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

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

Used in Cereal Production:
Diniconazole is used as a fungicide for controlling leaf and ear diseases in cereals, ensuring a healthy crop yield and preventing losses due to fungal infections.
Used in Vine Cultivation:
In vine cultivation, Diniconazole is utilized as a fungicide to manage powdery mildew, a common fungal disease that can significantly impact grape quality and production.
Used in Rose Cultivation:
Diniconazole serves as a fungicide in rose cultivation, targeting rust and black spot diseases, which can cause severe damage to the plant and affect its aesthetic appeal.
Used in Peanut Cultivation:
In peanut cultivation, Diniconazole is used as a fungicide to control leaf spot, a fungal disease that can lead to reduced crop yields and quality.
Used in Banana Production:
Diniconazole is employed as a fungicide in banana production to combat Sigatoka disease, a destructive fungal infection that can cause significant losses in banana plantations.
Used in Coffee Cultivation:
In coffee cultivation, Diniconazole is used to manage Uredinales, a group of rust fungi that can severely affect coffee plant health and productivity.
Used in Fruit, Vegetable, and Ornamental Plant Production:
Diniconazole is also used as a fungicide in the production of various fruits, vegetables, and ornamental plants to protect them from fungal infections and ensure healthy growth and high-quality produce.

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 
• 53631-70-2 d,l-norephedrine hydrochloride 
• 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 
• 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 
• 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 

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 mixture

A composition comprising effective amounts ofa) a carbamate of the formula I where T is CH or N, n is 0, 1 or 2 and R is halogen, C1-C4-alkyl or C1-C4-haloalkyl, it being possible for the radicals R to be different if n is 2, andc) a compound III selected from the group consisting of the oxime ether carboxylate IIIa, the oxime ether carboxamide IIIb and the methoxyacrylate IIIc and optionally an oxime ether (II) and/or an azole (IV) as defined in the specification which exhibits a synergistically enhanced fungicidal effect is described.

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

Fungicidal mixture, comprising a) an oxime ether carboxamide of the formula I STR1 where R is hydrogen or halogen and b) an azole derivative II selected from the group of the compounds II.1 to II.17 1-[(2RS,4RS;2RS,4SR)-4-bromo-2-(2,4-dichlorophenyl)-tetrahydrofuryl]-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-triazolylmethyl)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-1-yl)hexan-2-ol (II.9) (1RS,5RS;1RS,5SR)-5-(4-chlorobenzyl)-2,2-dimenthyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol [sic] (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-triazolyl)-propyl 1,1,2,2-tetrafluoroethyl ether (II.14) and (E)-1-[1-[[4-chloro-2-(trifluoromethyl)phenyl]imino]-2-propoxyethyl]-1H-imidazole (II.15) (RS)-2,4'-difluoro-α-(1H-1,2,4-triazol-1-ylmethyl)-benzhydryl alcohol (II.16) 2-p-chlorophenyl-2-(1H-1,2,4-triazol-1-ylmethyl)-hexanenitrile (II.17) 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.

Fungicide compositions

Compositions of azole fungicides exhibiting reduced eye irritation are prepared by replacing a significant portion of the hydrocarbon solvent with a combination of propylene glycol and a long chain fatty alcohol.

Method for producing an optically active azolyl-α β-unsaturated alcohol

The present invention relates to a method for producing optically active alcohol derivatives, which are useful as fungicides, herbicides or plant growth regulators, represented by the formula, STR1 by carrying out the asymmetric reduction of a ketone compound represented by the formula, STR2 with a boron hydride-reducing agent modified with an optically active amino alcohol represented by the formula, STR3 and also relates to the boron hydride type compound obtained by reacting the above optically active amino alcohol with a boron hydride compound and its production method.

Asymmetrically modified boron hydride type compound, a production method thereof, and a method for producing an optically active alcohol derivative by the use thereof

The present invention relates to an asymmetrically modified borohydride type compound obtained by reacting an optically active amino alcohol represented by the formula, STR1 or its salt with an acid with a borohydride compound; its production method; and a method for producing an optically active alcohol derivative useful as fungicides, herbicides or plant growth regulators and represented by the formula, STR2 which comprises asymmetrically reducing a ketone compound represented by the formula, STR3 with the asymmetrically modified borohydride type compound.

Fungicide compositions

A fungicide composition having reduced eye irritation comprising in percent by weight based on the weight of the composition 5-50% of an azole fungicide which irritates the eye in combination with an aromatic hydrocarbon, 20-40% propylene glycol, 1-20% fatty alcohol having at least 10 carbon atoms, 10-40% surfactant and less than about 20% aromatic hydrocarbon.

Optical isomer of triazolylpentenols, and their production and use as fungicide, herbicide and/or plant growth regulant

This invention relates to a triazolyl alcohol derivative having an optical activity of (-) or (+) and represented by the general formula (I), STR1 wherein X represents a hydrogen atom or a chlorine atom and the asterisk indicates an asymmetric carbon atom, a process for preparing same, and a fungicide containing same as active ingredient.