GB1364137A - 1,3,4-oxadiazolone derivatives - Google Patents
1,3,4-oxadiazolone derivativesInfo
- Publication number
- GB1364137A GB1364137A GB4133072A GB4133072A GB1364137A GB 1364137 A GB1364137 A GB 1364137A GB 4133072 A GB4133072 A GB 4133072A GB 4133072 A GB4133072 A GB 4133072A GB 1364137 A GB1364137 A GB 1364137A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- carbon atoms
- compound
- prepared
- alkyl
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C243/28—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of a saturated carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Paints Or Removers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
1364137 1,3,4-oxadiazolone derivatives RHONE-POULENC SA 6 Sept 1972 [9 Sept 1971 5 July 1972] 41330/72 Heading C2C The invention comprises oxadiazolone derivatives of general formula wherein R represents an alkyl radical containing 1 to 4 carbon atoms or a cycloalkyl radical containing 3 to 6 carbon atoms, R 1 and R 2 are the same or different and each represents a hydrogen or halogen atom or an alkyl radical containing 1 to 4 carbon atoms, R 3 represents a hydrogen atom, or an alkyl or alkoxy radical each containing 1 to 4 carbon atoms, and R 4 represents a carboxy radical, an alkoxycarbonyl radical in which alkyl moiety contains 1 to 4 carbon atoms, a hydromethyl radical, an alkoxymethyl radical in which the alkyl moiety contains 1 to 4 carbon atoms, or a carbamoyl group -CONR 5 R 6 , in which R 5 represents a hydrogen atom or an alkyl radical containing 1 to 4 carbon atoms, an alkenyl radical containing 2 to 4 carbon atoms or an alkoxy radical containing 1 to 4 carbon atoms, and R 6 represents a hydrogen atom or an alkyl radical containing 1 to 4 carbon atoms or an alkenyl radical containing 2 to 4 carbon atoms. Compounds of Formula I where R 4 represents carboxy, alkoxycarbonyl or alkoxymethyl may be prepared by reacting a compound of Formula II where X is a halogen atom, and R 7 is carboxy optionally salified by an alkali metal atom, or alkoxycarbonyl or alkoxymethyl in which the alkyl moiety contains 1 to 4 carbon atoms, with an oxadiazolone derivative of Formula III Compounds of Formula I where R 4 is carboxy may also be prepared by acid or alkaline hydrolysis of a compound of Formula I where R 4 is alkoxycarbonyl in which the alkyl moiety contains 1 to 4 carbon atoms. Compounds of Formula I where R 4 is -CONR 5 R 6 may be prepared by reacting a compound of Formula IV with an acid halide of Formula V where X 1 is a halogen atom. The acid halides of Formula V may be obtained by reacting thionyl chloride with a compound of Formula I where R 4 is carboxy. Compounds of Formula I where R 4 is hydroxymethyl may be prepared by reduction of a compound of Formula I where R 4 is alkoxycarbonyl in which the alkyl moiety contains 1 to 4 carbon atoms. The oxadiazolone derivatives of Formula III may be prepared by reacting phosgene with a hydrazide of Formula VI or by hydrolysis in an acid medium of a compound of Formula VII where R 8 is a C 1 to C 4 alkyl radical. The hydrazide of Formula VII may be prepared by diazotization of the corresponding amino compound followed by reduction of the diazonium salt with stannous chloride, the amino compound having first been prepared by reduction of the nitro compound. The compounds of Formula I are used in herbicidal compositions.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7132587A FR2162692A5 (en) | 1971-09-09 | 1971-09-09 | |
| FR7224327A FR2205068A6 (en) | 1972-07-05 | 1972-07-05 | 3-(substd phenyl)-oxadiazol-2-ones - with herbicidal activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1364137A true GB1364137A (en) | 1974-08-21 |
Family
ID=26216605
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4133072A Expired GB1364137A (en) | 1971-09-09 | 1972-09-06 | 1,3,4-oxadiazolone derivatives |
Country Status (20)
| Country | Link |
|---|---|
| JP (2) | JPS5248987B2 (en) |
| AR (1) | AR194500A1 (en) |
| AT (3) | AT317887B (en) |
| AU (1) | AU463690B2 (en) |
| BE (1) | BE788612A (en) |
| CA (1) | CA986122A (en) |
| CH (3) | CH561014A5 (en) |
| DE (1) | DE2244237A1 (en) |
| DK (1) | DK131676C (en) |
| EG (1) | EG10717A (en) |
| ES (4) | ES406548A1 (en) |
| GB (1) | GB1364137A (en) |
| HU (1) | HU165428B (en) |
| IL (1) | IL40321A (en) |
| IT (1) | IT967312B (en) |
| NL (1) | NL7211949A (en) |
