2-methyl-6-(trifluoromethoxy)benzenesulfonamide | 1261609-36-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methyl-6-(trifluoromethoxy)benzenesulfonamide
• CAS: 1261609-36-2
• 化学式: C₈H₈F₃NO₃S
• 分子量: 255.218
• InChiKey: NXUUQWKJZOYTJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-methyl-6-(trifluoromethoxy)benzenesulfonamide 、 5,7-二甲基-[1,2,4]三唑并[1,5-a]嘧啶-2-羧酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 5,7-dimethyl-N-(2-methyl-6-(trifluoromethoxy)phenylsulfonyl)-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxamide
  参考文献：
  名称：

  Design and synthesis of triazolopyrimidine acylsulfonamides as novel anti-mycobacterial leads acting through inhibition of acetohydroxyacid synthase

  摘要：

  Novel triazolopyrimidine acylsulfonamides class of antimycobacterial agents, which are mycobacterial acetohydroxyacid synthase (AHAS) inhibitors were designed by hybridization of known AHAS inhibitors such as sulfonyl urea and triazolopyrimidine sulfonamides. This Letter describes the synthesis and SAR studies of this class of molecules by variation of two parts of the molecule, the phenyl and triazolopyrimidine rings. SAR study describes optimisation of enzyme potency, whole cell potency and evidence of mechanism of action. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.054
• 作为产物：
  描述：

  2-methyl-6-(trifluoromethoxy)benzenesulfonyl chloride 在 ammonium hydroxide 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 2-methyl-6-(trifluoromethoxy)benzenesulfonamide
  参考文献：
  名称：

  Design and synthesis of triazolopyrimidine acylsulfonamides as novel anti-mycobacterial leads acting through inhibition of acetohydroxyacid synthase

  摘要：

  Novel triazolopyrimidine acylsulfonamides class of antimycobacterial agents, which are mycobacterial acetohydroxyacid synthase (AHAS) inhibitors were designed by hybridization of known AHAS inhibitors such as sulfonyl urea and triazolopyrimidine sulfonamides. This Letter describes the synthesis and SAR studies of this class of molecules by variation of two parts of the molecule, the phenyl and triazolopyrimidine rings. SAR study describes optimisation of enzyme potency, whole cell potency and evidence of mechanism of action. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.054

文献信息

• Substituierte Arylsulfonyl(thio)harnstoffe als Herbizide
  申请人：Bayer CropScience AG

  公开号：EP1683789A1

  公开（公告）日：2006-07-26

  Die Erfindung betrifft neue substituierte Arylsulfonyl(thio)harnstoffe in welcher Afür Stickstoff oder eine CH-Gruppierung steht, Qfür Sauerstoff oder Schwefel steht, R1für Wasserstoff, Halogen oder jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkylthio, Alkylamino, Dialkylamino, Cycloalkyl, Cycloalkyloxy oder Heterocyclyloxy steht, R2für Wasserstoff, Halogen oder jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkylthio, Alkylamino, Dialkylamino, Cycloalkyl, Cycloalkyloxy oder Heterocyclyloxy steht, R3für Wasserstoff oder gegebenenfalls substituiertes Alkyl steht, R4für jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkenyl, Alkinyl, Alkenyloxy, Alkinyloxy, Cycloalkyl, Cycloalkyloxy oder Cycloalkylalkyl steht, und R5für Wasserstoff, Formyl oder jeweils gegebenenfalls substituiertes Alkyl, Alkylcarbonyl, Alkoxycarbonyl, Alkylsulfonyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkylcarbonyl, Cycloalkylsulfonyl oder Heterocyclyl steht, sowie Salze von Verbindungen der Formel (I), wobei die Verbindung N-(4,6-Dimethyl-pyrimidin-2-yl)-N'-[2-(1,1,2,2-tetrafluorethoxy)-6-methyl-phenylsulfonyl]-harnstoff ausgenommen ist, Verfahren zur Herstellung der neuen Verbindungen und ihre Verwendung als Herbizide.

