188539-59-5

Usage

Uses

Used in Pest Control Industry:
5-Amino-3-cyano-4-iodo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole is used as a key intermediate in the synthesis of Fipronil, a broad-spectrum insecticide. It is particularly effective in controlling a wide range of insects by blocking the passage of chloride ions through GABA receptors in their central nervous system, leading to paralysis and eventual death of the insects.
5-AMino-3-cyano-4-iodo-1-[2,6-dichloro-4-(trifluoroMethyl)phenyl]pyrazole is valuable in the development of insecticides that can be used in various settings, such as agricultural fields, residential areas, and commercial properties, to protect crops, plants, and structures from insect infestations. Its role in the synthesis of Fipronil contributes to the creation of effective and long-lasting insect control solutions, ensuring the safety and productivity of various industries.

Upstream product

• 516-12-1 N-iodo-succinimide 
• 120068-79-3 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole 

Downstream Products

• 865834-17-9 methyl 5-amino-3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazole-4-carboxylate 
• 188538-67-2 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trimethylsilylethynylpyrazole 
• 188539-68-6 4-Acetyl-5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole 
• 188538-68-3 5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-ethynylpyrazole 
• 188539-70-0 5-Chloro-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazole 

Relevant academic research and scientific papers

The Synthesis of Fipronil Derivatives via Pd-Catalyzed Direct Alkynylation of Phenylpyrazole with Terminal Alkynes in Green Solvents

The palladium-catalyzed direct alkynylation of phenylpyrazole (5-amino-1-[2, 6-dichloro-4-trifluoromethylphenyl]-lH-pyrazole-3-carbonitrile) with terminal alkynes is being reported. The protocol utilizes EtOH/H2O as the solvents and does not require the preactivation of phenylpyrazole with halide to form its halide substrate, which exemplifies the ideal condition of green chemistry. Various terminal alkynes such as arylacetylenes and aliphatic alkynes are used in the reaction to afford a series of fipronil derivatives of 4-alkynyl-1-phenylpyrazoles with potential bioactivity in good yields. All the compounds were characterized by1H NMR,13C NMR, and HRMS spectroscopic techniques.

Lateral flow immunoassay for the simultaneous detection of fipronil and its metabolites in food samples

We developed a sensitive and rapid lateral flow immunochromatographic (LFI) assay for the simultaneous detection of fipronil and its metabolites in eggs and cucumbers using gold nanoparticle (GNP)-labeled monoclonal antibodies (mAbs). Anti-fipronil mAbs (

Hydroxy-fipronil is a new urinary biomarker of exposure to fipronil

Occupational medical surveillance is highly desirable in manufacturing facilities where exposure to chemicals is significant. The insecticide fipronil is generally considered safe for humans but with increasing use, exposure to fipronil is of concern. Ide

Substituted arylpyrazoles

This invention relates to a range of 1-aryl-4-cyclopropylpyrazoles in which there is at least one fluorine attached to the cyclopropyl ring, to compositions comprising such compounds, processes to their synthesis and their use as parasiticides.

GABA receptor antagonists and insecticides: Common structural features of 4-alkyl-1-phenylpyrazoles and 4-alkyl-1-phenyltrioxabicyclooctanes

Fipronil [5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4- trifluoromethylsulfinylpyrazole] is one of the most important insecticides. Structure-activity studies described here reveal that fipronil retains its very high binding potency at the h

Phenylpyrazole Insecticide Photochemistry, Metabolism, and GABAergic Action: Ethiprole Compared with Fipronil

Ethiprole differs from fipronil, the major phenylpyrazole insecticide, only in an ethylsulfinyl substituent replacing the trifluoromethylsulfinyl moiety. This study compares their photochemistry, metabolism, action at the γ-aminobutyric acid (GABA) receptor, and insecticidal potency. On exposure to sunlight as a thin film, ethiprole undergoes oxidation (major), reduction, and desethylsulfinylation but not desulfinylation whereas the major photoreaction for fipronil is desulfinylation. Metabolic sulfone formation is more rapid with ethiprole than fipronil in human expressed CYP3A4 in vitro and mouse brain and liver in vivo. High biological activity is observed for the sulfide, sulfoxide, sulfone, and desulfinyl derivatives in both the ethiprole and the fipronil series in GABA receptor assays (human recombinant β3 homomer and house fly head membranes) with [3H]EBOB and in topical toxicity to house flies with and without the P450-inhibiting synergist piperonyl butoxide. On an overall basis, the ethiprole series is very similar in potency to the fipronil series.

Pesticidal 1-arylpyrazoles

The invention relates to novel 1-arylpyrazole oxime derivatives, of general formula (I) or (I bis) These compounds are found to be generally safe systemic insecticides for control of arthropod, nematode, helminth or protozoan pests including compositions and derivatives thereof.

Parasiticidal pyrazoles

Compounds of formula (I): or pharmaceutically, veterinarily or agriculturally acceptable salts thereof, or pharmaceutically, veterinarily or agriculturally acceptable solvates of either entity, wherein R1 is 2,4,6-trisubstituted phenyl or 3,5-disubstitute

Parasiticidal pyrazoles

Compounds of formula (I) or pharmaceutically, veterinarily or agriculturally acceptable salts thereof, or pharmaceutically, veterinarily or agriculturally acceptable solvates of either entity, wherein R1 is 2,4,6-trisubstituted phenyl or 3,5-disubstituted pyridin-2-yl; R3 is C1 -C4 alkyl optionally substituted with hydroxy or with one or more halo; cyano, C1 to C5 alkanoyl or phenyl; R5 is hydrogen, C1 to C4 alkyl, amino or halo; R2 and R4 are each independently selected from hydrogen, C1 to C4 alkyl, fluoro, chloro and bromo or, together with the carbon atom to which they are attached, form a C3 to C6 cycloalkyl group; R6 and R8 are each independently selected from hydrogen, C1 to C4 alkyl, fluoro, chloro and bromo; or, when R2 and R4 do not form part of a cycloalkyl group, R2 and R6, together with the carbon atoms to which they are attached, may form a C5 to C7 cycloalkyl group; and R7 is hydrogen, C1 to C4 alkyl optionally substituted with one or more halo, or C1 to C4 alkoxy; are parasiticidal agents.

Parasiticidal pyrazoles

PCT No. PCT/GB97/01925 Sec. 371 Date Jan. 20, 1999 Sec. 102(e) Date Jan. 20, 1999 PCT Filed Jul. 16, 1997 PCT Pub. No. WO98/04530 PCT Pub. Date Feb. 5, 1998A new group of parasiticidal pyrazoles of formula (I) wherein R2 is NH2, H, halogen, NH(C1-6alkyl o