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

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

Uses

Used in Agricultural Industry:
Triadimenol is used as a systemic agricultural fungicide for the control of powdery mildews, rusts, and Rhynchosporium in cereals. It is also utilized as a cereal seed protectant, providing early season control of foliar diseases and protection against seed-and soil-borne diseases.
Used in Cereal Seed Treatment:
Triadimenol is employed as a cereal seed treatment to control various diseases such as loose smut, stinking smut, root rot, and others in wheat, barley, corn, and sorghum. It has shown more than 90% effectiveness when used in specific dosages for seed treatment.
Used in Control of Cereal Diseases:
Triadimenol is used to control diseases like rust, powdery mildew, sheath blight, and others in wheat and rice, leading to a significant increase in yield.
Used in Other Crops:
Triadimenol is also used on vines, hops, coffee, tomatoes, vegetables, fruit, tobacco, sugar cane, and ornamentals, mainly against powdery mildews, rusts, and various leaf spot diseases.
Chemical Properties:
Triadimenol has a melting point of 112 °C and a vapor pressure of 1 × 10^-3 Pa at 20 °C. It is soluble in organic solvents such as cyclohexane (40%), isopropanol (15%), methylene chloride (10%), and toluene (4%). In water, its solubility is 0.12g/L. Triadimenol is stable in neutral or weak acid medium but tends to break down when boiled in a strong acidic medium.
Safety and Regulatory Information:
Triadimenol is registered for use in EU countries and the U.S., with maximum allowable residue levels set for the compound. It is teratogenic, inducing cranial nerve and ganglia abnormalities in a rat post-implantation whole embryo culture model at certain concentrations. In vivo, triadimenol induces embryotoxicity in rats and rabbits when administered orally at specific doses. Embryonic exposure to triadimenol also induces embryonic mortality and affects fertility and offspring gender ratio in medaka fish (Oryzias latipes).

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:

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

• 7664-93-9 sulfuric acid 
• 555-31-7 aluminum isopropoxide 
• 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 

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 Combinations Of Active Ingredients

The present invention relates to novel active compound combinations comprising, firstly, at least one known compound of the formula (I) in which R1 and A have the meanings given in the description and, secondly, 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.

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.

Synergistic Fungidical Active Substance Combinations

The present invention relates to novel active substance combinations which contain spiroxamine, which is known, a known azole and a known carboxamide and which are very suitable for controlling undesired 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.

Wood preservatives

Wood preservatives having biocidal properties which include quaternary ammonium compounds of general formula (I): wherein R1 is a C8-18-alkyl group or an optionally substituted benzyl group, R2 is a C8-18-alkyl group, R3 is a C1-4-alkyl group or a group of the formula —[CH2—CH2—O]n—H, R4 is a C1-4-alkyl group, n is a number from 0.5 to 8, preferably from 1 to 5, and A?is the anion of an organic carboxylic acid which contains 2 to 12 C atoms and carries at least one hydroxyl, amino or sulfonic acid group. The wood preservatives also penetrate deeply into the wood without the use of pressure, and have only a mild corrosive action on metals. Furthermore, a process for treating timbers with these compositions, concentrates for the preparation thereof, the use of new and known quaternary ammonium compounds in wood preservatives and new quaternary ammonium compounds and their use as biocides.

Iminoacetic acid amides and their use as pest control agents

PCT No. PCT/EP96/04345 Sec. 371 Date Apr. 15, 1998 Sec. 102(e) Date Apr. 15, 1998 PCT Filed Oct. 7, 1996 PCT Pub. No. WO97/14673 PCT Pub. Date Apr. 24, 1997Iminoacetamides of the formula (I) in which A represents a single bond or optionally substituted alkylene, Q represents oxygen or sulphur, R1 represents respectively optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclyl, R2 represents respectively optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, R3 represents hydrogen or respectively optionally substituted alkyl, alkenyl, alkinyl or cycloalkyl, R4 represents respectively optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclcyl a process for their preparation, pesticidal compositions containing them, and their use for controlling pests.

Microbicidal benzotriazoles

Novel benzotriazoles of the formula STR1 in which R, X1, X2, X3, X4 and Y have the meanings given in the description, and their acid addition salts and metal salt complexes, a process for the preparation of these substances and their use as microbicides in crop protection and in material protection.

Halogen alkenyl azolyl microbicides

Novel halogenoalkenyl-azolyl derivatives of the formula STR1 in which R1 represents optionally substituted alkyl, optionally substituted alkenyl, optionally substituted cycloalkyl, optionally substituted aryl or represents optionally substituted heteroaryl, R2 represents alkyl, halogenoalkyl, 1-hydroxyalkyl, 2-hydroxyalkyl, 1-hydroxyhalogenalkyl, 1-alkenyl or 2-alkenyl, X1 represents fluorine, chlorine, bromine or iodine, X2 represents fluorine, chlorine, bromine or iodine, and Y represents nitrogen or a CH group, and addition products thereof with acids or metal salts are very active as microbicides in plant protection and in the protection of materials.

Acylated 5-aminopyrazoles and the use thereof to combat animal parasites

The present invention relates to new acylated 5-aminopyrazoles of the formula (I) STR1 in which R1, R2, R3, R4 and R5 have the meaning given in the description, to processes for their preparation and to their use as pesticides.