KR950000670A - 살진균성 광학 활성 2-이미다졸린-5-온 및 2-이미다졸린-5-티온 유도체 - Google Patents

살진균성 광학 활성 2-이미다졸린-5-온 및 2-이미다졸린-5-티온 유도체 Download PDF

Info

Publication number
KR950000670A
KR950000670A KR1019940013823A KR19940013823A KR950000670A KR 950000670 A KR950000670 A KR 950000670A KR 1019940013823 A KR1019940013823 A KR 1019940013823A KR 19940013823 A KR19940013823 A KR 19940013823A KR 950000670 A KR950000670 A KR 950000670A
Authority
KR
South Korea
Prior art keywords
group
carbon atoms
formula
compound
alkyl
Prior art date
Application number
KR1019940013823A
Other languages
English (en)
Other versions
KR100348201B1 (ko
Inventor
필립 바스꾸 쟝
가드라 알랭
라크르와 귀
뻬레 조셉
Original Assignee
삐에르 그랑
롱-쁠랑 아그로쉬미
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
Priority claimed from FR9307663A external-priority patent/FR2706455B1/fr
Application filed by 삐에르 그랑, 롱-쁠랑 아그로쉬미 filed Critical 삐에르 그랑
Publication of KR950000670A publication Critical patent/KR950000670A/ko
Application granted granted Critical
Publication of KR100348201B1 publication Critical patent/KR100348201B1/ko

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/61—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms not forming part of a nitro radical, attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • 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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
    • 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
    • C07C243/30—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 an unsaturated carbon skeleton
    • C07C243/32—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 an unsaturated carbon skeleton the carbon skeleton containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
    • C07C331/16—Isothiocyanates
    • C07C331/18—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms
    • C07C331/22—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
    • C07C331/24—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/70—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
    • C07D233/78—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/80—Two oxygen atoms, e.g. hydantoin with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/84—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/86—Oxygen and sulfur atoms, e.g. thiohydantoin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D417/12—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 linked by a chain containing hetero atoms as chain links

Abstract

1. 광학 활성 2－이미다졸린－5－온 및 2－이미다졸린－5－티온 유도체.
2. 이것은 하기 일반식 Ⅰ이다 :
[식중, M＝O,S 또는 임의로 할로겐화된 CH2이고, W＝O,S 또는 S＝O이며, p＝0 또는 1이고, R1,R2, 및 R4는 탄화수소, 특히 할로겐 원자로 임의로 치환된 아릴기이며, R3는 H 또는 임의로 할로겐화된 C1∼C2알킬이고, R5는 탄화수소기이다.]
3. 농경학적 살진균제로서의 용도.

Description

살진균성 광학 활성 2－이미다졸린－5－온 및 2－이미다졸린－5－티온 유도체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (17)

