| Identification | Back Directory | [Name]
SPIROXAMINE | [CAS]
118134-30-8 | [Synonyms]
IMpulse
KWG 4168
SPIROXAMIN
SPIROXAMINE
Spiro aMine
Spiroxamine 0
Prosper Hoggar
SpiroketalaMine
Spiroxamine [iso]
spiroxamine (iso proposed)
SpiroxamineSolution,100mg/L,1ml
Spiroxamine 100mg [118134-30-8]
SpiroxamineSolution,100mg/L,5x1ml
Spiroxamine@1000 μg/mL in Acetonitrile
Spiroxamine Standard(mixture of isomers)
Spiroxamine solution in Methanol，100μg/mL
n-ethyl-n-propyl-8-tert-butyl-1,4-dioxaspiro[4.5]dec-2-ylmethylamine
1,4-Dioxaspiro4.5decane-2-methanamine, 8-(1,1-dimethylethyl)-N-ethyl-N-propyl-
8-(1,1-DiMethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-MethanaMine
N-((8-(tert-Butyl)-1,4-dioxaspiro[4.5]decan-2-yl)methyl)-N-ethylpropan-1-amine | [Molecular Formula]
C18H35NO2 | [MDL Number]
MFCD03095708 | [MOL File]
118134-30-8.mol | [Molecular Weight]
297.48 |
| Chemical Properties | Back Directory | [Melting point ]
<25 °C | [Boiling point ]
bp 120° at 0.067 hPa | [density ]
0.96±0.1 g/cm3(Predicted) | [refractive index ]
nD20 1.4662 | [Fp ]
147 °C | [storage temp. ]
0-6°C | [solubility ]
Chloroform: Slightly Soluble | [form ]
neat | [pka]
6.9(at 25℃) | [color ]
Colorless to light yellow | [Henry's Law Constant]
4.0×102 mol/(m3Pa) at 25℃, Maniere et al. (2011) | [Stability:]
Hygroscopic | [Major Application]
agriculture
environmental | [InChI]
1S/C18H35NO2/c1-6-12-19(7-2)13-16-14-20-18(21-16)10-8-15(9-11-18)17(3,4)5/h15-16H,6-14H2,1-5H3 | [InChIKey]
PUYXTUJWRLOUCW-UHFFFAOYSA-N | [SMILES]
CCCN(CC)CC1COC2(CCC(CC2)C(C)(C)C)O1 | [LogP]
4.880 (est) | [EPA Substance Registry System]
Spiroxamine (118134-30-8) |
| Hazard Information | Back Directory | [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). | [Uses]
Agricultural fungicide. | [Uses]
Spiroxamine is a spiroketalamine fungicide for use on cereal crops. Spiroxamine inhibits ergosterol synthesis. Spiroxamine is used as agricultural fungicide. | [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. | [Production Methods]
The production of spiroxamine involves a two-step synthesis process optimized for industrial scalability and environmental safety. First, a compound (referred to as X) reacts with an alkylamine in the presence of a base to form an intermediate compound (XI). In the second step, compound XI undergoes a reaction with an alkyl bromide and a base under the influence of a phase transfer catalyst to yield spiroxamine. | [Mechanism of action]
Systemic with protective, curative and eradicative action. Disrupts membrane function. Inhibits sterol biosynthesis in membranes. | [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 | [Pesticide Type]
Fungicide |
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