2458-26-6 | 3-Phenyl-1H-pyrazole

Packsize	Purity	Availability	Price	Discounted Price
5g	98%	in stock	$15.00	$10.00
10g	98%	in stock	$19.00	$13.00
25g	98%	in stock	$43.00	$30.00

Description

• Catalog Number: AF28684
• Chemical Name: 3-Phenyl-1H-pyrazole
• CAS Number: 2458-26-6
• Molecular Formula: C9H8N2
• Molecular Weight: 144.17322
• MDL Number: MFCD00159654
• SMILES: c1ccc(cc1)c1n[nH]cc1

Computed Properties

• Complexity: 119
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 11
• Hydrogen Bond Acceptor Count: 1
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 1
• XLogP3: 1.9

Literature

• Impacts of the phenylpyrazole insecticide fipronil on larval fish: time-series gene transcription responses in fathead minnow (Pimephales promelas) following short-term exposure.

  The Science of the total environment 20120601

• Cytotoxic heterocyclic triterpenoids derived from betulin and betulinic acid.

  Bioorganic & medicinal chemistry 20120601

• Reactive oxygen species and mitogen-activated protein kinase induce apoptotic death of SH-SY5Y cells in response to fipronil.

  Toxicology letters 20120520

• Theoretical studies of blue phosphorescent iridium(III) complexes with phenylpyrazole and phosphines.

  Journal of nanoscience and nanotechnology 20120501

• The greening of pesticide-environment interactions: some personal observations.

  Environmental health perspectives 20120401

• Strong ligand field effects of blue phosphorescent Ir(III) complexes with phenylpyrazole and phosphines.

  Journal of nanoscience and nanotechnology 20120401

• In vitro evaluation of acaricidal activity of fipronil against Haemaphysalis bispinosa based on adult immersion test.

  Tropical biomedicine 20120301

• RFID tracking of sublethal effects of two neonicotinoid insecticides on the foraging behavior of Apis mellifera.

  PloS one 20120101

• Mechanisms underlying fipronil resistance in a multiresistant field strain of the German cockroach (Blattodea: Blattellidae).

  Journal of medical entomology 20120101

• Parasite-insecticide interactions: a case study of Nosema ceranae and fipronil synergy on honeybee.

  Scientific reports 20120101

• Fipronil is a powerful uncoupler of oxidative phosphorylation that triggers apoptosis in human neuronal cell line SHSY5Y.

  Neurotoxicology 20111201

• 4-(4-Bromo-phen-yl)-3-methyl-1-phenyl-6,7-dihydro-1H-pyrazolo-[3,4-b]thieno[2,3-e]pyridine 5,5-dioxide.

  Acta crystallographica. Section E, Structure reports online 20111201

• 4-[Bis(3-phenyl-1H-pyrazol-1-yl)meth-yl]benzene-1,2-diol.

  Acta crystallographica. Section E, Structure reports online 20111001

• Copper clean-up procedure for ultrasonic extraction and analysis of pyrethroid and phenylpyrazole pesticides in sediments by gas chromatography-electron capture detection.

  The Science of the total environment 20110815

• Differential resistance and cross-resistance to three phenylpyrazole insecticides in the planthopper Nilaparvata lugens (Hemiptera: Delphacidae).

  Journal of economic entomology 20110801

• Akt/GSK3β signaling is involved in fipronil-induced apoptotic cell death of human neuroblastoma SH-SY5Y cells.

  Toxicology letters 20110425

• Fipronil toxicity in northern bobwhite quail Colinus virginianus: reduced feeding behaviour and sulfone metabolite formation.

  Chemosphere 20110401

• Synthesis, antitumor activity and QSAR studies of some 4-aminomethylidene derivatives of edaravone.

  Bioorganic chemistry 20110201

• A fungal metabolite asperparaline a strongly and selectively blocks insect nicotinic acetylcholine receptors: the first report on the mode of action.

  PloS one 20110101

• Chemical residence time and hydrological conditions influence treatment of fipronil in vegetated aquatic mesocosms.

