KR970703306A - Carbamoyl Carboxylic Acid Hydrazides and Their Use Against Fungi - Google Patents

Carbamoyl Carboxylic Acid Hydrazides and Their Use Against Fungi

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Publication number
KR970703306A
KR970703306A KR1019960706896A KR19960706896A KR970703306A KR 970703306 A KR970703306 A KR 970703306A KR 1019960706896 A KR1019960706896 A KR 1019960706896A KR 19960706896 A KR19960706896 A KR 19960706896A KR 970703306 A KR970703306 A KR 970703306A
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alkyl
aryl
group
alkoxy
haloalkoxy
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KR1019960706896A
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Korean (ko)
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올리버 바그너
프랑크 베테리히
칼 아익켄
에버하르트 암머만
기젤라 로렌쯔
토마스 뮐러
죤-브라이언 스피이크만
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슈타르크, 카르크
바스프 악티엔게젤샤프트
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Priority claimed from DE4419516A external-priority patent/DE4419516A1/en
Priority claimed from DE1995104423 external-priority patent/DE19504423A1/en
Application filed by 슈타르크, 카르크, 바스프 악티엔게젤샤프트 filed Critical 슈타르크, 카르크
Publication of KR970703306A publication Critical patent/KR970703306A/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
    • C07C271/42—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/54—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/22—O-Aryl or S-Aryl esters thereof
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C243/34—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a carbon skeleton further substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/60—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups having oxygen atoms of carbamate groups bound to nitrogen atoms

Abstract

본 발명은 화학식(I)의 카르바모일카르브히드라지드(I)의 화합물 및 이들의 염 및 이들의 제조 방법, 이들을 함유하는 조성물, 이들의 용도 및 중간체(IV)에 관한 것이다.The present invention relates to compounds of carbamoylcarbhydrazide (I) of formula (I) and salts thereof and methods for their preparation, compositions containing them, their use and intermediates (IV).

상기 식에서, R1은 비치환 또는 치환된 알킬, 알케닐, 알키닐, 시클로알킬, 시클로알케닐, 아릴 또는 헤테로아릴이거나 비치환 또는 치환된 비-방향족 카르보- 또는 베테로사이클, W1W2C=N-(여기서, W1은 비치환 또는 치환된 알킬, 알케닐, 알키닐, 시클로알킬, 시클로알케닐, 아릴 또는 헤테로아릴이고 W2는 수소 또는 W1임)이고; R2는 수소 또는 할로젠화 또는 할로겐화된 알킬 또는 시클로알킬이고; R3은 비치환 또는 치환된 알킬, 시클로알킬 또는 페닐알킬이고; R3는 수소 또는 라디칼 R3중 하나이거나, R3및 R4는 이들이 결합되어 있는 C원자와 함께, 비치환 또는 치환된 포화 카르보- 또는 헤테로사이클이고; R5는 라디칼 R2중 하나이고; R6는 비치환 또는 치환원 알킬, 알케닐. 알키닐, 시클로알킬, 시클로알케닐, 아릴 또는 헤테로아릴, 비치환 또는 치환된 비-방향촉 카르보- 또는 헤테로사이클이거나, R3이 수소인 경우, 이소프로필이고; R7은 수소를 제외한, 라디칼 R6이고, X1, X2, X3은 각 경우 산소 또는 황이고; 화학식(IV)에서 X3은 산소이고 R3은 CH(CH3)2, CH2CH(CH3), CH2CH(CH3)2또는 CH(CH3)C2H5이다.Wherein R 1 is unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heteroaryl or unsubstituted or substituted non-aromatic carbo- or heterocycle, W 1 W 2 C═N—, wherein W 1 is unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heteroaryl and W 2 is hydrogen or W 1 ; R 2 is hydrogen or halogenated or halogenated alkyl or cycloalkyl; R 3 is unsubstituted or substituted alkyl, cycloalkyl or phenylalkyl; R 3 is either hydrogen or the radical R 3 , or R 3 and R 4 are unsubstituted or substituted saturated carbo- or heterocycle with the C atom to which they are attached; R 5 is one of the radicals R 2 ; R 6 is unsubstituted or substituted alkyl, alkenyl. Alkynyl, cycloalkyl, cycloalkenyl, aryl or heteroaryl, unsubstituted or substituted non-aromatic carbo- or heterocycle, or isopropyl when R 3 is hydrogen; R 7 is radical R 6 excluding hydrogen and X 1 , X 2 , X 3 are in each case oxygen or sulfur; In formula (IV) X 3 is oxygen and R 3 is CH (CH 3 ) 2 , CH 2 CH (CH 3 ), CH 2 CH (CH 3 ) 2 or CH (CH 3 ) C 2 H 5 .

