Metaflumizone | CAS#139968-49-3 | insecticide

MedKoo Cat#: 592742 | Name: Metaflumizone

Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Metaflumizone is an insecticide

Chemical Structure

Metaflumizone

CAS#139968-49-3

Theoretical Analysis

MedKoo Cat#: 592742

Name: Metaflumizone

CAS#: 139968-49-3

Chemical Formula: C24H16F6N4O2

Exact Mass: 506.1177

Molecular Weight: 506.41

Elemental Analysis: C, 56.92; H, 3.18; F, 22.51; N, 11.06; O, 6.32

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 285.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Metaflumizone; BAS 320001; BAS 320021; BASF 320

IUPAC/Chemical Name

2-(2-(4-cyanophenyl)-1-(3-(trifluoromethyl)phenyl)ethylidene)-N-(4-(trifluoromethoxy)phenyl)hydrazinecarboxamide

InChi Key

MIFOMMKAVSCNKQ-HWIUFGAZSA-N

InChi Code

InChI=1S/C24H16F6N4O2/c25-23(26,27)18-3-1-2-17(13-18)21(12-15-4-6-16(14-31)7-5-15)33-34-22(35)32-19-8-10-20(11-9-19)36-24(28,29)30/h1-11,13H,12H2,(H2,32,34,35)/b33-21-

SMILES Code

FC(C1=CC(/C(CC2=CC=C(C#N)C=C2)=N\NC(NC3=CC=C(OC(F)(F)F)C=C3)=O)=CC=C1)(F)F

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Metaflumizone is a semicarbazone insecticide, acts as a potent sodium channel blocker.

In vitro activity:

Studies on native sodium channels, in primary-cultured neurons isolated from the CNS of the larvae of the moth Manduca sexta and on Para/TipE sodium channels heterologously expressed in Xenopus (African clawed frog) oocytes, confirmed that metaflumizone blocks sodium channels by binding selectively to the slow-inactivated state, which is characteristic of the SCBIs. The results confirm that metaflumizone is a novel sodium channel blocker insecticide. Reference: Vet Parasitol. 2007 Dec 15;150(3):182-9. https://pubmed.ncbi.nlm.nih.gov/17959312/

In vivo activity:

This study used the Xenopus oocyte expression system and a Markovian model to assess the effect of metaflumizone on Apis mellifera Na+ channels (AmNaV 1). Metaflumizone inhibits AmNaV 1 channels by targeting the kinetics of recovery from slow inactivation. Multistate modeling of fast and slow inactivation of the AmNaV 1 channel made it possible to study the effects of metaflumizone on a set of rate constants underlying the transition between the open and inactivated conformations and provided insights into their specificity. Reference: FEBS Lett. 2017 Dec;591(23):3842-3849. https://pubmed.ncbi.nlm.nih.gov/29105054/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	300.0	592.41

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 506.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Chatterjee NS, Gupta S. Persistence of metaflumizone on cabbage (Brassica oleracea Linne) and soil, and its risk assessment. Environ Monit Assess. 2013 Jul;185(7):6201-8. doi: 10.1007/s10661-012-3017-y. Epub 2012 Dec 7. PMID: 23224645. 2. Salgado VL, Hayashi JH. Metaflumizone is a novel sodium channel blocker insecticide. Vet Parasitol. 2007 Dec 15;150(3):182-9. doi: 10.1016/j.vetpar.2007.08.032. Epub 2007 Oct 23. PMID: 17959312. 3. Gosselin-Badaroudine P, Charnet P, Collet C, Chahine M. Metaflumizone inhibits the honeybee NaV 1 channel by targeting recovery from slow inactivation. FEBS Lett. 2017 Dec;591(23):3842-3849. doi: 10.1002/1873-3468.12897. Epub 2017 Nov 12. PMID: 29105054. 4. von Stein RT, Soderlund DM. Role of the local anesthetic receptor in the state-dependent inhibition of voltage-gated sodium channels by the insecticide metaflumizone. Mol Pharmacol. 2012 Mar;81(3):366-74. doi: 10.1124/mol.111.075283. Epub 2011 Nov 29. PMID: 22127519; PMCID: PMC3286292.

In vitro protocol:

In vivo protocol:

1. Gosselin-Badaroudine P, Charnet P, Collet C, Chahine M. Metaflumizone inhibits the honeybee NaV 1 channel by targeting recovery from slow inactivation. FEBS Lett. 2017 Dec;591(23):3842-3849. doi: 10.1002/1873-3468.12897. Epub 2017 Nov 12. PMID: 29105054. 2. von Stein RT, Soderlund DM. Role of the local anesthetic receptor in the state-dependent inhibition of voltage-gated sodium channels by the insecticide metaflumizone. Mol Pharmacol. 2012 Mar;81(3):366-74. doi: 10.1124/mol.111.075283. Epub 2011 Nov 29. PMID: 22127519; PMCID: PMC3286292.

