1-(3-chloropyridin-2-yl)-3-(2,2,2-trifluoroethoxy)-1H-pyrazole-5-carbonyl chloride | 1233223-84-1

• 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: 1-(3-chloropyridin-2-yl)-3-(2,2,2-trifluoroethoxy)-1H-pyrazole-5-carbonyl chloride
• 英文别名: 2-(3-chloro-pyridin-2-yl)-5-(2,2,2-trifluoro-ethoxy)-2H-pyrazole-3-carbonyl chloride；2-(3-Chloropyridin-2-yl)-5-(2,2,2-trifluoroethoxy)pyrazole-3-carbonyl chloride；2-(3-chloropyridin-2-yl)-5-(2,2,2-trifluoroethoxy)pyrazole-3-carbonyl chloride
• CAS: 1233223-84-1
• 化学式: C₁₁H₆Cl₂F₃N₃O₂
• 分子量: 340.089
• InChiKey: LOGGBSPWOKBKKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(3-chloropyridin-2-yl)-3-(2,2,2-trifluoroethoxy)-1H-pyrazole-5-carbonyl chloride 在 polyethylene glycol-400 作用下， 以 乙腈 为溶剂， 反应 0.67h， 生成 N-[[4-chloro-2-methyl-6-(propan-2-ylcarbamoyl)phenyl]carbamothioyl]-2-(3-chloropyridin-2-yl)-5-(2,2,2-trifluoroethoxy)pyrazole-3-carboxamide
  参考文献：
  名称：

  Synthesis, Insecticidal Activities, and SAR Studies of Novel Pyridylpyrazole Acid Derivatives Based on Amide Bridge Modification of Anthranilic Diamide Insecticides

  摘要：

  Anthranilic diamides are one of the most important classes of modern agricultural insecticides. To discover new structure-modified compounds with high activity, series of novel carbonyl thioureas, carbonyl ureas, oxadiazoles, carbonyl thiophosphorylureas, oxadiazole-containing amides, and thiazoline-containing amides were designed through the modification of the amide bridge based on the structure of chlorantraniliprole and were synthesized, and bioassays were carried out. The compounds were characterized and confirmed by melting point, IR, H-1 NMR, and elemental analyses or HRMS. Preliminary bioassays indicated that some compounds exhibited significant insecticidal activities against oriental armyworm, diamondback moth, beet armyworm, corn borer, and mosquito. Among them, trifluoroethoxyl-containing carbonyl thiourea 20a showed best larvicidal activity against oriental armyworm, with LC50 and LC95 values of 0.1812 and 0.7767 mg/L, respectively. Meanwhile, 20c and 20e showed 86 and 57% death rates against diamondback moth at 0.005 mg/L, and the LC50 values of the two compounds were 0.0017 and 0.0023 mg/L, respectively, which were lower than that of the control chlorantraniliprole. The relationship between structure and insecticidal activity was discussed, and the HF calculation results indicated that the carbonyl thiourea moiety plays an important role in the insecticidal activity. The present work demonstrated that the trifluoroethoxyl-containing carbonyl thioureas can be used as lead compounds for further development of novel insecticides.

  DOI：

  10.1021/jf4012467
• 作为产物：
  描述：

  2,3-二氯吡啶 在 dipotassium peroxodisulfate 、 草酰氯 、 硫酸 、 一水合肼 、 溶剂黄146 、 lithium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 1-(3-chloropyridin-2-yl)-3-(2,2,2-trifluoroethoxy)-1H-pyrazole-5-carbonyl chloride
  参考文献：
  名称：

  新型氟化苯胺邻氨基苯甲酸二酰胺提高了针对瑞安定受体的杀虫活性

  摘要：

  二酰胺类杀虫剂通过激活兰尼碱受体 (RyRs)对鳞翅目昆虫表现出非凡的活性。在本研究中，设计、合成了一系列含有氟苯胺部分的邻氨基苯甲酸二酰胺，并对其杀虫效力进行了评估。大多数标题化合物对Mythimna separata、Plutella xylostella和Spodoptera frugiperda具有中等至非常高的活性。化合物II l和II ac在 0.1 mg L -1时对M. separata的杀虫活性分别为26.7% 和 26.7% ，相当于氯虫苯甲酰胺（0.1 mg L -1, 30.0%)。与 LC 50 s相比，化合物II l、II y和II z分别比氯虫苯甲酰胺对小菜蛾的效力高 8.0 倍、1.8 倍和 4.7 倍。化合物II k和II aa对S. frugiperda表现出良好的杀虫活性，LC 50分别为 0.56 和 0.46 mg L -1，与商业杀虫剂氯虫苯甲酰胺的

