4,6-二甲氧基-2-(苯氧基羰基)氨基嘧啶 | 89392-03-0

• 物质功能分类: 医药中间体 - 嘧啶类化合物
• 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: 4,6-二甲氧基-2-(苯氧基羰基)氨基嘧啶
• 中文别名: (4,6-二甲氧基-2-嘧啶基)氨基甲酸苯酯；2-[(苯氧基羰基)氨基]-4,6-二甲氧基嘧啶；4,6-二甲氧基-2-[(苯氧基羰基)氨基]嘧啶；4,6-二甲氧基-2-嘧啶氨基甲酸苯酯；4,6-二甲氧基-2-(苯氧羰基氨基)嘧啶；2-((苯氧基羰基)胺基)-4,6-二甲氧基嘧啶
• 英文名称: O-phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate
• 英文别名: phenyl 4,6-dimethoxypyrimidin-2-yl carbamate；Phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate
• CAS: 89392-03-0
• 化学式: C₁₃H₁₃N₃O₄
• 分子量: 275.264
• InChiKey: MESPVSMSORHLAX-UHFFFAOYSA-N

物化性质

• 熔点：
  118.0 to 122.0 °C
• 沸点：
  250℃[at 101 325 Pa]
• 密度：
  1.317±0.06 g/cm3(Predicted)
• LogP：
  2.1 at 25℃
• 物理描述：
  DryPowder

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  82.6
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险等级：
  9
• 危险品标志：
  Xi
• 安全说明：
  S24,S37
• 危险类别码：
  R51/53,R43
• 海关编码：
  2933599090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4,6-Dimethoxy-2-(phenoxycarbonyl)aminopyrimidine
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 4,6-Dimethoxy-2-(phenoxycarbonyl)aminopyrimidine
CAS number: 89392-03-0

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C13H13N3O4
Molecular weight: 275.3

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途：用于有机合成中间体。

反应信息

• 作为反应物：
  描述：

  4,6-二甲氧基-2-(苯氧基羰基)氨基嘧啶 在 lithium hydroxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(α-hydroxyethyl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis and herbicidal activity of new benzenesulfonylureas

  摘要：

  DOI：

  10.1002/(sici)1096-9063(199905)55:5<576::aid-ps953>3.0.co;2-t
• 作为产物：
  描述：

  2-氨基-4,6-二甲氧基嘧啶 、 氯甲酸苯酯 在 N,N-二甲基苯胺 作用下， 以 1,4-二氧六环 为溶剂， 以86.2%的产率得到4,6-二甲氧基-2-(苯氧基羰基)氨基嘧啶
  参考文献：
  名称：

  5-取代磺酰脲类作为靶向乙酰羟酸合酶的新型抗真菌剂的设计、合成和生物学评价

  摘要：

  乙酰羟酸合酶（AHAS；EC2.2.1.6）仅存在于植物和微生物中，当磺酰脲类与AHAS催化亚基活性位点结合时，支链氨基酸（缬氨酸、亮氨酸和异亮氨酸）的生物合成受阻，导致无法进行合成这些蛋白质并最终导致植物和微生物的死亡。因此，AHAS 也是一个很有前途的抗真菌靶点。如今，迫切需要发现新的潜在靶点和化学结构，以防止真菌感染的发病率和死亡率不断增加，以及出现严重的抗真菌药物耐药性。在这项工作中，设计和合成了 36 种目标化合物，其中几种 5-取代磺酰脲类药物具有比氟康唑​​ (FCZ) 和两性霉素 B (AMB) 更好的抗真菌活性。L10、L23和L31对白色念珠菌AHAS 和 MICs 的抑制常数 ( K i ) 在 5.6∼9.6 nM 范围内（MIC 被确定为相对于相应药物抑制真菌生长 > 90% 的药物浓度- 无生长控制）<0.05∼0.78 µg/mL白色念珠菌SC 5314、17#

