Benfuracarb | CAS# 82560-54-1 | insecticide

MedKoo Cat#: 573881 | Name: Benfuracarb

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Description:

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

Benfuracarb is a benzofuranyl methylcarbamate based insecticide used to control aphids, springtails and other pests usually on beet crops.

Chemical Structure

Benfuracarb

CAS#82560-54-1

Theoretical Analysis

MedKoo Cat#: 573881

Name: Benfuracarb

CAS#: 82560-54-1

Chemical Formula: C20H30N2O5S

Exact Mass: 410.1875

Molecular Weight: 410.53

Elemental Analysis: C, 58.51; H, 7.37; N, 6.82; O, 19.49; S, 7.81

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 350.00	2 Weeks

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Synonym

Aminofuracarb; Benfuracarb; Furacon; OC-11588; OC11588; OC 11588;

IUPAC/Chemical Name

8-Oxa-3-thia-2,4-diazadecanoic acid, 2-methyl-4-(1-methylethyl)-7-oxo-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester

InChi Key

FYZBOYWSHKHDMT-UHFFFAOYSA-N

InChi Code

1S/C20H30N2O5S/c1-7-25-17(23)11-12-22(14(2)3)28-21(6)19(24)26-16-10-8-9-15-13-20(4,5)27-18(15)16/h8-10,14H,7,11-13H2,1-6H3

SMILES Code

CCOC(=O)CCN(C(C)C)SN(C)C(=O)Oc1cccc2c1OC(C2)(C)C

Appearance

Viscous liquid

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

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Benfuracarb is a benzofuranyl methylcarbamate based insecticide.

In vitro activity:

Human variation and the contributions of human-CYP isoforms to in vitro metabolism of benfuracarb were investigated. The primary metabolic pathways were the initial sulfur oxidation to benfuracarb-sulfoxide and the nitrogen-sulfur bond cleavage to carbofuran (activation). The Km, Vmax, and CL(int) values of carbofuran production in ten individual hepatic samples varied 7.3-, 3.4-, and 5.4-fold, respectively. CYP2C9 and CYP2C19 catalyzed benfuracarb sulphur oxidation. Carbofuran formation, representing from 79% to 98% of the total metabolism, was catalyzed predominantly by CYP3A4. The calculated relative contribution of CYP3A4 to carbofuran formation was 93%, while it was 4.4% for CYP2C9. The major contribution of CYP3A4 in benfuracarb metabolism was further substantiated by showing a strong correlation with CYP3A4-selective markers midazolam-1'-hydroxylation and omeprazole-sulfoxidation (r=0.885 and 0.772, respectively). Carbofuran formation was highly inhibited by the CYP3A inhibitor ketoconazole. Moreover, CYP3A4 marker activities were relatively inhibited by benfuracarb. These results suggest that human CYP3A4 is the major enzyme involved in the in vitro activation of benfuracarb and that CYP3A4-catalyzed metabolism is the primary source of interindividual differences. Reference: Toxicol Lett. 2014 Jan 13;224(2):300-9. https://www.sciencedirect.com/science/article/abs/pii/S0378427413012952?via%3Dihub

In vivo activity:

TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 410.53 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. Abass K, Reponen P, Mattila S, Rautio A, Pelkonen O. Human variation and CYP enzyme contribution in benfuracarb metabolism in human in vitro hepatic models. Toxicol Lett. 2014 Jan 13;224(2):300-9. doi: 10.1016/j.toxlet.2013.08.023. Epub 2013 Sep 7. PMID: 24016712.

In vitro protocol:

In vivo protocol:

