Acidic derivatives of the fungicide fenpiclonil: effect of adding a methyl group to the N-substituted chain on systemicity and fungicidal activity.

A new acidic derivative of the fungicide fenpiclonil was synthesized containing a methyl group on the alpha-position of the carboxyl function of N-carboxymethyl-3-cyano-4-(2,3-dichlorophenyl)pyrrole. The phloem mobility of the resulting N-(1-carboxyethyl)-3-cyano-4-(2,3-dichlorophenyl)pyrrole was comparable with that of the former compound, but was higher at external pH 5.0.

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.

Synthesis of non-immunosuppressive cyclophilin-Binding cyclosporin A derivatives as potential anti-HIV-1 drugs.

Original cyclosporin A (CsA) derivatives bearing various alkylthio side chains at the sarcosine residue 3 (R configuration) and for the most potent and selective compounds a 4'-hydroxyl group at the Me-Leucine residue 4 were prepared in one or two steps from commercially available CsA. The [2-(dimethyl or diethylamino)-ethylthio-Sar](3)-[(4'-OH)MeLeu](4)-CsA derivatives 3k and 3l displayed potent in vitro anti-HIV-1 (IC(50) approximately 46 nM) and low immunosuppressive activities (IC(50)>or=1500 nM).