N-[(2-氯-5-硝基-苯基)亚甲基]羟胺 | 89692-57-9

• 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: N-[(2-氯-5-硝基-苯基)亚甲基]羟胺
• 英文名称: 2-chloro-5-nitro-benzaldehyde oxime
• 英文别名: 2-chloro-5-nitro-benzaldehyde-oxime；2-Chlor-5-nitro-benzaldehyd-oxim；2-Chlor-5-nitro-benzaldoxim；N-[(2-chloro-5-nitrophenyl)methylidene]hydroxylamine
• CAS: 89692-57-9
• 化学式: C₇H₅ClN₂O₃
• mdl: MFCD00160761
• 分子量: 200.581
• InChiKey: BCVYAFHZIZEYLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  N-[(2-氯-5-硝基-苯基)亚甲基]羟胺 在 N-氯代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2-Chlor-5-nitro-benzhydroxamoylchlorid
  参考文献：
  名称：

  2-芳基喹啉的新途径：2'-硝基芳基-Δ2-异恶唑啉的还原裂解

  摘要：

  报道了一种在还原条件下以 Δ2-异恶唑啉为原料合成喹啉的新合成路线。在金属和无金属条件下均可实现还原环化为喹啉。该反应通过分子内 N-H···O 氢键中间体进行，与非氢键系统相比，还原裂解加速了 1000 倍（DFT 计算）。

  DOI：

  10.1055/s-0036-1588751
• 作为产物：
  描述：

  2-氯-5-硝基苯甲醛 在 盐酸羟胺 作用下， 以 乙醇 、 水 为溶剂， 生成 N-[(2-氯-5-硝基-苯基)亚甲基]羟胺
  参考文献：
  名称：

  Discovery of Novel N-Isoxazolinylphenyltriazinones as Promising Protoporphyrinogen IX Oxidase Inhibitors

  摘要：

  Protoporphyrinogen oxidase (PPO, EC 1.3.3.4) is a promising target for herbicide discovery. Search for new compounds with novel chemotypes is a key objective for agrochemists. Here, we describe the discovery and systematic SAR-based structure optimization of novel N-isoxazolinylphenyltriazinones 5-9 as PPO inhibitors. The in vivo herbicidal activity and in vitro Nicotiana tabacum PPO (NtPPO) inhibitory activity were explored in detail. A number of the new synthetic compounds displayed strong PPO inhibitory activity with K-i values in the nanomolar range. Some compounds exhibited excellent and broad-spectrum weed control at the rate of 9.375-37.5 g ai/ha by postemergence application and showed improved monocotyledonous weed control compared to saflufenacil. Most promisingly, ethyl 3-(2-chloro-5-(3,5-dimethyl--2,6-dioxo-4-thioxo-1,3,5-triazinan-1-yl)-4-fluorophenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylate, 5a, with a K-i value of 4.9 nM, displayed over 2- and 6-fold higher potency than saflufenacil (K-i = 10 nM) and trifludimoxazin (K-i = 31 nM), respectively. Moreover, 5a showed excellent and broad-spectrum weed control against 32 kinds of weeds at 37.5-75 g ai/ha. Rice exhibited relative tolerance to 5a at 150 g ai/ha by postemergence application, indicating that Sa could be a potential herbicide candidate for weed control in paddy fields.

  DOI：

  10.1021/acs.jafc.9b04844

文献信息

• Oxime ethers and pesticidal preparations containing them
  申请人：Ciba-Geigy AG

  公开号：US03941839A1

  公开（公告）日：1976-03-02

  New oxime ethers and pesticidal and herbicidal preparations containing them are disclosed. The oxime ethers correspond to the formula ##SPC1## Wherein R.sub.1 is a hydrogen atom or a lower alkyl radical; R.sub.2 is an aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radical; or wherein R.sub.1 and R.sub.2 form part of a saturated or unsaturated carbocycle or a 5-, 6- or 7-membered heterocycle; R.sub.3 is a nitro, trifluoromethyl, formyl, lower carbalkoxy, sulfamyl or mono- or di-lower alkyl sulfamyl radical; R.sub.4.sub.- and R.sub.5.sub.- each is a hydrogen or halogen atom, an amino, mono- or di-lower alkyl amino, lower alkoxy, cycloalkoxy, lower alkylthio, nitro, lower carbalkoxy, arylthio, lower aralkylthio or lower alkyl group, or 5-, 6- or 7-membered heterocycle.

