[Microbial breakdown of acid anilide fungicides (author's transl)]. 1976

R Bachofer

o-Toluylanilide, 2.5-dimethylfuran-3-carboxanilide, 5.6-dihydro-2-methyl-1.4-oxathiine-3-carboxanilide and other acid anilides are systemic fungicides which act selectively on rusts and smuts. From garden soil a Nocardia sp. was isolated which can grow with acid anilide fungicides as the only source of carbon. From this Nocardia sp. it was possible to produce mutants which are blocked genetically at various steps of the breakdown pathway of these acid anilide fungicides. It was possible to follow the breakdown pathway with the aid of accumulates of the rough I strain and of the mutants as well as by growth and enzyme tests. Breakdown starts with hydrolytic splitting of the acid amide bond by an acylamidase. The acid components of the fungicides are accumulated in the medium; they do not affect the growth. The aniline component is oxidized to pyrocatechol by a dioxygenase. Methyl and chloro-derivatives of aniline which are formed in the soil due to the hydrolysis of herbicides and fungicides, are also converted into the respective pyrocatechol derivatives. By orthocleavage cis-cis muconic acid forms from pyrocatechol. This compound is metabolized into succinate and acetyl CoA via the beta ketoadipate pathway.

UI MeSH Term Description Entries
D009154 Mutation Any detectable and heritable change in the genetic material that causes a change in the GENOTYPE and which is transmitted to daughter cells and to succeeding generations. Mutations
D009615 Nocardia A genus of gram-positive, aerobic bacteria whose species are widely distributed and are abundant in soil. Some strains are pathogenic opportunists for humans and animals. Micropolyspora
D010105 Oxygenases Oxidases that specifically introduce DIOXYGEN-derived oxygen atoms into a variety of organic molecules. Oxygenase
D002396 Catechols A group of 1,2-benzenediols that contain the general formula R-C6H5O2. Pyrocatechols,o-Dihydroxybenzenes,ortho-Dihydroxybenzenes,o Dihydroxybenzenes,ortho Dihydroxybenzenes
D002621 Chemistry A basic science concerned with the composition, structure, and properties of matter; and the reactions that occur between substances and the associated energy exchange.
D005659 Fungicides, Industrial Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc. Industrial Fungicides
D000581 Amidohydrolases Any member of the class of enzymes that catalyze the cleavage of amide bonds and result in the addition of water to the resulting molecules. Amidases,Amidohydrolase
D000813 Anilides Any aromatic amide obtained by acylation of aniline.
D000814 Aniline Compounds Compounds that include the aminobenzene structure. Phenylamine,Phenylamines,Anilines,Compounds, Aniline
D001673 Biodegradation, Environmental Elimination of ENVIRONMENTAL POLLUTANTS; PESTICIDES and other waste using living organisms, usually involving intervention of environmental or sanitation engineers. Bioremediation,Phytoremediation,Natural Attenuation, Pollution,Environmental Biodegradation,Pollution Natural Attenuation

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