  DOI：

  10.1021/acs.jafc.2c03134

文献信息

• Design, Synthesis and Biological Activities of Novel Anthranilic Diamide Insecticide Containing Trifluoroethyl Ether
  作者：Yu Zhao、Yongqiang Li、Lixia Xiong、Hongxue Wang、Zhengming Li

  DOI：10.1002/cjoc.201200362

  日期：2012.8

  anthranilic diamide insecticide containing trifluoroethyl ether were designed and synthesized, and their structures were characterized by 1H NMR spectroscopy, elemental analysis and single crystal X‐ray diffraction analysis. The insecticidal activities of the new compounds were evaluated. The results of bioassays indicated that some of these title compounds exhibited excellent insecticidal activities. The

  设计并合成了两类新型的含有三氟乙基醚的邻氨基苯甲酰胺类杀虫剂，并通过1 H NMR，元素分析和X射线单晶衍射分析对其结构进行了表征。评价了新化合物的杀虫活性。生物测定的结果表明，这些标题化合物中的一些表现出优异的杀虫活性。化合物19a，19b，19d，19g，19k和19m在2.5 mg·kg -1时对东方粘虫的杀虫活性为100％。19a，19b的幼虫活动反对小菜蛾的，，19c，19d，19e，19g和19n在0.1 mg·kg -1时为100％。令人惊讶的是，当浓度降低到0.05 mg·kg -1时，它们中的大多数仍然对小菜蛾表现出完美的杀虫活性，高于商业化的氯吡虫啉。
• Method of controlling particular insect pests by applying anthranilamide compounds
  申请人：E I DU PONT DE NEMOURS AND COMPANY

  公开号：US09113630B2

  公开（公告）日：2015-08-25

  This invention pertains to a method for controlling lepidopteran, homopteran, hemipteran, thysanopteran and coleopteran insect pests comprising contacting the insects or their environment with an arthropodicidally effective amount of a compound of Formula I, its N-oxide or an agriculturally suitable salt thereof wherein A and B and R1 through R8 are as defined in the disclosure. This invention further relates to a benzoxazinone compound of Formula 10 wherein R4 through R8 are as defined in the disclosure, useful for preparation of a compound of Formula I.

  这项发明涉及一种控制鳞翅目、同翅目、半翅目、鳞翅目和鞘翅目昆虫害虫的方法，包括将昆虫或其环境与化合物I的有效量，其N-氧化物或农业适用的盐接触，其中A和B以及R1至R8如披露中定义。该发明还涉及化合物10的苯并噁唑酮化合物，其中R4至R8如披露中定义，用于制备化合物I。
• Anthranilamide arthropodicide treatment
  申请人：E I DU PONT DE NEMOURS AND COMPANY

  公开号：US09173400B2

  公开（公告）日：2015-11-03

  This invention pertains to methods for protecting a propagule or a plant grown therefrom from invertebrate pests comprising contacting the propagule or the locus of the propagule with a biologically effective amount of a compound of Formula I, its N-oxide or an agriculturally suitable salt thereof wherein A and B and R1 through R8 are as defined in the disclosure. This invention also relates to propagules treated with a compound of Formula I and compositions comprising a Formula I compound for coating propagules.

  这项发明涉及一种保护繁殖体或从中生长的植物免受无脊椎动物害虫侵害的方法，包括将繁殖体或繁殖体的位置与化合物I的生物有效量，其N-氧化物或农业适用盐之一接触，其中A和B以及R1至R8如披露中所定义。该发明还涉及用化合物I处理过的繁殖体和包含化合物I的配方用于包覆繁殖体。
• NOVEL INSECTICIDES
  申请人：Muehlebach Michel

  公开号：US20100168066A1

  公开（公告）日：2010-07-01

  Compounds of formula (I) wherein the substituents are as defined in claim ( 1 ), and the agrochemically acceptable salts and all stereoisomers and tautomeric forms of the compounds of formula (I) can be used as agrochemical active ingredients and can be prepared in a manner known per se.

  化合物的化学式为(I)，其中取代基的定义如权利要求书(1)所述，化合物的所有立体异构体和互变异构体的农药学可接受的盐可以用作农药活性成分，并且可以采用已知的方法制备。
• Anthranilamide derivatives and their use for the control of insects and acari
  申请人：Syngenta Participations AG

  公开号：EP2213167A1

  公开（公告）日：2010-08-04

  Compounds of formula I wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts and all stereoisomers and tautomeric forms of the compounds of formula I can be used as agrochemical active ingredients against insects and acari and can be prepared in a manner known per se.

  式 I 的化合物 其中取代基如权利要求 1 所定义，式 I 化合物的农用化学品可接受盐、所有立体异构体和同分异构体可用作防治昆虫和螨类的农用化学品活性成分，并可按本身已知的方式制备。