KR960003574A - 4-페녹시코우마린 유도체, 이들의 제조방법 및 제초제로서 이들의 사용 - Google Patents
4-페녹시코우마린 유도체, 이들의 제조방법 및 제초제로서 이들의 사용 Download PDFInfo
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Abstract
본 발명은 곡류의 존재하에 및 특히 곡물의 존재하에 단자엽 잡초 종을 제어하는 방법에 관한 것이다. 또한 본 발명은 제초제로서 유용한 4-(2,6-이치환된 페녹시)코우마린 유도체 및 이의 제법에 관한 것이다.
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Claims (10)
- 제초적 유효량의 하기 일반식 I 의 화합물을 종자 또는 그의 다른 전파 원을 함유하는 물 또는 토양에 적용하는 것으로 구성되는 단자엽성 1년생, 다년생 및 수경성 식물 종을 제어하는 방법;상기 식에서, X 및 X'는 각각 독립적으로 할로겐, C1-C4알킬 또는 C2-C4알케닐이고; W, Y 및 Z는 각각 독립적으로 O 또는 S 이고; R은 일 내지 세개의H, 할로겐, C1-C4알킬, C3-C6시클로알킬, C1-C4할로알킬 또는 C1-C4알콕시 기의 임의의 조합이고; R1은 일 내지 네개의 H, 할로겐, OH,CN,NO2,SH 임의로 하나이상의 할로겐 또는 OR2기로 치환된 C1-C6알킬, C3-C6시클로알킬, C1-C6알킬티오, C2-C6알케닐, C2-C6할로알케닐, C2-C6알키닐, C2-C6할로알키닐, OR2, OCH2COOR3, OCH2OR4, OCOOR5, OCONHR6, OCOR7, S(O)nR8, COR9, CH(OR10)2, 임의로 일 내지 세개의 할로겐, CN, C1-C6알킬, C1-C4할로알킬, C1-C4알콕시 또는 C1-C4할로알콕시 기로 치환된 페닐, 또는 임의로 일 내지 세개의 할로겐, CN, C1-C4알킬, C1-C4할로알킬 또는 C1-C4알콕시 기로 치환된 벤질의 임의의 조합이고; R2는 H, C1-C4알킬, C1-C4할로알킬, C2-C6알케닐, C2-C6할로알케닐, C2-C6알키닐 또는 C2-C6할로알키닐이고; R3,R4,R5,R6및 R7은 각각 독립적으로 H, C1-C4알킬, C1-C4할로알킬, C3-C6시클로알킬, 임의로 일 내지 세개의 할로겐, CN, C1-C4알킬, C1-C4할로알킬, C1-C4알콕시 또는 C1-C4할로알콕시 기로 치환된 페닐, 또는 임의로 일 내지 세개의 할로겐, C1-C4알킬, C1-C4할로알킬 또는 C1-C4알콕시 기로 치환된 벤질이고; R8은 C1-C4알킬, C1-C4할로알킬 또는 임의로 일 내지 세개의 할로겐, CN, C1-C4알킬, C1-C4할로알킬, C1-C4알콕시 또는 C1-C4할로알콕시 기로 치환된 페닐이고; R9는 H, OH, C1-C4알킬, C1-C4알콕시, 임의로 일 내지 세개의 할로겐, CN, C1-C4알킬, C1-C4할로알킬, C1-C4알콕시 또는 C1-C4할로알콕시 기로 치환된 페닐, 또는 임의로 일 내지 세개의 할로겐, C1-C4알킬, C1-C4할로알킬, C1-C4알콕시 또는 C1-C4할로알콕시 기로 치환된 벤질, 또는 NR11R12이고; R10은 H, C1-C4알킬 또는 -(CH2)m-이고; R11및 R12는 각각 독립적으로 H, C1-C4알킬, C2-C4알케닐이거나 또는 R11및 R12는 그들의 부착된 원자와함께 임의로 산소 원자가 중간에 있는 5- 또는 6- 원 고리를 형성하고; n은 0.1 또는 2이며, m은 2 또는 3이다.
