Diniconazole

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Diniconazole
Category Antifungal
Catalog number BBF-05840
CAS 83657-24-3
Molecular Weight 326.22
Molecular Formula C15H17Cl2N3O
Purity ≥95%

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Description

Diniconazol is a chemical compound belonging to chlorine group of conazole. It is used as a fungicide. It inhibited lanosterol 14 alpha-demethylation catalyzed by a yeast cytochrome P-450 strongly.

Specification

Related CAS 76714-88-0 (Deleted CAS) 101179-53-7 (Deleted CAS) 1135441-04-1 (Deleted CAS) 70217-36-6 (rac-isomer) 76714-16-4 (Z-isomer)
Synonyms (E)-(±)-β-[(2,4-Dichlorophenyl)methylene]-α-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol; (E)-1-(2,4-Dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol; (E)-β-[(2,4-Dichlorophenyl)methylene]-α-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol; Mixor; Nb 2; Rac-diniconazole; S 3308; S 3308-10; S 3308L; Spotless; Sumi; Sumi 8; Sumi 8-020FS; Sumi 8-12.5WP; XE 779; 1H-1,2,4-Triazole-1-ethanol, β-[(2,4-dichlorophenyl)methylene]-α-(1,1-dimethylethyl)-, (βE)-
Shelf Life Limited shelf life, expiry date on the label
Storage Store at -20°C
IUPAC Name (E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol
Canonical SMILES CC(C)(C)C(C(=CC1=C(C=C(C=C1)Cl)Cl)N2C=NC=N2)O
InChI InChI=1S/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+
InChI Key FBOUIAKEJMZPQG-AWNIVKPZSA-N

Properties

Appearance White to Off-white Solid
Application Pesticide
Antibiotic Activity Spectrum Fungi
Boiling Point 501.1±60.0°C at 760 mmHg
Melting Point 148-149°C
Density 1.27±0.1 g/cm3
Solubility Soluble in DMSO (Slightly), Methanol (Sparingly)

Toxicity

Carcinogenicity No indication of carcinogenicity to humans (not listed by IARC).

Reference Reading

1.Acid-base reaction-based dispersive liquid-liquid microextraction method for extraction of three classes of pesticides from fruit juice samples.
Farajzadeh MA1, Afshar Mogaddam MR2. J Chromatogr A. 2016 Jan 29;1431:8-16. doi: 10.1016/j.chroma.2015.12.059. Epub 2015 Dec 24.
A sample preparation method involving acid-base reaction-based dispersive liquid-liquid microextraction coupled with gas chromatography using nitrogen-phosphorous detection has been developed for the analysis of three classes of pesticides in juice samples. In this method, a basic organic solvent (p-chloroaniline) is used as an extraction solvent. It is dissolved in acidified deionized water and then injected into an alkaline aqueous sample solution. After injection, an acid-base reaction occurs and deprotonation of the organic solvent leads to formation of tiny droplets of the extractant and subsequent extraction of the analytes from sample solution. Under the optimum extraction conditions, the method showed low limits of detection and quantification in the range of 0.05-0.43ngmL(-1) and 0.17-1.43ngmL(-1), respectively. Extraction recoveries and enrichment factors were between 39.2 and 84.1% and between 548 and 1178, respectively. Relative standard deviations of less than 8.
2.A new Co(II) complex of diniconazole: synthesis, crystal structure and antifungal activity.
Xi T1, Li J1, Yan B1, Yang M2, Song J1, Ma H1. Acta Crystallogr C Struct Chem. 2015 Oct;71(Pt 10):889-93. doi: 10.1107/S2053229615016241. Epub 2015 Sep 18.
A new Co(II) complex of diniconazole, namely diaqua[(E)-(RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl-κN(4))pent-1-en-3-ol]cobalt(II) dinitrate dihydrate, [Co(C15H17Cl2N3O)3(H2O)2](NO3)2·2H2O, was synthesized and characterized by elemental analysis, IR spectroscopy and single-crystal X-ray diffraction. Crystal structural analysis shows that the centrosymmetric Co(II) cation is coordinated by four diniconazole ligands and two water molecules, forming a six-coordinated octahedral structure. There are also two free nitrate counter-anions and two additional solvent water molecules in the structure. Intermolecular O-H...O hydrogen bonds link the complex cations into a one-dimensional chain. In addition, the antifungal activity of the complex against Botryosphaeria ribis, Gibberella nicotiancola, Botryosphaeria berengriana and Alternariasolani was studied. The results indicate that the complex shows a higher antifungal activity for Botryosphaeria ribis and Botryosphaeria berengriana than diniconazole, but a lower antifungal activity for Gibberella nicotiancola and Alternariasolani.
3.Determination of triazole pesticide residues in edible oils using air-assisted liquid-liquid microextraction followed by gas chromatography with flame ionization detection.
Farajzadeh MA1, Feriduni B, Mogaddam MR. J Sep Sci. 2015 Mar;38(6):1002-9. doi: 10.1002/jssc.201400818. Epub 2015 Feb 5.
In the present study, a rapid, simple, and highly efficient sample preparation method based on air-assisted liquid-liquid microextraction followed by gas chromatography with flame ionization detection was developed for the extraction, preconcentration, and determination of five triazole pesticides (penconazole, hexaconazole, diniconazole, tebuconazole, and triticonazole) in edible oils. Initially, the oil samples were diluted with hexane and a few microliter of a less soluble organic solvent (extraction solvent) in hexane was added. To form fine and dispersed extraction solvent droplets, the mixture of oil sample solution and extraction solvent is repeatedly aspirated and dispersed with a syringe. Under the optimum extraction conditions, the method showed low limits of detection and quantification between 2.2-6.1 and 7.3-20 μg/L, respectively. Enrichment factors and extraction recoveries were in the ranges of 71-96 and 71-96%, respectively.
4.Dual-labeled time-resolved fluoroimmunoassay for simultaneous detection of clothianidin and diniconazole in agricultural samples.
Sheng E1, Shi H1, Zhou L1, Hua X1, Feng L1, Yu T1, Wang M2. Food Chem. 2016 Feb 1;192:525-30. doi: 10.1016/j.foodchem.2015.07.023. Epub 2015 Jul 8.
Europium (Eu(3+)) and samarium (Sm(3+)) were used as fluorescent labels to develop a highly sensitive dual-labeled time-resolved fluoroimmunoassay (TRFIA) for detect clothianidin and diniconazole in food samples. Under the optimized assay conditions, 50% inhibition concentration (IC50) and the limit of detection (LOD, IC10) of clothianidin were 5.08 and 0.021 μg/L, and 13.14 and 0.029 μg/L for diniconazole. The cross-reactivities (CRs) were negligible except dinotefuran (9.4%) and uniconazole (4.28%). The recoveries of clothianidin and diniconazole ranged from 79.3% to 108.7% in food samples. The results of TRFIA for the authentic samples were validated by gas chromatography (GC) analyses, and a satisfactory correlations were obtained. These results indicated that the method was an alternative tool for simultaneous detection of clothianidin and diniconazole in food samples.

Spectrum

Predicted LC-MS/MS Spectrum - 10V, Positive

Experimental Conditions

Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da

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