KR920700211A - Heterocyclic compounds - Google Patents

Heterocyclic compounds

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Publication number
KR920700211A
KR920700211A KR1019910700156A KR910700156A KR920700211A KR 920700211 A KR920700211 A KR 920700211A KR 1019910700156 A KR1019910700156 A KR 1019910700156A KR 910700156 A KR910700156 A KR 910700156A KR 920700211 A KR920700211 A KR 920700211A
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South Korea
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alkyl
methyl
oxo
fluoro
ethyl
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KR1019910700156A
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Korean (ko)
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주키 밀로스
빈터니쯔 파울
젤러 마르틴
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베르너 벨데크
시바-가이기 아게
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Publication of KR920700211A publication Critical patent/KR920700211A/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

내용 없음No content

Description

헤테로 고리 화합물Heterocyclic compounds

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음As this is a public information case, the full text was not included.

Claims (21)

하기 일반식(Ⅰ)의 화합물 및 R1이 C1-4－알킬, C2-5알켄일 또는 C3-5－알킨일인 일반식(Ⅰ)의 화합물의 에놀에테르, 및 R1이 수소이고 R2가 수소 및/또는 C2-5－카르복시알킬인 일반식(Ⅰ)의 화합물의 염:The enol ether of the compound of formula (I), wherein R 1 is C 1-4 -alkyl, C 2-5 alkenyl or C 3-5 alkynyl, and R 1 is hydrogen Salts of compounds of formula (I) wherein R 2 is hydrogen and / or C 2-5 -carboxyalkyl: 상기식에서, R1은 수소, C1-4－알킬, C1-4할로알킬, C2-5알켄일 또는 C3-5알킨일이고, R2는 수소, C1-4－알킬, C1-4－할로알킬, C1-4－알콕시－C1-4－알킬, C1-4－알콕시－C1-4－알킬, C2-5시아노알킬, C2-5－카르복시알킬, C2-5알콕시카르보닐－C1-4－알킬, C2-5할로알콕시카르보닐C1-4-알킬 C1-4－알콕시－C2-5－알콕시카르보닐－C1-4－알킬, C2-5알콕시카르보닐－C2-5－알콕시카르보닐－C1-4－알킬, C4-7－시클로알킬옥시카르보닐－C1-4－알킬, 카르바모일－C1-4－알킬, 모노(C1-4－알킬)카르바모일－C1-4－알킬, 디(C1-4－알킬)카르바모일－C1-4－알킬, C3-4－알켄일, C3-4－할로알켄일, 신나밀, C3-4－알킨일 또는 C3-4－할로알킨일이며, R3및 R4는 서로 독립적으로 수소, 할로겐, C1-4－알킬 또는 페닐이고, R5는 수소, 플루오르 또는 염소이고, R6는 수소, 할로겐 또는 C1-4－알킬이고, R7은 C1-4－알킬이거나, 또는 R1이 C1-4－할로알킬이 아닌 경우 C1-4－할로알킬일 수 있으며, n은 0 또는 1이고, X는 산소 또는 황이다.Wherein R 1 is hydrogen, C 1-4 -alkyl, C 1-4 haloalkyl, C 2-5 alkenyl or C 3-5 alkynyl, R 2 is hydrogen, C 1-4 -alkyl, C 1-4 -haloalkyl, C 1-4 -alkoxy-C 1-4 -alkyl, C 1-4 -alkoxy-C 1-4 -alkyl, C 2-5 cyanoalkyl, C 2-5 -carboxyalkyl , C 2-5 alkoxycarbonyl-C 1-4 -alkyl, C 2-5 haloalkoxycarbonylC 1-4 -alkyl C 1-4 -alkoxy-C 2-5 -alkoxycarbonyl-C 1-4 -alkyl, C 2-5 alkoxycarbonyl -C 2-5 - alkoxycarbonyl -C 1-4 -alkyl, C 4-7 - cycloalkyloxy-carbonyl -C 1-4 -alkyl, carbamoyl -C 1-4 -alkyl, mono (C 1-4 -alkyl) carbamoyl-C 1-4 -alkyl, di (C 1-4 -alkyl) carbamoyl-C 1-4 -alkyl, C 3-4 -alkenyl, C 3-4 - alkenyl halo, cinnamyl, C 3-4 - alkynyl, or C 3-4-alkynyl, and halo, R 3 and R 4 are independently hydrogen, halogen, C 1- to each other 4 -alkyl or phenyl and R 5 is hydrogen, fluorine or Chlorine, R 6 is hydrogen, halogen or C 1-4 -alkyl, R 7 is C 1-4 -alkyl, or C 1-4 -haloalkyl when R 1 is not C 1-4 -haloalkyl And n is 0 or 1 and X is oxygen or sulfur. 제1항에 있어서, R1이 메틸 또는 디플루오로메틸인 화합물.The compound of claim 1, wherein R 1 is methyl or difluoromethyl. 제1항 또는 제2항에 있어서, R2가 C1-4－알킬, C1-4－알콕시－C1-4－알킬, C3-4－알켄일 또는 C3-4－알킨일인 화합물.The compound of claim 1 or 2, wherein R 2 is C 1-4 -alkyl, C 1-4 -alkoxy-C 1-4 -alkyl, C 3-4 -alkenyl or C 3-4 -alkynyl . 제1항 내지 제3항중 어느 하나에 있어서, R3및 R4가 각각 수소인 화합물.The compound of any one of claims 1-3, wherein R 3 and R 4 are each hydrogen. 제1항 내지 제4항중 어느 하나에 있어서, R5가 수소 또는 플루오르인 화합물.The compound of any one of claims 1-4, wherein R 5 is hydrogen or fluorine. 제1항 내지 제5항중 어느 하나에 있어서, R6가 수소, 플루오르 염소, 브롬 또는 메틸인 화합물. 6. The compound of claim 1, wherein R 6 is hydrogen, fluorine chlorine, bromine or methyl. 7. 제1항 내지 제6항중 어느 하나에 있어서, R7가 메틸, 에틸, 트리플루오로메틸 또는 펜타플루오로에틸인 화합물.The compound of any one of claims 1-6, wherein R 7 is methyl, ethyl, trifluoromethyl or pentafluoroethyl. 제1항 내지 제7항중 어느 하나에 있어서, n이 0이며 X가 황인 화합물.8. The compound of claim 1, wherein n is 0 and X is sulfur. 9. 제1항 내지 제7항중 어느 하나에 있어서, n이 1이고 X가 산소인 화합물.8. A compound according to any one of the preceding claims wherein n is 1 and X is oxygen. 제1항에 있어서, 다음의 화합물로부터 선택된 화합물:The compound of claim 1 selected from the following compounds: 6－에틸－3－〔4－알릴－3,4－디히드로－7－플루오로－3－옥소－2H－1,4－벤조옥사진－6－일〕－1－메틸－2,4(1H,3H)－피리미딘디온 및 6－에틸－3－〔3,4－디히드로－7－플루오로－3－옥소－4－(2－프로핀일)－2H－1,4－벤조옥사진－6－일〕－1－메틸－2,4(1H,3H)－피리미딘디온.6-ethyl-3- [4-allyl-3,4-dihydro-7-fluoro-3-oxo-2H-1,4-benzooxazine-6-yl] -1-methyl-2,4 ( 1H, 3H) -pyrimidinedione and 6-ethyl-3- (3,4-dihydro-7-fluoro-3-oxo-4- (2-propynyl) -2H-1,4-benzoxazine -6-day] -1 -methyl- 2,4 (1H, 3H)-pyrimidinedione. 제1항에 있어서, 다음의 화합물로부터 선택된 화합물:The compound of claim 1 selected from the following compounds: 6－에틸－3－〔4－알릴－3,4－디히드로－7－플루오로－3－옥소－2H－1,4－벤조옥사진－6－일〕5－브로모－1－메틸－2,4(1H,3H)－피리미딘디온, 3－〔3,4－디히드로－7－플루오로－3－옥소－4－(2－프로핀일)－2H－1,4－벤조옥사진－6－일〕－1－메틸－6(n－프로필)－2,4(1H,3H)－피리미딘디온, 6－에틸－3－〔3,4－디히드로－7－플루오로－4－이소프로필－3－옥소－2H－1,4－벤조옥사진－6－일〕－1－메틸－2,4(1H,3H)－피리미딘디온, 6－에틸－3－〔4－2차－부틸－3,4－디히드로－7－플루오로-3－옥소－2H－1,4－벤조옥사진－6－일〕－1－메틸－2,4(1H,3H)－피리미딘디온, 6－에틸－3－〔3,4－디히드로－7－플루오로－4－(1－메톡시에틸)3－옥소－2H－1,4－벤조옥사진－6－일〕－1－메틸－2,4(1H,3H)－피리미딘디온, 