KR910002850A - Uracil derivatives and herbicides containing the same as active ingredients - Google Patents

Uracil derivatives and herbicides containing the same as active ingredients Download PDF

Info

Publication number
KR910002850A
KR910002850A KR1019900010635A KR900010635A KR910002850A KR 910002850 A KR910002850 A KR 910002850A KR 1019900010635 A KR1019900010635 A KR 1019900010635A KR 900010635 A KR900010635 A KR 900010635A KR 910002850 A KR910002850 A KR 910002850A
Authority
KR
South Korea
Prior art keywords
alkyl
hydrogen
alkoxy
halogen
haloalkyl
Prior art date
Application number
KR1019900010635A
Other languages
Korean (ko)
Other versions
KR0163591B1 (en
Inventor
준 사또
겐죠 후꾸다
가오루 이또
고이찌 스즈끼
쯔또무 니와마찌
시게오미 와따나베
Original Assignee
나까이 다께오
닛산 가가꾸 고교 가부시끼가이샤
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 나까이 다께오, 닛산 가가꾸 고교 가부시끼가이샤 filed Critical 나까이 다께오
Publication of KR910002850A publication Critical patent/KR910002850A/en
Application granted granted Critical
Publication of KR0163591B1 publication Critical patent/KR0163591B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/82—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 three ring hetero 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
    • A01N43/72—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • C07D413/10—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 linked by a carbon chain containing aromatic rings
    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • 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

Landscapes

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

Abstract

내용 없음.No content.

Description

우라실 유도체 및 활성성분으로서 이를 함유하는 제초제.Uracil derivatives and herbicides containing them as active ingredients.

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

Claims (12)

