JPS6132311B2 - - Google Patents
Info
- Publication number
- JPS6132311B2 JPS6132311B2 JP55161384A JP16138480A JPS6132311B2 JP S6132311 B2 JPS6132311 B2 JP S6132311B2 JP 55161384 A JP55161384 A JP 55161384A JP 16138480 A JP16138480 A JP 16138480A JP S6132311 B2 JPS6132311 B2 JP S6132311B2
- Authority
- JP
- Japan
- Prior art keywords
- mmol
- formula
- crystals
- added
- mixture
- 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
- -1 5-carboxyorotic acid alkali metal salt Chemical class 0.000 claims description 16
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 150000001340 alkali metals Chemical class 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
- 239000013078 crystal Substances 0.000 description 23
- 239000000203 mixture Substances 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000007795 chemical reaction product Substances 0.000 description 12
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- ADNYRESTPVTTEP-UHFFFAOYSA-N 2,4-dioxo-1h-pyrimidine-5,6-dicarboxylic acid Chemical compound OC(=O)C=1NC(=O)NC(=O)C=1C(O)=O ADNYRESTPVTTEP-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 150000001469 hydantoins Chemical class 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 description 3
- NXQJDVBMMRCKQG-UHFFFAOYSA-N 5-phenylimidazolidine-2,4-dione Chemical compound O=C1NC(=O)NC1C1=CC=CC=C1 NXQJDVBMMRCKQG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- HIIZOYBOCSCLPH-UHFFFAOYSA-N 1,3-bis(4-methylphenyl)urea Chemical compound C1=CC(C)=CC=C1NC(=O)NC1=CC=C(C)C=C1 HIIZOYBOCSCLPH-UHFFFAOYSA-N 0.000 description 1
- MIUFTVKWLAFLSL-UHFFFAOYSA-N 1-(4-chlorophenyl)imidazolidine-2,4-dione Chemical compound C1=CC(Cl)=CC=C1N1C(=O)NC(=O)C1 MIUFTVKWLAFLSL-UHFFFAOYSA-N 0.000 description 1
- RFLFIALFVCLGHM-UHFFFAOYSA-N 1-(4-methylphenyl)imidazolidine-2,4-dione Chemical compound C1=CC(C)=CC=C1N1C(=O)NC(=O)C1 RFLFIALFVCLGHM-UHFFFAOYSA-N 0.000 description 1
- VJUNTPRQTFDQMF-UHFFFAOYSA-N 1-benzylimidazolidine-2,4-dione Chemical compound O=C1NC(=O)CN1CC1=CC=CC=C1 VJUNTPRQTFDQMF-UHFFFAOYSA-N 0.000 description 1
- NOHNSECEKFOVGT-UHFFFAOYSA-N 1-butylimidazolidine-2,4-dione Chemical compound CCCCN1CC(=O)NC1=O NOHNSECEKFOVGT-UHFFFAOYSA-N 0.000 description 1
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- ZNQCSLYENQIUMJ-UHFFFAOYSA-N 4,4'-dichlorocarbanilide Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 ZNQCSLYENQIUMJ-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
- DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241001558929 Sclerotium <basidiomycota> Species 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- KFSZGBHNIHLIAA-UHFFFAOYSA-M benzyl(trimethyl)azanium;fluoride Chemical compound [F-].C[N+](C)(C)CC1=CC=CC=C1 KFSZGBHNIHLIAA-UHFFFAOYSA-M 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- HJMZMZRCABDKKV-UHFFFAOYSA-M cyanoformate Chemical compound [O-]C(=O)C#N HJMZMZRCABDKKV-UHFFFAOYSA-M 0.000 description 1