  1. 하기 일반식 Ⅰ의 광학활성 2－이미다졸린－5－온 또는 2－이미다졸린－5－티온 유도체 및 이들 화합물의 농경학적으로 허용가능한 염 형태 :
    [식중 : －W는 산소 또는 황 원자 또는 S＝O기를 나타내고 ; －M은 산소 또는 황 원자, 또는 임의로 할로겐화된 CH2기를 나타내고 ; －P는 0 또는 1의 정수이며 ; ＊ 는 입체 특이적 배열에 상응하는 부제 탄소원자를 의미하고 ; －R1및 R2는 상이하며 하기를 나타내고 ; －탄소수 1 내지 6을 함유하는 알킬 또는 할로알킬기 또는 －탄소수 2 내지 6을 함유하는 알콕시알킬, 알킬티오알킬, 알킬술포닐알킬, 모노알킬아미노알킬, 알케닐 또는 알키닐기 또는 －탄소수 3 내지 7을 함유하는 디알킬아미노알킬 또는 시클로알킬기 또는 －R6로부터 선택된 1 내지 3개의 기로 임의로 치환된 페닐, 나프틸, 티에닐, 푸릴, 피리딜, 벤조티에닐, 벤조푸릴, 퀴놀린, 이소퀴놀릴 또는 메틸렌디옥시페닐을 함유하는 아릴기 또는 －아릴 및 알킬은 상기 정의된 바와 같은 아릴알킬, 아릴옥시알킬, 아릴티오알킬 또는 아릴술포닐알킬기 또는 －R1및 R2는 고리에 결합된 탄소와 함께 5 내지 7개의 원자를 갖는 탄소고리 또는 헤테로고리를 형성할 수 있고, 이들 고리는 R6에서 선택된 1 내지 3개의 기로 임의로 치환된 페닐에 융합되는것도 가능하다 :
    －R3는 : －p가 0이거나 (M)P가 CH2기인 경우, 임의로 할로겐화된 C1내지 C2알킬기 또는 수소, －(M)P가 산소 또는 황 원자인 경우, 임의로 할로겐화된 C1내지 C2알킬기를 나타내고 ; －R4는 : －수소 원자 또는 －탄소수 1 내지 6을 함유하는 알킬기 또는 －탄소수 2 내지 6을 함유하는 알콕시알킬, 알킬티오알킬, 할로알킬, 시아노알킬, 티오시아노알킬, 알케닐 또는 알키닐기 또는 －탄소수 3 내지 6을 함유하는 디알킬아미노알킬, 알콕시카르보닐알킬 또는 N－알킬카르바모일알킬기 또는 －탄소수 4 내지 8을 함유하는 N,N－디알킬카르바모일알킬기 또는 －R6로부터 선택된 1 내지 3개의 기로 임의로 치환된 페닐, 나프틸, 티에닐, 푸릴, 피리딜, 피리미딜, 피리다지닐, 피라지닐, 벤조티에닐, 벤조푸릴, 퀴놀린, 이소퀴놀릴 또는 메틸렌디옥시페닐을 함유하는 아릴기 또는. －상기 정의된 아릴 및 알킬을 갖는, 아릴알킬, 아릴옥시알킬, 아릴티오알킬 또는 아릴술포닐알킬기를 나타내며 ; －R5는 ; －H, 단 R4가 H인 경우는 제외, 또는 －탄소수 1 내지 6을 함유하는 알킬, 할로알킬, 알킬술포닐 또는 할로알킬술포닐기 또는 －탄소수 2 내지 6을 함유하는 알콕시알킬, 알킬티오알킬, 아실, 알케닐, 알키닐, 할로아실, 알콕시카르보닐, 할로알콕시카르보닐, 알콕시알킬술포닐 또는 시아노알킬술포닐기 또는 －탄소수 3 내지 6을 함유하는 알콕시알콕시카르보닐, 알킬티오알콕시카르보닐 또는 시아노알콕시카르보닐기 또는 －포르밀기 또는 －탄소수 3 내지 6을 함유하는 시클로알킬, 알콕시아실, 알킬티오아실, 시아노아실, 알케닐카르보닐 또는 알키닐카르보닐기 또는 －탄소수 4 내지 8을 함유하는 시클로알킬카르보닐기 또는 －페닐 ; 아릴알킬카르보닐, 특히 페닐아세틸 및 페닐프로피오닐 ; R6로부터 선택된 1 내지 3개의 기로 임의로 치환된 아릴카르보닐, 특히 벤조일 ; 티에닐카르보닐 ; 푸릴카르보닐 ; 피리딜카르보닐 ; 벤질옥시카르보닐 ; 푸르푸릴옥시카르보닐 ; 테트라히드로푸르푸릴옥시카르보닐 ; 티에닐메톡시카르보닐 ; 피리딜메톡시카르보닐 ; 펜옥시카르보닐 또는 (페닐티오)카르보닐, 그자체가 R6로부터 선택된 1 내지 3개의 기로 임의로 치환된 페닐 ; (알킬티오)카르보닐 ; (할로알킬티오)카르보닐 ; (알콕시알킬티오)카르보닐 ; (시아노알킬티오)카르보닐 ; (벤질티오)카르보닐; (푸르푸릴티오)카르보닐 ; (테트라히드로푸루푸릴티오)카르보닐 ; (티에닐메틸티오)카르보닐 ; (피리딜메틸티오)카르보닐 또는 아릴술포닐기 또는 －하기 기에 의해 임의로 일치환 또는 이치환된 카르바모일기 ; －탄소수 1 내지 6을 함유하는 알킬 또는 할로알킬기 －탄소수 3 내지 6을 함유하는 시클로알킬, 알케닐 또는 알키닐기 또는 －탄소수 12 내지 6을 함유하는 알콕시알킬, 알킬티오알킬 또는 시아노알킬기 또는 －1 내지 3개의 R6기로 임의로 치환된 페닐 ; －탄소수 3 내지 8을 함유하는 알킬티오알킬술포닐기 또는 탄소수 3 내지 7을 함유하는 시클로알킬술포닐기를 나타내고 ; －R4및 R5는 부착된 질소 원자와 함께 탄소수 1 내지 3개를 함유하는 알킬로 임의로 치환된 피롤리디노, 피페리디노, 모르폴리노 또는 피페라지노기를 형성할 수 있으며 ; －R6는 : －할로겐 원자 또는 －탄소수 1 내지 6을 함유하는 알킬, 할로알킬, 알콕시, 할로알콕시, 알킬티오, 할로알킬티오, 또는 알킬술포닐기 또는 －탄소수 3 내지 6을 함유하는 시클로알킬, 할로시클로알킬, 알케닐옥시, 알키닐옥시, 알케닐티오 또는 알키닐티오기 또는 －니트로 또는 시아노기 또는 －탄소수 1 내지 6을 함유하는 알킬 또는 아실기에 의하여 임의로 일치환 또는 이 치환된 아미노기 또는 탄소수 2 내지 6을 함유하는 알콕시카르보닐기, －R7에서 선택된 동일 하거나 상이한 1 내지 3개의 기로 임의로 치환된 페닐, 펜옥시 또는 피리딜옥시기를 나타내고 ; －R7은 ; －불소, 염소, 브롬, 또는 요오드로부터 선택된 할로겐 원자, 또는 －탄소수 1 내지 6을 함유하는 직쇄 또는 측쇄 알킬기, 또는 탄소수 1 내지 6을 함유하는 직쇄 또는 측쇄 알콕시 또는 알킬티오기, 또는 －탄소수 1 내지 6을 함유하는 직쇄 또는 측쇄 할로알콕시 또는 할오알킬티오기, 또는 －니트릴기, 또는 －니트로기를 나타낸다.]
  2. 제 1 항에 있어서, 하기식 Ⅱ의 광학 활성화합물 :
  3. 제 2 항에 있어서, W가 산소원자를 나타내는 식 Ⅱ의 광학활성 화합물.
  4. 제 3 항에 있어서, W는 산소원자이고, R2는 메틸이며, M은 황 원자이고, p는 1이며, R3는 메틸이고, R4는 페닐이고, R5및 R6는 수소원자를 나타내는 식 Ⅱ의 S－(－)거울상 이성질체 화합물인 것을 특징으로 하는 화합물.
  5. 하기식 Ⅲ의 화합물과 식 R3Ⅹ (식중, Ⅹ는 염소, 브롬 또는 요오드 원자 또는 슬페이트기 또는 알킬술포닐옥시, 또는 아릴술포닐옥시기를 나타낸다.)의 화합물을 －5℃ 내지 －80℃의 온도에서 용매 및 염기의 존재하에 반응시키는 것을 특징으로 하는 제 1 항 내지 제 4 항 중의 어느 한항에 따른 p＝1이고 M＝S이며 W＝O인 식 Ⅰ의 화합물의 제조방법
  6. 제 5 항에 있어서, 용매가 에테르, 고리형 에테르, 알킬 에스테르, 아세토니트릴, 탄소수 1 내지 3을 함유하는 알콜 또는 방향족 용매, 바람직하게는 테트라히드로푸란에서 선택되는 것을 특징으로 하는 제조방법.
  7. 제 5 항에 있어서, 염기가 알콕시드, 바람직하게는 포타슘 t－부톡시드, 알칼리 금속 또는 알칼리 토금속 히드록시드, 알칼리 금속 카르보네이트 또는 삼차 아민에서 선택되는 것을 특징으로 하는 제조방법.
  8. p＝1이고 M＝S인 식 Ⅰ의 대응하는 화합물과 식 R3OH의 알콜을 50 내지 80℃의 온도에서 용매 및 강염기의 존재하에 반응시키는 것을 특징으로 하는 제 1 항 내지 제 4 항 중의 어느 한항에 따른 p＝1이고 M＝O이고 W＝O인 식 Ⅰ의 화합물의 제조방법.
