125116-23-6

Basic information

• Product Name: METCONAZOLE
• Synonyms: 5-(4-CHLOROPHENYLMETHYL)-2,2-DIMETHYL-1-(1H-1,2,4-TRIAZOL-1-YLMETHYL)CYCLOPENTANOL;METCONAZOLE;CARAMBA;(1RS,5RS;1RS,5RS)-5-(4-chlorobenzyl)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol;Cyclopentanol, 5-(4-chlorophenyl)methyl-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)-;metconazole (bsi,pa iso);metaconazole
• CAS NO: 125116-23-6
• Molecular Formula: C₁₇H₂₂ClN₃O
• Molecular Weight: 319.83
• Mol File: 125116-23-6.mol
• Article Data: 17

Chemical Properties

• Melting Point: 111.5°C
• Boiling Point: 285°C (rough estimate)
• Flash Point: 237.5 °C
• Appearance: /
• Density: 1.1888 (rough estimate)
• Vapor Pressure: 1.33E-09mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• PKA: 13.82±0.60(Predicted)
• BRN: 8333708
• CAS DataBase Reference: METCONAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: METCONAZOLE(125116-23-6)
• EPA Substance Registry System: METCONAZOLE(125116-23-6)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-51/53
• Safety Statements: 60
• RIDADR: UN3077 9/PG 3
• WGK Germany: 2
• Hazardous Substances Data: 125116-23-6(Hazardous Substances Data)

Usage

Uses

Metconazole is an conazole based fungicide used for the control of black sigatoka disease on banana. Metconazole acts primarily as an inhibitor of ergosterol biosynthesis which interferes with the syn thesis of fungal cell membranes.

Definition

ChEBI: A member of the class of cyclopentanols carrying 1,2,4-triazol-1-ylmethyl and 4-chlorobenzyl and geminal dimethyl substituents at positions 1, 2 and 5 respectively. Used to control a range of fungal infections including alternaria, rusts, fusarium and sept ria diseases.

InChI:InChI=1/C17H22ClN3O/c1-16(2)8-7-14(9-13-3-5-15(18)6-4-13)17(16,22)10-21-12-19-11-20-21/h3-6,11-12,14,22H,7-10H2,1-2H3

Upstream product

• 288-88-0 1,2,4-Triazole 
• 872-50-4 1-methyl-pyrrolidin-2-one 
• 115851-28-0 5-[(4-chlorophenyl)methyl]-2,2-dimethylcyclopentanone 
• 3084-53-5 trimethylsulphonium bromide 
• 75-65-0 tert-butyl alcohol 
• 75-85-4 tert-Amyl alcohol 
• 143764-90-3 cis-7-[(4-chlorophenyl)methyl]-4,4-dimethyl-1-oxaspiro[2.4]heptane 
• 31608-26-1 2-(4-chlorobenzylidene)cyclopentanone 
• 120-92-3 cyclopentanone 
• 104-88-1 4-chlorobenzaldehyde 
• 131984-21-9 2,2-dimethyl-5-(4-chlorobenzylidene)cyclopentanone 
• 76085-56-8 N-(dichloromethyl)methanimidamide hydrochloride 
• 18986-75-9 5-benzylidene-2,2-dimethyl-cyclopentanone 
• 100-52-7 benzaldehyde 

Downstream Products

• 199392-01-3 (cis/trans)-2-[5-(4-chlorobenzyl)-1-hydroxy-2,2-dimethyl-cyclopentylmethyl]-2,4-dihydro-[1,2,4]triazole-3-thione 

Relevant articles and documents

Synthesis method of metconazole

The invention discloses a synthesis method of metconazole, and relates to the technical field of pesticides. Comprising the following steps: carrying out condensation reaction on 2, 2-dimethyl cyclopentanone and benzaldehyde to obtain 5-benzal-2, 2-dimethyl cyclopentanone; then, carrying out epoxidation reaction to obtain 7-benzal-4, 4-dimethyl-1-oxaspiro [2, 4] heptane; the preparation method comprises the following steps: carrying out a ring-opening reaction to obtain 5-benzal-2, 2-dimethyl-1-(1H-1, 2, 4-triazole-1-yl methyl) cyclopentanol, and then carrying out a ring-opening reaction to obtain 5-benzal-2, 2-dimethyl-1-(1H- The preparation method comprises the following steps: carrying out a reduction reaction on 2, 2-dimethyl-1-(1H-1, 2, 4-triazole-1-yl methyl) cyclopentanol to obtain 5-benzyl-2, 2-dimethyl-1-(1H-1, 2, 4-triazole-1-yl methyl And then carrying out a chlorination reaction to obtain metconazole. The 2, 2-dimethylcyclopentanone and benzaldehyde are used as raw materials, condensation, reduction, epoxidation, ring opening and chlorination are sequentially performed, the raw materials are cheap, easy to obtain, light in environmental load, green, clean and environmentally friendly, the yield of the obtained metconazole product is high, and the metconazole product has potential industrial production value.

A NOVEL FORM OF METCONAZOLE, A PROCESS FOR ITS PREPARATION AND USE OF THE SAME

A crystalline modification I of 5- (4-chlorobenzyl) -2, 2-dimethyl-1- (1H-1, 2, 4-triazol-1-ylmethyl) cyclopentanol (metconazole) is provided. The crystalline modification is characterized, for example by exhibiting at least 3 of the following reflexes, in any combination, as 2θ ± 0.2 degree in an X-ray powder diffractogram (X-RPD) recorded using Cu-Kα radiation at 25℃ : 2θ = 10.3 ± 0.2 (1) 2θ = 15.8 ± 0.2 (4) 2θ = 20.6 ± 0.2 (5) 2θ = 22.2 ± 0.2 (6) 2θ = 23.3 ± 0.2 (7). A method of preparing the crystalline modification, compositions comprising the crystalline modification and its use in controlling fungal infestations are also provided.

Preparation method of metconazole

The invention relates to a new method for preparing metconazole. The method comprises the following steps: performing reaction on 4,4-dimethyl-7-(4-chlorobenzyl)-1-oxo-spiro[2,4]heptane of a formula (1) and hydrazine hydrate of a formula (2) to produce a compound of formula (3) as shown in the specification, and reacting with N-dichloromethamidine of a formula (4) to prepare a metconazole compoundof a formula (5). According to the method, the process is simple, the raw materials are easy to obtain, the cost is relatively low and few three wastes are produced; furthermore, the defect of generation of 1,3,4-triazole isomer is overcome, the content and the yield of the target product metconazole are increased, the content can reach to 95 percent or more, and the method is suitable for industrialized production.