Dipymetitrone | Fungicides

Dipymetitrone [2,6-dimethyl-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone] is a fungicide launched by Bayer CropScience in 2014.

Dipymetitrone: 2D and 3D Structure

The biochemical activities of Dithiine-tetracarboximides as already known; such as:

a: Anthelmintics against internal parasites of animals, in particular against nematodes.

b: Insecticidal activity.

c: Antibacterial effect against pathogens causing mycoses in humans.

Furthermore, it is known that Dithiine-tetracarboximides can be used as pigments in electrophotographic photoreceptors or as colorants in paints and polymers [1, 2].

Mechanism for Activity

There is no mechanism available right now.

Developer

It is developed and launched by Bayer Cropscience in 2014.

Reported Activities for Dipymetitrone

No data is reported.

Summary

Common name: Dipymetitrone

Trademarks: -

Molecular Formula: C10H6N2O4S2

CAS Registry Number: 16114-35-5

CAS Name: 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone

Molecular Weight: 282.30

SMILES: O=C(C1=C2SC3=C(C(N(C)C3=O)=O)S1)N(C)C2=O

InChI Key: FPKXBFWMIYHCID-UHFFFAOYSA-N

InChI: InChI=1S/C10H6N2O4S2/c1-11-7(13)3-4(8(11)14)18-6-5(17-3)9(15)12(2)10(6)16/h1-2H3

Mechanism of Action: Unknown

Activity: Fungicides; Anthelmintics; Insecticidal; Antibacterial

Status: Launched 2014 (US)

Chemical Class: Sulphur containing; Thio containing; Small-molecules; Dithiine-tetracarboximides

Originator: Bayer CropScience

Dipymetitrone Synthesis

WO2012028588A1: The process appears to industrial preparation of Dipymetitrone. It involves atypical oxidation reaction by thionyl chloride. The synthesis starts from the reaction of methylamine and succinic anhydride to afford 4-amino-4-oxobutanoic acid. Treatment of 4-amino-4-oxobutanoic acid with thionyl chloride and isomerization of the intermediate diisomaleimide-dithiine with water yields Dipymetitrone. See also Ref 2, 3.

US3364229A: It is the oldest reported synthesis for Dipymetitrone. The process suffers from failures as the handling of the highly toxic hydrogen sulfide gas is technically very difficult and costly. When using thiourea unwanted byproducts other than the target product obtained, which are very difficult to remove and the achievable yields deteriorate. See aslo Ref 4.

 Identifications:

1H NMR (Estimated) for Dipymetitrone

Adverse Reports:

Nothing available.

Others:

The readers are welcome to share their views.

References:

1. Geller, T.; A process for preparing dithiin-tetracarboximiden. WO2012028588A1

2. Seitz, T.; et. al. Verwendung von dithiin-tetracarboximiden zum bekämpfen phytopathogener pilze. WO2010043319A1

3. Draber, W.; et. al. 1, 4 dithiin-2,3,5,6-tetracarboximides and process for their preparation. US3364229A

4. Valla, A.; et. al. Atypical Oxidation Reaction by Thionyl Chloride: Easy Two-Step Synthesis of N-Alkyl-1,4-dithiines. Syn Comm 2006, 36(23), 3591-3597. (FMO only) [It reports mechanism for reaction involving thionly chloride].

1 2 3