GB1436754A - Phosphoric and thionophosphoric acid esters and esteramides - Google Patents
Phosphoric and thionophosphoric acid esters and esteramidesInfo
- Publication number
- GB1436754A GB1436754A GB2332373A GB2332373A GB1436754A GB 1436754 A GB1436754 A GB 1436754A GB 2332373 A GB2332373 A GB 2332373A GB 2332373 A GB2332373 A GB 2332373A GB 1436754 A GB1436754 A GB 1436754A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- formula
- alkylthio
- alkoxy
- hydrogen
- 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 2
- 150000002148 esters Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 6
- 125000003545 alkoxy group Chemical group 0.000 abstract 5
- 125000004414 alkyl thio group Chemical group 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000001768 cations Chemical class 0.000 abstract 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- -1 2 - substituted - 4,6 - dihydroxypyrimidine Chemical class 0.000 abstract 1
- SYFHLNPUIWQMTB-UHFFFAOYSA-N 6-chloro-2-propan-2-yl-1h-pyrimidin-4-one Chemical compound CC(C)C1=NC(=O)C=C(Cl)N1 SYFHLNPUIWQMTB-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 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 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 abstract 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 abstract 1
- 150000003230 pyrimidines Chemical class 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
1436754 Preparation of phosphorus-containing pyrimidine derivatives; hydroxy pyrimidines SANDOZ Ltd 16 May 1973 23323/73 Headings C2P and C2C Compounds of Formula I where R 1 is C 1-6 alkyl, R 2 is hydrogen, C 1-6 alkyl or C 2-6 alkenyl, R 3 is C 1-6 alkyl, alkoxy or alkylthio, R 4 is C 1-6 alkyl, alkoxy or alkylthio, amino, mono- or di-(C 1-6 alkyl)amino or an N-attached 5- or 6-membered nitrogen-containing heterocycle, R 5 is C 1-6 alkoxy or alkylthio; amino, mono- or di-(C 1-6 alkyl)amino or an N-attached 5- or 6-membered nitrogen-containing heterocycle and Y is oxygen or sulphur with the proviso that when R 5 is substituted or unsubstituted amino, then at least one of R 3 and R 4 is other than alkyl and/or R 2 is other than hydrogen and alkyl, which compounds have pesticidal properties, are prepared by reacting a compound of Formula II where M 1 is hydrogen or a metal cation with a compound of Formula III where Hal is chlorine or bromine and reacting the resulting compound with a compound of Formula IV where M 2 is hydrogen, or, when R 5 is alkoxy or alkylthio, a metal cation. When M 1 or M 2 is hydrogen the reaction is preferably effected in the presence of an acid acceptor. Compounds of Formula I in which R 4 is C 1-6 alkoxy or alkylthio are claimed per se. In examples, starting materials of Formula II are prepared as follows:- :- 2-isopropyl-4- (methoxy or ethoxy) - 6 - hydroxypyrimidine by reacting 2 - isopropyl - 4 - chloro - 6- hydroxypyrimidine with sodium and methanol or ethanol; and 2-(diethylamino, dimethylamino or di-n-propylamino)-4-(methoxy or ethoxy) - 6 - hydroxypyrimidine by reacting the corresponding 2 - substituted - 4,6 - dihydroxypyrimidine with dimethyl or diethyl sulphate. Reference has been directed by the Comptroller to Specifications 1,019,227; 1,129,563; 1,129,797; 1,203,026; 1,204,552; 1,205,000; 1,313,903 and 1,387,661.