  Journal of environmental quality 20110101

• Evaluation of the Efficacy of Acaricides Used to Control the Cattle Tick, Rhipicephalus microplus, in Dairy Herds Raised in the Brazilian Southwestern Amazon.

  Veterinary medicine international 20110101

• Feasibility Assessment of Micro-Electrode Chip Assay as a Method of Detecting Neurotoxicity in vitro.

  Frontiers in neuroengineering 20110101

• Exposure to sublethal doses of fipronil and thiacloprid highly increases mortality of honeybees previously infected by Nosema ceranae.

  PloS one 20110101

• Effective liquid-liquid extraction method for analysis of pyrethroid and phenylpyrazole pesticides in emulsion-prone surface water samples.

  Journal of chromatography. A 20101008

• Novel tricyclic pyrazole BRAF inhibitors with imidazole or furan central scaffolds.

  Bioorganic & medicinal chemistry 20100915

• [A new type of iridium (III) phenylpyrazole complexes: synthesis, photophysical characterization].

  Guang pu xue yu guang pu fen xi = Guang pu 20100901

• Discovery and structure-activity relationship of 3-methoxy-N-(3-(1-methyl-1H-pyrazol-5-yl)-4-(2-morpholinoethoxy)phenyl)benzamide (APD791): a highly selective 5-hydroxytryptamine2A receptor inverse agonist for the treatment of arterial thrombosis.

  Journal of medicinal chemistry 20100610

• Insecticide resistance profiles and synergism in field populations of the German cockroach (Dictyoptera: Blattellidae) from Singapore.

  Journal of economic entomology 20100401

• Dynamics of fipronil in Oleo Lagoon in Jataí Ecological Station, São Paulo-Brazil.

  Chemosphere 20100301

• Malaria control under the Taliban regime: insecticide-treated net purchasing, coverage, and usage among men and women in eastern Afghanistan.

  Malaria journal 20100101

• Major effect genes or loose confederations? The development of insecticide resistance in the malaria vector Anopheles gambiae.

  Parasites & vectors 20100101

• Toxicities of fipronil enantiomers to the honeybee Apis mellifera L. and enantiomeric compositions of fipronil in honey plant flowers.

  Environmental toxicology and chemistry 20100101

• Synergistic and antagonistic effects of piperonyl butoxide in fipronil-susceptible and resistant rice stem borrers, Chilo suppressalis.

  Journal of insect science (Online) 20100101

• The Vector Population Monitoring Tool (VPMT): High-Throughput DNA-Based Diagnostics for the Monitoring of Mosquito Vector Populations.

  Malaria research and treatment 20100101

• Dissipation of fipronil in water under laboratory conditions.

  Bulletin of environmental contamination and toxicology 20091201

• Effect of fipronil on side-specific antennal tactile learning in the honeybee.

  Journal of insect physiology 20091201

• Solubilized phenyl-pyrazole ureas as potent, selective 5-HT(2A) inverse-agonists and their application as antiplatelet agents.

  Bioorganic & medicinal chemistry letters 20090915

• 1-[2,6-Dichloro-4-(trifluoro-meth-yl)phen-yl]-5-iodo-4-trifluoro-methyl-sulfinyl-1H-pyrazole-3-carbonitrile.

  Acta crystallographica. Section E, Structure reports online 20090801

• American Healthy Homes Survey: a national study of residential pesticides measured from floor wipes.

  Environmental science & technology 20090615

• Phenylpyrazole insecticides induce cytotoxicity by altering mechanisms involved in cellular energy supply in the human epithelial cell model Caco-2.

  Toxicology in vitro : an international journal published in association with BIBRA 20090601

• Rdl gene polymorphism and sequence analysis and relation to in vivo fipronil susceptibility in strains of the cat flea.

  Journal of economic entomology 20090201

• Does phenoloxidase contributed to the resistance? Selection with butane-fipronil enhanced its activities from diamondback moths.

  The open biochemistry journal 20090101

• Utilization of common ditch vegetation in the reduction of fipronil and its sulfone metabolite.

  Pest management science 20081201

• Species-specific insecticide resistance to imidacloprid and fipronil in the rice planthoppers Nilaparvata lugens and Sogatella furcifera in East and South-east Asia.