  9. 제 8 항에 있어서, 강염기가 알칼리 금속 히드록시드, 강 유기 염기 또는 식 R3O Met+(식중, Met+는 알칼기 금속 또는 알칼기 토금속을 나타낸다.)의 알킬 금속 알콕시드에서 선택되는 것을 특징으로 하는 제조방법.
  10. 제 8 항에 있어서, 반응이 용매로서는 알콜 R3OH를, 염기로서는 소듐 알콜시드 R3O Met+를 취하여 수행하는 것을 특징으로 하는 제조방법.
  11. 하기식 Ⅶ의 화합물과 과량의 디메틸포름아미드 디메틸아세탈을 10 내지 100℃의 온도에서 반응시키는 것을 특징으로 하는 제 1 항 내지 제 4항 중의 어느 한 항에 따른 p＝0이고 R3가 수소원자인 식 Ⅰ의 화합물의 제조방법.
  12. 하기식 Ⅸ의 화합물과 하기식 Ⅴ의 화합물을 반응시키는 것을 특징으로 하는 제 1 항 내지 제 3 항 중의 어느 한항에 따른 R3가 임의로 할로겐화된 C1∼C2알킬기이고 p＝0 또는 p＝1이고 M＝CH2인 식 Ⅰ의 광학 활성 화합물의 제조방법.
  13. 하기식을 갖는 것을 특징으로 하는, 제 1 항 내지 제 4 항 중의 어느 한항에 따른 식 Ⅰ의 화합물의 제조시 특히 중간체로서 유용한 광학 활상 화합물 :
    [식중 R1내지 R5는 본 발명의 일반식 Ⅰ에서와 동일한 의미를 갖는다.] 및 하기식 Ⅸ의 화합물 :
    [식중, R3는 임의로 할로겐화된 C1내지 C3알킬기를 나타낸다.] 및 하기식 Ⅶb의 화합물 :
    [식중, R2는 상기와 동일한 의미를 가지며, R6는 상기 정의된 R7으로부터 선택된 동일하거나 상이한 1 내지 3개의 기로 치환될 수 있는 페닐, 펜옥시 또는 피리딜옥시기를 나타낸다.]
  14. 제13항에 있어서, 식 Ⅲ,Ⅳ,Ⅵ,Ⅶ,Ⅷ 및 Ⅸ의 R1이 페닐이고 R2는 메틸인 것을 특징으로 하는 화합물.
  15. 하나이상의 농경학적으로 허용가능한 고체 또는 액체 부형제 및/또는 농경학적으로 또한 허용가능한 계면 활성제, 제 1 항 내지 제 4 항중의 어느 한항에 따른 식 Ⅰ의 화합물로부터 선택된 하나(또는 수개의) 활성물질과 혼합되는 것을 특징으로 하는 살진균성 조성물.
  16. 제 1 항 내지 제 4 항 중의 어느 한항에 따른 식 Ⅰ의 광학활성 화합물의 유효량을 예방적으로 또는 치료적으로 적용하는 것을 특징으로 하는 진균성 병해에 감염되거나 될 수 있는 감염된 농작물의 처리방법.
  17. 제16항에 있어서, 식 Ⅰ의 화합물을 0.005 내지 5㎏/㏊, 바람직하게는 0.01 내지 1㎏/㏊의 양으로 적용하는 것을 특징으로 하는 농작물의 처리방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019940013823A 1993-06-18 1994-06-18 살진균성 광학 활성 2-이미다졸린-5-온 및 2-이미다졸린-5-티온 유도체 KR100348201B1 (ko)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR93-7663 1993-06-18
FR9307663A FR2706455B1 (fr) 1993-06-18 1993-06-18 Dérivés optiquement actifs de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides.
FR9402144A FR2706456B1 (fr) 1993-06-18 1994-02-21 Dérivés optiquement actifs de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides.
FR94-2144 1994-02-21

