GB1391354A - O-pyrazolopyrimidine-thiono-phosphoric-phosphonic or phosphinic- acid esters or ester-amides process for their production and their use as insecticides or acaricides - Google Patents
O-pyrazolopyrimidine-thiono-phosphoric-phosphonic or phosphinic- acid esters or ester-amides process for their production and their use as insecticides or acaricidesInfo
- Publication number
- GB1391354A GB1391354A GB2951872A GB2951872A GB1391354A GB 1391354 A GB1391354 A GB 1391354A GB 2951872 A GB2951872 A GB 2951872A GB 2951872 A GB2951872 A GB 2951872A GB 1391354 A GB1391354 A GB 1391354A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hal
- halogen
- formula iii
- thiono
- pyrazolopyrimidine
- 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
- 230000000895 acaricidal effect Effects 0.000 title abstract 2
- 239000000642 acaricide Substances 0.000 title 1
- 239000002917 insecticide Substances 0.000 title 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- -1 isopropoxy, methoxy Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 230000000361 pesticidal effect Effects 0.000 abstract 2
- XHTYQFMRBQUCPX-UHFFFAOYSA-N 1,1,3,3-tetramethoxypropane Chemical compound COC(OC)CC(OC)OC XHTYQFMRBQUCPX-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
- 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
- 239000002253 acid Substances 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 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
- OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical class C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 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
- 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)
Abstract
1391354 Pesticidal phosphorus-containing pyrazolo-pyrimidine derivatives BAYER AG 23 June 1972 [24 June 1971] 29518/72 Addition to 1049960 Headings C2P and C2C The invention comprises particular compounds falling within the general formula where R 1 is methyl, isopropoxy, methoxy or ethoxy, R 2 is methyl, ethyl, phenyl, methoxy, ethoxy, dimethylamino or isopropylamino, R 3 is hydrogen, chlorine or bromine, X is oxygen or sulphur and Hal is halogen which may be prepared by reacting a compound of Formula II R 1 R 2 -P(X)-Hal where Hal is halogen with a compound of Formula III in the presence of an acid acceptor or in the form of an alkali metal, alkaline earth metal or ammonium salt. The starting materials of Formula III in which R 3 is hydrogen may be prepared by reacting 3-aminopyrazolone with 1,1,3,3-tetramethoxypropane and concentrated HC1, and this material may be halogenated to give the compounds of Formula III in which R 3 is halogen. The compounds of the invention 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 |
|---|---|---|---|
| DE2131298A DE2131298C3 (en) | 1971-06-24 | 1971-06-24 | O-pyrazolopyrimidine (thiono) phosphorus (phosphon, phosphine) acid esters or ester amides, processes for their preparation and agents containing them as insecticides and alkaricides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1391354A true GB1391354A (en) | 1975-04-23 |
Family
ID=5811637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2951872A Expired GB1391354A (en) | 1971-06-24 | 1972-06-23 | O-pyrazolopyrimidine-thiono-phosphoric-phosphonic or phosphinic- acid esters or ester-amides process for their production and their use as insecticides or acaricides |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3840541A (en) |