- 제1항에 있어서, 일반식 I의 화합물이 4-(2,6-디클로로페녹시)-6-메톡시코우마린; 4-(2,6-디브로모페녹시)-8-메톡시코우마린; 4-(2,6-디클로로페녹시)-8-메톡시코우마린; 4-(2,6-디클로로페녹시)-6,7-디메톡시코우마린; 4-(2,6-디클로로페녹시)-6,7-디메톡시코우마린; 4-(2,6-디클로로페녹시)-5,6,7-트리메톡시코우마린; 4-(2,6-디브로모페녹시)-5,6,7-트리메톡시코우마린; 4-(2,6-디클로로페녹시)-5-(트리플루오로메틸)코우마린; 4-(2,6-디브로모페녹시)-5-(트리플루오로메틸)코우마린; 4-[(2-클로로-6-메틸)페녹시]-5-클로로코우마린; 4-[(2-클로로-6-메틸)페녹시]-5-클로로코우마린; 4-(2,6-디브로모페녹시)-5-클로로코우마린; 4-(2,6-디클로로페녹시)-5-클로로코우마린; 4-(2,6-디클로로페녹시)-5-클로로코우마린; 4-[(2-클로로-6-메틸)페녹시]-5-플루오로코우마린; 4-(2,6-디클로로페녹시)-5-메틸코우마린; 4-[(2-클로로-6-메틸)페녹시]-5-메틸코우마린; 또는 4-(2,6-디클로로페녹시)-5-니트로코우마린인 방법.
- 제초적 유효량의 일반식 I의 화합물을 잡초 종의 종자 또는 전파 원이 위치된 그리고 곡물이 재배되거나 이식된 물 또는 토양에 적용하는 것으로 구성된 곡물의 존재하에 단자엽 잡초 종을 선택적으로 제어하는 방법;상기 식에서, X,X',W,Y,Z,R 및 R1은 제1항에서 정의된 바와같다.
- 제3항에 있어서, 곡물이 밀, 귀리, 보리, 호밀, 쌀 또는 옥수수인 방법.
- 제4항에 있어서, 일반식 I의 화합물이 약 4.0㎏/ha 내지 0.06㎏/ha의 비율로 적용되는 방법.
- 제5항에 있어서, 일반식 I의 화합물이 4-(2,6-디클로로페녹시)-6-메톡시코우마린; 4-(2,6-디브로모페녹시)-8-메톡시코우마린; 4-(2,6-디클로로페녹시)-8-메톡시코우마린; 4-(2,6-디클로로페녹시)-6,7-디메톡시코우마린; 4-(2,6-디클로로페녹시)-6,7-디메톡시코우마린; 4-(2,6-디클로로페녹시)-5,6,7-트리메톡시코우마린; 4-(2,6-디브로모페녹시)-5,6,7-트리메톡시코우마린; 4-(2,6-디클로로페녹시)-5,6,7-트리메톡시코우마린; 4-(2,6-디브로모페녹시)-5,6,7-트리메톡시코우마린; 4-(2,6-디클로로페녹시)-5,6,7-트리메톡시코우마린; 4-(2,6-디클로로페녹시)-5-(트리플루오로메톡시)코우마린; 4-(2,6-디브로모페녹시)-5-(트리플루오로메톡시)코우마린; 4-[(2-클로로-6-메틸)페녹시]-5-클로로코우마린; 4-[(2-클로로-6-메틸)페녹시]-5-클로로코우마린; 4-(2,6-디브로모페녹시)-5-클로로코우마린; 4-(2,6-디클로로페녹시)-5-클로로코우마린; 4-[(2-클로로-6-메틸)페녹시]-5-플루오로코우마린; 4-(2,6-디클로로페녹시)-5-플루오로코우마린;4-(2,6-디클로로페녹시)-5-메틸코우마린;4-[(2-클로로-6-메틸)페녹시]-5-메틸코우마린; 또는 4-(2,6-디클로로페녹시)-5-니트로코우마린인 방법.
