DICHLONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H4Cl2O2
Molecular Weight	227.044
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

ClC1=C(Cl)C(=O)C2=CC=CC=C2C1=O

InChI

InChIKey=SVPKNMBRVBMTLB-UHFFFAOYSA-N

InChI=1S/C10H4Cl2O2/c11-7-8(12)10(14)6-4-2-1-3-5(6)9(7)13/h1-4H

HIDE SMILES / InChI

Molecular Formula	C10H4Cl2O2
Molecular Weight	227.044
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://sitem.herts.ac.uk/aeru/ppdb/en/Reports/1129.htm | http://pmep.cce.cornell.edu/profiles/fung-nemat/aceticacid-etridiazole/dichlone/fung-prof-dichlone.html | https://www.ncbi.nlm.nih.gov/pubmed/23294304

Dichlone is a fungicide without regulatory approval for use in the EU. It has a low aqueous solubility and is not mobile and, based on its chemical properties, it is unlikely to leach to groundwater. It is not persistent in most soil systems. Dichlone has a moderate mammalian toxicity. Dichlone is an inhibitor of the DNA methyltransferase 3A/3L complex.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
DNA (cytosine-5)-methyltransferase 3A 3 Target ID: CHEMBL3108652 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23294304	Inhibitor 8504	0.46 µM [EC50]
Indoleamine 2,3-dioxygenase 20 Target ID: CHEMBL4685 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18318466	Inhibitor 8504	280.0 nM [IC50]
DNMT3A2/3L complex 1 Target ID: CHEMBL3137291 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25406944	Inhibitor 8504	0.5 µM [IC50]
DNA (cytosine-5)-methyltransferase 1 10 Target ID: CHEMBL1993 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25406944	Inhibitor 8504	1.6 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pseudomonas infections 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20923439	Primary		Basic research	Unknown Approved Use Unknown
Helicobacter infection 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16359837	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Bacterial growth response to photoactive quinones.	2010-10-07	20923439
Reactions of germenes with various naphthoquinones controlled by substituent effects.	2010-02-28	20148219
Methionine aminopeptidases from Mycobacterium tuberculosis as novel antimycobacterial targets.	2010-01-29	20142044
Reaction of naphthoquinones with substituted nitromethanes. Facile synthesis and antifungal activity of naphtho[2,3-d]isoxazole-4,9-diones.	2010-01-01	19926280
Toxicology in the fast lane: application of high-throughput bioassays to detect modulation of key enzymes and receptors.	2009-12	20049205
Kinetics of jack bean urease inhibition by 2,3-dichloro-1,4-naphthoquinone. Elucidation of the mechanism: redox cycling and sulfhydryl arylation.	2009-10	19621983
Magnetic particle-based hybrid platforms for bioanalytical sensors.	2009	22574058
New sensitive kinetic spectrophotometric methods for determination of omeprazole in dosage forms.	2009	20140076
Charge transfer interaction of 4-acetamidophenol (paracetamol) with 2,3-dichloro-1,4-naphthoquinone: a study in aqueous ethanol medium by UV-vis spectroscopic and DFT methods.	2008-12-01	18343717
3,3-Dimethyl-1,2,3,4,6,11-hexa-hydro-benzo[d]naphtho[2,3-b]furan-1,6,11-trione.	2008-07-19	21203239
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.	2008-04	18324785
Hydrides in liquid chloroaluminates.	2007-12-06	17994723
Antibacterial activity of Tabebuia impetiginosa Martius ex DC (Taheebo) against Helicobacter pylori.	2006-04-21	16359837
Interaction of 2,3-dichloro-1,4-naphthoquinone with n-butylamine in halocarbon solvents.	2005-06	15863041
Development and validation of spectrophotometric methods for determination of fluoxetine, sertraline, and paroxetine in pharmaceutical dosage forms.	2005-03-12	15759724
Selective growth-inhibiting effects of compounds identified in Tabebuia impetiginosa inner bark on human intestinal bacteria.	2005-02-23	15713033
Study of a reaction between 2,3-dichloro-1,4-naphthoquinone and N,N'-diphenyl thiourea involving an EDA adduct as intermediate.	2004-06	15147710
Reduction of nitroaromatic pesticides with zero-valent iron.	2004-01	14575737
Synthesis and cytotoxicity of 6,11-dihydro-pyrido- and 6,11-dihydro-benzo[2,3-b]phenazine-6,11-dione derivatives.	2003-04-17	12659757
Synthesis and cytotoxicity evaluation of 2-amino- and 2-hidroxy-3-ethoxycarbonyl-N-substituted-benzo[f]indole-4,9-dione derivatives.	2003-04-03	12628676
[Reactions of isopropyl-alkylamine with 2,3-dichloro-1,4-naphthoquinone and 2,3-dichloro-1,4-naphthoquinone/acetaldehyde].	2003-02	12641324
2-(Pyrrolidin-1-yl)-1,4-naphthoquinone and 2-phenylsulfanyl-3-(pyrrolidin-1-yl)-1,4-naphthoquinone.	2002-12	12466620
[Reactions of trialkylamine compounds with 2,3-dichloro-1,4-naphthoquinone].	2002-09	12369457
[Reactions between dialkylamine drugs, 2,3-dichloro-1,4-naphthoquinone and acetaldehyde].	2002-08	12227191
Synthesis, electrochemical and spectral properties of some omega-N-quinonyl amino acids.	2002	12025875
New quinone-amino acid conjugates linked via a vinylic spacer.	2001	11452981
Novel N-quinonyl amino acids and their transformation to 3-substituted p-isoxazinones.	2001	11332448
2-chloro-3-substituted-1,4-naphthoquinone inactivators of human cytomegalovirus protease.	1999-10-04	10522707

Patents

Sample Use Guides

In Vivo Use Guide

LD50 = 1300 mg/kg (rat)

Route of Administration: Oral

In Vitro Use Guide

Dichlone inhibited murine catalytic complex Dnmt3A/3L with EC50 value of 0.46 uM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:48:00 GMT 2025` Edited by `admin` on `Mon Mar 31 17:48:00 GMT 2025`
Record UNII	C28BKZ2J9A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DICHLONE

Common Name

English

PHYGON

Preferred Name

English

2,3-DICHLORO-1,4-NAPHTHALENEDIONE

Systematic Name

English

DICHLONE [ISO]

Common Name

English

USR-604

Code

English

2,3-DICHLORO-1,4-NAPHTHOQUINONE

Systematic Name

English

DICHLONE [HSDB]

Common Name

English

DICHLONE [MI]

Common Name

English

NSC-537

Code

English

Classification Tree Code System Code

EPA PESTICIDE CODE

29601