GB1396169A - Phosphoryloxy-pyrimidones processes for their prepration and pesticidal compositions incorporating them - Google Patents
Phosphoryloxy-pyrimidones processes for their prepration and pesticidal compositions incorporating themInfo
- Publication number
- GB1396169A GB1396169A GB4282572A GB4282572A GB1396169A GB 1396169 A GB1396169 A GB 1396169A GB 4282572 A GB4282572 A GB 4282572A GB 4282572 A GB4282572 A GB 4282572A GB 1396169 A GB1396169 A GB 1396169A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyrimidine
- hydroxy
- prepared
- formula
- reacting
- 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
- 230000000361 pesticidal effect Effects 0.000 title abstract 3
- 239000000203 mixture Substances 0.000 title abstract 2
- -1 Phosphoryloxy-pyrimidones Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical group BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Substances 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- UOFWYOLXWCWWMG-UHFFFAOYSA-N 1-O-ethyl 3-O-ethylsulfanyl propanedioate Chemical compound C(CC(=O)OSCC)(=O)OCC UOFWYOLXWCWWMG-UHFFFAOYSA-N 0.000 abstract 1
- NJBMZYSKLWQXLJ-UHFFFAOYSA-N 3,4-dihydro-2h-pyrrol-5-amine Chemical compound NC1=NCCC1 NJBMZYSKLWQXLJ-UHFFFAOYSA-N 0.000 abstract 1
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 230000000895 acaricidal effect Effects 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000002947 alkylene group 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
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- BYQFBFWERHXONI-UHFFFAOYSA-N diethyl 2-propan-2-ylpropanedioate Chemical compound CCOC(=O)C(C(C)C)C(=O)OCC BYQFBFWERHXONI-UHFFFAOYSA-N 0.000 abstract 1
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 1
- HAOKKJHTFUZWIM-UHFFFAOYSA-N pyridin-1-ium-2-amine;chloride Chemical compound Cl.NC1=CC=CC=N1 HAOKKJHTFUZWIM-UHFFFAOYSA-N 0.000 abstract 1
- 150000008318 pyrimidones Chemical class 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1396169 Pesticidal pyrimidone derivatives ROUSSEL UCLAF 15 Sept 1972 [16 Sept 1971] 42825/72 Headings C2P and C2C Novel compounds of Formula I where A is a C 3-5 alkylene chain in which one carbon atom may be replaced by sulphur or nitrogen, Y is hydrogen, halogen, alkyl, cyano or alkylthio, X is oxygen or sulphur, R<SP>1</SP> is alkyl and R<SP>2</SP> is alkyl, alkoxy, alkoxyalkoxy or -NR<SP>3</SP>(R<SP>3</SP>) where each R<SP>3</SP> is hydrogen or alkyl, may be prepared by reacting a compound of Formula II optionally in the presence of a base, with a compound of Formula III where Hal is chlorine or bromine. Compounds of Formula I in which Y is hydrogen, R<SP>1</SP> is alkyl and R<SP>2</SP> is alkoxy may also be prepared by reacting a compound of Formula IV with an appropriate trialkyl phosphite. Starting materials are prepared as follows in examples: 2-hydroxy-6,7,8,9-tetrahydro-pyrido- [1,2a] - pyrimidine - 4 - one and 2 - hydroxy - 3- ethylthio - [6H] - 7,8 - dihydro - pyrrolo - [1,2a]- pyrimidine-4-one are prepared by reacting iminopyridine hydrochloride with ethyl malonate in the presence of sodium and imino pyrrolidine with ethyl ethylthio malonate respectively; 2 - hydroxy - 3 - bromo - [6H] - 7, 8,9,10 - tetrahydro - azepino - [1,2a) - pyrimidine- 4-one is prepared by reacting the corresponding compound which is 3-unsubstituted with N- bromosuccinimide; 2 - hydroxy - 3 - isopropyl- [6H] - 7,8,9,10 - tetrahydro - azepino - [1,2a]- pyrimidine-4-one is prepared by reacting caprolactamidine sulphate with ethyl isopropyl malonate; and 2-hydroxy-[6H]-7,8-dihydropyrrolo - [1,2a] - pyrimidine - 4 - one and 2- hydroxy - 3 - methyl - [6H] - 7,8 - dihydropyrrolo - [1,2a] - pyrimidine - 4 - one are converted to their sodium salts by reaction with sodium methylate. The compounds of Formula I have insecticidal and acaricidal properties and may be used as the active ingredients in conventional pesticidal compositions.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7133434A FR2152469B1 (en) | 1971-09-16 | 1971-09-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1396169A true GB1396169A (en) | 1975-06-04 |
