JPH0238588B2 - SHINKIHIDANTOINKAGOBUTSU - Google Patents
SHINKIHIDANTOINKAGOBUTSUInfo
- Publication number
- JPH0238588B2 JPH0238588B2 JP95481A JP95481A JPH0238588B2 JP H0238588 B2 JPH0238588 B2 JP H0238588B2 JP 95481 A JP95481 A JP 95481A JP 95481 A JP95481 A JP 95481A JP H0238588 B2 JPH0238588 B2 JP H0238588B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound represented
- general formula
- group
- alkyl group
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 229940091173 hydantoin Drugs 0.000 claims description 4
- -1 hydantoin compound Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000005648 plant growth regulator Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000035784 germination Effects 0.000 description 9
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methyl urea Chemical compound CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 4
- RHYBFKMFHLPQPH-UHFFFAOYSA-N N-methylhydantoin Chemical compound CN1CC(=O)NC1=O RHYBFKMFHLPQPH-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000209094 Oryza Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 230000001737 promoting effect Effects 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- UPSFNXFLBMJUQW-UHFFFAOYSA-N 5-hydroxy-1-methylimidazolidine-2,4-dione Chemical compound CN1C(O)C(=O)NC1=O UPSFNXFLBMJUQW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- UUQQVORIGBBIBE-UHFFFAOYSA-N butyl 2,2-dihydroxyacetate Chemical compound CCCCOC(=O)C(O)O UUQQVORIGBBIBE-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000007952 growth promoter Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- MOOYVEVEDVVKGD-UHFFFAOYSA-N oxaldehydic acid;hydrate Chemical compound O.OC(=O)C=O MOOYVEVEDVVKGD-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000003375 plant hormone Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Description
本発明は、次の一般式（）で表わされる新規
ヒダントイン化合物に関する。
（式中、R1は低級アルキル基、R2は水素又はア
シル基を表わす。）
該化合物は、文献未載の新規物質であり、それ
自体植物生長調整剤として有用であり、又、各種
ヒダントイン系化合物を製造するための合成原料
としても有用である。
本発明化合物（）は、種々の方法で製造しう
るが、例えば次の一般式（）で表わされる化合
物を、
（式中、R3は水素又はアルキル基を表わす。）
次の一般式（）で表わされる化合物と反応さ
せることにより、
製造することができる。本反応は、適宜水、アル
コール類その他適当な溶媒中、室温又は加熱して
行なう。
得られた化合物は、さらに常法によりアシル化
して、他の本発明化合物を得ることができる。
反応後は、通常の手段を用いて本発明化合物を
単離、精製することができ、又、ナトリウム、カ
リウム等との塩を形成させてもよい。
以下、実施例により本発明化合物の製造例を示
す。
実施例 １
ジヒドロキシ酢酸ブチル620mg及びＮ―メチル
尿素370mgを水10mlに溶かし、撹拌する。ろ過し
た後、ろ液を減圧濃縮し、酢酸エチルで抽出す
る。この抽出液を乾燥後、減圧乾固し、エタノー
ルからの分別結晶により５―ヒドロキシ―１―メ
チルヒダントイン230mgを得る。
融 点：135―136℃
元素分析値（C4H6N2O3）：
Ｃ％ Ｈ％ Ｎ％
計算値 36.93 4.65 21.53
実測値 37.13 4.66 21.53
NMR（d6―DMSO）：δ2.72（ｓ，3H）
4.96（ｄ，1H，Ｊ＝４）
6.84（ｄ，1H，Ｊ＝４）
10.64（bs，1H）
マススペクトル：ｍ／e130（M+）
実施例 ２
グリオキシル酸水和物9.2ｇ及びＮ―メチル尿
素7.4ｇを80％酢酸中１時間還流する。難溶物を
濾別し、濾液を減圧乾固する。残渣を少量の酢酸
エチルに溶解し、シリカゲルカラムで精製した
後、酢酸エチルで再結晶して５―ヒドロキシ―１
―メチルヒダントイン1.42ｇを白色結晶として得
る。融点等の物性値は実施例１のものと一致し
た。
上記実施例で得られた本発明化合物の植物生長
調整作用の一例を以下に示す。
） 稲の発芽促進作用
昭和55年産の水稲（金南風）を使用し、発芽
力検定試験を行なつた。発芽床として被験液で
浸したろ紙をペトリ皿中に入れ、供試種子数は
各群100粒とし、温度は30±１℃、暗所で実験
を行なつた。比較薬としては、１―メチルヒダ
ントインを用いた。
表１に示したとおり、10日間で発芽歩合は各
群ともほぼ100％であつたが、４日目での発芽
勢、平均発芽日数、発芽係数とも本発明化合物
の強い発芽促進作用を示した。
The present invention relates to a novel hydantoin compound represented by the following general formula (). (In the formula, R 1 represents a lower alkyl group, and R 2 represents a hydrogen or acyl group.) This compound is a new substance that has not been described in any literature, and is itself useful as a plant growth regulator. It is also useful as a synthetic raw material for producing based compounds. The compound () of the present invention can be produced by various methods, but for example, a compound represented by the following general formula (), (In the formula, R 3 represents