  DOI：

  10.1016/j.molstruc.2022.132756

文献信息

• 一种四唑嘧磺隆关键中间体的制备方法及其 应用
  申请人：江西安利达化工有限公司

  公开号：CN105384725B

  公开（公告）日：2018-06-22

  本发明提供一种1‑甲基‑4‑(2‑甲基‑2H‑四氮唑‑5‑基)‑1H‑吡唑‑5‑磺酰胺的制备方法，包括以下步骤：以原甲酸三甲酯和丙二腈为起始原料，经过三步反应得到1‑甲基‑5‑氨基‑4‑(四氮唑‑5‑基)吡唑；然后在缚酸剂存在下，与硫酸二甲酯反应，得到2‑甲基‑5‑(1‑甲基‑5‑氨基‑1H‑吡唑‑4‑基)‑2H‑四氮唑；在酸性条件下，经亚硝酸钠重氮化，再与亚硫酸钠‑氯化铜‑乙酸混合物反应；最后经氨水解，得到目标产物。本发明还提供一种包括所述1‑甲基‑4‑(2‑甲基‑2H‑四氮唑‑5‑基)‑1H‑吡唑‑5‑磺酰胺的制备的四唑嘧磺隆的制备方法。本发明的制备方法反应路线短、反应原料环保、产率高。
• [EN] PROCESS OF PREPARATION OF AZIMSULFURON<br/>[FR] PROCÉDÉ DE PRÉPARATION D'AZIMSULFURON
  申请人：RALLIS INDIA LTD

  公开号：WO2014002111A1

  公开（公告）日：2014-01-03

  The present disclosure provides process for preparation of azimsulfuron or its salts, isomers, and other derivatives thereof. The process involves treating a compound of formula I, (Formula I should be inserted here.) with aqueous acetic acid or formic acid and chlorine gas or sodium hypochlorite in presence of hydrochloric acid in chlorinated solvents such as dichloromethane, 1,2-dichloroethane or with aqueous acetic acid and N-chlorosuccinimide or hydrogen peroxide in presence of hydrochloric acid in aqueous cyclic ether such as tetrahydrofuran, 1,4-dioxane to obtain 1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonyl chloride; converting the sulfonyl chloride to a sulfonamide and treating the sulfonamide with a phenyl(4,6-dimethoxypyrimidin-2-yl) carbamate to obtain azimsulfuron or its salts, isomers, and other derivatives thereof.

  本公开提供了制备阿吉磺隆或其盐、异构体和其他衍生物的方法。该方法涉及使用具有化学式I的化合物（应在此处插入化学式I）与水杨酸或甲酸和氯气或次氯酸钠在氯化溶剂（如二氯甲烷、1,2-二氯乙烷）中，在氯化溶剂中的氯化氢的存在下处理，或者与水杨酸和N-氯琥珀酰亚胺或过氧化氢在环氧乙醚（如四氢呋喃、1,4-二噁烷）中的氯化氢的存在下处理，以获得1-甲基-4-(2-甲基-2H-四唑-5-基)-1H-吡唑-5-磺酰氯；将磺酰氯转化为磺酰胺，并将磺酰胺与苯基(4,6-二甲氧基嘧啶-2-基)氨基甲酸酯处理，以获得阿吉磺隆或其盐、异构体和其他衍生物。
• PROCESS OF PREPARATION OF AZIMSULFURON
  申请人：Rallis India Limited

  公开号：US20150112063A1

  公开（公告）日：2015-04-23

  The present disclosure provides process for preparation of azimsulfuron or its salts, isomers, and other derivatives thereof. The process involves treating a compound of formula I, with aqueous acetic acid or formic acid and chlorine gas or sodium hypochlorite in presence of hydrochloric acid in chlorinated solvents such as dichloromethane, 1,2-dichloroethane or with aqueous acetic acid and N-chlorosuccinimide or hydrogen peroxide in presence of hydrochloric acid in aqueous cyclic ether such as tetrahydrofuran, 1,4-dioxane to obtain 1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonyl chloride; converting the sulfonyl chloride to a sulfonamide and treating the sulfonamide with a phenyl(4,6-dimethoxypyrimidin-2-yl) carbamate to obtain azimsulfuron or its salts, isomers, and other derivatives thereof.

