2,6-Dichloroisonicotinic acid Chemical Properties

Melting point:

209-212 °C(lit.)

Boiling point:

437.8±40.0 °C(Predicted)

Density 

1.612±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

2.63±0.10(Predicted)

color 

White to Brown

Water Solubility 

insoluble

InChI

InChI=1S/C6H3Cl2NO2/c7-4-1-3(6(10)11)2-5(8)9-4/h1-2H,(H,10,11)

InChIKey

SQSYNRCXIZHKAI-UHFFFAOYSA-N

SMILES

C1(Cl)=NC(Cl)=CC(C(O)=O)=C1

CAS DataBase Reference

5398-44-7(CAS DataBase Reference)

NIST Chemistry Reference

4-Pyridinecarboxylic acid, 2,6-dichloro-(5398-44-7)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

2,6-Dichloroisonicotinic acid Usage And Synthesis

Chemical Properties

off-white to beige or light brownish powder

Uses

2,6-Dichloroisonicotinic acid is a derivative of isonicotinic acid (I821760). Treatment of oat cultivars using 2,6-dichloroisonicotinic acid results in an increased accumulation of avenathramide. 2,6-Dichloroisonicotinic acid is a well known inducer of plant resistance and induces the transcription of ZmNAC100 transcription factor.

Definition

ChEBI: A member of the class of pyridines that is isonicotinic acid which is substituted by chlorine at positions 2 and 6.

Agricultural Uses

The best characterized synthetic inducer of resistance, 2,6-dichloroisonicotinic acid and its methyl ester (both are referred to as INA) were the first synthetic compounds reported to activate a phenocopy of bonafide systemic acquired resistance (SAR). 2,6-dichloroisonicotinic acid was used as an abiotic resistance inducer against bacterial spot disease of tomato caused by Xanthomonas perforans. INA was found to protect cucumber, tobacco, arabidopsis, sugar beet, bean, rose, barley, and rice from several pathogens[1].

Synthesis

The general procedure for the synthesis of 2,6-dichloroisonicotinic acid from citrazinic acid was as follows: citrazinic acid (10.35 g, 66.7 mmol) and tetraethylammonium chloride (11.05 g, 66.7 mmol) were suspended in phosphorochloride (20 mL, in excess) and the reaction was heated for 18 hr at 130 °C, followed by warming up to 145 °C to continue the reaction for 2 hr. Upon completion of the reaction, the mixture was cooled to room temperature and slowly poured into crushed ice (150 g) for quenching. The reaction mixture was extracted with ethyl acetate (3 x 100 mL), the organic phases were combined and dried over anhydrous magnesium sulfate. The organic phase was concentrated under reduced pressure to afford the white solid product 2,6-dichloroisonicotinic acid 11.34 g in 89% yield. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 7.85 (s, 2H), 13.90 (br s, OH).

Mode of action

In tobacco, salicylic acid (SA) and 2,6-dichloroisonicotinic acid (INA) induce the same nine classes of genes (including the PR genes) that are expressed systemically after tobacco mosaic virus (TMV) infection. In contrast to many other abiotic inducers of PR gene expression and enhanced disease resistance, such as polyacrylic acid and thiamine, INA does not stimulate the accumulation of SA or its glucoside in treated tobacco plants. The strong correlation between biological activity and the ability to bind and inhibit catalase suggests that the physiological effects of INA, SA, and their active analogs are mediated by the same mechanism of action: inhibition of catalase's ability to degrade H₂0₂[2].

References

[1] S. Chandrashekar, S. Umesha. “2,6-Dichloroisonicotinic acid enhances the expression of defense genes in tomato seedlings against Xanthomonas perforans.” Physiological and Molecular Plant Pathology 86 (2014): Pages 49-56.
[2] Uwe Conrath. “Two inducers of plant defense responses, 2,6-dichloroisonicotinec acid and salicylic acid, inhibit catalase activity in tobacco.” Proceedings of the National Academy of Sciences of the United States of America 92 16 1 (1995): 7143–7.

2,6-Dichloroisonicotinic acid(5398-44-7)Related Product Information

• 1,2-Dichloroethane
• 2,6-Dichloro-5-fluoronicotinic acid
• Sodium dichloroisocyanurate
• 3-Chloroisonicotinic acid
• Isonicotinic acid
• DICHLOROISOCYANURIC ACID
• Diisopropylammonium dichloroacetate
• 2-Chloro-4-pyridinecarboxylic acid
• 1,3-Dichloro-1,3,5-triazinetrione,sodium salt
• METHYL 2,6-DICHLOROISONICOTINATE
• 2,6-Dichloroisonicotinic acid tert-butyl ester,2,6-Dichloroisonicotinic Acid t-butyl ester
• 2-BROMO-3,5-DICHLOROISONICOTINIC ACID
• 2,5-DICHLOROISONICOTINIC ACID
• 2,3-DICHLOROISONICOTINIC ACID
• 3,5-Dichloroisonicotinic acid(3,5-Dichloropyridine-4-carboxylic acid),3,5-DICHLOROISONICOTINIC ACID
• 2,6-Dichloropyridine
• 2,3,5,6-Tetrachloropyridine-4-carboxylic acid
• Ethyl 2,6-dichloroisonicotinate