  Pest management science 20081101

• Diacetone alcohol, a dispersant solvent, contributes to acute toxicity of a fipronil-based insecticide in a passerine bird.

  Ecotoxicology and environmental safety 20081001

• Structure based development of phenylimidazole-derived inhibitors of indoleamine 2,3-dioxygenase.

  Journal of medicinal chemistry 20080828

• Development and validation of a method for fipronil residue determination in ovine plasma using 96-well plate solid-phase extraction and gas chromatography-tandem mass spectrometry.

  Journal of chromatography. A 20080801

• Phosphorescent organic light-emitting devices: working principle and iridium based emitter materials.

  International journal of molecular sciences 20080801

• Synthesis of new N-phenylpyrazole derivatives with potent antimicrobial activity.

  Bioorganic & medicinal chemistry 20080415

• Mortality of a wireworm, Agriotes obscurus (Coleoptera: Elateridae), after topical application of various insecticides.

  Journal of economic entomology 20080401

• Synthesis and biological evaluation of substituted phenylpyrazole[4,5-b]oleanane derivatives as inhibitors of glycogen phosphorylase.

  Drug discoveries & therapeutics 20080401

• Persistence and vertical distribution of termiticide fipronil in modified ground board test.

  Environmental monitoring and assessment 20080201

• Enantioselective Chronic Toxicity of Fipronil to Ceriodaphnia dubia.

  Archives of environmental contamination and toxicology 20080101

• Enantioselective microbial transformation of the phenylpyrazole insecticide fipronil in anoxic sediments.

  Environmental science & technology 20071215

• Transfer assessment of fipronil residues from feed to cow milk.

  Talanta 20071015

• Soil distribution of fipronil and its metabolites originating from a seed-coated formulation.

  Chemosphere 20071001

• Four copper(II) pyrazolido complexes derived from reactions of 3{5}-substituted pyrazoles with CuF(2) or Cu(OH)(2).

  Dalton transactions (Cambridge, England : 2003) 20070414

• Differential actions of insecticides on target sites: basis for selective toxicity.

  Human & experimental toxicology 20070401

• Toxicity of fipronil and its enantiomers to marine and freshwater non-targets.

  Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes 20070101

• Uptake and xylem transport of fipronil in sunflower.

  Journal of agricultural and food chemistry 20060712

• The developmental neurotoxicity of fipronil: notochord degeneration and locomotor defects in zebrafish embryos and larvae.

  Toxicological sciences : an official journal of the Society of Toxicology 20060701

• Phototransformation of the insecticide fipronil: identification of novel photoproducts and evidence for an alternative pathway of photodegradation.

  Environmental science & technology 20060701

• Modular approach to tridentate N,O,N' ligands using pyrazolylborate chemistry.

  Chemistry (Weinheim an der Bergstrasse, Germany) 20060614

• Bis[bis(3-phenylpyrazol-1-yl)(pyrazol-1-yl)methane]copper(II) bis(perchlorate) acetonitrile disolvate.

  Acta crystallographica. Section C, Crystal structure communications 20060201

• IMP PCR primers detect single nucleotide polymorphisms for Anopheles gambiae species identification, Mopti and Savanna rDNA types, and resistance to dieldrin in Anopheles arabiensis.

  Malaria journal 20060101

• [Susceptibility of Culex quinquefasciatus to insecticides in Bobo Dioulasso, Burkina Faso].

  Bulletin de la Societe de pathologie exotique (1990) 20051201

• Effects of sublethal doses of fipronil on the behavior of the honeybee (Apis mellifera).

  Pharmacology, biochemistry, and behavior 20050901

• Acute enantioselective toxicity of fipronil and its desulfinyl photoproduct to Ceriodaphnia dubia.

  Environmental toxicology and chemistry 20050901

• 1,5-Diphenyl-4,8-bis(3-phenylpyrazol-1-yl)pyrazabole.

  Acta crystallographica. Section C, Crystal structure communications 20050801

• Laboratory evaluation of fipronil against Periplaneta americana & Blattella germanica.

