KR100361824B1 - Process for preparing 2-aminothiazol carboxamide derivatives useful in killing plant pathogenic bacteria - Google Patents

Process for preparing 2-aminothiazol carboxamide derivatives useful in killing plant pathogenic bacteria Download PDF

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KR100361824B1
KR100361824B1 KR1019940039896A KR19940039896A KR100361824B1 KR 100361824 B1 KR100361824 B1 KR 100361824B1 KR 1019940039896 A KR1019940039896 A KR 1019940039896A KR 19940039896 A KR19940039896 A KR 19940039896A KR 100361824 B1 KR100361824 B1 KR 100361824B1
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methyl
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carboxylic acid
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KR960022514A (en
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류요섭
윤만영
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주식회사 엘지생명과학
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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Abstract

PURPOSE: A process for preparing 2-aminothiazol carboxamide derivatives useful in killing plant pathogenic bacteria is provided, thereby preparing the title compound simply. CONSTITUTION: A process for preparing 2-aminothiazol carboxamide derivatives of the formula(1) useful in killing plant pathogenic bacteria comprises reacting 2-halothiazol carboxamide of the formula(2) with first amine of the formula(3), wherein R1 is C1-C5 alkyl, C1-C5 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, or C3-C6 cycloalkyl; and R2 is C1-C3 alkyl or C1-C3 haloalkyl; the amount of the compound of the formula(3) used is 2 to 3 moles as larger as than the compound of the formula(2).

Description

2-아미노티아졸 카르복사미드 유도체의 제조방법Method for preparing 2-aminothiazole carboxamide derivative

본 발명은 하기 일반식 (1)로 표시되는 2-아미노티아졸 카르복사미드의 제조방법에 관한 것이다.The present invention relates to a method for producing 2-aminothiazole carboxamide represented by the following general formula (1).

상기식에서,In the above formula,

R1은 (C1-C5)알킬기, (C1-C5)할로알킬기, (C3-C6) 알케닐기, (C3-C6)알키닐기, 또는 (C3-C6)시클로알킬이고,R 1 is a (C 1 -C 5 ) alkyl group, (C 1 -C 5 ) haloalkyl group, (C 3 -C 6 ) alkenyl group, (C 3 -C 6 ) alkynyl group, or (C 3 -C 6 ) Cycloalkyl,

R2는 (C1-C3)알킬기 또는 (C1-C3)할로알킬기이다.R 2 is a (C 1 -C 3 ) alkyl group or a (C 1 -C 3 ) haloalkyl group.

상기 일반식 (1)의 화합물들은 식물병원균 퇴치에 유용하며 문헌에 알려지지 않은 신규의 물질로서 본 발명자들에 의해 이미 대한민국 특허출원 제 93-15846호로 출원된 바 있다.The compounds of the general formula (1) are useful for combating phytopathogens and have been previously filed by the present inventors in Korean Patent Application No. 93-15846 as a novel substance not known in the literature.

본 발명은 하기 일반식 (2)로 표시되는 2-할로티아졸카르복사미드와 하기 일반식 (3)의 일차아민을 반응시키는 것을 특징으로 하여 상기 일반식 (1)의 화합물을 제조하는 방법을 제공하는 것이다.The present invention is characterized by reacting 2-halothiazolecarboxamide represented by the following general formula (2) with a primary amine of the following general formula (3) to prepare a compound of the general formula (1) To provide.

상기식에서,In the above formula,

X 는 할로겐 원자이며,X is a halogen atom,

R1및 R2는 전술한 의미와 동일하다.R 1 and R 2 have the same meaning as described above.

본 발명의 방법에 의해 제조될 목적 화합물 (1)에서, R1이 (C1-C3) 알킬기, 알릴기 또는 시클로프로필기이고, R2가 메틸기, 에틸기 또는 크리플루오로에틸기인 화합물이 바람직하다.In the target compound (1) to be produced by the method of the present invention, a compound in which R 1 is a (C 1 -C 3 ) alkyl group, an allyl group or a cyclopropyl group, and R 2 is a methyl group, an ethyl group or a cryofluoroethyl group is preferable. Do.

