55219-65-3

Basic information

• Product Name: Triadimenol
• Synonyms: 2-(4-chlorophenoxy)-1-tert-butyl-2-(1h-1,2,4-triazole-1-yl)-ethano;2-(4-Chlorophenoxy)-1-tert-butyl-2-(1H-1,2,4-triazole-1-yl)ethanol;a-(4-chlorophenoxy)-b-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol;BAY KWG 0519;bayfrdanew;baykwg0519;baytan15;baytantf3479b
• CAS NO: 55219-65-3
• Molecular Formula: C₁₄H₁₈ClN₃O₂
• Molecular Weight: 295.76
• EINECS: 259-537-6
• Product Categories: INSECTICIDE;Pesticide
• Mol File: 55219-65-3.mol
• Article Data: 19

Chemical Properties

• Melting Point: 112-117°
• Boiling Point: 465.4 °C at 760 mmHg
• Flash Point: 2 °C
• Appearance: powder
• Density: 1.2990 (rough estimate)
• Vapor Pressure: 1.84E-09mmHg at 25°C
• Refractive Index: 1.5270 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 13.29±0.20(Predicted)
• Water Solubility: A 62 mg l-1 (20 °C); B 33 mg l-1(20 °C)
• Merck: 13,9667
• BRN: 616470
• CAS DataBase Reference: Triadimenol(CAS DataBase Reference)
• NIST Chemistry Reference: Triadimenol(55219-65-3)
• EPA Substance Registry System: Triadimenol(55219-65-3)

Safety Data

• Hazard Codes: Xn,F,T
• 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
• Hazardous Substances Data: 55219-65-3(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 55219-65-3 differently. You can refer to the following data:
1. 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.
2. Systemic agricultural fungicide; cereal seed protectant.
3. 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.
4. 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.

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).

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.

InChI:InChI=1/C14H18ClN3O2/c1-14(2,3)12(19)13(18-9-16-8-17-18)20-11-6-4-10(15)5-7-11/h4-9,12-13,19H,1-3H3

Upstream product

• 43121-43-3 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one 
• 1193-00-6 sodium 4-chlorophenolate 
• 7664-93-9 sulfuric acid 
• 555-31-7 aluminum isopropoxide 

Downstream Products

• 117956-17-9 copper(II) 2,3,4,5,6-pentachlorophenolate (3,3-dimethyl-1-(1-H-1,2,4-triazolyl-1)-1-(4-chlorophenoxy)butan-2-ol) 
• 117956-16-8 copper(II) 2,4,5-trichlorophenolate (3,3-dimethyl-1-(1-H-1,2,4-triazolyl-1)-1-(4-chlorophenoxy)butan-2-ol) 
• 94786-44-4 1-(4-chlorophenoxy)-3,3-dimethyl-2-[N-(2,3-dihydro-2,2-dimethyl-benzofuran-7-oxy-carbonyl)methylcarbamoyloxy]-1-(1,2,4-triazol-1-yl)butane 
• 112438-90-1 Toluene-4-sulfonic acid (S)-1-[(S)-(4-chloro-phenoxy)-[1,2,4]triazol-1-yl-methyl]-2,2-dimethyl-propyl ester 
• 112439-43-7 Toluene-4-sulfonic acid (S)-1-[(R)-(4-chloro-phenoxy)-[1,2,4]triazol-1-yl-methyl]-2,2-dimethyl-propyl ester 

Relevant articles and documents

Carbonyl reduction of triadimefon by human and rodent 11β- hydroxysteroid dehydrogenase 1

11β-Hydroxysteroid dehydrogenase 1 (11β-HSD1) catalyzes the conversion of inactive 11-oxo glucocorticoids (endogenous cortisone, 11-dehydrocorticosterone and synthetic prednisone) to their potent 11β-hydroxyl forms (cortisol, corticosterone and prednisolone). Besides, 11β-HSD1 accepts several other substrates. Using rodent liver microsomes and the unspecific inhibitor glycyrrhetinic acid, it has been proposed earlier that 11β-HSD1 catalyzes the reversible conversion of the fungicide triadimefon to triadimenol. In the present study, recombinant human, rat and mouse enzymes together with a highly selective 11β-HSD1 inhibitor were applied to assess the role of 11β-HSD1 in the reduction of triadimefon and to uncover species-specific differences. To further demonstrate the role of 11β-HSD1 in the carbonyl reduction of triadimefon, microsomes from liver-specific 11β-HSD1-deficient mice were employed. Molecular docking was applied to investigate substrate binding. The results revealed important species differences and demonstrated the irreversible 11β-HSD1-dependent reduction of triadimefon. Human liver microsomes showed 4 and 8 times higher activity than rat and mouse liver microsomes. The apparent Vmax/ Km of recombinant human 11β-HSD1 was 5 and 15 times higher than that of mouse and rat 11β-HSD1, respectively, indicating isoform-specific differences and different expression levels for the three species. Experiments using inhibitors and microsomes from 11β-HSD1-deficient mice indicated that 11β-HSD1 is the major if not only enzyme responsible for triadimenol formation. The IC50 values of triadimefon and triadimenol for cortisone reduction suggested that exposure to these xenobiotica unlikely impairs the 11β-HSD1-dependent glucocorticoid activation. However, elevated glucocorticoids during stress or upon pharmacological administration likely inhibit 11β-HSD1-dependent metabolism of triadimefon in humans.

Synergistic Active Compound Combinations Comprising Phenyltriazoles

The present invention relates to novel active compound combinations comprising, firstly, at least one known compound of the formula (I) in which R1 and R2 have the meanings given in the description. and at least one further known active compound from groups (2) to (27) listed in the description, which combinations are highly suitable for controlling animal pests such as insects and unwanted acarids and also phytopathogenic fungi.

Pyrazolyl benzyl ether derivatives containing a fluoromethoxyimino group and use thereof as pesticides

The invention relates to novel pyrazolyl benzyl ethers, to a plurality of processes for their preparation and to their use for controlling harmful organisms.