N-(2-chlorothiazol-5-ylmethyl)-N'-nitroguanidine | 135018-15-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(2-chlorothiazol-5-ylmethyl)-N'-nitroguanidine
• 英文别名: 1-[(2-Chloro-1,3-thiazol-5-yl)methyl]-2-nitroguanidine；1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-nitroguanidine
• CAS: 135018-15-4
• 化学式: C₅H₆ClN₅O₂S
• 分子量: 235.654
• InChiKey: ZTLCLYBKONTDBT-UHFFFAOYSA-N

物化性质

• 熔点：
  166-168 °C
• 沸点：
  412.5±55.0 °C(Predicted)
• 密度：
  1.88±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  137
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-chlorothiazol-5-ylmethyl)-N'-nitroguanidine 在 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 噻虫嗪
  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
• 作为产物：
  描述：

  噻虫胺 在 P₄₅₀ cytochrome b5 、 recombinant CYP₃A_4.1 from human 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 aq. phosphate buffer 为溶剂， 生成 N-(2-chlorothiazol-5-ylmethyl)-N'-nitroguanidine
  参考文献：
  名称：

  10.1016/j.cbi.2024.111154

  摘要：

  DOI：

  10.1016/j.cbi.2024.111154

文献信息

• 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。
• Nitroguanidine compounds useful as insecticides
  申请人：Agro-Kanesho Co., Ltd.

  公开号：US05166164A1

  公开（公告）日：1992-11-24

  Insecticides which are improved over the conventional insectides are provided by the use of a nitroguanidine compound represented by the following general formula (I): ##STR1## wherein R stands for hyydrogen or methyl; R.sup.1 and R.sup.2 are the same or different, and stand for hydrogen or methyl; and X stands for a group indicated by ##STR2## 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.

  使用以下一般式（I）所代表的硝基胍化合物，改进了传统杀虫剂，从而提供了更好的杀虫剂： ##STR1## 其中，R代表氢或甲基；R.sup.1和R.sup.2相同或不同，代表氢或甲基；X代表由以下组所示的组：##STR2## 本发明提供的杀虫剂对于控制各种有害昆虫非常活跃，对于温血动物、鱼类和甲壳类动物毒性低，使用后剩余量小，不会对各种植物产生植物毒性。
• 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。
• A novel method for the preparation of N,N′-disubstituted-N′′-nitroguanidines, including a practical synthesis of the neonicotinoid insecticide clothianidin
  作者：Peter Maienfisch、Hanspeter Huerlimann、Joerg Haettenschwiler

  DOI：10.1016/s0040-4039(00)01225-9

  日期：2000.9

  A novel method is described for the synthesis of N,N'-disubstituted-N"-nitroguanidines 3 via 2-nitroiminohexahydro-1,3,5-triazine intermediates 12, allowing the introduction of the heteroarylmethyl group either from a heteroarylmethyl amine 9 or a heteroarylmethyl chloride 14, respectively. This method enables an efficient synthesis of the neonicotinoid insecticide clothianidin (3b) in four steps from S-methyl-N-nitroisothiourea (10). (C) 2000 Elsevier Science Ltd. All rights reserved.
• Aerobic versus Anaerobic Microbial Degradation of Clothianidin under Simulated California Rice Field Conditions
  作者：Rebecca A. Mulligan、Patrick L. Tomco、Megan W. Howard、Tabitha T. Schempp、Davis J. Stewart、Phillip M. Stacey、David B. Ball、Ronald S. Tjeerdema

  DOI：10.1021/acs.jafc.6b02055

  日期：2016.9.28

  Microbial degradation of clothianidin was characterized under aerobic and anaerobic California rice field conditions. Rate constants (k) and half-lives (DT50) were determined for aerobic and anaerobic microcosms, and an enrichment experiment was performed at various nutrient conditions and pesticide :concentrations. Temperatilre effects on anaerobic degradation rates were determined at 22 +/- 2 and 35 +/- 2 degrees C. Microbial growth was assessed in the presence of various pesticide concentrations, and distinct colonies were isolated and identified. Slow aerobic degradation was observed, but anaerobic degradation occurred rapidly at both 25 and 35 degrees C. Transformation rates and DT50 values in flooded soil at 35 +/- 2 degrees C (k = -7.16- X 10(-2) +/- 3.08 x 10(-3) day(-1), DT50 = 9.7 days) were significantly faster than in 25 +/- 2 degrees C microcosms (k=-2.45 X 10(-2) +/- 1.59 X 10(-3) day(-1), DT50 = 28.3 days). At the field scale, biodegradation of clothianidin will' Vary with :extent of:oxygenation.: