KR970065536A - Novel 2- (piperazin-1-yl) thiazole-4-carboxylic acid derivatives, processes for their preparation and their use for the control of plant pathogens - Google Patents

Novel 2- (piperazin-1-yl) thiazole-4-carboxylic acid derivatives, processes for their preparation and their use for the control of plant pathogens Download PDF

Info

Publication number
KR970065536A
KR970065536A KR1019960005597A KR19960005597A KR970065536A KR 970065536 A KR970065536 A KR 970065536A KR 1019960005597 A KR1019960005597 A KR 1019960005597A KR 19960005597 A KR19960005597 A KR 19960005597A KR 970065536 A KR970065536 A KR 970065536A
Authority
KR
South Korea
Prior art keywords
general formula
alkyl
compound represented
haloalkyl
methyl
Prior art date
Application number
KR1019960005597A
Other languages
Korean (ko)
Other versions
KR0163290B1 (en
Inventor
김문정
김성기
편승엽
전재훈
류요섭
유성훈
최우봉
전성욱
전삼재
이성백
박현철
조진호
Original Assignee
성재갑
주식회사 Lg 화학
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 성재갑, 주식회사 Lg 화학 filed Critical 성재갑
Priority to KR1019960005597A priority Critical patent/KR0163290B1/en
Publication of KR970065536A publication Critical patent/KR970065536A/en
Application granted granted Critical
Publication of KR0163290B1 publication Critical patent/KR0163290B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements

Abstract

본 발명은 식물병원균 퇴치에 뛰어난 효과를 갖는 하기 일반식(Ⅰ)로 표시되는 신규2-(피페라진-1-일)티아졸-4-카르복실산 유도체 및 그의 제조방법에 관한 것이다.The present invention relates to a novel 2- (piperazin-1-yl) thiazole-4-carboxylic acid derivative represented by the following general formula (I) which has an excellent effect on the elimination of plant pathogenic bacteria and a process for producing the same.

상기 식에서 R1은 할로겐, C1-C3알킬, C1-C3힐로알킬, C1-C3알콕시 또는 C1-C3알킬캬르보닐에 의해 1 또는 2치환되거나 비치환된 페닐, 포르밀, C1-C3알콕시카르보닐, C1-C3알킬, C1-C3알킬설포닐기를 나타내고, R2는 C1-C5알킬, C1-C3할로알킬 또는 C1-C3알콕시메틸을 나타내며, R3는 수소, 메틸 또는 에틸을 나타낸다.Wherein R 1 is phenyl, monosubstituted or disubstituted by halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy or C 1 -C 3 alkylcarbonyl, C 1 -C 3 alkoxycarbonyl, C 1 -C 3 alkyl, C 1 -C 3 alkylsulfonyl group, R 2 represents C 1 -C 5 alkyl, C 1 -C 3 haloalkyl or C 1 -C 3 haloalkyl, C 3 alkoxymethyl, and R 3 represents hydrogen, methyl or ethyl.

Description

신규 2-(피페라진-1-일)티아졸-4-카르복실산 유도체, 그의 제조방법 및 식물병원균 퇴치를 위한 그의 용도Novel 2- (piperazin-1-yl) thiazole-4-carboxylic acid derivatives, processes for their preparation and their use for the control of plant pathogens

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is a trivial issue, I did not include the contents of the text.

Claims (8)

