Abstract: Chiral fungicides and compositions containing the same are provided. Also provided are methods for using the compositions of the present invention for inhibiting the growth of fungi, including phytotoxic fungi. The use of a single isomer in treating particular plant species and against particular fungi allows for selective inhibition of fungal growth with reduced fungicidal phytotoxic effects.

Abstract: N,N-disubstituted amines in which the amino nitrogen atom is bound to the carbon atom of an aromatic ring disubstituted in the positions ortho to the carbon atom, are prepared by allowing a primary amine and a compound in which an ortho, ortho-disubstituted aromatic compound carrying a nucleofuge substituent, to react in a basic environment in the presence of a catalytic palladium(0) complex and a ligand, the ratio of palladium complex to ligand being greater than at least 1:1. A typical embodiment involves the reaction of 2-methyl-6-ethylphenyl-trifluoromethylsulfonate and (S)-1-methoxy-2-aminopropane in the presence of bis(dibenzylideneacetone)palladium, tri-tert.-butylphosphine, and sodium tert.-butoxide to yield (S)-N-(1-methoxyprop-2-yl)-2-methyl-6-ethylphenylamine.