  本发明涉及新的取代芳基磺酰基（硫代）脲 其中 A代表氮或CH基团、 Q代表氧或硫 R1 代表氢、卤素或在每种情况下可选择取代的烷基、烷氧基、烷硫基、烷基氨基、 二烷基氨基、环烷基、环烷氧基或杂环氧基、 R2 代表氢、卤素或在每种情况下任选取代的烷基、烷氧基、烷硫基、烷基氨基、 二烷基氨基、环烷基、环烷氧基或杂环氧基、 R3 代表氢或任选取代的烷基、 R4 在每种情况下代表任选取代的烷基、烷氧基、烯基、炔基、烯氧基、炔氧基、环烷基、环烷氧基或环烷基，以及 R5 代表氢、甲酰基或在每种情况下被任选取代的烷基、烷基羰基、烷氧基羰基、烷基磺酰基、烯基、炔基、环烷基、环烷基羰基、环烷基磺酰基或杂环烷基、 以及式（I）化合物的盐类、 其中不包括化合物 N-(4,6-二甲基嘧啶-2-基)-N'-[2-(1,1,2,2-四氟乙氧基)-6-甲基苯基磺酰基]脲、 新化合物的制备工艺及其作为除草剂的用途。
• Substituted aryl sulphonyl(thio)ureas
  申请人：——

  公开号：US20030153463A1

  公开（公告）日：2003-08-14

  The invention relates to novel substituted arylsulphonyl(thio)ureas 1 in which A represents nitrogen or a CH grouping, Q represents oxygen or sulphur, R 1 represents hydrogen, halogen or respectively optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, cycloalkyl, cycloalkyloxy or heterocyclyloxy, R 2 represents hydrogen, halogen or respectively optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, cycloalkyl, cycloalkyloxy or heterocyclyloxy, R 3 represents hydrogen or optionally substituted alkyl, R 4 represents respectively optionally substituted alkyl, alkoxy, alkenyl, alkinyl, alkenyloxy, alkinyloxy, cycloalkyl, cycloalkyloxy or cycloalkylalkyl, and R 5 represents hydrogen, formyl or respectively optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, alkenyl, alkinyl, cycloalkyl, cycloalkylcarbonyl, cycloalkylsulphonyl or heterocyclyl, and to salts of compounds of the formula (I), except for the compound N-(4,6-dimethyl-pyrimidin-2-yl)-N′-[2-(1,1,2,2-tetrafluoro-ethoxy)-6-methyl-phenylsulphonyl]-urea, to processes for preparing the novel compounds and to their use as herbicides.

  本发明涉及新型取代的芳基磺酰基（硫代）脲类化合物 1 其中 A 代表氮或 CH 基团、 Q 代表氧或硫、 R 1 分别代表氢、卤素或任选取代的烷基、烷氧基、烷硫基、烷基氨基、二烷基氨基、环烷基、环烷氧基或杂环氧基、 R 2 分别代表氢、卤素或任选取代的烷基、烷氧基、烷硫基、烷基氨基、二烷基氨基、环烷基、环烷氧基或杂环氧基、 R 3 代表氢或任选取代的烷基、 R 4 分别代表任选取代的烷基、烷氧基、烯基、炔基、烯氧基、炔氧基、环烷基、环烷氧基或环烷基烷基，以及 R 5 分别代表氢、甲酰基或任选取代的烷基、烷基羰基、烷氧基羰基、烷基磺酰基、烯基、炔基、环烷基、环烷基羰基、环烷基磺酰基或杂环基、 以及式 (I) 化合物的盐、 化合物 N-(4,6-二甲基嘧啶-2-基)-N′-[2-(1,1,2,2-四氟-乙氧基)-6-甲基苯基磺酰基]-脲除外、 新型化合物的制备工艺及其作为除草剂的用途。
• [DE] SUBSTITUIERTE ARYLSULFONYL(THIO)HARNSTOFFE ALS HERBIZIDE<br/>[EN] SUBSTITUTED ARYL SULPHONYL(THIO)UREAS USED AS HERBICIDES<br/>[FR] ARYLSULFONYL(THIO)UREES SUBSTITUEES UTILISEES COMME HERBICIDES
  申请人：BAYER AKTIENGESELLSCHAFT