이하 본 발명의 제조방법을 상세히 설명한다.Hereinafter, the manufacturing method of the present invention will be described in detail.

본 발명에서 목적 화합물인 일반식 (1)의 화합물들은 하기 반응도식 (I)에따라 간단히 제조된다.Compounds of the general formula (1) which are the target compounds in the present invention are simply prepared according to the following scheme (I).

즉, 일반식 (2)의 화합물을 염기 존재하에서 일반식 (3)의 일차아민과 반응시켜 일반식(1)의 목적 화합물을 제조한다. 이 때 사용되는 염기로는 트리에틸아민, 피리딘 같은 유기염기나 탄산수소나트륨, 탄산나트륨, 탄산칼륨 등의 무기염기 또는 반응에 참여하는 일차아민 자체를 과량 (2몰 내지 3몰)으로 사용하여 염기로 사용할 수 있는데, 트리에틸아민 같은 유기염기가 적당하다. 용매로는 디클로로메틸, 1,2-디클로로에탄,클로로포름.사염화탄소 등 알킬할로겐류, 테트라히드로푸란, 디에틸에테르 등의 에테르류, 아세톤, 메틸 에틸케톤 등의 케톤류, 아세토니트릴, 이소부틸니트릴 등의 니트릴류, 디메틸 포름아미드, 디메틸 아세트아미드등의 아미드류를 사용할 수 있으며,그 중 에테르류가 가장 바람직하다.That is, the compound of formula (2) is reacted with the primary amine of formula (3) in the presence of a base to prepare the target compound of formula (1). The base used at this time may be an organic base such as triethylamine or pyridine, an inorganic base such as sodium hydrogen carbonate, sodium carbonate or potassium carbonate, or a primary amine itself participating in the reaction in excess (2 to 3 mol) as a base. Organic bases such as triethylamine are suitable. Examples of the solvent include dichloromethyl, 1,2-dichloroethane, chloroform, alkyl halogens such as carbon tetrachloride, ethers such as tetrahydrofuran and diethyl ether, ketones such as acetone and methyl ethyl ketone, acetonitrile and isobutyl nitrile, and the like. Amides, such as nitriles, dimethyl formamide, and dimethyl acetamide, can be used, of which ethers are most preferred.

본 반응에서 사용되는 일반식 (3)의 일차아밀은 수분을 제거한 후 화합물 (2)에 대하여 2몰 내지 3몰배 사용하는 것이 바람직하다. 반응온도는 상온에서 100℃범위내에서 가능하나 40℃-60℃가 적절하다.The primary amyl of the general formula (3) used in this reaction is preferably used 2 to 3 molar times with respect to the compound (2) after removing water. The reaction temperature is possible in the range of 100 ℃ at room temperature, but 40 ℃-60 ℃ is appropriate.

본 반응에서 출발물질로 사용되는 상기 일반식 (2)의 유도체들은 유럽특허제 313,091 호에 기재된 방법에 의해 다음 반응도식 (II)에 따라 합성할 수 있다.Derivatives of the general formula (2) used as starting materials in this reaction can be synthesized according to the following scheme (II) by the method described in European Patent No. 313,091.

즉,화합물 (7)를 가수분해시켜 화합물 (6)으로 바꾼 뒤, 티오닐클로라이드 (SOCl2) 또는 오염화인 (PCl5)과 함께 디클로로메탄 용매하에 환류시키면서 교반하여 산할로겐화물 (5)을 만든 후 이 산 할로겐화물을 트리에틸아민 염기 존재하에서 α-아미노니트릴 화합물 (4)과 반응시켜 만든다.That is, compound (7) was hydrolyzed to compound (6), and then stirred with reflux in a dichloromethane solvent with thionyl chloride (SOCl 2 ) or phosphorus pentachloride (PCl 5 ) to form an acid halide (5). This acid halide is then made by reacting with the α-aminonitrile compound (4) in the presence of triethylamine base.