6－에틸－3－〔3,4－디히드로－7－플루오로-4-(1-메톡시프로필)－3－옥소-2H-1,4-벤조옥사진-6-일]-1-메틸-2,4(1H,3H)-피리미딘디온, 6-에틸-3-[3,4-디히드로-7-플루오로옥소－4－(1－메틸－2－프로펜일)－3－옥소－2H－1,4－벤조옥사진－6－일〕－1－메틸－2,4(1H,3H)－피리미딘디온, 6－에틸－3－〔3,4－디히드로－7－플루오로－4－(1－메틸－2－프로핀일)－3－옥소－2H－1,4－벤조옥사진－6－일〕－1－메틸－2,4(1H,3H)－피리미딘디온, 6－에틸－3－〔6－플루오로－3－이소프로필－2－옥소－5－벤조티아졸린일〕－1－메틸－2,4(1H,3H)－피리미딘디온, 6－에틸－3－〔3－2차－부틸－6－플루오로－2－옥소－5－벤조티아졸린일〕－1－메틸－2,4(1H,3H)－피리미딘디온, 6－에틸－3－〔6－플루오로－3－(1－메톡시에틸)－2－옥소－5－벤조티아졸린일〕－1－메틸－2,4(1H,3H)－피리미딘디온, 6－에틸－3－〔6－플루오로－3－(1－메톡시프로필)－2－옥소－5－벤조티아졸린일〕－1－메틸－2,4(1H,3H)－피리미딘디온, 6－에틸－3－〔3－알릴－6－플루오로－2－옥소－5－벤조티아졸린일〕－1－메틸－2,4(1H,3H)－피리미딘디온, 6－에틸－3－〔6－플루오로－3－(1－메틸－2－프로펜일)－2－옥소－5－벤조티아졸린일〕－1－메틸－2,4(1H,3H)－피리미딘디온,6－에틸－3－〔6－플루오로－2－옥소－3－(2－프로핀일)－5－벤조티아졸린일〕－1－메틸－2,4(1H,3H)－피리미딘디온 및 6－에틸－3－〔6－플루오로－3－(1－메틸－2－프로핀일)－2－옥소－5－벤조티아졸린일〕－1－메틸－2,4(1H,3H)－피리미딘디온.6-ethyl-3- [4-allyl-3,4-dihydro-7-fluoro-3-oxo-2H-1,4-benzooxazine-6-yl] 5-bromo-1-methyl- 2,4 (1H, 3H) -pyrimidinedione, 3- (3,4-dihydro-7-fluoro-3-oxo-4- (2-propynyl) -2H-1,4-benzoxazine -6-yl] -1-methyl-6 (n-propyl) -2,4 (1H, 3H) -pyrimidinedione, 6-ethyl-3- [3,4-dihydro-7-fluoro-4 -Isopropyl-3-oxo-2H-1,4-benzooxazine-6-yl] -1-methyl-2,4 (1H, 3H) -pyrimidinedione, 6-ethyl-3- [4-2 Tea-butyl-3,4-dihydro-7-fluoro-3-oxo-2H-1,4-benzooxazine-6-yl] -1-methyl-2,4 (1H, 3H) -pyrimidine Dione, 6-ethyl-3- [3,4-dihydro-7-fluoro-4- (1-methoxyethyl) 3-oxo-2H-1,4-benzoxazine-6-yl] -1 -Methyl-2,4 (1H, 3H) -pyrimidinedione, 6-ethyl-3-[3,4-dihydro-7-fluoro-4- (1-methoxy) Lofil) -3-oxo-2H-1,4-benzooxazin-6-yl] -1-methyl-2,4 (1H, 3H) -pyrimidinedione, 6-ethyl-3- [3,4- Dihydro-7-fluorooxo-4- (1-methyl-2-propenyl) -3-oxo-2H-1,4-benzooxazine-6-yl] -1-methyl-2,4 (1H) , 3H) -pyrimidinedione, 6-ethyl-3- (3,4-dihydro-7-fluoro-4- (1 -methyl-2-propynyl) -3 -oxo-2H-1,4- Benzoxazine-6-yl] -1-methyl-2,4 (1H, 3H) -pyrimidinedione, 6-ethyl-3- [6-fluoro-3-isopropyl-2-oxo-5-benzo Thiazolinyl] -1-methyl-2,4 (1H, 3H) -pyrimidinedione, 6-ethyl-3- [3-secondary-butyl-6-fluoro-2--2-oxo-5-benzothiazoline Japanese] -1-methyl-2,4 (1H, 3H) -pyrimidinedione, 6-ethyl-3- [6-fluoro-3- (1-methoxyethyl) -2-oxo-5-benzothia Sleepy yl] -1-methyl-2,4 (1H, 3H) -pyrimidinedione, 6-ethyl-3-[6-fluoro-3- (1-methoxy) Lofil) -2-oxo-5-benzothiazolinyl] -1-methyl-2,4 (1H, 3H) -pyrimidinedione, 6-ethyl-3- [3-allyl-6-fluoro-2--2- Oxo-5-benzothiazolinyl] -1-methyl-2,4 (1H, 3H) -pyrimidinedione, 6-ethyl-3-[6-fluoro-3- (1-methyl-2-propenyl) ) -2-oxo-5-benzothiazolinyl] -1-methyl-2,4 (1H, 3H) -pyrimidinedione, 6-ethyl-3- (6-fluoro-2-oxo-3- ( 2-propynyl) -5-benzothiazolinyl] -1-methyl-2,4 (1H, 3H) -pyrimidinedione and 6-ethyl-3- [6-fluoro-3- (1-methyl-) 2-propynyl) -2-oxo-5-benzothiazolinyl] -1-methyl-2,4 (1H, 3H)-pyrimidinedione. 