Bitertanol is a broad-spectrum triazole fungicide that is active against a variety of fungi, including V. inaequalis and V. pirina, which are responsible for apple and pear scab, respectively, as well as S. mors-uvae and P. ribis, which are responsible for American gooseberry mildew and leaf spot in black currants, respectively. It is active against isolates of V. inaequalis (MICs = 0.6 and 1 μg/ml) but repeated use leads to resistance and cross-resistance (MICs = 9.8-13 μg/ml for bitertanol-resistant isolates). Bitertanol inhibits the cytochrome P450 (CYP450) isoform CYP3A4 (IC50 = 2.74 μM) and inhibits androgenic activity induced by the androgen receptor agonist DHT in a yeast two-hybrid assay (IC50 = 79.85 μM). In rats, bitertanol (10-300 mg/kg, i.p.) increases operant responding on one- and five-minute fixed interval schedules with no effect on motor activity.
Bitertanol is a foliar-applied triazole fungicide used to protect tropical and subtropical crops in agriculture, in particular bananas. Bitertanol has effects on behavior that are similar to those of psychomotor stimulants.
Bitertanol is used as a seed treatment on winter wheat and barley
and as a foliar treatment to control diseases on bananas, ornamentals, fruit
and vegetables.
ChEBI: 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol is a member of the class of triazoles that is 3,3-dimethyl-1-(1,2,4-triazol-1-yl)butane-1,2-diol substituted at position O-1 by a biphenyl-4-yl group. It is a member of biphenyls, an aromatic ether, a member of triazoles and a secondary alcohol.
Fungicide: A fungicide used to control a variety of diseases.
Used as control for prunes when drying. Not currently
registered in the U.S. or EU countries (pending). Used
in many European, South American, Far Eastern and
African countries, a well as in Australia for use on beans
(all types) and various ornamentals. More than 20 global
suppliers.
BAYCOR®; BAY KWG 0599®; BAYMATSPRAY
®; BILOXAZOL®; KWG 0599®; SIBUTOL®,
(with Fuberidazole)
Bitertanol is a mixture of two diastereoisomeric pairs and this complicates
its metabolism, each biotransfonnation affording a mixture of isomers.
Metabolism has been studied under environmental conditions and in
plants and mammals. Degradation in soil and sediments is slow and only
small quantities of products (other than CO2 and bound residues) are
produced. Most information is available for mammals in which metabolism
occurs mainly by oxidative routes followed by conjugation. The
information presented below is derived from the UK MAFF Pesticide
Safety Directorate (PSD, 1994).
The hydrolytic stability of [14C]bitertanowl as measured at pH 4, 7 and 9
over 30 days at 25 and 40 °C. No decomposition was observed and the
DT50 was estimated at >1 year at 25 °C.
Aqueous solutions of [14C-triazole]-and [14C-biphenyl]-bitertanol were
irradiated for 48 and 72 hours, respectively, using a mercury arc lamp
under conditions somewhat exceeding natural sunlight. Calculated DT50
values were 38-52 hours and an estimated environmental DT50 was considered
to be 11 days. 4-Hydroxybiphenyl (4) and 1,2,4-triazole (5) were
identified as major photolysis products accounting for 12% and 53% of
the radioactivity, respectively. These are shown in Scheme 1. At least six
minor products were detected but these were not identified.
Very little degradation occurred under soil surface photolysis conditions
simulating natural sunlight. No discrete products were detected.
Bound residue increased to only 5% of the total over 35 days.
