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The Crystal Structure of Zineb, 75 years later

preprint
submitted on 17.09.2019 and posted on 23.09.2019 by Jonathan B Lefton, Kyle B Pekar, Tomce Runcevski
Ethylene bis(dithiocarbamates) (EBDTCs) have been used as staple fungicides for over 75 years. The first industrially manufactured EBDTC was zineb, zinc ethylene bis(dithiocarbamate), marketed under the tradename Dithane. Even though zineb has been used as a fungicide since the 1940s, its crystal structure remained unknown. Herein, we describe the crystal structure of zineb (triclinic crystal system, space group P–1, a = 7.5094(9) Å, b = 9.4356(9) Å, c = 7.4120(7) Å, α = 107.945(8) °, β = 100.989(7) °, γ = 105.365(8) °, V = 460.07(10) Å3). The inorganic fragment of the structure consists of two Zn2+ cations, coordinated by the thiocarbamate group. There are four Zn–S bonds with lengths in the range of 2.325 – 2.426 Å, and one rather long Zn–S contact of 2.925(8) Å. Inorganic fragments are linked by organic EBDTC ligands to form extended, polymeric layers. The layers are packed in a ABAB manner, related by the inversion symmetry and held together by hydrogen bonding network. In this article, in addition to describing the crystal structure, we correlate the structural features with the vibrational spectroscopic and thermal characteristics of zineb, and we provide a short summary of the major developments of fungicides in the 20th century

Funding

Welch Foundation

History

Email Address of Submitting Author

truncevski@smu.edu

Institution

Southern Methodist University

Country

USA

ORCID For Submitting Author

0000-0003-0886-8464

Declaration of Conflict of Interest

none

Version Notes

first submission

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in Crystal Growth & Design

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