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 mammalrepellent on outdoor ornamental items.
Chemistryedit
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]
Structureedit
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 >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 effectsedit
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 alsoedit
Structure of the ethyl-methyl carbamate derivative [Zn(S2CNEtMe)2]2.[6]
^ ab"Ziram" (PDF). EPA R.E.D Facts. United States Environmental Protection Agency. Retrieved April 26, 2015.
^"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.
^Rüdiger Schubart (2000). "Dithiocarbamic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a09_001. ISBN3527306730.
^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.
^ abMahid 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.
^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.
Zinc bis(dimethyldithiocarbamate) in the Pesticide Properties DataBase (PPDB)
January 01, 1970
zinc, dimethyldithiocarbamate, zinc, dimethyldithiocarbamate, coordination, complex, zinc, with, dimethyldithiocarbamate, pale, yellow, solid, that, used, fungicide, sulfur, vulcanization, rubber, other, industrial, applications, ziram, names, iupac, name, dim. 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 Ziram Names IUPAC name m Dimethylcarbamodithioato 1kS 2kS m dimethylcarbamodithioato 1kS 2kS bis dimethyl wbr carbamo wbr dithioato k2S S zinc Other names zinc dimethyldithiocarbamate Ziram Identifiers CAS Number 137 30 4 Y 3D model JSmol Interactive image ChemSpider 8397 Y ECHA InfoCard 100 004 808 PubChem CID 8722 UNII 73D8UA974J Y CompTox Dashboard EPA DTXSID0021464 InChI InChI 1S 2C3H7NS2 Zn c2 1 4 2 3 5 6 h2 1 2H3 H 5 6 q 2 p 2Key DUBNHZYBDBBJHD UHFFFAOYSA L SMILES CN C C S S CN C C S S Zn 2 Properties Chemical formula C 6H 12N 2S 4Zn 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 Infobox references Contents 1 Applications 2 Chemistry 2 1 Structure 3 Ecological effects 4 See also 5 References 6 External linksApplications editKnown 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 editThe 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 edit 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 A length and one Zn S interaction gt 2 8 A in length Mono zinc derivatives are obtained by adding strong ligands L such as amines which give adducts Zn S2CNR2 2L 7 Ecological effects editThe 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 LC50dose 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 edit nbsp Structure of the ethyl methyl carbamate derivative Zn S2CNEtMe 2 2 6 Iron tris dimethyldithiocarbamate a related complex but with three dimethyldithiocarbamate ligands Nickel bis dimethyldithiocarbamate a related complex but where zinc has been replaced with nickel Zinc bis diethyldithiocarbamate a closely related complex but where methyl has been replaced with ethylReferences edit 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 a b Ziram PDF EPA R E D Facts United States Environmental Protection Agency Retrieved April 26 2015 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 Rudiger Schubart 2000 Dithiocarbamic Acid and Derivatives Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a09 001 ISBN 3527306730 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 a b 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 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 External links edithttp pmep cce cornell edu profiles extoxnet pyrethrins ziram ziram ext html Zinc bis dimethyldithiocarbamate in the Pesticide Properties DataBase PPDB Retrieved from https en wikipedia org w index php title Zinc bis dimethyldithiocarbamate amp oldid 1157382072, wikipedia, wiki, book, books, library,