Description

카르바모일 카르복실산 히드라지드 및 진균류에 대한 이들의 용도(Carbamoyl Carboxylic Acid Hydrazides and Their Use Against Fungi)Carbamoyl Carboxylic Acid Hydrazides and Their Use Against Fungi

[도면의 간단한 설명][Brief Description of Drawings]

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (9)

화학식(I)의 카르바모일카르보히드라지드 또는 이의 염.Carbamoylcarbohydrazide of formula (I) or a salt thereof. 상기 식에서, R1은 C1-C8-알킬, C2-C8-알케닐 또는 C2-C8-알키닐 (이들은 부분적으로 또는 완전히 할로겐화되고(되거나) 시아노, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, C1-C4-알콕시카르보닐, C3-C7-시클로알킬, C3-C7-시클로알케닐, 아릴, 아릴옥시 및 헤테로아릴로 이루어진 군으로부터 선택된 기를 1 내지 3개 포함할 수 있으며, 이들 중에서 시클릭 라디칼의 경우에는 할로겐, 시아노, C1-C4-알킬, C1-C4-알콕시알킬, C1-C4-할로알킬. C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, C1-C4-알콕시카르보닐, 아릴, 아릴옥시 및 헤테로아릴로 이루어진 군으로부터 선택된 치환체 1 내지 3개를 포함할 수 있음); C3-C7-시클로알킬 또는 C3-C7-시클로알케닐 (이들은 부분적으로 또는 완전히 할로겐화되고(되거나) 시아노, C1-C4-알킬, C1-C4-알콕시알킬, C1-C4-할로알킬, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, C1-C4-알콕시카르보닐, 아릴, 아릴옥시 및 아릴-(C1-C4)-알킬로 이루어진 군으로부터 선택된 기를 1 내지 3개 포함할 수 있으며, 이들 중에서 시클릭기의 경우 할로겐, 시아노, C1-C4-알킬, C1-C4-알콕시알킬, C1-C4-할로알킬, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, C1-C4-알콕시카르보닐, 아릴 및 아릴옥시 이루어진 군으로부터 선택된 치환체 1 내지 3개의 포함할 수 있음); 비-방향족 4- 내지 8-원환(이들은 환원소로서, 탄소 이외에 산소, 황 및 질소로부터 선택된 헤테로원자 1 또는 2개를 함유할 수 있으며, 여기에서 환중의 탄소원자의 경우 할로겐, 시아노, C1-C4-알킬, C1-C4-알콕시알킬, C1-C4-할로알킬, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, C1-C4-알콕시카르보닐, 아릴 및 아릴옥시로 이루어진 군으로부터 선택된 기를 1 또는 2개의 포함할 수 있으며, 환중의 헤테로 원자로서 제2 및 각각의 추가 질소 원자는 수소 또는 C1-C4-알킬기를 포함함); 아릴 또는 헤테로아릴(이들은 할로겐, 시아노, C1-C4-알킬, C1-C4-알콕시알킬, C1-C4-할로알킬, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, C1-C4-알콕시카르보닐, 아릴, 아릴옥시 및 헤테로아릴로 이루어진 군으로 부터 선택된 치환체 1 내지 3개를 포함할 수 있으며, 이들 중에서 시클릭 치환체의 경우에는 할로겐, 시아노, C1-C4-알킬, C1-C4-알콕시알킬, C1-C4-할로알킬, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오 및 C1-C4-알콕시카르보닐로 이루어진 군으로부터 선택된 치환체 1 내지 3개를 포함할 수 있음); 또는 W1W2C=N-[여기서, W1은 C1-C8-알킬 (이는 부분적으로 또는 완전히 할로겐화되고(되거나) 시아노, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, 아릴, 알릴옥시 및 헤테로아릴로 이루어진 군으로부터 선택된 기를 1 내지 3개를 포함할 수 있으며, 이들 중에서 시클릭기의 경우에는 할로겐, 시아노, C1-C4-알킬, C1-C4-알콕시알킬, C1-C4-할로알킬, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, C1-C4-알콕시카르보닐, 아릴 및 아릴옥시로 이루어진 군으로부터 선택된 치환체 1 내지 3개을 포함할 수 있음); C2-C8-알케닐 또는 C2-C8-알키닐(이들은 부분적으로 또는 완전히 할로겐화되고(되거나) 시아노, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, C1-C4-알콕시카르보닐, 아릴 및 아릴옥시로 이루어진 군으로부터 선택된 기를 1 내지 3개 포함할 수 있으며, 이들 중에서 시클릭기의 경우에는 할로겐, 시아노, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, C1-C4-알콕시카르보닐, 아릴 및 아릴옥시로 이루어진 군으로부터 선택된 치환체 1 내지 3개를 포함할 수 있음); C3-C7시클로알킬 또는 C3-C7-시클로알케닐 (이들은 할로겐, 시아노, C1-C4-알킬, C1-C4-알콕시알킬, C1-C4-할로알킬, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, C1-C4-알콕시카르보닐, 아릴 및 아릴-(C1-C4)-알킬로 이루어진 군으로부터 선택된 기를 1 내지 3개 포함할 수 있으며, 여기에서 아릴을 함유하는 기의 경우에는 할로겐, 시아노, C1-C4-알킬, C1-C4-알콕시알킬, C1-C4-할로알킬, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, C1-C4-알콕시카르보닐, 아릴 및 아릴옥시로 이루어진 군으로부터 선택된 치환체 1 내지 3개를 포함할 수 있음); 또는 아릴 또는 헤테로아릴(이들은 할로겐, 