107534-96-3

Basic information

• Product Name: Tebuconazole
• Synonyms: LYNX;Lynx 1.2;LYNX(R);MATADOR;ELITE;ELITE(R);FOLICUR;folicur 1.2 ec
• CAS NO: 107534-96-3
• Molecular Formula: C₁₆H₂₂ClN₃O
• Molecular Weight: 307.82
• EINECS: 403-640-2
• Product Categories: FUNGICIDE;Pesticide;Aromatics;Heterocycles;Inhibitors;Pesticide intermediates;Pesticides intermediate
• Mol File: 107534-96-3.mol
• Article Data: 35

Chemical Properties

• Melting Point: 102-105°C
• Boiling Point: 476.9 °C at 760 mmHg
• Flash Point: 100 °C
• Appearance: Powder
• Density: 1.25
• Vapor Pressure: 7.6E-10mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: 0-6°C
• PKA: 13.70±0.29(Predicted)
• Water Solubility: 32 mg/L at 20 ºC
• Merck: 14,9092
• CAS DataBase Reference: Tebuconazole(CAS DataBase Reference)
• NIST Chemistry Reference: Tebuconazole(107534-96-3)
• EPA Substance Registry System: Tebuconazole(107534-96-3)

Safety Data

• Hazard Codes: Xn;N,N,Xn
• Statements: 22-51/53-63
• Safety Statements: 2-22-36/37-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• RTECS: XZ4803270
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 107534-96-3(Hazardous Substances Data)

Usage

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

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 107534-96-3 differently. You can refer to the following data:
1. A triazole fungicide showing potential carcinogenicity
2. Fungicide.
3. 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.
4. Ergosterol biosynthesis inhibitor. Fungicide.

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?

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).

InChI:InChI=1/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

Synthetic route

tebuconazole (97821-63-1) → tebuconazole (107534-96-3)

Conditions	Yield
With 3-(bromomethyl)-1-(4-chlorophenyl)-4,4-dimethylpentan-3-ol; potassium hydroxide In N,N-dimethyl-formamide at 150℃; for 4h; Reagent/catalyst; Solvent; Temperature;	96.5%
With sodium hydroxide In 1-methyl-pyrrolidin-2-one; dichloromethane; water	93.8%
With sodium hydroxide In 1-methyl-pyrrolidin-2-one; dichloromethane; water	84.9%

1,2,4-Triazole (288-88-0) + 2-[2-(4-chlorophenyl)ethyl]-2-(1,1-dimethylethyl)ethylene oxide (80443-63-6) → tebuconazole (107534-96-3)

Conditions	Yield
With 18-crown-6 ether; potassium hydroxide at 108 - 128℃; for 15h; Temperature; Reagent/catalyst;	95%
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In N,N-dimethyl-formamide at 80 - 102℃; Reagent/catalyst;	95.6%
With potassium hydroxide In neat (no solvent) at 130℃; for 7h; Reagent/catalyst; Temperature; Time;	94%
With potassium hydroxide In diethylene glycol dimethyl ether at 100 - 120℃; for 11h; Temperature;	92.1%

sodium triazole (41253-21-8) + 1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8) → tebuconazole (107534-96-3)

Conditions	Yield
With trimethyl sulfoxonium chloride; potassium hydroxide In dimethyl sulfoxide at 40 - 120℃;	91%

C3H4BrMgN3 + 1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8) → tebuconazole (107534-96-3)

Conditions	Yield
Stage #1: C3H4BrMgN3; 1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one In tetrahydrofuran for 2h; Green chemistry; Stage #2: With acetic acid In tetrahydrofuran; water for 1h; Green chemistry;	78%

1,2,4-Triazole (288-88-0) + 2-(4-chloro-phenyl-ethyl)-2-tert-butyl-oxirane + (E)-3,3'-(diazene-1,2-diyl)bis(2-methylpropanenitrile) (764-28-3) → tebuconazole (107534-96-3)

