Synonym
Spirotetramat; BYI 8330
IUPAC/Chemical Name
carbonic acid, cis-3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl ethyl ester
InChi Key
CLSVJBIHYWPGQY-GGYDESQDSA-N
InChi Code
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+
SMILES Code
O=C(OCC)OC1=C(C2=CC(C)=CC=C2C)C(N[C@]13CC[C@@H](OC)CC3)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Biological target:
Spirotetramat’s mode of action involves the inhibition of acetyl-CoA carboxylase enzyme activity.
In vivo activity:
Spirotetramat is implicated in developmental disturbances, malformations, and a decline in locomotor activity in zebrafish. Spirotetramat exposure led to elevated thyroid hormone levels, perturbed the hypothalamic-pituitary-thyroid (HPT) axis transcript levels, amplified deiodinase type I (Dio1) and deiodinase type II (Dio2) activities, and both transcriptionally and proteomically upregulated thyroid receptor beta (TRβ) in larvae.
Reference: Environ Pollut. 2024 Feb 15;343:123242. https://pubmed.ncbi.nlm.nih.gov/38154778/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
373.45
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Jiao F, Rong H, Zhao Y, Wu P, Long Y, Xu J, Zhao T, Han L, Wang J, Yang H. Insights into spirotetramat-induced thyroid disruption during zebrafish (Danio rerio) larval development: An integrated approach with in vivo, in vitro, and in silico analyses. Environ Pollut. 2024 Feb 15;343:123242. doi: 10.1016/j.envpol.2023.123242. Epub 2023 Dec 26. PMID: 38154778.
2. Yang J, Flaven-Pouchon J, Wang Y, Moussian B. Spirotetramat reduces fitness of the spotted-wing Drosophila, Drosophila suzukii. Insect Sci. 2023 Oct 18. doi: 10.1111/1744-7917.13283. Epub ahead of print. PMID: 37850506.
In vivo protocol:
1. Jiao F, Rong H, Zhao Y, Wu P, Long Y, Xu J, Zhao T, Han L, Wang J, Yang H. Insights into spirotetramat-induced thyroid disruption during zebrafish (Danio rerio) larval development: An integrated approach with in vivo, in vitro, and in silico analyses. Environ Pollut. 2024 Feb 15;343:123242. doi: 10.1016/j.envpol.2023.123242. Epub 2023 Dec 26. PMID: 38154778.
2. Yang J, Flaven-Pouchon J, Wang Y, Moussian B. Spirotetramat reduces fitness of the spotted-wing Drosophila, Drosophila suzukii. Insect Sci. 2023 Oct 18. doi: 10.1111/1744-7917.13283. Epub ahead of print. PMID: 37850506.
1. Civolani, S., Boselli, M., Butturini, A., et al. Testing spirotetramat as an alternative solution to abamectin for Cacopsylla pyri (Hemiptera: Psyllidae) control: Laboratory and field tests. J. Econ. Entomol. 108(6), 2737-2742 (2015).
2. Moscardini, V.F., da Costa Gontijo, P., Carvalho, G.A., et al. Toxicity and sublethal effects of seven insecticides to eggs of the flower bug Orius insidiosus (Say) (Hemiptera: Anthocoridae). Chemosphere 92(5), 490-496 (2013).
3. Yin, X., Jiang, S., Yu, J., et al. Effects of spirotetramat on the acute toxicity, oxidative stress, and lipid peroxidation in Chinese toad (Bufo bufo gargarizans) tadpoles. Environ. Toxicol. Pharmacol. 37(3), 1229-1235 (2014).
