Iprodione

330.17

330.17

253-178-9

S3AYV2A6EU

DTXSID3024154

Colorless crystals|White crystals

2933290011

69.7

3.00

Cream to colorless, odorless powder.

1.5±0.1 g/cm3

136 °C (approx)

481.1±55.0 °C at 760 mmHg

2 °C

1.645

H2O: 0.0013 g/100 mL

APPROX 4°C

5 x 10 -7 Pa (25 °C)

Oral-Rat LD50: 72.8 mg/kg; Oral-Mouse LD50: 111 mg/kg

Combustion produces toxic nitrogen oxides and chloride gases

Odorless

3.12e-09 atm-m3/mole|Henry's Law constant = 3.12X10-9 atm-cu m/mole @ 25 °C

180 Ų [M+H]+

Non-hygroscopic

Non-corrosive to metals

UN 3077 9/PG 3

3

40-50/53-36-20/21/22-11

36/37-60-61-36-26-16

NI8870000

Xn,N,F

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Relatively stable to acid media, but decomposed in alkaline media.

P273-P281-P501

H351-H410

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.|Do not contaminate water, food, or feed by ... disposal of this chemical.

|Warning|H351: Suspected of causing cancer [Warning Carcinogenicity]|P201, P202, P273, P281, P308+P313, P391, P405, and P501|H320: Causes eye irritation [Warning Serious eye damage/eye irritation]|P201, P202, P260, P264, P270, P281, P305+P351+P338, P308+P313, P309+P311, P314, P337+P313, P405, and P501

Thirty-nine kinds of pesticides were monitored in Kitakyushu city, Japan using a high-volume air sampler(1). After sampling about 700 cu m of air during summer and spring months, iprodione was not detected at a detection limit of 0.2 ng/cu m.

The concentration of iprodione was studied in five different commercial compost samples(1). Iprodione was detected in two of the five samples; one at a concentration of 40.3 ug/kg and the other at 95.5 ug/kg.

highly

LD50 Rat oral 3500 mg/kg|LD50 Mouse oral 4000 mg/kg|LD50 Rat percutaneous >2500 mg/kg|LD50 Rabbit percutaneous >2000 mg/kg|For more Non-Human Toxicity Values (Complete) data for IPRODIONE (6 total), please visit the HSDB record page.

