Description
Spiroxamine is a tertiary amine fungicide and an inhibitor of Δ14 reductase/Δ8→Δ7 isomerase. It inhibits the growth of N. parvum, B. dothidea, D. seriata, and L. theobromae isolates from grape vines (EC50s = 0.97-10.28 mg/L). Spiroxamine (0.03-30 μM) reduces network formation in rat cortical cultures. It is also cytotoxic to MDA-kb2 cells (EC20 = 9.29 μM).
Definition
ChEBI: The spiroketal resulting from the formal condensation of 4-tert-butylcyclohexanone with 3-[ethyl(propyl)amino]propane-1,2-diol. An inhibitor of ergosterol synthesis, it is a broad spectrum agricultural fungicide used particularly against powde
y mildew in the production of cereals, bananas and grapes.
Metabolic pathway
Spiroxamine is metabolized rapidly in plants, soils,
water, and animals via similar degradation pathways.
The metabolic pathways include hydrolysis and
oxidation at several places in the molecule. Side
chains are also degraded to various water-soluble
conjugates in animals and in plants, and at the end of complete degradation to natural constituents, carbon
dioxide is formed in soils as the principal metabolite.
The favorable sorption characteristics rule out any
possibility of appreciable translocation in soil. In wheat,
the total residue is determined in forage, grain, and
harvest-ready straw. In the field studies, the residues in
the grain are mostly below 0.05 mg kg-1, and only in a
few cases up to 0.3 mg kg-1. In the milk of cows
ingesting spiroxamine residues with the feed, no
residues are found in the least favorable case. In eggs
of laying hens, the residue concentrations are below the
limit of quantification. There are no residue
concentrations detected in the hen fat, meat, and liver.
References
[1] GUOQING SUI. Trialkylamine Derivatives Containing a Triazole Moiety as Promising Ergosterol Biosynthesis Inhibitor: Design, Synthesis, and Antifungal Activity.[J]. Chemical & pharmaceutical bulletin, 2017, 2 4: 82-89. DOI:
10.1248/cpb.c16-00732[2] CHRISTOPHER L FRANK. From the Cover: Developmental Neurotoxicants Disrupt Activity in Cortical Networks on Microelectrode Arrays: Results of Screening 86 Compounds During Neural Network Formation.[J]. Toxicological Sciences, 2017: 121-135. DOI:
10.1093/toxsci/kfx169[3] FRANCES ORTON. Widely used pesticides with previously unknown endocrine activity revealed as in vitro antiandrogens.[J]. Environmental Health Perspectives, 2011, 119 6: 794-800. DOI:
10.1289/ehp.1002895
