Triadimenol
Chemical properties Uses Toxicity Preparation method- Product Name
- Triadimenol
- CAS No.
- 55219-65-3
- Chemical Name
- Triadimenol
- Synonyms
- 1-(4-CHLOROPHENOXY)-3,3-DIMETHYL-1-(1H-1,2,4-TRIAZOL-1-YL)BUTAN-2-OL;b-(4-Chlorophenoxy)-a-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol;SAMET;uk199;SUMMIT;BAYTAN;TRIADIM;kwg0519;triafol;baytoan
- CBNumber
- CB3495832
- Molecular Formula
- C14H18ClN3O2
- Formula Weight
- 295.76
- MOL File
- 55219-65-3.mol
Triadimenol Property
- Melting point:
- 112-117°
- Boiling point:
- 465.4±55.0 °C(Predicted)
- Density
- 1.2990 (rough estimate)
- vapor pressure
- A 6 x l0-7 Pa (20 °C); B 4 x l0-7 Pa (20 °C)
- refractive index
- 1.5270 (estimate)
- Flash point:
- 2 °C
- storage temp.
- 2-8°C
- solubility
- DMSO (Slightly), Methanol (Slightly)
- Water Solubility
- A 62 mg l-1 (20 °C); B 33 mg l-1(20 °C)
- pka
- 13.29±0.20(Predicted)
- form
- Solid
- color
- White to Off-White
- Merck
- 13,9667
- BRN
- 616470
- LogP
- 2.900
- CAS DataBase Reference
- 55219-65-3(CAS DataBase Reference)
- NIST Chemistry Reference
- Triadimenol(55219-65-3)
- EPA Substance Registry System
- Triadimenol (55219-65-3)
Safety
- Hazard Codes
- Xn,F,T
- Risk Statements
- 22-52/53-36-20/21/22-11-23-20/22
- Safety Statements
- 22-61-36-26-45
- RIDADR
- 2588
- WGK Germany
- 2
- RTECS
- KK2200000
- HazardClass
- 6.1(b)
- PackingGroup
- III
- HS Code
- 29339900
- Hazardous Substances Data
- 55219-65-3(Hazardous Substances Data)
- Toxicity
- LD50 in male, female rats (mg/kg): 1161, 1105 orally; >5000 dermally, 24-hr; LD50 in quail: >10000 mg/kg (Frohberger)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H302Harmful if swallowed
H362May cause harm to breast-fed children
H411Toxic to aquatic life with long lasting effects
- Precautionary statements
-
P202Do not handle until all safety precautions have been read and understood.
P260Do not breathe dust/fume/gas/mist/vapours/spray.
P263Avoid contact during pregnancy/while nursing.
P273Avoid release to the environment.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P308+P313IF exposed or concerned: Get medical advice/attention.
N-Bromosuccinimide Price
- Product number
- 46138
- Product name
- Triadimenol
- Purity
- mixture of diastereomers A and B
- Packaging
- 250mg
- Price
- $74.5
- Updated
- 2025/07/31
- Product number
- 38878
- Product name
- Triadimenol
- Purity
- certified reference material, TraceCERT?
- Packaging
- 50MG
- Price
- $99.3
- Updated
- 2025/07/31
- Product number
- 24216
- Product name
- Triadimenol
- Purity
- ≥98%
- Packaging
- 250mg
- Price
- $34
- Updated
- 2024/03/01
- Product number
- 24216
- Product name
- Triadimenol
- Purity
- ≥98%
- Packaging
- 500mg
- Price
- $63
- Updated
- 2024/03/01
- Product number
- C375060
- Product name
- β-(4-Chlorophenoxy)-α-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol(MixtureofDiastereomers)(Triadimenol)
- Packaging
- 10g
- Price
- $375
- Updated
- 2021/12/16
Triadimenol Chemical Properties,Usage,Production
Chemical properties
The pure triadimenol is white, tasteless fine crystalline powder. m.p.: 112 ° C, vapor pressure: 1 × 10 -3 Pa (20 ° C). Solubility in organic solvents: cyclohexane 40%, isopropanol 15%, methylene chloride 10%, toluene 4%; Solubility in water: 0.12g / L. Stable in neutral or weak acid medium, easy to break down when boiled in strong acidic medium.
Uses
It is a systemic broad-spectrum seed treatment fungicide which can kill pathogens attached to the internal and external surface of seed. It works through the inhibition of fungal ergosterol biosynthesis. It’s used on cereal grains to control powdery mildew and smut diseases such as loose smut, stinking smut and root rot on wheat, loose smut, rust, leaf stripe disease and net blotch etc on barley, and it is more than 90% effective when 100kg of seeds are treated with 30 ~ 50g of 25% DS. It is more than 90% effective when 100kg of seeds are treated with 42 ~ 75g of 25% DS to control smut on corn and sorghum head smut. If 100kg of seeds are treated with 30g of triadimenol and 5g of furidazol, it will be 92% to 100% effective for the control of loose smut, stripe disease, net blotch and root rot on spring barley , loose smut, stinking smut, snow mold on winter wheat, and leaf stripe disease, loose smut on spring oat.
Triadimenol is a broad-spectrum fungicide with high efficiency and low toxicity. It is used on wheat and rice to control rust, powdery mildew, sheath blight and other diseases, and has a significant yield increasing effect. It can be also used as a cereal seed treatment and for the control of cereal smut.
Toxicity
The acute oral toxicity LD50 in rats was 1161 mg / kg (female), 1105 mg / kg (male). The acute oral toxicity LD50 in mice was 1300 mg / kg (male & female). No effect dose for dogs and rats during 90 days feeding test: 600mg / kg • d. The acute inhalation The LC50 in goldfish and rainbow trout was 10～15mg/L and 23.5mg/L respectively (both 96 hours). The LD50 in quail was > 1000mg / kg. No effect on bees.