Iprodione's production and use as a fungicide(1,2) is expected to result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 700(2) indicates that iprodione is expected to have low mobility in soil(SRC). Volatilization of iprodione from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 3.12X10-9 atm-cu m/mole(3). Iprodione is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.75X10-9 mm Hg(4). Iprodione degraded with an observed half-life of 14 to 30 days in aerobic sandy loam soil that was incubated in the dark at 25 degrees C and 75% of 0.33 bar moisture for 276 days(5). The US Dept of Agric's Pesticide Properties Database lists a soil half-life of 14 days for iprodione(2) however, in acclimated soil, the half-life can be as low as 2 days(6); in non-acclimated soil, the half-life can be >35 days(6). Hydrolysis is probably important in moist alkaline soils; the aqueous hydrolysis half-lives of iprodione (at 25 °C) at respective pHs of 3, 5, 7, and 9 are 545.2, 37.4, 1.1, and 0.015 days(7).|TERRESTRIAL FATE: In laboratory studies using Woodstown loamy sand and Lodi loam soils, initial applications of iprodione (1.5-6 ug/g) were reduced to trace levels (<0.05 ug/g) within 8 to 48 weeks(1); the initial half-life in the Lodi loam soil at 21-28 °C, was approximately 1-2 weeks(1). In field plot studies, when iprodione was applied to previously untreated plots, about 3% of initial dose remained after 77 days(2); in plots treated once before, <1% remained after 18 days(2); in plots treated twice, <1% remained after 10 days(2). In additional studies, degradation of iprodione in soil was found to increase with increase in pH and with successive iprodione treatments(3); for example, times for 50% degradation following first, second and third applications were about 30, 12, and 4 days(3); time for 90% loss from previously untreated soils ranged from 22 to 93 days while soils treated once ranged from 16 to 28 days(3). 3,5-Dichloroaniline was identified as an important degradation product of iprodione in soil(4). In a New Zealand study, degradation rates of iprodione were found to increase with successive treatments(5); in untreated soils, 50% disappearance required >35 days while only 3.5 and 2 days were required for the 2nd and 3rd treatments(5).|TERRESTRIAL FATE: In a study conducted in San Juan Bautista, California, iprodione was applied eight times to carrots at one pound active ingredient/acre/application(1). Iprodione showed a half-life of seven days in the 0-15 cm soil layer of the silt loam soil with degradation products found in the soil up to 30 cm deep, but not below this. In a study conducted in North Carolina, using the same application rate, the observed half-life was less than three days in the 0-15 cm soil depth of a loamy sand soil. No degradation products or iprodione were detected below 15 cm. The soil pH's in the field studies varied from slightly acidic (pH 6.2-6.8) in North Carolina to slightly basic (pH 7.9-8.0) in California. Based on the studies, pH alone was not a good predictor of the relative rates of degradation of iprodione (< 4 days in NC, 7 days in CA). However, degradation products indicative of hydrolysis were detected suggesting that hydrolysis may be an important route of degradation in the field(1). In another study, an investigation of the leachability of pesticides applied to a golf course was conducted using lysimeters at actual golf courses(2). At a fairway consisting of Korean lawn grass grown over volcanic ash soil, iprodione was applied at 1.5 g/l/sq m. Leachate was collected 40 cm below the surface and analyzed over a 37 day period. At the end of 37 days, a total of 0.2% of the applied iprodione had leached through the fairway soil profile(2). Iprodione's degradation in a soil environment was also studied in five vineyard soils over a 77 day period (3). Iprodione was applied at 4 mg of active ingredient/kg of soil in an aqueous solution on three separate occasions for each soil. Overall, iprodione behaved similarly in each soil even though they each had different characteristics (e.g. texture ranged from sandy-loam to clay-loam). On the first application, it took 35 days to reach 90% degradation, while on the second application, it took 21 days to reach 90% degradation, and on the third application, it only took 7 days to reach 90% degradation(3). No residual pesticide levels were detected at 77 days. It appeared that the degradation rate for iprodione in soil was stimulated by previous treatments(3).|AQUATIC FATE: Based on a classification scheme(1), a Koc value of 700(2) indicates that iprodione is expected to slightly adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 3.12X10-9 atm-cu m/mole(4). According to a classification scheme(5), an estimated BCF of 41(SRC), from a log Kow of 3.00(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Aerobic aquatic metabolism is an important route of degradation for iprodione(8). It degraded with a half-life of 3 to 7 days in a flooded silt loam sediment system incubated in the dark. However, the water used in the experiment was at pH 8.5 suggesting that hydrolysis was a major contributor to iprodione degradation(8,9). The hydrolysis half-lives of iprodione (at 25 °C) at respective pHs of 3, 5, 7, and 9 are 545.2, 37.4, 1.1, and 0.015 days(9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), iprodione, which has a vapor pressure of the 3.75X10-9 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase iprodione may be removed from the air by wet and dry deposition(SRC).

Based upon a vapor pressure of 3.75X10-9 mm Hg(1), iprodione is expected to exist in the particulate phase in the atmosphere and therefore will not react with atmospheric hydroxyl radicals. Based upon experimental measurements at 60 °C and conversion to pseudo first-order rate constants at 25 °C, the aqueous hydrolysis half-lives of iprodione at respective pHs of 3, 5, 7, and 9 are 545.2, 37.4, 1.1, and 0.015 days(2). On irradiated soils, iprodione degraded with an observed degradation half-life of 7 to 14 days in sandy loam soil that was radiated with a xenon-arc lamp for 8.8 hours/day for 30 days(2). However, in the dark controls, radio labeled iprodione degraded with an observed half-life of 14 to 21 days. Therefore, degradation processes other than photolysis must have been responsible for the disappearance of iprodione in the irradiated system(2). Iprodione degraded slowly under aqueous photolysis conditions (estimated half-life of 67 days) in pH 5 buffered solutions irradiated continuously with a UV-filtered xenon-arc lamp(3). No major degradates were observed. Based upon soil experiments, photolysis on soil surfaces does not appear to be an important route of dissipation for iprodione(3).

338.84|An estimated BCF of 41 was calculated for iprodione(SRC), using a log Kow of 3.00(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration is moderate. Under basic conditions, the high rate of hydrolysis(4) for iprodione will decrease the potential for bioconcentration.

