(4-氯-2-氟苯基)-氨基甲酸乙酯 | 114108-90-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (4-氯-2-氟苯基)-氨基甲酸乙酯
• 英文名称: ethyl N-(4-chloro-2-fluorophenyl)carbamate
• 英文别名: ethyl-(4-chloro-2-fluorophenyl)carbamate；ethyl 4-chloro-2-fluorocarbanilate；Ethyl (4-chloro-2-fluorophenyl)carbamate
• CAS: 114108-90-6
• 化学式: C₉H₉ClFNO₂
• mdl: MFCD03389083
• 分子量: 217.627
• InChiKey: DDGKFWFDDFPLAO-UHFFFAOYSA-N

物化性质

• 沸点：
  228.5±30.0 °C(Predicted)
• 密度：
  1.347±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-氯-2-氟苯基)-氨基甲酸乙酯 在 氯 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 5-tert-Butyl-4,5-dichloro-3-(4-chloro-2-fluoro-phenyl)-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis and Herbicidal Activities of 4-Substituted 3-Aryl-5-tert-butyl-4-oxazolin-2-ones

  摘要：

  A series of novel 3-aryl-5-tert-butyl-4-chloro-4-oxazolin-2 (16) have been prepared and found to show significant herbicidal activity in the grams per are range against broadleaf and narrowleaf weeds. The key step in the introduction of the chlorine atom at the 4-position of the 4-chloro-4-oxazolin-2-one ring is dichlorination using chlorine gas and subsequent dehydrochlorination using diazabicyclo[5.4.0]undecene. 4-Alkylthio- and 4-methyl-4-oxazolin-2-one rings were synthesized from alpha-substituted alpha-bromopinacolone by cyclization reaction. Among the synthesized compounds, 5-tert-butyl-4-chloro-3-[4-chloro-2-fluoro-5-(2-propynyloxy)phenyl]-4-oxazolin-2-one (16h) showed the greatest activity against several weeds without damage to transplanted rice in the paddy field.

  DOI：

  10.1021/jf980281i
• 作为产物：
  描述：

  4-氯-2-氟苯胺 、 氯甲酸乙酯 在 吡啶 作用下， 反应 3.0h， 以95%的产率得到(4-氯-2-氟苯基)-氨基甲酸乙酯
  参考文献：
  名称：

  抑制原卟啉原氧化酶的除草剂环丙基酯和酰胺取代的嘧啶二酮的合成

  摘要：

  原卟啉原氧化酶（PPO）参与叶绿素的生物合成，是开发新型除草剂的重要目标。在这项研究中，从市售的2-（1-（巯基甲基）环丙基）乙酸合成了具有硫酯尾基的具有环丙基部分的新型嘧啶二酮化合物。还评估了合成化合物的除草活性。大多数合成的化合物对单子叶和双子叶杂草均表现出除草活性。特别地，10a显示出与对照材料沙氟芬那类似的活性。而对单子叶杂草，当稗草和马唐，10A 表现出比氟苯那西更高的活性。

  DOI：

  10.1002/bkcs.12205

文献信息

• 3-Aryluracils having an ether (thio) carbomyloxy or sulphomyloxy
  申请人：Hoffmann-La Roche Inc.

  公开号：US04859229A1

  公开（公告）日：1989-08-22

  The invention is concerned with 3-aryluracils of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are as described herein, as well as salts thereof and their manufacture, weed control compositions which contain such compounds as the active substance and the use of the active substances or compositions for weed control. The invention is also concerned with herbicidally-active starting materials and weed control compositions containing these.

