The reaction of a variety of organolithium compounds with sulfonate esters leads to nucleophilic substitution on sulfur, resulting in the formation of sulfones in moderate to high yields. Several new sulfones were prepared by this method.
The fungus Trichoderma viride Persoon was found to effect the hydrolysis of fenitrothion (Sumithion) and fenitrooxon in pure culture. After incubation with the test compounds, liquid cultures were extracted with ethyl acetate and the extracts were analyzed by gas chromatography for residual test compounds and their hydrolysis product, 3-methyl-4-nitrophenol. A cleanup procedure, using Amberlyst A21 resin, was developed to facilitate the analysis. Evidence was found to suggest that this nitrophenol is cometabolized by the fungus.Purity of both compounds was confirmed by mass spectroscopy and proton magnetic resonance.Aminofenitrothion was prepared by zinc/hydrochloric acid reduction of fenitrothion (Sumitomo, 1977). 3-Methyl-4-amipophenol and 3-methyl-4-nitrophenol were obtained from Aldrich Chemical Co.; the former compound was used as supplied, and the latter was recrystallized (water) before use.
The soil fungi Mortierella pusilla, M. isabellina, and Trichoderma viride, and the aquatic fungus Saprolegnia parasitica were chosen as test organisms to study the fungitoxicity of the pesticides methoxychlor and fenitrothion and some of their known metabolites and derivatives. The inhibition of mycelial growth on agar plates was used as a criterion for toxicity and it was established that the inhibiting effect was fungistatic rather than fungicidal. The results, which indicate that some metabolites are more toxic than the parent pesticides, are reported in the form of dosage response relationships and a novel method of reporting such relationships is proposed.
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