Fipronil

Names

[ CAS No. ]:
120068-37-3

[ Name ]:
Fipronil

[Synonym ]:
Fipronil (JAN)
5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrazole-3-carbonitrile
5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethanesulfinyl)-1H-pyrazole-3-carbonitrile
Fluocyanobenpyrazole
EINECS 424-610-5
5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile
1H-Pyrazole-3-carbonitrile, 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-
5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazole
(±)-Fipronil
5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethyl)sulfinyl-1H-pyrazole-3-carbonitrile
(±)-5-Amino-1-(2,6-dichloro-a,a,a-trifluoro-p-tolyl)-4-trifluoromethylsulfinylpyrazole-3-carbonitrile
RM 1601
MFCD00867812
Termidor
T5NNJ AR BG FG DXFFF& CCN DSO&XFFF EZ &&(RS) Form
5-Amino-1-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)-4-[(trifluoromethyl)sulfinyl]pyrazole-3-carbonitrile
Fipronil

Biological Activity

[Description]:

Fipronil is an insecticide that acts as a selective antagonist of insect GABA receptors (IC50s = 30 nM and 1,600 nM for cockroach and rat receptors, respectively). Fipronil also inhibits desensitizing and non-desensitizing glutamate-induced chloride currents in cockroach neurons (IC500s = 800 nM and 10 nM, respectively). Fipronil induces activity of the cytochrome P450 (CYP) isoforms CYP1A1/2, CYP2B1/2, and CYP3A1/2 in isolated rat liver microsomes.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450

Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor

Signaling Pathways >> Neuronal Signaling >> GABA Receptor

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Boiling Point ]:
510.1±50.0 °C at 760 mmHg

[ Melting Point ]:
200-201°C

[ Molecular Formula ]:
C₁₂H₄Cl₂F₆N₄OS

[ Molecular Weight ]:
437.148

[ Flash Point ]:
262.3±30.1 °C

[ Exact Mass ]:
435.938690

[ PSA ]:
103.91000

[ LogP ]:
4.76

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.618

[ Storage condition ]:
0-6°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS06, GHS08, GHS09

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301 + H311 + H331-H319-H372-H410

[ Precautionary Statements ]:
P261-P273-P280-P301 + P310 + P330-P302 + P352 + P312-P304 + P340 + P312

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
N: Dangerous for the environment;T: Toxic;

[ Risk Phrases ]:
R23/24/25

[ Safety Phrases ]:
S26-S36/37/39-S45-S60-S61

[ RIDADR ]:
2588

[ WGK Germany ]:
3.0

[ RTECS ]:
UQ4430250

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Superficially porous particles vs. fully porous particles for bonded high performance liquid chromatographic chiral stationary phases: isopropyl cyclofructan 6.

J. Chromatogr. A. 1363 , 89-95, (2014)

This work reports a comparison of HPLC separations of enantiomers with chiral stationary phases (CSPs) prepared by chemically bonding cyclofructan-6, functionalized with isopropyl carbamate groups on ...

Persistence and effect of processing on reduction of fipronil and its metabolites in chilli pepper (Capsicum annum L.) fruits.

Environ. Monit. Assess. 186(9) , 5429-37, (2014)

A single laboratory UPLC-MS/MS method was developed and validated for the estimation of fipronil and its metabolites in fresh and dry chilli pepper fruits. Dissipation of fipronil on chilli fruits was...

Acute toxicity and sublethal effects of fipronil on detoxification enzymes in juvenile zebrafish (Danio rerio)

Pestic. Biochem. Physiol. 115 , 9-14, (2014)

The acute toxicity of fipronil and its sublethal effects on detoxification enzymes (carboxylesterases (CarEs), glutathione S-transferases (GSTs), and 7-ethoxycoumarin O-deethylase (ECOD)) in zebrafish...