2-甲基-1-苯基-2-(1,2,4-三唑-1-基)丙烷-1-酮 | 94154-45-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-甲基-1-苯基-2-(1,2,4-三唑-1-基)丙烷-1-酮
• 英文名称: Phenyl-triazolyl-metyrapone
• 英文别名: α-(1,2,4-triazol-1-yl)-isobutyrophenone；1H-Quinoline-4-carboxylic acid, 6-methoxy-2-oxo-, ethyl ester；2-methyl-1-phenyl-2-(1,2,4-triazol-1-yl)propan-1-one
• CAS: 94154-45-7
• 化学式: C₁₂H₁₃N₃O
• mdl: MFCD00170408
• 分子量: 215.255
• InChiKey: BHEFYJRYJYFQDH-UHFFFAOYSA-N

物化性质

• 沸点：
  383.4±44.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲基-1-苯基-2-(1,2,4-三唑-1-基)丙烷-1-酮 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 (R,S)-2-Methyl-1-phenyl-2-(1,2,4-triazol-1-yl)propan-1-ol
  参考文献：
  名称：

  Effects of anti-ecdysteroid azole analogues of metyrapone on the larval development of the fleshfly,Neobellieria bullata

  摘要：

  AbstractBased on our previous finding that PIM (phenyl‐imidazolyl‐metyra‐pon; 2‐(1‐imidazolyl)‐2‐methyl‐1‐phenylpropan‐1‐one, 1) is a strong inhibitor of ecdysone 20‐monooxygenase (IC50 = 7.89 × 10−7 M) from the fleshfly, Neobellieria bullata (Parker) and has also a good toxic action in vivo against this insect, 17 imidazole and 1,2,4‐triazole analogues of metyrapone were synthesized and evaluated for their action against N. bullata larvae in terms of toxicity, length of larval development, weight of the puparium as well as special symptoms, i.e. malformations of the anterior and posterior spiracles, and of the mandibles. The introduction of p‐methoxy (LC50 = 49 mg kg−1 in diet) or p‐chloro (LC50 = 97 mg kg−1) substituents on the benzene ring of PIM resulted in a significant increase in toxicity compared to that of metyrapone (LC50 = 561 mg kg−1) and PIM (LC50 = 148 mg kg−1). The hybridization state of the carbon atom adjacent to the benzene ring was not an important factor for toxicity because the acetoxy derivative (13) was almost as toxic as PIM. At least one methyl group was required on the carbon atom adjacent to the azole ring to maintain activity, while an ethyl group (4) enhanced the toxic effect. At the applied doses some compounds including metyrapone itself, extended the duration of the larval development. Only metyrapone and PIM decreased the puparium weight. Several derivatives induced lethal malformations of mandibles as well as the anterior and posterior spiracles.

  DOI：

  10.1002/ps.2780440304
• 作为产物：
  描述：

  1H-1,2,4-三唑 生成 2-甲基-1-苯基-2-(1,2,4-三唑-1-基)丙烷-1-酮
  参考文献：
  名称：

  ELBE, H. -L.;REGEL, E.;BUECHEL, K. -H.;SCHALLER, K.;PLEMPEL, M.

  摘要：

  DOI：

文献信息

• 3-(1,2,4-triazol-1-yl)-prop-1-ene fungicides
  申请人：Bayer Aktiengesellschaft

  公开号：US04740515A1

  公开（公告）日：1988-04-26

  3-(1,2,4-Triazol-1-yl)-prop-1-enes of the general formula (I) ##STR1## in which X.sup.1 and X.sup.2 independently of one another represent hydrogen or methyl, R.sup.1 represents alkyl, alkenyl, in each case optionally substituted cycloalkyl or cycloalkenyl or in each case optionally substituted phenyl or benzyl and R.sup.2 represents alkyl, alkenyl, in each case optionally substituted cycloalkyl or cycloalkenyl, halogenoalkyl, in each case optionally substituted phenyl or phenylalkyl, phenoxyalkyl or phenylthioalkyl, in each case optionally substituted in the phenyl part, but wherein R.sup.1 and R.sup.2 may not simultaneously represent optionally substituted phenyl if X.sup.1 and/or X.sup.2 represent hydrogen, and acid addition salts and metal salt complexes thereof which are tolerated by plants, exhibit fungicidal activity.

