Record Information
Version1.0
Creation Date2009-06-19 21:58:49 UTC
Update Date2026-03-26 21:33:36 UTC
Accession NumberCHEM001251
Identification
Common NameZineb
ClassSmall Molecule
DescriptionZineb is a polymeric complex of zinc with the ethylene bis(dithiocarbamate) anionic ligand. It is used as a fungicide to control downy mildews, rusts and redfire disease. Zinc is a metallic element with the atomic number 30. It is found in nature most often as the mineral sphalerite. Though excess zinc in harmful, in smaller amounts it is an essential element for life, as it is a cofactor for over 300 enzymes and is found in just as many transcription factors. (2, 3, 7)
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 3
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Carbamate
  • Organic Compound
  • Organometallic
  • Pesticide
  • Synthetic Compound
  • Zinc Compound
Chemical Structure
Thumb
Synonyms
ValueSource
Zinc ethane-1,2-diyldicarbamodithioateChEBI
Zinc ethane-1,2-diyldicarbamodithioic acidGenerator
CynkotoxMeSH
NovozirMeSH
Dithane Z 78MeSH
Dithane Z-78MeSH
Dithane Z78MeSH
Zinc ethylenebis(dithiocarbamate)MeSH
Chemical FormulaC4H6N2S4Zn
Average Molecular Mass275.773 g/mol
Monoisotopic Mass273.871 g/mol
CAS Registry Number12122-67-7
IUPAC Namezinc(2+) ion ({2-[(sulfanidylmethanethioyl)amino]ethyl}carbamothioyl)sulfanide
Traditional Namezinc(2+) ion ({2-[(sulfanidylmethanethioyl)amino]ethyl}carbamothioyl)sulfanide
SMILES[Zn++].[S-]C(=S)NCCNC([S-])=S
InChI IdentifierInChI=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
InChI KeyAMHNZOICSMBGDH-UHFFFAOYSA-L
Chemical Taxonomy
Description belongs to the class of organic compounds known as organic transition metal salts. These are organic salt compounds containing a transition metal atom in its ionic form.
KingdomOrganic compounds
Super ClassOrganic salts
ClassOrganic metal salts
Sub ClassOrganic transition metal salts
Direct ParentOrganic transition metal salts
Alternative Parents
Substituents
  • Organic transition metal salt
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite crystals.
Experimental Properties
PropertyValue
Melting Point157°C
Boiling PointNot Available
Solubility0.01 mg/mL at 25°C [TOMLIN,C (1997)]
Predicted Properties
PropertyValueSource
Water Solubility0.086 g/LALOGPS
logP1.03ALOGPS
logP1.97ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area24.06 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity60.76 m³·mol⁻¹ChemAxon
Polarizability20.95 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-853688694acf7f7c42f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-853688694acf7f7c42f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0090000000-853688694acf7f7c42f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-22de404b22a8c0dd4656Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-22de404b22a8c0dd4656Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0090000000-22de404b22a8c0dd4656Spectrum
Toxicity Profile
Route of ExposureOral (3) ; inhalation (3) ; dermal (3)
Mechanism of ToxicityAnaemia results from the excessive absorption of zinc suppressing copper and iron absorption, most likely through competitive binding of intestinal mucosal cells. Unbalanced levels of copper and zinc binding to Cu,Zn-superoxide dismutase has been linked to amyotrophic lateral sclerosis (ALS). Stomach acid dissolves metallic zinc to give corrosive zinc chloride, which can cause damage to the stomach lining. Metal fume fever is thought to be an immune response to inhaled zinc. (2, 3, 1)
MetabolismZinc can enter the body through the lungs, skin, and gastrointestinal tract. Intestinal absorption of zinc is controlled by zinc carrier protein CRIP. Zinc also binds to metallothioneins, which help prevent absorption of excess zinc. Zinc is widely distributed and found in all tissues and tissues fluids, concentrating in the liver, gastrointestinal tract, kidney, skin, lung, brain, heart, and pancreas. In the bloodstream zinc is found bound to carbonic anhydrase in erythrocytes, as well as bound to albumin, _2-macroglobulin, and amino acids in the the plasma. Albumin and amino acid bound zinc can diffuse across tissue membranes. Zinc is excreted in the urine and faeces. (3)
Toxicity ValuesLD50: 1850 mg/kg (Oral, Rat) (8)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (6)
Uses/SourcesZineb is used as a fungicide to control downy mildews, rusts and redfire disease. (7)
Minimum Risk LevelIntermediate Oral: 0.3 mg/kg/day (5) Chronic Oral: 0.3 mg/kg/day (5)
Health EffectsChronic exposure to zinc causes anemia, atazia, lethargy, and decreases the level of good cholesterol in the body. It is also believed to cause pancreatic and reproductive damage. (3)
SymptomsIngestion of large doses of zinc causes stomach cramps, nausea, and vomiting. Acute inhalation of large amounts of zinc causes metal fume fever, which is characterized by chills, fever, headache, weakness, dryness of the nose and throat, chest pain, and coughing. Dermal contact with zinc results in skin irritation. (3)
TreatmentZinc poisoning is treated symptomatically, often by administering fluids such as water or milk, or with gastric lavage. (3)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkZineb
Chemspider IDNot Available
ChEBI ID52498
PubChem Compound ID8873
Kegg Compound IDC15232
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22155123
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23871785
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=465777