Propiconazole

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.

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)