  本公开提供了制备阿吉磺隆或其盐、异构体和其他衍生物的方法。该方法涉及使用具有式I的化合物， 在氯代溶剂（如二氯甲烷、1,2-二氯乙烷）中，通过在水杨酸或甲酸和氯气或次氯酸钠的存在下，用盐酸处理；或者在水环醚（如四氢呋喃、1,4-二噁烷）中，通过在水杨酸和N-氯琥珀酰亚胺或过氧化氢的存在下，用盐酸处理，以获得1-甲基-4-(2-甲基-2H-四唑-5-基)-1H-吡唑-5-磺酰氯；将磺酰氯转化为磺酰胺，并将磺酰胺与苯基(4,6-二甲氧基嘧啶-2-基)氨基甲酸酯处理，以获得阿吉磺隆或其盐、异构体和其他衍生物。
• Discovery of <i>ortho-</i>Alkoxy Substituted Novel Sulfonylurea Compounds That Display Strong Herbicidal Activity against Monocotyledon Grasses
  作者：Hai-Lian Wang、Hao-Ran Li、Yi-Chi Zhang、Wen-Tao Yang、Zheng Yao、Ren-Jun Wu、Cong-Wei Niu、Yong-Hong Li、Jian-Guo Wang

  DOI：10.1021/acs.jafc.1c02081

  日期：2021.8.4

  have designed and synthesized a series of 42 novel sulfonylurea compounds with ortho-alkoxy substitutions at the phenyl ring and evaluated their herbicidal activities. Some target compounds showed excellent herbicidal activity against monocotyledon weed species. When applied at 7.5 g ha–1, 6–11 exhibited more potent herbicidal activity against barnyard grass (Echinochloa crus-galli) and crab grass (Digitaria

  在本研究中，我们设计并合成了一系列 42 种在苯环上具有邻烷氧基取代的新型磺酰脲类化合物，并评估了它们的除草活性。一些目标化合物对单子叶杂草种类显示出优异的除草活性。当以 7.5 g ha –1、6–11施用时，对稗草 ( EChinochloa crus-galli ) 和马唐草 ( Digitaria sanguinalis ) 的除草活性比商业乙酰羟酸合酶 (AHAS；EC 2.2.1.6) 抑制剂三嘧磺隆、五氟磺草胺、芽前和芽后条件下的烟嘧磺隆。6–11以这种超低剂量对花生进行芽后施用是安全的，这表明它可以被认为是花生田的潜在除草剂候选物。尽管6-11和三嘧磺隆具有相似的化学结构并且对植物 AHAS 的K i值接近，但从 DFT 计算中观察到它们的 LUMO 图之间存在显着差异，这可能是导致它们对单子叶杂草种类不同行为的一个可能因素.
• [EN] AGRICULTURAL CHEMICALS<br/>[FR] PRODUITS CHIMIQUES AGRICOLES
  申请人：REDX PHARMA LTD

  公开号：WO2013136073A1

  公开（公告）日：2013-09-19

  The present invention relates to derivatives of compounds which are known to be of use in the field of agriculture. These derivatives are differentiated from the parent active compound by virtue of being redox derivatives of the active compound. This means that one or more of the functional groups in the active compound has been converted to another group in one or more changes one or more of which may be considered to represent a change of oxidation state relative to the groups in the original compound. We refer to these compounds generally as redox derivatives. The compounds are of use as insecticides, herbicides and insect repellents.

  本发明涉及与已知在农业领域中有用的化合物衍生物。这些衍生物通过成为活性化合物的氧化还原衍生物而与母体活性化合物区分开来。这意味着活性化合物中的一个或多个官能团已被转化为另一个官能团，其中一个或多个变化可能被认为代表相对于原始化合物中的官能团的氧化状态的变化。我们通称这些化合物为氧化还原衍生物。这些化合物可用作杀虫剂、除草剂和驱虫剂。