DE1567052C3 - Oxadiazolonderivat, Verfahren zu seiner Herstellung und selektives Herbicid - Google Patents
Oxadiazolonderivat, Verfahren zu seiner Herstellung und selektives HerbicidInfo
- Publication number
- DE1567052C3 DE1567052C3 DE19641567052 DE1567052A DE1567052C3 DE 1567052 C3 DE1567052 C3 DE 1567052C3 DE 19641567052 DE19641567052 DE 19641567052 DE 1567052 A DE1567052 A DE 1567052A DE 1567052 C3 DE1567052 C3 DE 1567052C3
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- oxadiazolone
- selective herbicide
- formula
- derivative
- 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
- 238000000034 method Methods 0.000 title claims description 3
- ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical class O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 title description 7
- 230000002363 herbicidal effect Effects 0.000 title description 4
- 239000004009 herbicide Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical class O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- -1 benzene or toluene Chemical class 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZTPAUBJZUBGGEY-UHFFFAOYSA-N (2,4-dichlorophenyl)hydrazine Chemical compound NNC1=CC=C(Cl)C=C1Cl ZTPAUBJZUBGGEY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- OUMRPMOEVNYWPZ-UHFFFAOYSA-N N'-(2,4-dichlorophenyl)-2,2-dimethylpropanehydrazide Chemical compound CC(C)(C)C(=O)NNc1ccc(Cl)cc1Cl OUMRPMOEVNYWPZ-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Fertilizers (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR957151A FR1394774A (fr) | 1963-12-13 | 1963-12-13 | Nouveaux dérivés de l'oxadiazolone et leur préparation |
| FR36781A FR90369E (fr) | 1963-12-13 | 1965-10-29 | Nouveaux dérivés de l'oxadiazolone et leur préparation |
| US520674A US3385862A (en) | 1963-12-13 | 1966-01-14 | 5-t-butyl-3-phenyl-2-oxadiazolones |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1567052A1 DE1567052A1 (de) | 1970-07-23 |
| DE1567052B2 DE1567052B2 (de) | 1974-09-05 |
| DE1567052C3 true DE1567052C3 (de) | 1975-05-15 |
Family
ID=31950282
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641567052 Expired DE1567052C3 (de) | 1963-12-13 | 1964-12-11 | Oxadiazolonderivat, Verfahren zu seiner Herstellung und selektives Herbicid |
Country Status (11)
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4088472A (en) * | 1965-12-13 | 1978-05-09 | Monsanto Company | Agricultural procedure |
| US3718452A (en) * | 1969-10-24 | 1973-02-27 | Gulf Research Development Co | Combating unwanted vegetation with 2-aryl-5-substituted 1,3,4-oxadiazoles |
| FR2076487A5 (enrdf_load_stackoverflow) * | 1970-01-16 | 1971-10-15 | Rhone Poulenc Sa | |
| FR2141442B1 (enrdf_load_stackoverflow) * | 1971-06-02 | 1973-06-29 | Rhone Poulenc Sa | |
| FR2252337B1 (enrdf_load_stackoverflow) * | 1973-11-26 | 1976-10-01 | Rhone Poulenc Ind | |
| FR2320701A1 (fr) * | 1975-08-13 | 1977-03-11 | Rhone Poulenc Ind | Nouvelles compositions fongicides |
| BR8009033A (pt) * | 1980-02-05 | 1981-12-29 | Rhone Poulenc Agrochimie | Composicao para uao herbicida e processo de tratamento de cultura de algodoeiro |
| JPH075591B2 (ja) * | 1986-08-25 | 1995-01-25 | 住友化学工業株式会社 | ベンゾチアゾロン誘導体およびそれを有効成分とする除草剤 |
| WO1997009881A1 (en) * | 1995-09-15 | 1997-03-20 | E.I. Du Pont De Nemours And Company | Herbicidal mixtures |
| EP2052615A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
| DE102008037628A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Crop Science Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
| WO2014122196A1 (de) | 2013-02-08 | 2014-08-14 | Bayer Cropscience Ag | Emulsionskonzentrate enthaltend ein oxadiazole und ein chloracetamid |
| CN103880772B (zh) * | 2014-04-08 | 2016-05-04 | 连云港市金囤农化有限公司 | 一种丙炔噁草酮的制备方法 |
| CN110655477A (zh) * | 2019-10-25 | 2020-01-07 | 湖南兴同化学科技有限公司 | 一种噁草酮中间体的合成方法 |
| CN111226953A (zh) * | 2020-03-08 | 2020-06-05 | 安徽喜田生物科技有限公司 | 一种含有丙炔噁草酮和西草净的除草组合物 |
-
1963
- 1963-12-13 FR FR957151A patent/FR1394774A/fr not_active Expired
- 1963-12-13 BE BE657037A patent/BE657037A/xx unknown
-
1964
- 1964-12-04 CH CH1572764A patent/CH435853A/fr unknown
- 1964-12-08 SE SE1482764A patent/SE303293B/xx unknown
- 1964-12-11 DK DK610064A patent/DK109919C/da active
- 1964-12-11 IL IL2260764A patent/IL22607A/xx unknown
- 1964-12-11 DE DE19641567052 patent/DE1567052C3/de not_active Expired
- 1964-12-11 AT AT1055064A patent/AT254613B/de active
- 1964-12-11 GB GB5060964A patent/GB1063799A/en not_active Expired
- 1964-12-11 NL NL6414451A patent/NL6414451A/xx unknown
-
1965
- 1965-10-29 FR FR36781A patent/FR90369E/fr not_active Expired
-
1966
- 1966-01-25 BE BE675562D patent/BE675562A/xx unknown
- 1966-10-27 GB GB4826066A patent/GB1110500A/en not_active Expired
-
1970
- 1970-12-31 MY MY7000172A patent/MY7000172A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1567052A1 (de) | 1970-07-23 |
| DE1567052B2 (de) | 1974-09-05 |
| GB1110500A (en) | 1968-04-18 |
| GB1063799A (en) | 1967-03-30 |
| IL22607A (en) | 1968-04-25 |
| MY7000172A (en) | 1970-12-31 |
| DK109919C (da) | 1968-07-29 |
| BE657037A (enrdf_load_stackoverflow) | 1965-06-11 |
| SE303293B (enrdf_load_stackoverflow) | 1968-08-26 |
| NL6414451A (enrdf_load_stackoverflow) | 1965-06-14 |
| BE675562A (enrdf_load_stackoverflow) | 1966-07-25 |
| CH435853A (fr) | 1967-05-15 |
| FR90369E (fr) | 1967-12-01 |
| AT254613B (de) | 1967-05-26 |
| FR1394774A (fr) | 1965-04-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |