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Pesticides

Pesticide -> EPA IRIS

Fungicides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Fungicides

Fungicides

Yellowish, viscous liquid

White crystalline powder

Colorless solid

47 g/L in n-hexane; completely miscible with ethanol, acetone, toluene, and octanol.

Soluble in most organic solvents

In water, 100 mg/L at 25 °C

0.000001 [mmHg]

1X10-6 mm Hg at 25 °C

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

Yellowish liquid; [Merck Index] Colorless or white solid or yellowish liquid; [HSDB] Yellowish liquid (clear if purified); mp = -23 deg C; [eChemPortal: ESIS] Clear yellow viscous liquid; [MSDSonline]

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P318, P321, P330, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P318, P321, P330, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Chemical: 1H-1,2,4-Triazole, 1-[[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl]methyl]-

Hazard Traits - Reproductive Toxicity

Regulation (EC) No 396/2005 (amended)

Propiconazole is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

03/70/EC, Reg. (EU) 2016/2016, Reg. (EU) 2018/1865, Reg. (EU) No 540/2011, Reg. (EU) No 823/2012, Reg.(EU) 2018/84

Status: Active Update: 16-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/32104

Caused skin sensitization in guinea pigs; In high-dose feeding studies, causes liver injury and developmental toxicity; A possible human carcinogen; [EPA REDs] May cause skin sensitization; May cause liver injury, based on animal studies; [eChemPortal: ESIS] A skin and eye irritant; May cause skin sensitization; [MSDSonline]

Tolerances are established for the combined residues of the fungicide 1-[[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl] methyl]-1H-1,2,4-triazole and its metabolites determined as 2,4-dichlorobenzoic acid and expressed as parent compound in or on the following commodities: [Table#6224]

Time-limited tolerances are established permitting the combined residues of 1-[[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole and its metabolites determined as 2,4-dichlorobenzoic acid and expressed as parent compound, in connection with use of the pesticide under section 18 emergency exemptions granted by EPA. Residues in these commodities not in excess of the established tolerances resulting from the uses described in this paragraph remaining after expiration of the time-limited tolerances will not be considered to be actionable if the pesticide is applied during the term of and in accordance with the provisions of this paragraph. The tolerances are specified in the following table. These tolerances expire on the date specified in the table. [Table#6225]

A tolerance with regional registration, as defined in part 180.1(n), is established for residues of 1-[[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole and its metabolites determined as 2,4-dichlorobenzoic acid and expressed as parent compound, in or on the following commodities: [Table#6226]

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Propiconazole is found on List C. Case No: 3125; Pesticide type: fungicide; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): propiconazole ; Data Call-in (DCI) Date(s): 09/30/93, 10/13/95; AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner. OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the RED document.

Acute Tox. 4 (100%)

Reproductive toxicity - category 1B

Acute toxicity (Oral) - Category 4

Acute toxicity (Oral) - Category 4

Repr. 1B

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Tolerances are established for the combined residues of the fungicide 1-[[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl] methyl]-1H-1,2,4-triazole and its metabolites determined as 2,4-dichlorobenzoic acid and expressed as parent compound in or on the following commodities: [Table#6221]

Time-limited tolerances are established permitting the combined residues of 1-[[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole and its metabolites determined as 2,4-dichlorobenzoic acid and expressed as parent compound, in connection with use of the pesticide under section 18 emergency exemptions granted by EPA. Residues in these commodities not in excess of the established tolerances resulting from the uses described in this paragraph remaining after expiration of the time-limited tolerances will not be considered to be actionable if the pesticide is applied during the term of and in accordance with the provisions of this paragraph. The tolerances are specified in the following table. These tolerances expire on the date specified in the table. [Table#6222]

A tolerance with regional registration, as defined in part 180.1(n), is established for residues of 1-[[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole and its metabolites determined as 2,4-dichlorobenzoic acid and expressed as parent compound, in or on the following commodities: [Table#6223]

Propiconazole can cause corneal opacity that is reversible with 72 hours. In animal chronic toxicity tests, the benign and malignant liver tumors were found in rats and mice. Propiconazole is categorized as a possible human carcinogen. Propiconazole is also a developmental toxin that caused skeletal deformations in newborn pups.

