KR950704233A - Benzoylcyclohexenone, preparation method thereof, and their use as herbicide and plant growth regulator (BENZOYLCYCLOHEXENONES, METHODS OF PREPARING THEM AND THEIR USE AS HERBICIDES AND PLANT GROWTH REGULATORS) - Google Patents

Benzoylcyclohexenone, preparation method thereof, and their use as herbicide and plant growth regulator (BENZOYLCYCLOHEXENONES, METHODS OF PREPARING THEM AND THEIR USE AS HERBICIDES AND PLANT GROWTH REGULATORS)

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KR950704233A
KR950704233A KR1019950702368A KR19950702368A KR950704233A KR 950704233 A KR950704233 A KR 950704233A KR 1019950702368 A KR1019950702368 A KR 1019950702368A KR 19950702368 A KR19950702368 A KR 19950702368A KR 950704233 A KR950704233 A KR 950704233A
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alkyl
compound
halogen
formula
alkoxy
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KR1019950702368A
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Korean (ko)
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스테판 뮐러
라이너 쉬쯔
클라우스 바우어
헤르만 비링거
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바이세르트, 루츠
훽스트 쉐링 아그레보 게엠베하
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Publication of KR950704233A publication Critical patent/KR950704233A/en

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    • A—HUMAN NECESSITIES
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Abstract

하기 일반식(Ⅰ)의 화합물은 선택적인 제초제 또는 식물 생장조절제로서 본 발명에 따라 적합하다；The compounds of formula (I) are suitable according to the invention as selective herbicides or plant growth regulators;

상기 식에서, n은 0 내지 6의 정수이고, X는 할로겐, CN, OCN, SCN, C2-C4-알키닐 또는 CHR5R6이고, R5및 R6은 서로 독립적으로 CN, NO2, 포르밀, 임의적으로 할로-치환된 (C1-C4-알킬)카보닐, 임의적으로 할로-치환된(C1-C4-알콕시)-카보닐 또는 임의적으로 치환된 페닐카보닐이며, R1은 임의적으로 할로-치환된 C1-C4-알킬, 임의적으로 할로-치환된 C3-C6-사이클로알킬 또는 임의적으로 치환된 페닐이고, R2는 할로겐, CN, NO2, C1-C3-알킬, C1-C3-알콕시, C1-C3-할로알킬, C1-C3-할로알콕시 또는 R7S(O)m-이고, R7은 C1-C3-알킬이며, m은 0, 1 또는 2이고, R3은 H, 할로겐, OH, C1-C3-알킬, C1-C3-알콕시, C1-C3-할로알킬, C1-C3-할로알콕시 또는 (C1-C3-알콕시)카보닐이고, R4는 H, CN, NO2, 할로겐, C1-C3할로알킬, -C1-C3-할로알콕시 또는 R8S(O)p-이고, R8은 C1-C3-알킬이며, p는 0, 1 또는 2이다.Wherein n is an integer from 0 to 6, X is halogen, CN, OCN, SCN, C 2 -C 4 -alkynyl or CHR 5 R 6 , and R 5 and R 6 are independently of each other CN, NO 2 , Formyl, optionally halo-substituted (C 1 -C 4 -alkyl) carbonyl, optionally halo-substituted (C 1 -C 4 -alkoxy) -carbonyl or optionally substituted phenylcarbonyl, R 1 is optionally halo-substituted C 1 -C 4 -alkyl, optionally halo-substituted C 3 -C 6 -cycloalkyl or optionally substituted phenyl, R 2 is halogen, CN, NO 2 , C 1- C 3 -alkyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkyl, C 1 -C 3 -haloalkoxy or R 7 S (O) m- , R 7 is C 1 -C 3 -alkyl, m is 0, 1 or 2, R 3 is H, halogen, OH, C 1 -C 3 -alkyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkyl, C 1 -C 3 -haloalkoxy or (C 1 -C 3 -alkoxy) carbonyl, R 4 is H, CN, NO 2 , halogen, C 1 -C 3 haloalkyl, -C 1 -C 3 -haloalkoxy or R 8 S (O) p −, R 8 is C 1 -C 3 -alkyl and p is 0, 1 or 2.

이들 화합물은 X가 C1인 일반식(Ⅰ)의 화합물을 제외하고는 신규하다.These compounds are novel except for compounds of formula (I) wherein X is C1.

다양한 방법에 의해 2-벤조일-1,3-사이클로헥산디온으로부터 이들을 제조할 수 있다.These can be prepared from 2-benzoyl-1,3-cyclohexanedione by various methods.