Publications (2)

Publication Number Publication Date
KR950000670A true KR950000670A (ko) 1995-01-03
KR100348201B1 KR100348201B1 (ko) 2002-11-18

Family

ID=26230430

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019940013823A KR100348201B1 (ko) 1993-06-18 1994-06-18 살진균성 광학 활성 2-이미다졸린-5-온 및 2-이미다졸린-5-티온 유도체

Country Status (36)

Country Link
US (3) US6018052A (ko)
EP (1) EP0629616B1 (ko)
JP (1) JP3844793B2 (ko)
KR (1) KR100348201B1 (ko)
CN (4) CN1055465C (ko)
AP (1) AP461A (ko)
AT (1) ATE204865T1 (ko)
AU (1) AU690107B2 (ko)
BG (1) BG62329B1 (ko)
BR (1) BR9401828A (ko)
CA (1) CA2125236C (ko)
CO (1) CO4180381A1 (ko)
CZ (1) CZ287317B6 (ko)
DE (1) DE69428080T2 (ko)
DK (1) DK0629616T3 (ko)
EG (1) EG20455A (ko)
ES (1) ES2160114T3 (ko)
FI (1) FI119842B (ko)
FR (1) FR2706456B1 (ko)
HK (3) HK1029341A1 (ko)
HR (1) HRP940351B1 (ko)
HU (2) HU9802837D0 (ko)
IL (3) IL122339A (ko)
MA (1) MA23226A1 (ko)
MY (1) MY115311A (ko)
NZ (1) NZ260768A (ko)
PE (1) PE57094A1 (ko)
PL (1) PL177934B1 (ko)
PT (1) PT629616E (ko)
RO (1) RO113858B1 (ko)
RU (1) RU2126390C1 (ko)
SI (1) SI0629616T1 (ko)
SK (1) SK283708B6 (ko)
TR (1) TR28762A (ko)
TW (1) TW304192B (ko)
UA (1) UA44219C2 (ko)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2685328B1 (fr) * 1991-12-20 1995-12-01 Rhone Poulenc Agrochimie Derives de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides.
FR2698359B1 (fr) * 1992-11-25 1995-10-27 Rhone Poulenc Agrochimie Derives de 2-alkoxy 2-imidazoline-5-ones fongicides.
FR2722499B1 (fr) * 1994-07-13 1996-08-23 Rhone Poulenc Agrochimie Nouveaux derives de 2-imidazoline-5-ones fongicides
FR2722652B1 (fr) * 1994-07-22 1997-12-19 Rhone Poulenc Agrochimie Composition fongicide comprenant une 2-imidazoline-5-one
FR2778671B1 (fr) * 1998-05-14 2002-07-05 Rhone Poulenc Agrochimie Nouveau procede de preparation d'intermediaires de synthese
FR2783401B1 (fr) * 1998-09-21 2000-10-20 Rhone Poulenc Agrochimie Nouvelles compositions fongicides
FR2788271B1 (fr) 1999-01-07 2001-02-09 Rhone Poulenc Agrochimie Nouveau procede de preparation d'aminoacides chiraux
DE19917617A1 (de) * 1999-04-19 2000-10-26 Bayer Ag -(-)Enantiomeres des 2-[2-(1-Chlor-cyclopropyl)-3-(2-chlorphenyl) 2-hydroxy-propyl]-2,4-dihydro-[1,2,4]-triazol-3-thions
FR2794743A1 (fr) * 1999-06-09 2000-12-15 Aventis Cropscience Sa Nouveau procede de preparation d'alpha-aminonitriles optiquement actifs
AU6427800A (en) * 1999-06-14 2001-01-02 Novartis Ag Fungicidal combinations
FR2800734B1 (fr) * 1999-11-05 2002-08-23 Aventis Cropscience Sa Cristal d'acide amine chiral et son procede de preparation
DE10019758A1 (de) 2000-04-20 2001-10-25 Bayer Ag Fungizide Wirkstoffkombinationen
DE10103832A1 (de) * 2000-05-11 2001-11-15 Bayer Ag Fungizide Wirkstoffkombinationen
