JPS6272687A - Novel imidazole compound and production thereof - Google Patents

Novel imidazole compound and production thereof

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Publication number
JPS6272687A
JPS6272687A JP21432285A JP21432285A JPS6272687A JP S6272687 A JPS6272687 A JP S6272687A JP 21432285 A JP21432285 A JP 21432285A JP 21432285 A JP21432285 A JP 21432285A JP S6272687 A JPS6272687 A JP S6272687A
Authority
JP
Japan
Prior art keywords
formula
chlorothien
imidazole compound
imidazolyl
production
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.)
Granted
Application number
JP21432285A
Other languages
Japanese (ja)
Other versions
JPH0380157B2 (en
Inventor
Takayuki Fujita
孝行 藤田
Hiroko Yabe
矢部　浩子
Tadashi Akita
正 秋田
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shikoku Chemicals Corp
Original Assignee
Shikoku Chemicals Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Shikoku Chemicals Corp filed Critical Shikoku Chemicals Corp
Priority to JP21432285A priority Critical patent/JPS6272687A/en
Priority to US06/906,432 priority patent/US4720551A/en
Priority to EP86307169A priority patent/EP0218398A3/en
Publication of JPS6272687A publication Critical patent/JPS6272687A/en
Publication of JPH0380157B2 publication Critical patent/JPH0380157B2/ja
Granted legal-status Critical Current

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  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

NEW MATERIAL:A compound expressed by formula I (R1 and R2 represent H or Cl, and at least one thereof is Cl). EXAMPLE:1-( 5-Chlorothien-2-yl )-2-(1H-imidazolyl)-3-(2,4-dichloro-phenyl)-2-propen-1- one. USE:An antimold, antifungal agent, etc. PREPARATION:1-(5-Chlorothien-2-yl)-2-(1H-imidazolyl)ethanone expressed by formula II is reacted with a benzaldehyde compound expressed by formula III.

Description

【発明の詳細な説明】 この発明は、新規なイミダゾール化合物及びその製造方
法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel imidazole compound and a method for producing the same.

本発明の新規なイミダゾール化合物は、一般式 （但し、式中Ｒ２及びＲ２は水素原子または塩素原子で
あり、少なくとも１つは塩素原子を表す。）で示され、
前記化合物は、 構造式 で示される１−（５−’クロロチエンー２−イル）−２
−（ＩＨ−イミダゾリル）エタノンと下記一般式で示さ
れるベンズアルデヒド化合物 一般式 （但し、式中Ｒ９及びＲ２は前記と同じである。）を反
応させて合成することができる。The novel imidazole compound of the present invention is represented by the general formula (wherein R2 and R2 are hydrogen atoms or chlorine atoms, and at least one represents a chlorine atom),
The compound has the following structural formula: 1-(5-'chlorothien-2-yl)-2
It can be synthesized by reacting -(IH-imidazolyl)ethanone with a benzaldehyde compound represented by the following general formula (in which R9 and R2 are the same as above).

本発明の化合物は、抗カビ剤、抗真菌剤等として有用で
あり、その特性は次のとおりである。The compound of the present invention is useful as an antifungal agent, an antifungal agent, etc., and its properties are as follows.

白〜黄色結晶、中性、水に不溶、エタノール、クロロホ
ルム、酢酸エチル、石油エーテル、アセトニトリル、イ
ソプロパツール及びエチルエーテルに可溶。White to yellow crystals, neutral, insoluble in water, soluble in ethanol, chloroform, ethyl acetate, petroleum ether, acetonitrile, isopropanol and ethyl ether.

本発明化合物の製法を具体的に説明すると、１−（５−
クロロチエン−２−イル）　−２−（ＩＨ−イミダゾリ
ル）エタノン１モルにベンズアルデヒド化合物１モルを
ピペリジンの存在下に無水ベンゼン等の溶媒中で６０〜
８０℃の温度に加熱して反応させた後、溶媒を減圧留去
し、残渣をシリカゲルクロマトグラフィーにかけて分離
精製するかあるいは、残渣に酢酸エチル、イソプロピル
エーテル等の溶媒を加えることにより、結晶化させ、次
いで酢酸エチル、石油エーテル、アセトニトリル、イソ
プロピルエーテル等の溶媒を用いて再結晶すれば良い。To specifically explain the method for producing the compound of the present invention, 1-(5-
chlorothien-2-yl)-2-(IH-imidazolyl)ethanone and 1 mol of a benzaldehyde compound in the presence of piperidine in a solvent such as anhydrous benzene for 60 to
After heating to a temperature of 80°C to react, the solvent is distilled off under reduced pressure, and the residue is separated and purified by silica gel chromatography, or crystallized by adding a solvent such as ethyl acetate or isopropyl ether to the residue. Then, recrystallization may be performed using a solvent such as ethyl acetate, petroleum ether, acetonitrile, or isopropyl ether.

