PROHEXADIONE

PROHEXADIONE Property

Melting point:

98-99°

Boiling point:

454.9±45.0 °C(Predicted)

Density 

1.330±0.06 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

Chloroform: soluble

form 

A solid

pka

2.66±0.25(Predicted)

LogP

-1.098 (est)

Hazard and Precautionary Statements (GHS)

PROHEXADIONE Chemical Properties,Usage,Production

Uses

Prohexadione (BX-112 free acid) is a plant growth regulator. Prohexadione inhibits gibberellin biosynthesis of plants[1][2].

Definition

ChEBI: Prohexadione is a 4-oxo monocarboxylic acid that is cyclohexanecarboxylic acid which is substituted by oxo groups at positions 3 and 5, and by a propanoyl group at position 4. A plant growth regulator, it is used (commonly as the corresponding calcium salt, known as prohexadione-calcium) as an anti-lodging agent in small-grain cereals. It has a role as an agrochemical, a plant growth regulator and a gibberellin biosynthesis inhibitor. It is a 4-oxo monocarboxylic acid and a beta-triketone. It is a conjugate acid of a prohexadione(2-).

Enzyme inhibitor

This plant growth regulator (FWfree-acid = 178.19 g/mol), also named 3- hydroxy-5-oxo-4-propionylcyclohex-3-ene-1-carboxylic acid, inhibits the biosynthesis of growth active gibberellins (GAs), thereby reducing longitudinal shoot growth. Prohexadione resembles 2-oxoglutaric acid, the co-substrate the dioxygenases that catalyze hydroxylation steps in late stages of GA biosynthesis. Its primary target of is 3b hydroxylation, thereby reducing levels of GA1 (the highly active form) and bringing about theaccumulation of its immediate precursor (inactive). Targets: flavanone 3-dioxygenase flavonol synthase; and gibberellin biosynthesis.

References

[1] Paulson GS, et al. Effect of a plant growth regulator prohexadione-calcium on insect pests of apple and pear. J Econ Entomol. 2005 Apr;98(2):423-31. DOI:10.1093/jee/98.2.423
[2] Vavilala DT, et al. Prohexadione, a plant growth regulator, inhibits histone lysine demethylases and modulates epigenetics. Toxicol Rep. 2014 Nov 4;1:1152-1161.
[3] Feng N, et al. Prohexadione-calcium alleviates saline-alkali stress in soybean seedlings by improving the photosynthesis and up-regulating antioxidant defense. Ecotoxicol Environ Saf. 2021 Sep 1;220:112369. DOI:10.1016/j.ecoenv.2021.112369
[4] McGrath MJ, et al. Evidence that prohexadione-calcium induces structural resistance to fire blight infection. Phytopathology. 2009 May;99(5):591-6. DOI:10.1094/PHYTO-99-5-0591