Fungistatic activity of cations of nonaromatic amines

Abstract

Methylpyrrolidine and seobutylamine were the most active of 50 nonaromatic amines tested in their cationic form for inhibition of germination of Penicillium digitatum spores. Pyrrolidine, 2-methylpyrrolidine, isopropylamine, l-methyl-2-propenylamine, and cyclobutylamine showed lesser activity, but all other simple amines tested were not inhibitory. Replacement of the C-l or C-4 methyl group of seobutylamine with CF3, CC13, COOH, OCH3, CH2OH, Cl, NH2, or OH resulted in compounds which were not active. ( -)-seoButylamine was considerably more active than the (+) enantiomer, both in preventing spore germination and in inhibiting mycelial growth of three species of fungi which were sensitive to racemic seobutylamine. (-)-seoButylamine and 3-methylpyrrolidine were uniquely effective in preventing infection of citrus fruits by P. digitatum. The receptor site for inhibitory amines on the fungus cell appears to consist of an anionic component which binds the -NH3+ group and a hydrophobic area which is complementary to the sec-butyl radical as spatially oriented in (-)-seobutylamine.The antifungal properties of aliphatic amines, guanidines, and quaternary ammonium compounds with more than ten carbon atoms are well known (Byrde, 1969), but lower aliphatic amines in their cationic form are not generally considered to be fungitoxic by usual standards of comparison. sec-Butylamine (2-aminobutane) was found to be anomalous

Diastereoselective Synthesis of β-Substituted-α,γ-Diaminobutyric Acids and Pyrrolidines Containing Multichiral Centers

“…Depending on the substitution pattern and functionalization, pyrrolidines have been reported to possess different important biological activities. They can act as antibacterials, neuroexcitatory agents, glycosidase inhibitors, and fungicides . However, their construction with predictable regio- and stereocontrol still constitutes a challenge in organic chemistry.…”

“…They can act as antibacterials, 11 neuroexcitatory agents, 12 glycosidase inhibitors, 13 and fungicides. 14 However, their construction with predictable regio-and stereocontrol still constitutes a challenge in organic chemistry.…”

Studies on the selective fungitoxicity of aliphatic amines

“…The fungitoxicity of long-chain aliphatic amines, guanidines, and other basic organic compounds in neutral solution increases with hydrophobicity which, in turn, correlates with intensity of binding and damage to the cytoplasmic membrane (Albert, 1985;Eckert et al, 1972;Solel and Siegel, 1984). In contrast, ammonia and most simple aliphatic amines (<C6) are not active under the same conditions, but their toxicity increases with the pH of the solution because the neutral form of these molecules penetrates the cell membrane with comparative ease (Albert, 1985).…”