Conditions	Yield
With sodium hydroxide In 1-methyl-pyrrolidin-2-one; benzene

tebuconazole (107534-96-3) + citric acid (77-92-9) → (RS)-1-(4-chlorophenyl)-4,4-dimethyl-3-[(1H-1,2,4-triazol-4-ium)-1-ylmethyl]pentan-3-ol dihydrogen citrate

Conditions	Yield
In methanol at 20℃;	99%

L-Tartaric acid (87-69-4) + tebuconazole (107534-96-3) → (RS)-1-(4-chlorophenyl)-4,4-dimethyl-3-[(1H-1,2,4-triazol-4-ium)-1-ylmethyl]pentan-3-ol L-tartrate

Conditions	Yield
In methanol at 20℃;	99%

tebuconazole (107534-96-3) → C16H21(2)HClN3O

Conditions	Yield
With deuteromethanol; silver carbonate at 50 - 80℃;	99%

18α-glycyrrhizic acid + tebuconazole (107534-96-3) → C42H62O16*C16H22ClN3O

Conditions	Yield
In methanol Reflux;	98%

dodecylbenzene-sulphonic acid (47221-31-8) + tebuconazole (107534-96-3) → (RS)-1-(4-chlorophenyl)-4,4-dimethyl-3-[(1H-1,2,4-triazol-4-ium)-1-ylmethyl]pentan-3-ol 4-dodecylbenzenesulfonate

Conditions	Yield
In methanol at 20℃;	98%

methanesulfonic acid (75-75-2) + tebuconazole (107534-96-3) → (RS)-1-(4-chlorophenyl)-4,4-dimethyl-3-[(1H-1,2,4-triazol-4-ium)-1-ylmethyl]pentan-3-ol methanesulfonate

Conditions	Yield
In methanol at 20℃;	98%

1,8-dibromooctane (4549-32-0) + tebuconazole (107534-96-3) → C40H60Cl2N6O2(2+)*2Br(1-)

Conditions	Yield
In acetonitrile at 80℃; for 72h;	94%

tebuconazole (107534-96-3) + benzenesulfonic acid (98-11-3) → (RS)-1-(4-chlorophenyl)-4,4-dimethyl-3-[(1H-1,2,4-triazol-4-ium)-1-ylmethyl]pentan-3-ol benzenesulfonate

Conditions	Yield
In methanol at 20℃;	93%

1,4-dibromo-butane (110-52-1) + tebuconazole (107534-96-3) → C36H52Cl2N6O2(2+)*2Br(1-)

Conditions	Yield
In acetonitrile at 80℃; for 72h;	93%

toluene-4-sulfonic acid (104-15-4) + tebuconazole (107534-96-3) → (RS)-1-(4-chlorophenyl)-4,4-dimethyl-3-[(1H-1,2,4-triazol-4-ium)-1-ylmethyl]pentan-3-ol 4-methylbenzenesulfonate

Conditions	Yield
In methanol at 20℃;	92%

2-methoxyacetic acid (625-45-6) + tebuconazole (107534-96-3) → (RS)-1-(4-chlorophenyl)-4,4-dimethyl-3-[(1H-1,2,4-triazol-4-ium)-1-ylmethyl]pentan-3-ol methoxyacetate

Conditions	Yield
In methanol at 20℃;	92%

sodium cis-dichloromalonatopalladate(II) dihydrate + tebuconazole (107534-96-3) → C32H44Cl4N6O2Pd

Conditions	Yield
With potassium tetrachloropalladate(II) In chloroform; water at 20℃; for 3h;	92%

potassium tetrachloroplatinate + tebuconazole (107534-96-3) → trans-bis[1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol]dichloroplatinum

Conditions	Yield
In water; acetone for 48h;	91%

sodium hexachloroplatinate(IV) hexahydrate + tebuconazole (107534-96-3) → trans-bis[1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol]tetrachloroplatinum