- 하기 일반식 I의 화합물;상기 식에서, X 및 X'는 각각 독립적으로 할로겐, C1-C4알킬 또는 C2-C4알케닐이고; W, Y 및 Z는 각각 독립적으로 O 또는 S 이고; R은 일 내지 세개의H, 할로겐, C1-C4알킬, C3-C6시클로알킬, C1-C4할로알킬 또는 C1-C4알콕시 기의 임의의 조합이고; R1은 일 내지 네개의 H, 할로겐, OH,CN,NO2,SH 임의로 하나이상의 할로겐 또는 OR2기로 치환된 C1-C6알킬, C3-C6시클로알킬, C1-C6알킬티오, C2-C6알케닐, C2-C6할로알케닐, C2-C6알키닐, C2-C6할로알키닐, OR2, OCH2COOR3, OCH2OR4, OCOOR5, OCONHR6, OCOR7, S(O)nR8, COR9, CH(OR10)2, 임의로 일 내지 세개의 할로겐, CN, C1-C4알킬, C1-C4할로알킬, C1-C4알콕시 또는 C1-C4할로알콕시 기로 치환된 페닐, 또는 임의로 일 내지 세개의 할로겐, CN, C1-C4알킬, C1-C4할로알킬 또는 C1-C4알콕시 기로 치환된벤질의 임의의 조합이고; 단, 하나 이상의 R1는 H 이외의 것이어야 하고; R2는 H, C1-C4알킬, C1-C4할로알킬, C2-C6알케닐, C2-C6알키닐,C2-C6할로알케닐, 또는 C2-C6할로알키닐이고; R3,R4,R5,R6및 R7은 각각 독립적으로 H, C1-C4알킬, C1-C4할로알킬, C3-C6시클로알킬, 임의로 일 내지 세개의 할로겐, CN, C1-C4알킬, C1-C4할로알킬, C1-C4알콕시 또는 C1-C4할로알콕시 기로 치환된 페닐, 또는 임의로 일 내지 세개의 할로겐, C1-C4알킬, C1-C4할로알킬 또는 C1-C4알콕시 기로 치환된 벤질이고; R8은 C1-C4알킬, C1-C4할로알킬 또는 임의로 일 내지 세개의 할로겐, CN, C1-C4알킬, C1-C4할로알킬, C1-C4알콕시 또는 C1-C4할로알콕시 기로 치환된 페닐이고; R9는 H, OH, C1-C4알킬, C1-C4알콕시, 임의로 일 내지 세개의 할로겐, CN, C1-C4알킬, C1-C4할로알킬, C1-C4알콕시 또는 C1-C4할로알콕시 기로 치환된 페닐, 또는 임의로 일 내지 세개의 할로겐, C1-C4알킬, C1-C4할로알킬, C1-C4알콕시 또는 C1-C4할로알콕시 기로 치환된 벤질, 또는 NR11R12이고; R10은 H, C1-C4알킬 또는 -(CH2)m-이고; R11및 R12는 각각 독립적으로 H, C1-C4알킬, C2-C4알케닐이거나 또는 R11및 R12는 각각 독립적으로 H, C1-C4알킬, C2-C4알케닐이거나 또는 R11및 R12는 그들이 부착된 원자와함께 임의로 산소 원자가 중간에 있는 5- 또는 6- 원 고리를 형성하고; n은 0.1 또는 2이며, m은 2 또는 3이다.
- 제7항에 있어서, 4-(2,6-디클로로페녹시)-6-메톡시코우마린; 4-(2,6-디브로모페녹시)-8-메톡시코우마린; 4-(2,6-디클로로페녹시)-6,7-디메톡시코우마린; 4-(2,6-디브로모페녹시)-6,7-디메톡시코우마린; 4-(2,6-디클로로페녹시)-5,6,7-트리메톡시코우마린; 4-(2,6-디브로모페녹시)-5,6,7-트리메톡시코우마린;4-(2,6-디클로로페녹시)-5-(트리플루오로메틸)코우마린; 4-(2,6-디브로모페녹시)-5-(트리플루오로메톡시)코우마린; 4-[(2-클로로-6-메틸)페녹시]-5-클로로코우마린; 4-[(2-클로로-6-메틸)페녹시]-5-클로로코우마린; 4-(2,6-디브로모페녹시)-5-클로로코우마린; 4-(2,6-디클로로페녹시)-5-클로로코우마린; 4-[(2-클로로-6-메틸)페녹시]-5-플루오로코우마린; 4-(2,6-디클로로페녹시)-5-플루오로코우마린; 4-(2,6-디클로로페녹시)-5-메틸코우마린; 4-[(2-클로로-6-메틸)페녹시]-5-메틸코우마린; 또는 4-(2,6-디클로로페녹시)-5-니트로코우마린인 방법.
