Propiconazole

Description

Propiconazole is a mixture of four stereoisomers and was first developed in 1979 by Janssen Pharmaceutical of Belgium.

Chemical properties

normally provided as a yellow liquid

Chemical properties

Colorless solid or a yellow thick liquid. Odorless. Commercial product is available as an emulsifi- able concentrate. Physical and toxicological properties may be affected by carrier solvents in commercial formulations.

The Uses of Propiconazole

Labelled Propiconazole (P770100). Systemic foliar fungicide. Agricultural fungicide.

The Uses of Propiconazole

Agricultural fungicide.

The Uses of Propiconazole

Propiconazole is a triazole-based fungicide that is used to control fungi in agriculture, on turf, and in wood.

What are the applications of Application

Propiconazole is a systemic foliar and agricultural fungicide

Definition

ChEBI: Propiconazole is the cyclic ketal obtained by formal condensation of 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone with pentane-1,2-diol. A triazole fungicide, it is used commercially as a diastereoisomeric mixture on soft fruit (including apricots, peaches, nectarines, plums and prunes), nuts (including peanuts, pecans and almonds), mushrooms, and grasses grown for seeds. It has a role as a xenobiotic, an environmental contaminant, an EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor and an antifungal agrochemical. It is a member of triazoles, a cyclic ketal, a dichlorobenzene, a conazole fungicide and a triazole fungicide.

General Description

Yellowish odorless liquid. Non corrosive. Used as a fungicide.

Reactivity Profile

A triazole derivative.

Flammability and Explosibility

Not classified

Agricultural Uses

Fungicide: Used to control fungi on a broad range of crops and turf. Used on ornamentals, range land and rights-of-way to prevent and control powdery mildew and fungi on hardwoods and conifers.

Trade name

ALAMO®; BANNER®; BENIT®; BREAK®; BUMPER®; CGA-64250®; CGA-92710 F®; DESMEL®; FIDIS®; JUNO®; MANTI® S; MAXX®; NOVEL®; ORBIT®; PRACTIS®; PROPIMAX®; RADAR®; RESTORE®; SPIRE®; STRATEGO® (trifloxystrobin + propiconazole); TASPA®; TILT®; WOCOSIN®

Potential Exposure

Propiconazole is a triazole fungicide used to control fungi on a broad range of crops and turf. Used on ornamentals, range land and rights-of-way to pre- vent and control powdery mildew and fungi on hardwoods and conifers.

Environmental Fate

Routes and Pathways, and Relevant Physicochemical Properties Log Kow＝3.72
Solubilities: 47 g l1 in n-hexane; completely miscible with ethanol, acetone, toluene, and octanol; soluble in most organic solvents; in water ＝ 100 mg l^-1 at 25°C
Henry's law constant＝ 4.1×10^-9 atm-cu mmol^-1 at 25°C
Partition Behavior in Water, Sediment, and Soil Terrestrial Fate
Propiconazole penetrates the terrestrial environment in its function as a fungicide for a variety of crops. In the terrestrial environment, propiconazole is presented to be slightly persistent to persistent. Biotransformation is an important route of transformation for propiconazole, with major transformation products being 1,2,4-triazole and compounds hydroxylated at the dioxolane moiety. Phototransformation on soil or in air is not important for propiconazole transformation. Propiconazole appears to have medium to low mobility in soil. It has the potential to reach ground water through leaching, especially in soils with low organic matter content. Propiconazole is typically detected in the upper soil layers, but transformation products were detected deeper in the soil profile.
Environmental Persistency
Propiconazole is persistent and relatively immobile in most soil and aqueous environments. Propiconazole degradation in the aquatic environment appears to be dependent solely on aqueous photolysis. In the soil, propiconazole dissipation appears to be dependent on binding to soil organic matter content. The average half-life in soils ranges from months to a year.
Propiconazole is expected to biodegrade in the environment. The estimated half-life of propiconazole in aerobic soils is about 40–70 days, and in aerobic waters is about 25–85 days. Based on monitoring data and field tests, propiconazole has an estimated half-life of about 60–96 days in typical soils. No hydrolysis of propiconazole at environmentally relevant pH has been observed.
Propiconazole degrades into triazole compounds, which may still be toxic. Decomposition of propiconazole by heating may release toxic gases.

Metabolic pathway

The numerous metabolites of propiconazole are identified from rat urine and feces. Major sites for enzymatic attack are the propyl side chain and the cleavage of the dioxane ring. The 2,4-dichlorophenyl ring is attacked in various ways including the formation of a cyclohexadiene ring system, hydroxylation, replacement of the chlorine substituent by a hydroxy group, and introduction of a methylthio group. The 1,2,4-triazole ring is oxidatively attacked, leading to hydroxy derivatives. The vast majority of the alcoholic and phenolic metabolites are excreted as sulfuric acid and glucuronic acid conjugates. The major metabolic pathway in mice is via cleavage of the dioxane ring. Photolysis causes cleavage of the C1-triazole bond of propiconazole, liberating 1,2,4-triazole as the major product. Six more degradation products are identified which are not included in the mammalian metabolites.

Shipping

UN3082 Environmentally hazardous substances, liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required. UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.

Degradation

Photolysis of propiconazole (1) in hexane and methanolic solutions irradiated with a high-pressure mercury lamp gave a mixture of products 2-8 (Scheme 1) (Dureja et al., 1987). The major product isolated was 1,2,4- triazole (7). A monodechlorinated product (5) was formed in hexane. The dioxolane ring was cleaved in methanol under these conditions.
Sunlight irradiation on a sandy loam soil surface for 48 days degraded 80% of the applied material and a DTs0 of about 12 days on soil was derived through further rate studies. 1,2,4-Triazole (7) was the major product identified after exposing a thin layer of propiconazole, coated as a thin film, inside a Pyrex flask to sunlight for one month.

Toxicity evaluation

Propiconazole mode of action is demethylation of C-14 during ergosterol biosynthesis and leading to accumulation of C-14 methyl sterols. The biosynthesis of these ergosterols is critical to the formation of cell walls of fungi. This lack of normal sterol production slows or stops the growth of the fungus, effectively preventing further infection and/or invasion of host tissues. Therefore, propiconazole is considered to be fungistatic or growth inhibiting rather than fungicidal or killing.

Incompatibilities

The triazoles are sensitive to heat, friction, and impact. Sensitivity varies with the type substitution to the triazole ring. Metal chelated and halogen substitution of the triazol ring make for a particularly heat sensitive material. Azido and nitro derivatives have been employed as high explosives. No matter the derivative these materials should be treated as explosives

Waste Disposal

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Contact a licensed disposal facility about surplus and nonrecyclable solutions. Burn in a chemical incinerator equipped with an afterburner and scrubber. Extra care must be exercised as the material in an organic solvent is highly flammable. In accordance with 40CFR165, follow recom- mendations for the disposal of pesticides and pesticide con- tainers. Containers must be disposed of properly by following package label directions or by contacting your local or federal environmental control agency, or by con- tacting your regional EPA office. Incineration or permanga- nate oxidation.