LD50 Anas platyrhynchos (Mallard duck; age 5 days) oral >1000 mg/kg[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on 1-[

LD50 Anas platyrhynchos (Mallard duck; age 6 months) oral 2510 mg/kg[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on 1-[

LC50 Anas platyrhynchos (Mallard duck) diet >5620 ppm/8 days[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on 1-[

LD50 Apis mellifera (Honey bee, adult) topical >25 ug/bee[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on 1-[

For more Ecotoxicity Values (Complete) data for PROPICONAZOLE (25 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), measured Koc values ranging from 1,200-8,100(2), indicates that propiconazole is expected to have slight to no mobility in soil(SRC). Volatilization of propiconazole from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.1X10-10 atm-cu cm/mole derived from its vapor pressure, 4.2X10-7 mm Hg(3), and water solubility 100 mg/L(3). Propiconazole is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. Propiconazole is expected to biodegrade in the environment(4-8). Based on monitoring data, field and laboratory tests, propiconazole has an estimated half-life of about 60-96 days in typical soils(4,8).

AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 1,200-1,800(2), indicates that propiconazole is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 9.1X10-10 atm-cu m/mole(SRC) derived from its vapor pressure, 4.2X10-7 mm Hg(4), and water solubility, 100 mg/L(4). According to a classification scheme(5), an estimated BCF of 146(SRC), from log Kow of 3.72(4) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Propiconazole has been reported to be stable to hydrolysis(7). Propiconazole is expected to biodegrade in the environment and has and estimated half life of 25-85 days in aerobic water(4).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), propiconazole, which has a vapor pressure of 4.2X10-7 mm Hg at 25 °C(2), will exist solely in particulate phase in the ambient atmosphere. Particulate-phase propiconazole may be removed from the air by wet and dry deposition(SRC). Propiconazole does not absorb at wavelengths >290 nm(2) and has been shown to be resistant to direct photolysis from sunlight(3).

Propiconazole was detected in celery with a mean concentration of 0.034 ppm(1). Propiconazole was detected in wine with a mean concentration of 0.0009 ppm(1). Propiconazole was detected in must (0.01 mg/L), white wine (0.01 mg/L) and red wine 0.70 mg/L(2). Propiconazole was found in 1/13 apple samples from an Egyptian market with a concentration of 0.39 mg/kg(3).

Propiconazole can decrease cholesterol levels that may cause polyploidy and disruption of mitotic cell cycling. It down-regulates the PTEN pathway and up-regulates the WNT-beta-catenin signaling pathway, that would stimulate cell proliferation and may lead to the tumorigenic outcome. (A15329)

/AQUATIC SPECIES/ The fungicide propiconazole (1-(2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl) -1H-1,2,4-triazole) induced the hepatic cytochrome P4501A (CYP1A) activity towards ethoxyresorufin-O-deethylase (EROD), the content of CYP1A protein as quantified by enzyme-linked immunosorbent assay (ELISA) and the glutathione S-transferase (GST) activity towards the three commonly used substrates CDNB(1-chloro-2,4-dinitrobenzene), cumene hydroperoxide (CU) and ethachrynic acid (EA) in brown trout (Salmo trutta) depending on dose and body weight. An exponential dose response relationship existed between propiconazole exposure and CYP1A activity. A 2. order polynomial regression of the propiconazole concentration (square root transformed) on the data for CDNB, EU and CU revealed a bell-shaped pattern of the GST induction. Reverse-phase HPLC of the GSH-affinity chromatography purified GST isozymes in trout exposed to respectively 8.3, 23, 93, 313 and 606 microg l(-1) propiconazole in the water indicated that the propiconazole treatment may lead to changes in the composition of the subunits compared to the controls. Thus, propiconazole exposure through the water changed the properties of the brown trout hepatic CYP1A and GST, and these changes may be used as a bioindicator on the molecular level of exposure and effect of propiconazole in controlled experiments. The use in monitoring of propiconazole exposure under natural field conditions is possible, however needs further investigation.

Propiconazole was detected in the effluent of an agricultural site in Sweden at a maximum concentration of 2 ug/L(1). Propiconazole was found in the runoff water of 4 out of 5 Costa Rican Banana plantations in concentrations ranging from 24.2-6.1 ug/L(2).

