Zinc bis(dimethyldithiocarbamate)

Last updated
Ziram
Zn(Me2dtc)2dimer.svg
Names
IUPAC name
(μ-Dimethylcarbamodithioato-1κS,2κS′)(μ-dimethylcarbamodithioato-1κS′,2κS)bis[(dimethylcarbamodithioato-κ2S,S′)zinc]
Other names
zinc dimethyldithiocarbamate, Ziram
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.808 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/2C3H7NS2.Zn/c2*1-4(2)3(5)6;/h2*1-2H3,(H,5,6);/q;;+2/p-2
    Key: DUBNHZYBDBBJHD-UHFFFAOYSA-L
  • CN(C)C(=S)[S-].CN(C)C(=S)[S-].[Zn+2]
Properties
C6H12N2S4Zn
Molar mass 305.80 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Zinc dimethyldithiocarbamate is a coordination complex of zinc with dimethyldithiocarbamate. It is a pale yellow solid that is used as a fungicide, the sulfur vulcanization of rubber, and other industrial applications. [1]

Contents

Applications

Known as ziram in agriculture, it was introduced in the United States in 1960 as a broad-spectrum fungicide. It was used to address scab on apples and pears, leaf curl in peaches, and anthracnose and blight in tomatoes. In 1981, additional uses for ziram were approved, including the prevention of leaf blight and scab on almonds, shot-hole in apricots, brown rot and leaf spot in cherries, and scab and anthracnose in pecans. Ziram also began to be used on residential ornaments as a bird and mammal repellent. [2] As a protectant fungicide, it is active on the plant’s surface where it forms a chemical barrier between the plant and a fungus. A protectant fungicide is not absorbed into the plant and must be applied prior to infection. Ziram can either be directly sprayed on to a plant’s leaf or it can be used as a soil and seed treatment. The top five crops ziram is used on are: almonds, peaches, nectarines, pears, and table and raisin grapes. [3]

Alternatively, ziram is used as an additive ingredient in industrial adhesives, caulking, and paint. It also serves as a bird and mammal repellent on outdoor ornamental items.

Chemistry

The compound is a prototypical zinc dithiocarbamate, a broad class of coordination complexes with the formulae Zn(R2NCS2)2, where R can be varied. Such compounds are produced by treating zinc and dithiocarbamate (R2NCS2−), as illustrated with dimethyldithiocarbamate: [4]

2 (CH3)2NCS2− + Zn2+ → Zn((CH3)2NCS2)2

Annually, approximately 1.9 million pounds of the active ziram ingredient are used. Ziram is often sold in powder or granule form. [2]

Zinc bis(diethyldithiocarbamate) complexes degrade thermally to give zinc sulfide. [5]

Structure

Structure of the ethyl-methyl carbamate derivative [Zn(S2CNEtMe)2]2. NAFQUGEtMedtcskewview.png
Structure of the ethyl-methyl carbamate derivative [Zn(S2CNEtMe)2]2.

Compounds of the type Zn(S2CNR2)2 are dimeric, i.e. their proper formula is [Zn(S2CNR2)2]2. [6] Each Zn center is in a distorted pentacoordinate site, with four Zn–S bonds of 2.3 Å length and one Zn–S interaction is over 2.8 Å in length. Mono-zinc derivatives are obtained by adding strong ligands (L) such as amines, which give adducts Zn(S2CNR2)2L. [7]

Ecological effects

The U.S. Environmental Protection Agency has concluded that ziram poses a low toxicity risk to mammals, a moderate risk to birds, and a high risk to aquatic species. After reviewing studies that investigated the effect of ziram on aquatic organisms, the Pesticide Action Network Pesticide Database concluded that its LC50 dose (amount of pesticide that is lethal to 50% of the test organisms within the stated study time) for amphibians places it in the "highly toxic" category.

See also

Related Research Articles

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<span class="mw-page-title-main">Zinc sulfide</span> Inorganic compound

Zinc sulfide is an inorganic compound with the chemical formula of ZnS. This is the main form of zinc found in nature, where it mainly occurs as the mineral sphalerite. Although this mineral is usually black because of various impurities, the pure material is white, and it is widely used as a pigment. In its dense synthetic form, zinc sulfide can be transparent, and it is used as a window for visible optics and infrared optics.

<span class="mw-page-title-main">Xanthate</span> Salt that is a metal-thioate/O-esters of dithiocarbonate

A xanthate is a salt or ester of a xanthic acid. The formula of the salt of xanthic acid is [R−O−CS2]−M+. Xanthate also refers to the anion [R−O−CS2]−. The formula of a xanthic acid is R−O−C(=S)−S−H, such as ethyl xanthic acid, while the formula of an ester of a xanthic acid is R−O−C(=S)−S−R', where R and R' are organyl groups. The salts of xanthates are also called O-organyl dithioates. The esters of xanthic acid are also called O,S-diorganyl esters of dithiocarbonic acid. The name xanthate is derived from Ancient Greek ξανθός (xanthos) meaning 'yellowish' or 'golden', and indeed most xanthate salts are yellow. They were discovered and named in 1823 by Danish chemist William Christopher Zeise. These organosulfur compounds are important in two areas: the production of cellophane and related polymers from cellulose and for extraction of certain sulphide bearing ores. They are also versatile intermediates in organic synthesis.

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Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. An estimated 270,000 tons were produced in 2005.

