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Fungicides
Iron tris(dimethyldithiocarbamate)
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Iron tris(dimethyldithiocarbamate)

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Iron tris(dimethyldithiocarbamate)
Ferbam.svg
DMTCFE01Fe(dtc)3tight.png
Names
IUPAC name
Tris(dimethyldithiocarbamato)iron
Other names
Ferric dimethyl dithiocarbamate, Ferbam
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.034.970
EC Number
  • 238-484-2
KEGG
PubChem CID
RTECS number
  • NO8750000
UNII
UN number 3077, 2771
  • InChI=1S/3C3H7NS2.Fe/c3*1-4(2)3(5)6;/h3*1-2H3,(H,5,6);/q;;;+3/p-3
    Key: WHDGWKAJBYRJJL-UHFFFAOYSA-K
  • coordination form: CN(C)C(S1)S[Fe]123(SC(S2)N(C)C)SC(S3)N(C)C
  • ionic form: CN(C)c(=s)[s-].[Fe+3].CN(C)c(=s)[s-].CN(C)c(=s)[s-]
Properties
[(CH3)2NCS2]3Fe
Molar mass 416.5 g/mol
Appearance Dark brown to black, odorless solid
Density 1.52 g/cm3
Melting point Decomposes above 180 °C (356 °F)
Boiling point Decomposes
0.01% (20 °C)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Reacts with strong oxidizers, moisture
Lethal dose or concentration (LD, LC):
3000 mg/kg (rabbit, oral)
2000 mg/kg (guinea pig, oral)
1130 mg/kg (rat, oral)
3400 mg/kg (mouse, oral)
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 15 mg/m3
REL (Recommended)
 TWA 10 mg/m3
IDLH (Immediate danger)
 800 mg/m3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Iron tris(dimethyldithiocarbamate) is the coordination complex of iron with dimethyldithiocarbamate with the formula Fe(S2CNMe2)3 (Me = methyl). It is marketed as a fungicide.

Synthesis, structure, bonding

Iron tris(dithiocarbamate)s are typically are prepared by salt metathesis reactions.

Iron tris(dimethyldithiocarbamate) is an octahedral coordination complex of iron(III) with D3symmetry.

Spin crossover (SCO) was first observed in 1931 by Cambi et al. who discovered anomalous magnetic behavior for the tris(N,N-dialkyldithiocarbamatoiron(III) complexes. The spin states of these complexes are sensitive to the nature of the amine substituents.

Reactions

Iron tris(dithiocarbamate)s react with nitric oxide to give a nitrosyl complex:

Fe(dtc)3 + NO → Fe(dtc)2NO + 0.5 (dtc)2

This efficient chemical trapping reaction provides a means to detect NO.

Reflecting the strongly donating properties of dithiocarbamate ligands, iron tris(dithiocarbamate)s oxidize at relatively mild potentials to give isolable iron(IV) derivatives [Fe(S2CNR2)3]+.

Iron tris(dithiocarbamate)s react with hydrochloric acid to give the pentacoordinate chloride:

Fe(dtc)3 + HCl → Fe(dtc)2Cl + Hdtc

Safety

The U.S. Occupational Safety and Health Administration (OSHA) has set the legal (permissible exposure limit) for ferbam exposure in the workplace as 15 mg/m3 over an 8-hour workday. The U.S. National Institute for Occupational Safety and Health (NIOSH) has set a recommended exposure limit (REL) of 1 mg/m3 over an 8-hour workday. At levels of 800 mg/m3, ferbam is immediately dangerous to life and health.

See also


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