시아노, C1-C4-알킬, C1-C4-알콕시알킬, C1-C4-할로알킬, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, C1-C4-알콕시카르보닐, 아릴 및 아릴옥시로 이루어진 군으로부터 선택된 치환체 1 내지 3개를 포함할 수 있음)이고, W2는 수소 또는 W1기 중 하나임]이고; R2는 수소이거나 부분적으로 또는 완전히 할로겐화될 수 있는 C1-C8-알킬 또는 C3-C7-시클로알킬이고; R3은 C1-C8-알킬(이는 할로겐, 시아노, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오 및 C1-C4-알콕시카르보닐 중 1 내지 3개의 기를 포함할 수 있음), C3-C7-시클로알킬 또는 페닐-(C1-C4)-알킬 (이들기의 고리는 할로겐, 시아노, C1-C4-알킬, C1-C4-알콕시알킬, C1-C4-할로알킬, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, C1-C4-알콕시카르보닐, 아릴 및 아릴옥시 중 1 내지 3개의 기를 포함할 수 있음)이고; R4는 수소 또는 라디칼 R3중 하나 이거나 R3및 R4는 이들이 결합되어 있는 C원자와 함께 4- 내지 5-원환 (이들은 환원소로서 탄소 이외에 산소, 황 및 질소로부터 선택된 헤테로원자 1 또는 2개를 함유할 수 있으며, 여기서 환중의 탄소 원자의 경우에는 할로겐, 시아노, C1-C4-알킬, C1-C4-알콕시알킬, C1-C4-할로알킬, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, C1-C4-알콕시카르보닐, 아릴 및 아릴옥시로 이루어진 군으로부터 선택된 기를 1 또는 2개를 포함할 수 있으며, 헤테로원자로서 질소는 수소 또는 C1-C4-알킬기를 포함할 수 있음)이고; R5는 라디칼 R2중 하나이고; R6은 C1-C8-알킬, C2-C8-알케닐 또는 C2-C8-알키닐 (이들은 부분적으로 또는 완전히 할로겐화되고(되거나) 시아노, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, C3-C7-시클로알킬, C3-C7-시클로알케닐, 아릴, 아릴옥시 및 헤테로아릴로 이루어진 군으로부터 선택된 기를 1 내지 3개 포함할 수 있으며, 이들 중에서 시클릭 라디칼의 경우에는 할로겐, 시아노, C1-C4-알킬, C1-C4-알콕시알킬, C1-C4-할로알킬, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, 아릴, 아릴옥시 및 헤테로아릴로 이루어진 군으로부터 선택된 치환체 1 내지 3개를 포함할 수 있음), C3-C7-시클로알킬 또는 C3-C7-시클로알케닐(이들은 부분적으로 또는 완전히 할로겐화되고(되거나) 시아노, C1-C4-알킬, C1-C4-알콕시알킬, C1-C4-할로알킬, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, 아릴, 아릴옥시 및 아릴-(C1-C4)-알킬로 이루어진 군으로부터 선택된 기를 1 내지 3개를 포함할 수 있으며, 이들 중에서 시클릭기의 경우에는 할로겐, 시아노, C1-C4-알킬, C1-C4-알콕시알킬, C1-C4-할로알킬, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, 아릴 및 아릴옥시로 이루어진 군으로부터 선택된 치환체 1 내지 3개를 포함할 수 있음), 비-방향족 4- 내지 8-원환(이들은 환원소로서, 탄소 이외에 산소, 황 및 질소로부터 선택된 헤테로원자 1 또는 2개를 함유할 수 있으며, 여기에서 환중의 탄소원자의 경우에는 할로겐, 시아노, C1-C4-알킬, C1-C4-알콕시알킬, C1-C4-할로알킬, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, 아일 및 아릴옥시로 이루어진 군으로부터 선택된 기를 1 또는 2개를 포함할 수 있으며 환중의 헤테로원자로서 제2 및 각각의 추가 질소 원자는 수소 또는 C1-C4-알킬기를 포함함), 아릴 또는 헤테로아릴(이들은 할로겐, 시아노, C1-C4-알킬, C1-C4-알콕시알킬, C1-C4-할로알킬, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, 아릴, 아릴옥시 및 헤테로 아릴로 이루어진 군으로부터 선택된 치환체 1 내지 3개를 포함할 수 있으며, 이들 중에서 시클릭 치환체의 경우에는 할로겐, 시아노, C1-C4-알킬, C1-C4-알콕시알킬, C1-C4-할로알킬, C1-C4-알콕시, C1-C4-할로알콕시 및 C1-C4-알킬티오로 이루어진 군으로부터 선택된 치환체 1 내지 3개를 포함할 수 있음)이거나 R3이 이소프로필인 경우 수소이고; R7은 수소를 제외한, 라디칼 R6중 하나이고; X1은 산소 또는 황이고, X2는 산소 또는 황이고, X3은 산소 또는 황이며; 단, 하기 라디칼의 정의에 따르는 화합물은 제외한다:Ia-d (R1=Ph-CH2; R2=H; R3=CH3, (CH2)2CH3, CH(CH3)2또는 Ph-CH2; R4,R5=H; R6,R7=CH2CH2Cl), Ie-h(R1=C(CH3)3; R2=H; R3=CH3, CH(CH3)2, CH(CH3)CH2CH3, CH2CH(CH3)2또는 Ph-CH2; R4,R5=H; R6,R7=CH2CH2Br), Ii(R1=Ph-CH2; R2=H; R3=CH3; R4,R5=H; R6=CH3; R7=Ph), Ij-k(R1=Ph-CH2; R2=H; R3=CH(CH3)2또는 CH2CH(CH3)2; R4, R5=H; R6, R7=Ph), Il(R1=C(CH3)3; R2=H; R3=CH(CH3)2; R4, R5, R6=H; R7=Ph), Im(R1=Ph-CH2; R2=H; R3=Ph-CH2; R4, R5=H; R6, R7=CH2CH3), In-o(R1=Ph-CH2; R2=H; R3=CH2SCH3또는 CH2CH2SCH3; R4,R5=H; R6,R7=CH2CH2Cl).Wherein R 1 is C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl or C 2 -C 8 -alkynyl, which are partially or fully