하기 일반식(Ⅰ)의 우라실 유도체Uracil derivatives of the general formula (I) 상기식에서, R1은 수소, C1-3알킬, 히드록시메틸 또는 C1-3할로알킬이고, R2는 C1-6할로알킬이고, R3은 수소, C1-6알킬 C1-6할로알킬, 히드록시메틸, 할로겐 또는 니트로이며, R4는 수소 또는 할로겐이고, (i)R5와 R6이 개별적으로 취해지는 경우 R5는 할로겐, 니트로또는 사이노이고, R6는 -S-B1-,, , Wherein R 1 is hydrogen, C 1-3 alkyl, hydroxymethyl or C 1-3 haloalkyl, R 2 is C 1-6 haloalkyl, R 3 is hydrogen, C 1-6 alkyl C 1- 6 haloalkyl, hydroxymethyl, halogen or nitro, R 4 is hydrogen or halogen, (i) when R 5 and R 6 are taken separately R 5 is halogen, nitro or cyno, and R 6 is- SB 1- , , , B1은 수소 C1-5알킬, C3-6시클로알킬, C2-4알켄일, C3-4알킨일, 시아노메틸, 히드록시메틸, 클로로메틸, 벤질,B 1 is hydrogen C 1-5 alkyl, C 3-6 cycloalkyl, C 2-4 alkenyl, C 3-4 alkynyl, cyanomethyl, hydroxymethyl, chloromethyl, benzyl, , CH2-Y-B23, CH2-Y-CH(B21)CO2B22, 또는이며, B21은 수소, C1-3알킬, 메틸티오, 페닐티오 또는 메톡시메틸 이고, B22는 수소, 나트륨, 칼륨, 암모늄, 이소프로필암모늄, C1-5알킬, C2-5알켄일, C3-5알킨일, C3-6시클로알킬, C3-6시클로알킬, C1-2알킬, C2-3할로알킬, 펜에틸, α-메틸벤질, 3-디메틸아미노프로필; 할로겐 C1-4알킬, C1-3알콕실, C1-2알킬아미노, 디메틸아미노, C1-2알콕시-카르보닐, C2-3아실, C1-2할로알킬 또는 C1-2할로알킬옥실로부터 선정된 치환제 1 이상에 의해 치환될 수 있는 페닐;할로겐 C1-4알킬, C1-3알콕실, C1-2알킬아미노, 디메틸아미노 C2-3아실, 트리플루오로 아세틸아미노, C1-2알콕시-카르보닐, 메틸술폰일, 트리플루오로메틸-술폰일, C1-2할로알킬 또는 C1-2할로알킬옥실로부터 선정된 치환체 1이상에 이해 치환될 수 있는 벤질이며, n은 1내지 4의 정수이고, B23은 수소, C1-5알킬, 시아노메틸, C2-5아실, 클로로아세킬 또는 디메틸카르바모일이고, Y는 산소 또는 황이며, D21은 수소, C1-3알킬, C1-3알콕시 또는 C1-3알콕시, C1-2알킬이고, D22는 수소, C1-4알킬, C3-6시클로알킬, C2-3할로알킬, 페닐 또는 벤질이며, D23은 수소 또는 C1-3알킬이고, D24는 수소, C1-3알킬 또는 C1-3알콕시 C1-2알킬이고, Z는 산소, 황또는 NH이고, D25는 수소, 나트륨, C1-4알킬, C2-5알켄일, C3-5알킨일, C2-5아실, C1-4알킬술폰일 또는 C1-3알콕시 C1-2알킬이며, D26은 C1-4알킬 또는 C1-3할로알킬이고, D27은 수소 C1-6알킬, C3-6시클로알킬, C1-3할로알킬, C1-4알콕실, C1-4알킬티오, C1-4알콕시-카르보닐, 메르갑토, 히르록실, C1-3알콕시-C1-2알킬, C1-4알킬아미노, ND28(D29), 디메틸카르바모일, CONHSO2CH3, C1-4알킬술폰일, 또는 N(D30)SO2D31이며, D28및 D29는 독립적으로 C1-4알킬이고, D30은 수소, 나트륨, C1-4알킬, C1-4알킬술폰일, C1-3알콕시-C1-2알킬이고, D31은 C1-4알킬 또는 C1-3할로알킬이고, D32는 C1-6알킬 또는 C3-6시클로알킬이며, D33,D34및 D35는 독립적으로 수소 또는 C1-6알킬이고, D36및 D37은 독립적으로 수소, C1-6알킬 또는 디메틸아미노이며, D38은 수소, 할로겐, 메르갑토, 히드록실, C1-6알킬,C3-6시클로알킬, C1-3할로알킬 C1-4알콕실, C1-4알킬티오, C1-4알콕시-카르보닐, 디메틸카르바모일, C1-3알콕시-C1-2알킬, C1-4알킬아미노, ND28(D29), CONHSO2CH3,C1-4알킬술폰일, 페닐,벤질 또는 N(D39)SO2D31이며, D39는 수소, C1-4알킬, 니트륨, 칼륨, C1-4알킬술폰일 또는 C1-5알콕시-C1-2알킬이고, D40은 수소, C1-6알킬, C3-6시클로알킬, 페닐, 벤질 또는 2-피리딜이고, D41은 수소, 할로겐, 메르캅토, 히드록실, 아미노, C1-6알킬 C1-4알킬아미노, ND28(D29), C1-4알킬티오, CO2D28, C1-4알킬술폰일, C1-4알콕실 또는 N(D39)SO2D31이며 D42는 수소, 할로겐, 니트로, 아미노, 시아노, C1-4알킬아미노, N(D28)D29, C1-4알킬카르보닐 또는 C1-4알콕시-카르보닐이며, D43은 수소, 히드록실, 메톡시, 아미노, 벤조일 또는 C1-4알킬이고, D44는 수소, 시아노, 아세틸, C1-4알킬, 카르복실 또는 C1-4알콕시-카르보닐이고, D45및 D46은 독립적으로 수소, 페닐, 히드록실, 메톡시 또는 C1-4알킬이며, D47및 D48은 독립적으로 수소 또는 C1-4알킬이고, X는 산소 또는 황이고, (ⅱ) R5와 R6이 고리를 형성하는 경우, 상기 우라실 유도체는 일반식 , CH 2 -YB 23 , CH 2 -Y-CH (B 21 ) CO 2 B 22 , or B 21 is hydrogen, C 1-3 alkyl, methylthio, phenylthio or methoxymethyl, B 22 is hydrogen, sodium, potassium, ammonium, isopropylammonium, C 1-5 alkyl, C 2-5 al Kenyl, C 3-5 alkynyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl, C 1-2 alkyl, C 2-3 haloalkyl, phenethyl, α-methylbenzyl, 3-dimethylaminopropyl; Halogen C 1-4 alkyl, C 1-3 alkoxyl, C 1-2 alkylamino, dimethylamino, C 1-2 alkoxy-carbonyl, C 2-3 acyl, C 1-2 haloalkyl or C 1-2 Phenyl which may be substituted