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12122-67-7

12122-67-7 Structure

12122-67-7 Structure
IdentificationMore
[Name]

Zineb
[CAS]

12122-67-7
[Synonyms]

((1,2-ethanediylbis(carbamodithioato))(2-))-zin
((1,2-ethanediylbis(carbamodithioato))(2-))zinc
(ethylenebis(dithiocarbamato))-zin
1,2-ethanediylbis(carbamodithioato)(2-)-s,s’-zinc
1,2-ethanediylbis-carbamodithioicacizincsalt
aphytora
aspor
asporum
bercema
blightox
blizene
carbadine
carbamodithioicacid,1,2-ethanediylbis,zincsalt
caswellnumber930
chemzineb
cineb
crystalzineb
cynkotox
daisen
deikusol
[EINECS(EC#)]

235-180-1
[Molecular Formula]

C4H6N2S4Zn
[MDL Number]

MFCD00067266
[Molecular Weight]

275.75
[MOL File]

12122-67-7.mol
Chemical PropertiesBack Directory
[Description]

Zineb is a light-coloured powder/crystal and insoluble in water. Zineb is one of the nonsystemic (surface-acting) fungicides of the group ethylenebisdithiocarbamates (EBDCs). Zineb is a polymer of ethylene (bis)thiocarbamate units linked with zinc and used for the control and prevention of crop damage in the field and also to protect harvested crops from deterioration during storage or transport. Zineb was used to protect fruit and vegetable crops from a wide range of foliar and other diseases. It was available in the United States as wettable powder and dust formulations. Zineb can be formed by combining nabam and zinc sulphate in the spray tank.
[Appearance]

Light-tan solid. Insoluble in water; soluble in pyridine; decomposes on heating.
[Melting point ]

157°C (rough estimate)
[vapor pressure ]

<1x l0-5 at 20 °C
[Fp ]

90℃
[storage temp. ]

2-8°C
[solubility ]

DMSO (Heated, Very Slightly)
[density ]

1.74 g/cm3
[form ]

Water-Insoluble Powder
[Water Solubility ]

ca.10 mg l-1 (room temperature)
[color ]

White to off-white
[Merck ]

13,10220
[BRN ]

4165797
[Henry's Law Constant]

2.7×103 mol/(m3Pa) at 25℃, Mackay et al. (2006)
[Major Application]

agriculture
environmental
[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
[Contact allergens]

Zineb is a pesticide of the dithiocarbamate group. Sensitization can occur in gardeners and florists.
[InChIKey]

AMHNZOICSMBGDH-UHFFFAOYSA-L
[SMILES]

S=C1NCCNC(=S)S[Zn]S1
[CAS DataBase Reference]

12122-67-7(CAS DataBase Reference)
[IARC]

3 (Vol. 12, Sup 7) 1987
[EPA Substance Registry System]

12122-67-7(EPA Substance)
Hazard InformationBack Directory
[Definition]

ChEBI: A polymeric complex of zinc with the ethylene bis(dithiocarbamate) anionic ligand. Formerly used as an agricultural fungicide for the control of downy mildews and rusts, its use is no longer permitted in the US or the EU.
[Uses]

Agricultural fungicide.
[General Description]

An off-white powder. Used as a fungicide.
[Reactivity Profile]

ZINEB(12122-67-7) is a zinc salt of a dithiocarbamic acid. May generate flammable gases with aldehydes, nitrides, and hydrides. Incompatible with acids, peroxides, and acid halides.
[Air & Water Reactions]

Decomposes gradually, accelerated by exposure to air, moisture, and heat. Insoluble in water. Thio and dithiocarbamates slowly decompose in aqueous solution to form carbon disulfide and methylamine or other amines. Such decompositions are accelerated by acids.
[Fire Hazard]

Flash point data for this chemical are not available, but ZINEB is probably combustible.
[Chemical Properties]

Light-tan solid. Insoluble in water; soluble in pyridine; decomposes on heating.
[Production Methods]

