Stereoselective Syntheses and Biological Properties of (E)-α-(Methoxyimino) -2-[1- (aryloxy) methyl] -benzeneacetates1

(E)-α-(Methoxyimino)-2-[1-(aryloxy)methyl] -benzeneacetates, the analogues of Kresoxim-methyl, were stereoselectively synthesized with the coupling reaction of 2-methylphenyldiazonium chloride and methyl 2-hydroxyiminoacetate in the presence of CuSO4/Na2SO3 as a key step, and it was first found that the coupling reaction could give the key intermediate material(E)- and(Z)-methyl 2-(hydroxyimino)-2-o-tolylacetate with a molar ratio of 14:1. The (E)-configurations of all these compounds were assigned on the basis of their 2D-NOESY spectra of 1H NMR. The preliminary bioassays indicate that most of the compounds show an activity against a wide variety of fungi.