2,4,5-trichloro-6-(2-chloro-6-fluoro-4-nitrophenylamino)isophthalonitrile | 1416419-89-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,4,5-trichloro-6-(2-chloro-6-fluoro-4-nitrophenylamino)isophthalonitrile
• 英文别名: 2,4,5-Trichloro-6-(2-chloro-6-fluoro-4-nitroanilino)benzene-1,3-dicarbonitrile；2,4,5-trichloro-6-(2-chloro-6-fluoro-4-nitroanilino)benzene-1,3-dicarbonitrile
• CAS: 1416419-89-0
• 化学式: C₁₄H₃Cl₄FN₄O₂
• 分子量: 420.014
• InChiKey: QCTLDCOUNYSHNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 硫酸 、 硝酸 作用下， 反应 1.33h， 以63%的产率得到2,4,5-trichloro-6-(2-chloro-6-fluoro-4-nitrophenylamino)isophthalonitrile
  参考文献：
  名称：

  Synthesis and fungicidal activity of fluorine-containing chlorothalonil derivatives

  摘要：

  Fourteen new fluorine-containing chlorothalonil derivatives were synthesized by using intermediate derivatization method (IDM) in order to discover novel antifungal compounds for controlling corn rust. The structures of synthesized compounds were confirmed by H-1 NMR, C-13 NMR, F-19 NMR, elemental analysis, HRMS and X-ray. The bioassay results indicated that compound 2,4,5-trichloro-6-(2,6-dichloro-4-[trifluoromethyl]phenylamino)isophthalonitrile (3j, R-n is 2,6-Cl2-4-CF3) had the optimal structure with best fungicidal activity against corn rust (98%, 70% controls) at 25 and 6.25 mg/L concentration, respectively, much better than chlorothalonil and fluazinam, highlighting the importance of trifluoromethyl group on 4-position of benzene ring. The structure-activity relationship of the synthesized compounds was discussed as well. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.01.006

文献信息

• SUBSTITUTED CYANOANILINE COMPOUNDS, PREPARATION AND USE THEREOF
  申请人：Liu Changling

  公开号：US20140213598A1

  公开（公告）日：2014-07-31

  Disclosed is a substituted cyanoaniline compound or a salt thereof, wherein the compound has a structure represented by General Formula I. The compound of General Formula I has broad-spectrum fungicidal activity in the field of agriculture and effectively prevents against a variety of pathogens such as cucumber downy mildew, wheat powdery mildew, maize rust disease, rice blast and cucumber gray mold. In particular, even at a low dose, the compound effectively prevents and treats rice blast, cucumber gray mold, maize rust disease and cucumber downy mildew. Moreover, the raw materials for preparing the compounds are widely available and the synthesis method therefor is simple and convenient.

  揭示了一种取代的氰基苯胺化合物或其盐，其中该化合物具有由一般式I表示的结构。一般式I的化合物在农业领域具有广谱杀菌活性，并有效预防多种病原体，如黄瓜霜霉病、小麦白粉病、玉米锈病、稻瘟病和黄瓜灰霉病。特别是，即使在低剂量下，该化合物也能有效预防和治疗稻瘟病、黄瓜灰霉病、玉米锈病和黄瓜霜霉病。此外，用于制备这些化合物的原材料广泛可得，其合成方法简单方便。
• Design, Synthesis, and Structure–Activity Relationship of Novel Aniline Derivatives of Chlorothalonil
  作者：Ai-Ying Guan、Chang-Ling Liu、Guang Huang、Hui-Chao Li、Shu-Lin Hao、Ying Xu、Zhi-Nian Li

  DOI：10.1021/jf403739e

  日期：2013.12.11

  chlorine groups in the phenyl ring in phenyl amine with other functional groups. These functional groups with various electronic properties and spatial characteristics were considered to explore the relationship between structure and fungicidal activity. The results indicate that the electron-withdrawing group NO2 on the 4 position on the right phenyl ring plays a unique role on enhancing the fungicidal

  具有低成本和低毒性的氯噻酮是在农业化学领域中广泛使用的杀真菌剂。该化合物上亲核基团的存在允许进一步的化学修饰以获得新的百菌清衍生物。另一种具有广谱杀真菌谱的可商购药物Fluazinam具有二芳基胺结构的支架。为了模拟该主链结构，使用多种（未）取代的苯胺作为亲核试剂与百菌清进行反应，从而获得具有二苯胺结构的化合物。通过优雅的设计，形成了两个引线2,4,5-三氯-6-（2,4-二氯苯基氨基）间苯二甲腈（7）和2,4,5-三氯-6-（2,4,6-三氯苯基氨基）间苯二甲腈（11），经过初步的生物测定筛选后发现具有潜在的杀真菌活性。通过将苯胺中苯环中的氯基团替换为其他官能团，进一步修饰了这两种铅，以获得最终产物。这些具有各种电子特性和空间特征的官能团被认为是探索结构与杀真菌活性之间的关系。结果表明，吸电子基团NO 2在右苯环的4位上的化合物在增强杀真菌活性方面起着独特的作用。通过质子核磁共振和元素分
• US8937072B2
  申请人：——

  公开号：US8937072B2

  公开（公告）日：2015-01-20
• Synthesis and fungicidal activity of fluorine-containing chlorothalonil derivatives
  作者：Aiying Guan、Changling Liu、Guang Huang、Huichao Li、Shulin Hao、Ying Xu、Yong Xie、Zhinian Li

  DOI：10.1016/j.jfluchem.2014.01.006

  日期：2014.4

  Fourteen new fluorine-containing chlorothalonil derivatives were synthesized by using intermediate derivatization method (IDM) in order to discover novel antifungal compounds for controlling corn rust. The structures of synthesized compounds were confirmed by H-1 NMR, C-13 NMR, F-19 NMR, elemental analysis, HRMS and X-ray. The bioassay results indicated that compound 2,4,5-trichloro-6-(2,6-dichloro-4-[trifluoromethyl]phenylamino)isophthalonitrile (3j, R-n is 2,6-Cl2-4-CF3) had the optimal structure with best fungicidal activity against corn rust (98%, 70% controls) at 25 and 6.25 mg/L concentration, respectively, much better than chlorothalonil and fluazinam, highlighting the importance of trifluoromethyl group on 4-position of benzene ring. The structure-activity relationship of the synthesized compounds was discussed as well. (C) 2014 Elsevier B.V. All rights reserved.