halogenated and / or cyano, C 1 -C 4 -Alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkoxycarbonyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkenyl, It may comprise 1 to 3 groups selected from the group consisting of aryl, aryloxy and heteroaryl, of which in the case of cyclic radicals halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy alkyl, C 1 -C 4 - haloalkyl, C 1 -C 4 -. alkoxy, C 1 -C 4 - haloalkoxy, C 1 -C 4 - alkylthio, C 1 -C 4 - alkoxycarbonyl, aryl, May include 1 to 3 substituents selected from the group consisting of oxy and heteroaryl); C 3 -C 7 -cycloalkyl or C 3 -C 7 -cycloalkenyl (they are partially or fully halogenated and / or cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxyalkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkoxycarbonyl, aryl, aryloxy and aryl It may comprise 1 to 3 groups selected from the group consisting of-(C 1 -C 4 ) -alkyl, among which in the case of the cyclic group halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -Alkoxyalkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkoxycarbonyl, aryl And aryloxy may include 1 to 3 substituents selected from the group consisting of; Non-aromatic 4- to 8-membered rings (they are reducing elements, which may contain, in addition to carbon, one or two heteroatoms selected from oxygen, sulfur and nitrogen, wherein in the case of carbon atoms in the ring halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxyalkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, It may comprise one or two groups selected from the group consisting of C 1 -C 4 -alkoxycarbonyl, aryl and aryloxy, wherein the second and each additional nitrogen atom as a hetero atom in the ring is hydrogen or C 1 -C 4 An alkyl group); Aryl or heteroaryl (these are halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxyalkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 One to three substituents selected from the group consisting of -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkoxycarbonyl, aryl, aryloxy and heteroaryl, among which Halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxyalkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4- May include 1 to 3 substituents selected from the group consisting of haloalkoxy, C 1 -C 4 -alkylthio and C 1 -C 4 -alkoxycarbonyl); Or W 1 W 2 C═N- [wherein W 1 is C 1 -C 8 -alkyl which is partially or fully halogenated and / or cyano, C 1 -C 4 -alkoxy, C 1 -C 4- It may comprise 1 to 3 groups selected from the group consisting of haloalkoxy, C 1 -C 4 -alkylthio, aryl, allyloxy and heteroaryl, among which in the case of cyclic groups halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxyalkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkoxycarbonyl, aryl and aryloxy may include 1 to 3 substituents selected from the group consisting of; C 2 -C 8 -alkenyl or C 2 -C 8 -alkynyl (they are partially or fully halogenated and / or cyano, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 - alkylthio, C 1 -C 4 - alkoxycarbonyl, aryl and a group selected from the group consisting of oxy may comprise 1 to 3, in the case of a cyclic group when among these include halogen, cyano, C 1 to 3 substituents selected from the group consisting of 1- C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkoxycarbonyl, aryl and aryloxy May include); C 3 -C 7 cycloalkyl or C 3 -C 7 -cycloalkenyl (these are halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxyalkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkoxycarbonyl, aryl and aryl- (C 1 -C 4 ) -alkyl It may comprise 1 to 3 groups selected from the group consisting of, in the case of a group containing aryl, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxyalkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkoxycarbonyl, aryl and aryloxy May include 1 to 3 substituents); Or aryl or heteroaryl (these are halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxyalkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkoxycarbonyl, aryl and aryloxy, which may include 1 to 3 substituents selected from the group consisting of W 2 is hydrogen Or one of W 1 groups; R 2 is hydrogen or C 1 -C 8 -alkyl or C 3 -C 7 -cycloalkyl which can be partially or fully halogenated; R 3 is C 1 -C 8 -alkyl (which is halogen, cyano, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio and C 1 -C 4 -alkoxy May contain 1 to 3 groups of carbonyl), C 3 -C 7 -cycloalkyl or phenyl- (C 1 -C 4 ) -alkyl (the rings of these groups being halogen, cyano, C 1 -C 4 -Alkyl, C 1 -C 4 -alkoxyalkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1- C 4 -alkoxycarbonyl, aryl and aryloxy, which may include one to three groups; R 4 is either hydrogen or the radical R 3 or R 3 and R 4 together with the C atom to which they are attached are 4- to 5-membered rings (they are reducing atoms heteroatoms 1 or 2 selected from oxygen, sulfur and nitrogen in addition to carbon) Dog, wherein in the case of carbon atoms in the ring halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxyalkyl, C 1 -C 4 -haloalkyl, C 1 -C May comprise one or two groups selected from the group consisting of 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkoxycarbonyl, aryl and aryloxy Nitrogen as the heteroatom may include hydrogen or a C 1 -C 4 -alkyl group; R 5 is one of the radicals R 2 ; R 6 is C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl or C 2 -C 8 -alkynyl, which are partially or fully halogenated and / or cyano, C 1 -C 4 -alkoxy, A group selected from the group consisting of C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkenyl, aryl, aryloxy and heteroaryl 1 to 3, in the case of cyclic radicals, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxyalkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 - alkoxy, C 1 -C 4 - haloalkoxy, C 1 -C 4 - alkylthio, aryl, aryloxy, and that may contain one to three substituents selected from the group consisting of a heteroaryl group), C 3 -C 7 -cycloalkyl or C 3 -C 7 -cycloalkenyl, which are partially or fully