Conditions	Yield
In acetone for 72h; Solvent;	90%

1,12-dibromododecane (3344-70-5) + tebuconazole (107534-96-3) → C44H68Cl2N6O2(2+)*2Br(1-)

Conditions	Yield
In acetonitrile at 80℃; for 72h;	90%

1 ,6-dibromohexane (629-03-8) + tebuconazole (107534-96-3) → C38H56Cl2N6O2(2+)*2Br(1-)

Conditions	Yield
In acetonitrile at 80℃; for 72h;	87%

copper(II) acetate monohydrate (6046-93-1) + tebuconazole (107534-96-3) → [Cu((RS)-1-(4-chloro-phenyl)-4,4-dimethyl-3-(1,2,4-triazole-1-ylmethyl)pentan-3-ol)2(CH3COO)2]

Conditions	Yield
for 3h; Reflux;	86%

Upstream product

• 288-88-0 1,2,4-Triazole 
• 764-28-3 (E)-3,3'-(diazene-1,2-diyl)bis(2-methylpropanenitrile) 
• 97821-63-1 tebuconazole 
• 66346-01-8 1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one 
• 119298-82-7 (S)-1-(4-Chloro-phenyl)-4,4-dimethyl-3-((2R,4aR,7R,8aR)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-pentan-3-ol 
• 119364-84-0 (R)-1-(4-Chloro-phenyl)-4,4-dimethyl-3-((2R,4aR,7R,8aR)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-pentan-3-ol 
• 120687-96-9 (R)-2-[2-(4-Chloro-phenyl)-ethyl]-2-hydroxy-3,3-dimethyl-butyraldehyde 
• 120687-99-2 (S)-2-[2-(4-Chloro-phenyl)-ethyl]-2-hydroxy-3,3-dimethyl-butyraldehyde 
• 120687-97-0 (R)-2-[2-(4-Chloro-phenyl)-ethyl]-3,3-dimethyl-butane-1,2-diol 
• 119298-83-8 (S)-2-[2-(4-Chloro-phenyl)-ethyl]-3,3-dimethyl-butane-1,2-diol 
• 92572-79-7 2-(2,2-dimethylpropanoyl)-1,3-oxathiane 
• 6529-53-9 1-(2-bromoethyl)-4-chlorobenzene 
• 41253-21-8 sodium triazole 
• 119298-84-9 Methanesulfonic acid (S)-2-[2-(4-chloro-phenyl)-ethyl]-2-hydroxy-3,3-dimethyl-butyl ester 

Downstream Products

• 80443-41-0 (R)-1-p-chlorophenyl-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol 
• 119364-85-1 (S)-1-p-chlorophenyl-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol 

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Preparation method of tebuconazole midbody and preparation method of tebuconazole

The invention relates to a preparation method of a tebuconazole midbody and a preparation method of tebuconazole. The preparation method of the tebuconazole midbody comprises the following steps of: adding 1-(4-chlorophenyl)-4,4-dimethyl-3-pentanone, trimethylthion chloride or trimethylsulfoxonium bromide, a base and a solvent into a reactor, and carrying out stirring reaction to obtain the tebuconazole midbody; the structural formula of the tebuconazole midbody is as shown in the specification; and the preparation method of the tebuconazole comprises the following steps of: adding triazole salt into the reaction system prepared by the preparation method of the tebuconazole midbody, and carrying out reaction at 110 to 130 DEG C to obtain the tebuconazole. The preparation methods are new routes for synthesizing tebuconazole, are relatively simple in process, easy to get raw materials, relatively low in toxicity of reagents and drugs used in the operation process, mild in reaction conditions and short in time; and compared with conventional methods, the preparation methods are simpler to operate and higher in total yield, so that the synthesis cost is greatly reduced, the three wastes are less, the target products are high in content, and the preparation methods are very suitable for industrial production.