methyl 3-(4-chlorophenyl)-1-[N-(4-chlorophenyl)carbamoyl]-4-methyl-2-pyrazoline-4-carboxylate | 99823-74-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-(4-chlorophenyl)-1-[N-(4-chlorophenyl)carbamoyl]-4-methyl-2-pyrazoline-4-carboxylate
• 英文别名: Methyl (4RS)-3-(4-chlorophenyl)-1-[N-(4-chlorophenyl)carbamoyl]-4-methyl-2-pyrazoline-4-carboxylate；Methyl (4RS)-3-(4-chlorophenyl)-4-methyl-1-[N-(4-chlorophenyl)carbamoyl]-2-pyrazoline-4-carboxylate；N,3-bis(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide；1H-Pyrazole-4-carboxylic acid, 3-(4-chlorophenyl)-1-(((4-chlorophenyl)amino)carbonyl)-4,5-dihydro-4-methyl-, methyl ester；methyl 5-(4-chlorophenyl)-2-[(4-chlorophenyl)carbamoyl]-4-methyl-3H-pyrazole-4-carboxylate
• CAS: 99823-74-2
• 化学式: C₁₉H₁₇Cl₂N₃O₃
• 分子量: 406.268
• InChiKey: DYGFZLXVZHSAOZ-UHFFFAOYSA-N

物化性质

• 熔点：
  125.5-126.5 °C
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  71
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-(4-chlorophenyl)-1-[N-(4-chlorophenyl)carbamoyl]-4-methyl-2-pyrazoline-4-carboxylate 在 吡啶 、 sodium hydroxide 、 氯化亚砜 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 10.5h， 生成 (1S)Methylbenzyl (4S)-3-(4-chlorophenyl)-1-[N-(4-chlorophenyl)carbamoyl]-4-methyl-2-pyrazoline-4-carboxylate
  参考文献：
  名称：

  Stereochemical basis for the insecticidal activity of carbamoylated and acylated pyrazolines

  摘要：

  Methyl 3-(4-chlorophenyl)-1-[N-(4-chlorophenyl)carbamoyl] -4-methyl-2-pyrazoline-4-carboxylate was converted to corresponding (1R)- and (1S)-phenethyl esters via its carboxylic acid and acid chloride at the C-4 atom to separate the diastereomers. Their configurations were confirmed by X-ray analysis. Both isomers of the (1R)methylbenzyl ester were subjected to transesterification with sodium methoxide to obtain enantiomers of the starting methyl ester. Their insecticidal activity was measured against American cockroaches (Periplaneta americana (L.)) by injection and against house flies (Musca domestica L.) by topical application under various synergistic conditions with metabolic inhibitors. The activity values of the four alpha-methylbenzyl esters and the R-isomer of the starting methyl ester were similar. The S-enantiomer of the methyl ester was about 10 and 100 times more active than the R-isomer against the cockroach and the fly, respectively. Some N-arylacetyl and N-aryloxyacetyl derivatives of the starting N-(4-chlorophenyl)carbamoyl compound gave very low activity. Conformation-energy profiles for some compounds suggested that the conformation of substituents on the N-1 atom in the pyrazoline ring has a specific role for the potential insecticidal effects.

  DOI：

  10.1002/(sici)1096-9063(199602)46:2<105::aid-ps320>3.0.co;2-y
• 作为产物：
  描述：

  4-氯苯丙酮 在 吡啶 、 sodium acetate 、 苄基三甲基氢氧化铵 、 sodium hydride 、 一水合肼 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 12.0h， 生成 methyl 3-(4-chlorophenyl)-1-[N-(4-chlorophenyl)carbamoyl]-4-methyl-2-pyrazoline-4-carboxylate
  参考文献：
  名称：

  Quantitative structure-activity relationships of insecticidal pyrazolines

  摘要：

  AbstractMethyl 3‐(4‐chlorophenyl)‐4‐methyl‐1‐[N‐(4‐substituted pheny1)carba‐moy1]‐2‐pyrazoline‐4‐carboxylates and related compounds were prepared. Their convulsant activity was determined as the minimum dose required to bring about the symptom within 1 h after injection against male adult American cockroaches, Periplaneta americana (L.). Insecticidal activity with metabolic inhibitors for oxidation and hydrolysis was measured 24 h after injection of the test compounds. Variations in each of the activities were analysed by using physicochemical substituent parameters and regression analysis. The findings indicated that the greater the hydrophobicity and the more the electron‐withdrawing property of the substituents, the higher were the activities. Variations in each of the two activities were parabolically related to the STERIMOL width parameter with an optimum value of about zero.

  DOI：

  10.1002/ps.2780420406

文献信息

• Insecticidal n-aryl-3-aryl-4,5-dihydro-1h-pyrazole-1-carboxamides
  申请人：Rohm and Haas Company

  公开号：US04663341A1

  公开（公告）日：1987-05-05

  This invention relates to N-aryl-3-aryl-4,5-dihydro-1H-pyrazole-1-carboxamide compounds which are useful as pesticides, compositions containing those compounds, methods of controlling pests and processes for preparing these compounds.

  这项发明涉及N-芳基-3-芳基-4,5-二氢-1H-吡唑烷-1-甲酰胺化合物，可用作杀虫剂，包含这些化合物的组合物，控制害虫的方法以及制备这些化合物的过程。
• N-aryl-3-aryl-4,5-dihydro-1H-pyrazole-1-carboxamides and methods of
  申请人：Rohm and Haas

  公开号：US04863947A1

  公开（公告）日：1989-09-05

  This invention relates to novel N-aryl-3-aryl-4,5-dihydro-1H-pyrazole-1-carboxamide compounds which are useful as pesticides, compositions containing those compounds, methods of controlling pests and processes for preparing these compounds.

  本发明涉及新颖的N-芳基-3-芳基-4,5-二氢-1H-吡唑-1-甲酰胺化合物，这些化合物作为农药具有实用性，包含这些化合物的组合物，控制害虫的方法以及制备这些化合物的工艺。
• N-aryl-3-aryl-4,5-dihydro-1H-pyrazole-1-carboxamides, processes for their production, insecticidal compositions containing them and methods for combatting insects
  申请人：ROHM AND HAAS COMPANY

  公开号：EP0153127B1

  公开（公告）日：1991-04-03
• Effects of alkyl groups attached to the carbamoyl nitrogen atom of an<i>N</i>-arylcarbamoylpyrazoline on insecticidal activity
  作者：Keiichiro Nishimura、Toshiji Tada、Ryo Shimizu、Akira Ohoka

  DOI：10.1002/(sici)1096-9063(199904)55:4<446::aid-ps928>3.0.co;2-v

  日期：1999.4
• US4663341A
  申请人：——

  公开号：US4663341A

  公开（公告）日：1987-05-05