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tefluthrin
cyclopropanecarboxylic acid, 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-, (2,3,5,6-tetrafluoro-4-methylphenyl)methyl ester, (1-alpha,3-alpha(Z))-(+-)-

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CAS Number: 79538-32-2Picture of molecule3D/inchi
Other(deleted CASRN):76437-51-9
FDA UNII: 2HE8P42H2J
Nikkaji Web:J547.675E
Beilstein Number:8398039
MDL:MFCD00274607
XlogP3-AA:5.40 (est)
Molecular Weight:418.73780240
Formula:C17 H14 Cl F7 O2
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:herbicides / pesticides
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 44.60 °C. @ 760.00 mm Hg
Boiling Point: 156.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure:6.000000 mmHg @ 20.00 °C. (est)
logP (o/w): 6.500
Soluble in:
 water, 0.02 mg/L @ 20 °C (exp)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Tefluthrin 95%
Sigma-Aldrich
For experimental / research use only.
Tefluthrin PESTANAL®, analytical standard
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-duck LD50 4190 mg/kg
Pesticide Manual. Vol. 9, Pg. 791, 1991.

oral-mouse LD50 45 mg/kg
Pesticide Manual. Vol. 9, Pg. 791, 1991.

oral-rat LD50 22 mg/kg
Pesticide Manual. Vol. 9, Pg. 791, 1991.

Dermal Toxicity:
skin-rat LD50 148 mg/kg
Pesticide Manual. Vol. 9, Pg. 791, 1991.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
herbicides / pesticides
Recommendation for tefluthrin usage levels up to:
 not for fragrance use.
 
Recommendation for tefluthrin flavor usage levels up to:
 not for flavor use.
 
Safety References:
European Food Safety Authority (EFSA) reference(s):

Retrospective analysis of the immunotoxic effects of plant protection products as reported in the Draft Assessment Reports for their peer review at EU level
View page or View pdf

Reasoned opinion on the setting of maximum residue levels for tefluthrin in various crops
View page or View pdf

Modification of the existing maximum residue level for tefluthrin in carrots
View page or View pdf

Review of the existing maximum residue levels for tefluthrin according to Article 12 of Regulation (EC) No 396/2005
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :11534837
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1S,3S)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate
Chemidplus:0079538322
RTECS:GZ1227850 for cas# 79538-32-2
 
References:
 (2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1S,3S)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):11534837
Pubchem (sid):135013165
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
HMDB (The Human Metabolome Database):Search
ChemSpider:View
Wikipedia:View
Formulations/Preparations:
•emulsifiable concentrate, and granules. •force 3g insecticide (syngenta crop protection) tefluthrin 3% •force cs insecticide (syngenta crop protection) tefluthrin 23.4%, •force st insecticide (syngenta crop protection) tefluthrin 26.8% •tefluthrin technical (syngenta crop protection) tefluthrin 94% •tradenames: 'force' (amvac, syngenta); mixtures: 'imprimo' (+ imidacloprid) (bayer cropscience); 'traffic' (+ imidacloprid) (bayer cropscience). other tradenames: 'evict' (syngenta); 'forca' (syngenta); 'forza' (syngenta); 'attack' (sopra); mixtures: 'austral plus' (+ anthraquinone+ fludioxonil) (syngenta); 'montur' (+ imidacloprid) (bayer). discontinued names mixtures: 'austral' * (+ anthraquinone+ oxine-copper) (seed treatment) (la quinoline); 'elyxor star' * (+ anthraquinone+ fludioxonil) (novartis). •tech. material is about 92% pure.
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
 cyclopropanecarboxylic acid, 3-((1Z)-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-, (2,3,5,6-tetrafluoro-4-methylphenyl)methyl ester, (1R,3R)-rel-
 cyclopropanecarboxylic acid, 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-, (2,3,5,6-tetrafluoro-4-methylphenyl)methyl ester, (1-alpha,3-alpha(Z))-(+-)-
 forza
 tefluthrine
2,3,5,6-tetrafluoro-4-methylbenzyl (Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate
(2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1S,3S)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate
 

