KR910007905A - 카르복시아미드, 이들의 제조방법 및 제초제로서의 이들의 사용방법 - Google Patents
카르복시아미드, 이들의 제조방법 및 제초제로서의 이들의 사용방법 Download PDFInfo
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Abstract
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Claims (9)
- 하기 일반식(Ia), (Ib) 및 (Ic)의 카르복시이미드 및 이들의 농업적으로 적합한 염:상기식에서 X는 산소 또는 황원자이고: R1은 수소원자: 할로겐원자, C1-C4-알킬, C1-C4-할로알킬, C1-C4-알콕시 및/또는 C1-C4-할로알콕시기들중 1내지 3개의 기들에 의해 치환될 수 있는 C3-C8-시클로알킬기: 히드록실시, 할로겐원자, C3-C4-시클로알킬, C1-C4-알콕시, C1-C4-할로알콕시, C1-C4-알킬티오, C1-C4-할로알킬티오, C1-C4-알킬아미노, 디-C1-C4-알킬아미노 및/또는 C3-C6-시클로알킬아미노기들 중 1내지 3개의 기들에 의해 치환될 수 있는 C1-C4-알킬기 및기이며, 여기에서 R은 시아노: 니트로기: 할로겐원자: C1-C4-할오알킬: C1-C4-알콕시C1-C2-할로알콕시:C2-C4-알킬일옥시:C1-C4-알킬티오:C1-C4-할로알킬티오: C3-C6-알콕시카르보닐알콕시 및/또는 C1-C4-알콕시카르보닐기이고, m은 0,1,2 또는 3이고, m이 2 또는 3일 경우 R은 서로 다를수 있고: R은 히드록시:C1-C4-알콕시:C2-C6-시아노알킬: R에 기재된 기들중 1내지 3개의 기들에 의해 치환될 수 있는 C3-C6-알켄일, C3-C6-알킨일, 페닐 또는 나프틸기:할로겐원자, C1-C4-알킬, C1-C4-할로알킬, C1-C4-알콕시, C1-C4-할로알콕시 및/또는 C1-C4-알킬티오들중 1 또는 2개의 기들에 의해 치환될 수 있는 질소, 산소 및 황원자로 이루어진 그룹으로부터 선택된 1또는 2개의 헤테로원자를 갖는 5- 또는 6- 원자 헤테로고리기: R1에 기재된 기들중 하나의 기이거나, 또는 R1및 R2는 고리구성원으로서 메틸렌기이외에도 산소, 황원자, N-메틸 또는 카르보닐기들중 하나를 포함 할수 있는 4- 내지 7-원자사슬을 함께 형성하고; R3및 R4는 각기 니트로: 시아노기:할로겐원자:1 또는 2개의 C1-C4-알킬기 및/또는 하나의 C1-C4-알킬 카르보닐기에 의해 치환될 수 있는, 아미노기:1 내지 9개의 할로겐원자들에 의해 치환될수 있는 C1-C4-알콕시 또는 C1-C4-알킬티오기:할로겐원자, C1-C4-알킬, C1-C4-할로알킬, C1-C4-알콕시, C1-C4-할로알콕시 및/또는 C1-C4-알킬티오기들중 1 또는 2개의 기들에 의해 치환될 수 있는, 산소, 황 및 질소원자로 이루어진 그룹에서 선택된 1 또는 2개의 헤테로원자를 포함하는 5-또는 6-원자 헤테로고리기: R에 기재된 기들중 1내지 3개의 기들에 의해 치환될 수 있는, C2-C6-알켄일, C2-C6-알킨일, 페닐, 페녹시 또는 페닐-티오기:또는 R1에 기재된 기들중 하나이고: R5는 프로밀, 4,5-디히드로옥사졸-2-일기 또는 COYR6이고: Y는 산소 또는 황원자이고:R6는 수소원자:C3-C8-시클로알킬기:시아노, 아미노카르보닐, 카르복실, 트리메틸실일, C1-C4-알콕시 C1-C4-알콕시, C1-C4-알킬티오, C1-C4-알킬아미노, 