halogenated and / or cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxyalkyl, C 1- C 4 -haloalkyl, C 1 -C 4 -alkoxy, May comprise 1 to 3 groups selected from the group consisting of C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, aryl, aryloxy and aryl- (C 1 -C 4 ) -alkyl, Among these, in the case of cyclic groups, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxyalkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1- May contain 1 to 3 substituents selected from the group consisting of C 4 -haloalkoxy, C 1 -C 4 -alkylthio, aryl and aryloxy, non-aromatic 4- to 8-membered rings (these are , In addition to carbon, may contain one or two heteroatoms selected from oxygen, sulfur and nitrogen, wherein in the case of carbon atoms in the ring, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy 1 or 2 groups selected from the group consisting of alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, isyl and aryloxy Dog Second and each additional nitrogen atom as a heteroatom in the ring may include hydrogen or a C 1 -C 4 -alkyl group, aryl or heteroaryl (these are halogen, cyano, C 1 -C 4 -alkyl , C 1 -C 4 -alkoxyalkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, aryl, aryloxy and It may include 1 to 3 substituents selected from the group consisting of hetero aryl, Among these, in the case of cyclic substituents, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxyalkyl, C 1 -C 4 - haloalkyl, C 1 -C 4 - alkoxy, C 1 -C 4 - haloalkoxy, and C 1 -C 4 - which may include a substituent 1 to 3 selected from the group consisting of alkylthio), or R When 3 is isopropyl, it is hydrogen; R 7 is one of the radicals R 6 except hydrogen; X 1 is oxygen or sulfur, X 2 is oxygen or sulfur and X 3 is oxygen or sulfur; With the exception of compounds according to the definition of radicals: Ia-d (R 1 = Ph-CH 2 ; R 2 = H; R 3 = CH 3 , (CH 2 ) 2 CH 3 , CH (CH 3 ) 2 Or Ph-CH 2 ; R 4 , R 5 = H; R 6 , R 7 = CH 2 CH 2 Cl), Ie-h (R 1 = C (CH 3 ) 3 ; R 2 = H; R 3 = CH 3 , CH (CH 3 ) 2 , CH (CH 3 ) CH 2 CH 3 , CH 2 CH (CH 3 ) 2 or Ph-CH 2 ; R 4 , R 5 = H; R 6 , R 7 = CH 2 CH 2 Br), Ii (R 1 = Ph-CH 2 ; R 2 = H; R 3 = CH 3 ; R 4 , R 5 = H; R 6 = CH 3 ; R 7 = Ph), Ij-k (R 1 = Ph-CH 2 ; R 2 = H; R 3 = CH (CH 3 ) 2 or CH 2 CH (CH 3 ) 2 ; R 4 , R 5 = H; R 6 , R 7 = Ph), Il ( R 1 = C (CH 3 ) 3 ; R 2 = H; R 3 = CH (CH 3 ) 2 ; R 4 , R 5 , R 6 = H; R 7 = Ph), Im (R 1 = Ph-CH 2 ; R 2 = H; R 3 = Ph-CH 2 ; R 4 , R 5 = H; R 6 , R 7 = CH 2 CH 3 ), In-o (R 1 = Ph-CH 2 ; R 2 = H; R 3 = CH 2 SCH 3 or CH 2 CH 2 SCH 3 ; R 4 , R 5 = H; R 6 , R 7 = CH 2 CH 2 Cl). 