3-ethyl-4-nitroimino-1,3,5-oxadiazinane

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-ethyl-4-nitroimino-1,3,5-oxadiazinane
• 英文别名: N-(3-ethyl-1,3,5-oxadiazinan-4-ylidene)nitramide
• 化学式: C₅H₁₀N₄O₃
• 分子量: 174.159
• InChiKey: CELFWRGHEKMCHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  82.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E)-3-(4-氯苯基)丙烯酰氯 、 3-ethyl-4-nitroimino-1,3,5-oxadiazinane 在 吡啶 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以22.4%的产率得到N-{3-[(E)-3-(4-chlorophenyl)acryloyl]-5-ethyl-1,3,5-oxadiazinan-4-ylidene}nitramide
  参考文献：
  名称：

  Design, Synthesis, and Insecticidal Activity of 1,5-Diphenyl-1-pentanone Analogues

  摘要：

  AbstractThree series of novel 1,5‐diphenyl‐1‐pentanone derivatives were designed and synthesized. Their structures were characterized by IR, 1H NMR techniques, and elemental analysis. The insecticidal activities of the new compounds were preliminarily evaluated. The bioassay results indicated that the compounds X11–X30 displayed better aphicidal activity against Aphis gossypii than compounds X1–X10 and the lead compound (E)‐1,5‐diphenyl‐1‐penten‐1‐one (A). The inhibitory rates of compounds X6 and X29 were 100% against Plutella xylostella (L.) at 600 mg·L−1. Compounds X12, X13, X19, X24, X25, X26 and X27 showed higher insecticidal activity against Tetranychus cinnabarinus (Boisduval) at 600 mg·L−1 than the lead compound (A).

  DOI：

  10.1002/cjoc.201180409
• 作为产物：
  描述：

  聚合甲醛 、 甲酸 、 2-乙基-1-硝基胍 以 水 为溶剂， 以87%的产率得到3-ethyl-4-nitroimino-1,3,5-oxadiazinane
  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