DE10049804A1 (de) * 2000-10-09 2002-04-18 Bayer Ag Wirkstoffkombinationen mit fungiziden und akariziden Eigenschaften
US6759551B1 (en) 2000-11-03 2004-07-06 Bayer Cropscience S.A. Chiral (s- or r-methylphenylglycine) amino acid crystal and method for preparing same
FR2821718B1 (fr) * 2001-03-08 2003-06-13 Aventis Cropscience Sa Nouvelles compositions fongicides a base de derives de pyridylmethylbenzamide et d'imidazoline ou d'oxazolidine
US7794965B2 (en) 2002-03-13 2010-09-14 Signum Biosciences, Inc. Method of identifying modulators of PP2A methylase
MXPA04010344A (es) 2002-04-24 2005-03-07 Basf Ag Uso de alcoxilatos de alcohol especifico como un adyuvante para aplicaciones agrotecnicos.
DE10347090A1 (de) 2003-10-10 2005-05-04 Bayer Cropscience Ag Synergistische fungizide Wirkstoffkombinationen
DE10349501A1 (de) 2003-10-23 2005-05-25 Bayer Cropscience Ag Synergistische fungizide Wirkstoffkombinationen
US20050203156A1 (en) * 2004-03-12 2005-09-15 Wyeth Hydantoins having RNase modulatory activity
DE102004049761A1 (de) 2004-10-12 2006-04-13 Bayer Cropscience Ag Fungizide Wirkstoffkombinationen
WO2006084033A1 (en) 2005-02-03 2006-08-10 Signum Biosciences, Inc. Compositions and methods for enhancing cognitive function
US7923041B2 (en) 2005-02-03 2011-04-12 Signum Biosciences, Inc. Compositions and methods for enhancing cognitive function
DE102005026482A1 (de) 2005-06-09 2006-12-14 Bayer Cropscience Ag Wirkstoffkombinationen
EP1893024B1 (de) 2005-06-09 2010-10-13 Bayer CropScience AG Wirkstoffkombinationen
ITMI20051558A1 (it) 2005-08-09 2007-02-10 Isagro Spa Miscele e-o composizioni sinergiche cin elevata attivita'fungicida
CL2007003743A1 (es) 2006-12-22 2008-07-11 Bayer Cropscience Ag Composicion que comprende fenamidona y un compuesto insecticida; y metodo para controlar de forma curativa o preventiva hongos fitopatogenos de cultivos e insectos.
DE102007045920B4 (de) 2007-09-26 2018-07-05 Bayer Intellectual Property Gmbh Synergistische Wirkstoffkombinationen
CN102014897B (zh) 2008-04-21 2015-08-05 西格纳姆生物科学公司 化合物、组合物和其制备方法
BR112012001080A2 (pt) 2009-07-16 2015-09-01 Bayer Cropscience Ag Combinações de substâncias ativas sinérgicas contendo feniltriazóis
MX2012006615A (es) * 2009-12-11 2012-10-05 Autifony Therapeuticts Ltd Derivados de imidazolidinodiona.
BR112012029225B1 (pt) * 2010-05-19 2020-10-27 Sandoz Ag processo para a preparação de um composto quiral, composto quiral e uso de um composto quiral
CN103081915A (zh) * 2011-11-07 2013-05-08 深圳诺普信农化股份有限公司 一种杀菌组合物
EP2622961A1 (en) 2012-02-02 2013-08-07 Bayer CropScience AG Acive compound combinations
CN102919250A (zh) * 2012-11-14 2013-02-13 陕西农心作物科技有限公司 一种含苯噻菌胺的杀菌组合物
WO2015037243A1 (ja) * 2013-09-12 2015-03-19 興和株式会社 光学活性ヒダントイン化合物の製造方法

