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Synthesis and phloem mobility of acidic derivatives of the fungicide fenpiclonil
Author(s) -
Chollet JeanFrançois,
Rocher Françoise,
Jousse Cyril,
DelétageGrandon Céline,
Bashiardes Georges,
Bonnemain JeanLouis
Publication year - 2004
Publication title -
pest management science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.296
H-Index - 125
eISSN - 1526-4998
pISSN - 1526-498X
DOI - 10.1002/ps.906
Subject(s) - phloem , sieve tube element , fungicide , pesticide , chemistry , ricinus , botany , biology , biochemistry , agronomy
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. Copyright © 2004 Society of Chemical Industry