Chemical Properties
White Solid
Uses
A triazole fungicide showing potential carcinogenicity
Uses
Ergosterol biosynthesis inhibitor. Fungicide.
Uses
Tebuconazole used as a seed dressing is effective against various
smut and bunt diseases of cereals. Used as a spray it controls numerous
pathogens in various crops: rust species, powdery mildew, Rhyncosporum
secalis, Sqtoria spp., Pyrenophora spp., Fusarium spp. in cereals,
Mycosphaerella spp. in bananas, Pucciniu spp. and Sclerufium roIfsii in
peanuts.
Definition
ChEBI: 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol is a tertiary alcohol that is pentan-3-ol substituted by a 4-chlorophenyl, methyl, methyl, and a 1H-1,2,4-triazol-1-ylmethyl at positions 1, 4, 4 and 3 respectively. It is a member of monochlorobenzenes, a member of triazoles and a tertiary alcohol.
Agricultural Uses
Fungicide, Plant growth regulator: Used as a seed treatment against smuts and bunts
of cereals; as a foliar spray against diseases of cereal, peanuts,
oilseed rape, grapes, bananas, stone fruit, and pome
fruit. Registered for use in EU countries. Registered for
use in the U.S.
Trade name
BAY®-HWG 1608; BAYER®-HWG-1608
CORAIL®; ELITE®; FOLICUR®; FOLITRAZOLE®;
GAUCHO®; HORIZON®; HWG 1608®; LYNX-1.2®;
PREVENTOL® RAXIL (tebuconazole + metalaxyl);
SILVACUR®; TEBUJECT®; WOLMAN®; WOODLIFE®
Mechanism of action
Systemic with protective, curative and eradicant action. Disrupts membrane function. Sterol biosynthesis inhibitor.
Synthesis
To a 250 mL three-necked flask was added 120 g of N,N-dimethylformamide, followed by 40 g of pentaconazole isomer, 2.0 g of potassium hydroxide, and 1.0 g of 3-bromomethyl-1-(4-chlorophenyl)-4,4-dimethyl-3-propanol.The reaction mixture was heated to 150 °C and maintained at this temperature for 4 hours. Sampling and analysis during the reaction showed that the purity of tebuconazole was 99.8% and the isomer content was 0.2%. Upon completion of the reaction, the target product tebuconazole was obtained by removing the solvent, followed by slurry treatment with water and toluene, and finally filtered to give 38.6 g of the target product tebuconazole in 96.5% yield and 98.5% product purity.
Metabolic pathway
Tebuconazole is degraded in soils and does not accumulate. In plants the
metabolites were mainly compounds containing triazole, and in mammals
tebuconazole was rapidly metabolised and excreted in urine and
faeces.
Degradation
Tebuconazole is stable to elevated temperatures. Under sterile conditions
it is stable to hydrolysis in water. It is hydrolysed slowly with a DTS0 of
>1 year.
Only two products were formed by irradiation of a suspension of tebuconazole
in water with UV light (>280 nm). These were the hydrochloride
(3) and 1,2,4-triazole (2). The expected product in which chlorine was replaced by hydroxyl could not be isolated. In organic solvents a number
of products were formed. Several products (3, 4, 5, 6, 7, 8, 9, 12, 13, 14)
were isolated from benzene after 72 hours irradiation (>280 nm). In a
number of cases products isolated from photolysis in benzene were
formed by reactions in which the solvent participated and involved
addition of a benzene molecule (4, 9, 5, 6). On irradiation in methylene
chloride and methanol, 4-chloracetophenone (10) and acetophenone (11)
were also identified in addition to starting material and 1,2,4-triazole
(Wamhoff et al., 1994).
Pesticide Type
Fungicide; Plant Growth Regulator
![4H-1,2,4-Triazole-4-ethanol, α-[2-(4-chlorophenyl)ethyl]-α-(1,1-dimethylethyl)-](/CAS/20210305/GIF/97821-63-1.gif)