  这项发明涉及式子##STR1##中的3-芳基尿嘧啶，其中R.sup.1、R.sup.2、R.sup.3、R.sup.4、R.sup.5和R.sup.6如本文所述，以及它们的盐及其制备方法，含有这些化合物作为活性物质的除草剂组合物以及利用这些活性物质或组合物进行除草的用途。该发明还涉及具有除草活性的起始材料和含有这些起始材料的除草剂组合物。
• A Novel Synthesis of 3-Aryl-5-tert-butyl-4-oxazolin-2-ones.
  作者：Noriaki KUDO、Misa TANIGUCHI、Kazuo SATO

  DOI：10.1248/cpb.44.699

  日期：——

  An efficient synthetic method for 3-aryl-5-butyl-4-oxazolin-2-ones (6) is described. The reaction of ethyl N-arylcarbamates (10) with 1-bromo-3, 3-dimethyl-2-butanone (9a) or 1-bromo-3-ethyl-3-methyl-2-pentanone (9b) using 2.2 eq of lithium bis(trimethylsilyl)amide afforded 6 in good yields. The reaction mechanisms are discussed.

  一种合成3-芳基-5-丁基-4-恶唑啉-2-酮（6）的高效合成方法被描述。通过使用2.2当量的双(三甲基硅基)胺锂，将N-芳基氨基甲酸乙酯（10）与1-溴-3,3-二甲基-2-丁酮（9a）或1-溴-3-乙基-3-甲基-2-戊酮（9b）反应，可以得到较高产率的6。同时，反应机理也进行了讨论。
• Herbicidal 3-(substituted benzoxazol-7-yl) and 3-(Substituted
  申请人：FMC Corporation

  公开号：US05753595A1

  公开（公告）日：1998-05-19

  Herbicidal 3-(substituted benzoxazol-7-yl) and 3-(substituted benzothiazol-7-yl)-1 -substituted-6-trifluoromethyl-2,4-(1H,3H)pyrimidinediones, compositions containing them, and methods of using them to control undesired plant growth are disclosed, as are novel intermediates used in the preparation of these compounds. The herbicidal compounds of the present invention are defined by the following generic structure: ##STR1## in which R is selected from a variety of substituents, including halogen, alkyl, alkenyl, alkynyl, phenyl, phenylalkyl, alkylphenylalkyl, haloalkyl, hydroxy, alkoxy, hydroxyalkyl, halophenyl, halophenylalkyl, alkoxyphenyl, sulfhydryl, alkylthio, piperidinyl, alkylamino, alkoxyalkyl, phenoxy, amino, alkylsulfonylamino, phenylsulfonylamino, and carboxy; R.sup.1 is alkyl or amino; R.sup.2 is hydrogen or halogen; X is oxygen or sulfur; Y is hydrogen, halogen, alkoxy, cyano, or nitro, and; Z is halogen; where halogen is bromine, chlorine, fluorine, or iodine, and each alkyl, alkoxy, alkenyl, or alkynyl moiety has one to six carbon atoms.

  本发明揭示了除草剂3-(取代苯并噁唑-7-基)和3-(取代苯并噻唑-7-基)-1-取代-6-三氟甲基-2,4-(1H,3H)嘧啶二酮，包含它们的组合物，以及使用它们控制不受欢迎的植物生长的方法，还公开了用于制备这些化合物的新型中间体。本发明的除草剂化合物由以下通用结构定义： R是从各种取代基中选择的，包括卤素、烷基、烯基、炔基、苯基、苯基烷基、烷基苯基烷基、卤代烷基、羟基、烷氧基、羟基烷基、卤代苯基、卤代苯基烷基、烷氧基苯基、硫醇基、烷基硫基、哌啶基、烷基氨基、烷氧基烷基、苯氧基、氨基、烷基磺酰氨基、苯基磺酰氨基和羧基；R^1是烷基或氨基；R^2是氢或卤素；X是氧或硫；Y是氢、卤素、烷氧基、氰基或硝基；Z是卤素；其中卤素是溴、氯、氟或碘，每个烷基、烷氧基、烯基或炔基基团具有一至六个碳原子。
• Processes to prepare pyrimidinediones
  申请人：——

