KR900003158A - 헤테로사이클릭 n-아실설폰아미드, 이의 제조방법, 이를 함유하는 약제 및 제초제 또는 성장 억제제로서의 이의 용도 - Google Patents

헤테로사이클릭 n-아실설폰아미드, 이의 제조방법, 이를 함유하는 약제 및 제초제 또는 성장 억제제로서의 이의 용도 Download PDF

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KR900003158A
KR900003158A KR1019890010964A KR890010964A KR900003158A KR 900003158 A KR900003158 A KR 900003158A KR 1019890010964 A KR1019890010964 A KR 1019890010964A KR 890010964 A KR890010964 A KR 890010964A KR 900003158 A KR900003158 A KR 900003158A
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오르트 오스발트
빌름스 로타르
바우에르 클라우스
비링거 헤르만
슐쯔 아르노
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베튼하르트 베크, 하인리히벡커
훽스트 아크티엔게젤샤프트
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Abstract

내용 없음

Description

헤테로사이클릭 N-아실설폰아미드, 이의 제조방법, 이를 함유하는 약제 및 제초제 또는 성장 억제제로서의 이의 용도
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (11)

  1. 일반식(Ⅰ)의 화합물 및 이의 염.
    상기식에서, R1은 수소, (C1-C4)-알킬, (C2-C6)-알케닐 또는 (C2-C6)-알키닐이고, R2및 R3는 서로 독립적으로 수소, (C1-C3)-알킬 또는 페닐이고, W는 O,S,NR4또는 NOR4이고, R4는 수소, (C1-C3)-알킬, (C1-C3)-할로알킬 또는 페닐이고, X는 CHR2, O, NR4또는 NOR4이고, L은 일반식(L1) 내지 (L5)의 헤테로사이클릭 또는 이소사이클릭 라디칼이고,
    A는 일반식(A1) 내지 (A8)의 헤테로사이클릭 라디칼이고,
    Z는 O 또는 S(O)q이고, E1은 O 또는 S(O)b이고, E2는 CH또는 N이고, E3는 O 또는 CH2이고, a,m,n,p,r 및 S는 독립적으로 0 또는 1이고, b 및 q는 서로 독립적으로 0,1 또는 2이고, R5는 수소; 할로겐; NO2; CN; (C1-C4)-알킬 (비치환된거나, F, Cl 또는 Br로 일치환 또는 다치환되거나, CN, OCH3또는 SCH3로 일치환된다); (C2-C4)-알케닐(비치환되거나 F, Cl 또는 Br로 일치환 또는 다치환되거나 OCH3로 일치환된다) ; (C2-C4)-알키닐(비치환되거나 F, Cl 또는 Br로 일치환 또는 다치환되거나 OCH3또는 Si(CH3)3로 일치환된다) ; (C3-C6)-사이클로알킬 (비치환되거나 F, Cl 또는 CH3로 일치환 또는 다치환된다) ; -C(O)R10, -OCH2CH2OR10, -OH, -C(R10)-(OR11)(OR12) ; -CO2R13, -C(O)NR14R15, -N3, -SO2NR14R15, -SO3R16, -OSO2R17, 페닐 (비치환되거나 F, Cl, Br, CH3또는 OCH3로 일치환 또는 다치환된다) ; -E1R18또는 -(CH2)sG이고, R6은 수소 또는 할로겐 ; CN; NO2; (C1-C4)-알킬 (비치환되거나 할로겐으로 일치환 또는 다치환되거나, -CO2R13, -SO2NR14R15, -NR14R15, (C1-C2)-알콕시, -E1R19, (C1-C2)-할로알콕시, (C1-C2)-알킬티오, (C1-C2)-할로알킬티오, CN, OH 또는 SH로 일 또는 이치환된다); -CO2R13, -SO2NR14R15, -NR14R15또는 -F1R19이고, R7은 서로 독립적으로 수소; (C1-C4)-알킬; (C1-C4)-할로알킬, (C2-C4)-알케닐; 페닐; 할로겐 또는 -E1R19로 일치환 또는 다치환된 페닐 ; -E1R19또는 할로겐이고, R8은 수소, (C1-C4)-알킬, (C1-C4)-할로알킬, 할로겐, -CO2R13-SO2NR14R15, -OSO2R17, -S(O)bR18, CN 