Iprodione

Product Name: Iprodione
CAS No.: 36734-19-7
Chemical Name: Iprodione
Synonyms: IPRODION;3-（3，5-dichlorophenyl)-1-iso-propylcarbamoylhydantion;3-(3,5-Dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-1-imidazolidinecarboxamide;KIDAN;ROVER;anfor;rovrol;ROVRAL;330.16;fa2071
CBNumber: CB7131064
Molecular Formula: C13H13Cl2N3O3
Formula Weight: 330.17
MOL File: 36734-19-7.mol

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Iprodione Property

Melting point:: 130-134 °C(lit.)
Density: 1.6223 (rough estimate)
vapor pressure: 5 x 10^-7 Pa (25 °C)
refractive index: 1.6140 (estimate)
Flash point:: 2 °C
storage temp.: Sealed in dry,Room Temperature
solubility: DMSO: 100 mg/mL (302.87 mM)
pka: 9.19±0.20(Predicted)
form: Solid
color: White to off-white
Water Solubility: 0.0013 g/100 mL
Merck: 13,5096
BRN: 895003
LogP: 3.000
CAS DataBase Reference: 36734-19-7(CAS DataBase Reference)
NIST Chemistry Reference: Iprodione(36734-19-7)
EPA Substance Registry System: Iprodione (36734-19-7)

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Safety

Hazard Codes: Xn,N,F
Risk Statements: 40-50/53-36-20/21/22-11
Safety Statements: 36/37-60-61-36-26-16
RIDADR: UN 3077 9/PG 3
WGK Germany: 3
RTECS: NI8870000
HS Code: 29332900
Hazardous Substances Data: 36734-19-7(Hazardous Substances Data)
Toxicity: LD50 in mice, rats (g/kg): 4, 3.5 orally (Lacroix, 1980)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H351Suspected of causing cancer

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P391Collect spillage. Hazardous to the aquatic environment

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 559792
Product name: [3-(3,5-Dichlorophenyl)-2,4-dioxoimidazolidinyl]-N-(methylethyl)carboxamide
Purity: 97%
Packaging: 25g
Price: $392
Updated: 2024/03/01

Sigma-Aldrich

Product number: 36132
Product name: Iprodione
Purity: PESTANAL
Packaging: 100mg
Price: $72.3
Updated: 2024/03/01

TRC

Product number: I745000
Product name: Iprodione
Packaging: 5g
Price: $165
Updated: 2021/12/16

TRC

Product number: I745000
Product name: Iprodione
Packaging: 500mg
Price: $65
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: CHM0014415
Product name: GLYCOPHENE
Purity: 95.00%
Packaging: 25MG
Price: $885.31
Updated: 2021/12/16

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Iprodione Chemical Properties,Usage,Production

Uses

Fungicide.

Uses

Iprodione is a non-systemic fungicide that exhibits both protectant and eradicant activities against the spores and mycelium of a number of parasitic fungi. It is effective against Alternaria, Botrytis, Corticium, Fusarium, Helminthosporium, Monilinia, Phoma, Pleiochaeta, Rhizoctonia and Sclerotinia, etc. in nut crops, fruit trees (stone and pome fruit), vines, berries, vegetables, cereals, oilseed rape, cotton and ornamentals. Iprodione also controls various summer and winter turf diseases.

Definition

ChEBI: An imidazolidine-2,4-dione in which the nitrogen at position 1 is substituted by an N-(isopropyl)carboxamide group while that at position 3 is substituted by a 3,5-dichlorophenyl group. A contact fungicide, it blocks the growth of the fu gal mycelium and inhibits the germination of fungal spores. It is used on fruit and vegetable crops affected by various fungal diseases. It is also used as a nematicide.

Production Methods

The synthesis uses 3,5-dichloroaniline which is coupled with glycine and phosgene. The urea substructure is formed by reaction with isopropylamine and phosgene. Many fungicide mixtures with Iprodione are on the market.