화학식(II)의 카르바모일카르보히드라지드를 화학식(III)의 히드라진과 반응시키는 단계, 및 경우에 따라 상기 수득한 화학식(I)의 화합물을 공지된 방법으로 이의 염 중 하나로 전환시키는 단계를 포함하는, 제1항에 청구된 바와 같은 화학식(I)의 카르바모일카르보히드라지드 또는 이들의 염의 제조 방법.Reacting carbamoylcarbohydrazide of formula (II) with hydrazine of formula (III), and optionally converting the compound of formula (I) obtained above into one of its salts in a known manner A process for preparing carbamoylcarbohydrazide of formula (I) or salts thereof, comprising as claimed in claim 1. X1, X2및 X3가 각 경우 산소이고, R-X1-(CO)가 공지된 방법으로 제거할 수 잇는 보호기인, 화학식(I)의 카르바모일카르보히드라지드를 아미노산 히드라지드(IV)로 전화시키는 단계, 및 상기 수득한 아미노산 히드라지드(IV)를 화학식(V)의 클로로포르밀 옥심과 염기의 존재하에서 반응시키는 단계, 및 경우에 따라 상기 수득산 화합물(I)을 공지된 방법으로 이의 염 중 하나로 전환시키는 단계를 포함하는, R1이 W1W2C=N-인 화학식(I)의 카르바모일카르보히드라지드 또는 이들의 염의 제조 방법.Carbamoylcarbohydrazide of formula (I), wherein X 1 , X 2 and X 3 are oxygen in each case and RX 1- (CO) is a protecting group which can be removed by a known method, is used as amino acid hydrazide (IV ) And reacting the obtained amino acid hydrazide (IV) with chloroformyl oxime of formula (V) in the presence of a base, and optionally the obtained acid compound (I) A process for preparing carbamoylcarbohydrazide of formula (I) or salts thereof, wherein R 1 is W 1 W 2 C═N—. R6가 수소인, 제1항에 청구된 바와 같은 화학식(I)의 카르바모일카르보히드라지드를 화학식 R6-X (여기서 R6은 C1-C8-알킬, C4-C7-시클로알킬 또는 아릴-(C1-C4)-알킬이고 X는 네가티브 이탈기임)의 화합물과, 염기를 추가로 사용하여 반응시키는 단계 및 경우에 따라 상기 수득한 화합물(I)을 공지된 방법으로 이의 염 중 하나로 전환시키는 단계를 포함하는, R6가 C1-C8-알킬, C4-C7-시클로알킬 또는 아릴-(C1-C4)-알킬인, 제1항에 청구된 바와 같은 화학식(I)의 카르바모일카르보히드라지드 또는 이들의 염의 제조 방법.R 6 is hydrogen, the formula carbamoyl carbonyl hydrazide of the formula (I) as claimed in claim 1, wherein R 6 -X (where R 6 is C 1 -C 8 - alkyl, C 4 -C 7 Reacting the compound of -cycloalkyl or aryl- (C 1 -C 4 ) -alkyl and X is a negative leaving group, with further use of a base, and optionally the obtained compound (I) Claim 1 wherein R 6 is C 1 -C 8 -alkyl, C 4 -C 7 -cycloalkyl or aryl- (C 1 -C 4 ) -alkyl comprising the step of converting to one of its salts A process for preparing carbamoylcarbohydrazide of formula (I) or salts thereof as described above. 통상의 첨가제 및 화합물(Ia) 내지 (Io)를 제외한, 유효량의 제1항에 정의한 바와 같은 화학식(I)의 화합물 또는 이의 염 중 하나를 함유하는, 유해한 진균류 방제용으로 적합한 조성물.A composition suitable for controlling harmful fungi, comprising an effective amount of one of the compounds of formula (I) or salts thereof as defined in claim 1, excluding conventional additives and compounds (Ia) to (Io). 유효량의, 화합물(Ia) 내지 (Io)를 포함하여, 제1항에 청구된 바와 같은 화학식(I)의 화합물 또는 이의 염 중 하나, 또는 제5항에 청구된 바와 같은 화합물(I)을 함유하는 조성물로 유해한 진균류, 이들의 서식지 또는 이들로부터 보호하고자 하는 식물, 표면, 물질 또는 공간을 처리하는 단계를 포함하는, 유해 진균류의 방제 방법.Containing an effective amount of a compound of formula (I) or a salt thereof as claimed in claim 1, or a compound (I) as claimed in claim 5, including compounds (Ia) to (Io) A method of controlling harmful fungi, comprising the step of treating harmful fungi, their habitats or plants, surfaces, substances or spaces to be protected from them. 화합물(Ia) 내지 (Io)를 포함하여, 제1항에 청구된 바와 같은 화학식(I)의 화합물 또는 이들의 염 중 하나의, 유해 진균류 방제용 용도.Use for controlling harmful fungi, either of compounds of formula (I) as claimed in claim 1 or salts thereof, including compounds (Ia) to (Io). 화학식(IV)의 아미노산 히드라지드.Amino acid hydrazide of formula (IV). 