142-59-6

Basic information

• Product Name: NABAM
• Synonyms: nabam (ISO) disodium ethylenebis(N,N'-dithiocarbamate);D-14;1,2-Ehanediylbiscarbamodithioicaciddisodiumsalt;CarbaModithioic acid,N,N'-1,2-ethanediylbis-, sodiuM salt (1:2);1,2-ethanediylbiscarbamodithioicaciddisodiumsalt;1,2-ethanediylbis-carbamodithioicacidisodiumsalt;Carbamodithioicacid,1,2-ethanediylbis-,disodiumsalt;carbond
• CAS NO: 142-59-6
• Molecular Formula: C₄H₆N₂S₄*2Na
• Molecular Weight: 256.34
• EINECS: 205-547-0
• Mol File: 142-59-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 76-80 °C
• Boiling Point: 308.2 °C at 760 mmHg
• Flash Point: 140.2 °C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: Negligible
• Storage Temp.: 0-6°C
• Water Solubility: ca. 200 g l-1 (room temperature)
• Merck: 13,6367
• CAS DataBase Reference: NABAM(CAS DataBase Reference)
• NIST Chemistry Reference: NABAM(142-59-6)
• EPA Substance Registry System: NABAM(142-59-6)

Safety Data

• Hazard Codes: Xn,N
• Statements: 36/37/38-50/53-43-37-22
• Safety Statements: 26-36/37/39-61-60-46-24/25-8
• RIDADR: UN3077 9/PG 3
• RTECS: FA6825000
• Hazardous Substances Data: 142-59-6(Hazardous Substances Data)

Usage

Description

NABAM, also known as the disodium salt of ethylenebis(dithiocarbamic acid), is a colorless to light amber solid with a slight odor. It is easily soluble in water and is used as a fungicide, algicide, and bactericide on various crops. However, it is considered a carcinogen and is not licensed for use within the European Union.

Uses

Used in Agricultural Industry:
NABAM is used as a fungicide, algicide, and bactericide to prevent crop damage by fungi, protect harvested products from deterioration, and serve as an industrial microbiocide. It is registered for use in the U.S. and Canada, but not approved for use in EU countries.
Used in Plant Protection:
NABAM is used as a plant fungicide, providing protection against fungal diseases of cotton, capsicums, and onions when applied to soil.
Used as a Starting Material for Pesticides:
NABAM serves as a starting material for derivatives that are also used as pesticides.

Air & Water Reactions

Water soluble. Decomposes in boiling hot to give poisonous hydrogen sulfide and flammable carbon disulfide.

Reactivity Profile

NABAM 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 skin and mucous membranes, nar-cotic in high concentrations, use may be restricted.

Health Hazard

Contact with liquid irritates eyes and may cause mild to severe erythema of skin as well as sensitization reactions.

Fire Hazard

Behavior in Fire: If water solution boils, poisonous hydrogen sulfide and highly flammable carbon disulfide vapors form.

Trade name

AMA-30?, Kemira Chemical (Finland); CAMBELL’S? NABAM SOIL FUNGICIDE; CARBON D?; NALCO D-62C44?; CHEM-BAM?; DITHANE A-40?; DITHANE A-46?; DITHANE D-14?[C]; NAFUN-IPO?; NALCO? D-62C44; PARZATE?; SPRING-BAK?

Safety Profile

intraperitoneal route. Experimental teratogenic and reproductive effects. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx, Na2O, and SOx. See also CARBAMATES.

Potential Exposure

Nabam is a broad spectrum dithiocarbamate fungicide/bactericide/algaecide/herbicide/microbiocide used to prevent crop damage by fungi, to protect harvested products from deterioration, and as an industrial microbiocide. As a result of the United States Environmental Protection Agency review of nabam in 1989, all food uses were voluntarily canceled by the manufacturers except for one FDA-regulated food use on sugar mill grinding, crusher, and/or diffuser systems, e.g., processing water systems. All other uses of nabam are for the control of algae, slime-forming bacteria, and fungi in indoor nonfood environments, paper mills, water cooling systems, drilling mud and packer fluids, and secondary oil recovery water system. Registered in the United States only for nonfood application.

