FENPICLONIL

FENPICLONIL Basic information
Product Name:FENPICLONIL
Synonyms:FENPICLONIL;GAMBIT;BERET;3-(2,3-dichlorophenyl)-4-cyanopyrrole;4-(2,3-dichlorophenyl)-1h-pyrrole-3-carbonitril;4-(2,3-dichlorophenyl)-1H-pyrrole-3-carbonitrile;4-cyano-3-(2,3-dichlorophenyl)pyrrole;cga142705
CAS:74738-17-3
MF:C11H6Cl2N2
MW:237.08
EINECS:
Product Categories:Pyroles;Alpha sort;E-GAlphabetic;F;FA - FLPesticides;Fungicides;Pesticides&Metabolites
Mol File:74738-17-3.mol
FENPICLONIL Structure
FENPICLONIL Chemical Properties
Melting point 152.9℃
Boiling point 378.43°C (rough estimate)
density 1.4052 (rough estimate)
vapor pressure 1.1 x 10-7 Pa (25 °C)
refractive index 1.6400 (estimate)
Water Solubility 4.8 mg l-1 in water at 25 °C
form neat
pka13.63±0.50(Predicted)
Merck 13,4016
BRN 5433281
EPA Substance Registry System1H-Pyrrole-3-carbonitrile, 4-(2,3-dichlorophenyl)- (74738-17-3)
Safety Information
Hazard Codes Xn
Risk Statements 20
RIDADR 3077
WGK Germany 2
RTECS UX9347500
HazardClass 9
PackingGroup III
ToxicityLD50 in rats, mice, rabbits (mg/kg): >5000 orally; LD50 dermally in rats: >2000 mg/kg; LC50 (4 hr) in rats: >1502 mg/m3 by inhalation (Nevill)
MSDS Information
FENPICLONIL Usage And Synthesis
DescriptionFenpiclonil is the first phenylpyrrole fungicide developed by Ciba Geigy (now belonging to the portfolio of Syngenta Crop Protection AG) for seed treatment. Different formulation types have been used for its commercialization either in solo (trade name “Beret”) or in mixture with other fungicides, as for instance, imazalil (“Beret Special”) or carboxin + imazalil (“Beret Universal”).
UsesAgricultural fungicide.
UsesFenpiclonil is a systemic and contact fungicide that provides protective control of seed-borne pathogens of cereals such as snow mould and bunt caused by Fusarium spp., Tilletia caries, Septoria nodorum, etc. It also controls leaf spot, brown foot rot and ear blight in non-cereal crops.
DefinitionChEBI: A member of the class of pyrroles carrying cyano and 2,3-dichlorophenyl substituents at positions 3 and 4 respectively. A fungicide used mainly to control seed-borne pathogens in cereal crops.
General DescriptionFenpiclonil is a phenylpyrrole fungicide and a structural analogue of the antibiotic pyrrolnitrin found to be toxic to representatives of Ascomycetes, Basidiomycetes, and Deuteromycetes.
Metabolic pathwayLimited data are available in the open literature. Information presented in this summary was abstracted from the data evaluation published by the Pesticide Safety Directorate (PSD, 1993). Fenpiclonil is stable to hydrolytic and soil degradation. Photolytic degradation is rapid. Hydroxylation and oxidation of the pyrrole ring are the primary metabolic reactions in plants and animals (Scheme 1).
DegradationFenpiclonil (1) is stable to hydrolytic degradation (up to 70 °C) over the pH range 5-9.
Fenpiclonil degraded rapidly in water (pH 7) when samples were irradiated under a mercury arc lamp (>290 nm) with an estimated DT50 values of <1 hour. At least eight unidentified degradation products were observed
Seeddressing agent 3-(2-CHLORO-PHENYL)-1H-PYRROLE 3-CYANOPYRROLE 3-CYANO-4-PHENYL-PYRROLE 3-Phenyl-1H-pyrrole FENPICLONIL

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