Family Cites Families (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB967167A (en) * 1960-10-31 1964-08-19 Ici Ltd N-trichloromethylmercaptohydantoins and fungicidal compositions containing them
NL257812A (ko) * 1959-11-10
BE623153A (ko) * 1961-10-04
DE1176660B (de) * 1963-07-05 1964-08-27 Beiersdorf & Co A G P Verfahren zur Herstellung von triaryl-substituierten Imidazolinonen-4(5)
GB1026509A (en) * 1963-08-13 1966-04-20 Novalis Lab New derivatives of n-substituted ª‡-amino acids and processes for their production
DE1258412B (de) * 1964-08-29 1968-01-11 Beiersdorf Ag Verfahren zur Herstellung von 5, 5-Bis-(p-hydroxyphenyl)-imidazolinonen-(4) und ihren Salzen
GB1167192A (en) * 1967-12-19 1969-10-15 Boots Pure Drug Co Ltd Improvements in the Preparation of Propionic Acids
FR2329276A1 (fr) * 1975-10-29 1977-05-27 Roussel Uclaf Nouvelles imidazolidines substituees, procede de preparation, application comme medicament et compositions les renfermant
US4280008A (en) * 1976-12-24 1981-07-21 Basf Aktiengesellschaft Chirally substituted 2-imidazolin-5-ones
DE2658941A1 (de) * 1976-12-24 1978-07-06 Basf Ag Verfahren zur herstellung von optisch aktiven alpha-methyl-aryl- alaninen
US4428948A (en) * 1977-02-03 1984-01-31 Rohm And Haas Company Novel heterocyclic compounds
IL57504A0 (en) * 1978-06-15 1979-10-31 Beecham Group Ltd Prostagandin analogues,their preparation and pharmaceutical compositions containing
US4459411A (en) * 1982-09-13 1984-07-10 The Dow Chemical Company Preparation of unsaturated heterocyclic carbonyl-containing compounds
DE3305203A1 (de) * 1983-02-16 1984-08-16 Bayer Ag, 5090 Leverkusen N-sulfenylierte hydantoine, ein verfahren zu ihrer herstellung und ihre verwendung als mikrobizide
DE3340595A1 (de) * 1983-11-10 1985-05-23 Hoechst Ag, 6230 Frankfurt Imidazolinone, verfahren zu ihrer herstellung und ihre verwendung im pflanzenschutz
US4692532A (en) * 1984-11-23 1987-09-08 Ciba-Geigy Corporation Substituted N-(4-hydroxyphenylthioalkyl) cyclic imides
US4657922A (en) * 1985-05-24 1987-04-14 Mcneilab, Inc. Anxiolytic 4,5-dihydro-4-oxo-1H-imidazol-2-yl urea derivatives
EP0349580B1 (en) * 1987-03-20 1991-05-15 E.I. Du Pont De Nemours And Company Fungicidal aminotriazoles and aminoimidazoles
EP0303863A3 (en) * 1987-08-17 1991-10-23 American Cyanamid Company Benzenesulfonyl carboxamide compounds, intermediate compounds and methods of preparation thereof and use of said compounds and intermediate compounds as herbicidal agents
JPH0219363A (ja) * 1988-07-06 1990-01-23 Fujisawa Pharmaceut Co Ltd イミダゾリジン誘導体
US4931582A (en) * 1988-11-04 1990-06-05 Minnesota Mining And Manufacturing Company Fluorinated, acrylamide-functional monomers
US4957933A (en) * 1989-04-21 1990-09-18 E. I. Du Pont De Nemours And Company Fungicidal oxazolidinones
US5213607A (en) * 1989-12-20 1993-05-25 American Cyanamid Company 2-(1-substituted-2-imidazolin-2-yl) benzoic and nicotinic acids and method for their preparation
FR2671348B1 (fr) * 1991-01-09 1993-03-26 Roussel Uclaf Nouvelles phenylimidazolidines, leur procede de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant.
RU2059603C1 (ru) * 1991-05-09 1996-05-10 Хоффманн-Ля Рош АГ ПРОИЗВОДНЫЕ α -ЗАМЕЩЕННЫХ АРИЛУКСУСНЫХ КИСЛОТ И ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ
US5177097A (en) * 1991-07-24 1993-01-05 E. R. Squibb & Sons, Inc. Acyl amidine and acyl, guanidine substituted biphenyl derivatives
FR2685328B1 (fr) * 1991-12-20 1995-12-01 Rhone Poulenc Agrochimie Derives de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides.
US6002016A (en) * 1991-12-20 1999-12-14 Rhone-Poulenc Agrochimie Fungicidal 2-imidazolin-5-ones and 2-imidazoline-5-thiones
FR2698359B1 (fr) * 1992-11-25 1995-10-27 Rhone Poulenc Agrochimie Derives de 2-alkoxy 2-imidazoline-5-ones fongicides.
FR2693192B1 (fr) * 1992-07-02 1994-08-12 Rhone Poulenc Agrochimie Dérivés de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides.
ES2149815T3 (es) * 1992-05-22 2000-11-16 Du Pont Imidazolinonas fungicidas.
US6013052A (en) * 1997-09-04 2000-01-11 Ep Technologies, Inc. Catheter and piston-type actuation device for use with same