- QIHAINWYHBXORT-UHFFFAOYSA-N diethyl 2-(1-benzyl-2,5-dioxoimidazolidin-4-ylidene)propanedioate Chemical compound O=C1C(=C(C(=O)OCC)C(=O)OCC)NC(=O)N1CC1=CC=CC=C1 QIHAINWYHBXORT-UHFFFAOYSA-N 0.000 description 1
- XMMXTVMCQPYQGT-UHFFFAOYSA-N diethyl 2-(1-butyl-2,5-dioxoimidazolidin-4-ylidene)propanedioate Chemical compound CCCCN1C(=O)NC(=C(C(=O)OCC)C(=O)OCC)C1=O XMMXTVMCQPYQGT-UHFFFAOYSA-N 0.000 description 1
- BTRMIAMPUNPMBX-UHFFFAOYSA-N diethyl 2-[1-(4-chlorophenyl)-2,5-dioxoimidazolidin-4-ylidene]propanedioate Chemical compound O=C1C(=C(C(=O)OCC)C(=O)OCC)NC(=O)N1C1=CC=C(Cl)C=C1 BTRMIAMPUNPMBX-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- MSMGXWFHBSCQFB-UHFFFAOYSA-N ethyl cyanoformate Chemical compound CCOC(=O)C#N MSMGXWFHBSCQFB-UHFFFAOYSA-N 0.000 description 1
- BQBKYSPXQYHTIP-UHFFFAOYSA-N ethyl n-butylcarbamate Chemical compound CCCCNC(=O)OCC BQBKYSPXQYHTIP-UHFFFAOYSA-N 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 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
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- OWXIHIGBSUWWJN-UHFFFAOYSA-M lithium;5-carboxy-3-(4-methylphenyl)-2,4-dioxo-1h-pyrimidine-6-carboxylate Chemical compound [Li+].C1=CC(C)=CC=C1N1C(=O)C(C(O)=O)=C(C([O-])=O)NC1=O OWXIHIGBSUWWJN-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- YRFJOTIPGIWBJA-UHFFFAOYSA-M potassium;3-benzyl-5-carboxy-2,4-dioxo-1h-pyrimidine-6-carboxylate Chemical compound [K+].O=C1C(C(=O)O)=C(C([O-])=O)NC(=O)N1CC1=CC=CC=C1 YRFJOTIPGIWBJA-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- ZTHMWDSJKLNDTE-UHFFFAOYSA-M sodium orotate Chemical class [Na+].[O-]C(=O)C1=CC(=O)NC(=O)N1 ZTHMWDSJKLNDTE-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- PMHBYAGKMHEFPA-UHFFFAOYSA-N triethyl ethene-1,1,2-tricarboxylate Chemical group CCOC(=O)C=C(C(=O)OCC)C(=O)OCC PMHBYAGKMHEFPA-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55161384A JPS5785375A (en) | 1980-11-18 | 1980-11-18 | Alkali metallic salt of 5-carboxyorotic acid |
| US06/319,793 US4400508A (en) | 1980-11-18 | 1981-11-09 | Orotic acid derivatives |
| EP81109628A EP0052341B1 (en) | 1980-11-18 | 1981-11-11 | Orotic acid derivatives and their use as agricultural chemicals |
| DE8181109628T DE3170766D1 (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 |
|---|---|---|---|
| JP55161384A JPS5785375A (en) | 1980-11-18 | 1980-11-18 | Alkali metallic salt of 5-carboxyorotic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5785375A JPS5785375A (en) | 1982-05-28 |
| JPS6132311B2 true JPS6132311B2 (xx) | 1986-07-25 |
Family
ID=15734059
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55161384A Granted JPS5785375A (en) | 1980-11-18 | 1980-11-18 | Alkali metallic salt of 5-carboxyorotic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5785375A (xx) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3581243B2 (ja) * | 1996-12-20 | 2004-10-27 | セイコーエプソン株式会社 | 顔料塊状体及びその製造方法、顔料水系分散液、並びに水系インク組成物 |
-
1980
- 1980-11-18 JP JP55161384A patent/JPS5785375A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5785375A (en) | 1982-05-28 |
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