Diels-Alder adducts of fulvenes and halogenated dienes. Synthesis and insecticidal activity

A series of eight adducts (1--8) of substituted fulvenes and polychlorinated cyclodienes was synthesized by Diels-Alder cyclization. The products isolated were the endo bicyclo adducts as determined by detailed 1H and 13C NMR spectral analysis. Steric hindrance of end-product bridge substituents coupled with bulky substituents at C6 of the fulvenes led to one isomeric product in most cases. Compounds 1--8 demonstrated weak insecticidal action in Musca domestica as determined by topical LD50 and oral LC50 assays.