83657-24-3

Basic information

• Product Name: Diniconazole
• Synonyms: MITAZOLE;SPOTLESS;(e)-(+-)-imethylethyl);1h-1,2,4-triazole-1-ethanol,beta-((2,4-dichlorophenyl)methylene)-alpha-(1,1-d;diniconazole(stereochemistryunspecified);orthospotless;s-3308-10;s-3308l
• CAS NO: 83657-24-3
• Molecular Formula: C₁₅H₁₇Cl₂N₃O
• Molecular Weight: 326.22
• Product Categories: INSECTICIDE;NULL
• Mol File: 83657-24-3.mol
• Article Data: 10

Chemical Properties

• Melting Point: 134~156℃
• Boiling Point: 501.1 °C at 760 mmHg
• Flash Point: 256.8 °C
• Appearance: White powder
• Density: 1.32
• Vapor Pressure: 7.35E-11mmHg at 25°C
• Refractive Index: 1.592
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 12.89±0.20(Predicted)
• Water Solubility: 4 mg/L at 25 ℃
• CAS DataBase Reference: Diniconazole(CAS DataBase Reference)
• NIST Chemistry Reference: Diniconazole(83657-24-3)
• EPA Substance Registry System: Diniconazole(83657-24-3)

Safety Data

• Hazard Codes: T:Toxic
• Hazardous Substances Data: 83657-24-3(Hazardous Substances Data)

Usage

Uses

Diniconazole is used to control leaf and ear diseases in cereals, powdery mildew in vines, rust and black spot in roses, leaf spot in peanuts, Sigatoka disease in bananas, and Uredinales in coffee. It is also used on fruit, vegetables and ornamentals.

Metabolic pathway

Diniconazole is a mixture of four isomers, which are derived from a chiral carbon atom and a double bond in the molecule. Diniconazole M [( E)-( S)-1-(2 ,4-dichlorophenyl)-4,4-dimethyl-2-1(H -1,2,4-triazol-l-yl)pent- 1-en-3-ol] is more potent than diniconazole. The major metabolic pathways of diniconazole involve oxidative attack on the pentenol side chain to give products which may form conjugates. In mammals, sulfurcontaining metabolites may be formed.

Degradation

Diniconazole is stable to heat, light and moisture. It undergoes photolysis and irradiation of a solution in methanol with light from a high-pressure mercury lamp for 8 hours gave three major and seven minor products, 2- 11 (Scheme 1). The major photoproduct was identified as the 2-isomer (2). The other major products (5 and 6) were formed by photooxidation of the CHOH group to a carbonyl group. When diniconazole was irradiated as a thin film under ultraviolet light (254 nm), the major product was identified as the Z-isomer. On the surface of a sandy loam soil, under the same irradiation conditions rapid degradation occurred with the formation of 2, 5 and 6. A thin film of diniconazole applied to a glass plate degraded very slowly in the dark. When the plate was placed in the sunhght, 70% of the applied material disappeared after 5 days exposure and isomerisation occurred to give the Z-isomer (65%). The DT50 in sunlight was 2.5 days. Under ultraviolet light (254 mn), the Z-isomer was formed after 15 minutes irradiation, and after 5 hours 90% of the material had isomerised (Dureja and Walia, 1992).

InChI:InChI=1/C15H17Cl2N3O/c1-15(2,3)14(21)13(20-9-18-8-19-20)6-10-4-5-11(16)7-12(10)17/h4-9,14,21H,1-3H3/b13-6+

Upstream product

• 48115-38-4 norepinephrine 
• 76715-39-4 (E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)-1-penten-3-one 
• 60-29-7 diethyl ether 
• 6853-14-1 2-dimethylamino-1-phenylethanol 
• 2202-68-8 (S)-2-dimethylamino-1-phenylethanol 
• 103-69-5 N-ethyl-N-phenylamine 
• 874-42-0 2,4-dichlorobenzaldeyhde 
• 58905-32-1 3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butanone 
• 552-79-4 (-)-N-methylephedrine 
• 76713-90-1 1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-pent-1-en-3-ol 
• 17605-71-9 2-dimethylamino-1-phenyl-propan-1-ol 
• 100-61-8 N-methylaniline 
• 53631-70-2 d,l-norephedrine hydrochloride 