하기 일반식(Ⅰ)의 화합물, 또는 및 R1이 C1-4－알킬, C2-5알켄일 또는 C3-5－알킨일인 화합물(Ⅰ)의 에놀에테르, 또는 R1이 수소이고 R2가 수소 및/또는 C2-5－카르복시알킬인 화합물(Ⅰ)의 염증 1이상의 유효량, 및 재형보조제를 함유하는 제초제:The compound of formula (I), or enolether of compound (I), wherein R 1 is C 1-4 -alkyl, C 2-5 alkenyl or C 3-5 -alkynyl, or R 1 is hydrogen and R Herbicides containing at least one effective amount of inflammation of Compound (I) which is divalent hydrogen and / or C 2-5 -carboxyalkyl, and a reshaping aid: 상기식에서, R1은 수소, C1-4－알킬, －C1-4할로알킬, －C2-5알켄일 또는 C3-5알킨일이고, R2는 수소, C1-4－알킬, C1-4－할로알킬, C1-4－알콕시－C1-4－알킬, C1-4－알콕시－C1-4－알킬, C2-5－시아노알킬, C2-5－카르복시알킬, C2-5알콕시카르보닐－C1-4－알킬, C2-5할로알콕시카르보닐－C1-4－알킬, C1-4－알콕시－C2-5－알콕시카르보닐－C1-4－알킬, C2-5－알콕시카르보닐－C2-5－알콕시카르보닐－C1-4－알킬, C4-7－시클로알킬옥시카르보닐－C1-4－알킬, 카르바모일－C1-4－알킬, 모노(C1-4－알킬)카르바모일－C1-4－알킬, 디(C1-4－알킬)카르바모일－C1-4－알킬, C3-4－알켄일, C3-4－할로알켄일, 신나밀, C3-4－알킨일 또는 C3-4－할로알킨일이며, R3및 R4는 서로 독립적으로 수소, 할로겐, C1-4－알킬 또는 페닐이고, R5는 수소, 플루오르 또는 염소이고, R6는 수소, 할로겐 또는 C1-4－알킬이고, R7은 C1-4－알킬이거나, 또는 R1이 C1-4－할로알킬이 아닌 경우 C1-4－할로알킬일 수 있으며, n은 0 또는 1이고, X는 산소 또는 황이다.Wherein R 1 is hydrogen, C 1-4 -alkyl, -C 1-4 haloalkyl, -C 2-5 alkenyl or C 3-5 alkynyl, and R 2 is hydrogen, C 1-4 -alkyl , C 1-4 -haloalkyl, C 1-4 -alkoxy-C 1-4 -alkyl, C 1-4 -alkoxy-C 1-4 -alkyl, C 2-5 -cyanoalkyl, C 2-5 -Carboxyalkyl, C 2-5 alkoxycarbonyl-C 1-4 -alkyl, C 2-5 haloalkoxycarbonyl-C 1-4 -alkyl, C 1-4 -alkoxy-C 2-5 -alkoxycarbonyl -C 1-4 -alkyl, C 2-5 -alkoxycarbonyl -C 2-5 -alkoxycarbonyl -C 1-4 -alkyl, C 4-7 -cycloalkyloxycarbonyl-C 1-4 -alkyl , Carbamoyl-C 1-4 -alkyl, mono (C 1-4 -alkyl) carbamoyl-C 1-4 -alkyl, di (C 1-4 -alkyl) carbamoyl-C 1-4- alkyl, C 3-4 - alkenyl, C 3-4 - alkenyl, halo, cinnamyl, C 3-4 - alkynyl, or C 3-4 - alkynyl, and halo, R 3 and R 4 are independently from each other hydrogen , halogen, C 1-4 - alkyl or phenyl, R 5 is hydrogen, Lu and climb or chlorine, R 6 is hydrogen, halogen or C 1-4 - alkyl, R 7 is C 1-4 - alkyl, or R 1 is C 1-4 - C 1-4 is not a halo-alkyl -May be haloalkyl, n is 0 or 1 and X is oxygen or sulfur. 제12항에 있어서, 6－에틸－3－〔4－알릴－3,4－디히드로－7－플루오로－3－옥소－2H－1,4－벤조옥사진－6－일〕－1－메틸－2,4(1H,3H)－피리미딘디온 및 6－에틸－3－〔3,4－디히드로－7－플루오로－3－옥소－4－(2－프로핀일)－2H－1,4－벤조옥사진－6－일〕－1－메틸－2,4(1H,3H)－피리미딘디온 유효량 및 제형보조제를 함유하는 것을 특징으로 하는 제초제.13. 4-Ethyl-3- [4-allyl-3,4-dihydro-7-fluoro-3-oxo-2H-1,4-benzoxazine-6-yl]-1- Methyl-2,4 (1H, 3H) -pyrimidinedione and 6-ethyl-3- [3,4-dihydro-7-fluoro-3-oxo-4- (2-propynyl) -2H-1 , 4-benzoxazine-6-yl] -1-methyl-2,4 (1H, 3H) -pyrimidinedione effective amount and formulation aid. 