| Identification | Back Directory | [Name]
SPIROTETRAMAT | [CAS]
203313-25-1 | [Synonyms]
Kontos
Movento
BYI 8330
SPIROTETRAMAT
Spirotetramat 95%
Movento from Bayer
Spirotetramat [iso]
Spirotetramat Solution
Spirotetramat Solution, 1000ppm
Spirotetramat@100 μg/mL in Acetonitrile
Spirotetramat@1000 μg/mL in Acetonitrile
Spirotetramat Solution in Methanol, 100μg/mL
(5s,8s)-3-(2,5-Dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl ethyl carbonate
Carbonic acid, cis-3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro(4.5)dec-3-en-4-Y L ethyl ester | [EINECS(EC#)]
606-523-6 | [Molecular Formula]
C21H27NO5 | [MDL Number]
MFCD11616766 | [MOL File]
203313-25-1.mol | [Molecular Weight]
373.44 |
| Chemical Properties | Back Directory | [Boiling point ]
561.0±50.0 °C(Predicted) | [density ]
1.20±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
Chloroform: Slightly soluble,Methanol: Slightly soluble | [form ]
A solid | [pka]
11.48±0.70(Predicted) | [color ]
White to light brown | [Henry's Law Constant]
1.4×107 mol/(m3Pa) at 25℃, Maniere et al. (2011) | [Stability:]
Hygroscopic | [Major Application]
agriculture
environmental | [InChI]
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+ | [InChIKey]
CLSVJBIHYWPGQY-GGYDESQDSA-N | [SMILES]
CCOC(=O)OC1=C(C(=O)NC12CCC(CC2)OC)c3cc(C)ccc3C | [LogP]
4.592 (est) | [EPA Substance Registry System]
Carbonic acid, cis-3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl ethyl ester (203313-25-1) |
| Hazard Information | Back Directory | [Uses]
Spirotetramat is a synergistic insecticide. | [Definition]
ChEBI: Spirotetramat is an 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. It has a role as a proinsecticide, an EC 6.4.1.2 (acetyl-CoA carboxylase) inhibitor and an agrochemical. It is a member of benzenes, an azaspiro compound, a carbonate ester, a gamma-lactam and a member of pyrroles. | [Production Methods]
Spirotetramat is commercially produced via a multi-step synthesis starting from 8-chloro-1,1-dimethyl-3,4-dihydro-2-benzopyran-5-one, which is condensed with ethyl 3-(dimethylamino)acrylate under basic conditions (e.g. sodium ethoxide) to form an enamine intermediate. This undergoes cyclisation with methyl chloroformate and dimethyl sulphate to yield the core cis-3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl scaffold. Subsequent O-demethylation using thiolate reagents (e.g., sodium thiomethoxide) followed by esterification with ethyl chloroformate and final hydrolysis and acidification produces the active spirotetramat acid. | [Mechanism of action]
Stomach acting, broad-spectrum, long acting insecticide that is rapidly translocated. Acetyl CoA carboxylase inhibitor (ACCase) - distrupts fatty acid biosynthesis and lipid formation. | [Pesticide Type]
Insecticide |
|
|