  公开号：US20020010334A1

  公开（公告）日：2002-01-24

  A process for the preparation of a compound of formula I 1 comprising the steps of forming an 1-unsubstituted pyrimidinedione by reacting under basic conditions either a carbamate or an isocyanate with an alkenoate and forming a compound of formula I by alkylating, aminating, haloalkylating, alkylnitrilating, arylating, allylating, alkylalkoxylating, alkylcarboxylating, or propargylating the 1-position of said unsubstituted pyrimidinedione by adding an adduct forming agent selected from the group consisting of alkylating, aminating, haloalkylating, alkylnitrilating, arylating, allylating, alkylalkoxylating, alkylcarboxylating, and propargylating agents; where the 1-unsubstituted pyrimidinedione, the carbamate, the isocyanate, the alkenoate, and substituents V, W, X, Y, Z, and R are described herein. The reactions as described herein are carried out in a single reaction vessel and often produce the pyrimidindione of formula I in near quantitative yields. It is emphasized that his abstract is provided to comply with the rules requiring an abstract that will allow a searcher or other reader to quickly ascertain the subject matter of the technical disclosure. It is submitted with the understanding that it will not be used to interpret or limit the scope or meaning of the claims (see 37 C.F.R. 1.72(b)).

  一种制备I1式化合物的方法，包括以下步骤：在碱性条件下通过将碳酸酯或异氰酸酯与烯酸酯反应形成1-未取代嘧啶二酮，然后通过烷基化、氨基化、卤代烷基化、烷基腈基化、芳基化、烯丙基化、烷基烷氧基化、烷基羧化或丙炔基化添加选择自烷基化、氨基化、卤代烷基化、烷基腈基化、芳基化、烯丙基化、烷基烷氧基化、烷基羧化和丙炔基化试剂的加合物形成I式化合物；其中，未取代嘧啶二酮、碳酸酯、异氰酸酯、烯酸酯和取代基V、W、X、Y、Z和R的定义详见说明书。所述反应在单一反应容器中进行，通常可以获得接近定量收率的I式嘧啶二酮。强调本摘要仅用于遵守规定，以便搜索者或读者快速确定技术披露的主题，不得用于解释或限制权利要求的范围或含义（见37 C.F.R. 1.72(b)）。
• Designing New Protoporphyrinogen Oxidase-Inhibitors Carrying Potential Side Chain Isosteres to Enhance Crop Safety and Spectrum of Activity
  作者：Neanne Alnafta、Roland Beffa、Guido Bojack、Birgit Bollenbach-Wahl、Nicola Z. Brant、Christine Dörnbrack、Nicole Dorn、Jörg Freigang、Elmar Gatzweiler、Rahel Getachew、Claudia Hartfiel、Ines Heinemann、Hendrik Helmke、Sabine Hohmann、Harald Jakobi、Gudrun Lange、Peter Lümmen、Lothar Willms、Jens Frackenpohl

  DOI：10.1021/acs.jafc.3c01420

  日期：2023.11.29

  active ingredients which is also the case for protoporphyrinogen oxidase (PPO) inhibitors, a class of highly effective herbicides in use for more than 50 years. Hence, it is essential to continuously discover and develop new herbicidal PPO inhibitors with enhanced intrinsic activity, an improved resistance profile, enhanced crop safety, favorable physicochemical properties, and a clean toxicological profile

  尽管应用小分子化合物仍然是迄今为止最有效的技术，但控制杂草的方法有多种，这给世界各地的农民带来了特殊的挑战。然而，植物可以进化出对活性成分的抗性，原卟啉原氧化酶 (PPO) 抑制剂也是如此，这是一类使用了 50 多年的高效除草剂。因此，有必要不断发现和开发具有增强的内在活性、改善的抗性、增强的作物安全性、良好的理化性质和干净的毒理学特征的新型除草PPO抑制剂。通过修改已知 PPO 抑制剂（如噻芬那西）的结构关键特征，受电子等排体和混合匹配概念的启发，结合基于野生型苋属晶体结构的建模研究，我们发现了新的有前途的先导结构，在体外和体内表现出强大的活性几种臭名昭著的双子叶和单子叶杂草正在出现抗药性（例如，苋属、瘤苋属、黑麦草属和看麦穗属）。虽然几种在硫代连接的侧链上携带异恶唑啉基序的苯基尿嘧啶对不同苋属植物表现出有希望的抗性破坏潜力，但引入硫代丙烯酰胺侧链对抗性禾本科杂草具有出色的功效。