제12항에 있어서, 다음에 서술된 화합물 그룹중 1이상의 선택된 화합물 유효량 및 제형보조제를 함유하는 것을 특징으로 하는 제초제.13. The herbicide of Claim 12 containing an effective amount of at least one selected compound from the group of compounds described below and a formulation aid. 6－에틸－3－〔4－알릴－3,4－디히드로－7－플루오로－3－옥소－2H－1,4－벤조옥사진－6－일〕5－브로모－1－메틸－2,4(1H,3H)－피리미딘디온, 3－〔3,4－디히드로－7－플루오로－3－옥소－4－(2－프로핀일)－2H－1,4－벤조옥사진－6－일〕－1－메틸－6(n－프로필)－2,4(1H,3H)－피리미딘디온, 6－에틸－3－〔3,4－디히드로－7－플루오로－4－이소프로필－3－옥소－2H－1,4－벤조옥사진－6－일〕－1－메틸－2,4(1H,3H)－피리미딘디온,6－에틸－3－〔4－2차－부틸－3,4－디히드로－7－플루오로－3－옥소－2H－1,4－벤조옥사진－6－일〕－1－메틸－2,4(1H,3H)－피리미딘디온, 6－에틸－3－〔3,4－디히드로－7－플루오로－4－(1－메톡시에틸)－3－옥소－2H－1,4－벤조옥사진－6－일〕－1－메틸－2,4(1H,3H)－피리미딘디온, 6－에틸－3－〔3,4－디히드로－7－플루오로－4－(1－메톡시프로필)－3－옥소－2H－1,4－벤조옥사진－6－일〕－1－메틸－2,4(1H,3H)－피리미딘디온, 6－에틸－3－〔3,4－디히드로－7－플루오로－4－(1－메틸－2－프로펜일)－3－옥소－2H－1,4－벤조옥사진－6－일〕－1－메틸－2,4(1H,3H)－피리미딘디온, 6－에틸－3－〔3,4－디히드로－7－플루오로－4－(1－메틸－2－프로핀일)－3－옥소－2H－1,4－벤조옥사진－6－일〕－1－메틸－2,4(1H,3H)－피리미딘디온, 6－에틸－3－〔6－플루오로－3－이소프로필－2－옥소－5－벤조티아졸린일〕－1－메틸－2,4(1H,3H)－피리미딘디온, 6－에틸－3－〔3－2차－부틸－6－플루오로－2－옥소－5－벤조티아졸린일〕－1－메틸－2,4(1H,3H)－피리미딘디온, 6－에틸－3－〔6－플루오로－3－(1－메톡시에틸)－2－옥소－5－벤조티아졸린일〕－1－메틸－2,4(1H,3H)－피리미딘디온, 6－에틸－3－〔6－플루오로－3－(1－메톡시프로필)－2－옥소－5－벤조티아졸린일〕－1－메틸－2,4(1H,3H)－피리미딘디온, 6－에틸－3－〔3－알릴－6－플루오로－2－옥소－5－벤조티아졸린일〕－1－메틸－2,4(1H,3H)－피리미딘디온, 6－에틸－3－〔6－플루오로－3－(1－메틸－2－프로펜일)－2－옥소－5－벤조티아졸린일〕－1－메틸－2,4(1H,3H)－피리미딘디온,6－에틸－3－〔6－플루오로－2－옥소－3－(2－프로핀일)－5－벤조티아졸린일〕－1－메틸－2,4(1H,3H)－피리미딘디온 및 6－에틸－3－〔6－플루오로－3－(1－메틸－2－프로핀일)－2－옥소－5－벤조티아졸린일〕－1－메틸－2,4(1H,3H)－피리미딘디온.6-ethyl-3- [4-allyl-3,4-dihydro-7-fluoro-3-oxo-2H-1,4-benzooxazine-6-yl] 5-bromo-1-methyl- 2,4 (1H, 3H) -pyrimidinedione, 3- (3,4-dihydro-7-fluoro-3-oxo-4- (2-propynyl) -2H-1,4-benzoxazine -6-yl] -1-methyl-6 (n-propyl) -2,4 (1H, 3H) -pyrimidinedione, 6-ethyl-3- [3,4-dihydro-7-fluoro-4 -Isopropyl-3-oxo-2H-1,4-benzoxazine-6-yl] -1-methyl-2,4 (1H, 3H) -pyrimidinedione, 6-ethyl-3- [4-2 Tea-butyl-3,4-dihydro-7-fluoro-3-oxo-2H-1,4-benzooxazine-6-yl] -1-methyl-2,4 (1H, 3H) -pyrimidine Dione, 6-ethyl-3- [3,4-dihydro-7-fluoro-4- (1-methoxyethyl) -3-oxo-2H-1,4-benzoxazine-6-yl]- 1-Methyl-2,4 (1H, 3H) -pyrimidinedione, 6-ethyl-3- [3,4-dihydro-7-fluoro-4- (1- Methoxypropyl) -3-oxo-2H-1,4-benzooxazine-6-yl] -1-methyl-2,4 (1H, 3H) -pyrimidinedione, 6-ethyl-3- [3, 4-dihydro-7-fluoro-4- (1-methyl-2-propenyl) -3-oxo-2H-1,4-benzooxazine-6-yl] -1-methyl-2,4 ( 1H, 3H) -pyrimidinedione, 6-ethyl-3- (3,4-dihydro-7-fluoro-4- (1-methyl-2-propynyl) -3-oxo-2H-1,4 -Benzoxazine-6-yl] -1-methyl-2,4 (1H, 3H) -pyrimidinedione, 6-ethyl-3- [6-fluoro-3-isopropyl-2-oxo-5-5 Benzothiazolinyl] -1-methyl-2,4 (1H, 3H) -pyrimidinedione, 6-ethyl-3- [3-secondary- butyl-6-fluoro- 2-oxo-5- benzothia Sleepy yl] -1-methyl-2,4 (1H, 3H) -pyrimidinedione, 6-ethyl-3-[6-fluoro-3- (1-methoxyethyl) -2-oxo-5-benzo Thiazolinyl] -1-methyl-2,4 (1H, 3H) -pyrimidinedione, 6-ethyl-3- [6 Fluoro-3- (1-methoxypropyl) -2-oxo-5-benzothiazolinyl] -1-methyl-2,4 (1H, 3H) -pyrimidinedione, 6-ethyl-3- [3 -Allyl-6-fluoro-2-oxo-5-benzothiazolinyl] -1-methyl-2,4 (1H, 3H) -pyrimidinedione, 6-ethyl-3- [6-fluoro-3 -(1-methyl-2-propenyl) -2-oxo-5- benzothiazolinyl] -methyl- 2,4 (1H, 3H)-pyrimidinedione, 6-ethyl-3- [6- Fluoro-2-oxo-3- (2-propynyl) -5-benzothiazolinyl] -1-methyl-2,4 (1H, 3H) -pyrimidinedione and 6-ethyl-3- [6- Fluoro-3- (1-methyl-2-propynyl) -2-oxo-5-benzothiazolinyl] -1-methyl-2,4 (1H, 3H) -pyrimidinedione. a)하기 일반식(Ⅱ)의 화합물을 염기성 조건하에 고리화시키고, 필요한 경우, 수득될 수 있는 일반식(Ⅰ)의 우라실 유도체의 금속염을 산으로 처리하여 산형태(R1=수소)로 전환시켜, R1이 수소이고 R6이 수소, 플루오로 또는 C1-4－알킬일 일반식(Ⅰ)의 화합물 및 필요한 경우 이들 화합물의 금속염을 제조하거나, b)하기 일반식(Ⅲ)의 화합물을 염기성 조건하에서 고리화시키고, 필요한 경우, 수득될 수 있는 일반식(Ⅰ)의 우라실 유도체의 금속염을 산으로 처리하여 산형태(R1=수소)로 전환시켜, R1이 수소이고 R6이 수소, 플루오르 또는 C1-4－알킬이며 R7이 C1-4－알킬인 일반식(Ⅰ)의 화합물 및 일반식(Ⅰ) 화합물의 염을 제조하거나, c) 하기 일반식 (Ⅰ´)의 우라실 유도체를 C1-4－알킬, C2-5－알켄일 또는 C3-5－알킨일기를 함유하는 알킬화제로 알킬화시켜, R1이 C1-4－알킬, C1-4－할로알킬, C2-5－알켄일 또는 C3-5－알킨일인 일반식(Ⅰ)의 화합물을 제조하거나, d) 하기 일반식(Ⅰ˝)의 우라실 유도체로부터 보호기 R10을 분리하여, R2가 수소인 일반식(Ⅰ)의 화합물을 제조하거나, e)하기 일반식(Ⅰ´˝)의 우라실 유도체를 상응하게 알킬화시켜, R2가 수소가 아닌 일반식(Ⅰ)의 화합물을 제조하거나, f) 하기 일반식(Ⅰ´˝)의 우라실 유도체를 염소화, 브롬화 또는 요오드화시켜, R6이 염소, 브롬 또는 요오드인 일반식(Ⅰ)의 화합물을 제조하거나, g) 하기 일반식(Ⅳ)의 피리미딘온 유도체를 유기 염기의 존재하에 알칸올, 알켄올 또는 알킨올 R1OH로 처리하거나, 또는 하기 일반식(Ⅴ)의 상응하는 알코올레이트, 알켄올레이트 또는 알킨올레이트로 처리하고 필요한 경우 R1이 수소이고 R2가 수소 및/또는 C2-5－카르복시알킬인 수득한 일반식(Ⅰ)의 화합물의 염으로 전환시켜, 일반식(Ⅰ)화합물의 에놀에테르를 제조한느 것을 특징으로 하는, 하기 일반식(Ⅰ)의 화합물 및 R1이 C1-4－알킬, C2-5－알켄일 또는 C3-5－알킨일인 일반식(Ⅰ) 화합물의 상응하는 에놀에테르, 및 R1이 수소이고 R2가 수소 및/또는 C2-5－카르복시알킬인 일반식(Ⅰ) 화합물의 염을 제조하는 방법:a) the compounds of formula (II) below are cyclized under basic conditions and, if necessary, converted to the acid form (R 1 = hydrogen) by treating the metal salts of the uracil derivatives of formula (I) that can be obtained with an acid. Whereby R 1 is hydrogen and R 6 is hydrogen, fluoro or C 1-4 -alkylyl compounds of formula (I) and, if necessary, metal salts of these compounds, or b) compounds of formula (III) Is cyclized under basic conditions and, if necessary, is converted to the acid form (R 1 = hydrogen) by treatment with an acid of a metal salt of the uracil derivative of general formula (I) that can be obtained, wherein R 1 is hydrogen and R 6 is Preparing a