Definition
ChEBI: A naphthodithiin that is 5,10-dioxo-5,10-dihydronaphtho[2,3-b][1,4]dithiin which is substituted by nitrile groups at positions 2 and 3. It is a broad spectrum fungicide used to control scab, downy mildew, rust, and leaf spot in the commercial
rowing of grapes and other fruit, citrus, coffee, and vegetables.
Description
Dithianone is an anthraquinone derivative, used as a
fungicide. With cymoxanil, it is contained in Aktuan.
Cases have been sparsely reported for agricultural
workers.
History
The
ethylenebisdithiocarbamates were rediscovered in 1945
when Dimond et al. (2) reported a “new water soluble
protectant fungicide.” The parent compound, disodium
ethylenebisdithiocarbamate, was highly soluble in water
and was unstable in air, and it might have been only
a laboratory curiosity and remained unnoticed but for
the applications developed by Heuberger and Manns (3),
who stabilized it by converting it into zinc salt by the
addition of zinc sulfate–lime mixture. This was followed
by the introduction of zineb as fungicide by the Rohm and
Haas Company, USA.
The same phenomenon was later
confirmed by Barratt and Horsfall (4), who attributed
the stabilizing effect as due to zinc salt formation.
From the numerous compounds suggested by Hester (5),
only disodium ethylenebisdithiocarbamate and its zinc
and manganese salts are largely accepted for practical
application. Research on these dithiocarbamates led to
some promising variants.
Agricultural Uses
Fungicide: Fungicide used to control certain mildews. A seed
dressing; used to attack foliar diseases of fruits (pome,
stone, etc,), coffeee, wine, and vegetables. Not currently
registered for use in the U.S. Approved for use in most EU
countries.
Trade name
DELAN®; DELAN-COL®; DELAN
70WG®; DITHIANON FLOWABLE®; DITHIANONWG®;
IT 931®; MV 119A®; STAUFFER MV-119A®;
THYNON®
Mechanism of action
Dithianon's is a protectant with some curative activity. It has multi-site activity involving the reaction with thiol groups in various fungal enzymes, disrupting critical metabolic pathways including the glycolytic pathway, Krebs cycle, and cellular respiration ultimately leading to cellular death.
Synthesis
Using sodium monophosphate disodium phosphate to prepare a buffer solution of pH 7 (prepared by adding 19.5 ml of 0.2 M dibasic sodium phosphate 30.5 ml / 0.2 M monobasic sodium phosphate in 500 ml of water) In 1.7 L of the solution, 60 g of diclones were dispersed using 3 g of a surfactant (polyethylene lauric acid), and the temperature was cooled to 10 ° C. 160.5 g of an aqueous solution of ethene salt (36% of ethene salt) is slowly added dropwise over 2 hours. After the addition was completed, the reaction was further performed for 1 hour, filtered at that temperature, washed with water, and dried to obtain 70.4 g (yield 90.0%, purity 93.5%) of dithianon.[1]
References
[1] Process for preparing high purity 2,3-dicyano-1,4-dithia anthraquinone. Patent No. KR100209582B1