hydrogen or an alkyl group.) By reacting with a compound represented by the following general formula (), can be manufactured. This reaction is carried out in water, alcohols or other suitable solvents at room temperature or with heating. The obtained compound can be further acylated by a conventional method to obtain other compounds of the present invention. After the reaction, the compound of the present invention can be isolated and purified using conventional means, and salts with sodium, potassium, etc. may be formed. Hereinafter, examples of manufacturing the compounds of the present invention will be shown in Examples. Example 1 620 mg of butyl dihydroxyacetate and 370 mg of N-methylurea are dissolved in 10 ml of water and stirred. After filtration, the filtrate is concentrated under reduced pressure and extracted with ethyl acetate. After drying this extract, it was evaporated to dryness under reduced pressure, and 230 mg of 5-hydroxy-1-methylhydantoin was obtained by fractional crystallization from ethanol. Melting point: 135-136℃ Elemental analysis value (C 4 H 6 N 2 O 3 ): C% H% N% Calculated value 36.93 4.65 21.53 Actual value 37.13 4.66 21.53 NMR (d 6 -DMSO): δ2.72 (s , 3H) 4.96 (d, 1H, J = 4) 6.84 (d, 1H, J = 4) 10.64 (bs, 1H) Mass spectrum: m/e130 (M + ) Example 2 9.2 g of glyoxylic acid hydrate and 7.4 g of N-methylurea is refluxed in 80% acetic acid for 1 hour. Slightly soluble substances are filtered off, and the filtrate is dried under reduced pressure. The residue was dissolved in a small amount of ethyl acetate, purified with a silica gel column, and then recrystallized with ethyl acetate to obtain 5-hydroxy-1
- Obtain 1.42 g of methylhydantoin as white crystals. Physical properties such as melting point were consistent with those of Example 1. An example of the plant growth regulating action of the compound of the present invention obtained in the above example is shown below. ) Germination promoting effect on rice A germination test was conducted using rice grown in 1980 (Kinnanfu). A filter paper soaked with the test liquid was placed in a Petri dish as a germination bed, the number of seeds tested was 100 in each group, and the experiment was conducted at a temperature of 30±1°C in a dark place. 1-methylhydantoin was used as a comparative drug. As shown in Table 1, the germination rate was almost 100% in each group in 10 days, but the germination intensity on the 4th day, the average number of germination days, and the germination coefficient all showed the strong germination promoting effect of the compound of the present invention. .
【表】
） 稲の初期生育促進作用
）の実験で４日目と５日目に発芽した種子
の内、49粒を無作為抽出し、水耕用被験液上に
置いた床に移床し、７日間フアイトトロン中で
栽培してその変化を観察した。
表２に示したとおり、本発明化合物で処理し
た種子は根付きがよく全部着床したが、対照群
では49粒中４粒は根付かなかつた。また、移床
７日後の地上部の長さ及び地下部（種子根）の
長さとも、本発明化合物群では有意に長く、１
―メチルヒダントインの１／100の濃度でこれ
と同程度の効果を示した。[Table] 49 seeds that germinated on the 4th and 5th day of the experiment (Promoting effect on early rice growth) were randomly selected and transferred to a bed placed on a hydroponic test solution. The cells were cultivated in a phytotron for 7 days and their changes were observed. As shown in Table 2, the seeds treated with the compound of the present invention took root well and all of them took root, whereas in the control group, 4 out of 49 seeds did not take root. In addition, both the length of the above-ground part and the length of the underground part (seed root) after 7 days of transfer were significantly longer in the compound group of the present invention;
- It showed similar effects at a concentration of 1/100 of methylhydantoin.