compound of formula (I) and a compound of formula (I) wherein hydrogen, fluorine or C 1-4 -alkyl and R 7 is C 1-4 -alkyl, or c) the following general formula (I ′) The uracil derivatives of are known as alkylating agents containing C 1-4 -alkyl, C 2-5 -alkenyl or C 3-5 -alkynyl groups. Chelation to prepare a compound of formula (I) wherein R 1 is C 1-4 -alkyl, C 1-4 -haloalkyl, C 2-5 -alkenyl or C 3-5 -alkynyl, or d) Separation of protecting group R 10 from uracil derivatives of general formula (I ') yields compounds of general formula (I) wherein R 2 is hydrogen, or e) corresponding alkylation of uracil derivatives of general formula (I ′') by, R 2 is prepared a compound represented by the general formula (ⅰ) other than hydrogen, or, f) to a uracil derivative represented by the general formula (ⅰ'˝) by chlorination, bromination or iodination, a normal R 6 is chlorine, bromine or iodine Preparing a compound of formula (I), or g) treating a pyrimidinone derivative of formula (IV) with alkanol, alkenol or alkynol R 1 OH in the presence of an organic base, or ) corresponding alcoholate, to know kenol rate or alkynyl if necessary treated with oleate and R 1 is hydrogen R 2 is hydrogen to the / Or C 2-5 - alkyl, carboxyl obtained was converted into a salt of Compound (Ⅰ), the following formula (Ⅰ), characterized in that the slow production of an enol ether compound of formula (Ⅰ) The compound and the corresponding enolether of the compound of formula (I) wherein R 1 is C 1-4 -alkyl, C 2-5 -alkenyl or C 3-5 -alkynyl, and R 1 is hydrogen and R 2 is hydrogen and And / or to prepare salts of compounds of formula (I) which are C 2-5 -carboxyalkyl: 상기식에서, R1은 수소, C1-4－알킬, C1-4할로알킬, C2-5알켄일 또는 C3-5알킨일이고, R2는 수소, C1-4－알킬, C1-4－할로알킬, C1-4-알콕시-C1-4-알킬 C1-4－알콕시－C1-4－알콕시－C1-4－알킬, C2-5－시아노알킬, C2-5－카르복시알킬, C2-5알콕시카르보닐－C1-4－알킬, C2-5할로알콕시카르보닐－C1-4－알킬, C1-4－알콕시－C2-5－알콕시카르보닐－C1-4－알킬, C2-5－알콕시카르보닐－C2-5－알콕시카르보닐－C1-4－알킬, C4-7－시클로알킬옥시카르보닐－C1-4－알킬, 카르바모일－C1-4－알킬, 모노(C1-4－알킬)카르바모일－C1-4－알킬, 디(C1-4－알킬)카르바모일－C1-4－알킬, C3-4－알켄일, C3-4－할로알켄일, 신나밀, C3-4－알킨일 또는 C3-4－할로알킨일이며, R3및 R4는 서로 독립적으로 수소, 할로겐, C1-4－알킬 또는 페닐이고, R5는 수소, 플루오르 또는 염소이고, R6는 수소, 할로겐 또는 C1-4－알킬이고, R7은 C1-4－알킬이거나, 또는 R1이 C1-4－할로알킬이 아닌 경우 C1-4－할로알킬일 수 있으며, n은 0 또는 1이고, X는 산소 또는 황이고, R6´은 수소, 플루오르 또는 C1-4－알킬이고, R8및 R9는 저급 알킬이며, R7´은 C1-4－알킬이고, R10은 보호기이고, Hal은 염소 또는 브롬이다.Wherein R 1 is hydrogen, C 1-4 -alkyl, C 1-4 haloalkyl, C 2-5 alkenyl or C 3-5 alkynyl, R 2 is hydrogen, C 1-4 -alkyl, C 1-4 -haloalkyl, C 1-4 -alkoxy-C 1-4 -alkyl C 1-4 -alkoxy-C 1-4 -alkoxy-C 1-4 -alkyl, C 2-5 -cyanoalkyl, C 