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CHEBI:81975 - spirotetramat

ChEBI IDCHEBI:81975
ChEBI Namespirotetramat
Stars
DefinitionAn azaspiro compound that is methoxycyclohexane which is fused at position 4 to the 5-position of a 1,5-dihydro-2H-pyrrol-2-one that is substituted at positions 3 and 4 by 2,5-dimethylphenyl and (ethoxycarbonyl)oxy groups, respectively (the cis isomer). It is a proinsecticide (via hydrolysis of the ethyl carbonate group to give the corresponding 4-hydroxypyrrol-2-one, "spirotetramat-enol") and is used for the control of a wide range of sucking insects on fruit and potato crops.
Last Modified19 July 2018
DownloadsMolfile
FormulaC21H27NO5
Net Charge0
Average Mass373.449
Monoisotopic Mass373.18892
SMILESCCOC(=O)OC1=C(c2cc(C)ccc2C)C(=O)N[C@]12CC[C@@H](OC)CC2
InChIInChI=1S/C21H27NO5/c1-5-26-20(24)27-18-17(16-12-13(2)6-7-14(16)3)19(23)22-21(18)10-8-15(25-4)9-11-21/h6-7,12,15H,5,8-11H2,1-4H3,(H,22,23)/t15-,21+
InChIKeyCLSVJBIHYWPGQY-GGYDESQDSA-N
Roles Classification
Biological Role:
EC 6.4.1.2 (acetyl-CoA carboxylase) inhibitor  An EC 6.4.1.* (C‒C bond-forming ligase) inhibitor that interferes with the action of acetyl-CoA carboxylase (EC 6.4.1.2).
Applications:
agrochemical  An agrochemical is a substance that is used in agriculture or horticulture.
proinsecticide  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active insecticide for which it is a proinsecticide.
ChEBI Ontology
Outgoing Relation(s)
spirotetramat (CHEBI:81975) has role agrochemical (CHEBI:33286)
spirotetramat (CHEBI:81975) has role EC 6.4.1.2 (acetyl-CoA carboxylase) inhibitor (CHEBI:70722)
spirotetramat (CHEBI:81975) has role proinsecticide (CHEBI:136644)
spirotetramat (CHEBI:81975) is a azaspiro compound (CHEBI:35624)
spirotetramat (CHEBI:81975) is a benzenes (CHEBI:22712)
spirotetramat (CHEBI:81975) is a carbonate ester (CHEBI:46722)
spirotetramat (CHEBI:81975) is a pyrroles (CHEBI:26455)
spirotetramat (CHEBI:81975) is a γ-lactam (CHEBI:74222)
IUPAC Name 
(5s,8s)-3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl ethyl carbonate
Synonyms  Source
cis-3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl ethyl carbonateAlan Wood's Pesticides
ethyl cis-8-methoxy-2-oxo-3-(2,5-xylyl)-1-azaspiro[4.5]dec-3-en-4-yl carbonateAlan Wood's Pesticides
cis-3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl ethylcarbonateChEBI
Brand Names  Source
UltorChemIDplus
MoventoChemIDplus
Manual XrefsDatabases
C18807KEGG COMPOUND
spirotetramatAlan Wood's Pesticides
EP2039248Patent
1119PPDB
Registry NumbersSources
Reaxys:14441154Reaxys
CAS:203313-25-1KEGG COMPOUND
CAS:203313-25-1Alan Wood's Pesticides
CAS:203313-25-1ChemIDplus
Citations