14484-64-1

Basic information

• Product Name: FERBAM
• Synonyms: CARBAMATE(R);FERBAM;FERBAM GRANUFLO;FERBERK;FERBERK(R);FERMATE;FERMATE(R);FERRADOW(R)
• CAS NO: 14484-64-1
• Molecular Formula: 3C₃H₆NS₂*Fe
• Molecular Weight: 416.49
• EINECS: 238-484-2
• Product Categories: Organometallics;Classes of Metal Compounds;Fe (Iron) Compounds;Transition Metal Compounds
• Mol File: 14484-64-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 180°C (dec.)
• Boiling Point: 129.4 °C at 760 mmHg
• Flash Point: 32 °C
• Appearance: /solid
• Density: 0.21[at 20℃]
• Vapor Pressure: 2 x 10-11 Pa (est.)
• Storage Temp.: 0-6°C
• Water Solubility: 130 mg l-1 (room temperature)
• Stability: Stable. Incompatible with strong oxidants.
• Merck: 14,4013
• CAS DataBase Reference: FERBAM(CAS DataBase Reference)
• NIST Chemistry Reference: FERBAM(14484-64-1)
• EPA Substance Registry System: FERBAM(14484-64-1)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36/37/38-50/53
• Safety Statements: 26-36/37/39-61-60
• RIDADR: UN3077 9/PG 3
• RTECS: NO8750000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 14484-64-1(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 14484-64-1 differently. You can refer to the following data:
1. odourless black solid
2. Ferbam is a combustible, odorless dark brown to black powder or granular solid

Uses

Different sources of media describe the Uses of 14484-64-1 differently. You can refer to the following data:
1. Nonphytotoxic fungicide used to control scab on fruits and other crops.
2. Ferbam is a protective fungicide applied to foliage to control scab on pome fruit, peach leaf curl, blue mould on tobacco and other diseases on many other crops. It is often used in combinations with other dithiocarbamates to extend the spectrum of activity.
3. Fruit fungicide.

Definition

A wettable powder containing 76% ferbam.

General Description

Ferbam is a carbamate fungicide. It is a stable, black powder and combustible and gives off irritating or toxic fumes (or gases) in a fire. Ferbam is incompatible with strong oxidants. It is used for foliar protectant against scab, rust, mould, and many fungal diseases on fruits, vegetables, melons, and ornamentals. Also, it works as a repellent towards Japanese beetles. The major uses of ferbam are in the control of apple scab and cedar apple rust, peach leaf curl, tobacco blue mould, and cranberry diseases. Ferbam is a broad-spectrum registered fungicide for the control of certain diseases in fruit trees, small fruit and berry crops, potatoes, ornamentals, conifers, and tobacco and for use on citrus, pome, stone fruits, and cranberries. Major areas of use include Florida, Massachusetts, New Jersey, and other countries. Ferbam is used as water-dispersible granule, 76WG.

Air & Water Reactions

Thio and dithiocarbamates slowly decompose in aqueous solution to form carbon disulfide and methylamine or other amines. Such decompositions are accelerated by acids.

Reactivity Profile

FERBAM is a dithiocarbamate. Flammable gases are generated by the combination of thiocarbamates and dithiocarbamates with aldehydes, nitrides, and hydrides. Thiocarbamates and dithiocarbamates are incompatible with acids, peroxides, and acid halides.

Hazard

Irritant to eyes and mucous membranes. Questionable carcinogen.

Health Hazard

Ferbam is an irritant of the eyes and respiratory tract; in animals it causes central nervous system depression, and it is expected that severe exposure will cause the same effect in humans.

Flammability and Explosibility

Notclassified

Agricultural Uses

Fungicide: Registered for use in the U.S. and Canada. Not approved for use in EU countries. A dimethyl-dithiocarbamate fungicide. It is widely used, together with other fungicides, to control Postbloom Fruit Drop (PFD) on citrus crops, and as a foliar protectant against scab, rust, mold and many fungus disease on fruits, vegetables, melons and ornamentals. It is registered in several states for use on currents and gooseberries to control leaf spot disease, and on apple, crabapple, hawthorn and quince to control cedar-apple rust disease. It is used to control rust disease on shrubs and ornamentals.