| OA (1) | OA04166A (en) |
| RO (1) | RO62265A (en) |
| SE (1) | SE376234B (en) |
| SU (1) | SU496735A3 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0354622A1 (en) * | 1988-08-11 | 1990-02-14 | Shell Internationale Researchmaatschappij B.V. | Oxadiazolone herbicides |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2222378B1 (en) * | 1973-03-22 | 1976-11-05 | Rhone Poulenc Ind | |
| JPS5218302A (en) * | 1975-08-01 | 1977-02-10 | Fuji Photo Film Co Ltd | Magnetic sheet recording/playing method |
| JPS5228697A (en) * | 1975-08-29 | 1977-03-03 | Hitachi Maxell Ltd | Production method of magnetic powder |
| JPS60171887A (en) * | 1984-02-15 | 1985-09-05 | Matsushita Electric Ind Co Ltd | Solid-state color image pickup device |
| JPS6224896U (en) * | 1985-07-30 | 1987-02-16 | ||
| JPS6356078U (en) * | 1986-09-30 | 1988-04-14 | ||
| JP3135741B2 (en) * | 1993-05-07 | 2001-02-19 | 富士写真フイルム株式会社 | Abrasive body |
| DE19822316A1 (en) * | 1998-05-19 | 1999-11-25 | Clariant Gmbh | Process for the preparation of arylhydrazines |
| BR112018017117B1 (en) * | 2016-03-15 | 2021-11-16 | Shionogi & Co., Ltd. | PRODUCTION METHOD FOR PHENOXYETHANOL DERIVATIVES |
-
0
- BE BE788612D patent/BE788612A/en unknown
-
1972
- 1972-08-29 RO RO72055A patent/RO62265A/ro unknown
- 1972-09-01 OA OA54680A patent/OA04166A/en unknown
- 1972-09-01 NL NL7211949A patent/NL7211949A/xx not_active Application Discontinuation
- 1972-09-06 GB GB4133072A patent/GB1364137A/en not_active Expired
- 1972-09-06 AU AU46372/72A patent/AU463690B2/en not_active Expired
- 1972-09-06 JP JP47088783A patent/JPS5248987B2/ja not_active Expired
- 1972-09-06 CA CA151,070A patent/CA986122A/en not_active Expired
- 1972-09-07 HU HURO678A patent/HU165428B/hu unknown
- 1972-09-07 EG EG365/72A patent/EG10717A/en active
- 1972-09-07 IL IL40321A patent/IL40321A/en unknown
- 1972-09-08 CH CH805474A patent/CH561014A5/xx not_active IP Right Cessation
- 1972-09-08 DE DE2244237A patent/DE2244237A1/en active Pending
- 1972-09-08 CH CH1325472A patent/CH555849A/en not_active IP Right Cessation
- 1972-09-08 AT AT772872A patent/AT317887B/en not_active IP Right Cessation
- 1972-09-08 CH CH805374A patent/CH555355A/en not_active IP Right Cessation
- 1972-09-08 AT AT930273A patent/AT317888B/en active
- 1972-09-08 AR AR243999A patent/AR194500A1/en active
- 1972-09-08 DK DK444972A patent/DK131676C/en active
- 1972-09-08 SE SE7211627A patent/SE376234B/xx unknown
- 1972-09-08 AT AT930373*7A patent/AT329917B/en not_active IP Right Cessation
- 1972-09-09 ES ES406548A patent/ES406548A1/en not_active Expired
- 1972-09-09 ES ES406550A patent/ES406550A1/en not_active Expired
- 1972-09-09 ES ES406549A patent/ES406549A1/en not_active Expired
- 1972-09-09 IT IT29011/72A patent/IT967312B/en active
- 1972-09-09 ES ES406551A patent/ES406551A1/en not_active Expired
-
1973
- 1973-03-13 SU SU1890140A patent/SU496735A3/en active
-
1975
- 1975-02-27 JP JP2349275A patent/JPS538699B2/ja not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0354622A1 (en) * | 1988-08-11 | 1990-02-14 | Shell Internationale Researchmaatschappij B.V. | Oxadiazolone herbicides |
Also Published As
| Publication number | Publication date |
|---|---|
| IL40321A0 (en) | 1972-11-28 |
| IL40321A (en) | 1975-03-13 |
| ES406550A1 (en) | 1975-09-01 |
| JPS538699B2 (en) | 1978-03-31 |
| AU4637272A (en) | 1974-03-14 |
| DE2244237A1 (en) | 1973-03-15 |
| ES406551A1 (en) | 1976-01-16 |
| CA986122A (en) | 1976-03-23 |
| AT317888B (en) | 1974-09-25 |
| JPS50140447A (en) | 1975-11-11 |
| HU165428B (en) | 1974-08-28 |
| ES406549A1 (en) | 1976-01-16 |
| CH561014A5 (en) | 1975-04-30 |
| OA04166A (en) | 1979-12-15 |
| SE376234B (en) | 1975-05-12 |
| AT329917B (en) | 1976-06-10 |
| IT967312B (en) | 1974-02-28 |
| DK131676B (en) | 1975-08-18 |
| JPS5248987B2 (en) | 1977-12-14 |
| JPS4839639A (en) | 1973-06-11 |
| EG10717A (en) | 1976-05-31 |
| AT317887B (en) | 1974-09-25 |
| ES406548A1 (en) | 1976-01-16 |
| RO62265A (en) | 1977-09-15 |
| CH555849A (en) | 1974-11-15 |
| AR194500A1 (en) | 1973-07-23 |
| CH555355A (en) | 1974-10-31 |
| SU496735A3 (en) | 1975-12-25 |
| ATA930373A (en) | 1975-08-15 |
| NL7211949A (en) | 1973-03-13 |
| AU463690B2 (en) | 1975-07-31 |
| BE788612A (en) | 1973-03-08 |
| DK131676C (en) | 1976-01-19 |
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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 |