1-[(6-chloropyridin-3-yl)methyl]-1-nitroguanidine | 131748-56-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-[(6-chloropyridin-3-yl)methyl]-1-nitroguanidine
• 英文别名: N-(6-chloropyridin-3-ylmethyl)-N'-nitroguanidine；1-(6-chloro-3-pyridyl)methyl-2-nitroguanidine
• CAS: 131748-56-6
• 化学式: C₇H₈ClN₅O₂
• 分子量: 229.62
• InChiKey: GHBBFPGYBPOUCF-UHFFFAOYSA-N

物化性质

• 沸点：
  393.1±52.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-硝基-S-甲基异硫脲 、 5-氨基甲基-2-氯吡啶 以 乙醇 为溶剂， 反应 3.0h， 以84%的产率得到1-[(6-chloropyridin-3-yl)methyl]-1-nitroguanidine
  参考文献：
  名称：

  The discovery of thiamethoxam: a second-generation neonicotinoid

  摘要：

  Neonicotinoids represent a novel and distinct chemical class of insecticides with remarkable chemical and biological properties. In 1985, a research programme was started in this field, in which novel nitroimino heterocycles were designed, prepared and assayed for insecticidal activity. The methodology for the synthesis of 2-nitroimino-hexahydro-1,3,5-triazines, 4-nitroimino-1,3,5-oxadiazinanes and 4-nitroimino-1,3,5-thiadiazinanes is outlined. Bioassays demonstrated that 3-(6-chloropyridin-3-ylmethyl)-4-nitroimino-1,3,5-oxadiazinane exhibited better insecticidal activity than the corresponding 2-nitroimino-hexahydro-1,3,5-triazine and 4-nitroimino-1,3,5-thiadiazinane. In most tests, this compound was equally or only slightly less active than imidacloprid. A series of structural modifications on this lead structure revealed that replacement of the 6-chloro-3-pyridyl group by a 2-chloro-5-thiazolyl moiety resulted in a strong increase of activity against chewing insects, whereas the introduction of a methyl group as pharmacophore substituent increased activity against sucking pests. The combination of these two favourable modifications led to thiamethoxam (CGA 293 343).Thiamethoxam is the first commercially available second-generation neonicotinoid and belongs to the thianicotinyi sub-class. It is marketed under the trademarks Actara(R) for foliar and soil treatment and Cruiser(R) for seed treatment. The compound has broad-spectrum insecticidal activity and offers excellent control of a wide variety of commercially important pests in many crops. Low use rates, flexible application methods, excellent efficacy and the favourable safety profile make this new insecticide well-suited for modern integrated pest management programmes in many cropping systems. (C) 2001 Society of Chemical Industry.

  DOI：

  10.1002/1526-4998(200102)57:2<165::aid-ps289>3.0.co;2-g

文献信息

• Divergent Synthesis of Substituted Amino-1,2,4-triazole Derivatives
  作者：Jia-Qi Li、Zhaohai Qin、Fenghai Zhao、Thishana Singh、Yumei Xiao、Wangcang Su、Dongyan Yang、Changqing Jia

  DOI：10.1055/a-1477-4630

  日期：2021.6

  A divergent efficient assembly of disubstituted 1,2,4-triazoles was established by cyclization of readily accessible N′-nitro-2-hydrocarbylidene-hydrazinecarboximidamides with moderate to excellent yields under mild reaction conditions. This divergent synthetic strategy was achieved simply by varying the reaction conditions. Under acidic conditions, amino-1,2,4-triazoles were obtained by an intramolecular

  通过在温和的反应条件下以中等至极好的收率将易于获得的N'-硝基-2-亚烃基-肼甲二酰亚胺环化，可以建立二取代的1,2,4-三唑的不同有效组装。仅通过改变反应条件就可以实现这种多样化的合成策略。在酸性条件下，通过涉及NO 2基团的分子内氧化还原反应获得氨基-1,2,4-三唑。对照实验和DFT研究表明，这种转化过程是通过分子内的1,3-氢化物转移途径进行的，从而消除了HNO2。在中性条件下，以水为溶剂，通过在空气中氧化分子内环化获得硝基亚氨基-1，2，4-三唑。
• Substituted aza(cyclo)alkanes
  申请人：Bayer Aktiengesellschaft