1: Tian X, Sun X, Su J. Biochemical mechanisms for metaflumizone resistance in beet armyworm, Spodoptera exigua. Pestic Biochem Physiol. 2014 Jul;113:8-14. doi: 10.1016/j.pestbp.2014.06.010. Epub 2014 Jul 1. PubMed PMID: 25052521. 2: Oh JS, Choi KH. Methemoglobinemia associated with metaflumizone poisoning. Clin Toxicol (Phila). 2014 Apr;52(4):288-90. doi: 10.3109/15563650.2014.900180. Epub 2014 Mar 20. PubMed PMID: 24649894. 3: Li C, Yang T, Wu YL. Degradation of metaflumizone in rice, water and soil under field conditions. Ecotoxicol Environ Saf. 2012 Dec;86:73-8. doi: 10.1016/j.ecoenv.2012.08.029. Epub 2012 Oct 15. PubMed PMID: 23079740. 4: Chatterjee NS, Gupta S. Persistence of metaflumizone on cabbage (Brassica oleracea Linne) and soil, and its risk assessment. Environ Monit Assess. 2013 Jul;185(7):6201-8. doi: 10.1007/s10661-012-3017-y. Epub 2012 Dec 7. PubMed PMID: 23224645. 5: Khakame SK, Wang X, Wu Y. Baseline toxicity of metaflumizone and lack of cross resistance between indoxacarb and metaflumizone in diamondback moth (Lepidoptera: Plutellidae). J Econ Entomol. 2013 Jun;106(3):1423-9. PubMed PMID: 23865210. 6: von Stein RT, Soderlund DM. Role of the local anesthetic receptor in the state-dependent inhibition of voltage-gated sodium channels by the insecticide metaflumizone. Mol Pharmacol. 2012 Mar;81(3):366-74. doi: 10.1124/mol.111.075283. Epub 2011 Nov 29. PubMed PMID: 22127519; PubMed Central PMCID: PMC3286292. 7: Chatterjee NS, Gupta S, Varghese E. Degradation of metaflumizone in soil: impact of varying moisture, light, temperature, atmospheric CO2 level, soil type and soil sterilization. Chemosphere. 2013 Jan;90(2):729-36. doi: 10.1016/j.chemosphere.2012.09.057. Epub 2012 Oct 24. PubMed PMID: 23102725. 8: von Stein RT, Silver KS, Soderlund DM. Indoxacarb, Metaflumizone, and Other Sodium Channel Inhibitor Insecticides: Mechanism and Site of Action on Mammalian Voltage-Gated Sodium Channels. Pestic Biochem Physiol. 2013 Jul 1;106(3):101-112. PubMed PMID: 24072940; PubMed Central PMCID: PMC3780446. 9: Hitchner EM, Kuhar TP, Dively GP, Youngman RR, Philips CR, Anderson TD. Baseline toxicity and field efficacy of metaflumizone on Colorado potato beetle (Coleoptera: Chrysomelidae). J Econ Entomol. 2012 Feb;105(1):207-13. PubMed PMID: 22420273. 10: Wang XL, Su W, Zhang JH, Yang YH, Dong K, Wu YD. Two novel sodium channel mutations associated with resistance to indoxacarb and metaflumizone in the diamondback moth, Plutella xylostella. Insect Sci. 2016 Feb;23(1):50-8. doi: 10.1111/1744-7917.12226. Epub 2015 Jun 3. PubMed PMID: 25850422; PubMed Central PMCID: PMC4598255. 11: Hempel K, Hess FG, Bögi C, Fabian E, Hellwig J, Fegert I. Toxicological properties of metaflumizone. Vet Parasitol. 2007 Dec 15;150(3):190-5. Epub 2007 Oct 22. PubMed PMID: 17933467. 12: DeLay RL, Lacoste E, Delprat S, Blond-Riou F. Pharmacokinetics of metaflumizone in the plasma and hair of cats following topical application. Vet Parasitol. 2007 Dec 15;150(3):258-62. Epub 2007 Oct 29. PubMed PMID: 17913364. 13: DeLay RL, Lacoste E, Mezzasalma T, Blond-Riou F. Pharmacokinetics of metaflumizone and amitraz in the plasma and hair of dogs following topical application. Vet Parasitol. 2007 Dec 15;150(3):251-7. Epub 2007 Oct 17. PubMed PMID: 17942231. 14: Fourie LJ, Kok DJ, du Plessis A, Rugg D. Efficacy of a novel formulation of metaflumizone plus amitraz for the treatment of demodectic mange in dogs. Vet Parasitol. 2007 Dec 15;150(3):268-74. Epub 2007 Oct 17. PubMed PMID: 17923331. 15: Salgado VL, Hayashi JH. Metaflumizone is a novel sodium channel blocker insecticide. Vet Parasitol. 2007 Dec 15;150(3):182-9. Epub 2007 Oct 23. PubMed PMID: 17959312. 16: Oberkirchner U, Linder KE, Dunston S, Bizikova P, Olivry T. Metaflumizone-amitraz (Promeris)-associated pustular acantholytic dermatitis in 22 dogs: evidence suggests contact drug-triggered pemphigus foliaceus. Vet Dermatol. 2011 Oct;22(5):436-48. doi: 10.1111/j.1365-3164.2011.00974.x. Epub 2011 Mar 21. PubMed PMID: 21418349. 17: Dryden M, Payne P, Lowe A, Mailen S, Smith V, Rugg D. Efficacy of a topically applied formulation of metaflumizone on cats against the adult cat flea, flea egg production and hatch, and adult flea emergence. Vet Parasitol. 2007 Dec 15;150(3):263-7. Epub 2007 Oct 4. PubMed PMID: 17919817. 18: Dryden M, Payne P, Lowe A, Mailen S, Smith V, Rugg D. 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. Vet Parasitol. 2008 Jan 25;151(1):74-9. Epub 2007 Oct 10. PubMed PMID: 18022186. 19: Zwijnenberg R, Muir W. Evaluation of the potential for interaction between a metaflumizone-amitraz combination and dexmedetomidine hydrochloride in dogs. Vet Ther. 2009 Spring-Summer;10(1-2):40-5. PubMed PMID: 19742447. 20: Ahmad A, Zurek L. Evaluation of metaflumizone granular fly bait for management of houseflies. Med Vet Entomol. 2009 Jun;23(2):167-9. doi: 10.1111/j.1365-2915.2009.00797.x. PubMed PMID: 19493197.