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Record Information
Version2.0
Creation Date2009-06-19 21:58:49 UTC
Update Date2014-12-24 20:23:57 UTC
Accession NumberT3D1466
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. (3, 4, 7)
Compound Type
  • Amine
  • Carbamate
  • Organic Compound
  • Organometallic
  • Pesticide
  • Synthetic Compound
  • Zinc Compound
Chemical Structure
Thumb
Synonyms
Synonym
((1,2-Ethanediylbis(carbamodithioato))(2-))zinc
1,2-Ethanediylbis(carbamodithioato) (2-)-S,S'-zinc
1,2-Ethanediylbiscarbamodithioic acid, zinc complex
Aaphytora
Aphytora
Aspor
Asporum
Blightox
Blizene
Bombardier
Carbadine
Chem zineb
Cineb
Clortocaffaro
Crittox
Crystal zineb
Cynkotox
Daisen
Deikusol
Devizeb
Dipher
Discon
Discon-z
Dithane 65
Dithane z
Dithane Z-78
Ditiamina
Ethylenebis(dithiocarbamato)zinc
Ethylenebis(dithiocarbamic acid), zinc salt
Fitodith 80
Fungo-pulvit
Funjeb
Hexathane
Kupratsin
Kypzin
Lipotan
Lirotan
Lonacol
Metiram-zinc
Micide
Micide 55
Novosir n
Novozin N 50
Novozir
Novozir n
Novozir N 50
Pamosol 2 forte
Parzate
Parzate c
Parzate zineb
Perosin
Perosin 75B
Perozin
Perozine
Perozine 75B
Phytox
Pilzol SZ
Polyram z
Sperlox-z
Taloberg
Tanazon
Thiodow
Thionic m
Tiazin
Tiezene
Tritoftorol
Tsineb
Unizeb
Zebenide
Zebtox
Zidan
zinc ethane-1,2-diylbis(dithiocarbamate)
Zinc ethane-1,2-diyldicarbamodithioate
Zinc ethylene bisdithiocarbamate
Zinc ethylene-1,2-bisdithiocarbamate
Zinc ethylenebis(dithiocarbamate) (polymeric)
Zinc ethylenebisdithiocarbamate
Zinc ethylenebisthiocarbamate
Zinc n,n'-ethylenebisdithiocarbamate
Zincethylenebisdithiocarbamate
Zineb 75
Zineb 75 WP
Zineb 80
Zineb-R
Zinosan
Zipar
[ethane-1,2-diylbiscarbamodithioato(2-)-kappaS]zinc
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 KeyInChIKey=AMHNZOICSMBGDH-UHFFFAOYSA-L
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as organic transition metal salts. These are organic salt compounds containing a transition metal atom in its ionic form.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic salts
Sub ClassOrganic 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)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0865 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity60.76 m3·mol-1ChemAxon
Polarizability20.95 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4) ; dermal (4)
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. (3, 4, 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. (4)
Toxicity ValuesLD50: 1850 mg/kg (Oral, Rat) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (8)
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 (6) Chronic Oral: 0.3 mg/kg/day (6)
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. (4)
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. (4)
TreatmentZinc poisoning is treated symptomatically, often by administering fluids such as water or milk, or with gastric lavage. (4)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID5284484
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDC15232
UniProt IDNot Available
OMIM ID
ChEBI ID52498
BioCyc IDNot Available
CTD IDD015038
Stitch IDZineb
PDB IDNot Available
ACToR ID1497
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D1466.pdf
General References
  1. Vonk WI, Klomp LW: Role of transition metals in the pathogenesis of amyotrophic lateral sclerosis. Biochem Soc Trans. 2008 Dec;36(Pt 6):1322-8. doi: 10.1042/BST0361322. [19021549 ]
  2. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  3. Wikipedia. Zinc. Last Updated 24 March 2009. [Link]
  4. ATSDR - Agency for Toxic Substances and Disease Registry (2005). Toxicological profile for zinc. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  5. Wikipedia. Metallothionein. Last Updated 20 December 2008. [Link]
  6. ATSDR - Agency for Toxic Substances and Disease Registry (2001). Minimal Risk Levels (MRLs) for Hazardous Substances. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  7. Wikipedia. Zineb. Last Updated 15 May 2009. [Link]
  8. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Zinc ion binding
Specific Function:
Destroys radicals which are normally produced within the cells and which are toxic to biological systems.
Gene Name:
SOD1
Uniprot ID:
P00441
Molecular Weight:
15935.685 Da
References
  1. Vonk WI, Klomp LW: Role of transition metals in the pathogenesis of amyotrophic lateral sclerosis. Biochem Soc Trans. 2008 Dec;36(Pt 6):1322-8. doi: 10.1042/BST0361322. [19021549 ]