4-(bromomethyl)-5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl) 1H-pyrazole | 656825-78-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(bromomethyl)-5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl) 1H-pyrazole
• 英文别名: 4-(bromomethyl)-5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazole；4-bromomethyl-5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole；4-(bromomethyl)-5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)pyrazole
• CAS: 656825-78-4
• 化学式: C₇H₆BrF₅N₂O
• 分子量: 309.033
• InChiKey: CXLRTEKQMOULAX-UHFFFAOYSA-N

物化性质

• 沸点：
  253.7±40.0 °C(Predicted)
• 密度：
  1.81±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(bromomethyl)-5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl) 1H-pyrazole 在 N-溴代丁二酰亚胺(NBS) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 10.0h， 生成 5-bromo-2-({[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfanyl)-1,3-oxazole
  参考文献：
  名称：

  2-[(1H-PYRAZOL-4-YLMETHYL) -SULFONYL] -OXAZOL-DERIVATIVE, 2-[(1H-PYRAZOL-4-YLMETHYL) -SULFANYL] -OXAZOL-DERIVATIVES, AND CHIRAL 2-[(1H-PYRAZOL-4-YMETHYL)SULFINYL]OXAZOLE DERIVATIVES, METHODS FOR THE PRODUCTION THEREOF AS HERBICIDES AND PLANT GROWTH REGULATORS

  摘要：

  本发明涉及2-[(1H-吡唑-4-基甲基)-磺酰基]-噁唑衍生物、手性的2-[(1H-吡唑-4-基甲基)-亚磺酰基]-噁唑衍生物和2-[(1H-吡唑-4-基甲基)-硫基]-噁唑衍生物的一般式（I）及其盐，其制备方法以及用作除草剂和植物生长调节剂，特别是用作选择性控制作物杂草的除草剂。

  公开号：

  US20110039696A1
• 作为产物：
  描述：

  5-(difluoromethoxy)-1,4-dimethyl-3-(trifluoromethyl)-1H-pyrazole 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 5.0h， 以89%的产率得到4-(bromomethyl)-5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl) 1H-pyrazole
  参考文献：
  名称：

  [EN] 1,3,4-THIADIAZOLES HAVING A HERBICIDAL ACTIVITY, THEIR AGRONOMICAL COMPOSITIONS AND RELATIVE USE
  [FR] 1,3,4-THIADIAZOLES PRÉSENTANT UNE ACTIVITÉ HERBICIDE, LEURS COMPOSITIONS AGRONOMIQUES ET UTILISATION ASSOCIÉE

  摘要：

  本发明涉及一种具有通式(I)的新噻二唑衍生物，以及它们作为除草剂的用途。

  公开号：

  WO2016042435A1

文献信息

• [EN] PROCESS AND INTERMEDIATES FOR THE PREPARATION OF PYROXASULFONE, FENOXASULFONE AND VARIOUS SULFONE ANALOGS OF 5,5-DIMETHYL-4H-1,2-OXAZOLE<br/>[FR] PROCÉDÉ ET INTERMÉDIAIRES POUR LA PRÉPARATION DE PYROXASULFONE, DE FENOXASULFONE ET DE DIVERS ANALOGUES DE SULFONE DE 5,5-DIMÉTHYL-4H-1,2-OXAZOLE
  申请人：ADAMA AGAN LTD

  公开号：WO2022009044A1

  公开（公告）日：2022-01-13

  The invention relates to a process for preparing immediate precursors for pyroxasulfone and fenoxasulfone preparation of the formula (I). The process comprises a bromination reaction of a benzylic position without light irradiation (step a), followed by thoination reaction, which substitutes the bromine atom (step b) and after the protecting group is removed, and the revealed thiol or thiolate reacts with a substituted isoxazoline bearing a leaving group at the 3-position (step c), wherein Y = protecting group. In another variant of the invention the pyroxasulfone or fenoxasulfone immediate precursor is synthesized from the arylmethyl bromide by first forming a carbon-sulfur bond at the 3-position of a 2-isoxazoline through displacement of a leaving group at the 3-position (particularly acid derived residues such as phosphoryl, sulfanyl, halo, cyano or carboxyl groups) by an appropriate thionating reagent. The resulting adducts, which is a S-protected 3-thio-2-isoxazoline, may be treated with base to remove the protecting group, to reveal a thiol or thiolate which may subsequently react with the arylmethyl bromide to form the Pyroxasulfone or Fenoxasulfone immediate precursor. Ar = aryl, Y = protecting group and X = leaving group.

  本发明涉及一种制备式(I)中的吡罗砜和芬氧砜的直接前体的方法。该方法包括在没有光照射的情况下对苯基位置进行溴化反应（步骤a），然后进行硫酰化反应，以取代溴原子（步骤b），并在去除保护基后，暴露的巯基或巯酸盐与在3位带有离去基团的取代异噁唑啉发生反应（步骤c），其中Y = 保护基。在本发明的另一种变体中，通过首先通过适当的硫化试剂将碳硫键形成在2-异噁唑啉的3位上，以取代3位的离去基团（特别是酸衍生残基，如磷酰基，硫酰基，卤素，氰或羧基团），从而合成了吡罗砜或芬氧砜的直接前体。生成的产物是S-保护的3-硫代-2-异噁唑啉，可以用碱处理以去除保护基，暴露出巯基或巯酸盐，随后可以与苯基甲基溴反应，形成吡罗砜或芬氧砜的直接前体。Ar = 芳基，Y = 保护基，X = 离去基团。
• Chiral 2-(benzylsulfinyl)Thiazole derivatives and 2-[(1H-pyrazol-4-ylmethyl)sulfinyl]thiazole derivatives, processes for their preparation and their use as herbicides and plant growth regulators
  申请人：Dietrich Hansjörg