by one or more substituents selected from haloalkyloxyl; halogen C 1-4 alkyl, C 1-3 alkoxyl, C 1-2 alkylamino, dimethylamino C 2-3 acyl, trifluoro May be substituted with one or more substituents selected from acetylamino, C 1-2 alkoxy-carbonyl, methylsulfonyl, trifluoromethyl-sulfonyl, C 1-2 haloalkyl or C 1-2 haloalkyloxyl Benzyl, n is an integer from 1 to 4, B 23 is hydrogen, C 1-5 alkyl, cyanomethyl, C 2-5 acyl, chloroacetyl or dimethylcarbamoyl, Y is oxygen or sulfur, D 21 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy or C 1-3 alkoxy, C 1-2 alkyl, D 22 is hydrogen, C 1-4 alkyl, C 3-6 cycloalkyl, C 2 -3 haloalkyl, and phenyl or benzyl, D 23 is hydrogen Is C 1-3 alkyl, D 24 is hydrogen, C 1-3 alkyl or C 1-3 alkoxy C 1-2 alkyl, Z is oxygen, sulfur or NH, D 25 is hydrogen, sodium, C 1- 4 alkyl, C 2-5 alkenyl, C 3-5 alkynyl, C 2-5 acyl, C 1-4 alkylsulfonyl or C 1-3 alkoxy C 1-2 alkyl, D 26 is C 1-4 Alkyl or C 1-3 haloalkyl, D 27 is hydrogen C 1-6 alkyl, C 3-6 cycloalkyl, C 1-3 haloalkyl, C 1-4 alkoxyl, C 1-4 alkylthio, C 1 -4 alkoxy-carbonyl, mercapto, hydroxyl, C 1-3 alkoxy-C 1-2 alkyl, C 1-4 alkylamino, ND 28 (D 29 ), dimethylcarbamoyl, CONHSO 2 CH 3 , C 1-4 alkylsulfonyl, or N (D 30 ) SO 2 D 31 , D 28 and D 29 are independently C 1-4 alkyl, D 30 is hydrogen, sodium, C 1-4 alkyl, C 1- 4 alkylsulfonyl, C 1-3 alkoxy-C 1-2 alkyl, D 31 is C 1-4 alkyl or C 1-3 haloalkyl, D 32 is C 1-6 alkyl or C 3-6 cycloalkyl And D 33, D 34 and D 35 are independently hydrogen or C 1 -6 alkyl, D 36 and D 37 are independently hydrogen, C 1-6 alkyl or dimethylamino, D 38 is hydrogen, halogen, mercapto, hydroxyl, C 1-6 alkyl, C 3-6 cycloalkyl , C 1-3 haloalkyl C 1-4 alkoxyl, C 1-4 alkylthio, C 1-4 alkoxy-carbonyl, dimethylcarbamoyl, C 1-3 alkoxy-C 1-2 alkyl, C 1- 4 alkylamino, ND 28 (D 29 ), CONHSO 2 CH 3, C 1-4 alkylsulfonyl, phenyl, benzyl or N (D 39 ) SO 2 D 31 , D 39 is hydrogen, C 1-4 alkyl, Nitrile, potassium, C 1-4 alkylsulfonyl or C 1-5 alkoxy-C 1-2 alkyl, D 40 is hydrogen, C 1-6 alkyl, C 3-6 cycloalkyl, phenyl, benzyl or 2- Pyridyl, D 41 is hydrogen, halogen, mercapto, hydroxyl, amino, C 1-6 alkyl C 1-4 alkylamino, ND 28 (D 29 ), C 1-4 alkylthio, CO 2 D 28 , C 1-4 alkylsulfonyl, C 1-4 alkoxyl or N (D 39 ) SO 2 D 31 and D 42 is hydrogen, halogen, nitro, amino, cyano, C 1-4 alkylamino, N (D 28 ) D 29, C 1-4 Kill-carbonyl or C 1-4 alkoxy-carbonyl, and, D 43 is hydrogen, hydroxyl, methoxy, and amino, benzoyl or C 1-4 alkyl, D 44 is hydrogen, cyano, acetyl, C 1-4 Alkyl, carboxyl or C 1-4 alkoxy-carbonyl, D 45 and D 46 are independently hydrogen, phenyl, hydroxyl, methoxy or C 1-4 alkyl, and D 47 and D 48 are independently hydrogen or C 1-4 alkyl, X is oxygen or sulfur, and (ii) when R 5 and R 6 form a ring, the uracil derivative is of the general formula 이고, A1은 수소 및 C1-4알킬이고, A2는 수소, C1-5알킬, C2-5알켄일, C3-5알킨일, C3-6시클로알킬-C1-2알킬, C1-6할로알킬, C1-6할로알켄일, C1-6할로알킨일, 시아노메틸, 히드록시메틸, 클로로메틸, C1-3알콕시-C1-2알킬, -CH2CO2A21, -CH2CON(A22)A23;C1-4알킬, C1-4할로알킬, C1-4알콕시 또는 할로겐에 의해 치환될 수 있는 페닐; C1-4알킬, C1-4할로알킬, C1-4알콕시, C1-4알콕 카르보닐, C1-3알콕시-C1-2알킬 또는 할로겐에 의해 치환될수 있는 벤질 ; 또는 -CH2A24이며, A21은 수소, C1-5알킬, 나트륨, 할로겐에 의해 치환될 수 있는 페닐, 또는 할로겐에 의해 치환될 수 있는 벤질이고, A22및 A23은 독립적으로 수소 