707.95 L/kg|The Koc for iprodione is 700(1). According to a classification scheme(2), this Koc value suggests that iprodione is expected to have low mobility in soil. In one study, an investigation of the leachability of pesticides applied to a golf course was conducted using lysimeters at actual golf courses(3). At a fairway consisting of Korean lawn grass grown over volcanic ash soil, iprodione was applied at 1.5 g/l/sq m. Leachate was collected 40 cm below the surface and analyzed over a 37 day period. At the end of 37 days, a total of 0.2% of the applied iprodione had leached through the fairway soil profile(3).

The Henry's Law constant for iprodione is 3.12X10-9 atm-cu m/mole(1). This Henry's Law constant indicates that iprodione is expected to be essentially nonvolatile from water surfaces(2). Iprodione is also not expected to volatilize substantially from soil due to aerobic soil metabolism, hydrolysis, and its low vapor pressure of 3.75X10-9 mm Hg(3,4). In addition, an aerobic soil metabolism study indicated that only 5.27% of the applied iprodione had volatilized after 276 days in a sandy loam soil. Of this, 5.23% was radio-labeled carbon dioxide(3).

GROUNDWATER: From April to October 1996, pesticide monitoring in 40 wells along the Oregon coastal region was conducted. Eighty-nine samples were collected, up to four samples at some wells, over the period of the study. All samples were reported as below the level of quantification; 0.1 ppb. No correlation with use areas was established, although samples were collected from areas with known grape production. In another study along the Central Snake River Basin in Oregon, 27 wells were sampled for a total of 30 samples. Iprodione was detected in all samples, but were reported as below the level of quantification (0.1 ppb). The study was conducted during a 3 day period in August 1996. A study conducted in the Lake Superior Western Basin in Wisconsin during July 1995 at 2 wells reported all samples as below the level of quantification of 0.55 ppb(1). Iprodione was monitored in 4 surface water features in the central coastal region of California near Santa Cruz in 1994. It is known that iprodione was applied in the watershed of the monitored sites. All four samples exceeded the minimum protection limits (0.1 ppb) on the day of sampling; the date of pesticide application was not ascertained prior to sampling. Concentrations ranged from 1.07 ppb at Hawkins Slough to 3.53 ppb in a drainage ditch from a nearby field. The mean concentration of the four samples was 2.7 ppb(1). The Pesticides in Ground Water Database (PGWDB) was created to provide a more complete picture of groundwater monitoring for pesticides in United States(2). It was a collection of ground-water monitoring studies conducted by federal, state and local governments, the pesticide industry and private institutions from 1971-1991. Of 15 groundwater studies which monitored for iprodione during this time period, it was never detected(2).|SURFACE WATER: Water samples were collected using solid-phase extraction at the mouth of the Shinano River in Niigata Prefecture, Japan from May to September 1996 and analyzed for iprodione (1). Iprodione was not detected (limit of detection = 0.02 ug/ml) in any of the samples.

Iprodione is one of many pesticides that has been detected in U.S. foods by the US Food and Drug Admin's regulatory monitoring of domestic foods for fiscal years 1983-1986(1) and 1978-1982(6); frequencies of occurrence and concns were not reported(1,6). In a US monitoring survey of 6970 produce samples (fruits and vegetables) collected between 1989 and 1991, iprodione was detected (detection limit of 2.0 ppm) in only two samples(2); the concn in the samples (one grape and one lettuce sample) was not reported(2). During a 5 yr study conducted during 1981-1986, the Los Angeles District Office of the FDA analyzed 19,851 samples of domestic and imported food for pesticide residues(3-4); iprodione was detected in 111 samples at concns ranging from 0.05 to >2.0 ppm(3-4); most detections were in the range from 0.5-2.0 ppm(3-4). In 1989 monitoring conducted by the California Dept of Food and Agric, iprodione was not detected (detection limit of 2.0 ppm) in 40 almond or 29 lettuce samples(5); however, it was detected in 2 peach and one prune samples(5).|During the 27 month period between January 1st 1992, and March 31st 1994, Agriculture and Agri-Food Canada analyzed 21,982 samples of fruit and vegetable commodities for pesticide residues. Iprodione was detected in cherries (0.5 ppm), grapes (0.1 ppm), nectarines (< 0.05 ppm), peaches (< 0.05 ppm), and raspberries (< 0.05 ppm)(1). Eight adult foods consumed in relatively large quantities by infants/children were selected from the domestic and import monitoring for 1985-1991 in the United States(2). These foods included apple juice, apples, bananas, grape juice, milk, orange juice, oranges, and pears. Of the 10,000 samples analyzed, only two imported foods, these being pears, had detectable quantities of iprodione at a maximum concentration of 0.22 ppm(2). From 1992-1993, the U.S. Food and Drug Administration(FDA) conducted a statistically based study of pesticide residues in domestic and imported pears and tomatoes(3). Iprodione was detected in one pear sample (concentration not reported). The concentration of various pesticides was determined on fruits, vegetables, and milk products in New York State(4). Iprodione detected in two peaches ranging from 0.003-0.006 ppm (total number of samples not indicated). In 1995, fruits and vegetable samples (397) were collected from eight local markets in Egypt and examined for 52 pesticides(5). Iprodione was detected three times in tomatoes maintain concentration from 0.05-0.22 ppm (0.11 ppm mean).

