SUBSTITUENT EFFECTS ON CHEMOSTERILANT ACTIVITY OF 2,4-DI-TERT-BUTYL-6-(4'-SUBSTITUTED BENZYL)PHENOLS IN THE HOUSE-FLY (MUSCA-DOMESTICA L)

A series of 2,4-di-tert-butyl-6-(4'-X-benzyl)phenols was prepared, ana logous to the compound Jurd 2644 (X = OMe) in an attempt to establish a Hammett relationship between the 4'-substituent and the chemosterila nt activity of the compounds after oral administration to adult Musca domestica. Fourteen compounds of this type were prepared, 12 of them n ew. Jurd 2419 (X = H) was found to be as active in our bioassay as Jur d 2644, as were four new compounds [X = N(CH3)(2), CH3, SCH3, Cl]. All prevented successful reproduction at 30 mg/kg of diet. There was no c orrelation between Hammett a and activity. Active compounds all had sm all substituents and molecular weights below 350. The activity seemed to be determined by the bulk of X rather than by its electronic proper ties.