| AT (1) | AT308143B (en) |
| AU (1) | AU470168B2 (en) |
| BE (1) | BE785265A (en) |
| BR (1) | BR7204068D0 (en) |
| CH (1) | CH571529A5 (en) |
| CS (1) | CS175430B2 (en) |
| DD (1) | DD101167A5 (en) |
| DE (1) | DE2131298C3 (en) |
| DK (1) | DK133008C (en) |
| EG (1) | EG10481A (en) |
| ES (1) | ES404213A1 (en) |
| FR (1) | FR2143450B1 (en) |
| GB (1) | GB1391354A (en) |
| HU (1) | HU163999B (en) |
| IL (1) | IL39728A (en) |
| IT (1) | IT961237B (en) |
| NL (1) | NL7208683A (en) |
| ZA (1) | ZA724332B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3948926A (en) * | 1971-12-30 | 1976-04-06 | Saburo Kano | O,O-Diethyl-2-(5-ethyl-6-bromothiazolo[3,2-b]-s-triazolyl)thionophosphate |
| DE2544938C2 (en) * | 1975-10-07 | 1983-12-29 | Bayer Ag, 5090 Leverkusen | O-pyrazolopyrimidine (thiono) phosphorus (phosphonic) acid esters or ester amides, process for their preparation and their use for combating insects, mites and nematodes |
| DE2545881C2 (en) * | 1975-10-14 | 1985-08-29 | Bayer Ag, 5090 Leverkusen | 0-Pyrazolopyrimidinthionothiolphosphorsäureester, process for their preparation and their use for combating insects, mites and nematodes |
| CN1865258A (en) | 2001-08-15 | 2006-11-22 | 纳幕尔杜邦公司 | Ortho-substituted aryl amides for controlling invertebrate pests |
-
1971
- 1971-06-24 DE DE2131298A patent/DE2131298C3/en not_active Expired
-
1972
- 1972-06-06 CS CS3905A patent/CS175430B2/cs unknown
- 1972-06-08 EG EG241/72A patent/EG10481A/en active
- 1972-06-15 US US00263075A patent/US3840541A/en not_active Expired - Lifetime
- 1972-06-21 IL IL39728A patent/IL39728A/en unknown
- 1972-06-21 AU AU43714/72A patent/AU470168B2/en not_active Expired
- 1972-06-22 BR BR4068/72A patent/BR7204068D0/en unknown
- 1972-06-22 DD DD163948A patent/DD101167A5/xx unknown
- 1972-06-22 IT IT26063/72A patent/IT961237B/en active
- 1972-06-22 BE BE785265A patent/BE785265A/en unknown
- 1972-06-22 AT AT538272A patent/AT308143B/en not_active IP Right Cessation
- 1972-06-22 HU HUBA2762A patent/HU163999B/hu unknown
- 1972-06-22 CH CH936472A patent/CH571529A5/xx not_active IP Right Cessation
- 1972-06-23 ES ES404213A patent/ES404213A1/en not_active Expired
- 1972-06-23 DK DK317172A patent/DK133008C/en active
- 1972-06-23 ZA ZA724332A patent/ZA724332B/en unknown
- 1972-06-23 FR FR7222916A patent/FR2143450B1/fr not_active Expired
- 1972-06-23 GB GB2951872A patent/GB1391354A/en not_active Expired
- 1972-06-23 NL NL7208683A patent/NL7208683A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| BE785265A (en) | 1972-12-22 |
| IL39728A0 (en) | 1972-08-30 |
| ZA724332B (en) | 1973-03-28 |
| EG10481A (en) | 1976-07-31 |
| ES404213A1 (en) | 1975-05-16 |
| DK133008B (en) | 1976-03-08 |
| US3840541A (en) | 1974-10-08 |
| IT961237B (en) | 1973-12-10 |
| DE2131298C3 (en) | 1980-02-14 |
| DD101167A5 (en) | 1973-10-20 |
| HU163999B (en) | 1973-12-28 |
| BR7204068D0 (en) | 1973-05-03 |
| FR2143450A1 (en) | 1973-02-02 |
| AT308143B (en) | 1973-06-25 |
| AU4371472A (en) | 1974-01-03 |
| FR2143450B1 (en) | 1977-12-23 |
| CH571529A5 (en) | 1976-01-15 |
| CS175430B2 (en) | 1977-05-31 |
| NL7208683A (en) | 1972-12-28 |
| AU470168B2 (en) | 1976-03-04 |
| DE2131298B2 (en) | 1979-06-21 |
| DK133008C (en) | 1976-08-09 |
| IL39728A (en) | 1975-10-15 |
| DE2131298A1 (en) | 1972-12-28 |
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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 |