2-isobutylidene-N'-nitrohydrazinecarboximidamide | 330816-81-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-isobutylidene-N'-nitrohydrazinecarboximidamide
• 英文别名: 2-isobutylidene-N'-nitrohydrozinecarboximidamide；1-(2-methylpropylideneamino)-2-nitroguanidine
• CAS: 330816-81-4
• 化学式: C₅H₁₁N₅O₂
• 分子量: 173.175
• InChiKey: PXOAHXIQTUIUST-UHFFFAOYSA-N

物化性质

• 沸点：
  259.9±23.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-isobutylidene-N'-nitrohydrazinecarboximidamide 在 硫酸 、 sodium hydride 、 对甲苯磺酸 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 N'-(1-([2-chlorothiazol-5-yl]methyl)-3-isopropyl-1H-1,2,4-triazol-5-yl)-N-(cyanomethyl)-N-methylformimidamide
  参考文献：
  名称：

  新型含脒基1,2,4-三唑的合成及杀虫活性

  摘要：

  在分子杂交的指导下，设计合成了一系列含有新烟碱和脒片段的化合物。对小菜蛾和棉蚜的生物活性进行了评价。这些化合物中的大多数在 500 μg/ml 的浓度下对棉蚜表现出良好的活性。构效关系分析表明1,2,4-三唑骨架上烷基的长度和大小对杀虫活性有显着影响。

  DOI：

  10.1002/jhet.4500
• 作为产物：
  描述：

  异丁醛 、 1-氨基-3-硝基胍 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 2-isobutylidene-N'-nitrohydrazinecarboximidamide
  参考文献：
  名称：

  新型含脒基1,2,4-三唑的合成及杀虫活性

  摘要：

  在分子杂交的指导下，设计合成了一系列含有新烟碱和脒片段的化合物。对小菜蛾和棉蚜的生物活性进行了评价。这些化合物中的大多数在 500 μg/ml 的浓度下对棉蚜表现出良好的活性。构效关系分析表明1,2,4-三唑骨架上烷基的长度和大小对杀虫活性有显着影响。

  DOI：

  10.1002/jhet.4500

文献信息

• Synthesis and insecticidal activity of novel 1,2,4-triazole derivatives containing trifluoroacetyl moieties
  作者：Fenghai Zhao、Xianjun Tang、Min Liu、Zhaohai Qin、Jia-Qi Li、Yumei Xiao

  DOI：10.1007/s11030-021-10321-4

  日期：2022.8

  were synthesized, and their insecticidal activity against Nilaparvata lugens and Aphis craccivora was evaluated. The compound structure was identified by NMR, HRMS, and single-crystal diffraction. The bioassay results indicated that compound 4-1 (R1 is chloropyridine, R2 is H), 4-2 (R1 is chlorothiazole, R2 is H) and 4-19 (R1 is benzyl, R2 is isopropyl) had the best activity against Nilaparvata lugens

  合成了一系列含有三氟乙酰基的化合物，并对其对褐飞虱和Aphis craccivora的杀虫活性进行了评价。通过NMR、HRMS和单晶衍射鉴定了化合物的结构。生物测定结果表明化合物4-1（R 1为氯吡啶，R 2为H）、4-2（R 1为氯噻唑，R 2为H）和4-19（R 1为苄基，R 2为异丙基）在 100 mg/L 浓度下对褐飞虱的活性最高（93.5%、94.1% 和 95.5%）。R 1或R 2不同取代基的影响通过构效关系研究活性。讨论了化合物 4-1 和 4-2 的分子对接。 图形摘要
• 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。
• HYDROCARBYLIDENE NITROHYDROZINECARBOXIMIDAMIDES AND A METHOD FOR MAKING THE SAME, AS WELL AS THEIR USES AS AN INSECTICIDE
  申请人：Qin ZhaoHai

  公开号：US20110306639A1

  公开（公告）日：2011-12-15

  The present invention discloses hydrocarbylidene nitrohydrozinecarboximidamides and the use thereof as well as a method for making the same. The structural general formula of the compounds are shown in formula I, wherein, R1 is C1-C10 saturated and/or unsaturated aliphatic hydrocarbonyl, benzyl, substituted benzyl, halogenated picolyl, halogenated thiazolyl methyl, tetrahydrofuryl methyl or oxazolyl methyl; R2 is hydrogen, C1-C5 saturated and/or unsaturated aliphatic hydrocarbonyl, phenyl, substituted phenyl, pyridyl or substituted pyridyl; R3 is hydrogen, C1-C10 saturated and/or unsaturated aliphatic hydrocarbonyl, furyl, phenyl, substituted phenyl, benzyl or substituted benzyl. The tests of insecticidal activity show that the hydrocarbylidene nitrohydrozinecarboximidamides shown by formula (I) have high preventive efficiency against insect pests of plants, such as aphid, plant hopper, cotton bollworm, asparagus caterpillar, and the like, and can be used as plant insecticides.

  本发明公开了羟基甲烷基亚硝基羟肼羧酰胺及其用途，以及制备该化合物的方法。所述化合物的结构通式如式I所示，其中，R1为C1-C10饱和和/或不饱和脂肪烃基、苄基、取代苄基、卤代吡啶基、卤代噻唑基甲基、四氢呋喃基甲基或噁唑基甲基；R2为氢、C1-C5饱和和/或不饱和脂肪烃基、苯基、取代苯基、吡啶基或取代吡啶基；R3为氢、C1-C10饱和和/或不饱和脂肪烃基、呋喃基、苯基、取代苯基、苄基或取代苄基。杀虫活性测试显示，式(I)所示的羟基甲烷基亚硝基羟肼羧酰胺对植物害虫（如蚜虫、植食性跳蚤、棉铃虫、天冬毛虫等）具有很高的预防效果，并可用作植物杀虫剂。
• Condensed amino nitroguanidine compounds, synthesis and use as botanical insecticides thereof
  申请人：Qin, ZhaoHai

  公开号：EP2216324B1

  公开（公告）日：2013-03-13
• <i>N</i>′-Nitro-2-hydrocarbylidenehydrazinecarboximidamides: Design, Synthesis, Crystal Structure, Insecticidal Activity, and Structure–Activity Relationships
  作者：Wangcang Su、Yihui Zhou、Yongqiang Ma、Lei Wang、Zheng Zhang、Changhui Rui、Hongxia Duan、Zhaohai Qin

  DOI：10.1021/jf300616x

  日期：2012.5.23

  A novel series of acyclic imine-substituted nitenpyram analogues were designed and synthesized from nitroaminoguanidine, and their structures were confirmed using X-ray diffraction crystallography. Preliminary bioassays showed that the target molecules exhibited good activities against aphids in laboratory (Myzus persicae Sulzer) and field trials (M. persicae Sulzer and Brevicoryne brassicae Linnaeus). Comparative molecular field analysis and comparative molecular similarity indices analysis were employed to develop a three-dimensional quantitative structure activity relationship model that describes the insecticidal activity of 21 neonicotinoid derivatives. Simple synthesis, low cost, and good insecticidal activity have made this series of compounds become very promising candidates for future commercial pesticides.