또는 C알킬이고, A24는 C1-4알킬 또는 할로겐에 의해 치환될 수 있는 2-피리딜;C1-4알킬 또는 할로겐에 의해 치환될수 있는 2-피리다질;3-이소티아졸 또는 3-이소옥사졸이며, J는 수소 C1-4알킬, C2-4알켄일, C3-4알킨일, 히드록시메틸, 클로로메틸, 카르바모일메틸, 시아노메틸, C1-4알콕시-카르보닐메틸,,C3-6시클로알킬,,C3-6시클로알킬-C1-2알킬;C1-2알콕시-C1-2알킬;C1-4알킬, C1-4알콕시, C1-4알콕시-카르보닐, C1-4알콕시-C1-2알킬 또는 할로겐에 의해 치환될 수 있는 페닐; 또는 C1-4알킬, C1-4알콕시, C1-4알콕시-카르보닐, C1-4알콕시-C1-2알킬 또는 할로겐에 의해 치환될 수 있는 벤질이다., A 1 is hydrogen and C 1-4 alkyl, A 2 is hydrogen, C 1-5 alkyl, C 2-5 alkenyl, C 3-5 alkynyl, C 3-6 cycloalkyl-C 1-2 Alkyl, C 1-6 haloalkyl, C 1-6 haloalkenyl, C 1-6 haloalkynyl, cyanomethyl, hydroxymethyl, chloromethyl, C 1-3 alkoxy-C 1-2 alkyl, -CH 2 CO 2 A 21 , —CH 2 CON (A 22 ) A 23 ; C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy or phenyl which may be substituted by halogen; Benzyl which may be substituted by C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy, C 1-4 alkoxy carbonyl, C 1-3 alkoxy-C 1-2 alkyl or halogen; Or —CH 2 A 24 , A 21 is hydrogen, C 1-5 alkyl, sodium, phenyl which may be substituted by halogen, or benzyl which may be substituted by halogen, and A 22 and A 23 are independently hydrogen or a C alkyl, a 24 is C 1-4 alkyl, or a 2-pyridyl which may be substituted by a halogen; C 1-4 alkyl or halogen multiple material 2-pyridyl which can be substituted by; 3-isothiazole or 3 Isoxoxazole, J is hydrogen C 1-4 alkyl, C 2-4 alkenyl, C 3-4 alkynyl, hydroxymethyl, chloromethyl, carbamoylmethyl, cyanomethyl, C 1-4 alkoxy- Carbonylmethyl, C 3-6 cycloalkyl, , C 3-6 cycloalkyl-C 1-2 alkyl; C 1-2 alkoxy-C 1-2 alkyl; C 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkoxy-carbonyl, C 1- Phenyl which may be substituted by 4 alkoxy-C 1-2 alkyl or halogen; Or benzyl which may be substituted by C 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkoxy-carbonyl, C 1-4 alkoxy-C 1-2 alkyl or halogen. 제1항에 있어서, 상기 우라실 유도체가 하는 하기 일반식(Ⅱ)로 나타내어지는 우라실 유도체;The uracil derivative according to claim 1, wherein the uracil derivative is represented by the following general formula (II); 상기식에서, R1은 수소, C1-3알킬, 히드록시메틸 또는 할로메틸이고, R2는 C1-6할로알킬이며, R3은 수소, C1-6알킬, C1-6할로알킬, 히드록시메틸, 할로겐 또는 니트로 이고, R4는 수소 또는 할로겐이고, A1은 수소 또는 C1-4알킬이고, A2는 수소, C1-5알킬, C2-5알켄일, C3-5알킨일, C3-6시클로알킬-C1-2알킬, C1-6할로알킬, C1-6할로알켄일, C1-6할로알킨일, 시아노메틸, 히드록시메틸, 클로로메틸, C1-3알콕시-C1-2알킬-CH2CO2A21,-CH2CON(A22)A23;C1-4알킬, C1-4할로알킬, C1-4알콕실 또는 할로겐에 의해 치환될 수 있는 페닐;C1-4알킬, C1-4할로알킬, C1-4알콕실, C1-4알콕시-카르보닐, C1-3알콕시-C1-2알킬 또는 할로겐에 의해 치환될수 있는 벤질; 또는 -CH2A24이고 A21은 수소, C1-5알킬, 나트륨, 할로겐에 의해 치환될 수 있는 페닐;또는 할로겐에 의해 치환될수 있는 벤질이며, A22및 A23은 독립적으로 수소 또는 C1-3알킬이고, A24는 C1-4알킬 또는 할로겐에 의해 치환될수 있는 2-피리딜; C1-4알킬 또는 할로겐에 의해 치환될 수 있는 2-피리다질;3-이소티아졸 또는 3-이소옥사졸이며, X는 산소 또는 황이다.Wherein R 1 is hydrogen, C 1-3 alkyl, hydroxymethyl or halomethyl, R 2 is C 1-6 haloalkyl, R 3 is hydrogen, C 1-6 alkyl, C 1-6 haloalkyl , Hydroxymethyl, halogen or nitro, R 4 is hydrogen or halogen, A 1 is hydrogen or C 1-4 alkyl, A 2 is hydrogen, C 1-5 alkyl, C 2-5 alkenyl, C 3 -5 alkynyl, C 3-6 cycloalkyl-C 1-2 alkyl, C 1-6 haloalkyl, C 1-6 haloalkenyl, C 1-6 haloalkinyl, cyanomethyl, hydroxymethyl, chloro Methyl, C 1-3 alkoxy-C 1-2 alkyl-CH 2 CO 2 A 21, -CH 2 CON (A 22 ) A 23 ; C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 al Phenyl which may be substituted by coxyl or halogen; C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxyl, C 1-4 alkoxy-carbonyl, C 1-3 alkoxy-C 1-2 Benzyl, which may be substituted by alkyl or halogen; Or —CH 2 A 24 and A 21 is hydrogen, C 1-5 alkyl, sodium, phenyl which may be substituted by halogen; or benzyl which may be substituted by halogen, A 22 and A 23 are independently hydrogen or C 1-3 alkyl, A 24 is 2-pyridyl, which may be substituted by C 1-4 alkyl or halogen; 2-pyridazyl, which may be substituted by C 1-4 alkyl or halogen; 3-isothiazole or 3-isoxazole, X is oxygen or sulfur. 제1항에 있어서, 상기 우라실 유도체가 하기 일반식(Ⅲ)으로 나타내어지는 우라실 유도체;The uracil derivative according to claim 1, wherein the uracil derivative is represented by the following general formula (III); 상기식에서, R1은 수소, C1-3알킬, 히드록시메틸 또는 할로메틸이고, R2는 C1-6할로알킬이고, R3은 수소, C1-6알킬, C1-6할로알킬, 히드록시메틸, 할로겐 또는 니트로 이며, R4는 수소 또는 할로겐이고, R5는 할로겐, 니트로 또는 시아노이고, B1은 수소, C1-5알킬, C3-6시클로알킬, C2-4알켄일, C3-4알킨일, 시아노메틸, 히드록시메틸,Wherein R 1 is hydrogen, C 1-3 alkyl, hydroxymethyl or halomethyl, R 2 is C 1-6 haloalkyl, R 3 is hydrogen, C 1-6 alkyl, C 1-6 haloalkyl , Hydroxymethyl, halogen or nitro, R 4 is hydrogen or halogen, R 5 is halogen, nitro or cyano, B 1 is hydrogen, C 1-5 alkyl, C 3-6 cycloalkyl, C 2- 4 alkenyl, C 3-4 alkynyl, cyanomethyl, hydroxymethyl, 클로로메틸, 벤질,,CH2-Y-B23, CH2-Y-CH(B21)CO2B22, 또는이며, B21은 수소, C1-3알킬, 메틸티오, 페닐티오 또는 메톡시메틸이고, B22는 수소, 나트륨,칼륨,암모늄,이소프로필아모늄, C1-5알킬, C2-5알켄일, C3-5알킨일, C3-6시클로알킬, C3-6시클로알킬, C1-2알킬, C2-3할로알킬, 펜에틸, α- 메틸벤질, 3-디메틸아미노프로필;할로겐, C1-4알킬, C1-3알콕실, C1-2알킬아미노, 디메틸아미노, C1-2알콕시-카르보닐, C2-3아실, C1-2할로알킬, 또는 C1-2할로알킬옥실로부터 선정된 치환체 1 이상에 의해 치환될 수 있는 페닐;할로겐,C1-4알킬, C1-3알콕실, C1-2알킬아미노, 디메틸아미노, C2-3아실, 트리풀루오로아세틸아미노, C1-2알콕시-카르보닐 메틸술폰일, 트리플루오로메틸-술폰일, C1-2할로알킬 또는 C1-2할로알킬옥실로부터 선정된 1이상의 치환체로 치환될 수 있는 벤질이며, n은 1내지 4의 정수이고, B23은 수소, C1-5알킬, 시아노메틸, C2-5아실, 클로로아세틸 또는 디메틸카르바모일이고, X 및 Y는 산소 또는 황이다.Chloromethyl, benzyl, , CH 2 -YB 23 , CH 2 -Y-CH (B 21 ) CO 2 B 22 , or B 21 is hydrogen, C 1-3 alkyl, methylthio, phenylthio or methoxymethyl, B 22 is hydrogen, sodium, potassium, ammonium, isopropylmonium, C 1-5 alkyl, C 2-5 Alkenyl, C 3-5 alkynyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl, C 1-2 alkyl, C 2-3 haloalkyl, phenethyl, α-methylbenzyl, 3-dimethylaminopropyl Halogen, C 1-4 alkyl, C 1-3 alkoxyl, C 1-2 alkylamino, dimethylamino, C 1-2 alkoxy-carbonyl, C 2-3 acyl, C 1-2 haloalkyl, or C Phenyl which may be substituted by one or more substituents selected from 1-2 haloalkyloxyl; halogen, C 1-4 alkyl, C 1-3 alkoxyl, C 1-2 alkylamino, dimethylamino, C 2-3 acyl , At least one substituent selected from trifluuroacetylamino, C 1-2 alkoxy-carbonyl methylsulfonyl, trifluoromethyl-sulfonyl, C 1-2 haloalkyl or C 1-2 haloalkyloxyl benzyl which may be, n is an integer from 1 to 4, B is 23 Cattle, C 1-5 alkyl, cyanomethyl, C 2-5 acyl, chloro-acetyl, or dimethylcarbamoyl, X and Y are oxygen or sulfur. 