Description

벤조일사이클로헥세논, 이들의 제조방법, 및 이들의 제초제 및 식물생장 조절제로서의 용도(BENZOYCYCLOHEXENONES, METHODS OF PREPARING THEM AND THEIR USE AS HERBICIDES AND PLANT GROWTH REGULATORS)BENZOYCYCLOHEXENONES, METHODS OF PREPARING THEM AND THEIR USE AS HERBICIDES AND PLANT GROWTH REGULATORS

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

Claims (10)

하기 일반식(Ⅰ)의 화합물의 제초제 또는 식물 생장 조절제로서의 용도：Use of a compound of the general formula (I) as a herbicide or plant growth regulator: 상기 식에서, n은 0 내지 6의 정수이고, X는 할로겐, CN, OCN, SCN, C2-C4-알키닐 또는 CHR5R6이고, R5및 R6은 서로 독립적으로 CN, NO2, 포르밀, (C1-C4-알킬)카보닐 또는 (C1-C4-알콕시)-카보닐(마지막 두 라디칼은 할로겐 원자 하나 이상에 의해 치환 또는 비치환됨), 또는 비치환 또는 치환된 페닐카보닐이며, R1라디칼은 C1-C4-알킬 또는 C3-C6-사이클로알킬(마지막 두 라디칼은 할로겐 원자 하나 이상에 의해 치환 또는 비치환됨) 또는 비치환 또는 치환된 페닐로 이루어진 군으로부터 선택된 동일하거나 또는 상이한 치환기이고, R2는 할로겐, CN, NO2, C1-C3-알킬, C1-C3-알콕시, C1-C3-할로알킬, C1-C3-할로알콕시 또는 R7S(O)m-이고, R7은 C1-C3-알킬이며, m은 0, 1 또는 2이고, R3은 H, 할로겐, OH, C1-C3-알킬, C1-C3-알콕시, C1-C3-할로알킬, C1-C3-할로알콕시 또는 (C1-C3-알콕시)카보닐이고, R4는 H, CN, NO2, 할로겐, C1-C3할로알킬, -C1-C3-할로알콕시 또는 R8S(O)p-이고, R8은 C1-C3-알킬이며, p는 0, 1 또는 2이다.Wherein n is an integer from 0 to 6, X is halogen, CN, OCN, SCN, C 2 -C 4 -alkynyl or CHR 5 R 6 , and R 5 and R 6 are independently of each other CN, NO 2 , Formyl, (C 1 -C 4 -alkyl) carbonyl or (C 1 -C 4 -alkoxy) -carbonyl (the last two radicals are unsubstituted or substituted by one or more halogen atoms), or unsubstituted or substituted Phenylcarbonyl, and the R 1 radical is C 1 -C 4 -alkyl or C 3 -C 6 -cycloalkyl (the last two radicals being substituted or unsubstituted by one or more halogen atoms) or unsubstituted or substituted phenyl Are the same or different substituents selected from the group consisting of R 2 is halogen, CN, NO 2 , C 1 -C 3 -alkyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkyl, C 1 -C 3 -haloalkoxy or R 7 S (O) m- , R 7 is C 1 -C 3 -alkyl, m is 0, 1 or 2, R 3 is H, halogen, OH, C 1 -C 3 -Alkyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkyl, C 1 -C 3 -haloalkoxy or (C 1 -C 3 -alkoxy) carbonyl, R 4 is H, CN, NO 2 , halogen, C 1 -C 3 haloalkyl, -C 1 -C 3 -halo Alkoxy or R 8 S (O) p −, R 8 is C 1 -C 3 -alkyl, p is 0, 1 or 2. 제1항에 있어서, n이 0 내지 4의 정수이고, X가 할로겐, CN, OCN, SCN, C2-C4-알키닐 또는 CHR5R6이며, R5및 R6이 서로 독립적으로 CN, NO2, 포르밀, (C1-C4-알킬)카보닐, (C1-C4-알콕시)-카보닐 또는 페닐카보닐이고, 마지막 3개의 라디칼이 할로겐 원자 하나 이상에 의해 치환 또는 비치환되고, R1라디칼이 C1-C3-알킬, C4-C6-사이클로알킬 또는 페닐로 이루어진 군으로부터 선택된 동일하거나 또는 상이한 치환기이고, 마지막 3개의 라디칼이 할로겐 원자 하나 이상에 의해 치환 또는 비치환되며, R2는 할로겐, CN, NO2, C1-C2-알킬, C1-C2-알콕시, C1-C2-할로알킬, C1-C2-할로알콕시 또는 R7S(O)m-이고, R7이 C1-C2-알킬이고, m은 0, 1 또는 2이고, R3이 H, 할로겐, OH, C1-C2-알킬, C1-C2-알콕시, C1-C2-할로알킬, C1-C2-할로알콕시 또는 (C1-C2-알콕시)카보닐이고, R4가 H, 할로겐, CN, NO2, C1-C2-할로알콕시 또는 R8S(O)p-이고, R8이 C1-C3-알킬이며, p는 0, 1 또는 2인 일반식(Ⅰ)의 화합물 용도.The compound of claim 1, wherein n is an integer from 0 to 4, X is halogen, CN, OCN, SCN, C 2 -C 4 -alkynyl or CHR 5 R 6 , and R 5 and R 6 are independently of each