964-42-1Relevant academic research and scientific papers
New synthetic access to 3-fluoroalkyl-5-pyrazolecarboxylates and carboxylic acids
Herrera, Alberto Gómez,Schmitt, Etienne,Panossian, Armen,Vors, Jean-Pierre,Pazenok, Sergii,Leroux, Frédéric R.
, p. 17 - 23 (2018/08/10)
A novel process for preparing 3-fluoroalkyl-5-pyrazolecarboxylates and carboxylic acids is hereby presented. Easily accesible α-fluorinated ketimines were condensed with oxalyl monochloride derivatives, and the obtained vinamides underwent acid-catalyzed cyclization with substituted hydrazines. This highly efficient protocol can also be used for non-fluorinated C-3 and C-5 substituents.
New analogues of (E)-β-farnesene with insecticidal activity and binding affinity to aphid odorant-binding proteins
Sun, Yufeng,Qiao, Huili,Ling, Yun,Yang, Shaoxiang,Rui, Changhui,Pelosi, Paolo,Yang, Xinling
, p. 2456 - 2461 (2011/10/12)
(E)-β-Farnesene is a strong and efficient alarm pheromone in most aphid species. However, applications in agriculture are prevented by its relatively high volatility, its susceptibility to oxidation and its complex and expensive synthesis. To develop novel compounds for aphid control, we have designed and synthesized analogues of (E)-β-farnesene, containing a pyrazole moiety present in several insecticides. Their structures have been confirmed by 1H NMR, elemental analysis, high-resolution mass spectroscopy and IR. Binding activities to three odorant-binding proteins (OBPs) of the pea aphid Acythosiphon pisum have been evaluated and correlated with their structures with reference to (E)-β-farnesene. Several derivatives were shown both to bind to A. pisum OBPs with a specificity similar to that of (E)-β-farnesene and to have aphicidal activity comparable to that of thiacloprid, a commercial insecticide. The compounds synthesized in this work represent new potential agents for aphid population control and provide guidelines to design analogues of (E)-β-farnesene endowed with both insecticidal and repellent activity for aphids.
(13)C Chemical Shifts and (1)H - (13)C Coupling Constants of N-Phenyl-, N-p-Fluorophenyl- and N-o-Nitrophenylpyrazoles
Begtrup, Mikael,Vedso, Per,Cabildo, Pilar,Claramunt, Rosa Maria,Elguero, Jose,Meutermans, Wim
, p. 455 - 459 (2007/10/02)
The (13)C chemical shifts and some (1)H - (13)C coupling constants of twelve N-arylpyrazoles are reported.The assignments were made by using the effects of a fluorine substituent and two-dimensional techniques. Key words: (13)C chemical shifts, (1)H - (13
1,3-Dipolar Cycloadditions, 89. New Contributions to the Chemistry of Diphenylnitrilimine
Clovis, James S.,Fliege, Werner,Huisgen, Rolf
, p. 3062 - 3070 (2007/10/02)
Methyl propiolate, tetrolate, and phenylpropiolate combine with diphenylnitrilimine (1) to afford regioisomeric cycloadducts; the preferential orientation shifts in the sequence given from the pyrazole-5-carboxylic ester to the 4-carboxylic ester.Correspo
4,5-Dihydroisoxazoles. Part 5. Addition Reactions of Diazoalkanes. Nitrile Imines and Nitrile Oxides to 3-Aryl-4-methylene-5-morpholino-4,5-dihydroisoxazoles
Ballabio, Marzia,Croce, Piero Dalla,Massari, Valeria,Pocar, Donato,Riva, Alberto,Trimarco, Pasqualina
, p. 1317 - 1340 (2007/10/02)
Some 5-morpholino-3-aryl-4-methylene-4,5-dihydroisoxazoles were reacted with nitrile oxides, diazoalkanes and nitrile imines.The corresponding cycloaddition products, namely spiro and spirobi derivatives, were obtained
1,3-Dipolar Cycloadditions, 90. Diphenylnitrilimine and Substituted Butadienes; Substituent Effects and Rate of Cycloaddition
Fliege, Werner,Huisgen, Rolf,Kolbeck, Winfried,Weberndoerfer, Volkmar
, p. 3438 - 3460 (2007/10/02)
1-Substitued butadienes accept diphenylnitrilimine (2) not at the 1,2- but rather at the 3,4-double bond; the regiospecific cycloaddition furnishes 5-substituted 1,3-diphenyl-2-pyrazolines.The relative addition rates, measured in competition experiments,