제1항에 있어서, 상기 우라실 유도체가 하기 일반식(Ⅳ)로 나타내어지는 우라실 유도체;The uracil derivative according to claim 1, wherein the uracil derivative is represented by the following general formula (IV); 상기식에서, R1은 수소, C1-3알킬 또는 C1-3할로알킬이고, R2는 C1-6할로알킬이고, R3은 수소, C1-6알킬, C1-6할로알킬, 히드록시메틸, 할로겐 또는 니트로이며, R4는 수소 또는 할로겐이고, (ⅰ)R5와 D1을 개별적으로 취하는 경우, R5는 할로겐, 니트로 또는 시아노이고, D1은 -S-B-1, Wherein R 1 is hydrogen, C 1-3 alkyl or C 1-3 haloalkyl, R 2 is C 1-6 haloalkyl, R 3 is hydrogen, C 1-6 alkyl, C 1-6 haloalkyl , Hydroxymethyl, halogen or nitro, R 4 is hydrogen or halogen, (iii) when R 5 and D 1 are taken separately, R 5 is halogen, nitro or cyano and D 1 is -SB- 1 , D21은 수소, C1-3알킬, C1-3알콕시 또는 C1-3알콕시, C1-2알킬이고, D22은 수소, C1-4알킬, C3-6시클로알킬, C2-3할로알킬, 페닐 또는 벤질이고, D23은 수소 또는 C1-3알킬이고, D24는 수소, C1-3알킬 또는 C1-3알콕시 C1-2알킬이고, Z는 산소, 황 또는 NH이고, D25는 수소, 나트륨, C1-4알킬, C2-5알켄일, C3-5알킨일, C2-5아실, C1-4알킬술폰일 또는 C1-3알콕시 C1-2알킬이며, D26은 C1-4알킬 또는 C1-3할로알킬이고, D27은 수소, C1-6알킬, C3-6시클로알킬, C1-3할로알킬, C1-4알콕실, C1-4알킬티오, C1-4알콕시-카르보닐, 메르캅토, 히드록실, C1-3알콕시-C1-2알킬, C1-4알킬아미노, ND28(D29), 디메틸카르바모일, CONNHSO2CH3, C1-4알킬술폰일, 또는 N(D30)SO2D31이며, D28및 D29는 독립적으로 C1-4알킬이고, D30은 수소, 나트륨, C1-4알킬, C1-4알킬술폰일, C1-3알콕시-C1-2알킬이고, D31은 C1-4알킬 또는 C1-3할로알킬이고, D32는 C1-6알킬 또는 C3-6시클로알킬이고, D33, D34및 D35는 독립적으로 수소 또는 C1-6알킬이고, D36및 D37은 독립적으로 수소, C1-6알킬 또는 디메틸아미노이며, D35은 수소, 할로겐, 메르캅토, 히드록실, C1-6알킬, C3-6시클로알킬, C1-3할로알킬, C1-4알콕실, C1-4알킬티오, C1-4알콕실-카르보닐, 디메틸카르바모일, C1-3알콕실-C1-2알킬, C1-4알킬아미노, ND28(D29), CONNHSO2CH3, C1-4알킬술폰일, 페닐, 벤질 또는 N(D39)SO2D31이며, D39는 수소, C1-4알킬, 니트륨, 칼륨, C1-4알킬술폰일 또는 C1-3알콕시-C1-2알킬이고, D48은 수소, C1-6알킬, C3-6시클로알킬, 페닐, 벤질 또는 2-피리딜이고, D41은 수소, 할로겐, 메르캅토, 히드록실, 아미노, C1-6알킬, C1-4알킬아미노, ND28(D29), C1-4알킬티오, CO2D28,C1-4알킬술폰일, C1-4알콕실 또는 N(D39)SO2D31이며, D42는 수소, 할로겐, 니트로, 아미노, 시아노, C1-4알킬아미노, N(D28)D29, C1-4알킬카르보닐 또는 C1-4알콕시-카르보닐이며 D43은 수소, 히드록실, 메톡시, 아미노, 벤조일 또는 C1-4알킬이며, D44는 수소, 사이노, 아세틸, C1-4알킬, 카르복실 또는 C1-4알콕시-카르보닐이며, D45및 D46은 독립적으로 수소, 페닐, 히드록실, 메톡시 또는 C1-4알킬이며, D47및 D48은 독립적으로 수소 또는 C1-4알킬이고, X는 산소 또는 황이고, (ⅱ)R5와 R1이 고리를 형성하는 경우, 상기 우라실 유도체는 일반D 21 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy or C 1-3 alkoxy, C 1-2 alkyl, D 22 is hydrogen, C 1-4 alkyl, C 3-6 cycloalkyl, C 2 -3 haloalkyl, phenyl or benzyl, D 23 is hydrogen or C 1-3 alkyl, D 24 is hydrogen, C 1-3 alkyl or C 1-3 alkoxy C 1-2 alkyl, Z is oxygen, sulfur Or NH, D 25 is hydrogen, sodium, C 1-4 alkyl, C 2-5 alkenyl, C 3-5 alkynyl, C 2-5 acyl, C 1-4 alkylsulfonyl or C 1-3 alkoxy C 1-2 alkyl, D 26 is C 1-4 alkyl or C 1-3 haloalkyl, D 27 is hydrogen, C 1-6 alkyl, C 3-6 cycloalkyl, C 1-3 haloalkyl, C 1-4 alkoxyl, C 1-4 alkylthio, C 1-4 alkoxy-carbonyl, mercapto, hydroxyl, C 1-3 alkoxy-C 1-2 alkyl, C 1-4 alkylamino, ND 28 ( D 29 ), dimethylcarbamoyl, CONNHSO 2 CH 3 , C 1-4 alkylsulfonyl, or N (D 30 ) SO 2 D 31 , D 28 and D 29 are independently C 1-4 alkyl, D 30 is hydrogen, sodium, C 1-4 alkyl, C 1-4 alkylsulphate Phonyl, C 1-3 alkoxy-C 1-2 alkyl, D 31 is C 1-4 alkyl or C 1-3 haloalkyl, D 32 is C 1-6 alkyl or C 3-6 cycloalkyl, D 33 , D 34 and D 35 are independently hydrogen or C 1-6 alkyl, D 36 and D 37 are independently hydrogen, C 1-6 alkyl or dimethylamino, D 35 is hydrogen, halogen, mercapto, hydroxide Hydroxyl, C 1-6 alkyl, C 3-6 cycloalkyl, C 1-3 haloalkyl, C 1-4 alkoxyl, C 1-4 alkylthio, C 1-4 alkoxyl-carbonyl, dimethylcarbamoyl , C 1-3 alkoxyl-C 1-2 alkyl, C 1-4 alkylamino, ND 28 (D 29 ), CONNHSO 2 CH 3 , C 1-4 alkylsulfonyl, phenyl, benzyl or N (D 39 ) SO 2 D 31 , D 39 is hydrogen, C 1-4 alkyl, nitrile, potassium, C 1-4 alkylsulfonyl or C 