JPS6132312B2 - - Google Patents
Info
- Publication number
- JPS6132312B2 JPS6132312B2 JP55161385A JP16138580A JPS6132312B2 JP S6132312 B2 JPS6132312 B2 JP S6132312B2 JP 55161385 A JP55161385 A JP 55161385A JP 16138580 A JP16138580 A JP 16138580A JP S6132312 B2 JPS6132312 B2 JP S6132312B2
- Authority
- JP
- Japan
- Prior art keywords
- mmol
- crystals
- reaction
- benzoyl
- formula
- 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
- 239000002253 acid Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000013078 crystal Substances 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- -1 methylene compound Chemical class 0.000 description 15
- 239000007795 chemical reaction product Substances 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- PXQPEWDEAKTCGB-UHFFFAOYSA-N vitamin B13 Natural products OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- DSHWMBCJDOGPTB-UHFFFAOYSA-N ethyl 2-ethoxy-2-iminoacetate Chemical compound CCOC(=N)C(=O)OCC DSHWMBCJDOGPTB-UHFFFAOYSA-N 0.000 description 3
- 150000001469 hydantoins Chemical class 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229960005010 orotic acid Drugs 0.000 description 3
- ADDBAPLLQRBDLT-UHFFFAOYSA-N 2-ethoxyiminoacetic acid Chemical compound CCON=CC(O)=O ADDBAPLLQRBDLT-UHFFFAOYSA-N 0.000 description 2
- MZQQHYDUINOMDG-UHFFFAOYSA-N 3-methylimidazolidine-2,4-dione Chemical compound CN1C(=O)CNC1=O MZQQHYDUINOMDG-UHFFFAOYSA-N 0.000 description 2
- GDRPYBCODLVFIK-UHFFFAOYSA-N 5-benzoyl-3-methyl-2,4-dioxo-1h-pyrimidine-6-carboxylic acid Chemical compound O=C1N(C)C(=O)NC(C(O)=O)=C1C(=O)C1=CC=CC=C1 GDRPYBCODLVFIK-UHFFFAOYSA-N 0.000 description 2
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- LXKYIHKOIYPPQB-UHFFFAOYSA-N diethyl 2-acetyl-3-aminobut-2-enedioate Chemical group CCOC(=O)C(N)=C(C(C)=O)C(=O)OCC LXKYIHKOIYPPQB-UHFFFAOYSA-N 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- URFDSEBDUGSCLZ-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)imidazolidine-2,4-dione Chemical compound ClC1=CC(Cl)=CC(N2C(NC(=O)C2)=O)=C1 URFDSEBDUGSCLZ-UHFFFAOYSA-N 0.000 description 1
- MGYGFNQQGAQEON-UHFFFAOYSA-N 4-tolyl isocyanate Chemical compound CC1=CC=C(N=C=O)C=C1 MGYGFNQQGAQEON-UHFFFAOYSA-N 0.000 description 1
- UXNASIODGKLGKY-UHFFFAOYSA-N 5-acetyl-3-ethyl-2,4-dioxo-1h-pyrimidine-6-carboxylic acid Chemical compound CCN1C(=O)NC(C(O)=O)=C(C(C)=O)C1=O UXNASIODGKLGKY-UHFFFAOYSA-N 0.000 description 1
- JWFKWTNKGFCXOT-UHFFFAOYSA-N 5-benzoyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1h-pyrimidine-6-carboxylic acid Chemical compound O=C1C(C(=O)C=2C=CC=CC=2)=C(C(=O)O)NC(=O)N1C1=CC(Cl)=CC(Cl)=C1 JWFKWTNKGFCXOT-UHFFFAOYSA-N 0.000 description 1
- IGKRLHLBJMYMRA-UHFFFAOYSA-N 5-benzoyl-3-butyl-2,4-dioxo-1h-pyrimidine-6-carboxylic acid Chemical compound O=C1N(CCCC)C(=O)NC(C(O)=O)=C1C(=O)C1=CC=CC=C1 IGKRLHLBJMYMRA-UHFFFAOYSA-N 0.000 description 1
