142-59-6 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.
Check Digit Verification of cas no
The CAS Registry Mumber 142-59-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 2 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 142-59:
(5*1)+(4*4)+(3*2)+(2*5)+(1*9)=46
46 % 10 = 6
So 142-59-6 is a valid CAS Registry Number.
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
142-59-6Relevant articles and documents
Ethoxylated trimethylolpropane core hyperbranched polymer taking dithiocarboxylate as side group and end group and application of chelating metal
-
Paragraph 044-0048, (2020/05/14)
The invention provides an ethoxylated trimethylolpropane core hyperbranched polymer taking dithiocarboxylate as a side group and an end group and a preparation method and application of the ethoxylated trimethylolpropane core hyperbranched polymer as a heavy metal chelating agent, and relates to the technical field of chemical engineering and environmental protection. The chemical formula of the ethoxylated trimethylolpropane core hyperbranched polymer taking dithiocarboxylate as a side group and an end group is CH3CH2C [CH2OCH2CH2OCOCH2CH2CH2N (CSSM) CH2CH2NHCSSM] 3, wherein M is Na, Kor NH4. The hyperbranched polymer provided by the invention is simple in preparation method, easily available in raw materials and easy to industrialize. The hyperbranched polymer can be used as aheavy metal chelating agent, the special three-dimensional space structure of the hyperbranched polymer can be alternately chelated with heavy metals to form a three-dimensional super-macromolecular combination with low solubility and strong stability, and wastewater and wastes containing heavy metals can be effectively treated.
Mechanisms of acid decomposition of dithiocarbamates. 2. Efficiency of the intramolecular general acid catalysis
Humeres, Eduardo,Debacher, Nito A.,Sierra, M. Marta De S.
, p. 1807 - 1813 (2007/10/03)
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
-
, (2008/06/13)
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.