2,6-Dichloroisonicotinic acid

Bezeichnung:2,6-Dichloroisonicotinic acid

CAS-Nr5398-44-7

Englisch Name:2,6-Dichloroisonicotinic acid

CBNumberCB6110923

SummenformelC6H3Cl2NO2

Molgewicht192

MOL-Datei5398-44-7.mol

2,6-Dichloroisonicotinic acid physikalisch-chemischer Eigenschaften

Schmelzpunkt	209-212 °C(lit.)
Siedepunkt	437.8±40.0 °C(Predicted)
Dichte	1.612±0.06 g/cm3(Predicted)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit	soluble in Methanol
Aggregatzustand	powder to crystal
pka	2.63±0.10(Predicted)
Farbe	White to Brown
Wasserlöslichkeit	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 Datenbank	5398-44-7(CAS DataBase Reference)
NIST chemische Informationen	4-Pyridinecarboxylic acid, 2,6-dichloro-(5398-44-7)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36-37/39
WGK Germany	3
HazardClass	IRRITANT
HS Code	29333990

Gefahreninformationscode (GHS)

2,6-Dichloroisonicotinic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
off-white to beige or light brownish powder
Verwenden
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.
Landwirtschaftliche Anwendung
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].
Einzelnachweise
[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.

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