- 하기 일반식 I의 화합물 및 농경학적으로 허용가능한 부형제로 구성되는 제초제 조성물;상기 식에서, X,X',W,Y,Z,R 및 R1은 제7항에서 정의된 바와같다.
- 용매의 존재하에, 임의로 염기의 존재하에 하기 일반식 Ⅴ의 화합물을1몰 이상의 당량의 하기 일반식 Ⅵ의 화합물과 반응시키는 것으로 구성되는 하기 일반식 Ia의 화합물의 제조 방법;상기 식에서, X,X',W,Y,Z,R 및 R1은 제7항에서 정의된 바와같다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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US5808105A (en) * | 1995-10-10 | 1998-09-15 | American Cyanamid Company | 4-phenoxycoumarins as herbicidal agents |
CA2233666C (en) * | 1995-10-13 | 2006-05-09 | Agrevo Uk Limited | Heterocyclic fungicides |
CA2433578A1 (en) * | 2000-12-28 | 2002-07-11 | Koichi Niimura | Process for preparation of esculetin compounds, esculetin compounds and intermediates thereof, and use of both |
US7148253B2 (en) * | 2002-05-14 | 2006-12-12 | Xtl Biopharmaceuticals Ltd. | 4-thio coumarins |
WO2003097628A1 (en) * | 2002-05-14 | 2003-11-27 | Vivoquest, Inc. | 4-thio coumarins |
HRP20030603A2 (en) | 2003-07-25 | 2005-10-31 | Pliva-Istra�iva�ki institut d.o.o. | Substituted furochromene compounds of antiinflammatory action |
CN100405907C (zh) * | 2005-11-18 | 2008-07-30 | 党永富 | 一种除草剂安全添加剂 |
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CN104592183B (zh) * | 2015-01-15 | 2016-05-18 | 青岛农业大学 | N-酰基-n-间氟苄基-8-氨基香豆素类化合物及其制备与除草用途 |
CN106749144B (zh) * | 2016-12-27 | 2019-06-28 | 江苏大学 | 7-芳氧乙酰氧基香豆素类化合物及其在农药上的应用 |
CN109293616B (zh) * | 2018-09-29 | 2022-06-21 | 贵州大学 | 一种含香豆素查尔酮类衍生物、其制备方法及应用 |
CN112806361B (zh) * | 2019-11-18 | 2021-12-24 | 党永富 | 炭吸附4-羟基香豆素除草剂安全添加剂及其在治理除草剂副作用中的应用 |
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US5563280A (en) | 1996-10-08 |
TJ95000241A (en) | 1998-10-28 |
NO952940D0 (no) | 1995-07-24 |
JPH0873304A (ja) | 1996-03-19 |
LV10992B (en) | 1996-06-20 |
LV10992A (lv) | 1996-02-20 |
RU95113207A (ru) | 1997-06-27 |
CN1119188A (zh) | 1996-03-27 |
ZA956151B (en) | 1997-01-24 |
AU2715195A (en) | 1996-03-07 |
US5759959A (en) | 1998-06-02 |
US5681968A (en) | 1997-10-28 |
NO952940L (no) | 1996-01-26 |
IL114704A0 (en) | 1995-11-27 |
MD950364A (ro) | 1997-01-31 |
EE9500030A (et) | 1996-02-15 |
TR199500890A2 (tr) | 1996-06-21 |
BR9503417A (pt) | 1996-06-04 |
SK92995A3 (en) | 1996-02-07 |
TW318846B (ko) | 1997-11-01 |
HU9502218D0 (en) | 1995-09-28 |
CA2154408A1 (en) | 1996-01-26 |
HUT75945A (en) | 1997-05-28 |
EP0694257A1 (en) | 1996-01-31 |
CZ183195A3 (en) | 1996-02-14 |
PL309764A1 (en) | 1996-02-05 |
NZ272626A (en) | 1997-06-24 |
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