Trade name

AI3-14689?; AAFERTIS?; APPLE DUST No. 1?[C]; BERCEMA FERTAM 50?; CASWELL No. 458?; FERBAM 50?; FERBECK?; FERMATE FERBAM FUNGICIDE?[C]; FERMOCIDE?; FERRADOUR?; FERRADOW?; FUKLASIN ULTRA?; HEXAFERB?; HOKMATE?; KARBAM BLACK?; KARBAM CARBAMATE?; KNOCKMATE?; NIACIDE?; STAUFFER FERBAM?; SUP’R-FLO FERBAM FLOWABLE?; TRICARBAMIX?[C]; TRIFUNGOL?; VANCIDE FE95?[C]

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental carcinogenic and tumorigenic data. Mutation data reported. A fungicide. When heated to decomposition it emits very toxic fumes of NOx and SOx. See also CARBAiMATES.

Potential Exposure

A dithiocarbamate. A potential danger to those involved in the production, formulation and application of this dithiocarbamate; used as a fungicide, rubber accelerator, and plastics prodegradant. Some dithiocarbamates have been used as rubber components

Environmental Fate

Plant. Decomposes in plants to ethylene thiourea, ethylene thiuram monosul?de, ethylene thiuram disul?de and sulfur (Hartley and Kidd, 1987).Chemical/Physical. Hydrolyzes in acidic media releasing carbon disul?de. Decomposes in water forming ethylene thiourea (Hartley and Kidd, 1987).Decomposes >180°C (Windholz et al., 1983) emitting toxic fumes of nitrogen and sulfur oxides (Lewis, 1990; Sax and Lewis, 1987).

Metabolic pathway

Ferbam generates dimethyldithiocarbamic acid by being cleaved in acidic conditions and in biological media. The acid is conjugated with glucose and alanine in plants and with glucuronic acid in mammals. Dimethyldithiocarbamic acid is further degraded to dimethylamine and CS2. An extensive review of the properties of the dithiocarbamate pesticides was published by the World Health Organisation (WHO, 1988) from which much of the following information is taken.

Shipping

UN2771 Dithiocarbamate and Thiocarbamate pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required

Degradation

Ferbam is hydrolysed in acidic media forming dimethyldithiocarbamic acid (2) that in turn decomposes to liberate carbon disulfide (PM) (see Scheme 1).

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine,bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Heat alkalies (lime); moisture can cause decomposition. Decomposes on prolonged storage. Dithiocarbamate esters are combustible. They react violently with powerful oxidizers such as calcium hypochlorite. Poisonous gases are generated by the thermal decomposition of Dithiocarbamate compounds, including carbon disulfide, oxides of sulfur, oxides of nitrogen, hydrogen sulfide, ammonia, and methylamine. Thio and dithiocarbamates slowly decompose in aqueous solution to form carbon disulfide and methylamine or other amines. Such decompositions are accelerated by acids. Flammable gases are generated by the combination of dithiocarbamate with aldehydes, nitrides, and hydrides. Dithiocarbamate are incompatible with acids, peroxides, and acid halides.

Waste Disposal

Ferbam is hydrolyzed by alkali and is unstable to moisture, lime and heat. Ferbam can be incinerated. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal

InChI:InChI=1/3C3H7NS2.Fe/c3*1-4(2)3(5)6;/h3*1-2H3,(H,5,6);/q;;;+3/p-3/rC9H18FeN3S6/c1-11(2)7(14)17-10(18-8(15)12(3)4)19-9(16)13(5)6/h1-6H3

Synthetic route

Fe(diethyldithiocarbamate)2SCN + sodium dimethyldithiocarbamate (128-04-1) → tris(N,N-dimethyldithiocarbamato)iron(III) (14484-64-1)

Conditions	Yield
In chloroform; acetone mixing of Fe-complex (in CHCl3) with excess of Na2S2CNEt2 (in acetone); concn. (vac.), crystn. on EtOH addn., filtration, washing (EtOH);

iron(III) + sodium dimethyldithiocarbamate (128-04-1) → tris(N,N-dimethyldithiocarbamato)iron(III) (14484-64-1)