Preparation method
Mostly, using triadimefon as the starting material , triadimenol is prepared through different reduction processes.
1. Reduction by hydrogen in the presence of a catalyst and any polar solvent, or reduction by aluminum isopropoxide in the presence of a solvent:
2. Reduction by borohydride in the presence of any polar solvent.
3. Reduction by formamidine sulfinic acid and alkali metal hydroxide in the presence of any polar solvent:
4. Reduction by using formic acid - triethylamine adduct as a reducing agent:
Description
Triadimenol is a metabolite of triadimefon , a broad-spectrum chiral triazole fungicide, that is formed by reduction of a carbonyl group to the corresponding alcohol. It is teratogenic, inducing cranial nerve and ganglia abnormalities in a rat post-implantation whole embryo culture model when used at concentrations ranging from 12.5 to 125 μM. In vivo, triadimenol induces embryotoxicity in rats and rabbits when administered orally at doses of 100 and 40 mg/kg, respectively. Embryonic exposure to triadimenol (3-3,000 μg/L) induces embryonic mortality as well as decreases fertility and increases the number of female offspring in medaka fish (O. latipes).
Uses
β-(4-Chlorophenoxy)-α-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol is a agricultural fungicide that is systemically active against powdery mildews and rusts of grains.
Uses
Systemic agricultural fungicide; cereal seed protectant.
Uses
Triadimenol is used for the control of powdery mildews, rusts and Rhynchosporium in cereals, and also as a seed treatment to control bunt, smut and other cereal diseases. It is also used on vines, hops, coffee, tomatoes, vegetables, fruit, tobacco, sugar cane, ornamentals and other crops, mainly against powdery mildews, rusts and various leaf spot diseases.
Definition
ChEBI: 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 O1 by a 4-chlorophenyl group. A fungicide for cereals, beet and brassicas used to control a range of diseases including powdery mildew, ru ts, bunts and smuts.
Agricultural Uses
Fungicide: Triadimenol is used to control seed-and soil-borne diseases and to provide early season control of foliar diseases. It is applied to seeds of barley, corn, oats, rye, sorghum and wheat and also to fruits, vegetables and ornamentals. Registered for use in EU countries . Registered for use in the U.S. U.S. Maximum Allowable Residue Levels for Triadimenol
Trade name
BAYFIDAN®; BAYFRDAN EW®; BAY KWG 0519®; BAYTAN® SEED TREATMENT; BAYTAN 30® FUNGICIDE; PROTEGE ALLEGIANCE BAYTAN®; SPINNAKER®; SUMMIT®; TRIADIMENOL®; TRIAFOL®; TRIAPHOL®
Metabolic pathway
When triadimenol is irradiated by UV light in methanol solution, two major degradation products are identified as 1-(4-chlorophenoxy)-3,3-dimethylbutan-2-one and 1-phenoxy-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan- 2-ol. When a spray deposit on apple leaves is exposed outdoors to natural sunlight, the only product detected is the butanone metabolite. The butanone metabolite has very low fungicidal activity against apple powdery mildew, whereas the butanol metabolite gives some control of infection.
Degradation
When a methanolic solution of triadimenol (1) in borosilicate glass apparatus was irradiated by a medium pressure mercury lamp for 20 days, 50% of the triadimenol was photodegraded. The products identified were 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H -1,2,4-triazol-1-yl)butan-2- one (major product) (2), 4-chlorophenol (3) and 1-phenoxy-3,3-dimethyl- 1-(1H-1,2,4-triazol-1-yl)butan-2-ol(4 ). When triadimenol was irradiated as a solid deposit, 55% of the parent compound was recovered after 18 days and the same products were identified. Losses may be accounted for by volatilisation or photodegradation (Clark and Watkins, 1986) (Scheme 1). The only major product detected 33 days after triadimenol had been applied to apple tree leaf surfaces exposed to light outdoors was 2.
References
[1] QIUXUAN SHEN. Enantioselective metabolism of triadimefon and its chiral metabolite triadimenol in lizards[J]. Ecotoxicology and Environmental Safety, 2017, 143: Pages 159-165. DOI: 10.1016/j.ecoenv.2017.05.024
[2] E MENEGOLA. In vitro teratogenic potential of two antifungal triazoles: triadimefon and triadimenol.[J]. In Vitro Cellular & Developmental Biology. Animal, 2000, 36 2: 88-95. DOI: 10.1290/1071-2690(2000)036<0088:ivtpot>2.0.co;2
[3] SZU-HUNG CHU Pei J C Pei Han Liao. Developmental exposures to an azole fungicide triadimenol at environmentally relevant concentrations cause reproductive dysfunction in females of medaka fish[J]. Chemosphere, 2016, 152: Pages 181-189. DOI: 10.1016/j.chemosphere.2016.02.078
Triadimenol Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Triadimenol manufacturers
- Product
- Triadimenol 55219-65-3
- Price
- US $0.00/KG
- Min. Order
- 100KG
- Purity
- 98
- Supply Ability
- 200TONS
- Release date
- 2024-07-17
- Product
- Triadimenol 55219-65-3
- Price
- US $10.70/KG
- Min. Order
- 10KG
- Purity
- 99%
- Supply Ability
- 10000kg
- Release date
- 2024-08-20
- Product
- Triadimenol 55219-65-3
- Price
- US $10.70/KG
- Min. Order
- 10KG
- Purity
- 99%
- Supply Ability
- 10000kg
- Release date
- 2024-08-20