Synthesis and phloem mobility of acidic derivatives of the fungicide fenpiclonil.
A series of derivatives of the phenylpyrrole fungicide fenpiclonil was synthesized in which a carboxyl group was present at various sites of this non-phloem-mobile molecule. Using the Kleier model, all these acidic analogues were predicted to be moderately phloem-mobile, especially the N-substituted derivatives. One of these latter molecules, N-carboxymethyl-3-cyano-4-(2,3-dichlorophenyl)pyrrole, exhibited some fungicidal activity on the pathogenic fungus Eutypa lata, and was then tested as a phloem-mobile pesticide in the Ricinus system. The compound was indeed mobile in the sieve tubes and was not degraded to fenpiclonil in the phloem sap under our experimental conditions. Its concentration in the sap was closely correlated to the percentage of the undissociated form of the molecule in the external medium, and was similar under acidic conditions (external pH 4.6-5.0) to that of the herbicide glyphosate.
Chollet
Jean-François
JF
Laboratoire Synthèse et Réactivité des Substances Naturelles, Unité Mixte de Recherche CNRS 6514, 40, av du Recteur Pineau, 86022 Poitiers cedex, France.
Rocher
Françoise
F
Jousse
Cyril
C
Delétage-Grandon
Céline
C
Bashiardes
Georges
G
Bonnemain
Jean-Louis
JL
D000480:Alkynes; D001203:Ascomycota / Q000187:drug effects*; D001547:Benzaldehydes; D001692:Biological Transport; D005659:Fungicides, Industrial / Q000737:chemistry* / Q000378:metabolism; D006863:Hydrogen-Ion Concentration; D008954:Models, Biological; D018520:Plant Shoots / Q000378:metabolism*; D011758:Pyrroles / Q000737:chemistry* / Q000378:metabolism; D012278:Ricinus / Q000378:metabolism* / Q000382:microbiology*
D000480:Alkynes; D001547:Benzaldehydes; D005659:Fungicides, Industrial; D011758:Pyrroles; C102200:eutypine; C437165:fenpiclonil