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Iprodione structure
Iprodione structure

Iprodione

Iupac Name:3-(3,5-dichlorophenyl)-2,4-dioxo-N-propan-2-ylimidazolidine-1-carboxamide
CAS No.: 36734-19-7
Molecular Weight:330.16662
Modify Date.: 2023-02-13 23:41
Introduction: 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 fugal 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. View more+
1. Names and Identifiers
1.1 Name
Iprodione
1.2 Synonyms

[3-(3,5-Dichlorophenyl)-2,4-dioxoimidazolidinyl]-N-(methylethyl)carboxamide [3-(3,5-Dichlorophenyl)-2,4-dioxoiMidazolidinyl]-N-(Methylethyl)carboxaMide standard solution [3-(3,5-Dichlorophenyl)-2,4-dioxoimidazolidinyl]-N-(methylethyl)carboxamide,Iprodione [3-(3,5-Dichlorophenyl)-2,5-dioxoimidazolidinyl]-N-(methylethyl)carboxamide 1-Imidazolidinecarboxamide, 3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo- 1-Imidazolidinecarboximidic acid, 3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo- 26019 rp 3-(3,5-dichlorophenyl)-1-iso-propylcarbamoylhydantion 3-(3,5-dichlorophenyl)-2,4-dioxo-N-(propan-2-yl)imidazolidine-1-carboxamide 3-(3,5-dichlorophenyl)-2,4-dioxo-N-propan-2-ylimidazolidine-1-carboxamide 3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-1-imidazolidinecarboxamide 3-(3,5-Dichlorophenyl)-N-isopropyl-2,4-dioxo-1-imidazolidinecarboxamide 3-(3,5-Dichlorophenyl)-n-Isopropyl-2,4-dioxo-1-Imidazolidinecarboximide 3-(3,5-Dichlorophenyl)-N-isopropyl-2,4-dioxo-1-imidazolidinecarboximidic acid 3-(3,5-dichlorophenyl)-N-iso-propyl-2,4-dioxo-1-imidazoline carboxamide 3-(3,5-DICHLOROPHENYL)-N-ISOPROPYL-2,4-DIOXOIMIDAZOLIDINE-1-CARBOXAMIDE 3-(3,5-Dichlorphenyl)-N-isopropyl-2,4-dioxoimidazolidin-1-carboxamid 5-24-05-00201 5-24-05-00201 (Beilstein Handbook Reference) anfor EINECS 253-178-9 fa2071 Glycophen Glycophene Iprodione 100mg [36734-19-7] Iprodione ([3-(3,5-Dichlorophenyl)-2,4-dioxoimidazolidinyl]-N-(methylethyl)carboxamide KIDAN MFCD00055353 mrc910 N-[1-(3,5-Dichlorophenyl)-2,5-dioxo-4-imidazolidinyl]-2-methylpropanamide nrc910 Propanamide, N-[1-(3,5-dichlorophenyl)-2,5-dioxo-4-imidazolidinyl]-2-methyl- rop500f Roval dust ROVER ROVRAL rovrol

1.3 CAS No.
36734-19-7
1.4 CID
37517
1.5 EINECS(EC#)
253-178-9
1.6 Molecular Formula
C13H13Cl2N3O3 (isomer)
1.7 Inchi
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)
1.8 InChkey
ONUFESLQCSAYKA-UHFFFAOYSA-N
1.9 Canonical Smiles
CC(C)NC(=O)N1CC(=O)N(C1=O)C2=CC(=CC(=C2)Cl)Cl
1.10 Isomers Smiles
CC(C)NC(=O)N1CC(=O)N(C1=O)C2=CC(=CC(=C2)Cl)Cl
2. Properties
2.1 Density
1.464
2.1 Melting point
130-136℃
2.1 Boiling point
481.1±55.0 °C at 760 mmHg
2.1 Refractive index
1.575
2.1 Flash Point
2 °C
2.1 Precise Quality
329.03300
2.1 PSA
69.72000
2.1 logP
3.27380
2.1 Solubility
0.0013 g/100 mL
2.2 Appearance
Cream to colorless, odorless powder.
2.3 Color/Form
Colorless crystals
White crystals
2.4 Corrosivity
Non-corrosive to metals
2.5 Decomposition
DT50 1-7 days (pH 7), <1 hr (pH 9). Aqueous solns degraded by uv light.
2.6 HenrysLawConstant
3.12e-09 atm-m3/mole
2.7 Odor
Odorless
2.8 pKa
9.19±0.20(Predicted)
2.9 Water Solubility
0.0013 g/100 mL
2.10 Stability
Stable at normal temperatures and pressures.
2.11 StorageTemp
Sealed in dry,Room Temperature
3. Use and Manufacturing
3.1 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 fugal 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.
3.2 Usage
Fungicide.
4. Safety and Handling
4.1 Symbol
GHS08, GHS09
4.1 Hazard Codes
Xn
4.1 Signal Word
Warning
4.1 Risk Statements
R40;R50/53
4.1 Safety Statements
S36/37;S60;S61
4.1 Octanol/Water Partition Coefficient
log Kow = 3.00
4.2 Hazard Declaration
H351-H410
4.2 DisposalMethods
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.
4.3 RIDADR
UN 3077
4.3 Safety Profile
Moderately toxic by ingestion. When heated to decomposition it emits very toxic fumes of NOx and Cl-.
4.4 Caution Statement
P273-P281-P501
4.4 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).
4.5 WGK Germany
3
4.5 RTECS
NI8870000
4.5 Safety

