Bitertanol

Bitertanol

Names
IUPAC name 3,3-dimethyl-1-(4-phenylphenoxy)-1-(1,2,4-triazol-1-yl)butan-2-ol
Other names Baycor Biloxazol
Identifiers
CAS Number	55179-31-2
3D model (JSmol)	Interactive image
ChEBI	CHEBI:83851
ChEMBL	ChEMBL1566634
ChemSpider	82759
ECHA InfoCard	100.054.084
EC Number	259-513-5
KEGG	C11258
PubChem CID	91656
CompTox Dashboard (EPA)	DTXSID2037502
InChI InChI=1S/C20H23N3O2/c1-20(2,3)18(24)19(23-14-21-13-22-23)25-17-11-9-16(10-12-17)15-7-5-4-6-8-15/h4-14,18-19,24H,1-3H3 Key: VGPIBGGRCVEHQZ-UHFFFAOYSA-N
SMILES CC(C)(C)C(C(N1C=NC=N1)OC2=CC=C(C=C2)C3=CC=CC=C3)O
Properties
Chemical formula	C20H23N3O2
Molar mass	337.423 g·mol−1
Appearance	colorless
Density	1.16 g·cm−3
log P	4.1
Vapor pressure	0.0000075 mmHg
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H330
Precautionary statements	P260, P264, P270, P271, P284, P301+P317, P304+P340, P316, P320, P330, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Bitertanol is a mixture of four isomers, which are chemical compounds belonging to the triazole and biphenyl derivative classes.

Properties

Bitertanol is a colorless, water-insoluble solid. The commercial product is a 20:80 mixture of the (1RS,2RS)- and (1RS,2SR)-isomers.

• Stereoisomers of bitertanol, showing the Cahn-Ingold-Prelog convention-configuration and content in the technical product
• 
  (1R,2R)-bitertanol (approx. 10%)
• 
  (1S,2S)-Bitertanol (approx. 10%)
• 
  (1R,2S)-Bitertanol (approx. 40%)
• 
  (1S,2R)-Bitertanol (approx. 40%)

It is highly stable toward photolysis and hydrolysis. Its half-life in aqueous suspension is 39.2 days.

Synthesis

Bitertanol can be prepared via a multi-step reaction starting from 3,3-dimethyl-2-butanone: chlorination with elemental chlorine is followed by nucleophilic substitution of the chlorine atom with 4-phenylphenol, bromination with elemental bromine, subsequent nucleophilic substitution with 1,2,4-triazole, and final reduction of the ketone with hydrogen.

Synthesis of Bitertanol

Uses

Bitertanol is used as a fungicide for the preventive or curative treatment of diseases in fruit and vegetable crops, including Venturia species and Monilia laxa in stone fruit, as well as a seed treatment against Fusarium, Septoria, wheat scab, and other pathogens. It was introduced to the market in 1979 by Bayer AG.

Approval

The European Union approved its use as an active substance in plant protection products, effective January 1, 2012, specifically as a fungicide for seed treatment. This approval expired in August 2013.

In European countries such as Germany and Austria, as well as Switzerland, no plant protection products containing this active substance are approved.