  公开号：US05461069A1

  公开（公告）日：1995-10-24

  Insecticidally active substituted aza(cyclo)alkanes of the formula (I) ##STR1## in which R.sup.1 represents a five- or six-membered heterocyclic grouping which contains 1, 2, 3 or 4 nitrogen atoms and/or one or two oxygen atoms or sulphur atoms as the heteroatom ring members--the number of heteroatoms being 1, 2, 3 or 4--and which is optionally substituted R.sup.2 represents hydroxyalkyl, polyhydroxyalkyl, alkoxyalkyl or polyalkoxyalkyl, R.sup.3 represents hydrogen, alkyl, hydroxyalkyl, dihydroxyalkyl, alkoxyalkyl or dialkoxyalkyl, R.sup.4 represents hydrogen or any of various organic radicals, Y represents nitrogen or a CH group and Z represents cyano or nitro. Also intermediates therefor and process of making.

  式(I)的杀虫活性取代的aza(cyclo)烷烃，其中R.sup.1代表一个含有1、2、3或4个氮原子和/或一个或两个氧原子或硫原子作为杂原子环成员的五元或六元杂环基团--杂原子的数量为1、2、3或4--并且可以取代R.sup.2代表羟基烷基、多羟基烷基、烷氧基烷基或多烷氧基烷基，R.sup.3代表氢、烷基、羟基烷基、二羟基烷基、烷氧基烷基或二烷氧基烷基，R.sup.4代表氢或各种有机基，Y代表氮或CH基团，Z代表氰基或硝基。还包括其中间体和制备方法。
• Synthesis and Properties of Thiamethoxam and Related Compounds
  作者：Peter Maienfisch

  DOI：10.1515/znb-2006-0401

  日期：2006.4.1

  The neonicotinoids are the most successful chemical class of insecticides reaching sales of more than $1 billion in 2003, mainly due to the excellent market performance of imidacloprid and thiamethoxam. This paper describes the discovery, the synthesis and the insecticidal activity of thiamethoxam and related compounds and reports the hydrolytic stability and the degradation pathways of thiamethoxam together with the synthesis of the degradation products

  新烟碱类杀虫剂是最成功的化学类杀虫剂之一，其销售额在2003年达到了10亿美元以上，主要是由于咪唑烟碱和噻虫嗪的市场表现优异。本文描述了噻虫嗪及其相关化合物的发现、合成和杀虫活性，并报告了噻虫嗪的水解稳定性和降解途径，以及降解产物的合成。
• Hexahydrotriazine compounds and insecticides
  申请人：Agro-Kanesho Co., Ltd.

  公开号：US06187773B1

  公开（公告）日：2001-02-13

  A hexahydrotrazine compound which is 1-(2-chloro-5-pyridylmethyl)-3,5-dimethyl-2-nitroiminohexahydro-1,3,5-triazine or 1-(2-chloro-5-thiazolylmethyl)-3,5-dimethyl-2-nitroiminiohexahydro-1,3,5-triazine and insecticides containing the same.

  这是一种六氢三嗪类化合物，其化学式为1-(2-氯-5-吡啶甲基)-3,5-二甲基-2-硝基亚氨基六氢-1,3,5-三嗪，或1-(2-氯-5-噻唑甲基)-3,5-二甲基-2-硝基亚氨基六氢-1,3,5-三嗪，可用于制备杀虫剂。
• Nitroguanidine compounds and insecticides
  申请人：AGRO-KANESHO CO., LTD.

  公开号：EP0425978A2

  公开（公告）日：1991-05-08

  Insecticides which are improved over the conventional insectides are provided by the use of a nitroguanidine compound represented by the following general formula (I): wherein R stands for hydrogen or methyl; R¹ and R² are the same or different, and stand for hydrogen or methyl; and X stands for a group indicated by or The insecticides provided by this invention are extremely active for controlling various harmful insects and yet are low in toxicity to warm-blooded animals, fishes and Crustacea, the remaining quantity thereof after their use is small, and they do not produce phytotoxicity in various plants.

  通过使用由以下通式（I）表示的硝基胍化合物，提供了比传统杀虫剂更好的杀虫剂： 其中 R 代表氢或甲基；R¹ 和 R² 可以相同或不同，并代表氢或甲基；X 代表由以下表示的基团 或 本发明提供的杀虫剂对控制各种有害昆虫具有极高的活性，但对温血动物、鱼类和甲壳动物的毒性低，使用后的剩余量小，对各种植物不产生植物毒性。