J. Anim Sci.
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J. Anim Sci. 1971. 33:497-501.
© 1971 American Society of Animal Science
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Photolysis of 1-{alpha}-Methylallylthiocarbamoyl-2-Methylthiocarbamoylhydrazine (Methallibure) to a Thiadiazole in the Presence and Absence of Rumen Microorganisms

P. P. Williams, P. W. Aschbacher and V. J. Feil1, 2,

U.S. Department of Agriculture, Fargo, North Dakota 58102

Abstract

Methallibure (1-{alpha}-methylallylthiocarbamoyl-2-methylthiocarbamoyl-hydrazine), an orally administered inhibitor of estrus in ruminants and monogastrics, was found to be stable in darkness in the low redox potential (E0', pH 6.85, –123 mv) of anaerobic microbial media. In media incubated under fluorescent light, methallibure-14C (1-{alpha}-methylallylthiocarb-14C-amoyl-2-methylthiocarbamoylhydrazine) degraded (about 38% in 72 hr.) with loss of H2S intramolecularly to form a thiadiazole, 2-methylamino-5-({alpha}-methylallylamino)-1,3,4-thiadiazole. Thin-layer, column and gas-liquid chromatographic methods were discussed for isolation of the thiadiazole in pure form from culture media. Methallibure dried on silica gel and exposed to fluorescent and ultraviolet sources was degraded; the compound was stable under the same conditions in darkness. Rumen digesta, mixtures of rumen bacterial cells with and without supplemental nutrients, and rumen ciliates showed no apparent degradation of methallibure-14C. Rumen bacterial species exposed to methallibure for 5 days and then to methallibure-14C showed little, if any, conversion of methallibure-14C to the thiadiazole or other products. Absorbency and zone of inhibition tests with rumen bacterial cultures showed no growth inhibition to methallibure up to 250 µg per disk.

Footnotes

1 Metabolism and Radiation Research Laboratory, Animal Science Research Division, A.R.S.

2 The assistance of Mary C. Helgeson and R. G. Zaylskie is gratefully acknowledged.






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Copyright © 1971 by the American Society of Animal Science.