화합물 (6)은 J. Heterocyclic chem., 22, 621 (1985)에 기재된 방법에 의해 제조할 수 있다.Compound (6) can be prepared by the method described in J. Heterocyclic chem., 22, 621 (1985).

이하 본 발명을 실시예에 의거 보다 구체적으로 설명한다.Hereinafter, the present invention will be described in more detail with reference to Examples.

제조예 1. 2-브로모-4-메틸-티아졸-5-카르복실산(시아노-티오펜-2-일-메틸)-아미드의 합성Preparation Example 1 Synthesis of 2-bromo-4-methyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl) -amide

2-브로모기-메틸-티아졸-5-카르복실산 1.0g, 오염화인 1.05g을 디클로로메탄30ml에 가하고 1시간 동안 환류시키면서 교반한 후 감압하에서 용매와 포스포러스옥시클로라이드(POCl3)를 제거한 뒤 이를 디클로로메탄 30ml에 다시 녹이고 0℃에서 아미노-티오펜-2-일-아세토니트릴 염산염 0.87g과 트리에틸아민 1.5ml를 가한다. 상온에서 2시간 교반한 후 물을 가하고 유기층을 추출해낸다. 유기층을 분리하여 무수망초로 건조, 증발시키고 실리카겔 컬럼 크로마토그래피로 분리하여 2-브로모-4-메틸-티아졸-5-카르복실산(시아노-티오펜-2-일-메틸)-아미드 1.12g을 얻었다(수율 72%).1.0 g of 2-bromo group-methyl-thiazole-5-carboxylic acid and 1.05 g of phosphorus pentachloride were added to 30 ml of dichloromethane and stirred under reflux for 1 hour, followed by removal of the solvent and phosphorus oxychloride (POCl 3 ) under reduced pressure. Then it was dissolved again in 30 ml of dichloromethane and 0.87 g of amino-thiophen-2-yl-acetonitrile hydrochloride and 1.5 ml of triethylamine were added at 0 ° C. After stirring for 2 hours at room temperature, water is added and the organic layer is extracted. The organic layer was separated, dried over anhydrous forget-me-not, evaporated and separated by silica gel column chromatography, 2-bromo-4-methyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl) -amide 1.12 g was obtained (yield 72%).

제조예 2. 2-브로모-4-트리플루오로메틸-티아졸-5-카르복실산(시아노-티오펜 -2-일-메틸)-아미드의 합성.Preparation Example 2 Synthesis of 2-bromo-4-trifluoromethyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl) -amide

2-브로모-4-트리플루오로메틸-티아졸톤-카르복실산 1.2g을 사용하여 제조예 1과 동일한 방법으로 실시하여 표제 화합물 1.16g을 얻었다(수율 70%).1.2 g of 2-bromo-4-trifluoromethyl-thiazoltone-carboxylic acid was used in the same manner as in Preparation Example 1 to obtain 1.16 g of the title compound (yield 70%).

제조예 3. 2-브로모-4-에틸-티아졸-5-카르복실산(시아노-티오펜-2-일-메틸)-아미드의 합성.Preparation Example 3 Synthesis of 2-bromo-4-ethyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl) -amide

2-브로모-4-에틸-티아졸-5-카르복실산 1.5g을 사용하여 제조예 1 과 동일한 방법으로 실시하여 표제화합물 1.68g을 얻었다(수율 75%).1.5 g of 2-bromo-4-ethyl-thiazole-5-carboxylic acid was used in the same manner as in Preparation Example 1 to obtain 1.68 g of the title compound (yield 75%).

