metaflumizone
hydrazinecarboxamide, 2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(trifluoromethoxy)phenyl]-, (2E)-
 
Notes:
an insecticide.
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CAS Number: 139968-49-3Picture of molecule3D/inchi
Other(deleted CASRN): 875656-67-0
FDA UNII: 71I50E2UDI
Nikkaji Web: J2.185.060H
MDL: MFCD08690508
XlogP3-AA: 6.20 (est)
Molecular Weight: 506.40833920
Formula: C24 H16 F6 N4 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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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Flash Point: 32.00 °F. TCC ( 0.00 °C. ) (est)
logP (o/w): 6.055 (est)
Soluble in:
 water, 8.998e-005 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Santa Cruz Biotechnology
For experimental / research use only.
Metaflumizone
Sigma-Aldrich
For experimental / research use only.
Metaflumizone PESTANAL®, analytical standard
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Safety Information:
Preferred SDS: View
 
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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: herbicides / pesticides
Recommendation for metaflumizone usage levels up to:
 not for fragrance use.
 
Recommendation for metaflumizone flavor usage levels up to:
 not for flavor use.
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Safety References:
European Food Safety Authority (EFSA) reference(s):
Reasoned opinion on the modification of the existing MRLs for metaflumizone in various commodities
View page or View pdf
Conclusion on the peer review of the pesticide risk assessment of the active substance metaflumizone
View page or View pdf
Review of the existing maximum residue levels for metaflumizone 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 : 11614934
National Institute of Allergy and Infectious Diseases: Data
 1-[(E)-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]amino]-3-[4-(trifluoromethoxy)phenyl]urea
Chemidplus: 0139968493
RTECS: MV1576452 for cas# 139968-49-3
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References:
 1-[(E)-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]amino]-3-[4-(trifluoromethoxy)phenyl]urea
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 11614934
Pubchem (sid): 135215171
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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
CHEMBL: View
HMDB (The Human Metabolome Database): Search
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 not found in nature
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Synonyms:
 alverde
1-[(E)-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]amino]-3-[4-(trifluoromethoxy)phenyl]urea
(2E)-2-{2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene}-N-[4-(trifluoromethoxy)phenyl]hydrazinecarboxamide
 hydrazinecarboxamide, 2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(trifluoromethoxy)phenyl]-, (2E)-
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Articles:
PubMed: Resistance in Cnaphalocrocis medinalis (Lepidoptera: Pyralidae) to new chemistry insecticides.
PubMed: Methemoglobinemia associated with metaflumizone poisoning.
PubMed: Efficacy of a topical application of Certifect(®) (fipronil 6.26% w/v, amitraz 7.48% w/v, (S)-methoprene 5.63% w/v) for the treatment of canine generalized demodicosis.
PubMed: Lethal and behavioral effects of pesticides on the insect predator Macrolophus pygmaeus.
PubMed: Indoxacarb, Metaflumizone, and Other Sodium Channel Inhibitor Insecticides: Mechanism and Site of Action on Mammalian Voltage-Gated Sodium Channels.
PubMed: Baseline toxicity of metaflumizone and lack of cross resistance between indoxacarb and metaflumizone in diamondback moth (Lepidoptera: Plutellidae).
PubMed: Toxicity of insecticides to populations of tomato borer Tuta absoluta (Meyrick) from Greece.
PubMed: Neuroactive insecticides: targets, selectivity, resistance, and secondary effects.
PubMed: Persistence of metaflumizone on cabbage (Brassica oleracea Linne) and soil, and its risk assessment.
PubMed: Degradation of metaflumizone in soil: impact of varying moisture, light, temperature, atmospheric CO2 level, soil type and soil sterilization.
PubMed: Degradation of metaflumizone in rice, water and soil under field conditions.
PubMed: Compound-specific effects of mutations at Val787 in DII-S6 of Nav 1.4 sodium channels on the action of sodium channel inhibitor insecticides.
PubMed: Efficacy of commercial baits and new active ingredients against firebrats and silverfish (Zygentoma: Lepismatidae).
PubMed: Baseline toxicity and field efficacy of metaflumizone on Colorado potato beetle (Coleoptera: Chrysomelidae).
PubMed: Using organic-certified rather than synthetic pesticides may not be safer for biological control agents: selectivity and side effects of 14 pesticides on the predator Orius laevigatus.
PubMed: Role of the local anesthetic receptor in the state-dependent inhibition of voltage-gated sodium channels by the insecticide metaflumizone.
