title: Vectorization of agrochemicals: amino acid carriers are more efficient than sugar carriers to translocate phenylpyrrole conjugates in the Ricinus system.
abstract: Producing quality food in sufficient quantity while using less agrochemical inputs will be one of the great challenges of the twenty-first century. One way of achieving this goal is to greatly reduce the doses of plant protection compounds by improving the targeting of pests to eradicate. Therefore, we developed a vectorization strategy to confer phloem mobility to fenpiclonil, a contact fungicide from the phenylpyrrole family used as a model molecule. It consists in coupling the antifungal compound to an amino acid or a sugar, so that the resulting conjugates are handled by active nutrient transport systems. The method of click chemistry was used to synthesize three conjugates combining fenpiclonil to glucose or glutamic acid with a spacer containing a triazole ring. Systemicity tests with the Ricinus model have shown that the amino acid promoiety was clearly more favorable to phloem mobility than that of glucose. In addition, the transport of the amino acid conjugate is carrier mediated since the derivative of the L series was about five times more concentrated in the phloem sap than its counterpart of the D series. The systemicity of the L-derivative is pH dependent and almost completely inhibited by the protonophore carbonyl cyanide 3-chlorophenylhydrazone (CCCP). These data suggest that the phloem transport of the L-derivative is governed by a stereospecific amino acid carrier system energized by the proton motive force.
authors.affiliation: Institut de Chimie des Milieux et des Matériaux de Poitiers (IC2MP), Unité Mixte de Recherche CNRS 7285, Université de Poitiers, 4 rue Michel Brunet, TSA 51106, 86073, Poitiers Cedex 9, France.|Laboratoire Écologie et Biologie des Interactions, Unité Mixte de Recherche CNRS 7267, Université de Poitiers, 3 rue Jacques Fort, TSA 51106, 86073, Poitiers Cedex 9, France.
authors.forename: Hanxiang
authors.initials: H
authors.lastname: Wu
authors.affiliation: Institut de Chimie des Milieux et des Matériaux de Poitiers (IC2MP), Unité Mixte de Recherche CNRS 7285, Université de Poitiers, 4 rue Michel Brunet, TSA 51106, 86073, Poitiers Cedex 9, France.
authors.forename: Sophie
authors.initials: S
authors.lastname: Marhadour
authors.affiliation: Guizhou Tea Reasearch Institute, Guizhou Academy of Agricultural Science, Guiyang, Guizhou, 550009, China.
authors.forename: Zhi-Wei
authors.initials: ZW
authors.lastname: Lei
authors.affiliation: Guizhou Tea Reasearch Institute, Guizhou Academy of Agricultural Science, Guiyang, Guizhou, 550009, China.
authors.forename: Wen
authors.initials: W
authors.lastname: Yang
authors.affiliation: Institut de Chimie des Milieux et des Matériaux de Poitiers (IC2MP), Unité Mixte de Recherche CNRS 7285, Université de Poitiers, 4 rue Michel Brunet, TSA 51106, 86073, Poitiers Cedex 9, France.
authors.forename: Cécile
authors.initials: C
authors.lastname: Marivingt-Mounir
authors.affiliation: Laboratoire Écologie et Biologie des Interactions, Unité Mixte de Recherche CNRS 7267, Université de Poitiers, 3 rue Jacques Fort, TSA 51106, 86073, Poitiers Cedex 9, France.
authors.forename: Jean-Louis
authors.initials: JL
authors.lastname: Bonnemain
authors.affiliation: Institut de Chimie des Milieux et des Matériaux de Poitiers (IC2MP), Unité Mixte de Recherche CNRS 7285, Université de Poitiers, 4 rue Michel Brunet, TSA 51106, 86073, Poitiers Cedex 9, France. jean.franc.chollet@univ-poitiers.fr.
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Chollet
mesh_terms: D016573:Agrochemicals / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry / Q000378:metabolism*; D001692:Biological Transport; D005659:Fungicides, Industrial / Q000737:chemistry*; D005947:Glucose / Q000737:chemistry / Q000378:metabolism*; D018698:Glutamic Acid / Q000737:chemistry*; D052585:Phloem / Q000737:chemistry / Q000378:metabolism*; D011758:Pyrroles / Q000737:chemistry / Q000378:metabolism*; D012278:Ricinus / Q000737:chemistry / Q000378:metabolism*; D000073893:Sugars / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry / Q000378:metabolism*
chemical_list: D016573:Agrochemicals; D000596:Amino Acids; D005659:Fungicides, Industrial; D011758:Pyrroles; D000073893:Sugars; D014230:Triazoles; C437165:fenpiclonil; D018698:Glutamic Acid; D005947:Glucose
keywords: Carrier mediated; Fungicide; Phenylpyrroles; Phloem transport; Sustainable agriculture; Systemicity