Synthèse de biocides potentiels destinés à l'agrochimie principalement en série nitrée

Abstract : In this work, we have developed a new route to beta-nitroenones substitued at the beta-position by an hydrogen atom starting from alpha, beta-unsaturated ketones. The reactivity of these compounds towards nucleophiles was studied. Titanium enolates add to carbonyl finction, their corresponding ethylene acetals reacted with isocyanoacetates and tosylmethyl isocyanide affording respectively 3-alkanoylpyrrole-2-carboxylates, 7-oxo-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylates and 3-alkanoyl-4-nitropyrroles. the second part of of this work was devoted to the synthesis of cyclic beta-nitroenones based on the regioselective ring opening of nitroepoxides. Nucleophiles (bis activated compounds enolates, thiolates, alkoxides) added regioselectively on the nitroalkene function alpha to the carbonyl group. Finally, in the third part, we have investigated the preparation of analogs of Imidacloprid, an insecticide used in agriculture. Different families of compounds were envisaged : Potential insecticides as nitroimines, nitroiminoimidazolidines and nitroalkenes were synthetized.
Document type :
Theses
File URL :
http://docnum.univ-lorraine.fr/prive/SCD_T_1997_0177_BOELLE.pdf
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https://hal.univ-lorraine.fr/tel-01747432
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Submitted on : Thursday, March 29, 2018 - 10:59:50 AM
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  • HAL Id : tel-01747432, version 1

Citation

Jérôme Boëlle. Synthèse de biocides potentiels destinés à l'agrochimie principalement en série nitrée. Autre. Université Henri Poincaré - Nancy 1, 1997. Français. ⟨NNT : 1997NAN10177⟩. ⟨tel-01747432⟩

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