실시예 1. 2-에틸아미노-4-메틸-티아졸-5-카르복실산(시아노-티오펜-2-일-메틸)-아미드의 합성Example 1.Synthesis of 2-ethylamino-4-methyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl) -amide

2-브로모-4-메틸-티아졸-5-카르복실산 (시아노-티오펜-2-일-메틸)-아미드 1.0g과 트리에틸아민 0.41ml, 에틸아민 0.57ml를 테트라히드로푸란 용매 10ml에 가하고 4시간 동안 환류시키면서 교반한 뒤 물과 에틸아세테이트를 가해서 유기층을 추출한다. 분리한 유기층을 무수망초로 건조, 증발시키고 디에틸 에트르에서 재결정하여 0.62g의 표제 화합물을 얻었다(수율 72%).1.0 g of 2-bromo-4-methyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl) -amide, 0.41 ml of triethylamine, and 0.57 ml of ethylamine were dissolved in tetrahydrofuran. After adding to 10ml and stirring under reflux for 4 hours, water and ethyl acetate were added to extract the organic layer. The separated organic layer was dried over anhydrous forget-me-not, evaporated and recrystallized in diethyl ether to give 0.62 g of the title compound (yield 72%).

실시예 2. 2-메틸아미노-4-메틸-티아졸-5-카르복실산(시아노-티오펜-2-일-메틸)-아미드의 합성Example 2. Synthesis of 2-methylamino-4-methyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl) -amide

2-브로모-4-메틸-티아졸-5-카르복실산(시아노-티오펜-2-일-메틸)-아미드 1.0g과 트리에틸아민 0.41ml, 알릴아민 0.61ml를 테트라히드로푸란 용매 10ml에 가하고 4시간 동안 환류시키면서 교반한 뒤 실시예 1 과 동일한 과정을 거쳐 0.65g의 표제화합물을 얻었다(수율 76%).1.0 g of 2-bromo-4-methyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl) -amide, 0.41 ml of triethylamine, and 0.61 ml of allylamine are tetrahydrofuran solvents. After adding to 10ml and stirring under reflux for 4 hours, 0.65 g of the title compound was obtained through the same procedure as in Example 1 (yield 76%).

실시예 3. 2-알릴아미노-4-메틸-티아졸-5-카르복실산(시아노-티오펜-2-일-메틸)-아미드의 합성Example 3. Synthesis of 2-allylamino-4-methyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl) -amide

2-브로모-4-메틸-티아졸-5-카르복실산(시아노-티오펜-2-일-메틸)-아미드 1.0g과 트리에틸아민 0.41ml, 알릴아민 0.67ml를 테트라히드로푸란 용매 10ml에 가하고 12시간 동안 환류시키면서 교반한 뒤 실시예 1 과 동일한 과정을 거쳐 0.51g의 표제 화합물을 얻었다(수율 55%).1.0 g of 2-bromo-4-methyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl) -amide, 0.41 ml of triethylamine, and 0.67 ml of allylamine were tetrahydrofuran solvents. After adding to 10ml and stirring under reflux for 12 hours, 0.51 g of the title compound was obtained through the same procedure as in Example 1 (yield 55%).

실시예 4. 2-시클로프로필아미노-4-메틸-티아졸-5-카르복실산(시아노-티오펜 -2-일-메틸)-아미드의 합성Example 4. Synthesis of 2-cyclopropylamino-4-methyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl) -amide

2-브로모-4-메틸-티아졸-5-카르복실산(시아노-티오펜-2-일-메틸)-아미드 1.0g과 트리에틸아민 0.41ml, 시클로프로필아민 0.64ml를 테트라히드로푸란 용매 10ml에 가하고 10시간 동안 환류시키면서 교반한 뒤 실시예 1 과 동일한 과정을 거쳐 0.49g의 표제 화합물을 얻었다(수율 53%).Tetrahydrofuran was added 1.0 g of 2-bromo-4-methyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl) -amide, 0.41 ml of triethylamine, and 0.64 ml of cyclopropylamine. 0.49 g of the title compound was obtained through the same procedure as in Example 1 after stirring with reflux for 10 hours and reflux for 10 hours (yield 53%).