  公开号：WO1997032861A1

  公开（公告）日：1997-09-12

  (DE) Die Erfindung betrifft neue substituierte Arylsulfonyl(thio)harnstoffe der Formel (I), in welcher: A für Stickstoff oder eine CH-Gruppierung steht; Q für Sauerstoff oder Schwefel steht; R1 für Wasserstoff, Halogen oder jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkylthio, Alkylamino, Dialkylamino, Cycloalkyl, Cycloalkyloxy oder Heterocyclyloxy steht; R2 für Wasserstoff, Halogen oder jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkylthio, Alkylamino, Dialkylamino, Cycloalkyl, Cycloalkyloxy or Heterocyclyloxy steht; R3 für Wasserstoff oder gegebenenfalls substituiertes Alkyl steht; R4 für jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkenyl, Alkinyl, Alkenyloxy, Alkinyloxy, Cycloalkyl, Cycloalkyloxy oder Cycloalkylalkyl steht; und R5 für Wasserstoff, Formyl oder jeweils gegebenenfalls substituiertes Alkyl, Alkylcarbonyl, Alkoxycarbonyl, Alkylsulfonyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkylcarbonyl, Cycloalkylsulfonyl oder Heterocyclyl steht; sowie Salze von Verbindungen der Formel (I), wobei die Verbindung N-(4,6-Dimethyl-pyrimidin-2-yl)-N'-[2-(1,1,2,2-tetrafluorethoxy)-6-methyl-phenylsulfonyl]-harnstoff ausgenommen ist, Verfahren zur Herstellung der neuen Verbindungen und ihre Verwendung als Herbizide.(EN) The invention relates to novel substitued aryl sulphonyl(thio)ureas of formula (I) and salts thereof, in which: A is nitrogen or a CH group; Q is oxygen or sulphur; R1 is hydrogen, halogen or possibly substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, cycloalkyl, cycloalkyloxy or heterocyclyloxy; R2 is hydrogen, halogen or possibly substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, cycloalkyl, cycloalkyloxy or heterocyclyloxy; R3 is hydrogen or possibly substituted alkyl; R4 is possibly substituted alkyl, alkoxy, alkenyl, alkinyl, alkenyloxy, alkinyloxy, cycloalkyl, cycloalkyloxy or cycloalkylalkyl; and R5 is hydrogen, formyl or possibly substituted alkyl, alkylcarbonyl, alcoxycarbonyl, alkylsulfonyl, alkenyl, alkynyl, cycloalkyl, cycloalkylcarbonyl, cycloalkylsulfonyl or heterocyclyl; except for the compound N-(4,6-dimethyl-pyrimidin-2yl)-N'-(2-(1,1,2,2-tetrafluorethoxy)-6-methyl-phenylsulfonyl)-urea. Process for producing the novel compounds and their use as herbicides.(FR) L'invention concerne de nouvelles arylsulfonyl(thio)urées substituées de formule (I) et leurs sels. Dans la formule, A désigne azote ou un groupe CH; Q désigne oxygène ou soufre; R1 désigne hydrogène, halogène ou l'un des radicaux suivants éventuellement substitués: alkyle, alcoxy, alkylthio, alkylamino, dialkylamino, cycloalkyle, cycloalkyloxy ou hétérocyclyloxy; R2 désigne hydrogène, halogène ou l'un des radicaux suivants éventuellement substitués: alkyle, alcoxy, alkylthio, alkylamino, dialkylamino, cycloalkyle, cycloalkyloxy ou hétérocyclyloxy; R3 désigne hydrogène ou alkyle le cas échéant substitué; R4 désigne alkyle, alcoxy, alcényle, alcinyle, alcényloxy, alcinyloxy, cycloalkyle, cycloalkyloxy ou cycloalkylalkyle le cas échéant substitués; et R5 désigne hydrogène, formyle ou l'un des radicaux suivants: alkyle, alkylcarbonyle, alcoxycarbonyle, alkylsulfonyle, alcényle, alcinyle, cycloalkyle, cycloalkylcarbonyle, cycloalkylsulfonyle ou hétérocyclyle. Le composé N-(4,6-diméthyl-pyrimidin-2yl)-N'-(2-(1,1,2,2-tétrafluoréthoxy)-6-méthyl-phénylsulfonyl)-urée est exclu. L'invention concerne également des procédés de préparation de ces nouveaux composés et leur utilisation comme herbicides.