TBD

1: Guo S, Wu Y, Xiao P, Li W. Benfuracarb inhibits body growth and causes oxidative stress in zebrafish (Danio rerio). Chemosphere. 2022 Mar;291(Pt 2):132955. doi: 10.1016/j.chemosphere.2021.132955. Epub 2021 Nov 18. PMID: 34801571. 2: Eren Y, Erdoğmuş SF, Akyıl D, Özkara A. Mutagenic and cytotoxic activities of benfuracarb insecticide. Cytotechnology. 2016 Aug;68(4):637-43. doi: 10.1007/s10616-014-9811-3. Epub 2014 Nov 8. PMID: 25381170; PMCID: PMC4960112. 3: Abass K, Reponen P, Mattila S, Rautio A, Pelkonen O. Comparative metabolism of benfuracarb in in vitro mammalian hepatic microsomes model and its implications for chemical risk assessment. Toxicol Lett. 2014 Jan 13;224(2):290-9. doi: 10.1016/j.toxlet.2013.08.009. Epub 2013 Aug 16. PMID: 23958702. 4: Abass K, Reponen P, Mattila S, Rautio A, Pelkonen O. Human variation and CYP enzyme contribution in benfuracarb metabolism in human in vitro hepatic models. Toxicol Lett. 2014 Jan 13;224(2):300-9. doi: 10.1016/j.toxlet.2013.08.023. Epub 2013 Sep 7. PMID: 24016712. 5: Chandra R, Srivastava A, Srivastava PC. Fate of benfuracarb insecticide in mollisols and brinjal crop. Bull Environ Contam Toxicol. 2009 Sep;83(3):348-51. doi: 10.1007/s00128-009-9710-z. Epub 2009 Mar 31. PMID: 19333533. 6: Srivastava A, Chandra R, Srivastava PC. Kinetics of sorption-desorption of benfuracarb insecticide in mollisols. Pest Manag Sci. 2011 Feb;67(2):209-12. doi: 10.1002/ps.2053. PMID: 21072780. 7: Ichikawa S, Goto T, Umetsu N. Antidotal action of atropine sulfate against insecticide benfuracarb poisoning in rats. J Toxicol Sci. 1995 May;20(2):143-8. doi: 10.2131/jts.20.143. PMID: 7473892. 8: Yi JH, Perumalsamy H, Sankarapandian K, Choi BR, Ahn YJ. Fumigant Toxicity of Phenylpropanoids Identified in Asarum sieboldii Aerial Parts to Lycoriella ingenua (Diptera: Sciaridae) and Coboldia fuscipes (Diptera: Scatopsidae). J Econ Entomol. 2015 Jun;108(3):1208-14. doi: 10.1093/jee/tov064. Epub 2015 Apr 4. PMID: 26470247. 9: Maiza A, Kilani S, Farine JP, Smagghe G, Aribi N, Soltani N. Reproductive effects in German cockroaches by ecdysteroid agonist RH-0345, juvenile hormone analogue methoprene and carbamate benfuracarb. Commun Agric Appl Biol Sci. 2004;69(3):257-66. PMID: 15759422. 10: Fukazawa T, Kobayashi T, Tokairin S, Chimi K, Maruyama T, Yanagita T. [Behavior of N-methylcarbamate pesticides during refinement processing of edible oils]. J Oleo Sci. 2007;56(2):65-71. Japanese. doi: 10.5650/jos.56.65. PMID: 17898465. 11: Xue N, Yang R, Xu X, Seip HM, Zeng Q. Adsorption and degradation of benfuracarb in three soils in Hunan, People's Republic of China. Bull Environ Contam Toxicol. 2006 Apr;76(4):720-7. doi: 10.1007/s00128-006-0979-x. Erratum in: Bull Environ Contam Toxicol. 2006 Aug;77(2):319. Zang, Q [corrected to Zeng, Q]. PMID: 16688558. 12: Kilani-Morakchi S, Aribi N, Farine JP, Smagghe G, Soltani N. Cuticular hydrocarbon profiles in Blattella germanica: effects of halofenozide, boric acid and benfuracarb. Commun Agric Appl Biol Sci. 2006;71(2 Pt B):555-62. PMID: 17385524. 13: Iesce MR, della Greca M, Cermolal F, Rubino M, Isidori M, Pascarella L. Transformation and ecotoxicity of carbamic pesticides in water. Environ Sci Pollut Res Int. 2006 Mar;13(2):105-9. doi: 10.1065/espr2005.10.285. PMID: 16612899. 14: Stehrer-Schmid P, Wolf HU. Effects of benzofuran and seven benzofuran derivatives including four carbamate insecticides in the in vitro porcine brain tubulin assembly assay and description of a new approach for the evaluation of the test data. Mutat Res. 1995 Feb;339(1):61-72. doi: 10.1016/0165-1110(94)00015-5. PMID: 7877645. 15: Lee SK, Ameno K, Yang JY, In SW, Kim KU, Kwon TJ, Yoo YC, Kubota T, Ameno S, Ijiri I. Forensic toxicological implication of acute fatal poisoning cases due to benfuracarb ingestion. Int J Legal Med. 1999;112(4):268-70. doi: 10.1007/s004140050247. PMID: 10433038. 16: Wu Y, Fan Q, Chen Y, Sun X, Shi G. Production and Selection of Antibody- Antigen Pairs for the Development of Immunoenzyme Assay and Lateral Flow Immunoassay Methods for Carbofuran and Its Analogues. Biosensors (Basel). 2022 Jul 24;12(8):560. doi: 10.3390/bios12080560. PMID: 35892457; PMCID: PMC9332470. 17: Stehrer-Schmid P, Wolf HU. Genotoxic evaluation of three heterocyclic N-methylcarbamate pesticides using the mouse bone marrow micronucleus assay and the Saccharomyces cerevisiae strains D7 and D61.M. Mutat Res. 1995 Dec;345(3-4):111-25. doi: 10.1016/0165-1218(95)90047-0. PMID: 8552133. 18: Ohno Y, Miyajima A, Sunouchi M. Alternative methods for mechanistic studies in toxicology. Screening of hepatotoxicity of pesticides using freshly isolated and primary cultured hepatocytes and non-liver-derived cells, SIRC cells. Toxicol Lett. 1998 Dec 28;102-103:569-73. doi: 10.1016/s0378-4274(98)00250-1. PMID: 10022315. 19: Jacobs MN, Kubickova B, Boshoff E. Candidate Proficiency Test Chemicals to Address Industrial Chemical Applicability Domains for in vitro Human Cytochrome P450 Enzyme Induction. Front Toxicol. 2022 Jun 20;4:880818. doi: 10.3389/ftox.2022.880818. PMID: 35795225; PMCID: PMC9252529. 20: de Souza TA, Rodrigues GCS, de Souza PHN, Abreu LS, Pereira LCO, da Silva MS, Tavares JF, Scotti L, Scotti MT. Mass Spectrometry-Based Investigation of Sugarcane Exposed to Five Different Pesticides. Life (Basel). 2023 Apr 17;13(4):1034. doi: 10.3390/life13041034. PMID: 37109563; PMCID: PMC10145413.