The production of zineb involves a two-step chemical synthesis process. First, ethylenediamine is reacted with carbon disulphide and aqueous ammonia in the presence of a stabiliser such as sodium pyrosulphite, sodium sulphite, or sodium hydrosulphite. This reaction yields an intermediate compound known as "ambis." In the second step, ambis is reacted with zinc chloride in the presence of a catalyst, commonly bismuth molybdate, nickel on alumina or cobalt-based catalysts, to produce zineb.
[Hazard]

Toxic by inhalation and ingestion; irritant to eyes and mucous membranes. Questionable carcinogen.
[Mechanism of action]

Non-specific with protective action. Multi-site activity. It disrupts fungal enzyme activity by reacting with metal-containing enzymes, particularly those involved in spore germination and fungal growth.
[Metabolic pathway]

Zineb and other alkylenebis( dithiocarbamate) fungicides are degraded and metabolised via a common pathway. The primary degradation reaction of zineb in water, soil, plants and animals involves the initial dissociation of the metal complex and decomposition to numerous degradation products including ethylenethiourea (ETU) and ethyleneurea (EU) as major products (Scheme 1).
[Purification Methods]

Crystallise this herbicide several times from hot toluene or from hot CHCl3 by addition of EtOH. It is a skin irritant. [Beilstein 4 III 149, 4 IV 234.]
[Degradation]

[14C-ethylene]Zineb(1) was decomposed mainly to ETU (2) in an aqueous suspension after 14 days via the 5,6-dihydro-3H-imidazo[2,1-c]-1,2,4- dithiazole-3-thione (3) intermediate (Vonk, 1976). In dilute alkaline solution and in the presence of light, heat and moisture, zineb decomposed rapidly to compound 3 (Marshall, 1978). ETU (2) in aqueous solutions was further converted into 2-imidazoline (4) and EU (5) (kaars Sijpesteijn and Vonk, 1974). Zineb decomposed in sterile marine culture medium to yield ETU (2) and compound 3. In the presence of copper, an additional degradation product, ethylene diisothiocyanate (6), was also observed (Hunter and Evans, 1991).
[Toxicity evaluation]

Zineb has a low mammalian toxicity however, it may cause adverse reproduction/developement effects if ingested. It is moderately toxic to most fauna and flora.
[Pesticide Type]

Fungicide
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)Environment (GHS09)
GHS07,GHS09
[Signal word ]

Warning
[Hazard statements ]

H302-H317-H335-H410
[Precautionary statements ]

P261-P264-P273-P280-P301+P312-P302+P352
[Hazard Codes ]

Xi
[Risk Statements ]

R37:Irritating to the respiratory system.
R43:May cause sensitization by skin contact.
[Safety Statements ]

S8:Keep container dry .
S24/25:Avoid contact with skin and eyes .
S46:If swallowed, seek medical advice immediately and show this container or label .
[RIDADR ]

UN 3077 9 / PGIII
[WGK Germany ]

3
[RTECS ]

ZH3325000
[HazardClass ]

6.1
[PackingGroup ]

III
[HS Code ]

29309090
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Acute Tox. 4 Oral
Aquatic Acute 1
Aquatic Chronic 1
Skin Sens. 1
STOT SE 3
[Hazardous Substances Data]

12122-67-7(Hazardous Substances Data)
[Toxicity]

LD50 orally in rats: >5000 mg/kg (Gaines)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Sodium hydroxide-->Sulfuric acid-->Sodium carbonate-->Fuming sulfuric acid-->Carbon disulfide-->Water-->Ethylenediamine-->Zinc sulphate-->NABAM
[Preparation Products]

Maneb
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Zinc-ethylenebis(dithiocarbamate)(12122-67-7).msds
Spectrum DetailBack Directory
[Spectrum Detail]

Zineb(12122-67-7)MS
Zineb(12122-67-7)IR1
Zineb(12122-67-7)IR2
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

12122-67-7(sigmaaldrich)
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