66246-88-6

Basic information

• Product Name: Penconazole
• Synonyms: 1-[2-(2,4-Dichlorophenyl)-n-pentyl]-1H-1,2,4-triazole;1-[2-(2,4-DICHLOROPHENYL)PENTYL]-1,2,4-TRIAZOLE;1-[2-(2,4-DICHLOROPHENYL)PENTYL]-1H-1,2,4-TRIAZOLE;PENCONAZOL;PENCONAZOLE;4-triazole,1-(2-(2,4-dichlorophenyl)pentyl)-1h-2;cga71818;onmex
• CAS NO: 66246-88-6
• Molecular Formula: C₁₃H₁₅Cl₂N₃
• Molecular Weight: 284.18
• EINECS: 266-275-6
• Product Categories: FUNGICIDE;Alpha sort;ConazolesPesticides&Metabolites;Fungicides;N-PAlphabetic;P;PA - PEN;Pesticides
• Mol File: 66246-88-6.mol

Chemical Properties

• Melting Point: 58.5 °C
• Boiling Point: 436.06°C (rough estimate)
• Flash Point: 100 °C
• Appearance: gray solid
• Density: 1.2556 (rough estimate)
• Vapor Pressure: 0.241mmHg at 25°C
• Refractive Index: 1.6300 (estimate)
• Storage Temp.: 0-6°C
• PKA: 2.80±0.10(Predicted)
• Water Solubility: 73 mg l-1 (25 °C)
• BRN: 541488
• CAS DataBase Reference: Penconazole(CAS DataBase Reference)
• NIST Chemistry Reference: Penconazole(66246-88-6)
• EPA Substance Registry System: Penconazole(66246-88-6)

Safety Data

• Safety Statements: 22-24/25
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 2
• RTECS: XZ4615000
• Hazardous Substances Data: 66246-88-6(Hazardous Substances Data)

Usage

Uses

Used in Agriculture:
Penconazole is used as a fungicide for the control of powdery mildew, pome fruit scab, and other pathogenic Ascomycetes, Basidiomycetes, and Deuteromycetes on various crops such as vines, cucurbits, pome fruit, stone fruit, ornamentals, hops, tobacco, and vegetables. This helps in protecting these plants from fungal infections and ensuring their healthy growth.

Trade name

AWARD?; CGA-71818?; ONMEX?; TOPAS?; TOPAS-C?; TOPAS-MZ?; TOPAZ?; TOPAZE?; TOPAZE-C?; TOPENCO 100EC?

Safety Profile

Moderately toxic by ingestion and skin contact. When heated to decomposition it emits toxic vapors of NOx and Clí.

Metabolic pathway

Penconazole is metabolised in plants by hydroxylation of the propyl side chain and conjugation or metabolism to triazolylalanine and triazolylacetic acid. It is quite persistent in soils but degradation by sunlight requires only a few days. It is eliminated rapidly from mammals.

Degradation

Penconazole (1) is stable to hydrolysis at pH 1-13 and at temperatures up to 350 °C. It is degraded in sunlight with a DT50 of 4 days in natural sunlight. Its photochemical reactions have been studied. On irradiation with light of wavelengths greater than 280 nm (high-pressure mercury lamp with filter), the major reaction was the formation of a cyclised product (2) (Scheme 1). Irradiation under the same conditions in isopropanol gave mainly 2 and 3 (a dechlorinated product). After 8 hours, yields were 29.8% of 2 and 12.3% of 3 respectively. The product 3 alone photodegraded only slowly but 2 was completely photolysed within 3 hours to further products, indicating its role as an intermediate in the photolytic pathways (Schwack and Hartmann, 1992, 1994). In the presence of isopropanol, photodehalogenation of 3 to 4 competed with substitution of a solvent molecule to give a low yield (

InChI:InChI=1/C5H11NO2/c1-5(2)6-8-4-3-7/h7H,3-4H2,1-2H3

Synthetic route

1-(1H-1,2,4-triazol-1-yl)-2-(2,4-dichlorophenyl)-1-penten → penconazole (66246-88-6)

Conditions	Yield
rhodium contaminated with carbon; platinumoxide; rhodiumoxide In tetrahydrofuran at 20℃; under 750.06 Torr; for 5.5h;	71.4%

1-[2-(2,4-dichlorophenyl)-pentyl]-1,2-diformylhydrazine → penconazole (66246-88-6)

Conditions	Yield
In formamide

penconazole (66246-88-6) → 2-[2-(2,4-dichlorophenyl)-pentyl]-2,4-dihydro-[1,2,4]triazole-3-thione (187670-56-0)