Conditions	Yield
In water iron(III) salt;;

tris(diethyldithiocarbamato)iron(III) + sodium dimethyldithiocarbamate (128-04-1) → tris(N,N-dimethyldithiocarbamato)iron(III) (14484-64-1)

Conditions	Yield
In acetone addn. of excess NaS2CNMe2 to Fe-complex, stirring (room temp., 30 min); concn. (vac.), addn. of EtOH, concn. (vac., crystn.), filtration, washing (EtOH, acetone); elem. anal.;

iron(II) (7439-89-6) + sodium dimethyldithiocarbamate (128-04-1) → tris(N,N-dimethyldithiocarbamato)iron(III) (14484-64-1)

Conditions	Yield
In water iron(II) salt;;

chlorobis(N,N-diethyldithiocarbamato)iron(III) + sodium dimethyldithiocarbamate (128-04-1) → tris(N,N-dimethyldithiocarbamato)iron(III) (14484-64-1)

Conditions	Yield
In chloroform; acetone addn. of Fe-complex (in CHCl3) to excess of Na2S2CNMe2 (in acetone); pptn. on concn. (vac.), filtration;

methylmercury(II) chloride (115-09-3) + tris(N,N-dimethyldithiocarbamato)iron(III) (14484-64-1) → chlorobis(N,N-dimethyldithiocarbamato)iron(III)

Conditions	Yield
In dichloromethane room temp., 10 min (pptn.); collection, washing (CH2Cl2), drying (vac., 100°C, several days);	99%
In benzene room temp., 10 min (pptn.); collection, washing (C6H6), drying (vac., 100°C, several days); elem. anal.;	99%

tris(N,N-dimethyldithiocarbamato)iron(III) (14484-64-1) + ethylmercury(II) chloride (107-27-7) → chlorobis(N,N-dimethyldithiocarbamato)iron(III)

Conditions	Yield
In benzene room temp., 10 min (pptn.); collection, washing (C6H6), drying (vac., 100°C, several days);	99%
In dichloromethane room temp., 10 min (pptn.); collection, washing (CH2Cl2), drying (vac., 100°C, several days);	99%

tris(N,N-dimethyldithiocarbamato)iron(III) (14484-64-1) → tris(dimethyldithiocarbamato)iron(I2I)

Conditions	Yield
With oxalic acid In methanol; benzene Kinetics; kinetic runs at 30°C in MeOH-C6H6, at least 10-fold excess of oxalic acid over the complex; not isolated; measuring absorbance at 348 nm;

tris(N,N-dimethyldithiocarbamato)iron(III) (14484-64-1) + sodium diethyldithiocarbamate trihydrate (20624-25-3) → tris(diethyldithiocarbamato)iron(III)

Conditions	Yield
In acetone addn. of excess NaS2CNEt2 to Fe-complex; concn. (vac.), addn. of EtOH (pptn.), filtration, washing (EtOH), drying (70°C);

Cu(4+)*3(S2CN(CH3)2)(1-)*BF4(1-)={Cu(S2CN(CH3)2)3}BF4 + tris(N,N-dimethyldithiocarbamato)iron(III) (14484-64-1) → Fe(4+)*3(S2CN(CH3)2)(1-)*BF4(1-)={Fe(S2CN(CH3)2)3}BF4 + bis(dimethyldithiocarbamato)copper(II)

Conditions	Yield
addn. of diethyl ether;; elem. anal.;;

iodine (29972-72-3) + tris(N,N-dimethyldithiocarbamato)iron(III) (14484-64-1) → Fe(3+)*2(CH3)2NCS2(1-)*(129)I2(1-)=Fe((CH3)2NCS2)2(129)I2

Conditions	Yield
In dichloromethane addn. of hexane, mixt. was left for 3 h, crystals were collected, washed with hexane, recrystd. from CH2Cl2-hexane mixt.;

tris(N,N-dimethyldithiocarbamato)iron(III) (14484-64-1) → bis(N,N-dimethyldithiocarbamato)iron(III) diiodide (79933-21-4)

