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.
D000818:Animals; D003500:Cyclization; D003516:Cycloparaffins / Q000138:chemical synthesis* / Q000494:pharmacology; D005260:Female; D006793:Houseflies; D007306:Insecticides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013329:Structure-Activity Relationship
D003516:Cycloparaffins; D007306:Insecticides