Safety Profile

Moderately toxic by ingestion. When heated to decomposition it emits very toxic fumes of NOx and Cl-.

Environmental Fate

Soil. Readily degrades in soil (half-life 20 to 160 days) releasing carbon dioxide 3,5dichloroaniline (Walker, 1987) and (Hartley and Kidd, 1987; Worthing and Hance, 1991). The rate of degradation increases with repeated applications of this fungicide. In a clay loam, the half-life was 1 week. After the second and third applications, the half-lives were 5 and 2 days, respectively (Walker et al., 1986).
Plant. Translocation and uptake by potato plants were reported (Cayley and Hide, 1980). Iprodione is rapidly metabolized in plants to 3,5-dichloroaniline (Cayley and Hide, 1980; Hartley and Kidd, 1987).
Chemical/Physical. In an aqueous solution at pH 8.7, iprodione hydrolyzed to N-(3,5dichloroanilinocarbonyl)-N-(isopropylaminocarbonyl)glycine (Belafdal et al., 1986). At pH 8.7, complete hydrolysis occurred after 14 hours (Cayley and Hide, 1980).
Gomez et al. (1982) studied the pyrolysis of iprodione in an helium atmosphere at 400–1,000°C. Decomposition began at 300°C producing isopropyl isocyanate and 3-(3,5dichlorophenyl)hydantoin. Above 600°C, the hydantoin ring began to decompose forming the following products: 3-chloroaniline, 3,5-dichloroaniline, chlorinated benzenes and benzonitrile. From 800 to 1,000°C, the hydantoin ring was completed destroyed whichled to the formation of aryl isocyanates, anilines and the corresponding diarylureas, namely 3-(3,5-dichlorophenyl)urea and 1-(3-chlorophenyl)-3-(3,5-dichlorophenyl)urea (Gomez et al., 1982).

Metabolic pathway

The opening and rearrangement of the dioxoimidazolidine ring is the initial and major degradation/metabolic reaction for iprodione. Iprodione degrades in soil via cleavage of the dioxoimidazolidine-carboxamide linkage, followed by ring opening to yield 3,5-dichloroaniline and CO2. In plants and animals, primary degradation reactions include N-dealkylation of the isopropyl moiety, ring opening and aryl hydroxylation (Scheme 1).

Degradation

Iprodione (1) is stable in acidic solution (< pH 5) and degraded rapidly in alkaline solution with DT₅₀ values of 37 days, 1.1 days and 21 min at pH 5, 7 and 9 at 25 °C, respectively (Melkebeke et al., 1986). Opening of the oxazolidinedione ring yielded N-(3,5-dichloroanilinocarbonyl)-N- (isopropylaminocarbonyl)glycine (2) (Belafdal et al., 1986). This reaction involves the attack of a hydroxyl ion on the carbonyl moiety in the 4-position of the hydantoin ring. Laurent (1974a, 1976a) and Das (1990) reported the further dehydration/rearrangement of compound 2 to yield an iprodione isomer (3).
Iprodione degraded readily in water under UV light irradiation (Laurent, 197413) but was relatively stable when exposed to simulated sunlight (Adrian and Robles, 1991). The degradation of iprodione in aqueous solution proceeded via various mechanisms including isomerisation, dechlorination, hydrolysis and hydroxylation.
Schwack et al. (1995) and Schwack and Bourgeois (1989) reported that dechlorination was the primary photodegradation reaction when iprodione in various organic solvents (e.g. isopropanol) was irradiated with UV light (>280 nm). Other photodegradation reactions included the replacement of the chlorine atom by the solvent molecule.

Iprodione Preparation Products And Raw materials

Raw materials

Isopropyl isocyanate HYDANTOIC ACID Glycine Triethylamine PHOSGENE 3,5-Dichlorophenyl isocyanate Diisopropyl ether Isopropylamine 3,5-Dichloroaniline

Preparation Products

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Iprodione Suppliers

Canada 2 China 230 France 2 Germany 3 India 3 Japan 2 South Korea 1 Switzerland 1 United Kingdom 5 United States 27 Global 276

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View Lastest Price from Iprodione manufacturers

HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD

Product: Iprodione 36734-19-7
Price: US $100.00-75.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 5000Ton
Release date: 2024-08-13

Hebei Dangtong Import and export Co LTD

Product: Iprodione 36734-19-7
Price: US $29410.00-39200.00/Tons
Min. Order: 1Tons
Purity: 99.99%
Supply Ability: 500Tons
Release date: 2023-03-28

qingdao trust agri chemical co.,ltd

Product: iprodione 36734-19-7
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99
Supply Ability: 20tons
Release date: 2024-07-24

36734-19-7, IprodioneRelated Search:

Hydantoin Dichloromethylphenylsilane Dichlorodiphenylsilane Sodium lauroylglutamate 3-(3,5-Dichlorophenyl)-1-methylhydantoin 1,3-Dimethyl-2-imidazolidinone 1-METHYLHYDANTOIN Biuret 1-METHYL-2-IMIDAZOLIDINONE 3-PHENYLIMIDAZOLIDINE-2,4-DIONE IPRODIONE METABOLITE,IPRODIONE METABOLITE STANDARD 1-(3,5-DICHLOROPHENYL)UREA (3,5-DICHLORO-PHENYL)-ETHYL-AMINE 1-PHENYL-IMIDAZOLIDIN-2-ONE N-(3,5-DICHLORO-PHENYL)-FORMAMIDE 3-CHLOROANILINE-2,4,6-D3 3-(3,5-dichlorophenyl)imidazolidine-2,4-dione N-ME-GLY-NME2

3-（3，5-dichlorophenyl)-1-iso-propylcarbamoylhydantion

3-（3，5-dichlorophenyl)-N-iso-propyl-2,4-dioxo-1-imidazoline carboxamide

[3-(3,5-Dichlorophenyl)-2,4-dioxoiMidazolidinyl]-N-(Methylethyl)carboxaMide standard solution

3-(3,5-Dichlorophenyl)-n-Isopropyl-2,4-dioxo-1-Imidazolidinecarboximide

Iprodione 100mg [36734-19-7]

[3-(3,5-Dichlorophenyl)-2,4-dioxoimidazolidinyl]-N-(methylethyl)carboxamide,Iprodione

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[3-(3,5-Dichlorophenyl)-2,5-dioxoiMidazolidinyl]-N-(Methylethyl)carboxaMide standard solution

IPRODIONE METABOLITE

IPRODION

IPRODIONE

GLYCOPHENE

CHIPCO 26019

KIDAN

LABOTEST-BB LT00134860

1-ISO-PROPYLCARBAMOYL-3-(3,5-DICHLOROPHENYL)HYDANTOIN

[3-(3,5-DICHLOROPHENYL)-2,4-DIOXOIMIDAZOLIDINYL]-N-(METHYLETHYL)CARBOXAMIDE

PROTURF

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VERISAN

’rovral’hn

1-Imidazolidinecarboxamide, 3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-

1-Imidazolidinecarboxamide,3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-

26019rp

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

3-(3,5-dichlorophenyl)-n-(1-methylethyl)-2,4-dioxo-1-imidazolidinecarboxamid

3-(3,5-dichlorophenyl)-n-(1-methylethyl)-2,4-dioxo-1-imidazolinecarboxamide

3-(3,5-Dichlorophenyl)-N-isopropyl-2,4-dioxo-1-imidazolidinecarboxamide

3-(3,5-dichlorophenyl)-n-isopropyl-2,4-dioxo-1-imidazolidinecarboximide(acn)

3-(3,5-dichlorophenyl)-n-isopropyl-2,4-dioxoimidazolidine-1-carboxamide

330.16

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c13-h13-cl2-n3-o3

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