【表】
以上示したように、本発明化合物は植物生長調
整作用を有し、従つて、例えば発芽促進剤、生長
促進剤、発根促進剤として用いられ、又、植物ホ
ルモン・シナージスト（synergist）、種なし果実
の誘起剤等としてもその用途が期待される。[Table] As shown above, the compound of the present invention has a plant growth regulating effect, and is therefore used, for example, as a germination promoter, growth promoter, rooting promoter, and as a plant hormone synergist. It is also expected to be used as an inducer for seedless fruits.
Claims (1)
化合物。 （式中、R1は低級アルキル基、R2は水素又はア
シル基を表わす。） ２ 一般式（）で表わされる化合物を、 （式中、R3は水素又はアルキル基を表わす。） 一般式（）で表わされる化合物と反応させ、 （式中、R1は下記の基を表わす。） さらに、所望によりアシル化することを特徴と
する一般式（）で表わされる新規ヒダントイン
化合物の製造方法。 （式中、R1は低級アルキル基、R2は水素又はア
シル基を表わす。） ３ 一般式（）で表わされる新規ヒダントイン
化合物を有効成分として含有する植物生長調整
剤。 （式中、R1は低級アルキル基、R2は水素又はア
シル基を表わす。）[Claims] 1. A novel hydantoin compound represented by the general formula (). (In the formula, R 1 represents a lower alkyl group, R 2 represents hydrogen or an acyl group.) 2 A compound represented by the general formula (), (In the formula, R 3 represents hydrogen or an alkyl group.) React with a compound represented by the general formula (), (In the formula, R 1 represents the following group.) A method for producing a novel hydantoin compound represented by the general formula (), further comprising acylation if desired. (In the formula, R 1 represents a lower alkyl group, and R 2 represents a hydrogen or acyl group.) 3. A plant growth regulator containing a novel hydantoin compound represented by the general formula () as an active ingredient. (In the formula, R 1 represents a lower alkyl group, and R 2 represents hydrogen or an acyl group.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP95481A JPH0238588B2 (en) | 1981-01-06 | 1981-01-06 | SHINKIHIDANTOINKAGOBUTSU |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP95481A JPH0238588B2 (en) | 1981-01-06 | 1981-01-06 | SHINKIHIDANTOINKAGOBUTSU |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57114578A JPS57114578A (en) | 1982-07-16 |
| JPH0238588B2 true JPH0238588B2 (en) | 1990-08-31 |
Family
ID=11488059
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP95481A Expired - Lifetime JPH0238588B2 (en) | 1981-01-06 | 1981-01-06 | SHINKIHIDANTOINKAGOBUTSU |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0238588B2 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH062748B2 (en) * | 1984-03-08 | 1994-01-12 | 日本臓器製薬株式会社 | Novel hydantoin derivative and pharmaceutical composition containing the compound as an active ingredient |
| JPH0686436B2 (en) * | 1984-11-15 | 1994-11-02 | 日本臓器製薬株式会社 | Novel hydantoin derivative and pharmaceutical composition containing the compound |
| TWI353979B (en) | 2002-04-10 | 2011-12-11 | Nippon Zoki Pharmaceutical Co | Novel crystal form of 5-hydroxy-1-methylhydantoin |
| MX2016010892A (en) | 2014-02-26 | 2016-11-17 | Nippon Zoki Pharmaceutical Co | Agent for improving or preventing progression of chronic kidney disease. |
| US11464762B2 (en) | 2017-06-13 | 2022-10-11 | National Cancer Center | Carcinogenesis inhibitor |
-
1981
- 1981-01-06 JP JP95481A patent/JPH0238588B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57114578A (en) | 1982-07-16 |
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