디-C1-C4-알킬아미노, C1-C4-알킬술피닐, C1-C4-알킬술포닐, C1-C4-알콕시카르보닐, C2-C4-알콕시카르보닐 -C1-C3-알콕시, C2-C4-알콕시카르보닐-C1-C5-알콕시카르보닐, C1-C4-알킬아미노카르보닐, 디-C1-C4-알킬아미노카르보닐, 디-C1-C4-알킬포스폰일, C1-C4-알킬아미녹시, 페닐, 티에닐, 벤질옥시, 벤질티오, 푸릴, 테트라히드로푸릴, 프탈아미도, 피리딜 및/또는 벤조일 기들중 하나의 기 및/또는 1내지 5개의 할로겐원자 또는 히드록실기에 의해 치환될수 있는 C1-C6-알킬기(이중에서 고리기들은 R에 기재된 기들중 1내지 3개의 기들에 의해 치환될 수 있는 하드록시기, 할로겐 원자, C1-C4-알콕시 또는 페닐기들중 하나의 기에 치환될 수 있는) C3-C6-알켄일, C3-C6-알킨일 또는 C5-C7-시클로알켄일기(이중에서 페닐기는 R에 기재된 기들중 1내지 3개의 기들에 의해 치환될 수있음):질소, 산소 및 황원자로 이루어진 그룹으로부터 선택된 1 또는 2개의 헤테로원자를 포함하는 5- 또는 6- 원자헤테로 고리기:프탈이미도:테트라히드로포탈이미도: 숙신이미도:말레이미도: 벤조트리아졸일기: R에 기재된 기들중 1 내지 3개의 기들에 의해 치환될수 있는 페닐기:-N=CR7R8이고, 여기에서 R7은 수소원자 또는 C1-C6-알킬기이고 R8은 C3-C6-시클로알킬, 페닐, 푸릴기 또는 하나의 R7이거나, 만일, R5가 카르복실, 메톡시카르보닐 또는 에톡시카르보닐기이고, R2가 수소원자이고 R3가 수소원자가아니고 R4가 수소원자 또는 메틸기가 아닐경우, 및 만일, R5가 카르복실, 메톡시카르보닐 또는 에톡시카르보닐기이고, R4가 수소원자이고, R3가 수소원자아니고 R2가 수소원자:C1-C4-알킬:페닐:2(3,4-디메톡시페닐_에틸 또는 2,5-디클로로티엔-3-일기들중 하나가 아닐경우에는, R7및 R8는 함께 4- 내지 7-원자 알킬렌사슬을 형성한다.
- 하기일반식(Ⅱ)의 대응하는 디카르복실산 무수물을 통상적인 방법에 따라 하기일반식(Ⅲ)의 아민과 반응시키는 것을 특징으로 하는, R5가 카르복실기인 제1항에 기재된 화합물(Ia)의 제조방법.HNR1R2(Ⅲ)
- 하기일반식(Ⅳa), (Ⅳb) 또는 (Ⅳc)의 대응하는 카르복실산을 통상적인 방법에 따라 카르복실산의 할로겐화물 또는 그의 활성화된 형태로 전환시킨다음, 이러한 유도체를 일반식(Ⅲ)의 아민과 반응시키고, 이어서 결과된 하기의 카르복시아미드(Ⅴa),(Vb) 또는 (Vc)를 염기의 존재하에 카르복실화제 또는 포르밀화제와 반응시킴을 특징으로 하는, R3및 R4는 브롬 또는 요오드 원자가 아니고 R5는 포르밀 또는 카르복실기인 제1항에 기재된 화합물(Ia),(Ib) 및 (Ic)의 제조방법.
- 하기일반식(Ⅵa) 또는 (Ⅵb)의 디카르복실레이트를 통상적인 방법에 따라 디아조화시키고, 이것을 무기산할로겐화물을 가지고 하기의 대응하는 유도체(Ⅶa) 또는 (Ⅶb)로 전환시킨다음, 이것을 일반식(Ⅲ)의 아민으로서 아미드화시키고, 수득한 화합물(Ib) 및 (Ic)의 이성질체 혼합물을 이것의 조성물들로 분리하는 것을 특징으로 하는 R3또는 R4가 할로겐원자이고, R5가 CO2R6이고 R6가 알킬기인 제1항에 기재된 화합물 (Ib) 및 (Ic)의 제조방법:
- R5가 CO2R1이고 R6는 알킬기인, 일반식(Ib)또는 (Ic)의 대응하는 카르복시아미드를 통상적인 방법에 따라 수성염기로서 가수분해시키는 것을 특징으로 하는, 제1항에 기재된 화합물(Ib) 및 (Ic)의 제조방법.
