82200-72-4

Basic information

• Product Name: Triadimenol B
• Synonyms: (1S,2R)-1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol;Triadimenol B;1H-1,2,4-Triazole-1-ethanol, beta-(4-chlorophenoxy)-alpha-(1,1-dimethylethyl)-, (alphar,betar)-rel-
• CAS NO: 82200-72-4
• Molecular Formula: C₁₄H₁₈ClN₃O₂
• Molecular Weight: 295.76462
• Mol File: 82200-72-4.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 465.4°C at 760 mmHg
• Flash Point: 235.3°C
• Appearance: /
• Density: 1.24g/cm³
• Vapor Pressure: 1.84E-09mmHg at 25°C
• Refractive Index: 1.579
• CAS DataBase Reference: Triadimenol B(CAS DataBase Reference)
• NIST Chemistry Reference: Triadimenol B(82200-72-4)
• EPA Substance Registry System: Triadimenol B(82200-72-4)

Safety Data

• Hazardous Substances Data: 82200-72-4(Hazardous Substances Data)

Usage

General Description

Triadimenol B is a fungicide belonging to the class of triazole chemicals used to control a wide range of fungal diseases in crops. It acts as a systemic fungicide by inhibiting the production of ergosterol, an essential component of fungal cell membranes. Triadimenol B is effective against a variety of fungal pathogens, including powdery mildew, rusts, and leaf spots, in crops such as cereals, grapes, and vegetables. It is commonly applied as a spray or seed treatment to protect plants from fungal infections and improve crop yield and quality. However, it is important to use triadimenol B carefully and according to label instructions to minimize its potential impact on non-target organisms and the environment.

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/t12-,13+/m1/s1

Upstream product

• 43121-43-3 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one 
• 288-88-0 1,2,4-Triazole 
• 102690-38-0 (2S,3S)-2-tert-Butyl-3-(4-chloro-phenoxy)-oxirane 
• 1193-00-6 sodium 4-chlorophenolate 
• 27521-49-9 cis-2-bromo-3-tert-butyloxirane 
• 27521-49-9 trans-2-bromo-3-tert-butyloxirane 
• 630-19-3 pivalaldehyde 
• 30263-65-1 1,1-dibromo-3,3-dimethylbutan-2-one 
• 30263-71-9 2-chloro-3-tert-butyloxirane 
• 7664-93-9 sulfuric acid 
• 555-31-7 aluminum isopropoxide 

Downstream Products

• 89497-64-3 1R,2R-1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl) butan-2-ol 
• 89497-65-4 1S,2S-1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl) butan-2-ol 
• 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.