Conditions	Yield
Stage #1: penconazole With isopropylmagnesium chloride In tetrahydrofuran at 40℃; for 1.5h; Stage #2: With sulfur In tetrahydrofuran at 0℃; for 1h; Stage #3: With hydrogenchloride; water In tetrahydrofuran	60%

penconazole (66246-88-6) → C13H13Cl2N3O + C13H13Cl2N3O

Conditions	Yield
With oxygen; tetramethylammonium tetrafluoroborate; C5H13N2O(1+)*BF4(1-); sodium hydrogencarbonate In water; acetonitrile Reagent/catalyst; Electrochemical reaction;	A 19% B 7%

1-methyl-pyrrolidin-2-one (872-50-4) + hydrogen sulfide (7783-06-4) + penconazole (66246-88-6) → 2-(2,4-dichloro-phenyl)-1-(5-mercapto-1,2,4-triazol-1-yl)-pentane

hydrogen sulfide (7783-06-4) + penconazole (66246-88-6) → 2-(2,4-dichloro-phenyl)-1-(5-mercapto-1,2,4-triazol-1-yl)-pentane

Conditions	Yield
With 1-methyl-pyrrolidin-2-one
With 1-methyl-pyrrolidin-2-one
With 1-methyl-pyrrolidin-2-one
With 1-methyl-pyrrolidin-2-one

penconazole (66246-88-6) → (-)-penconazole + (+)-penconazole

Conditions	Yield
With chiralpak IC column In hexane; isopropyl alcohol at 20℃; Thermodynamic data; Solvent; Temperature; Resolution of racemate; enantioselective reaction;

Upstream product

• 89586-77-6 1-[2-(2,4-dichlorophenyl)-pentyl]-1,2-diformylhydrazine 

Downstream Products

• 187670-56-0 2-[2-(2,4-dichlorophenyl)-pentyl]-2,4-dihydro-[1,2,4]triazole-3-thione 

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Sorption of Penconazole (cas 66246-88-6) applied as a commercial water–oil emulsion in soils devoted to vineyards07/21/2019

The objective of this work was to assess the effect of surfactants and oils of a commercial formulation on the potential mobility of penconazole in agricultural soils that have been subjected to a high rate of application of agricultural chemicals. Soil–water partition tests on a commercial wat...detailed

Improving tolerance against drought in canola by Penconazole (cas 66246-88-6) and calcium07/19/2019

Drought stress is one of the most important environmental factors that limit plant growth. Canola is an important agricultural crop grown primarily for its edible oil. In this study, penconazole (PEN), a triazole growth regulator, and calcium (Ca2+), a secondary messenger, were used to analyses ...detailed

Effects of two different organic amendments addition to soil on sorption–desorption, leaching, bioavailability of Penconazole (cas 66246-88-6) and the growth of wheat (Triticum aestivum L.)07/18/2019

This study investigated the effects of sugarcane bagasse compost (SBC) and chicken manure compost (CMC) on the sorption–desorption, leaching and bioavailability of the fungicide penconazole in soil in a laboratory setting. The autoclave-treated SBC or CMC was applied at 2.5% and 5.0% (w/w). Res...detailed

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Long-term occupational and environmental exposure to Penconazole (cas 66246-88-6) and tebuconazole by hair biomonitoring07/15/2019

Penconazole (PEN) and tebuconazole (TEB) are fungicides widely used in vineyards. The aim of this the study was to assess the suitability of hair to assess long-term exposure to PEN and TEB.Hair samples of agricultural workers exposed to PEN (AW-PEN, 18 subjects) or TEB (AW-TEB, 2 subjects) duri...detailed

Assessment of Penconazole (cas 66246-88-6) exposure in winegrowers using urinary biomarkers07/14/2019

Penconazole (PEN) is a fungicide used in agriculture. The aim of this work was to evaluate the exposure to PEN in vineyard workers focusing on urinary biomarkers.Twenty-two agricultural workers were involved in the study; they were investigated during PEN applications and re-entry work, performe...detailed

Penconazole (cas 66246-88-6) alters redox status, cholinergic function and lung’s histoarchitecture of adult rats: Reversal effect of vitamin E07/13/2019

The present study pertains to the possible adverse effects of penconazole exposure on the lung of adult rats, and to the potential ability of vitamin E (Vit E) in mitigating the toxicity induced by this fungicide. Male Wistar rats were divided into four groups of six animals each: Group I (Contr...detailed

Application and enantioselective residue determination of chiral pesticide Penconazole (cas 66246-88-6) in grape, tea, aquatic vegetables and soil by ultra performance liquid chromatography-tandem mass spectrometry07/12/2019

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Developmental toxicity of Penconazole (cas 66246-88-6) in Zebrfish (Danio rerio) embryos07/11/2019

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