General Description
Yellowish odorless liquid. Non corrosive. Used as a fungicide.
Reactivity Profile
A triazole derivative.
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.
First aid
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions) if
breathing has stopped, and CPR if heart action has stopped.
Transfer promptly to a medical facility. When this chemical
has been swallowed, get medical attention. Give large
quantities of water and induce vomiting. Do not make an
unconscious person vomit. Do not induce vomiting when
formulations containing petroleum solvents are ingested.
Evaluation by a qualified allergist, including exposure his-
tory and testing, may help diagnose allergy.
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.
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
Description
Propiconazole is a mixture of four stereoisomers and was first
developed in 1979 by Janssen Pharmaceutical of Belgium.
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.
Chemical Properties
normally provided as a yellow liquid
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.
Uses
Agricultural fungicide.
Uses
Labelled Propiconazole (P770100). Systemic foliar fungicide. Agricultural fungicide.
Uses
Propiconazole is a triazole-based fungicide that is used to
control fungi in agriculture, on turf, and in wood.
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.
Production Methods
Commercial production of cis-propiconazole mirrors the standard industrial synthesis of propiconazole but incorporates additional controls to enrich the cis isomer pair (2R,4S / 2S,4R). The core process begins with formation of the dioxolane intermediate from 2,4 dichloroacetophenone, followed by coupling with a 1,2,4 triazole derivative, steps well documented in propiconazole manufacturing literature. To obtain the cis enriched material, producers apply stereoselective crystallisation or controlled catalytic conditions during the dioxolane forming and triazole coupling stages, minimising formation of the trans isomers. Final purification removes unreacted intermediates and separates the desired cis isomer mixture, yielding technical grade cis propiconazole suitable for formulation.
Production Methods
Commercial production of trans-propiconazole mirrors the standard industrial synthesis of propiconazole but incorporates additional controls to enrich the trans isomer pair (2R,4S / 2S,4R). The core process begins with formation of the dioxolane intermediate from 2,4 dichloroacetophenone, followed by coupling with a 1,2,4 triazole derivative, steps well documented in propiconazole manufacturing literature. To obtain the trans enriched material, producers apply stereoselective crystallisation or controlled catalytic conditions during the dioxolane forming and triazole coupling stages, minimising formation of the cis isomers. Final purification removes unreacted intermediates and separates the desired trans isomer mixture, yielding technical grade trans propiconazole suitable for formulation.
Production Methods
The commercial production of propiconazole involves a multi-step chemical synthesis that typically begins with ethanone-1-(2,4-dichlorophenyl), which undergoes condensation with 1,2-pentanediol to form a dioxolane intermediate. This intermediate is then brominated in dichloromethane to produce a bromomethyl derivative, which finally undergoes nucleophilic substitution with a sodium triazole salt in dimethyl sulfoxide at elevated temperatures to yield propiconazole.
Flammability and Explosibility
Notclassified
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®
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.
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.
