Zineb

Basic Info

Common NameZineb(F04281)
2D Structure
Description

Zineb 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. (L48, L49, L540)

FRCD IDF04281
CAS Number12122-67-7
PubChem CID5284484
FormulaC4H6N2S4Zn
IUPAC Name

zinc;N-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate

InChI Key

AMHNZOICSMBGDH-UHFFFAOYSA-L

InChI

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

Canonical SMILES

C(CNC(=S)[S-])NC(=S)[S-].[Zn+2]

Isomeric SMILES

C(CNC(=S)[S-])NC(=S)[S-].[Zn+2]

Synonyms
        
            ZINEB
        
            9006-42-2
        
            Zinc ethylenebisdithiocarbamate
        
            Polyram
        
            METIRAM
        
            12122-67-7
        
            Parzate
        
            Zinc ethylenebisthiocarbamate
        
            CHEBI:52498
        
            Cynkotox
Classifies
                

                  
                    Pollutant
                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic salts
ClassOrganic metal salts
SubclassOrganic transition metal salts
Intermediate Tree NodesNot available
Direct ParentOrganic transition metal salts
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsOrganic 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
DescriptionThis compound 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.

Properties

Property NameProperty Value
Molecular Weight275.726
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count3
Complexity108
Monoisotopic Mass273.871
Exact Mass273.871
Formal Charge0
Heavy Atom Count11
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count2

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Macadamia NutsAustralia0.2mg/kg
Broad BeansAustralia0. 5mg/kg
Broad BeansAustralia2mg/kg
StrawberriesAustralia3mg/kg
RhubarbAustralia2mg/kg
CarlicAustralia4mg/kg
BeansAustralia0. 5mg/kg
BeansAustralia2mg/kg
Citrus FruitsAustralia0. 2mg/kg
CarrotsAustralia1mg/kg
PeanutsAustralia0. 2mg/kg
Coffee BeanAustralia5mg/kg
SunflowerAustralia0.05mg/kg
LitchisAustralia5mg/kg
AsparagusAustralia1mg/kg
PotatoAustralia1mg/kg
MangoesAustralia1mg/kg
Cotton SeedAustralia10mg/kg
CeleryAustralia5mg/kg
Japanese PersimmonAustralia3mg/kg

References

TitleJournalDatePubmed ID
Mancozeb, a fungicide routinely used in agriculture, worsens nonalcoholic fatty liver disease in the human HepG2 cell model.Toxicol Lett2016 May 1327016407
Synthesis of nanopesticides by encapsulating pesticide nanoparticles using functionalized carbon nanotubes and application of new nanocomposite for plant disease treatment.J Agric Food Chem2014 May 2824832389
Synthesis and fungicidal activity of novel 3-(substituted/unsubstituted phenylselenonyl)-1-ribosyl/deoxyribosyl-1H-1,2,4-triazole.J Agric Food Chem2012 Jun 1322563913
Kinetic and thermodynamic investigation of mancozeb degradation in tomato homogenate during thermal processing.J Sci Food Agric2012 Feb21953177
The effects of fungicides on non-target mites can be mediated by plant pathogens.Chemosphere2010 Mar20172588
Suitability of two laboratory testing methods to evaluate the side effects of pesticides on Typhlodromus pyri Scheuten (Acari: Phytoseiidae).Pest Manag Sci2008 Feb18069656
Mechanisms of patulin toxicity under conditions that inhibit yeast growth.J Agric Food Chem2006 Mar 816506856
Toxicity of chemicals commonly used in Indonesian vegetable crops to Liriomyza huidobrensis populations and the Indonesian parasitoids Hemiptarsenus varicornis, Opius sp., and Gronotoma micromorpha, as well as the Australian parasitoids Hemiptarsenus varicornis and Diglyphus isaea.J Econ Entomol2004 Aug15384326
[Subchronic toxic effect of the grain fungicide PF-70 on the electrolyte barrier of the gastric mucosa in rats].Med Pr19902131395
Examination of the interaction of decis and dithane in rats.Toxicology1988 Dec 162904711
Oral toxicity of ferric dimethyl-dithiocarbamate (ferbam) and tetramethylthiuram disulfide (thiram) in rodents.J Toxicol Environ Health1978 Jan633415

Targets

Target Details

Superoxide dismutase [Cu-Zn]

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
Mechanism of Action:
Unbalanced levels of copper and zinc binding to Cu,Zn-superoxide dismutase has been linked to amyotrophic lateral sclerosis (ALS).
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 ]