p-Bromoaniline is rapidly acetylated by four soil microorganisms. Two fungal species convert metobromuron to p-bromoacetanilide, but a bacterial and an algal species do not metabolize metobromuron. Acetylation may serve as a detoxification mechanism by competing with azobenzene formation in utilizing the aniline formed by metabolism of substituted urea herbicides.

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The effects of 2-chloro-4-ethylamino-6-isopropylamino-s-triazine (atrazine), N,N-dimethyl-2,2-diphenyl-acetamide (diphenamid), and N-(p-bromophenyl)-N'-methyl-N'-methoxyurea (metobromuron) upon autotrophic growth of four unicellular green algae were studied. Growth of Chlamydomonas reinhardi Dangeard was completely inhibited by 1 μg/ml metobromuron or 0.5 μg/ml atrazine and was stimulated by diphenamid. Five μg/ml metobromuron were toxic to Chlamydomonas eugametos Moewus, while atrazine and diphenamid had little effect on growth. Growth of Chlorella vulgaris Beijerinck was partially inhibited by atrazine and stimulated by diphenamid and metobromuron. At high concentrations, atrazine or metobromuron inhibited Chlorella pyrenoidosa Chick while growth was stimulated by diphenamid. The results obtained by treating with a combination of atrazine and metobromuron varied greatly with the organism. The effect of these three herbicides upon heterotrophic growth of Chlamydomonas reinhardi also was investigated. Both metobromuron and diphenamid were toxic in the dark. Atrazine had no effect upon heterotrophic growth.

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