Safety Information of Iprodione(36734-19-7):
Hazard Codes:Xn ,N ,F
Risk Statements:40-50/53-36-20/21/22-11?
R40:Limited evidence of a carcinogenic effect.?
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.?
R36:Irritating to eyes.?
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.?
R11:Highly flammable.
Safety Statements:36/37-60-61-36-26-16?
S36/37:Wear suitable protective clothing and gloves.?
S60:This material and its container must be disposed of as hazardous waste.?
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.?
S36:Wear suitable protective clothing.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S16:Keep away from sources of ignition.
RIDADR:UN 3077 9/PG 3
WGK Germany:3
RTECS:NI8870000

4.6 Specification

First Aid Measures of Iprodione (CAS NO.36734-19-7):
Ingestion:The possible benefit of early removal of some ingested material by cautious gastric lavage must be weighed against potential complications of bleeding or perforation. Activated charcoal activated charcoal binds most toxic agents and can decrease their systemic absorption if administered soon after ingestion. Activated charcoal: administer charcoal as a slurry (240 ml water/30 g charcoal). Usual dose: 25 to 100 g in adults/adolescents.
Inhalation:Move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with beta2 agonist and corticosteroid aerosols.
Skin:Remove contaminated clothing. Wash exposed area with soap and water. If symptoms persist, seek medical attention. Launder clothing before reuse.
Eyes:Irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist, the patient should be seen in a health care facility.
Storage of Iprodione (CAS NO.36734-19-7):
Store in a cool, dry location, away from food/feed, fertilizers or seed.
Handling:Avoid contact. Adequately decomtaminate all tools and equipment after use. Use protective equipment.
Personal Protection of Iprodione (CAS NO.36734-19-7):
Chemical splash goggles in compliance with OSHA regulations are advised; however, OSHA regulations also permit other type safety glasses. Whre chemical resistant gloves. To prevent repeated or prolonged skin contact, wear impervious clothing and boots.
Fire Fighting of Iprodione (CAS NO.36734-19-7):
Wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Use agent most appropriate to extinguish fire.

4.7 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :
NI8870000
CHEMICAL NAME :
1-Imidazolidinecarboxamide, 3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-
CAS REGISTRY NUMBER :
36734-19-7
BEILSTEIN REFERENCE NO. :
0895003
LAST UPDATED :
199701
DATA ITEMS CITED :
11
MOLECULAR FORMULA :
C13-H13-Cl2-N3-O3
MOLECULAR WEIGHT :
330.19
WISWESSER LINE NOTATION :
T5NVNV EHJ AVMY1&1 CR CG EG

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,501,1991
TYPE OF TEST :
LC50 - Lethal concentration, 50 percent kill
ROUTE OF EXPOSURE :
Inhalation
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>3300 mg/m3/4H
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,501,1991
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>2500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DEVEAA Defense des Vegetaux. (Federation Nationale des Groupements de Protection des Cultures, 149, rue de Bercy, 75595 Paris Cedex, 12, France) V.1- 1947- Volume(issue)/page/year: 30,124,1976
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1700 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DEVEAA Defense des Vegetaux. (Federation Nationale des Groupements de Protection des Cultures, 149, rue de Bercy, 75595 Paris Cedex, 12, France) V.1- 1947- Volume(issue)/page/year: 30,124,1976
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
4 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,501,1991
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FMCHA2 Farm Chemicals Handbook. (Meister Pub., 37841 Euclid Ave., Willoughy, OH 44094) Volume(issue)/page/year: -,C173,1991
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Bird - quail
DOSE/DURATION :
930 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,501,1991
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Bird - duck
DOSE/DURATION :
10400 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,501,1991 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Bird - quail
DOSE/DURATION :
1181 mg/kg/7D-C
TOXIC EFFECTS :
Gastrointestinal - other changes Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - hepatic microsomal mixed oxidase (dealkylation, hydroxylation, etc.) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - other oxidoreductases
REFERENCE :
BECTA6 Bulletin of Environmental Contamination and Toxicology. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1966- Volume(issue)/page/year: 31,479,1983 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Carcinogenicity, Category 2

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H351 Suspected of causing cancer

H410 Very toxic to aquatic life with long lasting effects

Precautionary statement(s)
Prevention

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P273 Avoid release to the environment.

Response

P308+P313 IF exposed or concerned: Get medical advice/ attention.

P391 Collect spillage.

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

9. Other Information
9.0 Merck
13,5096
9.1 BRN
895003
9.2 Uses
Fungicide.
9.3 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.
9.4 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.
9.5 Safety Profile
Moderately toxic by ingestion. When heated to decomposition it emits very toxic fumes of NOx and Cl-.
9.6 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).
9.7 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).
9.8 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.
10. Computational chemical data
  • Molecular Weight: 330.16662g/mol
  • Molecular Formula: C13H13Cl2N3O3
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 329.0333967
  • Monoisotopic Mass: 329.0333967
  • Complexity: 448
  • Rotatable Bond Count: 2
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Topological Polar Surface Area: 69.7
  • Heavy Atom Count: 21
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADccBzMAAGAAAAAAAAAAAAAAAAAWAAAAAwAAAAAAAAAAABAAAAHgIQAAAACCrBkCQzwIPAAACIACVSUACCAAAhBwAAiICIZoiIYCLBk7GUIAholyLIyCcQAAAAAAAAAAKAAAAAAAAABQAAAAAAAAAAAA==
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