- XDLQYYGBTVDLRV-UHFFFAOYSA-N CCOC(=O)C(N)=C(C(=O)OC(C)C)C(=O)C1=CC=CC=C1 Chemical group CCOC(=O)C(N)=C(C(=O)OC(C)C)C(=O)C1=CC=CC=C1 XDLQYYGBTVDLRV-UHFFFAOYSA-N 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- RHYBFKMFHLPQPH-UHFFFAOYSA-N N-methylhydantoin Natural products CN1CC(=O)NC1=O RHYBFKMFHLPQPH-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000576755 Sclerotia Species 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 235000008206 alpha-amino acids Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- QCUHSHIJNZJHIM-UHFFFAOYSA-N diethyl 2-amino-3-benzoylbut-2-enedioate Chemical group CCOC(=O)C(N)=C(C(=O)OCC)C(=O)C1=CC=CC=C1 QCUHSHIJNZJHIM-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- FPWUAVKFMHNGHN-UHFFFAOYSA-N propan-2-yl 3-oxo-3-phenylpropanoate Chemical compound CC(C)OC(=O)CC(=O)C1=CC=CC=C1 FPWUAVKFMHNGHN-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55161385A JPS5785376A (en) | 1980-11-18 | 1980-11-18 | 5-acylorotic acid |
| US06/319,793 US4400508A (en) | 1980-11-18 | 1981-11-09 | Orotic acid derivatives |
| DE8181109628T DE3170766D1 (en) | 1980-11-18 | 1981-11-11 | Orotic acid derivatives and their use as agricultural chemicals |
| EP81109628A EP0052341B1 (en) | 1980-11-18 | 1981-11-11 | Orotic acid derivatives and their use as agricultural chemicals |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55161385A JPS5785376A (en) | 1980-11-18 | 1980-11-18 | 5-acylorotic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5785376A JPS5785376A (en) | 1982-05-28 |
| JPS6132312B2 true JPS6132312B2 (US07943777-20110517-C00090.png) | 1986-07-25 |
Family
ID=15734079
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55161385A Granted JPS5785376A (en) | 1980-11-18 | 1980-11-18 | 5-acylorotic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5785376A (US07943777-20110517-C00090.png) |
-
1980
- 1980-11-18 JP JP55161385A patent/JPS5785376A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5785376A (en) | 1982-05-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1773783B1 (fr) | Procede de preparation de derives n-piperidino-1,5-diphenylpyrazole-3-carboxamide | |
| JPS6155514B2 (US07943777-20110517-C00090.png) | ||
| JP3670314B2 (ja) | １−置換−５（４ｈ）−テトラゾリノン類の製造方法 | |
| EP0000200A1 (en) | New N-amidino-3,5-diamino-6-substituted-2-pyrazinecarboxamides and process for preparing same | |
| EP0052333B1 (en) | 4-fluoro-5-oxypyrazole derivate and preparation thereof | |
| NO165104B (no) | Analogifremgangsmaate til fremstilling av terapeutisk aktive 1, 1-disubstituerte cyklopropanderivater. | |
| AU638349B2 (en) | Heterocycle-substituted benzene derivative, production thereof, and herbicide containing the same as active ingredient | |
| KR100674098B1 (ko) | Ｎ,ｎ-디알킬아릴아민 촉매의 존재하에서ｎ-알크(엔)옥시(또는 아릴옥시)카보닐이소티오시아네이트 및 그의 유도체를 제조하는 방법 | |
| JPS6132312B2 (US07943777-20110517-C00090.png) | ||
| US5663365A (en) | Process for the preparation of pyrazolones | |
| EP0359474B1 (en) | Pyridazinone manufacture | |
| CA1229619A (en) | Method for the synthesis of 5-thio-1,2,3-thiadiazole | |
| JP3066594B2 (ja) | アニリン誘導体及びその製造法 | |
| EP0278542B1 (en) | Preparation of tetrazole compounds | |
| JPS60136572A (ja) | トリアゾロン誘導体の製造方法 | |
| EP0005280B1 (en) | A process for the reduction of carboxylic acid halides to corresponding aldehydes | |
| US2651638A (en) | Derivatives of i | |
| JPS6132311B2 (US07943777-20110517-C00090.png) | ||
| JPH04139170A (ja) | 置換ピリジンスルホニルカーバメート系化合物及びその製造方法並びに置換ピリジンスルホンアミド系化合物の製造方法 | |
| JPH0229672B2 (ja) | 11chikann55merukaputootetorazoorunoseizoho | |
| JPS62281867A (ja) | イミダゾ−ルカルボン酸エステル誘導体、その製造方法及び該誘導体を有効成分とする殺菌剤 | |
| JPH052673B2 (US07943777-20110517-C00090.png) | ||
| JPH0344375A (ja) | ５―ヒドロキシピラゾール類の製造法 | |
| JPS58154537A (ja) | オキシ安息香酸低級アルアルキルエステルの製造法 | |
| JPH0421666B2 (US07943777-20110517-C00090.png) |