<span class="mw-page-title-main">Butyraldehyde</span> Chemical compound

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<span class="mw-page-title-main">Dithiocarbamate</span> Chemical group (>N–C(=S)–S–)

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<span class="mw-page-title-main">Sodium dimethyldithiocarbamate</span> Chemical compound

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<i>tert</i>-Butylamine Chemical compound

tert-Butylamine (also erbumine and other names) is an organic chemical compound with the formula (CH3)3CNH2. It is a colorless liquid with a typical amine-like odor. tert-Butylamine is one of the four isomeric amines of butane, the others being n-butylamine, sec-butylamine and isobutylamine.

<i>sec</i>-Butylamine Chemical compound

sec-Butylamine is an organic chemical compound (specifically, an amine) with the formula CH3CH2CH(NH2)CH3. It is a colorless liquid. sec-Butylamine is one of the four isomeric amines of butane, the others being n-butylamine, tert-butylamine, and isobutylamine. sec-Butylamine is chiral and therefore can exist in either of two enantiomeric forms.

<span class="mw-page-title-main">Thiuram disulfide</span> Class of chemical compounds

Thiuram disulfides are a class of organosulfur compounds with the formula (R2NCSS)2. Many examples are known, but popular ones include R = Me and R = Et. They are disulfides obtained by oxidation of the dithiocarbamates. These compounds are used in sulfur vulcanization of rubber as well as in the manufacture of pesticides and drugs. They are typically white or pale yellow solids that are soluble in organic solvents.

<span class="mw-page-title-main">Metsulfuron-methyl</span> Chemical compound

Metsulfuron-methyl is an organic compound classified as a sulfonylurea herbicide, which kills broadleaf weeds and some annual grasses. It is a systemic compound with foliar and soil activity, that inhibits cell division in shoots and roots. It has residual activity in soils, allowing it to be used infrequently but requiring up to 22 months before planting certain crops. It has very low toxicity to mammals, birds, fish, and insects but is a moderate eye irritant.

Zineb is the chemical compound with the formula {Zn[S2CN(H)CH2CH2N(H)CS2]}n. Structurally, it is classified as a coordination polymer and a dithiocarbamate complex. This pale yellow solid is used as fungicide.

<span class="mw-page-title-main">Maneb</span> Chemical compound

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<span class="mw-page-title-main">Ethylene thiourea</span> Chemical compound

Ethylene thiourea (ETU) is an organosulfur compound with the formula C3H6N2S. It is an example of an N,N-disubstituted thiourea. It is a white solid. It is synthesized by treating ethylenediamine with carbon disulfide.

<span class="mw-page-title-main">Iron tris(dimethyldithiocarbamate)</span> Chemical compound

Iron tris(dimethyldithiocarbamate) is the coordination complex of iron with dimethyldithiocarbamate with the formula Fe(S2CNMe2)3 (Me = methyl). It is marketed as a fungicide.

<span class="mw-page-title-main">Nickel bis(dimethyldithiocarbamate)</span> Chemical compound

Nickel bis(dimethyldithiocarbamate) is the coordination complex on nickel and dimethyldithiocarbamate, with the formula Ni(S2CNMe2)2 (Me = methyl). It is the prototype for a large number of bis(dialkhyldithiocarbamate)s of nickel(II), which feature diverse organic substituents, most of which have feature square planar molecular geometry. Nickel bis(dimethyldithiocarbamate) has been marketed as a fungicide and related complexes are used as stabilizers in polymers.

<span class="mw-page-title-main">Transition metal dithiocarbamate complexes</span>

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<span class="mw-page-title-main">Iron bis(diethyldithiocarbamate)</span> Chemical compound

Iron bis(diethyldithiocarbamate) is a coordination complex with the formula [Fe(S2CNEt2)2]2 where Et = C2H5. A red solid, it is representative of several ferrous dithiocarbamates with diverse substituents in place of ethyl. In terms of structure, the species is dimeric, consisting of two pentacoordinate iron(II) centers. It is isostructural with [Zn(S2CNEt2)2]2, which in turn is similar to zinc bis(dimethyldithiocarbamate).

References

  1. ↑ Van Gysel, August B.; Musin, Willy (2000). "Methylamines". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a16_535. ISBN   978-3527306732.
  2. 1 2 "Ziram" (PDF). EPA R.E.D Facts. United States Environmental Protection Agency. Retrieved April 26, 2015.
  3. ↑ "Ziram". Extension Toxicology Network Pesticide Information Profiles. Cornell University, Oregon State University, the University of Idaho, and the University of California at Davis and the Institute for Environmental Toxicology, Michigan State University. Retrieved April 26, 2015.
  4. ↑ Rüdiger Schubart (2000). "Dithiocarbamic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a09_001. ISBN   3527306730.
  5. ↑ Shen, Shuling; Zhang, Yejun; Peng, Long; Xu, Bing; Du, Yaping; Deng, Manjiao; Xu, Huarui; Wang, Qiangbin (2011). "Generalized Synthesis of Metal Sulfide Nanocrystals from Single-Source Precursors: Size, Shape and Chemical Composition Control and Their Properties". CrystEngComm. 13 (14): 4572. doi:10.1039/c0ce00982b. ISSN   1466-8033.
  6. 1 2 Mahid Motevalli; PaulO'Brien; John R.Walsh; Ian M.Watson (1996). "Synthesis, characterization and x-ray crystal structures of asymmetric bis(dialkyldithiocarbamates) of zinc: Potential precursors for ZnS deposition". Polyhedron. 15 (16): 2801–2808. doi:10.1016/0277-5387(95)00559-5.
  7. ↑ N. Sreehari; Babu Varghese; P. T. Manoharan (1990). "Crystal and molecular structure of dimeric bis[N,N-di-n-propyldithiocarbamato]zinc(II) and the study of exchange-coupled copper(II)-copper(II) pairs in its lattice". Inorg. Chem. 29 (20): 4011–4015. doi:10.1021/ic00345a020.


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