methyl 4-acetamido-3,6-dichloropicolinate | 350601-49-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: methyl 4-acetamido-3,6-dichloropicolinate
• 英文别名: methyl 4-(acetylamino)-3,6-dichloropyridine-2-carboxylate；Methyl 4-acetamido-3,6-dichloropyridine-2-carboxylate
• CAS: 350601-49-9
• 化学式: C₉H₈Cl₂N₂O₃
• 分子量: 263.08
• InChiKey: CSKIJJZFXAACON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-acetamido-3,6-dichloropicolinate 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium fluoride 、 乙酰氯 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 6.33h， 生成 methyl 4-amino-3-chloro-6-(4-chlorophenyl)picolinate
  参考文献：
  名称：

  The discovery of Arylex™ active and Rinskor™ active: Two novel auxin herbicides

  摘要：

  Multiple classes of commercially important auxin herbicides have been discovered since the 1940s including the aryloxyacetates (2,4-D, MCPA, dichlorprop, mecoprop, triclopyr, and fluroxypyr), the benzoates (dicamba), the quinoline-2-carboxylates (quinclorac and quinmerac), the pyrimidine-4-carboxylates (aminocyclopyrachlor), and the pyridine-2-carboxylates (picloram, clopyralid, and aminopyralid). In the last 10 years, two novel pyridine-2-carboxylate (or picolinate) herbicides were discovered at Dow AgroSciences. This paper will describe the structure activity relationship study that led to the discovery of the 6-aryl-picolinate herbicides Arylex (TM) active (2005) and Rinskor (TM) active (2010). While Arylex was developed primarily for use in cereal crops and Rinskor is still in development primarily for use in rice crops, both herbicides will also be utilized in additional crops. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.08.011
• 作为产物：
  描述：

  4-氨基-3,6-二氯吡啶-2-甲酸 在 硫酸 作用下， 反应 40.0h， 生成 methyl 4-acetamido-3,6-dichloropicolinate
  参考文献：
  名称：

  The discovery of Arylex™ active and Rinskor™ active: Two novel auxin herbicides

  摘要：

  Multiple classes of commercially important auxin herbicides have been discovered since the 1940s including the aryloxyacetates (2,4-D, MCPA, dichlorprop, mecoprop, triclopyr, and fluroxypyr), the benzoates (dicamba), the quinoline-2-carboxylates (quinclorac and quinmerac), the pyrimidine-4-carboxylates (aminocyclopyrachlor), and the pyridine-2-carboxylates (picloram, clopyralid, and aminopyralid). In the last 10 years, two novel pyridine-2-carboxylate (or picolinate) herbicides were discovered at Dow AgroSciences. This paper will describe the structure activity relationship study that led to the discovery of the 6-aryl-picolinate herbicides Arylex (TM) active (2005) and Rinskor (TM) active (2010). While Arylex was developed primarily for use in cereal crops and Rinskor is still in development primarily for use in rice crops, both herbicides will also be utilized in additional crops. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.08.011
• 作为试剂：
  描述：

  氟氯吡啶酯 、 4-氯-2-氟-3-甲氧基苯硼酸 在 4-氯-2-氟-3-甲氧基苯硼酸 、 methyl 4-acetamido-3,6-dichloropicolinate 、 4-甲基-2-戊酮 作用下， 以 4-甲基-2-戊酮 为溶剂， 以to produce methyl 4-(acetylamino)-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate, which的产率得到methyl 4-(acetylamino)-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate
  参考文献：
  名称：