1-3 alkoxy-C 1-2 alkyl, D 48 is hydrogen, C 1 -6 alkyl, C 3-6 cycloalkyl, phenyl, benzyl or 2-pyridyl, D 41 is hydrogen, halogen, mercapto, hydroxyl, amino, C 1-6 alkyl, C 1-4 alkylamino, ND 2 8 (D 29 ), C 1-4 alkylthio, CO 2 D 28, C 1-4 alkylsulfonyl, C 1-4 alkoxyl or N (D 39 ) SO 2 D 31 , and D 42 is hydrogen, halogen , Nitro, amino, cyano, C 1-4 alkylamino, N (D 28 ) D 29 , C 1-4 alkylcarbonyl or C 1-4 alkoxy-carbonyl and D 43 is hydrogen, hydroxyl, methoxy , Amino, benzoyl or C 1-4 alkyl, D 44 is hydrogen, cyno, acetyl, C 1-4 alkyl, carboxyl or C 1-4 alkoxy-carbonyl, D 45 and D 46 are independently hydrogen , Phenyl, hydroxyl, methoxy or C 1-4 alkyl, D 47 and D 48 are independently hydrogen or C 1-4 alkyl, X is oxygen or sulfur, (ii) R 5 and R 1 are rings When forming the uracil derivatives are common J는 수소 C1-4알킬, C2-4알켄일, C3-4알킨일, 히드록시메틸, 클로로메틸,카르바모일메틸,시아노메틸, C1-4알콕시-카르보닐메틸,, C3-6시클로알킬,,C3-6시클로알킬-C1-2알킬;C1-2알콕시-C1-2알킬;C1-4알킬, C1-4알콕시C1-4알콕시-C1-4카르보닐, C1-4알콕시-C1-2알킬 또는 할로겐에 의해 치환될 수 있는 페닐;또는 C1-4알킬, C1-4알콕실, C1-4알콕시-카르보닐, C1-4알콕시 C1-2알킬 또는 할로겐에 의해 치환될 수 있는 벤질이다.J is hydrogen C 1-4 alkyl, C 2-4 alkenyl, C 3-4 alkynyl, hydroxymethyl, chloromethyl, carbamoylmethyl, cyanomethyl, C 1-4 alkoxy-carbonylmethyl, , C 3-6 cycloalkyl, , C 3-6 cycloalkyl-C 1-2 alkyl; C 1-2 alkoxy-C 1-2 alkyl; C 1-4 alkyl, C 1-4 alkoxyC 1-4 alkoxy-C 1-4 carbonyl, C 1-4 alkoxy-C 1-2 alkyl or phenyl which may be substituted by halogen; or C 1-4 alkyl, C 1-4 alkoxyl, C 1-4 alkoxy-carbonyl, C 1-4 alkoxy C Benzyl which may be substituted by 1-2 alkyl or halogen. 제1항에 우라실 유도체 제초 유효량 및 허용가능한 담체 또는 희석제를 포함하는 제초성 조성물.A herbicidal composition comprising the herbicidal effective amount of the uracil derivative and an acceptable carrier or diluent according to claim 1. 제5항에 있어서, 상기 우라실 유도체가 제2항의 화합물인 제초성 조성물.The herbicidal composition of claim 5, wherein the uracil derivative is the compound of claim 2. 제5항에 있어서, 상기 우라실 유도체가 제3항의 화합물인 제초성 조성물.The herbicidal composition of claim 5, wherein the uracil derivative is the compound of claim 3. 제5항에 있어서, 상기 우라실 유도체가 제4항의 화합물인 제초성 조성물.The herbicidal composition of claim 5, wherein the uracil derivative is the compound of claim 4. 제1항의 우라실 유도체 제초 유효량을 투여하는 것을 포함하는, 잡초를 죽이거나 또는 잡초의 생장을 억제하는 방법.A method of killing or inhibiting weed growth, comprising administering an effective amount of the uracil derivative herbicide of claim 1. 제9항에 있어서, 상기 우라실 유도체가 제2항의 화합물인 방법.The method of claim 9, wherein said uracil derivative is a compound of claim 2. 제9항에 있어서, 상기 우라실 유도체가 제3항의 화합물인 방법.10. The method of claim 9, wherein said uracil derivative is a compound of claim 3. 제9항에 있어서, 상기 우라실 유도체가 제4항의 화합물인 방법.The method of claim 9, wherein said uracil derivative is a compound of claim 4. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019900010635A 1989-07-14 1990-07-13 Uracil derivatives and herbicides containing the same as active ingredient KR0163591B1 (en)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
JP181824/89 1989-07-14
JP18182489 1989-07-14
JP18706589 1989-07-19
JP187065/89 1989-07-19
JP27466289 1989-10-20
JP274662/89 1989-10-20
JP168683/90 1990-06-27
JP16868390A JP2946656B2 (en) 1989-07-14 1990-06-27 Uracil derivative and herbicide