Occupational exposure to iprodione may occur through dermal contact and inhalation of sprays, especially to workers applying the compound as a pesticide(1). Since iprodione has been detected in U.S. foods(2), exposure to the general population may occur through consumption of foods containing iprodione residues(SRC). The general population may also be exposed to iprodione through fungicide use on fruit and vegetable gardens, ornamentals, turfgrass, professional use at residential sites, and other sites where non-occupational exposure may occur (e.g. golf courses, parks, and recreational areas)(3).|Several incidences of iprodione exposure have been reported to the EPA dating back as early as 1984. These incidences include: in 1994, when a UPS driver was exposed to iprodione after a bag spilled in his truck and he experienced dizziness; in 1995 when a male was sprayed with an aqueous use dilution mixture of iprodione after the rupture of a gauge; in 1994, when individuals alleged they developed skin rashes while working in their garden three days after iprodione and other pesticides were sprayed on crop fields; in 1996, when two workers prepared nonflowering ornamentals for shipment less than one day after foliar application of iprodione and another pesticide. The products were applied at 1 pound and 3 pounds/100 gallons of water. The workers wore rubber gloves to wrap loose vines around the main plants and developed a rash on their arms above the glove the next day. In California, a total of 26 individuals were reportedly exposed to iprodione from 1984 to 1995; 46 percent of those had skin illnesses(1).

Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc. (See all compounds classified as Fungicides, Industrial.)

Rapidly metabolized in plants to 3,5-dichloroaniline, following root uptake.

Inhibits germination of spores and growth of fungal mycelium.

No human poisonings have been reported.

1-isopropylcarbamoyl-3-(3,5-dichlorophenyl)hydantoin

Use of iprodione (pounds per year) for the following crops: almonds (75,000 to 205,000); grapes (80,000 to 125,000); peaches (50,000 to 65,000); potatoes (55,000 to 215,000); rice (65,000 to 145,000).

USEPA/OPP Pesticide Code 109801; Trade Names: Iprodine; Glycophene; Chipco 26019; Anfor; RP-26019; Rovral.|Wettable powder; suspension concentrate; hot fogging concentrate; dustable powder; ULV liquid|Mixed formulations: (iprodione +) carbendazim; fenpropimorph|Flowable|Technical grade active ingredient: 95%; Liquid soluble concentrate (14 and 41.6 percent active ingredient); wettable powder (33.3 and 50 percent active ingredient); Dry flowable (50 percent active ingredient); Flowable concentrates (41.6 percent active ingredient); Emulsifiable concentrate (19.65, 23.3, and 50 percent active ingredient); Granular (1.02 and 1.3 percent active ingredient).

Compatible with most other pesticides.

Analysis of products and residues by using GLC with ECD and by HPLC with UV detection.|FDA Method 242.1. Organonitrogen Residues General Method for Nonfatty Foods Including Acetone Extraction and Isolation in Organic Phase. Detection limit not specified.

Agrochemicals -> Fungicides, Nematicides|Fungicides|Environmental transformation -> Pesticides (parent, predecessor)

Iprodione has known environmental transformation products that include 1-(3,5-dichlorophenyl)-5-isopropyl biuret, 3,5-dichloroaniline, 3-(3,5-dichlorophenyl)-2,4-dioxoimidazolidine, and N-(3,5-dichlorophenylcarbamoyl)-N-isopropylcarbamoyl-glycine.|Iprodione has known environmental transformation products that include 3-(3,5-dichlorophenyl)-2,4-dioxoimidazolidine, LS720942, N-(3,5-dichlorophenylcarbamoyl)-N-isopropylcarbamoyl-glycine, RP 25040, RP 30181, RP 30228, RP 32596, RP 35606, RP 36221, RP 36233, and RP 37176.