実施例１ ■−（５−クロロチエン−２−イル）−２−（１）１−
イミダゾリル）　−３−（，２，４−ジクロロフェニル
）−２−プロペン−１−オンの製造 １−（５−クロロチエン−２−イル）−２−（１１１−
イミダゾリル）エタノン３．４ｇと２．４−ジクロロベ
ンズアルデヒド２．７ｇを無水ベンゼン８０ｍ６に溶か
した溶液にピペリジン０．２ｍｊ２を加え、ディーン・
スタークトラップを付けて、７時間還流後、溶媒を減圧
留去し、残渣をシリカゲルクロマトグラフィー（クロロ
ホルム：メタノール＝２０：１）にかけ、分離精製を行
い、これに酢酸エチル、イソプロピルエーテルで再結晶
し、融点１１０〜１１１℃の白色結晶２．１ｇを得た。Example 1 ■-(5-chlorothien-2-yl)-2-(1)1-
Preparation of 1-(5-chlorothien-2-yl)-2-(111-
To a solution of 3.4 g of imidazolyl) ethanone and 2.7 g of 2,4-dichlorobenzaldehyde dissolved in 80 m6 of anhydrous benzene, 0.2 mj2 of piperidine was added.
After refluxing for 7 hours with a Stark trap, the solvent was distilled off under reduced pressure, and the residue was separated and purified by silica gel chromatography (chloroform:methanol = 20:1), which was then recrystallized from ethyl acetate and isopropyl ether. , 2.1 g of white crystals with a melting point of 110-111°C were obtained.

本島は分析の結果、下記の構造式で示される１−（５−
クロロチエン−２−イル）　−２−（１Ｂ−イミダゾリ
ル）　−３−（２，４−ジクロロフェニル）−２−プロ
ペン−１−オンと認められ、その収率は３７％であった
。As a result of analysis, the main island has the following structural formula: 1-(5-
It was recognized as chlorothien-2-yl)-2-(1B-imidazolyl)-3-(2,4-dichlorophenyl)-2-propen-1-one, and the yield was 37%.

（分析結果） 元素分析（Ｃ＋　６Ｈ９ＮＺＯＳＣ１３として、％）分
析値　Ｃ：５０．１９　、Ｈ：２．１５、Ｎニア、６１
計算値　Ｃ：５０．０９　、旧２．３６、Ｎニア、３０
ＬＣ Ｒｆ　：０．７９　（酢酸エチル：アセトン＝　５　：
１）Ｒｆ　：０．８０　（クロロホルム：メタノール＝
１０：ｌ） 実施例２ ｌ−（５−クロロチエン−２−イル）−２−（Ｉｌ＋−
イミダゾリル）−３−（４−クロロフェニル）−２−プ
ロペン−１−オンの製造 １−（５−クロロチエン−２−イル）−２−（ＩＨ−イ
ミダゾリル）エタノン３．４ｇと４−クロロベンズアル
デヒド２．１ｇを無水ベンゼン８０ｍ１に溶かした溶液
にピペリジン０．２ｍｊ２を加え、ディーン・スターク
トラップを付けて、６時間還流後、溶媒を減圧留去し、
残渣に酢酸エチル、イソプロピルエーテルを加えて結晶
化させ、酢酸エチルを用いて再結晶し、融点１３７〜１
３８℃の黄色結晶１．７ｇを得た。本島は分折の結果、
下記の構造式で示される１−（５−クロロチエン−２−
イル）−２−（Ｉｌｌ−イミダゾリル”）　−３−（４
−クロロフェニル）−２−プロペン−１−オンと認めら
れ、その収率は３２％であった。(Analysis results) Elemental analysis (% as C+ 6H9NZOSC13) Analysis value C: 50.19, H: 2.15, N near, 61
Calculated value C: 50.09, old 2.36, N near, 30
LC Rf: 0.79 (ethyl acetate: acetone = 5:
1) Rf: 0.80 (chloroform:methanol=
10:l) Example 2 l-(5-chlorothien-2-yl)-2-(Il+-
Preparation of 1-(5-chlorothien-2-yl)-2-(IH-imidazolyl)ethanone and 4-chlorobenzaldehyde 2. 0.2 mj2 of piperidine was added to a solution of 1 g dissolved in 80 ml anhydrous benzene, a Dean-Stark trap was attached, and after refluxing for 6 hours, the solvent was distilled off under reduced pressure.
The residue was crystallized by adding ethyl acetate and isopropyl ether, and recrystallized using ethyl acetate to give a melting point of 137-1.
1.7 g of yellow crystals at 38°C were obtained. As a result of the split, the main island is
1-(5-chlorothiene-2-
yl)-2-(Ill-imidazolyl")-3-(4
-Chlorophenyl)-2-propen-1-one was recognized, and the yield was 32%.

（分析結果） 元素分析（ＣＩ６ＨＩ。Ｎ２０ＳＣＩ□として、％）分
析値　Ｃ：５５．３０　、Ｈ：２．６６、Ｎ：８．２９
計算値　Ｃ：５５．０３　、旧２．８９、Ｎ：８．０２
ＬＣ Ｒｆ　：０．８０　（酢酸エチル：アセトン＝　５　：
１）Ｒｆ　：０．７９　（クロロホルム：メタノール＝
ｌＯ：１） 実施例３ 本発明化合物について、病原真菌に対する最小発育阻止
濃度を測定したところ、その試験結果は次表のとおりで
あった。(Analysis results) Elemental analysis (CI6HI.N20SCI□, %) Analysis values C: 55.30, H: 2.66, N: 8.29
Calculated value C: 55.03, old 2.89, N: 8.02
LC Rf: 0.80 (ethyl acetate: acetone = 5:
1) Rf: 0.79 (chloroform:methanol=
IO: 1) Example 3 The minimum inhibitory concentration against pathogenic fungi was measured for the compound of the present invention, and the test results were as shown in the following table.

なお、表中の数値はμｇ７ｍｌ！である。In addition, the numbers in the table are μg7ml! It is.

Claims (2)

【特許請求の範囲】[Claims] （１）一般式； ▲数式、化学式、表等があります▼ （但し、式中Ｒ＿１及びＲ＿２は水素原子または塩素原
子であり、少なくとも１つは塩素原子を表す。）で示さ
れるイミダゾール化合物。(1) General formula; ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (However, in the formula, R_1 and R_2 are hydrogen atoms or chlorine atoms, and at least one represents a chlorine atom.) Imidazole compound represented by the following. （２）構造式 ▲数式、化学式、表等があります▼ で示される１−（５−クロロチエン−２−イル）−２−
（１Ｈ−イミダゾリル）エタノンと下記一般式で示され
るベンズアルデヒド化合物 一般式 （但し、式中Ｒ＿１及びＲ＿２は水素原子または塩素原
子であり、少なくとも１つは塩素原子を表す。）を反応
させることを特徴とする 一般式 ▲数式、化学式、表等があります▼ （但し、式中Ｒ＿１及びＲ＿２は前記と同じである。）
で示されるイミダゾール化合物の製造方法。(2) 1-(5-chlorothien-2-yl)-2- shown by the structural formula ▲ Numerical formulas, chemical formulas, tables, etc. ▼
(1H-imidazolyl)ethanone is reacted with a benzaldehyde compound represented by the following general formula (wherein R_1 and R_2 are hydrogen atoms or chlorine atoms, and at least one represents a chlorine atom). General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (However, in the formula, R_1 and R_2 are the same as above.)
A method for producing an imidazole compound represented by
JP21432285A 1985-09-26 1985-09-26 Novel imidazole compound and production thereof Granted JPS6272687A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP21432285A JPS6272687A (en) 1985-09-26 1985-09-26 Novel imidazole compound and production thereof
US06/906,432 US4720551A (en) 1985-09-26 1986-09-12 Chlorothienyl-imidazole propenones
EP86307169A EP0218398A3 (en) 1985-09-26 1986-09-17 Imidazole compound valuable as fungicidal agent and process for preparation thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP21432285A JPS6272687A (en) 1985-09-26 1985-09-26 Novel imidazole compound and production thereof

Publications (2)

Publication Number Publication Date
JPS6272687A true JPS6272687A (en) 1987-04-03
JPH0380157B2 JPH0380157B2 (en) 1991-12-24

Family

ID=16653838

Family Applications (1)

Application Number Title Priority Date Filing Date
JP21432285A Granted JPS6272687A (en) 1985-09-26 1985-09-26 Novel imidazole compound and production thereof

Country Status (1)

Country Link
JP (1) JPS6272687A (en)

Also Published As

Publication number Publication date
JPH0380157B2 (en) 1991-12-24

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