Oxidative conversion of daminozide of methylating and acylating agents

Journal Article · · Journal of Agricultural and Food Chemistry; (USA)

DOI:https://doi.org/10.1021/jf00082a037· OSTI ID:7018917

Brown, M A; Casida, J E ^[1]

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1. Univ. of California, Berkeley (USA)

Oxidation of the plant growth regulator daminozide (Alar; succinic acid, mono(2,2-dimethylhydrazide)) with m-chloroperoxybenzoic acid (MCPBA), sodium hypochlorite, or hydrogen peroxide forms not only a methylating species (probably a diazo hydroxide) that converts carboxylic acids to methyl esters but also the acylating agent succinic anhydride. Additional products are dimethylnitrosamine and methanol on MCPBA or hydrogen peroxide oxidation and 0.6 equiv of nitrogen on treatment of daminozide with 2 eqiv of MCPBA or hypochlorite. Reactive intermediates formed on oxidation of 1,1-dimethylhydrazine with 2 equiv of MCPBA also evolve nitrogen and methylate 3-chlorobenzoic acid. Metabolites of ({sup 14}C) daminozide bind to hemoglobin, liver protein, and a liver DNA fraction of treated mice and to human hemoglobin iv vitro via hydrogen peroxide oxidation, in each case with equal labeling form the ({sub 14}C) methyl and ({sub 14}C)succinyl moieties. Reactions of daminozide in these chemical oxidation models may be relevant to those in biological systems.

• OSTI ID: 7018917
• Journal Information: Journal of Agricultural and Food Chemistry; (USA), Journal Name: Journal of Agricultural and Food Chemistry; (USA) Vol. 36:4; ISSN JAFCA; ISSN 0021-8561
• Country of Publication: United States
• Language: English

Related Subjects

550201* -- Biochemistry-- Tracer Techniques
59 BASIC BIOLOGICAL SCIENCES
ACYLATION
ALCOHOLS
AMINES
ANIMALS
BIOCHEMICAL REACTION KINETICS
BIOLOGICAL EFFECTS
BODY
CARBON 14 COMPOUNDS
CARBOXYLIC ACIDS
CHEMICAL REACTIONS
DIGESTIVE SYSTEM
DNA
GLANDS
GLOBINS
HEMOGLOBIN
HETEROCYCLIC ACIDS
HETEROCYCLIC COMPOUNDS
HYDROGEN COMPOUNDS
HYDROGEN PEROXIDE
HYDROXY COMPOUNDS
ISOTOPE APPLICATIONS
KINETICS
LABELLED COMPOUNDS
LIVER
MAMMALS
MAN
METABOLISM
METABOLITES
METHANOL
METHYLATION
MICE
NITROSAMINES
NITROSO COMPOUNDS
NUCLEIC ACIDS
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANS
OXIDATION
OXYGEN COMPOUNDS
PEROXIDES
PIGMENTS
PLANT GROWTH REGULATORS
PORPHYRINS
PRIMATES
PROTEINS
REACTION INTERMEDIATES
REACTION KINETICS
RODENTS
TRACER TECHNIQUES
VERTEBRATES