Conditions	Yield
With iodine In dichloromethane addn. of hexane, mixt. was left for 3 h, crystals were collected, washed with hexane, recrystd. from CH2Cl2-hexane mixt.;

tris(N,N-dimethyldithiocarbamato)iron(III) (14484-64-1) → iodobis(N,N-dimethyldithiocarbamato)iron(III)

Conditions	Yield
With iodomethane In further solvent(s) standing of Fe-complex in iodomethane (room temp., crystn.); recrystn. (CH2Cl2 or CH2Cl2/C6H6 or hexane), drying (vac., 80°C, several days);

tris(N,N-dimethyldithiocarbamato)iron(III) (14484-64-1) → Fe(N,N-dimethyldithiocarbamate)2I2

Conditions	Yield
With I2 In benzene addn. of excess I2 to soln. of Fe-complex; crystn. on standing, collection, washing (C6H6), recrystn. (CH2Cl2/C6H6), drying (vac., 80°C); elem. anal.;

Upstream product

• 128-04-1 sodium dimethyldithiocarbamate 
• 19229-76-6 iron(III) 
• 7439-89-6 iron(II) 
• 79-45-8 N,N-dimethyldithiocarbamic acid 
• 15321-51-4 diiron nonacarbonyl 
• 137-26-8 Thiram 
• 7439-89-6 iron 
• 128-04-1 sodium N,N-dimethyldithiocarbamate dihydrate 

Relevant articles and documents

Dithiocarbamate derivatives of μ-thiocarbyne complexes: Synthesis and X-ray molecular structure of [Fe2(μ-CS)(μ-CSMe) (μ-S2CNMe2)Cp2]

Reaction of [Fe2(μ-CS)(μ-CSMe)Cp2(CO)2]+ (1) with sodium N,N-dimethyldithiocarbamate [Me2dtc]Na affords a mixture of the dithiocarbene [FeFe(μ-CS){μ-C(SMe)SC(S)NMe2}Cp(CO)] (2) and the thiocarbyne [Fe2(μ-CS)(μ-CSMe)(μ-S2CNMe2)Cp2] (3). Complex 2 is quantitatively converted into 3 by photochemical irradiation. The X-ray molecular structure of 3 demonstrates the presence of three bridging ligands and exhibits the shortest Fe-Fe interaction found in similar systems [2.453(1) A?]. Complex 3 can also be obtained by reacting [Me2dtc]- with the di-solvento thiocarbyne [Fe2(μ-CS)(μ-CSMe)(NCMe)2Cp2]+ (1a). By contrast no stable addition product has been isolated in analogous reactions involving the thiocarbyne [Fe2(μ-CO)(μ-CSMe)Cp2(CO)2]+ (1b). The [Me2dtc]- nucleophilic addition at the μ-C to form [Fe2(μ-CO){μ-C(CN)SC(S)NMe2}Cp2(CO)2] (4a) is obtained starting from [Fe2(μ-CO){μ-C(CN)(SMe2)}Cp2(CO)2]SO3CF3 (1d). Photochemical reaction of the cyanocarbene 4a causes intramolecular ring closure affording [FeFe(μ-CO){μ-C(CN)SC(S)NMe2}Cp2(CO)] (5a).

THE DIRECT ELECTROCHEMICAL SYNTHESIS OF DIALKYLDITHIOCARBAMATE AND DIETHYLDITHIOPHOSPHATE COMPLEXES OF MAIN GROUP AND TRANSITION METALS

Dialkyldithiocarbamate derivatives (R2NCS2)nM of a number of metals (M=Fe, Co, Ni, Cu, Ag, Zn, Cd, In, Tl) have been synthesised in good yield by electrochemical oxidation of appropriate sacrificial anodes in non-aqueous solutions of either the corresponding tetraalkylthiuran disulphide (R2NCS2)2 (R=Me, Et) or a mixture of carbon disulphide plus the secondary amine R2NH (R=Et, i-Pr; R2NH=piperidine).Similar experiments with solutions of (EtO)2P(S)SH (=HL) gave MLn* derivatives (M=Fe, Co, Ni, Cu, Ag, Au, Zn, Cd, Hg, Ga, In, Tl) while in the presence of HL+1,10-phenanthroline, MLn.phen derivatives were obtained for M=V, Mn, Fe, Co, Zn, and Ga.