하기 일반식(Ⅰ)의 2-(피페라진-1-일)-티아졸-4-카르복실산 유도체.2- (Piperazin-1-yl) -thiazole-4-carboxylic acid derivatives of the general formula (I) 상기 식에서 R1은 할로겐, C1-C3알킬, C1-C3할로알킬, C1-C3알콕시, 또는 C1-C3알킬카르보닐에 의해 1 또는 2치환되거나 비치환된 페닐, 포르필, C1-C3알폭시카르보닐, C1-C3알킬, C1-C3알킬설포닐기를 나타내고, R2는 C1-C5알킬, C1-C3할로알킬 또는 C1-C3알콕시메틸을 나타내며, R3는 수소, 메틸 또는 에틸을 나타낸다.Wherein R 1 is phenyl, monosubstituted or disubstituted by halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, or C 1 -C 3 alkylcarbonyl, PORT field, C 1 -C 3 Al propoxy-carbonyl, C 1 -C 3 alkyl, C 1 -C 3 alkyl sulfonic represents a sulfonyl, R 2 is C 1 -C 5 alkyl, C 1 -C 3 haloalkyl or C 1 to 3 alkoxymethyl, and R 3 represents hydrogen, methyl or ethyl. 하기 일반식(Ⅱ)의 화합물을 용매존재하에 하기 일반식 (Ⅲ)의 화합물과 반응시켜 하기 일반식(Ⅰ-1)의 화합물을 제조하는 방법.A process for producing a compound represented by the following general formula (I-1) by reacting a compound represented by the following general formula (II) with a compound represented by the following general formula (III) in the presence of a solvent. 상기 식에서, R1은 할로겐, C1-C3알킬, C1-C3할로알킬, C1-C3알콕시, 또는 C1-C3알킬카르보닐에 의해 1 또는 2치환되거나 비치환된 페닐, 포르밀, C1-C3알콕시카르보닐, C1-C3알킬, C1-C3알킬설포닐기를 나타내고, R2는 C1-C5알킬, C1-C3할로알킬 또는 C1-C3알콕시메틸을 나타내며, R3′는 메틸 또는 에틸을 나타낸다.Wherein R 1 is phenyl which is mono- or disubstituted or unsubstituted by halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, or C 1 -C 3 alkylcarbonyl. , C 1 -C 3 alkoxycarbonyl, C 1 -C 3 alkyl, C 1 -C 3 alkylsulfonyl group, R 2 represents C 1 -C 5 alkyl, C 1 -C 3 haloalkyl or C 1 -C 3 alkoxymethyl, and R 3 'represents methyl or ethyl. 제2항에 있어서, 용매가 디에틸에티르, 테트라하이드로푸란, 디메톡시에탄, 아세톤, 메틸에틸케톤, 이소부틸메틸케톤, 디메틸포름아미드, 디메틸아세트아미드, 디클로로메탄, 1,2-디클로로에탄, 아세토니트릴, 프로피오니트릴, 부티로니트릴, 디메틸설폭사이드 중에서 선택된 1종 이상인 방법.The process according to claim 2, wherein the solvent is selected from the group consisting of diethyl ether, tetrahydrofuran, dimethoxyethane, acetone, methyl ethyl ketone, isobutyl methyl ketone, dimethyl formamide, dimethylacetamide, dichloromethane, Acetonitrile, propionitrile, butyronitrile, and dimethyl sulfoxide. 제2항에 있어서, 추가로 염기 존재하에 반응을 수행하거나, 일반식(Ⅲ)의 헤테로환 2차 아민을 과량으로 사용하는 방법.The method according to claim 2, wherein the reaction is further carried out in the presence of a base, or a heterocyclic secondary amine represented by the general formula (III) is used in excess. 제4항에 있어서, 염기가 트리에틸아미, 피리딘, 탄산수소나트륨, 탄산나트륨, 탄산칼륨 중에서 선택된 1종 이상인 방법.5. The method according to claim 4, wherein the base is at least one selected from the group consisting of triethylamine, pyridine, sodium hydrogencarbonate, sodium carbonate, and potassium carbonate. 제4항에 있어서, 일반식 (Ⅲ)의 헤테로환 2차 아민을 일반식 (Ⅱ)의 화합물에 대해 2 내지 3당량을 사용하는 방법.The method according to claim 4, wherein the heterocyclic secondary amine represented by the general formula (III) is used in an amount of 2 to 3 equivalents based on the compound represented by the general formula (II). 제2항의 방법에 따라 제조된 일반식 (Ⅰ-1) 화합물을 염기 존재하에 가수분해시켜 하기 일반식 (Ⅰ-2)의 화합물을 제조하는 방법.A process for producing a compound represented by the general formula (I-2) by hydrolyzing a compound represented by the general formula (I-1) according to the process of claim 2 in the presence of a base. 상기 식에서, R1및 R2는 제2항에서 정의한 바와 같다.Wherein R 1 and R 2 are as defined in claim 2. 제1항에 정의된 일반식(I)의 화합물을 유효성분으로 함유함을 특징으로 하는 식물병원균 퇴치용 조성물.A composition for combating plant pathogens, which comprises the compound of formula (I) as defined in claim 1 as an active ingredient. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: It is disclosed by the contents of the first application.
KR1019960005597A 1996-03-04 1996-03-04 Novel 2-(piperazin-1-yl)thiazole-4-carboxylic acid derivative, process for preparation thereof and use thereof for controlling phytopathogenic organism KR0163290B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1019960005597A KR0163290B1 (en) 1996-03-04 1996-03-04 Novel 2-(piperazin-1-yl)thiazole-4-carboxylic acid derivative, process for preparation thereof and use thereof for controlling phytopathogenic organism