  The Indian journal of medical research 20050701

• The distinct agonistic properties of the phenylpyrazolosteroid cortivazol reveal interdomain communication within the glucocorticoid receptor.

  Molecular endocrinology (Baltimore, Md.) 20050501

• Identification of the Rdl mutation in laboratory and field strains of the cat flea, Ctenocephalides felis (Siphonaptera: Pulicidae).

  Pest management science 20041201

• Population consequences of fipronil and degradates to copepods at field concentrations: an integration of life cycle testing with leslie matrix population modeling.

  Environmental science & technology 20041201

• Design and evaluation of novel nonsteroidal dissociating glucocorticoid receptor ligands.

  Bioorganic & medicinal chemistry letters 20041018

• Fipronil is a potent open channel blocker of glutamate-activated chloride channels in cockroach neurons.

  The Journal of pharmacology and experimental therapeutics 20040701

• Fipronil modulation of GABAA receptor single-channel currents.

  Pest management science 20040501

• Crystal structure of protoporphyrinogen IX oxidase: a key enzyme in haem and chlorophyll biosynthesis.

  The EMBO journal 20040421

• In vitro metabolism of fipronil by human and rat cytochrome P450 and its interactions with testosterone and diazepam.

  Chemico-biological interactions 20040415

• 3-(4-phenoxyphenyl)pyrazoles: a novel class of sodium channel blockers.

  Journal of medicinal chemistry 20040311

• An enzyme-linked immunosorbent assay for lipovitellin quantification in copepods: a screening tool for endocrine toxicity.

  Environmental toxicology and chemistry 20040201

• Phenylpyrazole insecticide fipronil induces male infertility in the estuarine meiobenthic crustacean Amphiascus tenuiremis.

  Environmental science & technology 20040115

• Fipronil modulation of glutamate-induced chloride currents in cockroach thoracic ganglion neurons.

  Neurotoxicology 20031201

• Phenylpyrazole insecticide photochemistry, metabolism, and GABAergic action: ethiprole compared with fipronil.

  Journal of agricultural and food chemistry 20031119

• Origin and extent of resistance to fipronil in the German cockroach, Blattella germanica (L.) (Dictyoptera: Blattellidae).

  Journal of economic entomology 20031001

• Toxicity and pathogenicity of Metarhizium anisopliae var. acridum (Deuteromycotina, Hyphomycetes) and fipronil to the fringe-toed lizard Acanthodactylus dumerili (Squamata: Lacertidae).

  Environmental toxicology and chemistry 20030701

• Fipronil metabolism and dissipation in a simplified aquatic ecosystem.

  Journal of agricultural and food chemistry 20030226

• Fipronil: environmental fate, ecotoxicology, and human health concerns.

  Reviews of environmental contamination and toxicology 20030101

• Long-acting fentanyl analogues: synthesis and pharmacology of N-(1-phenylpyrazolyl)-N-(1-phenylalkyl-4-piperidyl)propanamides.

  Bioorganic & medicinal chemistry 20020301

• Reaction of malondialdehyde-DNA adducts with hydrazines-development of a facile assay for quantification of malondialdehyde equivalents in DNA.

  Chemical research in toxicology 20020301

• Toxicity of fipronil and its degradation products to Procambarus sp.: field and laboratory studies.

  Archives of environmental contamination and toxicology 20011001

• Fipronil modulation of gamma-aminobutyric acid(A) receptors in rat dorsal root ganglion neurons.

  The Journal of pharmacology and experimental therapeutics 20010301

• GLC-3: a novel fipronil and BIDN-sensitive, but picrotoxinin-insensitive, L-glutamate-gated chloride channel subunit from Caenorhabditis elegans.

  British journal of pharmacology 20010301

• Fate of a phenylpyrazole in vegetation and soil under tropical field conditions.

  Journal of agricultural and food chemistry 20010301

• Laboratory evaluation of fipronil, a phenylpyrazole insecticide, against adult Anopheles (Diptera: Culicidae) and investigation of its possible cross-resistance with dieldrin in Anopheles stephensi.

  Pest management science 20010101