또는 NO2이고, R9는 수소; (C1-C4)-알킬(비치환되거나 할로겐으로 일치환 또는 다치환되거나 페닐로 일치환된다) ; (C2-C4)알케닐 ; 페닐; 또는 할로겐, (C1-C4)-알킬, NO2, CN 또는 (C1-C4)-알콕시로 일 또는 다치환된 페닐이고, R10은 수소; (C1-C4)-알킬 ; F,Cl,Br 또는 OCH3로 일치환된 또는 다치환된 (C1-C4)-알킬; 비치환되거나 F,Cl, Br 또는 CH3로 일치환 또는 다치환된 (C3-C6)-사이클로알킬; (C2-C4)-알케닐 또는 (C2-C4)-알키닐이고, R11및 R12는 서로 독립적으로 (C1-C4)-알킬 또는 R11및 R12함께 -CH2CH2-, -CH2OCH2- 또는 -CH2(CCH3)2-CH2-이고, R13은 수소, (C1-C4)-알킬 (비치환되거나 할로겐으로 일치환 또는 다치환되거나 CN,CO2R10,NR14R15,OR10또는 Si(CH3)3에 의해 일치환 내지 이치환된다) ; (C3-C4)-알키닐 (비치환되거나 CH3또는 Si(CH3)3로 치환된다); (C3-C6)-사이클로알킬, (C3-C6)-사이클로알킬-(C1-C4)알킬, (C1-C4)-알콕시 또는 Si(CH3)3이고, R14는 수소, (C1-C4)-알킬이거나, R14및 R15가 함께는 -(CH2)2(CH2)a(CH2)2- 또는 -(CH2)2O(CH2)2-이고, R15는 수소, (C1-C4)-알킬, (C1-C4)-알콕시, (C2-C4)-알케닐이거나, R14및 R15가 함께는 -(CH2)2(CH2)a(CH2)2- 또는 -(CH2)2O(CH2)2-이고, R16은 (C1-C4)-알킬 또는 (C1-C4)-할로알킬이고, R17은 (C1-C4)-알킬 또는 NR14R15이고, R18은 (C1-C4)-알킬, (C1-C4)-할로알킬, (C2-C4)-알콕시알킬, (C2-C4)-알케닐, (C3-C4)-알키닐, 페닐 또는 할로겐, (C1-C3)-알킬, (C1-C3)-알콕시 또는 (C1-C3)-할로알킬로 일치환 또는 다치환된 페닐이고, R19는 (C1-C4)-알킬 또는 F 또는 Cl로 일치환 또는 다치환되거나 OR16으로 일치환된 (C1-C4)알킬이고, R20및 R21은 서로 독립적으로 수소, 할로겐, (C1-C6)-알킬, (C1-C6)-알콕시 또는 (C1-C6)-알킬티오 (위의 세 라디칼은 할로겐에 의해 일치환 또는 다치환되거나 (C1-C4)-알콕시 또는 (C1-C4)-알킬 티오에 의해 일치환 또는 이치환될 수 있다); -NR14R15, (C3-C6)-사이클로알킬, -OCHR14-CO2R13, (C2-C5)-알케닐, (C2-C4)-알키닐, (C3-C5)-알케닐옥시 또는 (C3-C5)-알키닐옥시이고, R22는 (C1-C4)-알킬 또는 (C1-C4)-할로알킬이고, R23및 R24는 각기 독립적으로 수소, (C1-C4)-알킬, (C2-C4)-알케닐 또는 (C2-C4)-알키닐이고, R25는 수소, (C1-C4)-알킬 또는 (C1-C4)-할로알킬이고, R26은 수소 또는 (C1-C3)-알킬이고, G는 일반식(G1) 내지 (G25)의 헤테로사이클라디칼이고,
    R27은 수소, (C1-C3)-알킬 또는 (C2-C4)-알케닐이다.
  2. 제1항에 있어서, A는 일반식(A1),(A2),(A3) 또는 (A4), 특히 (A1)의 라디칼이고, L은 일반식(L1),(L3),(L4) 또는 (L5)의 라디칼이고, X는 CH2,CH(CH3),O,NH,NCH3,NC2H5또는 NOCH3, 특히 CH2,O 또는 NH이고, W는 산소이고, R1은 수소이고, R2및 R3는 서로 독립적으로 수소 또는 (C1-C3)-알킬, 특히 수소이고, R5는 할로겐; NO2CN,(C1-C3)-알킬 (비치환되거나, F,Cl,Br,CN,OCH3또는 SCH3로 치환된다); (C3)-알케닐(비치환되거나 F,Cl 또는 Br로 치환된다), (C3)-알키닐, (C3)-사이클로알킬 (비치환되거나 F,Cl 또는 CH3로 치환된다) ; -C(O)R10, -OCH2CH2OR10,OH,-(CR10)(OR11)(OR12),-CO2R13,-(CO)NR14R15,N3,-SO2NR14R15,-OSO2R17,-F1R18또는 -(CH2)sG이고, R6은 수소, 할로겐, CN, NO2, CH3, CF3, -F1R19또는 (C1-C2)-알콕시-(C1-C2)-알킬, (C1-C2)-할로알콕시,(C1-C2)-알킬티오, (C1-C2)-할로알킬티오, CN, -CO2R13또는 -SO2NR14R15이고, R7은 수소이고, R10은 (C1-C3)-알킬, 사이클로프로필 또는 (C3)-알케닐이고, R11및 R12는 (C1-C2)-알킬 또는 R11및 R12함께 -CH2CH2-이고, R13은 (C1-C3)-알킬, (C3)-알케닐, -CH2CH2F-CH2CH2Cl, -CH2CH2OCH3또는 사이클로프로필메틸이고, R14는 수소 또는 CH3, 또는 R14및 R15는 함께 -(CH2)4-, -(CH2)5- 또는 -(CH2)2O(CH2)2-이고, R15는 CH3, CH2CH3또는 OCH3, 또는 R14및 R15는 함께 -(CH2)4-, -(CH2)5- 또는 -(CH2)2O(CH2)2-이고, R18은 (C1-C3)-알킬, (C1-C3)-할로알킬, (C2-C3)-알콕시알킬, 알릴, 프로파길 또는 (C2-C3)-할로알케닐이고, R19는 비치환되거나 F,Cl 또는 OCH3로 치환된 (C1-C2)알킬이고, R20및 R21은 서로 독립적으로 수소, (C1-C2)-알킬, (C1-C2)-알콕시, -CH2OCH3,Cl,F,Br,I,-CH2OCH2CH3, -NHCH3, -N(OCH3)CH3, -N(CH3)2, -CF3, -SCH3, -CH(OCH3)2, -OCH2CH=CH2, -OCH2CH, -OCH2CH2OCH3, -CH2SCH3, -OCHF2, -SCHF2, 사이클로프로필, -C CH 또는 -C C-CH3이고, m은 0 또는 1이고, n은 0또는 1이고, S는 0이고, E1은 산소 또는 S인 일반식(Ⅰ)의 화합물 및 이의 염.
  3. a)W=0인 화합물의 제조를 위해, a1)일반식(Ⅱ)의 화합물을 염기 존재하에 일반식(Ⅲ)의 화합물과 반응시키거나, a2)일반식(Ⅱa)의 화합물을 활성화제, 예를 들어, 2-클로로-1-메틸-파라디늄 크로라이드(Ⅳa), 디사이클로헥실카르보디이미드 (Ⅳb) 또는 1,1-카보닐디이미다졸(Ⅳc)존재하에 및 필요한 경우, 염기존재하에 일반식(Ⅲ)의 화합물과 반응시키거나, a3)W=0이고 R1=H인 화합물의 제조를 위해, 일반식(Ⅴ)화합물을 일반식(Ⅵ)화합물과 반응시키거나, b)W=S인 화합물의 제조를 위해, a)에서 수득된 일반식(Ⅰ)화합물을 일반식(Ⅶ)화합물과 반응시키거나, c)W=NR4인 화합물의 제조를 위해, 일반식(Ⅷ)의 화합물을 일반식, H2N-R4의 아민과 반응시키고, d)W=NOR4인 화합물의 제조를 위해, d1)일반식(Ⅸ)의 화합물을 알카리 금속 수산화물 또는 알칼리 토금속 수산화물, 또는 암모늄 하이드록 사이드와 반응시키거나, d2) 일반식(Ⅷ)의 화합물을 염기 존재하에 일반식 H2N-OR4의 하이드록실아민과 반응시키거나, e)R1≠i수소인 일반식(Ⅰ)의 화합물의 제조를 위해, R1=H인 일반식(Ⅰ)의 화합물을 RI-X1(여기에서, RI는 수소를 제외하고 R1에 대해 정의된 의미를 갖고 X1은 염소,브롬 또는 요오드이다)의 알킬 할라이드와 반응시키고 필요한 경우, 수득된 화합물을 이의 염으로 전환시킴을 특징으로 하는, 제1항에서 청구된 일반식(Ⅰ)의 화합물 및 이의 염을 제조하는 방법.
    상기식에서, A,R1,R2,R3,n,x,m 및 L은 상기 정의한 바와 같으며, M은 수소 또는 리튬이다.
  4. 일반식(Ⅱ')의 화합물.
    상기식에서, X'는 COCl,CN,Cl,F,Br,I,P-토실, 테트라알킬암모늄, N3,CO2R13,CO2CH2C6H5또는 E1R18이고, A,n,R13,E1및 R18은 제1항의 일반식(Ⅰ)에서 정의된 바와 같으며, 단, a)X'는 CO2CH3이고, n은 0이고, R20/R21은 OCH3/CH3이고, b)X'는 CO2C2H5이고, n은 O이고, R20및 R21은 각각 OC2H5이고, c)X1는 COOH 또는 CO2CH3이고, n은 0이고, R20및 R21은 각각 CH3이고, d)X1는 Cl이고, n은 1이고, R2및 R3는 H이고, R20및 R21은 OC2H5이고, e)X1는 CO2C2H5이고, n은 1이고, R2및 R3는 H이고, R20/R21은 CI/CH3이고, f)X1는 COOH 또는 COOCH3이고, n은 1이고, R2및 R3는 H이고, R20/R21은 벤질옥시/CH3,OCH3/CH3,OCH2H5/CH3, Cl/Cl, Cl/OCH3, OCH3/OCH3또는 Cl/CH3이고, g)X'는 COOC2H5이고, n은 1이고, R2및 R3는 H이고, R20/R21은 CH3/CH3, 또는 h) A는 A5이고, R20'은 H이고, R22는 CH3이고, n은 0이고, X'는 CO2C2H5또는 CO2CH3인 일반식(Ⅱ')화합물에 상응하거나, ⅰ) A는 A1이고, r은 0이고, E2는 N이고, n은 0이고, R20/R21은 CH3/CH3이고 X'는 CO2C2H5이고, j) A는 A1이고, r은 0이고, E2는 N이고, n은 1이고, R2및 R3는 H이고, R20/R21은 C1/OCH3또는 Cl/Cl이고 X는 CO2C2H5인 일반식(Ⅱ')의 화합물에 상응하는 화합물은 제외된다.