Metabolic pathway

Nabam and other alkylenebis(dithi0carbamate) fungicides are degraded and metabolised via a common pathway. Limited information is available to describe the fate of nabam in soil and animals. Based on information generated with structurally similar compounds (see maneb, zineb), the initial degradation reaction of nabam in water and plants involves the dissociation of the metal complex and decomposition to numerous degradation products including ethylenethiourea (ETU) and ethyleneurea (EU) as major products (Scheme 1).

Shipping

UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard Class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.

Purification Methods

It crystallises (as hexahydrate) from aqueous ethanol. It is a skin irritant. [Beilstein 4 III 149, 4 IV 234.]

Degradation

In aqueous solution, ethylenebis( thiocarbamate) compounds (eg. maneb, zineb) decompose to yield ethylenetl.uourea (ETU, 2) and 5,6-dihydro- 3H-imidazo[2,l-c]-1,2,4-dithiazole-3-thione(3) (kaars Sijpestijn and Vonk, 1974). Nabam (1) decomposed to a complex pattern of degradation products when exposed to aqueous solution at 90 °C (Marshall, 1977). A possible degradation pathway involves the oxidation of nabam to ethylenethiuram disulfide (4) which is further degraded to ETU (2) and compound 3. Other decomposition products included carbon disulfide, hydrogen sulfide, ethylene diisothiocyanate (5), β-aminoethy 1 isothiocyanate (6), β-aminoethyl dithiocarbamate (7) and ethylenediamine (8). The primary hydrolytic and thermal degradation pathways of nabam are presented in Scheme 1 ETU in aqueous solution was ultimately converted into 2-imidazoline (9) and EU (10) (kaars Sijpesteijn and Vonk, 1974).

Incompatibilities

Combustible material. Dust may form explosive mixture in air, water, acid, oxidizing materials. Heat or contact with moisture or acids causes rapid decomposition and the generation of toxic and flammable hydrogen sulfide and carbon disulfide. 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. Corrosive to iron, copper, brass, and zinc metals, especially in the presence of moisture. Heat alkalies (lime), moisture can cause decomposition. Decomposes on prolonged storage; by moisture, light, and heat. Degradation produces ethylene thiourea.

Waste Disposal

Do not discharge into drains or sewers. Dispose of waste material as hazardous waste using a licensed disposal contractor to an approved landfill. 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. A potential candidate for liquid injection incineration at a temperature range of 650 1600℃ and a residence time 0.1-2 seconds. Also, a potential candidate for rotary kiln incineration at a temperature range of 820 1600℃ and residence times of seconds for liquids and gases, and hours for solids.

InChI:InChI=1/C4H8N2S4.2Na/c5-3(7)9-1-2-10-4(6)8;;/h1-2H2,(H2,5,7)(H2,6,8);;/q;2*+1

Upstream product

• 75-15-0 carbon disulfide 
• 107-15-3 ethylenediamine 
• 125634-77-7 ethoxylated pentaerythitol tetraacrylate 

Downstream Products

• 5035-56-3 (C₆H₅)2SbS₂CNHCH₂CH₂NHCS₂Sb(C₆H₅)2 
• 113679-99-5 bis(tetraphenylphosphonium) ethylenebis(dithiocarbamate) 
• 101347-99-3 2C₆H₅^(1-)*Sn⁽⁴⁺⁾*S₂CNHCH₂CH₂NHCS₂^(2-) = (C₆H₅)2Sn(S₂CNHCH₂CH₂NHCS₂) 
• 97115-69-0 5,5'-dibenzyl-3,3'-ethane-1,2-diyl-bis-[1,3,5]thiadiazinane-2-thione 
• 95486-92-3 5,5'-bis-(4-chloro-phenyl)-3,3'-ethane-1,2-diyl-bis-[1,3,5]thiadiazinane-2-thione 