PubMed: Discovery and development of veterinary antiparasitic drugs: past, present and future.
PubMed: Metaflumizone-amitraz (Promeris)-associated pustular acantholytic dermatitis in 22 dogs: evidence suggests contact drug-triggered pemphigus foliaceus.
PubMed: Comparative acaricidal efficacy of the topically applied combinations fipronil/(S)-methoprene, permethrin/imidacloprid and metaflumizone/ amitraz against Dermacentor reticulatus, the European dog tick (ornate dog tick, Fabricius, 1794) in dogs.
PubMed: Effect of reduced risk pesticides on greenhouse vegetable arthropod biological control agents.
PubMed: Analysis of the action of lidocaine on insect sodium channels.
PubMed: Field and laboratory trials of a novel metaflumizone house fly (Diptera: Muscidae) bait in California.
PubMed: Determination of metaflumizone residues in cabbage and soil using ultra-performance liquid chromatography/ESI-MS/MS.
PubMed: Effect of reduced risk pesticides for use in greenhouse vegetable production on Bombus impatiens (Hymenoptera: Apidae).
PubMed: Evaluation of the potential for interaction between a metaflumizone-amitraz combination and dexmedetomidine hydrochloride in dogs.
PubMed: Efficacy of fipronil-(S)-methoprene, metaflumizone combined with amitraz, and pyriprole commercial spot-on products in preventing Culex pipiens pipiens from feeding on dogs.
PubMed: Evaluation of metaflumizone granular fly bait for management of houseflies.
PubMed: Feeding cessation effects of chlorantraniliprole, a new anthranilic diamide insecticide, in comparison with several insecticides in distinct chemical classes and mode-of-action groups.
PubMed: Role of the sixth transmembrane segment of domain IV of the cockroach sodium channel in the action of sodium channel blocker insecticides.
PubMed: Efficacy of Amitraz plus Metaflumizone for the treatment of canine demodicosis associated with Malassezia pachydermatis.
PubMed: Comparative efficacy of imidacloprid, selamectin, fipronil-(S)-methoprene, and metaflumizone against cats experimentally infested with Ctenocephalides felis.
PubMed: A comparative evaluation of the speed of kill and duration of efficacy against weekly infestations with fleas on cats treated with fipronil-(S)-methoprene or metaflumizone.
PubMed: The effectiveness of a pyriprole (125 mg/ml) and a metaflumizone (150 mg/ml) combined with amitraz (150 mg/ml) spot-on treatment in preventing Phlebotomus perniciosus from feeding on dogs.
PubMed: Efficacy of a topically applied spot-on formulation of a novel insecticide, metaflumizone, applied to cats against a flea strain (KS1) with documented reduced susceptibility to various insecticides.
PubMed: Discovery of metaflumizone, a novel semicarbazone insecticide.
PubMed: Metaflumizone: a novel insecticide for application in animal health. Proceedings of the Fort Dodge Animal Health Global Roundtable, October 2006, Coral Gables, Florida, USA and the symposium of the World Association for the Advancement of Veterinary Parasitology, August 2007, Ghent, Belgium.
PubMed: Metaflumizone is a novel sodium channel blocker insecticide.
PubMed: Topical formulations of metaflumizone plus amitraz to treat flea and tick infestations on dogs.
PubMed: Pharmacokinetics of metaflumizone and amitraz in the plasma and hair of dogs following topical application.
PubMed: Toxicological properties of metaflumizone.
PubMed: Efficacy of a novel formulation of metaflumizone plus amitraz for the treatment of sarcoptic mange in dogs.
PubMed: Evaluation of the efficacy and safety of a novel formulation of metaflumizone plus amitraz in dogs naturally infested with fleas and ticks in Europe.
PubMed: Evaluation of the efficacy and safety of a novel formulation of metaflumizone in cats naturally infested with fleas in Europe.
PubMed: Efficacy of a novel formulation of metaflumizone for the control of fleas (Ctenocephalides felis) on cats.
PubMed: Dose determination of a novel formulation of metaflumizone plus amitraz for control of cat fleas (Ctenocephalides felis felis) and brown dog ticks (Rhipicephalus sanguineus) on dogs.
PubMed: Safety of a topically applied metaflumizone spot-on formulation for flea control in cats and kittens.
PubMed: Safety of a topically applied spot-on formulation of metaflumizone plus amitraz for flea and tick control in dogs.
PubMed: Efficacy of a novel formulation of metaflumizone plus amitraz for the treatment of demodectic mange in dogs.
PubMed: Confirmation of the efficacy of a novel formulation of metaflumizone plus amitraz for the treatment and control of fleas and ticks on dogs.
PubMed: Efficacy of a topically applied formulation of metaflumizone on cats against the adult cat flea, flea egg production and hatch, and adult flea emergence.
PubMed: Pharmacokinetics of metaflumizone in the plasma and hair of cats following topical application.
PubMed: Biology and control of the raspberry crown borer (Lepidoptera: Sesiidae).
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