상기 식에서, X3은 산소이고, R3은 CH(CH3)2, CH2CH(CH3)2또는 CH(CH3)C2H5이고 R4, R5, R6및 R7은 제1항에 정의된 바와 같고; 여기서, 하기 라디칼의 정의에 따르는 화합물은 제외한다:IVa-b(R3=CH(CH3)2또는 (CH2)2CH3; R4,R5=H; R6,R7=CH2CH2Cl), IVc-e(R3=CH(CH3)2, CH(CH3)CH2CH3또는 CH2CH(CH3)2; R4, R5=H; R6,R7=CH2CH2Br), IVf(R3=CH(CH3)2; R4,R5,R6=H; R7=Ph), IVg(R3=CH(CH3)2; R4,R5=H; R6,R7=Ph).Wherein X 3 is oxygen, R 3 is CH (CH 3 ) 2 , CH 2 CH (CH 3 ) 2 or CH (CH 3 ) C 2 H 5 and R 4 , R 5 , R 6 and R 7 are As defined in claim 1; Here, compounds according to the definition of the following radicals are excluded: IVa-b (R 3 = CH (CH 3 ) 2 or (CH 2 ) 2 CH 3 ; R 4 , R 5 = H; R 6 , R 7 = CH 2 CH 2 Cl), IVc-e (R 3 = CH (CH 3 ) 2 , CH (CH 3 ) CH 2 CH 3 or CH 2 CH (CH 3 ) 2 ; R 4 , R 5 = H; R 6 , R 7 = CH 2 CH 2 Br), IVf (R 3 = CH (CH 3 ) 2 ; R 4 , R 5 , R 6 = H; R 7 = Ph), IVg (R 3 = CH (CH 3 ) 2 R 4 , R 5 = H; R 6 , R 7 = Ph). 제8항에 있어서, R3이 CH(CH3)2이고, R4및 R5는 제1항에 정의된 바와 같고, R6은 C1-C8-알킬 (이는 부분적으로 또는 완전히 할로겐화되고(되거나) 시아노, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, C3-C7-시클로알킬, C3-C7-시클로알케닐, 아릴, 아릴옥시 및 헤테로아릴로 이루어진 군으로부터 선택된 기를 1 내지 3개 포함하며, 이들 중에서 시클릭 라디칼의 경우에는 할로겐, 시아노, C1-C4-알킬, C1-C4-알콕시알킬, C1-C4-할로알킬, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, 아릴, 아릴옥시 및 헤테로아릴로 이루어진 군으로부터 선택된 치환체 1 내지 3개를 포함할 수 있음)이고, R7은 아릴(이는 할로겐, 시아노, C1-C4-알킬, C1-C4-알콕시알킬, C1-C4-할로알킬, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, 아릴, 아릴옥시 및 헤테로아릴로 이루어진 군으로부터 선택된 치환체 1 내지 3개를 포함할 수 있으며, 여기서 시클릭 치환체의 경우에는 할로겐, 시아노, C1-C4-알킬, C1-C4-알콕시알킬, C1-C4-할로알킬, C1-C4-알콕시, C1-C4-할로알콕시 및 C1-C4-알킬티오로 이루어진 군으로부터 선택된 치환체 1 내지 3개를 포함할 수 있음)인, 화학식(IV)의 아미노산 히드라지드.The compound of claim 8, wherein R 3 is CH (CH 3 ) 2 , R 4 and R 5 are as defined in claim 1, and R 6 is C 1 -C 8 -alkyl, which is partially or fully halogenated; (Or) cyano, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkenyl , 1 to 3 groups selected from the group consisting of aryl, aryloxy and heteroaryl, of which in the case of cyclic radicals halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxyalkyl , C 1 -C 4 - haloalkyl, C 1 -C 4 - alkoxy, C 1 -C 4 - haloalkoxy, C 1 -C 4 - alkylthio, aryl, aryloxy and heteroaryl substituents selected from the group consisting of 1 To 3, and R 7 is aryl (which is halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxyalkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 - alkoxy, C 1 -C 4 - haloalkoxy, C 1 -C 4 - alkylthio, Oh , Aryloxy and for click when the substituent may include one to three substituents selected, in which from the group consisting of heteroaryl include halogen, cyano, C 1 -C 4 - alkyl, C 1 -C 4 - alkoxyalkyl , C 1 -C 4 - haloalkyl, C 1 -C 4 - alkoxy, C 1 -C 4 - haloalkoxy, and C 1 -C 4 - which may include one to three substituents selected from the group consisting of alkylthio Amino acid hydrazide of formula (IV). ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019960706896A 1994-06-03 1995-05-20 Carbamoyl Carboxylic Acid Hydrazides and Their Use Against Fungi KR970703306A (en)

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DE1995104423 DE19504423A1 (en) 1995-02-10 1995-02-10 New carbamoyl carboxylic acid hydrazide derivs.
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