Design, Synthesis and Insecticidal Activities of Novel Pirazol Derivatives to Crop Protection

Capítulo de Libro

Autoría

MACHUCA, LAURA MARCELA ; MURGUIA, MARCELO CESAR

Fecha

2020

Editorial y Lugar de Edición

SCIENCEDOMAIN International

Libro

Emerging Trends in Engineering Research and Technology (pp. 95-107)
SCIENCEDOMAIN International

ISBN

978-93-90206-36-0

Resumen Información suministrada por el agente en SIGEVA

Aryl pyrazoles are compounds that display very interesting biological activities. This chapter reviews recent work of our group in the development of synthetic strategies for the preparation of new examples of these kinds of compounds to crop protection. A series of six N-aryl pyrazoles was synthesized by Michael-type addition reaction. The molecules 5-amino-1-aryl-1H-pyrazole-4-carbonitrile (3a-f) were synthesized from (ethoxymethylene)malononitrile (1) and fluorinated and non-fluorinated aryl... Aryl pyrazoles are compounds that display very interesting biological activities. This chapter reviews recent work of our group in the development of synthetic strategies for the preparation of new examples of these kinds of compounds to crop protection. A series of six N-aryl pyrazoles was synthesized by Michael-type addition reaction. The molecules 5-amino-1-aryl-1H-pyrazole-4-carbonitrile (3a-f) were synthesized from (ethoxymethylene)malononitrile (1) and fluorinated and non-fluorinated aryl hydrazines (2a-f) using ethanol and fluorinated ethanol as solvents at reflux. An excellent regio-selectivity was found when pyrazole de- rivatives were formed as an exclusive product. No other regioisomer or uncyclised hydrazide was observed. Their structures were confirmed by spectroscopy data (1H, 13C, 19F, COSY (correlation spectroscopy), HSQC (heteronuclear single-quantum correlation spectroscopy) and HMBC (heteronuclear multiple-bond correlation spectroscopy); MS (mass-spectrometry). The yields ranged from good to excellent (47% - 93%) under mild reaction conditions. It would indicate a high selectivity in the one-step work procedure. These products (3a-f) and derivatives have a potential academic and industrial use as key intermediates, in special for application in crop protection.

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Palabras Clave

N-ARYL PIRAZOLE5-AMINO-1-ARYL-1H-PYRAZOLE-4-CARBONITRILESTUTA ABSOLUTAARYL HYDRAZINE

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http://hdl.handle.net/11336/137537