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2332373A GB1436754A (en) | 1973-05-16 | 1973-05-16 | Phosphoric and thionophosphoric acid esters and esteramides |
| ZA00741376A ZA741376B (en) | 1973-03-23 | 1974-03-01 | Improvements in or relating to organic compounds |
| DE2412903A DE2412903A1 (en) | 1973-03-23 | 1974-03-18 | PROCESS FOR THE PRODUCTION OF PHOSPHORIC ACID ESTERS |
| NL7403656A NL7403656A (en) | 1973-03-23 | 1974-03-19 | |
| DD177354A DD113916A5 (en) | 1973-03-23 | 1974-03-21 | |
| BR2208/74A BR7402208D0 (en) | 1973-03-23 | 1974-03-21 | PROCESS FOR THE PREPARATION OF PHOSPHORIC ACID ESTERS |
| ES424481A ES424481A1 (en) | 1973-03-23 | 1974-03-21 | PROCEDURE FOR THE PRODUCTION OF PHOSPHO-RICH AND THIONOPHOSPHORIC ACID ESTERS. |
| FR7409667A FR2222382A1 (en) | 1973-03-23 | 1974-03-21 | 6-Pyrimidyl phosphate derivs prepn - from 6-hydroxy cpd in two stages, used as insecticides and acaricides |
| JP49033082A JPS5024281A (en) | 1973-03-23 | 1974-03-22 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2332373A GB1436754A (en) | 1973-05-16 | 1973-05-16 | Phosphoric and thionophosphoric acid esters and esteramides |
| ZA00741376A ZA741376B (en) | 1973-03-23 | 1974-03-01 | Improvements in or relating to organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1436754A true GB1436754A (en) | 1976-05-26 |
Family
ID=26256448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2332373A Expired GB1436754A (en) | 1973-03-23 | 1973-05-16 | Phosphoric and thionophosphoric acid esters and esteramides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1436754A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4308258A (en) | 1979-02-05 | 1981-12-29 | Sumitomo Chemical Company, Limited | Pyrimidin-4-yl-phosphorus esters and insecticidal, acaricidal or nematocidal compositions and methods using them |
-
1973
- 1973-05-16 GB GB2332373A patent/GB1436754A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4308258A (en) | 1979-02-05 | 1981-12-29 | Sumitomo Chemical Company, Limited | Pyrimidin-4-yl-phosphorus esters and insecticidal, acaricidal or nematocidal compositions and methods using them |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1133766A (en) | Novel acetals and a process for the manufacture and conversion thereof | |
| ES429366A1 (en) | 2,4,5,6-Tetrasubstituted pyrimidines and salts thereof | |
| KR830002757A (en) | Process for preparing pyrimidine compound | |
| ES8507507A1 (en) | Substituted 2-mercapto-imidazoles and their preparation and use. | |
| GB1459682A (en) | Bis-triazinyl-amino stilbene derivatives | |
| GB1425675A (en) | 3-hydroxy-benzyl-oxaziazolone and -thiadiazolone derivatives | |
| ES383564A1 (en) | Heterocyclic ethers of piperazine n alkanols | |
| GB1471193A (en) | Bis-triazinylamino-stilbene derivatives | |
| GB1501935A (en) | 5-nitropyrimidine derivatives and their use for influencing plant growth | |
| GB1436754A (en) | Phosphoric and thionophosphoric acid esters and esteramides | |
| ES405982A1 (en) | Aza-benzimidazoles | |
| GB1187680A (en) | New Heterocyclic Substituted Piperazines | |
| GB1396169A (en) | Phosphoryloxy-pyrimidones processes for their prepration and pesticidal compositions incorporating them | |
| ES437150A1 (en) | Hydroxyhexyl-alkylxanthines and pharmaceutical compositions containing hydroxyhexyl-alkylxanthines | |
| GB1234845A (en) | Phosphoric, phosphonic, thionophosphonic and thionophosphoric acid esters | |
| GB1152883A (en) | 4,5-Polymethylene-Pyrimidine Derivatives | |
| GB1492770A (en) | 1,3,5-triazine derivatives | |
| GB1466177A (en) | 4-hydroxy-pyrimidine derivatives | |
| ES345283A1 (en) | 2-(2-arylhydrazino)-2-imidazolines | |
| GB1419237A (en) | Substituted pyrimidinyl phosphoric and thiophosphoric esters having insecticidal properties | |
| ES407730A1 (en) | Pyrimidones | |
| AU569152B2 (en) | Enkephalinase inhibitors | |
| GB1331670A (en) | Quaternised benzofuranylbenzimadzoles | |
| ES392388A1 (en) | PROCEDURE FOR THE PREPARATION OF TETRAHYDROPYRIDINE DERIVATIVES. | |
| GB1343022A (en) | Phosphorus-containing guanamines |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |