DE2628992A1 - Beta-phenyl-4-piperidinone und -dihydropyridinone und verfahren zu deren herstellung - Google Patents
Beta-phenyl-4-piperidinone und -dihydropyridinone und verfahren zu deren herstellungInfo
- Publication number
- DE2628992A1 DE2628992A1 DE19762628992 DE2628992A DE2628992A1 DE 2628992 A1 DE2628992 A1 DE 2628992A1 DE 19762628992 DE19762628992 DE 19762628992 DE 2628992 A DE2628992 A DE 2628992A DE 2628992 A1 DE2628992 A1 DE 2628992A1
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- methyl
- pyridinone
- dihydro
- paragraphs
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 47
- 230000008569 process Effects 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 150
- -1 phenoxy, phenylthio Chemical group 0.000 claims description 76
- 239000000203 mixture Substances 0.000 claims description 49
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 239000004480 active ingredient Substances 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- 239000011737 fluorine Substances 0.000 claims description 21
- 150000002431 hydrogen Chemical group 0.000 claims description 21
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- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 230000002363 herbicidal effect Effects 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 13
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
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- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
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- HDDWJXJLZCWVBF-UHFFFAOYSA-N 1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]piperidin-4-one Chemical group C1N(C)CC(C=2C=CC=CC=2)C(=O)C1C1=CC=CC(C(F)(F)F)=C1 HDDWJXJLZCWVBF-UHFFFAOYSA-N 0.000 claims description 3
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- VRWBDTPZJOEALB-UHFFFAOYSA-N 1-methyl-3-(3-methylphenyl)-5-phenyl-2,3-dihydropyridin-4-one Chemical compound C=1N(C)CC(C=2C=C(C)C=CC=2)C(=O)C=1C1=CC=CC=C1 VRWBDTPZJOEALB-UHFFFAOYSA-N 0.000 claims description 2
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- AVSUIEDSKCPYKV-UHFFFAOYSA-N 5-(4-fluorophenyl)-1-methyl-3-[3-(trifluoromethyl)phenyl]-2,3-dihydropyridin-4-one Chemical compound C=1N(C)CC(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C=1C1=CC=C(F)C=C1 AVSUIEDSKCPYKV-UHFFFAOYSA-N 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 10
- OVVCXAPQRAUKRK-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-methyl-5-[3-(trifluoromethyl)phenyl]-2,3-dihydropyridin-4-one Chemical compound C=1N(C)CC(C=2C=CC(Cl)=CC=2)C(=O)C=1C1=CC=CC(C(F)(F)F)=C1 OVVCXAPQRAUKRK-UHFFFAOYSA-N 0.000 claims 2
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- 238000004458 analytical method Methods 0.000 description 19
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- 239000012280 lithium aluminium hydride Substances 0.000 description 16
- 150000005299 pyridinones Chemical class 0.000 description 15
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- 238000011835 investigation Methods 0.000 description 14
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- 244000062793 Sorghum vulgare Species 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 12
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 11
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- 238000012360 testing method Methods 0.000 description 11
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 238000004949 mass spectrometry Methods 0.000 description 8
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 8
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/68—One oxygen atom attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59309575A | 1975-07-03 | 1975-07-03 | |
| US05/685,409 US4065290A (en) | 1975-07-03 | 1976-05-20 | Herbicidal β-phenyl-4-piperidinones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2628992A1 true DE2628992A1 (de) | 1977-01-20 |
Family
ID=27081623
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762628992 Withdrawn DE2628992A1 (de) | 1975-07-03 | 1976-06-28 | Beta-phenyl-4-piperidinone und -dihydropyridinone und verfahren zu deren herstellung |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS527970A (enExample) |
| AU (1) | AU497882B2 (enExample) |
| BR (1) | BR7604362A (enExample) |
| CA (1) | CA1088543A (enExample) |
| CH (2) | CH624273A5 (enExample) |
| DE (1) | DE2628992A1 (enExample) |
| ES (1) | ES449530A1 (enExample) |
| FR (1) | FR2315851A1 (enExample) |
| GB (1) | GB1555966A (enExample) |
| GR (1) | GR62256B (enExample) |
| IE (1) | IE43851B1 (enExample) |
| IL (1) | IL49858A (enExample) |
| IT (1) | IT1065058B (enExample) |
| NL (1) | NL7607421A (enExample) |
| OA (1) | OA05373A (enExample) |
| PT (1) | PT65313B (enExample) |
| SU (2) | SU691060A3 (enExample) |
| TR (1) | TR18922A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2720612A1 (de) * | 1977-05-07 | 1978-11-16 | Basf Ag | 3,5-dimethyl-piperidin-4-one |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4808720A (en) * | 1986-06-09 | 1989-02-28 | Stauffer Chemical Company | Certain 3-benzoyl-4-oxolactams |
-
1976
- 1976-06-14 CA CA254,796A patent/CA1088543A/en not_active Expired
- 1976-06-15 GR GR51000A patent/GR62256B/el unknown
- 1976-06-15 IE IE1295/76A patent/IE43851B1/en unknown
- 1976-06-22 IL IL49858A patent/IL49858A/xx unknown
- 1976-06-28 GB GB26770/76A patent/GB1555966A/en not_active Expired
- 1976-06-28 DE DE19762628992 patent/DE2628992A1/de not_active Withdrawn
- 1976-07-01 OA OA55871A patent/OA05373A/xx unknown
- 1976-07-02 IT IT25001/76A patent/IT1065058B/it active
- 1976-07-02 SU SU762377702A patent/SU691060A3/ru active
- 1976-07-02 ES ES449530A patent/ES449530A1/es not_active Expired
- 1976-07-02 BR BR7604362A patent/BR7604362A/pt unknown
- 1976-07-02 CH CH851576A patent/CH624273A5/de not_active IP Right Cessation
- 1976-07-02 PT PT65313A patent/PT65313B/pt unknown
- 1976-07-02 AU AU15538/76A patent/AU497882B2/en not_active Expired
- 1976-07-02 TR TR18922A patent/TR18922A/xx unknown
- 1976-07-02 FR FR7620260A patent/FR2315851A1/fr active Granted
- 1976-07-03 JP JP51079407A patent/JPS527970A/ja active Pending
- 1976-07-05 NL NL7607421A patent/NL7607421A/xx not_active Application Discontinuation
-
1977
- 1977-02-17 SU SU772453148A patent/SU688126A3/ru active
-
1980
- 1980-04-25 CH CH322980A patent/CH624392A5/de not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2720612A1 (de) * | 1977-05-07 | 1978-11-16 | Basf Ag | 3,5-dimethyl-piperidin-4-one |
Also Published As
| Publication number | Publication date |
|---|---|
| IE43851B1 (en) | 1981-06-17 |
| OA05373A (fr) | 1981-02-28 |
| CH624273A5 (en) | 1981-07-31 |
| ES449530A1 (es) | 1977-12-01 |
| JPS527970A (en) | 1977-01-21 |
| BR7604362A (pt) | 1977-07-26 |
| AU497882B2 (en) | 1979-01-18 |
| CA1088543A (en) | 1980-10-28 |
| SU688126A3 (ru) | 1979-09-25 |
| IL49858A (en) | 1980-06-30 |
| GB1555966A (en) | 1979-11-14 |
| FR2315851A1 (fr) | 1977-01-28 |
| SU691060A3 (ru) | 1979-10-05 |
| NL7607421A (nl) | 1977-01-05 |
| AU1553876A (en) | 1978-01-05 |
| IT1065058B (it) | 1985-02-25 |
| PT65313B (en) | 1978-01-05 |
| IL49858A0 (en) | 1976-08-31 |
| PT65313A (en) | 1976-08-01 |
| IE43851L (en) | 1977-01-03 |
| FR2315851B1 (enExample) | 1978-05-05 |
| GR62256B (en) | 1979-03-19 |
| TR18922A (tr) | 1977-12-20 |
| CH624392A5 (en) | 1981-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: SPOTT, G., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 800 |
|
| 8141 | Disposal/no request for examination |