실시예 5. 2-에틸아미노-4-트리플루오로메틸-티아졸-5-카르복실산(시아노-티오펜-2-일-메틸)-아미드의 합성Example 5. Synthesis of 2-ethylamino-4-trifluoromethyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl) -amide

2-브로모-4-트리를루오로메틸-티아졸-5-카르복실산(시아노-티오펜-2-일-메틸)-아미드 1.0g과 트리에틸아민 0.36ml, 에틸아민 0.5ml를 테트라히드로푸란 용매 10ml에 가하고 4시간 동안 환류시키면서 교반한 뒤 실시예 1과 동일한 과정을 거쳐 0.679의 표제 화합물을 얻었다 (수율 73%).1.0 g of 2-bromo-4-triluoromethyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl) -amide, 0.36 ml of triethylamine, and 0.5 ml of ethylamine 10 ml of tetrahydrofuran solvent was added and stirred under reflux for 4 hours, followed by the same procedure as in Example 1 to obtain 0.679 of the title compound (yield 73%).

실시예 6. 2-에틸아미노-4-에틸-티아졸-5-카르복실산(시아노-티오펜-2-일-메틸)-아미드의 합성Example 6. Synthesis of 2-ethylamino-4-ethyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl) -amide

2-브로모-4-에틸-티아졸-5-카르복실산(시아노-티오펜-2-일-메틸)-아미드 1.0g과 트리에틸아민 0.40ml, 에틸아민 0.55ml를 테트라히드로푸란 용매 10ml에 가하고 4시간 동안 환류시키면서 교반한 뒤 실시예 1 과 동일한 과정을 거쳐 0.63g의 표제 화합물을 얻었다(수율 70%).1.0 g of 2-bromo-4-ethyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl) -amide, 0.40 ml of triethylamine, and 0.55 ml of ethylamine were dissolved in tetrahydrofuran. After stirring to reflux for 4 hours to 10ml to give 0.63g of the title compound in the same procedure as in Example 1 (yield 70%).

실시예 7. 2-메틸아미노-4-에틸-티아졸-5-카르복실산(시아노-티오펜-2-일-메틸)-아미드의 합성Example 7. Synthesis of 2-methylamino-4-ethyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl) -amide

2-브로모-4-에틸-티아졸-5-카르복실산(시아노-티오펜-2-일-메틸)-아미드 1.0g과 트리에틸아민 0.41ml, 에틸아민 0.58ml를 테트라히드로푸란 용매 10ml에 가하고 4시간 동안 환류시키면서 교반한 뒤 실시예 1 과 동일한 과정을 거쳐 0.77g의 표제 화합물을 얻었다(수율 89%).1.0 g of 2-bromo-4-ethyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl) -amide, 0.41 ml of triethylamine, and 0.58 ml of ethylamine were dissolved in tetrahydrofuran. 0.7 ml of the title compound was obtained through the same procedure as in Example 1 after stirring with reflux for 4 hours and reflux for 4 hours (yield 89%).

실시예 8. 2-알릴아미노-4-에틸-티아졸-5-카르복실산(시아노-티오펜-2-일-메틸)-아미드의 합성Example 8. Synthesis of 2-allylamino-4-ethyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl) -amide

2-브로모-4-에틸-티아졸-5-카르복실산(시아노-티오펜-2-일-메틸)-아미드 1.0g과 트리에틸아민 0.40ml, 에틸아민 0.66ml를 테트라히드로푸란 용매 10ml에 가하고 12시간 동안 환류시키면서 교반한 뒤 실시예 1 과 동일한 과정을 거쳐 0.57g의 표제 화합물을 얻었다(수율 61%).1.0 g of 2-bromo-4-ethyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl) -amide, 0.40 ml of triethylamine, and 0.66 ml of ethylamine were dissolved in tetrahydrofuran. After stirring to reflux for 12 hours to reflux for 12 hours to give 0.57g of the title compound in the same manner as in Example 1 (61% yield).