- R5가 카르복실기인 일반식(Ia),(Ib) 또는 (Ic)의 대응하는 디카르복실산모노아미드를 통상적인 방법에 따라 카르복실산의 활성형태로 전환시킨다음 이러한 유도체를 하기의 화합물(Ⅲ)으로서 에스테르화시킴을 특징으로 하는, R5가 COYR6인 제1항에 기재된 화합물(Ia), (Ib)의 제조방법;HYR6(Ⅷ)
- R5가 CO2H인 대응하는 카르복시아미드(Ia),(Ib) 또는 (Ic)를 통상적인 방법에 따라 하기의 2-아미노에탄올(Ⅸ)로서 고리화시킴을 특징으로 하는, R5가 4,5-디히드로옥사졸-2-일기인 제1항에 기재된 화합물(Ia),(Ib) 및 (Ic)의 제조방법.
- 통상적인 비활성첨가제 및 적어도 하나의 제1항에 기재된 일반식(Ia),(Ib) 또는 (Ic)의 카르복시아미드 및/또는 하기 일반식(IA),(IB) 또는 (IC)의 카르복시아미드를 포함하는 제초제:상기식에서, R3가 수소원자이거나, 또는 R4가 수소원자 또는 메틸기일 경우, X 및 R1은 제1항에 기재된 기들이고 R5는 카르복실, 메톡시 또는 에톡시카르보닐기이고, R3가수소원자이거나, 또는 R2가 수소원자:C1-C4-알킬: 페닐:2-(3,4-디메톡시페닐)에틸 또는 2,5-디클로로티엔-3-일기들중 하나의 기일경우에는 R5는 카르복실, 메톡시 또는 에톡시 카르보닐기이고 R4는 수소원자이다.
- 원치않는 식물 및/또는 이들의 서식지를 제초적으로 유효량의 제1항의 기재된 카르복시아미드 (Ia),(Ib) 또는 (Ic) 및/또는 제8항에 기재된 카르복시아미드 (IA),(IB) 또는 (IC)로 처리하는 것을 특징으로 하는 원치않는 식물성장 억제방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3933573A DE3933573A1 (de) | 1989-10-07 | 1989-10-07 | Carbonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
DE39335739 | 1989-10-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
KR910007905A true KR910007905A (ko) | 1991-05-30 |
Family
ID=6391051
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019900016035A KR910007905A (ko) | 1989-10-07 | 1990-10-08 | 카르복시아미드, 이들의 제조방법 및 제초제로서의 이들의 사용방법 |
Country Status (8)
Country | Link |
---|---|
US (1) | US5201934A (ko) |
EP (1) | EP0423523A3 (ko) |
JP (1) | JPH03127787A (ko) |
KR (1) | KR910007905A (ko) |
CA (1) | CA2026829A1 (ko) |
DE (1) | DE3933573A1 (ko) |
HU (1) | HUT55377A (ko) |
IL (1) | IL95913A0 (ko) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4023048A1 (de) * | 1990-07-20 | 1992-01-23 | Basf Ag | Dicarbonsaeureimide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
DE4233198A1 (de) * | 1992-10-02 | 1994-04-07 | Bayer Ag | Substituierte Thiophencarbonsäureamide |
US5486621A (en) * | 1994-12-15 | 1996-01-23 | Monsanto Company | Fungicides for the control of take-all disease of plants |
US6136984A (en) * | 1996-04-22 | 2000-10-24 | Novo Nordisk A/S | Solid phase and combinatorial synthesis of substituted thiophenes and of arrays of substituted thiophenes |
IL134788A0 (en) * | 1999-03-16 | 2001-04-30 | Mitsui Chemicals Inc | A process for preparing 2-alkyl-3-aminothiophene derivatives |
US6835745B2 (en) * | 2002-01-15 | 2004-12-28 | Wyeth | Phenyl substituted thiophenes as estrogenic agents |
WO2004056746A1 (en) | 2002-12-23 | 2004-07-08 | 4Sc Ag | Cycloalkene dicarboxylic acid compounds as anti-inflammatory, immunomodulatory and anti-proliferatory agents |
US7365094B2 (en) | 2002-12-23 | 2008-04-29 | 4Sc Ag | Compounds as anti-inflammatory, immunomodulatory and anti-proliferatory agents |
CA2509138A1 (en) * | 2002-12-23 | 2004-07-08 | 4Sc Ag | Cycloalkene dicarboxylic acid compounds as anti-inflammatory, immunomodulatory and anti-proliferatory agents |
UY30892A1 (es) | 2007-02-07 | 2008-09-02 | Smithkline Beckman Corp | Inhibidores de la actividad akt |
AR075153A1 (es) * | 2009-01-30 | 2011-03-16 | Glaxosmithkline Llc | Compuesto hidrocloruro de n-{(1s)-2-amino-1-[(3-fluorofenil)metil]etil)-5-cloro-4-(4-cloro-1-metil-1h-pirazol-5-il)-2- tiofenocarboxamida en forma cristalina, composicion farmaceitica que lo comprende, procedimiento para prepararla, su uso para preparar un medicamento util para tratar o disminuir la |