Articles:

PubMed:A site-specific ecological risk assessment for corn-associated insecticides.
PubMed:A multi-year field study to evaluate the environmental fate and agronomic effects of insecticide mixtures.
PubMed:Modeling of action potential generation in NG108-15 cells.
PubMed:Soil application of an encapsulated CO2 source and its potential for management of western corn rootworm larvae.
PubMed:The role of carbon dioxide as an orientation cue for western corn rootworm larvae within the maize root system: implications for an attract-and-kill approach.
PubMed:Use of solid phase microextraction to estimate toxicity: relating fiber concentrations to toxicity--part I.
PubMed:Parameters for pyrethroid insecticide QSAR and PBPK/PD models for human risk assessment.
PubMed:Coexpression with Auxiliary β Subunits Modulates the Action of Tefluthrin on Rat Na(v)1.6 and Na(v)1.3 Sodium Channels.
PubMed:Electrophysiological characterization of sodium-activated potassium channels in NG108-15 and NSC-34 motor neuron-like cells.
PubMed:Differential state-dependent modification of inactivation-deficient Nav1.6 sodium channels by the pyrethroid insecticides S-bioallethrin, tefluthrin and deltamethrin.
PubMed:Characterizing the effects of Eugenol on neuronal ionic currents and hyperexcitability.
PubMed:Differential state-dependent modification of rat Na(v)1.6 sodium channels expressed in human embryonic kidney (HEK293) cells by the pyrethroid insecticides tefluthrin and deltamethrin.
PubMed:Actions of Tefluthrin on Rat Na(v)1.7 Voltage-Gated Sodium Channels Expressed in Xenopus Oocytes.
PubMed:Multipesticide residue analysis in maize combining acetonitrile-based extraction with dispersive liquid-liquid microextraction followed by gas chromatography-mass spectrometry.
PubMed:Toxicity of pesticide and fertilizer mixtures simulating corn production to eggs of snapping turtles (Chelydra serpentina).
PubMed:Additivity of pyrethroid actions on sodium influx in cerebrocortical neurons in primary culture.
PubMed:Decomposition rates and residue-colonizing microbial communities of Bacillus thuringiensis insecticidal protein Cry3Bb-expressing (Bt) and non-Bt corn hybrids in the field.
PubMed:Mechanisms of pyrethroid insecticide-induced stimulation of calcium influx in neocortical neurons.
PubMed:Divergent actions of the pyrethroid insecticides S-bioallethrin, tefluthrin, and deltamethrin on rat Na(v)1.6 sodium channels.
PubMed:Wireworm management I: stand protection versus wireworm mortality with wheat seed treatments.
PubMed:Human embryonic kidney (HEK293) cells express endogenous voltage-gated sodium currents and Na v 1.7 sodium channels.
PubMed:Development of a rapid determination of pesticides in coated seeds using a high-performance liquid chromatography-UV detection system.
PubMed:Evidence for a separate mechanism of toxicity for the Type I and the Type II pyrethroid insecticides.
PubMed:Comparative functional observational battery study of twelve commercial pyrethroid insecticides in male rats following acute oral exposure.
PubMed:The mechanism of the actions of oxaliplatin on ion currents and action potentials in differentiated NG108-15 neuronal cells.
PubMed:Underlying mechanism of actions of tefluthrin, a pyrethroid insecticide, on voltage-gated ion currents and on action currents in pituitary tumor (GH3) cells and GnRH-secreting (GT1-7) neurons.
PubMed:Human and rat Nav1.3 voltage-gated sodium channels differ in inactivation properties and sensitivity to the pyrethroid insecticide tefluthrin.
PubMed:Actions of ATX-II and other gating-modifiers on Na(+) currents in HEK-293 cells expressing WT and DeltaKPQ hNa(V) 1.5 Na(+) channels.
PubMed:Modeling of action potential generation in NG108-15 cells.
PubMed:Mortality of a wireworm, Agriotes obscurus (Coleoptera: Elateridae), after topical application of various insecticides.
