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HomeProduct name list2,6-Dichloroisonicotinic acid

2,6-Dichloroisonicotinic acid

Synonym(s):2,6-Dichloroisonicotinic acid

  • CAS NO.:5398-44-7
  • Empirical Formula: C6H3Cl2NO2
  • Molecular Weight: 192
  • MDL number: MFCD00234147
  • EINECS: 611-076-5
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-15 19:00:21
2,6-Dichloroisonicotinic acid Structural

What is 2,6-Dichloroisonicotinic acid?

Chemical properties

off-white to beige or light brownish powder

The Uses of 2,6-Dichloroisonicotinic acid

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.

What are the applications of Application

2,6-Dichloropyridine-4-carboxylic acid is employed in asymmetric synthesis of (S)-(?)-acromelobic acid and biological studies of plant pathogen resistance.

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].

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.

Properties of 2,6-Dichloroisonicotinic acid

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)
CAS DataBase Reference 5398-44-7(CAS DataBase Reference)
NIST Chemistry Reference 4-Pyridinecarboxylic acid, 2,6-dichloro-(5398-44-7)

Safety information for 2,6-Dichloroisonicotinic acid

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for 2,6-Dichloroisonicotinic acid

InChIKey SQSYNRCXIZHKAI-UHFFFAOYSA-N
SMILES C1(Cl)=NC(Cl)=CC(C(O)=O)=C1

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