1,224,943. Zearalane derivatives. COMMERCIAL SOLVENTS CORP., and MERCK & CO. Inc. 12 May, 1969 [15 May, 1968], No. 24122/69. Heading C2C. Zearalane derivatives of the general formula (in which T is -CH=CH- or -CH 2 .CH 2 -, Z is CH 2 , C: O or CHOR; R is hydrogen, a substituted or unsubstituted alkyl group of from 1 to 15 carbon atoms, an acyl group of from 1 to 25 carbon atoms or a monocyclic aralkyl group containing up to 10 carbon atoms; X and XSP1/SP are hydrogen, -OR, or -ORSP1/SP; RSP1/SP is benzoxazolyl, benzthiazolyl or phenyltetrazolyl; each Y is independently hydrogen, amino, nitro, or hydroxyl; with the proviso that at least one of X and XSP1/SP is benzoxazolyloxy, benzthiazolyloxy or hydrogen, and provided that X and XSP1/SP are not both hydrogen when Y is hydrogen, Z is -CH 2 - and T is -CH 2 .CH 2 -) may be prepared by selectively etherifying at least one of the 2- and 4-etherifying at least one of the 2- and 4-positions (OR's) of compounds of general formula (R, T, Y and Z are as above defined) with 2- chlorobenzothiazole, 2 - chlorobenzoxazole, or 1 - phenyl - 5 - chlorotetrazole, and if desired hydrogenolysing the heterocyclic ether group to replace it by a hydrogen atom. The novel compounds exhibit estrogenic activity or aid the growth rate in meat producing animals. They can be administered orally or parenterally, e.g. in an injection medium such as peanut oil, or in animal feed compositions comprising carbohydrates, proteins, minerals and vitamins. Intermediate compounds of the first formula above in which XSP1/SP is tetrahydropyranyloxy are prepared by use of dihydropyran as the etherifying agent.
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