Downstream Products

• 101179-53-7 (E)-(R)-1-(2,4-dichlorophenyl)-4,4-dimethyl 2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol 
• 101179-53-7 (S)-diniconazole 

Relevant articles and documents

Synthetic process of diniconazole

The invention discloses a synthetic process of diniconazole. The synthetic process of diniconazole includes steps of compounding pyrazolone hydrochloride by taking nitrogen triazole as raw materials; hydrolyzing pyrazolone hydrochloride and preparing pyrazolone; condensing pyrazolone to prepare ketene; water-washing and acidifying ketene to prepare ketene sulfate; hydrolyzing and reducing the ketene sulfate to obtain diniconazole. The synthetic process of diniconazole has the advantages of simple synthetic process, wide raw material source, low price, and high yield of the product diniconazole.

Fungicide mixtures

A fungicidal mixture comprising a) an oxime ether of the formula I where the substituents have the following meanings: X is oxygen or amino (NH); Y is CH or N; Z is oxygen, sulfur, amino (NH) or C1-C4-alkylamino (N-alkyl); R′ is alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkylmethyl, or, if desired, substituted benzyl; a) an oxime ether of the formula I where the substituents have the following meanings: X is oxygen or amino (NH); Y is CH or N; Z is oxygen, sulfur, amino (NH) or C1-C4-alkylamino (N—C1-C4-alkyl); R′ is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C2-C6-haloalkenyl, C3-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkylmethyl, or is benzyl which can be partially or fully halogenated and/or can have attached to it one to three of the following radicals: cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C1-C4-alkylthio; and at least one compound from groups b)-c): b.1) the oxime ether carboxylate of the formula IIa, b.2) the oxime ether carboxamide of the formula IIb, b.3) the methoxyacrylate of the formula IIc, c) one or more azole derivatives in a synergistically active amount.

Fungicidal mixtures

A fungicidal mixture containing a) the oxime ether carboxamide of the formula I STR1 and b) an azole derivative II selected from the group of compounds II.1 to II.16 1-[(2RS,4RS;2RS,4SR)-4-bromo-2-(2,4-dichlorophenyl)tetra-hydrofuryl]-1H-1,2,4-triazole (II.1) 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (II.2) (±)-4-chloro-4-[4-methyl-2-(1H-1,2,4-triazol-1-yl-methyl)-1,3-dioxolan-2-yl]phenyl 4-chlorophenyl ether (II.3) (E)-(R,S)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol (II.4) (Z)-2-(1H-1,2,4-triazol-1-ylmethyl)-2-(4-fluorophenyl)-3-(2-chlorophenyl)oxirane (II.5) 4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazolyl methyl)butyronitrile (II.6) 3-(2,4-dichlorophenyl)-6-fluoro-2-(1H-1,2,4-triazol-1-yl)quinazolin-4(3H)-one (II.7) bis(4-fluorophenyl)(methyl)(1H-1,2,4-triazol-1-yl-methyl)silane (II.8) (R,S)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-l-yl)-hexan-2-ol (II.9) (1RS,5RS;1RS,5SR)-5-(4-chlorobenzyl)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (II.10) N-propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl]-imidazole-1-carboxamide (II.11) (±)-1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole (II.12) (R,S)-1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol (II.13) (±)-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl) propyl 1,1,2,2-tetrafluoroethyl ether (II.14) (E)-1-[1-[[4-chloro-2-(trifluoromethyl)phenyl]imino]-2-propoxyethyl]-1H-imidazole (II.15) and (RS)-2,4'-difluoro-α-(1H-1,2,4-triazol-1-yl-methyl)benzhydryl alcohol (II.16) in a synergistically active amount is described.