other CN. , NO 2 , formyl, (C 1 -C 4 -alkyl) carbonyl, (C 1 -C 4 -alkoxy) -carbonyl or phenylcarbonyl, and the last three radicals are substituted by one or more halogen atoms or Unsubstituted, the R 1 radical is the same or different substituent selected from the group consisting of C 1 -C 3 -alkyl, C 4 -C 6 -cycloalkyl or phenyl, and the last three radicals are substituted by one or more halogen atoms Or unsubstituted, R 2 is halogen, CN, NO 2 , C 1 -C 2 -alkyl, C 1 -C 2 -alkoxy, C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy or R 7 S (O) m- , R 7 is C 1 -C 2 -alkyl, m is 0, 1 or 2, R 3 is H, halogen, OH, C 1 -C 2 -alkyl, C 1- C 2 - alkoxy, C 1 -C 2 - haloalkyl, C 1 -C 2 - haloalkoxy or (C 1 -C 2 - Al City) and the carbonyl group, R 4 is H, halogen, CN, NO 2, C 1 -C 2 - , and, R 8 is C 1 -C 3 - - haloalkoxy or R 8 S (O) p alkyl, p Is a compound of formula (I) wherein 0, 1 or 2. 제1항 또는 제2항에 있어서, n이 0 내지 3의 정수이고, X가 플루오르, 염소 브롬, 요오드, 시아노, 시아네이토, 티오시아네이토, 에티닐, 1-프로피닐, CH(CN)2, CH(CN)COOC2H5, CH(CN)COOH3, CH(COCH3)COOCH3, CH(COCH3)COOC2H5, CH(COOCH3)NO2, CH(COCH)2, CH(COOCH3)2, CH(COOC2H5)2, CH(COOCH3)NO2또는 CH(COOC2H5)NO2이고, R1이 메틸, 에틸, i-프로필, 사이클로펜틸, 사이클로헥실 또는 페닐이고, R2가 플루오르, 염소, 시아노, 니트로, 메틸, 메톡시, 트리플루오로메틸, 트리플루오로메톡시 또는 메틸설포닐이고, R3이 수소, 염소, 하이드록실, 메틸, 메톡시, 트리플루오로메틸, 트리플루오로메톡시 또는 메틸시카보닐이며, R4가 수소, 염소, 브롬, 시아노, 니트로, 트리플루오로메틸, 디플루오로메톡시, 트리플루오로메톡시, 메틸설포닐 또는 에틸설포닐인 일반식(Ⅰ)의 화합물의 용도.3. The compound of claim 1, wherein n is an integer from 0 to 3, X is fluorine, chlorine bromine, iodine, cyano, cyanato, thiocyanato, ethynyl, 1-propynyl, CH ( CN) 2 , CH (CN) COOC 2 H 5 , CH (CN) COOH 3 , CH (COCH 3 ) COOCH 3 , CH (COCH 3 ) COOC 2 H 5 , CH (COOCH 3 ) NO 2 , CH (COCH) 2 , CH (COOCH 3 ) 2 , CH (COOC 2 H 5 ) 2 , CH (COOCH 3 ) NO 2 or CH (COOC 2 H 5 ) NO 2 , R 1 is methyl, ethyl, i-propyl, cyclopentyl , Cyclohexyl or phenyl, R 2 is fluorine, chlorine, cyano, nitro, methyl, methoxy, trifluoromethyl, trifluoromethoxy or methylsulfonyl, and R 3 is hydrogen, chlorine, hydroxyl, methyl , Methoxy, trifluoromethyl, trifluoromethoxy or methylcycarbonyl, R 4 is hydrogen, chlorine, bromine, cyano, nitro, trifluoromethyl, difluoromethoxy, trifluoromethoxy, methyl Of formula (I), which is sulfonyl or ethylsulfonyl Total water usage. 제1항 내지 제3항중 어느 한항에 있어서, X가 염소인 일반식(Ⅰ)의 화합물을 제외한 일반식(Ⅰ)의 화합물의 용도.The use of a compound of formula (I) according to any one of claims 1 to 3, except for the compound of formula (I), wherein X is chlorine. 제1항 내지 제4항중 어느 한 항에 정의된 일반식(Ⅰ)의 화합물 및 통상적인 제형 보조제를 포함하는 제초 조성물.A herbicidal composition comprising a compound of formula (I) as defined in any one of claims 1 to 4 and a conventional formulation aid. a)X가 플루오르, 브롬 또는 요오드인 경우, 하기 일반식(Ⅱ)의 화합물을 적합한 할로겐화제와 반응시키거나, 또는 b)X가 CN, OCN, SCN, 알키닐 또는 CHR5R6이고, R5및 R6이 일반식(Ⅰ)에서 정의된 바와 같은 경우, 방법 a)에서 제조된 화합물을 적합한 시약 MX[여기에서, M은 알칼리금속, 알칼리토금속 또는 구리이고, X는 일반식(Ⅰ)에서 방법 b)인 경우에 대해 정의된 바와 같음]와 반응시키거나, 또는 c)X가 플루오르 