Spiroxamine
Basic information
- CAS
118134-30-8- Standard SMILES
CCCN(CC)CC1COC2(CCC(C(C)(C)C)CC2)O1- InChIKey
PUYXTUJWRLOUCW-UHFFFAOYSA-N- Molecular formula
- C18H35NO2
- Average molar mass
- 297.5 g/mol
- Monoisotopic mass
- 297.26677936
Overview
Spiroxamine is 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 powdery mildew in the production of cereals, bananas and grapes. It has a role as a xenobiotic, an environmental contaminant, a sterol biosynthesis inhibitor and an antifungal agrochemical. It is a dioxolane, a tertiary amino compound and a spiroketal.
Names & identifiers
- Preferred name
- Spiroxamine
- IUPAC
- N-[(8-tert-butyl-1,4-dioxaspiro[4.5]decan-3-yl)methyl]-N-ethylpropan-1-amine
- English name
- Spiroxamine
- Molecular formula
- C18H35NO2
- Molecular weight
- 297.48
Names & synonyms
Spiroxamine118134-30-8ImpulseDTXSID1034212OUT5YHB7BOKWG4168KWG-41681,4-Dioxaspiro(4.5)decane-2-methanamine, 8-(1,1-dimethylethyl)-N-ethyl-N-propyl-CHEBI:9242DTXCID90142128-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro(4.5)decane-2-methanamineN-[(8-tert-butyl-1,4-dioxaspiro[4.5]dec-2-yl)methyl]-N-ethylpropan-1-amine
Show more names
SPIROXAMINKWG 4168Spiro aMineSpirocyclineSpiroxamine 0SpirocyclovirProsper HoggarSpiroketalaMine
((8-tert-butyl-1,4-dioxaspiro(4.5)decan-2-yl)methyl)(ethyl)propylamine(8-Tert-butyl-1,4-dioxa-spiro(4.5)dec-2-ylmethyl)-ethyl-propyl-amine(8-tert-Butyl-1,4-dioxa-spiro[4.5]dec-2-ylmethyl)-ethyl-propyl-amine8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamineN-((8-tert-butyl-1,4-dioxaspiro(4.5)dec-2-yl)methyl)-N-ethylpropan-1-amineRefChem:184959spiroxamine (ISO); 8-tert-butyl-1,4-dioxaspiro(4.5)decan-2-ylmethyl(ethyl)(propyl)amine601-505-4
Database identifiers
Properties
Computed structural properties
- XLogP
- 4.2
- Topological polar surface area
- 21.7 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 6
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 316
Experimental & physicochemical properties
Pesticides
Agrochemicals -> Pesticide active substances
Active substance -> EU Pesticides database: Approved
Fungicides
Pesticide
Environmental transformation -> Pesticides (parent, predecessor)
Pesticide (Spiroxamine) -> USDA PDB
Human DrugsPharmaceuticals
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section
176.6 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID1034212]
182.9 Ų [M+H]+
Physicochemical properties
- Melting point
- 25 °C · <25 °C
- Boiling point
- 120 ° · bp 120° at 0.067 hPa
- Density
- 0.96 · 0.96±0.1 g/cm3(Predicted)
- refractive index
- 20 · nD20 1.4662
- Flash point
- 147 °C · 147 °C
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P203, P260, P261, P264, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P317, P318, P319, P321, P330, P332+P317, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)
Warning
H302+H312+H332 (64.8%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
P203, P260, P261, P264, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P317, P318, P319, P321, P330, P332+P317, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)
Hazard information
Regulatory Information
Commission Regulation (EC) No 737/2007
Spiroxamine is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)
2007/21/EC, 99/73/EC, Reg. (EU) 2023/2592, Reg. (EU) 2026/372 , Reg. (EU) No 2019/291, Reg. (EU) No 540/2011, Reg. (EU) No 797/2011
Spiroxamine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and Categories
Acute Tox. 4 (100%)
Acute toxicity - category 4
Repr. 2
Toxicology
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
RAIS Toxicity Values
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationChemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc.
Uses & manufacturing
UsesThis is a man-made compound that is used as a pesticide.
Use Classification
Environmental transformation -> Pesticides (parent, predecessor)
Pharmaceuticals
Fungicides
Applications
DescriptionSpiroxamine 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).
UsesSpiroxamine is a spiroketalamine fungicide for use on cereal crops. Spiroxamine inhibits ergosterol synthesis. Spiroxamine is used as agricultural fungicide.
Additional notes
DefinitionChEBI: 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.
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Compound notes
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