실시예 9. 2-시클로프로필아미노-4-에틸-티아졸-5-카르복실산(시아노-티오펜 -2-일-메틸)-아미드의 합성Example 9 Synthesis of 2-cyclopropylamino-4-ethyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl) -amide

2-브로모-4-에틸-티아졸-5-카르복실산 (시아노-티오펜-2-일-메틸)-아미드 1.0g과 트리에틸아민 0.40ml, 에틸아민 0.60ml를 테트라히드로푸란 용매 10ml에 가하고 12시간 동안 환류시키면서 교반한 뒤 실시예 1 과 동일한 과정을 거쳐 0.56g의 표제 화합물을 얻었다(수율 60%).1.0 g of 2-bromo-4-ethyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl) -amide, 0.40 ml of triethylamine, and 0.60 ml of ethylamine were dissolved in tetrahydrofuran. After adding to 10ml and stirring under reflux for 12 hours, 0.56 g of the title compound was obtained through the same procedure as in Example 1 (yield 60%).

실시예 10. 4-메틸-2-(프로프-2-이닐아미노)-티아졸-5-카르복실산(시아노-티오펜-2-일-메틸)-아미드의 합성Example 10 Synthesis of 4-methyl-2- (prop-2-ynylamino) -thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl) -amide

2-브로모-4-메틸-티아졸-5-카르복실산 (시아노-티오펜-2-일-메틸)-아미드 1.2g과 트리에틸아민 0.48ml, 프로파질아민 0.50ml를 테트라히드로푸란 용매 10ml에 가하고 18시간 동안 환류시키면서 교반한 뒤 실시예 1 과 동일한 과정을 거쳐 0.61g의 표제 화합물을 얻었다(수율 56%).Tetrahydrofuran was added 1.2 g of 2-bromo-4-methyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl) -amide, 0.48 ml of triethylamine, and 0.50 ml of propazylamine. After adding to 10 ml of solvent and stirring under reflux for 18 hours, the same procedure as in Example 1 was carried out to obtain 0.61 g of the title compound (yield 56%).

Claims (3)

하기 일반식 (2)로 표시되는 2-할로티아졸 카르복사미드를 하기 일반식 (3)으로 표시되는 일차아민과 반응시키는 것을 특징으로 하는 하기 일반식 (1)로 표시되는 2-아미노티아졸 카르복사미드 유도체의 제조방법:2-halothiazole carboxamide represented by the following general formula (2) is reacted with a primary amine represented by the following general formula (3): 2-aminothiazole represented by the following general formula (1) Process for preparing carboxamide derivatives: 상기식에서,In the above formula, R1은 (C1-C5)알킬기, (C1-C5)할로알킬기, (C3-C6)알케닐기, (C3-C6)알키닐기 또는 (C3-C6)시클로알킬이고,R 1 is a (C 1 -C 5 ) alkyl group, (C 1 -C 5 ) haloalkyl group, (C 3 -C 6 ) alkenyl group, (C 3 -C 6 ) alkynyl group or (C 3 -C 6 ) cyclo Alkyl, R2는 (C1-C3)알킬기 또는 (C1-C3)할로알킬기이다.R 2 is a (C 1 -C 3 ) alkyl group or a (C 1 -C 3 ) haloalkyl group. 제 1 항에 있어서,The method of claim 1, R1은 (C1-C3)알킬기, 알릴기 또는 시클로프로필기이고,R 1 is a (C 1 -C 3 ) alkyl group, an allyl group or a cyclopropyl group, R2는 메틸기, 에틸기 또는 트리플루오로메틸기임을 특징으로 하는 일반식 (1)의 화합물의 제조방법.R 2 is a methyl, ethyl or trifluoromethyl group, the process for producing a compound of formula (1). 제 1 항에 있어서 일반식 (3)의 화합물의 사용량이 일반식 (2)의 화합물에 대해 2 몰 내지 3몰배임을 특징으로 하는 제조방법.The production method according to claim 1, wherein the amount of the compound of the general formula (3) is 2 to 3 mol times based on the compound of the general formula (2).
KR1019940039896A 1994-12-30 1994-12-30 Process for preparing 2-aminothiazol carboxamide derivatives useful in killing plant pathogenic bacteria KR100361824B1 (en)

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