Propiconazole

Gastrointestinal

1.3 x 10 ^-2 mg/kg-day

Tolerances are established for the combined residues of the fungicide 1-[[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl] methyl]-1H-1,2,4-triazole and its metabolites determined as 2,4-dichlorobenzoic acid and expressed as parent compound in or on the following commodities: [Table#6224]

Time-limited tolerances are established permitting the combined residues of 1-[[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole and its metabolites determined as 2,4-dichlorobenzoic acid and expressed as parent compound, in connection with use of the pesticide under section 18 emergency exemptions granted by EPA. Residues in these commodities not in excess of the established tolerances resulting from the uses described in this paragraph remaining after expiration of the time-limited tolerances will not be considered to be actionable if the pesticide is applied during the term of and in accordance with the provisions of this paragraph. The tolerances are specified in the following table. These tolerances expire on the date specified in the table. [Table#6225]

A tolerance with regional registration, as defined in part 180.1(n), is established for residues of 1-[[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole and its metabolites determined as 2,4-dichlorobenzoic acid and expressed as parent compound, in or on the following commodities: [Table#6226]

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Propiconazole is found on List C. Case No: 3125; Pesticide type: fungicide; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): propiconazole ; Data Call-in (DCI) Date(s): 09/30/93, 10/13/95; AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner. OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the RED document.

A first version cDNA microarray of the cladoceran Daphnia magna /was developed/. Through Suppression Subtractive Hybridization PCR (SSH-PCR) 855 life stage-specific cDNAs were collected and used to document the toxicological mode of action of the pesticide propiconazole. DNA sequencing analysis revealed gene fragments related to important functional classes such as embryo development, energy metabolism, molting and cell cycle. Major changes in transcription were observed in organisms exposed for 4 and 8 days to 1 microg/mL. After 4 days a 3-fold down-regulation of the gene encoding the yolk protein, vitellogenin, was observed indicating impaired oocyte maturation. Moreover, genes such as a larval-specific gene and chaperonin were repressed, whereas the heat shock 90 protein and ATP synthase were induced. Organismal effects clearly confirmed the major molecular findings: at the highest concentration (1 ug/mL) adult growth was significantly (p < 0.05) impaired and increased developmental effects in the offspring could be noted. We have demonstrated the potential of microarray analysis in toxicity screening with D. magna. The use of vitellogenin mRNA as a rapid biomarker of reproductive effects in chronic toxicity studies with cladocerans is suggested.

The metabolism of orally administered (14C)-phenyl propiconazole was studied in mice pretreated with unlabeled propiconazole followed by a single oral dose of (14C)-phenyl propiconazole at a corresponding dose level. The urinary metabolite pattern of propiconazole demonstrated a marked sex dependency. In male mice, 60% of the radioactivity in 0-24 hour urine was represented by one metabolite, this metabolite accounted for 30% in the 0-24 hour urine in female mice. This metabolite was identified by spectroscopy as the glucuronic acid conjugate of 1-(2,4-dichlorophenyl)-2-(1 H-1,2,4-triazol-1-yl) ethanol. This demonstrates that the major metabolic pathway in mice involves dioxolane ring cleavage.

The metabolism of propiconazole was investigated in male rats administered a single oral dose of 31.4 mg/kg triazole-(3,5-14C-propiconazole). Metabolites were isolated from first day urine and feces excretion representing 44.5% and 36.2% of the applied dose, respectively. A wide array of biotransformations occurred leading to numerous metabolites. The major site of enzymatic attack oxidation of the propyl side chain leading via alcohols and diols to carboxy acids and alpha-hydroxy carboxy acid or cleavage of the dioxolane ring. The majority of the alcoholic and phenolic metabolites are renally excreted as sulfuric acid and glucuronic acid conjugates. In the rat the main metabolite is the alpha hydroxyl carboxylic acid of propiconazole.

/In rats/...the major sites of enzymic attack are the propyl side-chain and the cleavage of the dioxolane ring, together with some attack at the 2,4-dichlorophenyl and 1,2,4-triazole rings. In mice, the major metabolic pathway is via cleavage of the dioxolane ring.

After oral administration to rats, propiconazole is rapidly absorbed and also rapidly and almost completely eliminated with urine and feces. Residues in tissues were generally low and there was no evidence for accumulation or retention of propiconazole or its metabolites.

