ABSTRACT
Methyl eugenol, is a commercially used fruit fly attractant and a suspected carcinogen. Several phenylpropenes, including methyl eugenol and the known carcinogen safrole, score negative in the Salmonella assay but score positive in the yeast DEL assay that selects for intrachromosomal recombination events in the yeast Saccharomyces cerevisiae. In an attempt to dissociate the beneficial properties of methyl eugenol from its genotoxic properties, saturated or fluorinated analogs were evaluated for their ability to induce intrachromosomal (DEL) recombination in yeast. Field tests have previously shown that all of the analogs used have appreciable properties as fruit fly attractants. The analogs 1,2-dimethoxy-4-ethylbenzene, 1,2-dimethoxy-4-(2-fluoro-2-propenyl)benzene, 1,2-dimethoxy-4-(2-fluoroethyl)benzene and 1,2-dimethoxy-4-(3-fluoro-2-propenyl)benzene all showed reduced toxicity and reduced recombinagenicity in yeast compared to methyl eugenol. These results confirm the validity of fluorination and/or removal of the 2-propenyl moiety in reducing the toxicity and recombinagenicity of methyl eugenol derivatives.
Subject(s)
Chemotactic Factors/toxicity , Eugenol/analogs & derivatives , Fluorine Compounds/toxicity , Mutagens/toxicity , Saccharomyces cerevisiae/drug effects , Animals , Chemotactic Factors/chemistry , Diptera/drug effects , Eugenol/chemistry , Eugenol/toxicity , Fluorine Compounds/chemistry , Mutagenicity Tests , Mutagens/chemistryABSTRACT
A general synthetic approach to various catechol derivatives was developed using a copper-catalyzed cross-coupling reaction of 1,2-dimethoxy-4-brornomethyl, 1-ethoxy-2-methoxy-4-bromomethyl- and 2-ethoxy-1-methoxy-4-bromomethylbenzenes with Grignard reagents. Dilithium tetrachlorocuprate was an acceptable catalyst in the dimethoxy series, whereas copper(I) iodide in THF-HMPA was a superior catalyst in all cases due to decreased side reactions, i.e., reduction and reductive coupling. Methyl-substituted analogs of methyl eugenol, a potent attractant of Oriental fruit fly,Dacus dorsalis Hendel, were synthesized by this method and evaluated for attractancy in field tests.