Related news

New strategy for amperometric determination of NABAM (cas 142-59-6) pesticide by using potential assisted surface oxide regeneration method09/28/2019

This project demonstrates a novel amperometric method to measure the concentration of nabam through a process of potential assisted surface oxide on the copper based electrode. Based on the strong cuprous ion chelating capability of nabam, the cuprous oxide layer is dissolved away from the elect...detailed

Relevant articles and documents

Compound heavy metal chelating agent containing dithiocarboxylate functionalized ethoxylated pentaerythritol core hyperbranched polymer

A compound heavy metal chelating agent, which relates to the field of chemical and environmental protection technology, includes dithiocarboxylate functionalized ethoxylated pentaerythritol core hyperbranched polymer and alkylene diamine-N,N′-sodium bisdithiocarboxylate with a molar ratio in a range of 1:1.0 to 1:10.0. The two different structural types of components have the synergistic positive effect. While chelating heavy metals, the compound heavy metal chelating agent alternately combine with heavy metals to form insoluble chelating super-molecular deposits, which has both chelation and flocculation functions. The compound heavy metal chelating agent provided by the present invention is able to reach the standard for treating heavy metal wastewater, and especially low concentration heavy metal wastewater. It has a wide adaptability range, and does not need to add coagulant. Moreover, it is simple in preparation method, easily available for raw materials, low in cost, and easy to be industrialized.

Mechanisms of acid decomposition of dithiocarbamates. 2. Efficiency of the intramolecular general acid catalysis

The acid decomposition of ethylenebis(dithiocarbamate) (EbisDTC) and glycinedithiocarboxylate (glyDTC) was studied in water at 25 °C in the range of rio -5 to pH 5. The acid dissociation constants of all species involved were calculated from LFER and from the pH-rate profiles. According to the pK(a) of the parent amine of the reactive species, both compounds decompose through the dithiocarbamate anion and a zwitterion intermediate. The intermolecular N-protonation rate constant of the carboxylic conjugate acid of glyDTC anion is 12.6 M-1 s-1, slower than the C-N breakdown. This species also cleaves through an intramolecular general acid-catalyzed mechanism where the rate constant for the N-protonation is (7.1 ± 4.2) x 103 s-1 and the efficiency of the proton-transfer step as measured by the effective molarity is (5.6 ± 3.3) x 102 M. The acid decomposition of the dithiocarbamic conjugate acid of EbisDTC anion proceeds through a fast N- protonation and a slower C-N breakdown. The intramolecular general acid catalysis rate constant is (8.2 ± 2.8) x 106 s-1, but the efficiency of this fast proton transfer is only (14.3 ± 4.9) M. The intramolecular general acid catalysis of the free acid forms of the carboxylic and dithiocarbamic groups is unfavorable for about 4 kcal mol-1 with respect to the protonation of the external hydron, and consequently, no external buffer catalysis is expected to be observed for dithiocarbamates that decompose through a zwitterion intermediate. The difference between the pK(b) of the proton acceptor and the pK(a) of the donor follows the order of the proton efficiency. Estimation of the strength of the hydrogen bonding in the reagent and product supports the assumption that a thermodynamically favorable change of hydrogen bonding from reagent to product increases the efficiency of proton transfer.

Fungicidal compositions employing synergistic mixtures of phenylacetamide derivatives and Zineb or Mancozeb

Synergistic mixtures of fungicidal N-(2,6-dimethyl-phenyl)-N-(1-methoxycarbonyl-ethyl)-phenylacetamide with other selected fungicides which are ethylene-bis-dithiocarbamates, N-trichloromethylthio-imides or copper oxychloride are disclosed as are compositions comprising the synergistic mixtures. Said mixtures and compositions are effective in controlling fungi infections of useful plants.