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1019960005597A KR0163290B1 (en) 1996-03-04 1996-03-04 Novel 2-(piperazin-1-yl)thiazole-4-carboxylic acid derivative, process for preparation thereof and use thereof for controlling phytopathogenic organism

Publications (2)

Publication Number Publication Date
KR970065536A true KR970065536A (en) 1997-10-13
KR0163290B1 KR0163290B1 (en) 1998-12-01

Family

ID=19452382

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019960005597A KR0163290B1 (en) 1996-03-04 1996-03-04 Novel 2-(piperazin-1-yl)thiazole-4-carboxylic acid derivative, process for preparation thereof and use thereof for controlling phytopathogenic organism

Country Status (1)

Country Link
KR (1) KR0163290B1 (en)

Also Published As

Publication number Publication date
KR0163290B1 (en) 1998-12-01

Similar Documents

Publication Publication Date Title
FI901030A0 (en) Process for the preparation of therapeutically active 2- (1-piperazinyl) -4-phenylcycloalkanopyridine derivatives
DK0446913T3 (en) Process for the preparation of chlorothiazole derivatives.
ES2170080T3 (en) DERIVATIVES OF 2- (1- (1,3-TIAZOLIN-2-IL) AZETIDIN-3-IL) TIO-CARBAPENEM.
FI904602A0 (en) PYRAZOLODERIVAT, FOERFARANDE FOER DERAS FRAMSTAELLNING OCH DESSA INNEHAOLLANDE PHARMACEUTICAL BLANDNINGAR.
KR870002127A (en) Process for preparing nitromethylene derivative
KR840003618A (en) Method for preparing 2-cyanobenz imidazole derivative
KR920700202A (en) Acryloyl substituted pyrrole derivatives
KR860008976A (en) 2- (4-benzoyl-1-piperidyl) -1-phenylalkanol derivative
KR880002829A (en) Dihydropyridine anti-allergic and anti-inflammatory agents
NO20071311L (en) Process for the preparation of citalopram
ES504251A0 (en) PROCEDURE FOR THE PREPARATION OF ARYLAMINE DERIVATIVES
KR860002485A (en) Method for preparing acylated saccharin derivative
KR970065536A (en) Novel 2- (piperazin-1-yl) thiazole-4-carboxylic acid derivatives, processes for their preparation and their use for the control of plant pathogens
KR880003932A (en) Heterocyclic Compounds, Preparations and Uses thereof
HU212611B (en) Process for the preparation of 2-substituted 4,6-dialkoxy-pyrimidine derivatives
KR940005570A (en) Method for preparing pyrrolidinylacetamide derivative
KR920012100A (en) Bisphosphonic acid derivatives, their preparation and uses
NO20002315L (en) Novel 1-aza-2-alkyl-6-aryl-cycloalkane compounds, process for their preparation and pharmaceutical compositions containing them
SE9402596D0 (en) Carboxymethylidene cycloheptimidazole derivatives, process for their preparation and therapeutic agents containing them
DK0478390T3 (en) Process for the preparation of 4-methylsulfonylbenzoic acid derivatives and intermediates
KR970065537A (en) Novel 2-aminothiazole carboxamide derivative and method for producing the same
FR2369252A1 (en) Di:fluoroalkyl- and di:fluoro:aralkyl-benzene derivs. - used as stable intermediates for pharmaceuticals
PE20000479A1 (en) MORPHOLINE ETHERS
KR920021496A (en) Amide derivatives, preparation method thereof and compositions for inhibiting pests
DK2264019T3 (en) Intermediate compounds for the preparation of taxane derivatives

Legal Events

Date Code Title Description
A201 Request for examination
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20060616

Year of fee payment: 9

LAPS Lapse due to unpaid annual fee