  METHODS OF PRODUCING METHYL 4-AMINO-3-CHLORO-6-(4-CHLORO-2-FLUORO-3-METHOXYPHENYL)PYRIDINE-2-CARBOXYLATE

  摘要：

  制备甲基4-氨基-3-氯-6-(4-氯-2-氟-3-甲氧基苯基)吡啶-2-羧酸甲酯的方法。其中一种方法包括将甲基异丁酮加入含有4-氯-2-氟-3-甲氧基苯基硼酸的水溶液中，形成包含4-氯-2-氟-3-甲氧基苯基硼酸和水相的有机相。将有机相和水相分离。将4-氯-2-氟-3-甲氧基苯基硼酸与甲基4-(乙酰氨基)-3,6-二氯吡啶-2-羧酸甲酯在甲基异丁酮中反应，生成甲基4-(乙酰氨基)-3-氯-6-(4-氯-2-氟-3-甲氧基苯基)吡啶-2-羧酸甲酯，经脱乙酰化反应制得甲基4-氨基-3-氯-6-(4-氯-2-氟-3-甲氧基苯基)吡啶-2-羧酸甲酯。

  公开号：

  US20130172566A1

文献信息

• 6-(Poly-substituted aryl)-4-aminopicolinates and their use as herbicides
  申请人：Balko W. Terry

  公开号：US20070179060A1

  公开（公告）日：2007-08-02

  4-Aminopicolinic acids having tri- and tetra-substituted aryl substituents in the 6-position, and their amine and acid derivatives, are potent herbicides demonstrating a broad spectrum of weed control.

  在6位具有三取代和四取代芳基取代基的4-氨基吡啶酸及其胺和酸衍生物是一类高效除草剂，展示出广泛的杂草控制谱。
• PYRIDINE-BASED COMPOUND INCLUDING ISOXAZOLINE RING AND USE THEREOF AS HERBICIDE
  申请人：MOGHU RESEARCH CENTER LTD.

  公开号：US20190159450A1

  公开（公告）日：2019-05-30

  A pyridine-based compound containing an isoxazoline ring represented by Formula 1 or an agrochemically acceptable salt thereof can be used as a herbicide. A method of preparing the pyridine-based compound containing an isoxazoline ring represented by Formula 1 includes reacting a compound represented by Formula 2 with a compound represented by Formula 3.

  一种含有异噁唑啉环的吡啶基化合物，其化学式如下（Formula 1），或其农药可接受的盐，可用作除草剂。制备这种含有异噁唑啉环的吡啶基化合物的方法包括将化合物（Formula 2）与化合物（Formula 3）进行反应。
• 4-AMINO-6-(HALO-SUBSTITUTED-ALKYL)-PICOLINATES AND THEIR USE AS HERBICIDES
  申请人：Dow AgroSciences LLC

  公开号：US20150164074A1

  公开（公告）日：2015-06-18

  Provided herein are 4-amino-6-(halo-substituted-alkyl)-picolinic acids and their derivatives, compositions comprising the acids and their derivatives, and methods of use thereof as herbicides.

  本文提供了4-氨基-6-(卤代烷基取代)-吡啶甲酸及其衍生物，包括这些酸及其衍生物的组合物，以及将其用作除草剂的方法。
• METHODS FOR PRODUCING BORYLATED ARENES
  申请人：Dow AgroSciences, LLC

  公开号：US20150065743A1

  公开（公告）日：2015-03-05

  Methods for the selective borylation of arenes, including arenes substituted with an electron-withdrawing group (e.g., 1-chloro-3-fluoro-2-substituted benzenes) are provided. The methods can be used, in some embodiments, to efficiently and regioselectively prepare borylated arenes without the need for expensive cryogenic reaction conditions.

  提供了一种选择性硼化芳烃的方法，包括带有电子吸引基团的芳烃（例如，1-氯-3-氟-2-取代苯）。在某些实施方式中，这些方法可以用来高效和区域选择性地制备硼化芳烃，而无需昂贵的低温反应条件。
• 6-Aryl-4-aminopicolinates and their use as herbicides
  申请人：——

  公开号：US20030114311A1

  公开（公告）日：2003-06-19

  4-Aminopicolinic acids having aryl or heteroaryl substituents in the 6-position and their amine and acid derivatives are potent herbicides demonstrating a broad spectrum of weed control.

  在6位上具有芳基或杂环芳基取代基的4-氨基吡啶甲酸及其胺和酸衍生物是有效的除草剂，展示了广泛的杂草控制谱。