Family
ID=9083063
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4282572A Expired GB1396169A (en) | 1971-09-16 | 1972-09-15 | Phosphoryloxy-pyrimidones processes for their prepration and pesticidal compositions incorporating them |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3857838A (en) |
| JP (1) | JPS4836189A (en) |
| AU (1) | AU466846B2 (en) |
| BE (1) | BE788828A (en) |
| CA (1) | CA981671A (en) |
| DE (1) | DE2245386A1 (en) |
| ES (1) | ES406728A1 (en) |
| FR (1) | FR2152469B1 (en) |
| GB (1) | GB1396169A (en) |
| IL (1) | IL40323A (en) |
| IT (1) | IT965384B (en) |
| NL (1) | NL7212526A (en) |
| ZA (1) | ZA726212B (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2198697B1 (en) * | 1972-09-11 | 1975-09-12 | Roussel Uclaf | |
| US4000267A (en) * | 1972-09-11 | 1976-12-28 | Roussel-Uclaf | Insecticidal and acaricidal compositions employing pyrido[1,2a]pyrimidinone thiophosphates |
| US3973009A (en) * | 1974-05-06 | 1976-08-03 | Stauffer Chemical Company | Insecticidal and miticidal method |
| DE2703712A1 (en) * | 1977-01-29 | 1978-08-03 | Bayer Ag | SUBSTITUTED PYRIMIDINONE ANGLE CLAMP ON (DI) -THIO ANGLE CLAMP ON -PHOSPHORUS- (PHOSPHONE) -ACIDESTER OR. -ESTERAMIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES, ACARICIDES AND NEMATICIDES |
| US4472389A (en) * | 1981-12-10 | 1984-09-18 | Uniroyal, Inc. | Substituted pyrimidinyl organophosphorus insecticides |
| US4395551A (en) * | 1981-12-10 | 1983-07-26 | Uniroyal, Inc. | Pyridopyrimidinone compounds |
| US4634690A (en) * | 1981-12-10 | 1987-01-06 | Uniroyal Chemical Company, Inc. | Substituted pyrimidinyl organophosphorus insecticides |
| DE3930130A1 (en) * | 1989-09-09 | 1991-03-21 | Boehringer Mannheim Gmbh | NEW AMIDINE GROUP-CONTAINING DIPHOSPHONIC ACID DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS |
| JP2000026465A (en) * | 1998-07-14 | 2000-01-25 | Fuji Photo Film Co Ltd | Pyrrolo[1,2-a]pyrimidine and thermally sensitive recording material using the same |
| AU2018220892B2 (en) * | 2017-02-15 | 2023-04-13 | Zuru (Singapore) Pte. Ltd. | Apparatus for housing and revealing a plurality of children's toys |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1239695B (en) * | 1964-12-24 | 1967-05-03 | Bayer Ag | Process for the preparation of phosphorus, phosphonic, thionophosphorus or thionophosphonic acid esters |
-
0
- BE BE788828D patent/BE788828A/en unknown
-
1971
- 1971-09-16 FR FR7133434A patent/FR2152469B1/fr not_active Expired
-
1972
- 1972-09-07 IL IL40323A patent/IL40323A/en unknown
- 1972-09-12 US US00288393A patent/US3857838A/en not_active Expired - Lifetime
- 1972-09-14 JP JP47091865A patent/JPS4836189A/ja active Pending
- 1972-09-15 ES ES406728A patent/ES406728A1/en not_active Expired
- 1972-09-15 NL NL7212526A patent/NL7212526A/xx not_active Application Discontinuation
- 1972-09-15 CA CA151,877A patent/CA981671A/en not_active Expired
- 1972-09-15 AU AU46740/72A patent/AU466846B2/en not_active Expired
- 1972-09-15 IT IT52790/72A patent/IT965384B/en active
- 1972-09-15 DE DE2245386A patent/DE2245386A1/en active Pending
- 1972-09-15 GB GB4282572A patent/GB1396169A/en not_active Expired
-
1973
- 1973-09-12 ZA ZA726212A patent/ZA726212B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES406728A1 (en) | 1975-10-01 |
| FR2152469A1 (en) | 1973-04-27 |
| DE2245386A1 (en) | 1973-03-22 |
| US3857838A (en) | 1974-12-31 |
| IL40323A0 (en) | 1972-11-28 |
| IT965384B (en) | 1974-01-31 |
| AU4674072A (en) | 1974-03-21 |
| AU466846B2 (en) | 1975-11-13 |
| CA981671A (en) | 1976-01-13 |
| NL7212526A (en) | 1973-03-20 |
| BE788828A (en) | 1973-03-14 |
| FR2152469B1 (en) | 1974-03-29 |
| IL40323A (en) | 1976-03-31 |
| JPS4836189A (en) | 1973-05-28 |
| ZA726212B (en) | 1973-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |