基本信息
- 标准SMILES
CC(C)NC(=O)N1CC(=O)N(c2cc(Cl)cc(Cl)c2)C1=O- InChIKey
ONUFESLQCSAYKA-UHFFFAOYSA-N- 分子式
- C13H13Cl2N3O3
- 平均分子量
- 330.16 g/mol
- 单同位素质量
- 329.0333967
名称与标识
- 首选名称
- Iprodione
- IUPAC
- 3-(3,5-dichlorophenyl)-2,4-dioxo-N-propan-2-ylimidazolidine-1-carboxamide
- 中文名
- 异菌脲
- 英文名
- Iprodione
- 分子式
- C13H13Cl2N3O3
- 分子量
- 330.17
名称与别名
展开更多名称
数据库标识
- CAS
36734-19-7- PubChem CID
- 37517
- DTXSID
DTXSID3024154- ChEMBL
CHEMBL1862887- ChEBI
CHEBI:28909- UNII
- S3AYV2A6EU
- EC Number
- 253-178-9
- Nikkaji
- J3.500I
性质
结构计算性质
- XLogP
- 3.1
- 极性表面积
- 69.7 Ų
- 氢键供体
- 1
- 氢键受体
- 3
- 可旋转键
- 2
- 重原子
- 21
- 形式电荷
- 0
- 复杂度
- 448
实验与物化性质
LogP
log Kow = 3.00
3.00
Color/Form
Colorless crystals
White crystals
Solubility
Solubility at 20 °C (g/l): ethanol 25; methanol 25; acetone 300; dichloromethane 500; dimethylformamide 500
Solubility (20 °C): 300 g/l acetophenone, anisole; 500 g/l 1-methyl-2-pyrrolidone
Solubility: acetonitrile 150, toluene 150, benzene 200 (all in g/l at 20 °C)
In water, 13.9 mg/l @ 25 °C.
0.0139 mg/mL at 25 °C
Decomposition
DT50 1-7 days (pH 7), <1 hr (pH 9). Aqueous solns degraded by uv light.
When heated to decomposition it emits very toxic fumes of /nitrogen oxides & hydrogen chloride/.
Melting Point
approx 136 °C
136 °C
Physical Description
Colorless odorless solid; [Merck Index] White powder; [MSDSonline]
Solid
物理化学性质
- 熔点
- 130 · 130-134 °C(lit.)
- 密度
- 1.6223 · 1.6223 (rough estimate)
- 蒸气压
- 5 x · 5 x 10-7 Pa (25 °C)
- 折射率
- 1.614 · 1.6140 (estimate)
- 闪点
- 2 °C · 2 °C
- 储存条件
- Sealed in dry,Room Temperature
- 溶解度
- 100 mg/mL · DMSO: 100 mg/mL (302.87 mM)
- 酸度系数(pKa)
- 9.19 · 9.19±0.20(Predicted)
- 形态
- Solid
- 颜色
- White to off-white
- 水溶解性
- 0.0013 g/100 · 0.0013 g/100 mL
- Merck
- 13 · 13,5096
- BRN
- 895003 · 895003
- Henry's Law Constant
- 7.1 · 7.1×102 mol/(m3Pa) at 25℃, Barcelo and Hennion (1997)
- 主要应用
- agriculturecleaning productscosmeticsenvironmentalfood and beveragespersonal care
- InChI
- 1S/C13H13Cl2N3O3/c1-7(2)16-12(20)17-6-11(19)18(13(17)21)10-4-8(14)3-9(15)5-10/h3-5,7H,6H2,1-2H3,(H,16,20)
- InChIKey
- ONUFESLQCSAYKA-UHFFFAOYSA-N
- SMILES
- CC(C)NC(=O)N1CC(=O)N(C1=O)c2cc(Cl)cc(Cl)c2
- LogP
- 3 · 3.000
- CAS 数据库
- 36734 · 36734-19-7(CAS DataBase Reference)
- NIST化学物质信息
- Iprodione(36734-19-7)
- EPA化学物质信息
- Iprodione (36734-19-7)
化学性质
纯品为无色结晶。m.p.约136℃,蒸气压2.7×10-5Pa (20℃),在甲醇、乙醇中的溶解度为25g/L,丙酮、苯乙酮、苯甲醚中为300g/L,二氯甲烷、二甲基甲酰胺、1-甲基吡咯烷-2-酮中为500g/L,在水中溶解度为13mg/L(20℃)。不易烯,一般条件下贮存稳定,碱性条件不稳定,无腐蚀性。工业品m.p.126~130℃。
安全与法规
GHS分类
GHS Classification
Warning
H351: Suspected of causing cancer [Warning Carcinogenicity];H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]
P203, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)
Danger
危害信息
Regulatory Information
Hazard Traits - Carcinogenicity;Authoritative List - Prop 65;Report - regardless of intended function of ingredient in the product
Commission Regulation No 844/2012
Iprodione is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)
03/31/EC, Reg. (EU) 2016/950, Reg. (EU) 2017/1511, Reg. (EU) 2017/2091, Reg. (EU) No 540/2011, Reg. (EU) No 823/2012
Iprodione: Does not have an individual approval but may be used under an appropriate group standard
Other Safety Information
IMAP assessments - 1-Imidazolidinecarboxamide, 3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-: Environment tier I assessment;IMAP assessments - 1-Imidazolidinecarboxamide, 3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-: Human health tier I assessment
FIFRA Requirements
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. Iprodione is found on List B. Case No: 2335; 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): 3-(3-5-Dichlorophenyl-N-(1-methylethyl)-2,4-dioxo- 1-imidazolidinecarboxamide; Data Call-in (DCI) Date(s): 09/23/91, 03/03/95, 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.
Tolerances are established for the combined residues of the fungicide iprodione [3-(3,5-dichlorophenyl)- N-(1-methylethyl)-2,4-dioxo-1-imidazolidinecarboxamide], its isomer 3-(1-methylethyl)-N-(3,5-dichlorophenyl)-2,4-dioxo-1-imidazolidinecarboxamide, and its metabolite 3-(3,5-dichlorophenyl)-2,4-dioxo-1-imidazolidine-carboxamide in or on the following raw agricultural commodities: almonds (hulls); almonds (nutmeat); apricots; beans (dried, vine hay); beans (dry); beans (forage); beans (succulent); blueberries; boysenberries; broccoli; caneberries; carrots; cherries, sour; cherries, sweet, (pre and post-H); cottonseed; currants; garlic; ginseng; ginsend, dried; grapes; kiwi fruit; lettuce; nectarines (pre- and post-H); onions (dry bulb); peaches (pre- and post-H); peanuts; peanut forage; peanut hay; plums (pre- and post-H); potatoes; prunes; raisins; rasberries; rice bran; rice grain; rice hulls; rice straw; and strawberries.
Tolerances are established for the combined residues of the fungicide iprodione [3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-1-imidazolidinecarboxamide], its isomer 3-(1-methylethyl)-N-(3,5-dichlorophenyl)-2,4-dioxo-1-imidazolidinecarboxamide, and its metabolite 3-(3,5-dichlorophenyl)-2,4-dioxo-1-imidazolidine-carboxamide and [N-(3,5-dichloro-4-hydroxyphenyl)-ureido-carboxamide], all expressed as iprodione equivalents in or on the following raw agricultural commodities of animal origin: cattle, fat;; cattle, kidney; cattle, liver; cattle, meat;; cattle, mbyp (except kidney and liver);; eggs; goats, fat;; goats, kidney; goats, liver; goats, meat;; goat, mbyp (except kidney and liver);; hogs, fat;; hogs, kidney; hogs, liver; hogs, meat;; hogs, mbyp (except kidney and liver);; horses, fat;; horses, kidney; horses, liver; horses, meat;; horses, mbyp (except kidney and liver);; milk;; poultry, fat; poultry, liver; poultry, meat; poultry, mbyp (except liver); sheep, fat;; sheep, kidney; sheep, liver; sheep, meat;; sheep mbyp (except kidney and liver).
Tolerances with regional registration, as defined in 180.1(n), are established for the combined residues of the fungicide iprodione [3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-1-imidazolidinecarboxamide], its isomer 3-(1-methylethyl)-N-(3,5-dichlorophenyl)-2,4-dioxo-1-imidazolidinecarboxamide, and its metabolite 3-(3,5-dichlorophenyl)- 2,4-dioxo-1-imidazolidinecarboxamide in or on the following raw agricultural commodity: Chinese mustard.
Hazard Classes and Categories
Acute Tox. 3 (15.3%);Carc. 2 (100%);Aquatic Acute 1 (100%);Aquatic Chronic 1 (100%)
Carcinogenicity - category 2;Hazardous to the aquatic environment (acute) - category 1;Hazardous to the aquatic environment (chronic) - category 1
Serious eye damage/eye irritation - Category 2B;Carcinogenicity - Category 2;Reproductive toxicity - Category 2;Specific target organ toxicity - Single exposure - Category 2 (nervous system);Specific target organ toxicity - Repeated exposure - Category 2 (hematopoietic system);Hazardous to the aquatic environment (Acute) - Category 1;Hazardous to the aquatic environment (Long-term) - Category 1
Carc. 2;Aquatic Acute 1;Aquatic Chronic 1
安全与防护
Disposal Methods
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.
Allowable Tolerances
Tolerances are established for the combined residues of the fungicide iprodione [3-(3,5-dichlorophenyl)- N-(1-methylethyl)-2,4-dioxo-1-imidazolidinecarboxamide], its isomer 3-(1-methylethyl)-N-(3,5-dichlorophenyl)-2,4-dioxo-1-imidazolidinecarboxamide, and its metabolite 3-(3,5-dichlorophenyl)-2,4-dioxo-1-imidazolidine-carboxamide in or on the following raw agricultural commodities: almonds (hulls), 2.0 ppm; almonds (nutmeat), 0.3 ppm; apricots, 20.0 ppm; beans (dried, vine hay), 90.0 ppm; beans (dry), 2.0 ppm; beans (forage), 90.0 ppm; beans (succulent), 2.0 ppm; blueberries, 15.0 ppm; boysenberries, 15.0 ppm; broccoli, 25.0 pm; caneberries, 25.0 ppm; carrots, 5.0 ppm; cherries, sour, 20.0 ppm; cherries, sweet, (pre and post-H), 20.0 ppm; cottonseed, 0.10 ppm; currants, 15.0 ppm; garlic, 0.1 ppm; ginseng, 2.0 ppm; ginsend, dried, 4.0 ppm; grapes, 60.0 ppm; kiwi fruit, 10.0 ppm; lettuce, 25.0 ppm; nectarines (pre- and post-H), 20.0 ppm; onions (dry bulb), 0.5 ppm; peaches (pre- and post-H), 20.0 ppm; peanuts, 0.5 ppm; peanut forage, 150.0 ppm; peanut hay, 150.0 ppm; plums (pre- and post-H), 20.0 ppm; potatoes, 0.5 ppm; prunes, 20.0 ppm; raisins, 300.0 ppm; rasberries, 15.0 ppm; rice bran, 30.0 ppm; rice grain, 10.0 ppm; rice hulls, 50.0 ppm; rice straw, 20.0 ppm; and strawberries, 15.0 ppm.
Tolerances are established for the combined residues of the fungicide iprodione [3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-1-imidazolidinecarboxamide], its isomer 3-(1-methylethyl)-N-(3,5-dichlorophenyl)-2,4-dioxo-1-imidazolidinecarboxamide, and its metabolite 3-(3,5-dichlorophenyl)-2,4-dioxo-1-imidazolidine-carboxamide and [N-(3,5-dichloro-4-hydroxyphenyl)-ureido-carboxamide], all expressed as iprodione equivalents in or on the following raw agricultural commodities of animal origin: cattle, fat, 0.5 ppm; cattle, kidney, 3.0 ppm; cattle, liver, 3.0 ppm; cattle, meat, 0.5 ppm; cattle, mbyp (except kidney and liver), 0.5 ppm; eggs, 1.5 ppm; goats, fat, 0.5 ppm; goats, kidney, 3.0 ppm; goats, liver, 3.0 ppm; goats, meat, 0.5 ppm; goat, mbyp (except kidney and liver), 0.5 ppm; hogs, fat, 0.5 ppm; hogs, kidney, 3.0 ppm; hogs, liver, 3.0 ppm; hogs, meat, 0.5 ppm; hogs, mbyp (except kidney and liver), 0.5 ppm; horses, fat, 0.5 ppm; horses, kidney, 3.0 ppm; horses, liver, 3.0 ppm; horses, meat, 0.5 ppm; horses, mbyp (except kidney and liver), 0.5 ppm; milk, 0.5 ppm; poultry, fat, 3.5 ppm; poultry, liver, 5.0 ppm; poultry, meat, 1.0 ppm; poultry, mbyp (except liver), 1.0 ppm; sheep, fat, 0.5 ppm; sheep, kidney, 3.0 ppm; sheep, liver, 3.0 ppm; sheep, meat, 0.5 ppm; sheep mbyp (except kidney and liver), 0.5 ppm.
Tolerances with regional registration, as defined in 180.1(n), are established for the combined residues of the fungicide iprodione [3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-1-imidazolidinecarboxamide], its isomer 3-(1-methylethyl)-N-(3,5-dichlorophenyl)-2,4-dioxo-1-imidazolidinecarboxamide, and its metabolite 3-(3,5-dichlorophenyl)- 2,4-dioxo-1-imidazolidinecarboxamide in or on the following raw agricultural commodity: Chinese mustard, 15.0 ppm.
毒理信息
Ecotoxicity Values
LD50 Colinus virginianus (Bobwhite quail) oral >2000 mg/kg
LD50 Anas platyrhynchos (Mallard) oral 10,400 mg/kg
LC50 Rainbow trout 4.1 mg/l/96 hr /Conditions of bioassay not specified/
LC50 Bluegill sunfish 3.7 mg/l/96 hr /Conditions of bioassay not specified/
Environmental Fate
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% degrada
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).
Food Survey Values
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).
Average Daily Intake
Based upon results of the FDA's pesticide residue monitoring program for fiscal year 1988, the avg daily intake of iprodione for various age groups were as follows(1): 6-11 month old: 0.0017 ug/kg body wt/day; 14-16 yr-old males: 0.0013ug/kg body wt/day; 60-65 yr old females: 0.0014 ug/kg body wt/day(1). In September of 1998, the EPA estimated that the exposure of iprodione through the consumption of red meat was 0.002668 ug/kg/day, for poultry was 0.001999 ug/kg/day, and for total dairy was 0.004552 ug/kg/day(2). The estimated exposure for the consumption of grapes, wine and sherry, was 0.0000114 ug/kg/day(2). From June 1984 to April 1986, a U.S. National Total Diet Study was performed that determined the average daily intake of iprodione for infants aged 6-11 months and 2 years was 0.1 and 2.6 ng/kg body weight/day, respectively(3). For males aged 14-16, 25-30 and 60-65 yrs of age the average daily intake was 2.1, 1.8, and 1.3 ng/kg body weight/day, respectively, while for women aged 14-16, 25-30, and 60-65 yrs of age, the average daily intake was 0.4,0.4, and 0.3 ng/kg body weight/day, respectively(3). From July 1986 to April 1991, a U.S. National Total Diet Study was performed that determined the average daily intake of iprodione for infants aged 6-11 months and 2 years was 2.7 and 3.3 ng/kg body weight/day, respectively(4). For males aged 14-16, 25-30 and 60-65 yrs of age the average daily intake was 1.1, 0.9, and 1.4 ng/kg body weight/day, respectively, while for women aged 14-16, 25-30, and 60-65 yrs of age, the average daily intake was 0.7, 1.4, and 1.7 ng/kg body weight/day, respectively(4).
EPA IRIS Information
Iprodione
Hematologic;Reproductive
4 x 10 ^-2 mg/kg-day
Soil Adsorption/Mobility
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).
Atmospheric Concentrations
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.
Environmental Biodegradation
In 28-day incubation studies using a vegetable-growing clay loam soil, degradation of iprodione was >50% in non-sterile and <20% in sterile (autoclaved) soil(1); the results suggest that microbes were responsible for the primary disappearance in the soil(1). Similar results were found in another study in which degradation was much slower in soils treated with sodium azide, gamma irradiation, chloramphenicol or cycloheximide as compared to non-sterile soil(2).
AEROBIC: 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. Aerobic aquatic metabolism is also an important route of degradation for iprodione. It degraded with a half-life of 3 to 7 days in a flooded silt loam sediment system incubated in the dark. It could be expected that degradation in soils with pH's at or above 7 would be more rapid than in acidic soils due to chemical hydrolysis. The study of iprodione degradation in the sandy loam soil was conducted in slightly acidic to neutral conditions (pH 5.75-6.92) and it appears reasonable to conclude that the degradation was primarily due to metabolism and not chemical hydrolysis. In the aquatic study using flooded silt loam sediment, however, the sediment was at pH 6.64 and the water at 8.5 suggesting that hydrolysis could have played a major role in the decomposition of iprodione(1).
ANAEROBIC: Iprodione degraded with an observed half-life of 7-14 days in anaerobic silt loam sediment(1). As discussed in the abiotic section, iprodione undergoes chemical hydrolysis. As such, it could be expected that degradation in sediments with pH's at or above 7 would be more rapid than in acidic environments due to this additional route of degradation. In the anaerobic study, the sediment was at pH 6.4 and the water at 7.4 suggesting that hydrolysis could have played a major role in the decomposition of iprodione(1).
法规信息
Regulatory Information
Hazard Traits - Carcinogenicity;Authoritative List - Prop 65;Report - regardless of intended function of ingredient in the product
Commission Regulation No 844/2012
Iprodione is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)
03/31/EC, Reg. (EU) 2016/950, Reg. (EU) 2017/1511, Reg. (EU) 2017/2091, Reg. (EU) No 540/2011, Reg. (EU) No 823/2012
Iprodione: Does not have an individual approval but may be used under an appropriate group standard
FIFRA Requirements
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. Iprodione is found on List B. Case No: 2335; 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): 3-(3-5-Dichlorophenyl-N-(1-methylethyl)-2,4-dioxo- 1-imidazolidinecarboxamide; Data Call-in (DCI) Date(s): 09/23/91, 03/03/95, 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.
Tolerances are established for the combined residues of the fungicide iprodione [3-(3,5-dichlorophenyl)- N-(1-methylethyl)-2,4-dioxo-1-imidazolidinecarboxamide], its isomer 3-(1-methylethyl)-N-(3,5-dichlorophenyl)-2,4-dioxo-1-imidazolidinecarboxamide, and its metabolite 3-(3,5-dichlorophenyl)-2,4-dioxo-1-imidazolidine-carboxamide in or on the following raw agricultural commodities: almonds (hulls); almonds (nutmeat); apricots; beans (dried, vine hay); beans (dry); beans (forage); beans (succulent); blueberries; boysenberries; broccoli; caneberries; carrots; cherries, sour; cherries, sweet, (pre and post-H); cottonseed; currants; garlic; ginseng; ginsend, dried; grapes; kiwi fruit; lettuce; nectarines (pre- and post-H); onions (dry bulb); peaches (pre- and post-H); peanuts; peanut forage; peanut hay; plums (pre- and post-H); potatoes; prunes; raisins; rasberries; rice bran; rice grain; rice hulls; rice straw; and strawberries.
Tolerances are established for the combined residues of the fungicide iprodione [3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-1-imidazolidinecarboxamide], its isomer 3-(1-methylethyl)-N-(3,5-dichlorophenyl)-2,4-dioxo-1-imidazolidinecarboxamide, and its metabolite 3-(3,5-dichlorophenyl)-2,4-dioxo-1-imidazolidine-carboxamide and [N-(3,5-dichloro-4-hydroxyphenyl)-ureido-carboxamide], all expressed as iprodione equivalents in or on the following raw agricultural commodities of animal origin: cattle, fat;; cattle, kidney; cattle, liver; cattle, meat;; cattle, mbyp (except kidney and liver);; eggs; goats, fat;; goats, kidney; goats, liver; goats, meat;; goat, mbyp (except kidney and liver);; hogs, fat;; hogs, kidney; hogs, liver; hogs, meat;; hogs, mbyp (except kidney and liver);; horses, fat;; horses, kidney; horses, liver; horses, meat;; horses, mbyp (except kidney and liver);; milk;; poultry, fat; poultry, liver; poultry, meat; poultry, mbyp (except liver); sheep, fat;; sheep, kidney; sheep, liver; sheep, meat;; sheep mbyp (except kidney and liver).
Tolerances with regional registration, as defined in 180.1(n), are established for the combined residues of the fungicide iprodione [3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-1-imidazolidinecarboxamide], its isomer 3-(1-methylethyl)-N-(3,5-dichlorophenyl)-2,4-dioxo-1-imidazolidinecarboxamide, and its metabolite 3-(3,5-dichlorophenyl)- 2,4-dioxo-1-imidazolidinecarboxamide in or on the following raw agricultural commodity: Chinese mustard.
