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MedKoo Cat#: 592763 | Name: Metiram

Description:

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

Metiram is a polymeric dithiocarbamic fungicide used in agriculture. Metiram is present as a mixture rather than a complex and is not assigned an ISO name. Metiram is used commonly in the protection of grapevines, apples, tomatoes, potatoes as well as other crops.

Chemical Structure

Metiram
Metiram
CAS#9006-42-2

Theoretical Analysis

MedKoo Cat#: 592763

Name: Metiram

CAS#: 9006-42-2

Chemical Formula: C4H6N2S4Zn

Exact Mass: 273.8705

Molecular Weight: 275.73

Elemental Analysis: C, 17.42; H, 2.19; N, 10.16; S, 46.51; Zn, 23.71

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Synonym
Metiram; NIA 9102; NIA-9102; NIA9102
IUPAC/Chemical Name
Zinc ammoniate ethylenebis(dithiocarbamate)-poly(ethylenethiuram disulfide)
InChi Key
AMHNZOICSMBGDH-UHFFFAOYSA-L
InChi Code
InChI=1S/C4H8N2S4.Zn/c7-3(8)5-1-2-6-4(9)10;/h1-2H2,(H2,5,7,8)(H2,6,9,10);/q;+2/p-2
SMILES Code
[S-]C(NCCNC([S-])=S)=S.[Zn+2]
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:
Metiram is a polymeric dithiocarbamic fungicide used in agriculture.
In vitro activity:
Metiram (Polyram 700 WG) was highly toxic to E. victoriensis but only moderately toxic to G. occidentalis. Reference: J Econ Entomol. 2004 Jun;97(3):891-9. https://pubmed.ncbi.nlm.nih.gov/15279268/
In vivo activity:
The present study was designed to estimate the effect of aqueous extract of licorice on metiram toxicity in mice. Treating mice with metiram at a dose level of [1/2] LD(50) daily for 3 weeks induced many histological changes in the kidney cortex. The renal tubules lost their characteristic appearance and their lining epithelial cells were degenerated. The glomeruli were atrophied and the renal blood vessels were congested. The intertubular spaces infiltrated by inflammatory leukocytic cells. Metiram caused an increase in proliferating cell nuclear antigen (PCNA) expression in nuclei of tubular epithelial cells. Metiram also caused marked elevation in serum creatinine and blood urea nitrogen. Reference: Environ Toxicol. 2013 Jul;28(7):372-9. https://pubmed.ncbi.nlm.nih.gov/21544926/

Preparing Stock Solutions

The following data is based on the product molecular weight 275.73 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.

