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107534-96-3

107534-96-3 Structure

107534-96-3 Structure
IdentificationMore
[Name]

Tebuconazole
[CAS]

107534-96-3
[Synonyms]

1-(4-CHLOROPHENYL)-4,4-DIMETHYL-3-(1H-1,2,4-TRIAZOL-1-YLMETHYL)-3-PENTANOL
A-[2-(4-CHLOROPHENYL)ETHYL]-A-(1,1-DIMETHYLETHYL)-1H-1,2,4-TRIAZOLE-1-ETHANOL
(+/-)-alpha-(2-(4-chlorophenyl)ethyl)-alpha-(1,1-dimethylethyl)-1H-1,2,4-triazol-1-ethanol
ELITE
ELITE(R)
FOLICUR
folicur 1.2 ec
FOLICUR (TM)
GWG 1609
HORIZON
hwg 1608
LYNX
Lynx 1.2
LYNX(R)
MATADOR
RAXIL
RAXIL(R)
TEBUCONAZOL
TEBUCONAZOLE(R)
TERBUCONAZOLE
[EINECS(EC#)]

403-640-2
[Molecular Formula]

C16H22ClN3O
[MDL Number]

MFCD02674797
[Molecular Weight]

307.82
[MOL File]

107534-96-3.mol
Chemical PropertiesBack Directory
[Melting point ]

102-105°C
[Boiling point ]

476.9±55.0 °C(Predicted)
[density ]

1.25
[vapor pressure ]

1.7 x l0-6 Pa (20 °C)
[refractive index ]

1.5800 (estimate)
[Fp ]

100 °C
[storage temp. ]

0-6°C
[solubility ]

Chloroform: Slightly Soluble; Methanol: Slightly Soluble
[form ]

neat
[pka]

13.70±0.29(Predicted)
[color ]

White to Almost white
[Water Solubility ]

32 mg/L at 20 ºC
[Merck ]

13,9176
[Henry's Law Constant]

7.0×104 mol/(m3Pa) at 25℃, HSDB (2015)
[Major Application]

agriculture
cleaning products
cosmetics
environmental
food and beverages
personal care
[InChI]

1S/C16H22ClN3O/c1-15(2,3)16(10-21,20-12-18-11-19-20)9-8-13-4-6-14(17)7-5-13/h4-7,11-12,21H,8-10H2,1-3H3
[InChIKey]

PXMNMQRDXWABCY-UHFFFAOYSA-N
[SMILES]

CC(C)(C)C(CO)(CCc1ccc(Cl)cc1)n2cncn2
[LogP]

3.700
[CAS DataBase Reference]

107534-96-3(CAS DataBase Reference)
[NIST Chemistry Reference]

Tebuconazole(107534-96-3)
[EPA Substance Registry System]

107534-96-3(EPA Substance)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)Health Hazard (GHS08)Environment (GHS09)
GHS07,GHS08,GHS09
[Signal word ]

Warning
[Hazard statements ]

H302-H361d-H410
[Precautionary statements ]

P201-P202-P264-P273-P301+P312-P308+P313
[Hazard Codes ]

Xn;N,N,Xn
[Risk Statements ]

R22:Harmful if swallowed.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R63:Possible risk of harm to the unborn child.
[Safety Statements ]

S2:Keep out of the reach of children .
S22:Do not breathe dust .
S36/37:Wear suitable protective clothing and gloves .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
[RIDADR ]

UN 3077 9/PG 3
[WGK Germany ]

3
[RTECS ]

XZ4803270
[REACH Registrations]

Inactive
[HazardClass ]

9
[PackingGroup ]

III
[HS Code ]

29339900
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Acute Tox. 4 Oral
Aquatic Acute 1
Aquatic Chronic 1
Repr. 2
[Hazardous Substances Data]

107534-96-3(Hazardous Substances Data)
[Toxicity]

bird - domestic,LD50,oral,> 1gm/kg (1000mg/kg),Pesticide Manual. Vol. 9, Pg. 785, 1991.
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Pinacolone-->Tebuconazole-->1,2,4-Triazole-->4H-1,2,4-Triazole-4-ethanol, α-[2-(4-chlorophenyl)ethyl]-α-(1,1-dimethylethyl)--->2-[2-(4-Chlorophenyl)ethyl]-2-(1,1-dimethylethyl)-oxirane-->N,N-Dimethylformamide-->Potassium hydroxide
[Preparation Products]

Seed coating
Questions And AnswerBack Directory
[Description]

Tebuconazole is a trazole fungicide. It is taken up by plants and transported within tissues. It is used as a seed dressing, which works effectively against various smut and bunt diseases of cereals. As foliar spray tebuconazole controls numerous phathogens such as rust species, powdery mildew, and scale in various crops. It is also used to control pests including yellow leaf spot, black spot, net blotch, and Scelerotinia rot.
Tebuconazole can be applied to control above mentioned diseases on cereals (including wheat, barley, oat, rye), grapes, peanuts, vegetables (onions and peas), bananas, sugarcane.
[References]

[1] http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/610.htm
[2] Pesticide residues in food – 1994 Report sponsored jointly by FAQ and WHO
[3] https://www.efsa.europa.eu/en/efsajournal/pub/3485
Hazard InformationBack Directory
[Chemical Properties]

White Solid
[Uses]

A triazole fungicide showing potential carcinogenicity
[Uses]

Ergosterol biosynthesis inhibitor. Fungicide.
[Uses]

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]

4H-1,2,4-Triazole-4-ethanol, α-[2-(4-chlorophenyl)ethyl]-α-(1,1-dimethylethyl)-

97821-63-1

Tebuconazole

107534-96-3

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.
[storage]

Store at -20°C
[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
Spectrum DetailBack Directory
[Spectrum Detail]

Tebuconazole(107534-96-3)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

107534-96-3(sigmaaldrich)
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