  通式(I)中，3-(1,2,4-三唑-1-基)-丙烯酸酯化合物，其中X.sup.1和X.sup.2分别独立地表示氢或甲基，R.sup.1表示烷基，烯基，可选择取代的环烷基或环烯基，或可选择取代的苯基或苄基，而R.sup.2表示烷基，烯基，可选择取代的环烷基或环烯基，卤代烷基，可选择取代的苯基或苯基烷基，苯氧基烷基或苯硫基烷基，其中苯基部分可选择取代，但如果X.sup.1和/或X.sup.2表示氢，则R.sup.1和R.sup.2不能同时表示可选择取代的苯基。该化合物及其酸加成盐和金属盐配合物能被植物耐受，具有杀真菌活性。
• 3-(1,2,4-Triazol-1-yl)-1-propene
  申请人：BAYER AG

  公开号：EP0132730A1

  公开（公告）日：1985-02-13

  Die Erfindung betrifft neue 3-(1,2,4-Triazol -1-yl)-1- propene, mehrere Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide. Die Verbindungen der allgemeinen Formel in welcher R', R', X' und X2 die in der Beschreibung angegebene Bedeutung besitzen, werden erhalten, wenn man z.B. 3-Halogen- bzw. 3-Sulfonyl-oxy-1-propene mit 1, 2, 4-Triazol in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säurebinders umsetzt. Daneben gibt es noch andere Verfahren. Die Wirkstoffe sind für den Gebrauch als Pflanzenschutzmittel geeignet und mit besonders gutem Erfolg zur Bekämpfung von Getreidekrankheiten sowie zur Bekämpfung von Obst- und Gemüsekrankheiten eingesetzt werden.

  本发明涉及新型 3-(1,2,4-三唑-1-基)-1-丙烯、其制备的几种工艺及其作为杀菌剂的用途。 通式如下的化合物 其中 R'、R'、X'和 X2 具有说明中给出的含义、 例如，3-卤代或 3-磺酰氧基-1-丙烯与 1，2，4-三唑在稀释剂和酸粘合剂的作用下发生反应。还有其他方法。 这些活性成分适合用作植物保护产品，尤其在防治谷物病害和果蔬病害方面效果显著。
• ELBE, H. -L.;REGEL, E.;BUECHEL, K. -H.;SCHALLER, K.;PLEMPEL, M.
  作者：ELBE, H. -L.、REGEL, E.、BUECHEL, K. -H.、SCHALLER, K.、PLEMPEL, M.

  DOI：——

  日期：——
• US4740515A
  申请人：——

  公开号：US4740515A

  公开（公告）日：1988-04-26
• Effects of anti-ecdysteroid azole analogues of metyrapone on the larval development of the fleshfly,<i>Neobellieria bullata</i>
  作者：Iván Bélai、Béla Darvas、Krisztina Bauer、Mahmoud H. Tag El-Din

  DOI：10.1002/ps.2780440304

  日期：1995.7

  AbstractBased on our previous finding that PIM (phenyl‐imidazolyl‐metyra‐pon; 2‐(1‐imidazolyl)‐2‐methyl‐1‐phenylpropan‐1‐one, 1) is a strong inhibitor of ecdysone 20‐monooxygenase (IC50 = 7.89 × 10−7 M) from the fleshfly, Neobellieria bullata (Parker) and has also a good toxic action in vivo against this insect, 17 imidazole and 1,2,4‐triazole analogues of metyrapone were synthesized and evaluated for their action against N. bullata larvae in terms of toxicity, length of larval development, weight of the puparium as well as special symptoms, i.e. malformations of the anterior and posterior spiracles, and of the mandibles. The introduction of p‐methoxy (LC50 = 49 mg kg−1 in diet) or p‐chloro (LC50 = 97 mg kg−1) substituents on the benzene ring of PIM resulted in a significant increase in toxicity compared to that of metyrapone (LC50 = 561 mg kg−1) and PIM (LC50 = 148 mg kg−1). The hybridization state of the carbon atom adjacent to the benzene ring was not an important factor for toxicity because the acetoxy derivative (13) was almost as toxic as PIM. At least one methyl group was required on the carbon atom adjacent to the azole ring to maintain activity, while an ethyl group (4) enhanced the toxic effect. At the applied doses some compounds including metyrapone itself, extended the duration of the larval development. Only metyrapone and PIM decreased the puparium weight. Several derivatives induced lethal malformations of mandibles as well as the anterior and posterior spiracles.