Recalculate based on batch purity %
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. Sakr S, El-Kenawy A, El-Sahra D. Metiram-induced nephrotoxicity in albino mice: effect of licorice aqueous extract. Environ Toxicol. 2013 Jul;28(7):372-9. doi: 10.1002/tox.20728. Epub 2011 May 4. PMID: 21544926. 2. Bernard MB, Horne PA, Hoffmann AA. Developing an ecotoxicological testing standard for predatory mites in Australia: acute and sublethal effects of fungicides on Euseius victoriensis and Galendromus occidentalis (Acarina: Phytoseiidae). J Econ Entomol. 2004 Jun;97(3):891-9. doi: 10.1093/jee/97.3.891. PMID: 15279268.
In vitro protocol:
1. Bernard MB, Horne PA, Hoffmann AA. Developing an ecotoxicological testing standard for predatory mites in Australia: acute and sublethal effects of fungicides on Euseius victoriensis and Galendromus occidentalis (Acarina: Phytoseiidae). J Econ Entomol. 2004 Jun;97(3):891-9. doi: 10.1093/jee/97.3.891. PMID: 15279268.
In vivo protocol:
1. Sakr S, El-Kenawy A, El-Sahra D. Metiram-induced nephrotoxicity in albino mice: effect of licorice aqueous extract. Environ Toxicol. 2013 Jul;28(7):372-9. doi: 10.1002/tox.20728. Epub 2011 May 4. PMID: 21544926.
1: Sakr S, El-Kenawy A, El-Sahra D. Metiram-induced nephrotoxicity in albino mice: effect of licorice aqueous extract. Environ Toxicol. 2013 Jul;28(7):372-9. doi: 10.1002/tox.20728. Epub 2011 May 4. PubMed PMID: 21544926. 2: Lin R, Buijse L, Dimitrov MR, Dohmen P, Kosol S, Maltby L, Roessink I, Sinkeldam JA, Smidt H, Van Wijngaarden RP, Brock TC. Effects of the fungicide metiram in outdoor freshwater microcosms: responses of invertebrates, primary producers and microbes. Ecotoxicology. 2012 Jul;21(5):1550-69. doi: 10.1007/s10646-012-0909-0. Epub 2012 May 4. PubMed PMID: 22555811; PubMed Central PMCID: PMC3377896. 3: Shabeer T P A, Girame R, Hingmire S, Banerjee K, Sharma AK, Oulkar D, Utture S, Jadhav M. Dissipation pattern, safety evaluation, and generation of processing factor (PF) for pyraclostrobin and metiram residues in grapes during raisin preparation. Environ Monit Assess. 2015 Feb;187(2):31. doi: 10.1007/s10661-015-4268-1. Epub 2015 Jan 30. PubMed PMID: 25632901. 4: Charles JM, Tobia A, van Ravenzwaay B. Subchronic and chronic toxicological investigations on metiram: the lack of a carcinogenic response in rodents. Toxicol Sci. 2000 Apr;54(2):481-92. PubMed PMID: 10774831. 5: Liebenow W, Weber E, Schmidt B. [Attempted suicide with Metiram, a fungicide similar to Antabuse]. Munch Med Wochenschr. 1968 May 17;110(20):1238-41. German. PubMed PMID: 5755972. 6: Whalen MM, Loganathan BG, Yamashita N, Saito T. Immunomodulation of human natural killer cell cytotoxic function by triazine and carbamate pesticides. Chem Biol Interact. 2003 Jun 15;145(3):311-9. PubMed PMID: 12732457. 7: Qin S, Qiao X, Wang X, Zhao L. [Determination of 4 dithiocarbamate residues in 22 matrices by gas chromatography]. Se Pu. 2010 Dec;28(12):1162-7. Chinese. PubMed PMID: 21438370. 8: Celar FA, Kos K. Effects of selected herbicides and fungicides on growth, sporulation and conidial germination of entomopathogenic fungus Beauveria bassiana. Pest Manag Sci. 2016 Nov;72(11):2110-2117. doi: 10.1002/ps.4240. Epub 2016 Feb 29. PubMed PMID: 26817532. 9: Vavrinevych OP, Omel'chuk ST, Bardov VH. [Comparative hygienic assessment of potential risk to workers under application of fungicides of different classes]. Lik Sprava. 2014 Mar-Apr;(3-4):130-8. Ukrainian. PubMed PMID: 25286613. 10: Koch P. Occupational allergic contact dermatitis and airborne contact dermatitis from 5 fungicides in a vineyard worker. Cross-reactions between fungicides of the dithiocarbamate group? Contact Dermatitis. 1996 May;34(5):324-9. PubMed PMID: 8807224. 11: Itako AT, Tolentino Júnior JB, Silva Júnior TA, Soman JM, Maringoni AC. Chemical products induce resistance to Xanthomonas perforans in tomato. Braz J Microbiol. 2015 Jul 1;46(3):701-6. doi: 10.1590/S1517-838246320140177. eCollection 2015 Jul-Sep. PubMed PMID: 26413050; PubMed Central PMCID: PMC4568868. 12: Schmidt B, Christensen HB, Petersen A, Sloth JJ, Poulsen ME. Method validation and analysis of nine dithiocarbamates in fruits and vegetables by LC-MS/MS. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2013;30(7):1287-98. doi: 10.1080/19440049.2013.801083. Epub 2013 Jun 25. PubMed PMID: 23799268. 13: Kornuta N, Bagley E, Nedopitanskaya N. Genotoxic effects of pesticides. J Environ Pathol Toxicol Oncol. 1996;15(2-4):75-8. PubMed PMID: 9216788. 14: Abdel-Fattah HM, Abdel-Kader MI, Hamida S. Selective effects of two systemic fungicides on soil fungi. Mycopathologia. 1982 Aug 20;79(2):93-9. PubMed PMID: 6290890. 15: Bonnemain H, Dive D. Studies on synergistic toxic effects of copper and dithiocarbamate pesticides with the ciliate protozoan Colpidium campylum (Stokes). Ecotoxicol Environ Saf. 1990 Jun;19(3):320-6. PubMed PMID: 2114279. 16: Vettorazzi G, Almeida WF, Burin GJ, Jaeger RB, Puga FR, Rahde AF, Reyes FG, Schvartsman S. International safety assessment of pesticides: dithiocarbamate pesticides, ETU, and PTU--a review and update. Teratog Carcinog Mutagen. 1995-1996;15(6):313-37. Review. PubMed PMID: 8732882. 17: Grimaĭlo LV, Ermolova RS. [The potential for using an integrated method of soil disinfection in microfoci of geohelminthiases]. Med Parazitol (Mosk). 1993 May-Jun;(3):23-5. Russian. PubMed PMID: 8041311. 18: Gzhegotskiĭ MI, Kuz'minov BP, Kokot VR, Zhuk SSh. [Toxicologic characteristics of combined pesticides on the base polycarbacin]. Gig Tr Prof Zabol. 1987 Aug;(8):51-2. Russian. PubMed PMID: 2824299. 19: Brochinskiĭ KK, Martson' VS. [Determination of maximum permissible concentration of polycarbacide in the water reservoirs]. Gig Sanit. 1980 Nov;(11):76-7. Russian. PubMed PMID: 6254857. 20: Tkach VE. [Effect of polycarbacin on the skin and mucous membranes]. Vestn Dermatol Venerol. 1985 Oct;(10):58-61. Russian. PubMed PMID: 3002064.

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Clidafidine (free base)

Clidafidine (free base)