ES451145A1 - 1,2,4-oxadiazin-5-one derivatives having phytohormonal and herbicidal activity - Google Patents
1,2,4-oxadiazin-5-one derivatives having phytohormonal and herbicidal activityInfo
- Publication number
- ES451145A1 ES451145A1 ES451145A ES451145A ES451145A1 ES 451145 A1 ES451145 A1 ES 451145A1 ES 451145 A ES451145 A ES 451145A ES 451145 A ES451145 A ES 451145A ES 451145 A1 ES451145 A1 ES 451145A1
- Authority
- ES
- Spain
- Prior art keywords
- carbon atoms
- part contains
- alkyl part
- whose alkyl
- atoms
- 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
- AXVRAYSRZWEUFX-UHFFFAOYSA-N 2h-1,2,4-oxadiazin-5-one Chemical class O=C1CONC=N1 AXVRAYSRZWEUFX-UHFFFAOYSA-N 0.000 title 1
- 230000002363 herbicidal effect Effects 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 13
- 125000000217 alkyl group Chemical group 0.000 abstract 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 4
- 229910052799 carbon Inorganic materials 0.000 abstract 4
- 125000004429 atom Chemical group 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- -1 trifluoromethoxy, trifluoromethylthio, carboxy Chemical group 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/04—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Procedure for the preparation of new derivatives of oxadiazine-1,2,4 ona-5, of general formula: **(See formula)** in which: R represents a hydrogen atom or an alkyl radical containing 1 to 4 carbon or phenyl atoms, Ar represents a phenyl radical substituted by 1 to 3 identical or different substituents, selected from halogen atoms and alkyl radicals containing 1 to 4 hydroxy carbon atoms, alkyloxyls whose alkyl part contains 1 to 4 carbon atoms, alkylthio whose alkyl part contains 1 to 4 carbon atoms, alkylsulfinyl whose alkyl part contains 1 to 4 carbon atoms, alkylsulfonyl whose alkyl part contains 1 to 4 carbon atoms, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, carboxy, alkyloxycarbonyl whose alkyl part contains 1 to 4 carbon atoms, nitro, amino, alkylamino whose alkyl part contains 1 to 4 carbon atoms, dialkylamino whose alkyl part contains 1 to 4 carbon atoms, acylinin whose acyl part contains 1 to 4 carbon atoms, alkyloxycarbonylamino whose alkyl part contains 1 to 4 a atoms of carbon, acid, alkanyl containing 1 to 4 carbon atoms, sulfamyl, dialkylsulfamyl of which each part contains 1 to 4 carbon or phenyl atoms, or a 5-ring aromatic heterocyclic radical containing as heteroatom an atom of oxygen, sulfur or nitrogen, optionally substituted by an atom or radical selected from halogen atoms, containing the radicals alkyl 1 to 4 carbon atoms, phenylalkyl whose alkyl part contains 1 to 4 carbon atoms, alkyloxy whose alkyl part contains 1 to 4 carbon or alkylthio atoms whose alkyl part contains 1 to 4 carbon atoms, characterized in that it comprises in a first step, reacting an α-halogenoester of general formula: **(See formula)** in which R and R1 are defined as in claim 1 and Y represents a halogen atom, on an amidoxime of general formula: **(See formula)** in which Ar is defined as in claim 1, in an alcoholic medium in the presence of an alkaline condensation agent at a temperature between 2º and 80ºC, and in a second stage, cyclizing a product of general formula: **(See formula)** in which Ar and R are as defined above, and R1 represents an alkyl radical containing 1 to 4 carbon atoms, heating the product in basic medium. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7527885A FR2323692A1 (en) | 1975-09-11 | 1975-09-11 | NEW DERIVATIVES OF DIHYDRO-5,6 4H-OXADIAZINE-1,2,4 ONE-5, THEIR PREPARATION AND THE COMPOSITIONS WITH HERBICIDE PROPERTIES CONTAINING THEM |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES451145A1 true ES451145A1 (en) | 1977-11-16 |
Family
ID=9159863
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES451145A Expired ES451145A1 (en) | 1975-09-11 | 1976-09-01 | 1,2,4-oxadiazin-5-one derivatives having phytohormonal and herbicidal activity |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS5236679A (en) |