  本发明涉及一种新型取代的aryl sulfonyl(thio)urea(I)及其盐类，其中：A表示氮或CH-基团；Q表示氧或硫；R1表示氢、卤素或可能代替的 alkyl、 alkoxy、 alkylthio、 alkylamino、 dialkylamino、 cycloalkyl、 cycloalkyloxy或 heterocyclyloxy；R2表示氢、卤素或可能代替的 alkyl、 alkoxy、 alkylthio、 alkylamino、 dialkylamino、 cycloalkyl、 cycloalkyloxy或 heterocyclyloxy；R3表示氢或可能代替的 alkyl；R4表示可能代替的 alkyl、 alkoxy、 alkenyl、 alkinyl、 alkenyloxy、 alkinyloxy、 cycloalkyl、 cycloalkyloxy或 cycloalkylalkyl；且 R5表示氢、 formyl 或可能代替的 alkyl、 alkylcarbonyl、 alkoxy carbonyl、 alkylsulfonyl、 alkenyl、 alkinyl、 cycloalkyl、 cycloalkylcarbonyl、 cycloalkylsulfonyl或 heterocyclyl。并且除化合物 N-(4,6-dimethyl-pyrimidin-2yl)-N'-(2-(1,1,2,2-tetrafluorethoxy)-6-methyl-phenylsulfonyl)-urea 之外，本发明还涉及制备这种新型化合物的方法及其作为除草剂的用途。
• SUBSTITUIERTE ARYLSULFONYL(THIO)HARNSTOFFE ALS HERBIZIDE
  申请人：BAYER AG

  公开号：EP0885200A1

  公开（公告）日：1998-12-23
• Substituted aryl sulphonyl(thio)ureas used as herbicides
  申请人：Gesing Rudolf F. Ernst

  公开号：US20050004123A1

  公开（公告）日：2005-01-06

  The invention relates to novel substituted arylsulphonyl(thio)ureas in which A represents nitrogen or a CH grouping, Q represents oxygen or sulphur, R 1 represents hydrogen, halogen or respectively optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, cycloalkyl, cycloalkyloxy or heterocyclyloxy, R 2 represents hydrogen, halogen or respectively optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, cycloalkyl, cycloalkyloxy or heterocyclyloxy, R 3 represents hydrogen or optionally substituted alkyl, R 4 represents respectively optionally substituted alkyl, alkoxy, alkenyl, alkinyl, alkenyloxy, alkinyloxy, cycloalkyl, cycloalkyloxy or cycloalkylalkyl, and R 5 represents hydrogen, formyl or respectively optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, alkenyl, alkinyl, cycloalkyl, cycloalkylcarbonyl, cycloalkylsulphonyl or heterocyclyl, and to salts of compounds of the formula (I), except for the compound N-( 4,6 -dimethyl-pyrimidin- 2 -yl)-N′-[ 2 -( 1,1,2,2 -tetrafluoro-ethoxy)- 6 -methyl-phenylsulphonyl]-urea, to processes for preparing the novel compounds and to their use as herbicides.