent and a hydroquinone or quinone derivative of the general formula:- <FORM:0952294/A5-A6/1> wherein A is an aromatic or quinoid ring system, alkyl is a C1-C4 alkyl radical, X is a hydroxyl group in the case of an aromatic system or an oxygen atom in the case of a quinoid system and R1, R2 and R3 are hydrogen, or halogen atoms or C1-C4 alkyl radicals which may be substituted by halogen atoms, or are alkoxy, aryloxy, amino, alkylamino, dialkylamino, saturated heterocyclic amino, alkylcarbonylamino, alkylcarbonyl alkylamino, alkoxycarbonylamino or alkoxycarbonylalkylamino radicals or another SP(S)(OAlkyl)2 group wherein alkyl is a C1-C4 alkyl group, or R2 and R3 may be linked together to form a saturated or unsaturated cyclic residue which may be interrupted by a hetero atom. A typical pesticidal composition is obtained by mixing the compound:- <FORM:0952294/A5-A6/2> with dimethyl formamide, adding a benzyl hydroxydiphenyl polyglycol ether as emulsifier and then diluting with water.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF34310A DE1149366B (en) | 1961-06-30 | 1961-06-30 | Process for the preparation of O, O-dialkyl-S-phenylthionothiolphosphoric acid esters |
DEF34648A DE1167838B (en) | 1961-06-30 | 1961-08-09 | Process for the preparation of O, O-dialkyl-S-thionothiolphosphoric acid esters of quinones or halohydroquinones |
Publications (1)
Publication Number | Publication Date |
---|---|
GB952294A true GB952294A (en) | 1964-03-11 |
Family
ID=25975034
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2418862A Expired GB952294A (en) | 1961-06-30 | 1962-06-22 | Phosphorus-containing hydroquinone and quinone derivatives |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE619334A (en) |
DE (1) | DE1167838B (en) |
GB (1) | GB952294A (en) |
NL (1) | NL280370A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994010269A1 (en) * | 1992-11-02 | 1994-05-11 | Exxon Chemical Limited | Novel antiwear-antioxidant additives for lubricating oils |
-
0
- NL NL280370D patent/NL280370A/xx unknown
-
1961
- 1961-08-09 DE DEF34648A patent/DE1167838B/en active Pending
-
1962
- 1962-06-22 GB GB2418862A patent/GB952294A/en not_active Expired
- 1962-06-25 BE BE619334A patent/BE619334A/en unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994010269A1 (en) * | 1992-11-02 | 1994-05-11 | Exxon Chemical Limited | Novel antiwear-antioxidant additives for lubricating oils |
Also Published As
Publication number | Publication date |
---|---|
DE1167838B (en) | 1964-04-16 |
NL280370A (en) | |
BE619334A (en) | 1962-12-27 |
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