  揭示了新的肟醚化合物和含有它们的杀虫剂和除草剂制剂。这些肟醚化合物对应于以下结构式：其中R1为氢原子或较低的烷基基团；R2为脂肪族、环脂肪族、芳基脂肪族、芳香族或杂环基团；或者R1和R2构成饱和或不饱和的碳环或5、6或7元杂环的一部分；R3为硝基、三氟甲基、甲酰基、较低的羰基烷氧基、磺胺基或单或双较低的烷基磺胺基基团；R4和R5分别为氢或卤素原子、氨基、单或双较低的烷基氨基、较低的烷氧基、环烷氧基、较低的烷基硫氧基、硝基、较低的羰基烷氧基、芳基硫氧基、较低的芳基烷基硫氧基或较低的烷基基团，或者为5、6或7元杂环。
• Meyer,V., Chemische Berichte, 1893, vol. 26, p. 1253
  作者：Meyer,V.

  DOI：——

  日期：——
• Kolesetskaya,G.I. et al., Journal of Organic Chemistry USSR (English Translation), 1970, vol. 6, p. 323 - 326
  作者：Kolesetskaya,G.I. et al.

  DOI：——

  日期：——
• 1120. Derivatives of 6-aminopenicillanic acid. Part VIII. Further analogues of 3-O-chorophenyl-5-methyl-4-isoxazolylpenicillin
  作者：J. C. Hanson、A. A. W. Long、J. H. C. Nayler、E. R. Stove

  DOI：10.1039/jr9650005976

  日期：——
• Discovery of Novel <i>N</i>-Isoxazolinylphenyltriazinones as Promising Protoporphyrinogen IX Oxidase Inhibitors
  作者：Da-Wei Wang、Rui-Bo Zhang、Shu-Yi Yu、Lu Liang、Ismail Ismail、Yong-Hong Li、Han Xu、Xin Wen、Zhen Xi

  DOI：10.1021/acs.jafc.9b04844

  日期：2019.11.13

  Protoporphyrinogen oxidase (PPO, EC 1.3.3.4) is a promising target for herbicide discovery. Search for new compounds with novel chemotypes is a key objective for agrochemists. Here, we describe the discovery and systematic SAR-based structure optimization of novel N-isoxazolinylphenyltriazinones 5-9 as PPO inhibitors. The in vivo herbicidal activity and in vitro Nicotiana tabacum PPO (NtPPO) inhibitory activity were explored in detail. A number of the new synthetic compounds displayed strong PPO inhibitory activity with K-i values in the nanomolar range. Some compounds exhibited excellent and broad-spectrum weed control at the rate of 9.375-37.5 g ai/ha by postemergence application and showed improved monocotyledonous weed control compared to saflufenacil. Most promisingly, ethyl 3-(2-chloro-5-(3,5-dimethyl--2,6-dioxo-4-thioxo-1,3,5-triazinan-1-yl)-4-fluorophenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylate, 5a, with a K-i value of 4.9 nM, displayed over 2- and 6-fold higher potency than saflufenacil (K-i = 10 nM) and trifludimoxazin (K-i = 31 nM), respectively. Moreover, 5a showed excellent and broad-spectrum weed control against 32 kinds of weeds at 37.5-75 g ai/ha. Rice exhibited relative tolerance to 5a at 150 g ai/ha by postemergence application, indicating that Sa could be a potential herbicide candidate for weed control in paddy fields.