BR112012023759B1 (pt) | 2010-03-23 | 2018-10-09 | Basf Se | compostos de piridazina, método para controlar pragas invertebradas, método para proteger material de propagação de planta e material de propagação de planta |
CN103108868B (zh) | 2010-06-07 | 2015-11-25 | 诺沃梅迪科斯有限公司 | 呋喃基化合物及其用途 |
CN109400595B (zh) * | 2018-12-24 | 2020-07-17 | 深圳市第二人民医院 | 一类含噻吩环的抗癌化合物 |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE201306C (ko) * | ||||
FR1488625A (fr) * | 1966-04-04 | 1967-07-13 | Toyo Koatsu Ind Inc | Composition herbicide à base de dérivés de thiazole |
US4188203A (en) * | 1975-09-11 | 1980-02-12 | Philagro | Herbicidal and phytohormonal amidoximes |
US4124376A (en) * | 1975-12-17 | 1978-11-07 | Stauffer Chemical Company | Herbicide compositions |
DE3101889A1 (de) * | 1981-01-22 | 1982-08-26 | Hoechst Ag, 6000 Frankfurt | "neue phenoxycarbonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide" |
IT1212722B (it) * | 1983-03-23 | 1989-11-30 | Medea Res Srl | Derivato dell'acido benzoico. |
GB2154232B (en) * | 1984-02-14 | 1987-08-26 | Kodak Ltd | Process for the preparation of 2-aminothiophenes |
CH664762A5 (de) * | 1984-08-30 | 1988-03-31 | Sandoz Ag | Thiophen-azofarbstoffe. |
IT1196390B (it) * | 1984-12-28 | 1988-11-16 | Consiglio Nazionale Ricerche | Uso di derivati del tiofene nel trattamento dei tumori,composizioni farmaceutiche che li contengono e composti atti allo scopo |
GB8609452D0 (en) * | 1986-04-17 | 1986-05-21 | Ici Plc | Fungicides |
DE3813885A1 (de) * | 1988-04-20 | 1989-11-02 | Schering Ag | 1-chlorpyrimidinyl-1h-1,2,4-triazol-3-sulfonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider, fungizider und pflanzenwachstumsregulierender wirkung |
JPH0248575A (ja) * | 1988-08-09 | 1990-02-19 | Sumitomo Seika Chem Co Ltd | チオフェン2,5−ジカルボン酸の製造方法 |
GB8823041D0 (en) * | 1988-09-30 | 1988-11-09 | Lilly Sa | Organic compounds & their use as pharmaceuticals |
DE3905577A1 (de) * | 1989-02-23 | 1990-08-30 | Basf Ag | Diaminothiophene |
-
1989
- 1989-10-07 DE DE3933573A patent/DE3933573A1/de not_active Withdrawn
-
1990
- 1990-09-28 EP EP19900118654 patent/EP0423523A3/de not_active Withdrawn
- 1990-10-03 US US07/592,287 patent/US5201934A/en not_active Expired - Fee Related
- 1990-10-03 CA CA002026829A patent/CA2026829A1/en not_active Abandoned
- 1990-10-05 HU HU906362A patent/HUT55377A/hu unknown
- 1990-10-05 JP JP2266572A patent/JPH03127787A/ja active Pending
- 1990-10-07 IL IL95913A patent/IL95913A0/xx unknown
- 1990-10-08 KR KR1019900016035A patent/KR910007905A/ko not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
HUT55377A (en) | 1991-05-28 |
US5201934A (en) | 1993-04-13 |
JPH03127787A (ja) | 1991-05-30 |
CA2026829A1 (en) | 1991-04-08 |
HU906362D0 (en) | 1991-04-29 |
EP0423523A2 (de) | 1991-04-24 |
IL95913A0 (en) | 1991-07-18 |
EP0423523A3 (en) | 1992-02-19 |
DE3933573A1 (de) | 1991-04-18 |
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