Also Published As

Publication number Publication date
PT629616E (pt) 2002-02-28
BG62329B1 (bg) 1999-08-31
FR2706456A1 (fr) 1994-12-23
CZ287317B6 (en) 2000-10-11
SI0629616T1 (en) 2001-12-31
US5650519A (en) 1997-07-22
CN1106803A (zh) 1995-08-16
HK1066010A1 (en) 2005-03-11
RU94021649A (ru) 1996-04-20
BG98855A (bg) 1995-05-31
ATE204865T1 (de) 2001-09-15
HUT67152A (en) 1995-02-28
HU9401829D0 (en) 1994-09-28
PE57094A1 (es) 1995-02-07
EP0629616A3 (fr) 1995-05-24
CN1129583C (zh) 2003-12-03
US6344564B1 (en) 2002-02-05
CA2125236C (en) 2007-11-20
PL177934B1 (pl) 2000-01-31
PL303864A1 (en) 1995-01-09
HRP940351A2 (en) 1996-12-31
UA44219C2 (uk) 2002-02-15
TR28762A (tr) 1997-02-20
DE69428080D1 (de) 2001-10-04
AU6458694A (en) 1994-12-22
EP0629616A2 (fr) 1994-12-21
EG20455A (fr) 1999-04-29
KR100348201B1 (ko) 2002-11-18
IL110023A (en) 1999-12-31
RO113858B1 (ro) 1998-11-30
IL110023A0 (en) 1994-10-07
CA2125236A1 (en) 1994-12-19
HRP940351B1 (en) 2002-04-30
ES2160114T3 (es) 2001-11-01
JP3844793B2 (ja) 2006-11-15
CZ149194A3 (en) 1995-01-18
IL122339A0 (en) 1998-04-05
CN1265394A (zh) 2000-09-06
DK0629616T3 (da) 2001-10-08
HU221038B1 (hu) 2002-07-29
IL122339A (en) 1999-12-31
AU690107B2 (en) 1998-04-23
MY115311A (en) 2003-05-31
NZ260768A (en) 1996-02-27
CN1511832A (zh) 2004-07-14
CN1230425C (zh) 2005-12-07
FI942911A (fi) 1994-12-19
FI119842B (fi) 2009-04-15
CO4180381A1 (es) 1995-06-07
MA23226A1 (fr) 1994-12-31
CN1480451A (zh) 2004-03-10
CN1055465C (zh) 2000-08-16
AP9400648A0 (en) 1994-07-31
FI942911A0 (fi) 1994-06-17
EP0629616B1 (fr) 2001-08-29
HU9802837D0 (en) 1999-02-01
SK73994A3 (en) 1995-03-08
DE69428080T2 (de) 2002-04-11
JPH07330737A (ja) 1995-12-19
US6018052A (en) 2000-01-25
FR2706456B1 (fr) 1996-06-28
HK1029341A1 (en) 2001-03-30
SK283708B6 (sk) 2003-12-02
RU2126390C1 (ru) 1999-02-20
BR9401828A (pt) 1995-01-17
CN1229336C (zh) 2005-11-30
TW304192B (ko) 1997-05-01
HK1062908A1 (en) 2004-12-03
AP461A (en) 1996-02-17

Similar Documents

Publication Publication Date Title
KR950000670A (ko) 살진균성 광학 활성 2-이미다졸린-5-온 및 2-이미다졸린-5-티온 유도체
EP0551048B1 (fr) Dérivés de 2-imidazoline-5-one et 2-imidazoline-5-thiones fongicides
US5637729A (en) Fungicidal 2-imidazolin-5-ones and 2-imidazoline-5-thiones
KR920000705A (ko) 히드라진카복스아미드 유도체, 이의 제조방법 및 이의 용도
KR20020084088A (ko) 히드록시피콜린산 유도체의 제조 방법
RO111765B1 (ro) Derivati de 4-oxazolidinona, procedeu pentru prepararea acestora, compozitii agricole care ii contin si metoda pentru combaterea bolilor fungice la plante
EP0304954A2 (en) Cyclic dipeptide enantiomers
AU2005264473A1 (en) Diamine derivative, process of preparation thereof, and fungicide comprising diamine derivative as an active ingredient
FR2693192A1 (fr) Dérivés de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides.
KR940011450A (ko) 살진균성 2-알콕시-2-이미다졸린-5-온 유도체
KR100648029B1 (ko) 키랄 아미노산의 신규한 제조 방법
FR2716192A1 (fr) Dérivés de 2-imidazoline-5-ones fongicides.
KR880008999A (ko) 3-아릴-5-알킬티오-4h-1,2,4-트리아졸
US6008370A (en) Fungicidal-2-alkoxy/haloalkoxy-1-(mono- or disubstituted)amino-4,4-disubstituted-2-imidazolin-5-ones
WO1995034541A1 (fr) Derives de 5-imino-2-imidazolines fongicides
PT101000A (pt) Derivados de benzotiofeno uteis como pesticidas e processo para a sua preparacao
FR2706455A1 (fr) Dérivés optiquement actifs de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides.
CA2187174A1 (en) .alpha.-substituted phenylacetic acid derivative, process for producing the same, and agricultural bactericide containing the same

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: 20120629

Year of fee payment: 11

FPAY Annual fee payment

Payment date: 20130705

Year of fee payment: 12

EXPY Expiration of term