安全数据
- wgk
- 3
- 毒性
- LD50 in mice, rats (g/kg): 4, 3.5 orally (Lacroix, 1980)
- RTECS号
- NI8870000
- 存储类别
- 11 - Combustible Solids
- 安全说明
- 36/37-60-61-36-26-16
- 海关编码
- 29332900
- 危险品标志
- Xn,N,F
- 危险性类别
- Aquatic Acute 1Aquatic Chronic 1Carc. 2
- 危险类别码
- 40-50/53-36-20/21/22-11
- 毒害物质数据
- 36734-19-7(Hazardous Substances Data)
- 危险品运输编号
- UN 3077 9/PG 3
毒性防护
毒性雄性大鼠急性经口LD502060mg/kg,雌性为1530mg/kg。雄性小鼠急性经口LD50为1870mg/kg,雌性为2670mg/kg。也有报道大鼠急性经口LD503500mg/kg,小白鼠为4000mg/kg。兔急性经皮LD50>10000mg/kg。大、小鼠吸入LD50>130mg/L。对眼睛和皮肤无刺激作用。用含1000mg/kg、2400mg/kg药剂的饲料分别饲喂大鼠18个月和狗3个月,未见中毒症状。动物试验未见致畸、致癌、致突变作用。虹鳟鱼LC50为6.7mg/L (96h),鲤鱼LC50为10mg/,蓝鳃鱼LC50为2.25~6.30mg/L。水蚤LC50为3.6mg/L,野鸭经口LD50>10400mg/kg,鹌鹑LD50930mg/kg。蜜蜂LD50>400g/只。
急性毒性口服- 大鼠 LD50: 72.8 毫克/公斤; 口服- 小鼠 LD50: 111 毫克/ 公斤
包装储运
可燃性危险特性燃烧产生有毒氮氧化物和氯化物气体
储运特性库房通风低温干燥; 与食品原料分开储运
灭火剂干粉、泡沫、砂土
化学与工业
药理信息
用途与制造
Uses
Used as a fungicide; as a post-harvest dip; as a seed treatment; as a dip or spray at planting; [HSDB]
Farming (Pesticides) [Category: Industry]
For Iprodione (USEPA/OPP Pesticide Code: 109801) 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./
Can also be used as a post-harvest dip, as a seed treatment, or as a dip or spray at planting.
Fungicide
This is a man-made compound that is used as a pesticide.
Formulations/Preparations
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).
Use Classification
Environmental transformation -> Pesticides (parent, predecessor)
Fungicides
应用领域
用途广谱性触杀型杀菌剂。对孢子、菌丝体、菌核同时起作用,抑制病菌孢子萌发和菌丝生长。在植物体内几乎不能渗透,属保护性杀菌剂。本药剂对灰葡萄孢属、核盘属、链孢霉属、小菌核属、丛梗孢属具有较好的杀菌作用。防治番茄早疫病在番茄移植后约10d开始喷药,用50%可湿性粉剂11.3~22.5g/100m2,每隔2周喷药1次,共3~4次;防治灰霉病在病害发生前开始用药,用50%可湿性粉剂5g/100m2,隔10~14d喷药1次(花期、结果期尤佳),共3~4次,能提高番茄产量和品质。如每百千克种子用100~200g原药进行种子处理,对由禾蠕孢和小麦网腥黑粉菌引起的黑穗病有防效。用50%可湿性粉剂配成4g/L浓度药液浸马铃薯种薯,对由立枯丝菌引起的黑痣病有防效。葱蒜球根处理可防治黑腐菌核病。用50%可湿性粉性11.3~15g/100m2,在油菜初花期和盛花期各喷1次药,可防治油菜菌核病。应用本药剂宜与其他药剂交替使用或混用,以免产生耐药性。
用途异菌脲为接触型杀菌剂,对孢子、菌丝体同时起作用,对灰葡萄孢属、从梗孢属、核盘菌属、小菌核菌属、交链孢属等所引起的病害,均有防治效果。异菌脲也可用作种子处理。
用途属广谱保护性杀菌剂
制备方法
生产方法将0.019mol异丙基异氰酸酯和0.054mol三乙胺的混合物,加至0.045mol 3-(3,5-二氯苯基)乙内酰胺和150mol丙酮溶液中,加热回流。冷却,减压蒸除丙酮,所得残留物用石油醚(沸点50-70℃)250mol洗涤,经重结晶而得异菌脲。
生产方法甘氨酸(NH2CH2COOH)或酯与3,5-二氯异氰酸苯酯反应,生成3-(3,5-二氯苯基)酰脲乙酸(或酯),接着环化,得3-(3,5-二氯苯基)乙内酰脲,熔点190℃,待用。将4.6g(0.019mol)异丙基异氰酸酯和5.5g(0.054mol)三乙胺的混合物,添加到11g(0.045mol) 3-(3,5-二氯苯基)乙内酰脲、150mL丙酮溶液中。加热回流30min后冷却,减压脱溶,残留物用石油醚(沸点50~70℃,250mL)洗净,经异丙醚重结晶,得11g异菌脲,收率74.2%,熔点136℃。
上下游产品信息
上游原料
试剂价格
- HY-B1978R · 10 mg
- 异菌脲Iprodione (Standard) — 300元
- HY-B1978R · 50 mg
- 异菌脲Iprodione (Standard) — 600元
供应商50 家
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