| AR (1) | AR222625A1 (en) |
| AT (1) | AT346852B (en) |
| BE (1) | BE846083A (en) |
| BR (1) | BR7606002A (en) |
| CA (1) | CA1092109A (en) |
| CH (1) | CH600766A5 (en) |
| DD (1) | DD129024A5 (en) |
| DE (1) | DE2640464A1 (en) |
| DK (1) | DK410776A (en) |
| ES (1) | ES451145A1 (en) |
| FR (1) | FR2323692A1 (en) |
| GB (1) | GB1501589A (en) |
| HU (1) | HU176418B (en) |
| IE (1) | IE43946B1 (en) |
| IL (1) | IL50464A (en) |
| LU (1) | LU75767A1 (en) |
| NL (1) | NL7610067A (en) |
| PL (1) | PL101303B1 (en) |
| PT (1) | PT65574B (en) |
| RO (1) | RO69406A (en) |
| SE (1) | SE7610051L (en) |
| SU (1) | SU625608A3 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2497202A1 (en) * | 1980-12-31 | 1982-07-02 | Richter Gedeon Vegyeszet | NOVEL TETRAHYDRO-1,2,4-OXADIAZIN-5-ONE DERIVATIVES, THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME |
| HU181588B (en) * | 1980-12-31 | 1983-10-28 | Richter Gedeon Vegyeszet | Process for preparing n4-substituted tetrahydro-1,2,4-oxadiazin-5-one derivatives with anticonvulsive effect |
| DE3514450A1 (en) * | 1985-04-22 | 1986-10-23 | Hoechst Ag, 6230 Frankfurt | METHOD FOR PRODUCING IMIDATES AND NEW ARYL-SUBSTITUTED IMIDATES |
| JPS63173419A (en) * | 1987-01-12 | 1988-07-18 | Fujitsu Ltd | Atomic oscillator |
| CN107629020B (en) * | 2017-09-28 | 2020-09-04 | 湖北科技学院 | A kind of 4H-1,2,4-oxadiazine-5(6H)-one compound and its synthesis method |
-
1975
- 1975-09-11 FR FR7527885A patent/FR2323692A1/en active Granted
-
1976
- 1976-09-01 ES ES451145A patent/ES451145A1/en not_active Expired
- 1976-09-08 DD DD7600194682A patent/DD129024A5/en unknown
- 1976-09-08 GB GB37226/76A patent/GB1501589A/en not_active Expired
- 1976-09-08 IE IE2009/76A patent/IE43946B1/en unknown
- 1976-09-08 DE DE19762640464 patent/DE2640464A1/en not_active Withdrawn
- 1976-09-08 CA CA260,696A patent/CA1092109A/en not_active Expired
- 1976-09-09 SU SU762395116A patent/SU625608A3/en active
- 1976-09-10 PL PL1976192320A patent/PL101303B1/en unknown
- 1976-09-10 NL NL7610067A patent/NL7610067A/en not_active Application Discontinuation
- 1976-09-10 PT PT65574A patent/PT65574B/en unknown
- 1976-09-10 SE SE7610051A patent/SE7610051L/en not_active Application Discontinuation
- 1976-09-10 DK DK410776A patent/DK410776A/en unknown
- 1976-09-10 BR BR7606002A patent/BR7606002A/en unknown
- 1976-09-10 RO RO7687500A patent/RO69406A/en unknown
- 1976-09-10 AT AT669876A patent/AT346852B/en not_active IP Right Cessation
- 1976-09-10 LU LU75767A patent/LU75767A1/xx unknown
- 1976-09-10 HU HU76PI538A patent/HU176418B/en unknown
- 1976-09-10 JP JP51109353A patent/JPS5236679A/en active Pending
- 1976-09-10 IL IL50464A patent/IL50464A/en unknown
- 1976-09-10 CH CH1155976A patent/CH600766A5/xx not_active IP Right Cessation
- 1976-09-10 AR AR264651A patent/AR222625A1/en active
- 1976-09-10 BE BE170534A patent/BE846083A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7610067A (en) | 1977-03-15 |
| ATA669876A (en) | 1978-04-15 |
| RO69406A (en) | 1982-09-09 |
| FR2323692B1 (en) | 1978-10-27 |
| DK410776A (en) | 1977-03-12 |
| GB1501589A (en) | 1978-02-15 |
| IE43946L (en) | 1977-03-11 |
| CA1092109A (en) | 1980-12-23 |
| PT65574B (en) | 1978-07-04 |
| FR2323692A1 (en) | 1977-04-08 |
| SU625608A3 (en) | 1978-09-25 |
| IE43946B1 (en) | 1981-07-01 |
| DE2640464A1 (en) | 1977-04-14 |
| AT346852B (en) | 1978-11-27 |
| IL50464A0 (en) | 1976-11-30 |
| BE846083A (en) | 1977-03-10 |
| HU176418B (en) | 1981-02-28 |
| PL101303B1 (en) | 1978-12-30 |
| DD129024A5 (en) | 1977-12-21 |
| CH600766A5 (en) | 1978-06-30 |
| AR222625A1 (en) | 1981-06-15 |
| PT65574A (en) | 1976-10-01 |
| SE7610051L (en) | 1977-03-12 |
| IL50464A (en) | 1979-03-12 |
| BR7606002A (en) | 1977-08-23 |
| JPS5236679A (en) | 1977-03-22 |
| LU75767A1 (en) | 1978-05-12 |
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