Male and female mice were fed a diet containing 5, 100 and 2500 ppm propiconazole for 21 days, followed by a single oral dose of (14C)-phenyl propiconazole at a mean corresponding dose level (0.8/1.0, 16.8/21.5 and 434/475 mg/kg bw for males/females). Urinary excretion accounted for 45-81% of the administered dose after 96 hours and tended to be higher by males than by females. In the feces 22-43% was excreted. At the lowest dose level (5 ppm propiconazole) the residual radioactivity in blood, liver, kidneys, lungs and in the remaining carcass was below 0.02 mg/kg propiconazole equivalents and accordingly higher at the 100 and 2500 ppm dose level. Residues in female mice were higher than in male mice, except in the kidneys where the males showed higher or equal values. Independent of the dose level and sex of the animals, the highest residues were found in the liver, up to 2.3 and 3.0 mg/kg in males and females of the highest dose level, respectively.

Orally administered single doses (0.5 and 25 mg/kg bw) of triazole labelled (3,5-14C)-propiconazole to rats were rapidly excreted within 24 hours (74-84%). After 6 days, 0.04-0.15%, 28-46% and 53-67% had been recovered from expired air, feces and urine respectively. Only about 0.4% of the administered dose remained in the tissues. Highest tissue residues were found in liver, blood and kidneys. No unchanged propiconazole was excreted in the urine. Within 3 days after treatment of male rats with a single oral dose of about 32 mg/kg bw of triazole labelled (3,5-14C)-propiconazole or a phenyl-(U-14C) labelled propiconazole, more than 95% of the dose was excreted. Of this, 52% was found in the urine and 43-48% in the feces. The excretion pattern for both compounds was identical with no administered compound being found in the urine.

Single doses of triazole-14C-propiconazole (1.0 and 10.0 mg/kg bw) applied dermally to rats were absorbed through the skin following first order kinetics with half-lives averaging 24-31 hours for low and high dosed rats, respectively. Equal amounts of the dose were excreted within 72 hours in urine and feces. The amount of residual radioactivity on the skin averaged 20% of the applied dose.

Feed consumption, milk production or the general health of a lactating goat were not affected after the daily oral administration of 5 mg triazole-14C-propiconazole for 10 consecutive days (which would correspond to 4.5 ppm in the feed). Of the total dose, 89% was excreted within 24 hours after the last administration (68% and 21% in urine and feces, respectively). All tissues contained less than 0.02 mg/kg propiconazole equivalents, except liver (0.096 mg/kg) and kidney (0.029 mg/kg). The total radioactivity secreted with the milk reached a plateau at day three of 0.013-0.016 mg/kg, representing 0.18% of the total dose.

Used as systemic foliar fungicide to protect cereals, bananas, turf, rice, coffee, peanuts, stone fruit, and maize; as wood preservative; as seed treatment for use on bananas, barley, corn, peanuts, pecans, rice, rye, oats, soybeans, stone fruit, sugar beets, triticale, wheat, grasses grown for seed, turf, and ornamentals; [HSDB]

Applying Wood Preservatives [Category: Other]

For Propiconazole (USEPA/OPP Pesticide Code: 122101) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Systemic foliar fungicide with a broad range of activity. ...On cereals, it controls diseases caused by Cochliobolus sativus, Erysiphe graminis, Leptosphaeria nodorum, Puccinia spp., Pyrenophora teres, Pyrenophora tritici-repentis, Rhynchosporium secalis and Septoria spp. In bananas, control of Mycosphaerella musicola and Mycosphaerella fijiensis var. difformis. Other uses are in turf against Sclerotinia homoeocarpa, Rhizoctonia solani, Puccinia spp. and Erysiphe graminis; in rice against Rhizoctonia solani, Helminthosporium oryzae and dirty panicle complex; in coffee against Hemileia vastatrix; in peanuts against Cercospora spp.; in stone fruit against Monilinia spp., Podosphaera spp., Sphaerotheca spp. and Tranzschelia spp.; in maize against Helminthosporium spp.

... Wood preservative ... effective against wood-destroying basidiomycetes, and also against soft rot and blue stain fungi.

Agricultural antifungal

G. Van Reet et al., German patent 2,551,560; US 4,079,062 (1976, 1978 both to Janssen).

Ketalization of 2-bromo-2',4'-dichloroacetophenone with 1,2-pentanediol, followed by nucleophilic subsitution with sodium 1,2,4-triazolide in dimethylformamide at 160 °C.

Formulation types: emulsifiable concentrate; emulsifiable get; suspension (flowable) concentrate.

Trade name: Tilt (Novartis); Radar (Zeneca).

Wettable powder

Fungicides

Environmental transformation -> Pesticides (parent, predecessor)