Publications (2)

Publication Number Publication Date
KR910002850A true KR910002850A (en) 1991-02-26
KR0163591B1 KR0163591B1 (en) 1998-12-01

Family

ID=27325077

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019900010635A KR0163591B1 (en) 1989-07-14 1990-07-13 Uracil derivatives and herbicides containing the same as active ingredient

Country Status (2)

Country Link
JP (1) JP2946656B2 (en)
KR (1) KR0163591B1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160135102A (en) * 2015-05-14 2016-11-24 씨제이제일제당 (주) Feed additives comprising lysine derivatives
US11708591B2 (en) 2018-01-31 2023-07-25 Cj Cheiljedang Corporation Method for preparing natural L-cysteine crystals by continuous chromatography

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4131038A1 (en) * 1991-09-20 1993-04-01 Basf Ag SUBSTITUTED 3-PHENYLURAZILES
JP3525499B2 (en) * 1994-07-25 2004-05-10 日産化学工業株式会社 Solid pesticide composition
JPH08157312A (en) * 1994-12-02 1996-06-18 Nippon Bayeragrochem Kk Herbicide for paddy rice field
AU701851B2 (en) * 1995-06-29 1999-02-04 Bayer Aktiengesellschaft Substituted cyanophenyluracils
AU2651297A (en) * 1996-05-08 1997-11-26 Ihara Chemical Industry Co. Ltd. Indolyl-substituted uracil derivatives and herbicides comprising them as active ingredients
CA2928061C (en) 2001-10-19 2018-10-16 Sumitomo Chemical Company, Limited Weed controller metabolism proteins, genes thereof and use of the same
ITMI20022758A1 (en) * 2002-12-23 2004-06-24 Isagro Ricerca Srl NEW URACILI HERBICIDE ACTIVITIES.
KR102497229B1 (en) 2020-10-20 2023-02-06 주식회사 완성 Method and system for predicting a lifetime of Organic Light Emitting Diodes

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160135102A (en) * 2015-05-14 2016-11-24 씨제이제일제당 (주) Feed additives comprising lysine derivatives
US11708591B2 (en) 2018-01-31 2023-07-25 Cj Cheiljedang Corporation Method for preparing natural L-cysteine crystals by continuous chromatography

Also Published As

Publication number Publication date
KR0163591B1 (en) 1998-12-01
JPH03204865A (en) 1991-09-06
JP2946656B2 (en) 1999-09-06

Similar Documents

Publication Publication Date Title
IL114391A (en) 2[1',2',4'-triazole-3'-yloxymethylene] benzene derivatives, compositions for controlling animal pests or harmful fungi comprising 2-[1',2',4'-triazole-3'-yloxymethylene] anilides and their preparation
YU47098B (en) SUBSTITUTED THIAZOLES AND THEIR USE AS FUNGICIDES
IL110703A0 (en) Intermediates to 4-benzoyl isoxazole derivatives
ES8304944A1 (en) Aminopyrimidine derivatives, processes for their preparation, and fungicidal, insecticidal and acaricidal compositions containing them.
KR910002850A (en) Uracil derivatives and herbicides containing the same as active ingredients
KR850007975A (en) Method for preparing 6-chlorobenzazolyloxyacetamide
NZ218806A (en) 1-arylpyrazoles and pesticidal compositions
KR890002154A (en) 6,7-dihydropyrazolo (1,5-a) (1,3,5) triazine-2-sulfonamide, process for its preparation and use as herbicide and plant growth regulator
KR890002109A (en) Herbicidally active aryloxy saturated 5-sided benzo fused hetero-cyclic compounds, compositions containing them and their use
GR3005022T3 (en)
KR940021549A (en) Dihydrobenzofuran Derivatives, Methods of Making and Uses
KR970704715A (en) Saccharin Derivatives
KR920000756A (en) Pyrazolecarboxamides, insecticidal and acaricide compositions, and fungicidal compositions useful for agriculture and horticulture
DE3876314D1 (en) SUBSTITUTED IMIDAZOLONE WITH HERBICIDAL EFFECT.
ATE15192T1 (en) 2-(2-HALO-4-(6-HALOQUINOXALINE-2YLOXY)PHENOXY)PROPIONS|URE-DERIVATES, PROCESSES FOR THEIR PRODUCTION, HERBICIDE COMPOSITIONS CONTAINING THEM, AND THEIR USE AS HERBICIDES.
DE59303444D1 (en) CYCLOHEXENONOXIMETHER, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS HERBICIDES
JPS5446749A (en) Cyclohexane derivative, its preparation, and herbicides
EP0136016A3 (en) N-(substituted)-5-(substituted phenyl)-1,3-oxazolidines: herbicidal antidotes
BG48803A3 (en) Herbicide means
KR910014357A (en) Novel substituted β-pyrimidinyloxy (thio)-and β-triazinyloxy (thio) cycloalkanecarboxylic acid derivatives, methods for their preparation, and use as herbicides, fungicides and plant growth regulators
IL75313A (en) Compositions comprising acylamide derivatives for protecting culture plants from the phytotoxic action of herbicidal chloracetanilides
KR950014106A (en) Novel thiophenesulfonylurea derivatives, preparation method thereof and use as herbicide
GB1436214A (en) Amido containing phosphorothiolate pesticide
KR830003440A (en) Method of manufacturing herbicides
KR900004343A (en) Pyrazolopyridine For Epilepsy Treatment

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20050824

Year of fee payment: 8

LAPS Lapse due to unpaid annual fee