PubMed:Repellency of a wireworm, Agriotes obscurus (Coleoptera: Elateridae), on exposure to synthetic insecticides in a soil-less bioassay.
PubMed:Soil bioassay for studying behavioral responses of wireworms (Coleoptera: Elateridae) to insecticide-treated wheat seed.
PubMed:Effects of insecticide exposure on movement and population size estimates of predatory ground beetles (Coleoptera: Carabidae).
PubMed:Efficacy of various pyrethroid structures against a highly metabolically resistant isogenic strain of Helicoverpa armigera (Lepidoptera: Noctuidae) from China.
PubMed:Differential pharmacology of the cardiac anionic background current I(AB).
PubMed:An outwardly rectifying anionic background current in atrial myocytes from the human heart.
PubMed:Interactions of alternate hosts, postemergence grass control, and rootworm-resistant transgenic corn on western corn rootworm (Coleoptera: Chrysomelidae) damage and adult emergence.
PubMed:Abundance of Coleomegilla maculata (Coleoptera: Coccinellidae) in corn rootworm-resistant Cry3Bb1 maize.
PubMed:Toxin detection based on action potential shape analysis using a realistic mathematical model of differentiated NG108-15 cells.
PubMed:Relative potencies for acute effects of pyrethroids on motor function in rats.
PubMed:Microelectrode array recordings of cardiac action potentials as a high throughput method to evaluate pesticide toxicity.
PubMed:Structure-activity relationships for the action of 11 pyrethroid insecticides on rat Na v 1.8 sodium channels expressed in Xenopus oocytes.
PubMed:Mechanisms underlying the effects of the pyrethroid tefluthrin on action potential duration in isolated rat ventricular myocytes.
PubMed:Effect of Cry3Bb transgenic corn and tefluthrin on the soil microbial community: biomass, activity, and diversity.
PubMed:Differential effects of extracellular cesium on early afterdepolarizations in ventricular myocytes and arrhythmogenesis in isolated hearts of rats and guinea pigs.
PubMed:Differential effects of pyrethroids on volume-sensitive anion and organic osmolyte pathways.
PubMed:Larval susceptibility of an insecticide-resistant western corn rootworm (Coleoptera: Chrysomelidae) population to soil insecticides: laboratory bioassays, assays of detoxification enzymes, and field performance.
PubMed:Structure-activity and interaction effects of 14 different pyrethroids on voltage-gated chloride ion channels.
PubMed:Emergence of adult northern and western corn rootworms (Coleoptera: Chrysomelidae) following reduced soil insecticide applications.
PubMed:Determination of pyrethroid pesticide residues in processed fruits and vegetables by gas chromatography with electron capture and mass spectrometric detection.
PubMed:Cleanup of gloves contaminated with granular terbufos and tefluthrin.
PubMed:Tefluthrin modulates a novel anionic background conductance (I(AB)) in guinea-pig ventricular myocytes.
PubMed:Management of early-instar Japanese beetle (Coleoptera: Searabaeidae) in field-grown nursery crops.
PubMed:Effects of exposure time, material type, and granular pesticide on glove contamination.
PubMed:Actions of pyrethroid insecticides on sodium currents, action potentials, and contractile rhythm in isolated mammalian ventricular myocytes and perfused hearts.
PubMed:Interaction of insecticides, entomopathogenic nematodes, and larvae of the western corn rootworm (Coleoptera: Chrysomelidae).
PubMed:Selective extraction of pyrethroid pesticide residues from milk by solid-matrix dispersion.
PubMed:Clean-up of aqueous acetone vegetable extracts by solid-matrix partition for pyrethroid residue determination by gas chromatography-electron-capture detection.
PubMed:Factors Influencing Pyrethroid Resistance in a Permethrin-Selected Strain of the Soybean Looper, Pseudoplusia includens (Walker)
 
Notes:
used as an insecticide agent.
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