Amino acid and glucose conjugates of a phenylpyrrole compound : synthesis, systemicity and biological properties

Abstract : The purpose of our work is to develop a vectorization strategy to confer phloem mobility to agrochemicals by applying prodrug concept into agrochemical design. Fenpiclonil, a non-systemic fungicide from the phenylpyrrole family, was selected as a model parent compound and modified by associating it with an amino acid or a monosaccharide.The phloem mobility of L and D-glutamic acid and D-glucose fenpiclonil conjugates (D-GFC) was evaluated in Ricinus seedlings. The systemicity test showed that the L-amino acid promoiety was clearly more favorable to phloem mobility than D-amino acid or D-glucose. The results suggested that the transport of the L-amino acid conjugate is governed by a stereospecific amino acid carrier system energized by the proton motive force. Further investigation indicated that D-GFC was a potent and selective inhibitor of sucrose uptake by leaf tissues and sucrose phloem loading. Due to its specific inhibition of sucrose transporters (e.g. AtSUC2), D-GFC can be a candidate as a new tool in phloemology. Finally, we explored structural modifications of the spacer arm to optimize the prodrug strategy. Different structures of the spacer arm were introduced between fenpiclonil and the amino acid function. The conjugate which contains a triazole ring with the shortest amino acid chain showed the best phloem mobility and a better systemicity than fenpiclonil acidic derivatives within the pH range of the foliar apoplast.
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Hanxiang Wu. Amino acid and glucose conjugates of a phenylpyrrole compound : synthesis, systemicity and biological properties. Biochemistry, Molecular Biology. Université de Poitiers, 2017. English. ⟨NNT : 2017POIT2261⟩. ⟨tel-02149722⟩

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