2-5 -carboxyalkyl, C 2-5 alkoxycarbonyl-C 1-4 -alkyl, C 2-5 haloalkoxycarbonyl-C 1-4 -alkyl, C 1-4 -alkoxy-C 2-5 -Alkoxycarbonyl-C 1-4 -alkyl, C 2-5 -alkoxycarbonyl -C 2-5 -alkoxycarbonyl -C 1-4 -alkyl, C 4-7 -cycloalkyloxycarbonyl-C 1 -4 -alkyl, carbamoyl-C 1-4 -alkyl, mono (C 1-4 -alkyl) carbamoyl-C 1-4 -alkyl, di (C 1-4 -alkyl) carbamoyl-C 1-4 -alkyl, C 3-4 - alkenyl, C 3-4 - alkenyl, halo, cinnamyl, C 3-4 - alkynyl, or C 3-4-alkynyl, and halo, R 3 and R 4 are independently hydrogen, halogen, C 1-4 each other an alkyl or phenyl, R 5 is And small, fluorine or chlorine, R 6 is hydrogen, halogen or C 1-4 - alkyl, R 7 is C 1-4 - alkyl or, or R 1 is C 1-4 - is not a haloalkyl C 1- 4- haloalkyl, n is 0 or 1, X is oxygen or sulfur, R 6 ′ is hydrogen, fluorine or C 1-4 -alkyl, R 8 and R 9 are lower alkyl, R 7 Is C 1-4 -alkyl, R 10 is a protecting group and Hal is chlorine or bromine. 제15항에 있어서, 방법 a), b), c), f) 또는 g)에 의하여, 또 때에 따라서는 염으로 전환시킴으로써, 일반식(Ⅰ)의 화합물 및 그의 에놀에테르 및 염을 제조하는 것을 특징으로 하는 방법.The process according to claim 15 for preparing the compound of general formula (I) and its enolether and salts by conversion by methods a), b), c), f) or g) and optionally into salts. How to feature. 제15항에 있어서, 제1항 내지 제11항중 어느 하나에 따른 화합물을 제조하는 것을 특징으로 하는 방법.A method according to claim 15, wherein the compound according to claim 1 is prepared. 보호하고자 하는 작물을 잡초로부터 보호하고 및/또는 제1항, 제2항 및 제10항중 어느 하나에 따른 화합물 또는 제12항 또는 제13항에 따른 조성물 유효량으로 잡초를 처리하는 것을 특징으로 하는 제초방법.Weeds characterized by protecting the crops to be protected from weeds and / or by treating the weeds with a compound according to any one of claims 1, 2 and 10 or an effective amount of a composition according to claim 12. Way. 보호하고자 하는 작물을 잡초로부터 보호하고 및/또는 제3항 내지 제9항 및 제11항중 어느 하나에 따른 화합물 또는 제14항에 따른 조성물 유효량으로 잡초를 처리하는 것을 특징으로 하는 제초방법.A weeding method comprising protecting the crop to be protected from weeds and / or treating the weeds with an effective amount of the compound according to any one of claims 3 to 9 or 11 or the composition according to claim 14. 잡초를 방제하기 위한, 제1항, 제2항 및 제10항중 어느 하나에 따른 화합물 또는 제12항 또는 제13항에 따른 조성물의 용도.Use of a compound according to any one of claims 1, 2 and 10 or a composition according to claim 12 or 13 for controlling weeds. 잡초를 방제하기 위한, 제3항 내지 제9항 및 제11항중 어느 하나에 따른 화합물 또는 제14항에 따른 조성물의 용도.Use of a compound according to any one of claims 3 to 9 and 11 or a composition according to claim 14 for controlling weeds. ※ 참고사항 : 최초출원 내용에 의하여 공개되는 것임.※ Note: This is to be disclosed by the original application.
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