또는 요오드인 경우, X가 브롬인 일반식(Ⅰ)의 화합물을 알칼리금속 플루오라이드 또는 알칼리금속 요오다이드와 반응시키는 것을 포함하는, 제4항에 정의된 일반식(Ⅰ)의 화합물의 제조방법；a) when X is fluorine, bromine or iodine, the compound of formula II is reacted with a suitable halogenating agent, or b) X is CN, OCN, SCN, alkynyl or CHR 5 R 6 and R When 5 and R 6 are as defined in general formula (I), the compound prepared in process a) is replaced with a suitable reagent MX [where M is an alkali metal, alkaline earth metal or copper, and X is general formula (I) Or as defined for method b), or c) when X is fluorine or iodine, a compound of formula (I) wherein X is bromine is an alkali metal fluoride or an alkali metal iodine A process for the preparation of a compound of formula (I) as defined in claim 4 comprising reacting with an id; 상기 식에서, R1,R2,R3,R4및 n은 일반식(Ⅰ)에서 정의된 바와 같다.Wherein R 1 , R 2 , R 3 , R 4 and n are as defined in general formula (I). 습윤성 분말제, 수용성 분말제, 유화 농축액, 수용액 또는 농축액, 유화액, 분무 용액(탱크 믹스), 캡슐 현탁액, 오일계 또는 수계 분산액, 현탁 유화액, 현탁 농축액, 분제, 오일-혼화성 용액, 종자-드레싱 제품, 미소과립제, 분무 과립제, 피복 과립제 및 흡착 과립제, 토양 용도 및 살포용 과립제, 수분산성 과립제, ULV제제, 미소캡슐 및 왁스로 이루어진 군으로부터 선택되는 통상적인 농작물 보호 제품 제형과 유사한 방식으로 일반식(Ⅰ)의 화합물 하나 이상을 제형시키는 것을 포함하는 제5항에 따른 조성물의 제조방법.Wettable powders, water soluble powders, emulsion concentrates, aqueous solutions or concentrates, emulsions, spray solutions (tank mixes), capsule suspensions, oil-based or aqueous dispersions, suspension emulsions, suspension concentrates, powders, oil-miscible solutions, seed-dressing General formula in a manner similar to conventional crop protection product formulations selected from the group consisting of products, microgranules, spray granules, coated granules and adsorbent granules, soil use and spray granules, water dispersible granules, ULV formulations, microcapsules and waxes A process for preparing a composition according to claim 5 comprising formulating at least one compound of (I). 제1항 내지 제4항중 어느 한 항에 정의된 일반식(Ⅰ)의 화합물 유효량을 식물 또는 이들 식물이 자라는 지역에 투여하는 것을 포함하는 바람직하지 못한 식물을 억제하거나 또는 식물의 생장을 조절하는 방법.A method of inhibiting or controlling the growth of a plant, the method comprising administering to the plant or an area in which these plants grow an effective amount of the compound of formula (I) as defined in any one of claims 1 to 4 . 제8항에 있어서, 유용한 식물중에 자라는 잡초를 억제하는 방법.The method of claim 8, wherein the weeds grow in useful plants. 제9항에 있어서, 유용한 식물이 밀, 보리, 호밀, 벼 및 옥수수로 이루어진 군으로부터 선택되는 방법.10. The method of claim 9, wherein the useful plant is selected from the group consisting of wheat, barley, rye, rice and corn. ※ 참고사항:최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019950702368A 1992-12-12 1993-12-02 Benzoylcyclohexenone, preparation method thereof, and their use as herbicide and plant growth regulator (BENZOYLCYCLOHEXENONES, METHODS OF PREPARING THEM AND THEIR USE AS HERBICIDES AND PLANT GROWTH REGULATORS) KR950704233A (en)

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