  公开号：US20100285958A1

  公开（公告）日：2010-11-11

  The present invention provides chiral 2-(benzylsulfinyl)thiazole derivatives and 2-[(1H-pyrazol-4-ylmethyl)sulfinyl]thiazole derivatives of the formula (I) and their salts processes for their preparation and their use as herbicides and plant growth regulators, in particular as herbicides for the selective control of harmful plants in crops of useful plants.

  本发明提供手性2-(苄基亚磺酰基)噻唑衍生物和2-[(1H-吡唑-4-基)甲基]亚磺酰基噻唑衍生物的公式(I)及其盐，其制备过程和作为除草剂和植物生长调节剂的用途，特别是作为用于选择性控制有害植物在有用植物作物中的除草剂。
• Pyrazole derivatives and process for the production thereof
  申请人：Nakatani Masao

  公开号：US20050215797A1

  公开（公告）日：2005-09-29

  The present invention provides pyrazole derivatives useful as production intermediates for isoxazoline derivatives having an excellent herbicidal effect and selectivity between crops and weeds as well as processes for producing the same. The pyrazole derivatives or pharmaceutically acceptable salts thereof which are inventive compounds are represented by the general formula [I] or a salt thereof: wherein R 1 represents a C1 to C6 alkyl group, R 2 represents a C1 to C3 haloalkyl group, R 3 represents a hydrogen atom, a C1 to C3 alkyl group which may be substituted with one or more substituents selected from the following substituent group α, or a formyl group, R 4 represents a hydrogen atom or a C1 to C3 haloalkyl group, provided that R 4 represents a C1 to C3 haloalkyl group in the case that R 3 is a hydrogen or a formyl group, and R 4 is a hydrogen group or a C1 to C3 haloalkyl group in the case that R 3 is a C1 to C3 alkyl group which may be substituted with one or more substituents selected from the following substituent group α.

  本发明提供了吡唑衍生物，用作制备具有优异除草效果和作物与杂草之间选择性的异恶唑衍生物的生产中间体，以及制备它们的方法。发明化合物为吡唑衍生物或其药学上可接受的盐，其由通式[I]或其盐表示：其中，R1代表C1至C6烷基，R2代表C1至C3卤代烷基，R3代表氢原子，C1至C3烷基，其可以被以下取代基α中的一个或多个取代基取代，或者甲酰基，R4代表氢原子或C1至C3卤代烷基，前提是当R3为氢或甲酰基时，R4代表C1至C3卤代烷基，在R3为C1至C3烷基且可以被以下取代基α中的一个或多个取代基取代时，R4代表氢原子或C1至C3卤代烷基。
• Novel Herbicides
  申请人：Black Janice

  公开号：US20090042726A1

  公开（公告）日：2009-02-12

  Compounds of formula I: wherein R 1 , R 2 , R 3 , R 4 , m, R 5 , R 6 , n and Y are as defined in claim 1 ; or N-oxides, salts and optical isomers thereof. Furthermore, the present invention relates to processes for preparing compounds of formula (I), to herbicidal compositions comprising them and to methods of using them to control plants or to inhibit plant growth.

  公式I的化合物：其中R1、R2、R3、R4、m、R5、R6、n和Y如权利要求1所定义；或其N-氧化物、盐和光学异构体。此外，本发明还涉及制备公式(I)化合物的方法，包括它们的除草剂组合物和使用它们控制植物或抑制植物生长的方法。
• 2-[(1H-pyrazole-4-ylmethyl)-sulfonyl]-oxazole-derivative, 2-[(1H-pyrazole-4-ylmethyl)-sulfanyl]-oxazole-derivatives, and chiral 2-[(1H-pyrazole-4-ymethyl)sulfinyl]oxazole derivatives, methods for the production thereof, and use thereof as herbicides and plant growth regulators
  申请人：Bayer Cropscience AG

  公开号：US08216973B2

  公开（公告）日：2012-07-10

  The invention relates to 2-[(1H-pyrazol-4-ylmethyl)-sulfonyl]-oxazole derivatives, chiral 2-[(1H-pyrazol-4-ylmethyl)-sulfinyl]-oxazole derivatives, and 2-[(1H-pyrazol-4-ylmethyl)-sulfanyl]-oxazole derivatives of general formula (I) and the salts thereof, methods for the production thereof, and the use thereof as herbicides and plant growth regulators, in particular as herbicides for selectively controlling weeds in plant crops.

  本发明涉及一种通式(I)的2-[(1H-吡唑-4-基甲基)-磺酰基]-噁唑衍生物、手性的2-[(1H-吡唑-4-基甲基)-亚磺酰基]-噁唑衍生物和2-[(1H-吡唑-4-基甲基)-硫基]-噁唑衍生物及其盐，以及其制备方法和作为除草剂和植物生长调节剂的用途，特别是作为选择性控制作物杂草的除草剂。