  5. 제4항에 있어서, A는 A1이고, r은 0이고, E2는 CH이고, X'는 CN,Cl,F,Br,I,N3,CO2R13,CO2CH2C6H5또는 E1R18(단, 제4항에서 a) 내지 g)하에 한정된 화합물은 제외된다)인 일반식(Ⅱ')의 화합물.
  6. 일반식(ⅩⅠ)의 화합물을 일반식(ⅩⅡ) 또는 (ⅩⅢ)의 화합물과 반응시킴을 특징으로 하여, A가 A1이고, r은 0이고, E2는 CH이고, X'는 CN,Cl,F,Br,I,N3,CO2R13, CO2CH2C6H5또는 E1R18이고, n,R13,E1및 R18은 제1항에서 정의된 바와 같은 일반식(Ⅱ')의 화합물 (단, X'가 CO2Et이고, n은 0이고, R20/R21은 OC2H5이거나, X'가 Cl이고, N은 1이고, R2및 R3는 H이고, R20/R21은 OC2H5인 화합물은 제외된다.)을 제조하는 방법.
  7. 제6항에 있어서, 반응을 염기 존재하에 반응조건하에서 불활성인 용매중에서, -78 내지 100℃의 온도에서 수행함을 특징으로 하는 방법.
  8. 유효량의 제2항의 일반식(Ⅰ)의 화합물 또는 이의 염 및 불활성 첨가제를 함유하는 제초체 또는 식물 성장조절제.
  9. 유효량의 제2항의 일반식(Ⅰ)의 화합물 또는 이의 염 및 불활성 첨가제를 함유하는 제초제 또는 식물 성장조절제.
  10. 제1항의 일반식(Ⅰ)의 화합물 또는 이의 염의 유효량을 식물 또는 경작 지역에 적용함을 특징으로 하여, 바람직하지 못한 식물을 방제, 또는 식물성장을 억제하는 방법.
  11. 제2항의 일반식(Ⅰ)의 화합물 또는 이의 염의 유효량을 식물 또는 경작 지역에 적용함을 특징으로 하여, 바람직하지 못한 식물을 방제, 또는 식물성장을 억제하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019890010964A 1988-08-02 1989-08-01 헤테로사이클릭 n-아실설폰아미드, 이의 제조방법, 이를 함유하는 약제 및 제초제 또는 성장 억제제로서의 이의 용도 KR900003158A (ko)

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DE3935277A1 (de) * 1989-10-24 1991-05-02 Hoechst Ag Sulfonierte heterocyclische carboxamide, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung als herbizide oder wachstumsregulatoren
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EP0353640B1 (de) 1995-04-12
IL91164A (en) 1994-11-28
NZ230136A (en) 1991-12-23
JP3117137B2 (ja) 2000-12-11
ZA895852B (en) 1990-04-25
DE3826230A1 (de) 1990-02-08
DE58909172D1 (de) 1995-05-18
PH26866A (en) 1992-11-16
ES2070870T3 (es) 1995-06-16
AU3914489A (en) 1990-02-08
AU636299B2 (en) 1993-04-29
EP0353640A3 (de) 1991-05-08
HUT55001A (en) 1991-04-29
US5053072A (en) 1991-10-01
DD283915A5 (de) 1990-10-31
DK377389A (da) 1990-02-03
DK377389D0 (da) 1989-08-01
EP0353640B2 (de) 2003-10-15
EP0353640A2 (de) 1990-02-07
JPH02282371A (ja) 1990-11-19
BR8903885A (pt) 1990-03-20
IL91164A0 (en) 1990-03-19
ES2070870T5 (es) 2004-06-16

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