161326-34-7

Basic information

• Product Name: FENAMIDONE
• Synonyms: REASON;(S)-1-ANILINO-4-METHYL-2-METHYLTHIO-4-PHENYL-2-IMIDAZOLIN-5-ONE;RPA 407213;UTILIS;Mepanipyrim, Pestanal;4H-Imidazol-4-one, 3,5-dihydro-5-methyl-2-(methylthio)-5-phenyl-3-(phenylamino)-, (5S)-;fenamidone (bsi,iso);fenamidone (ISO) (S)-5-methyl-2-methylthio-5-phenyl-3-phenylamino-3,5-dihydroimidazol-4-one
• CAS NO: 161326-34-7
• Molecular Formula: C₁₇H₁₇N₃OS
• Molecular Weight: 311.4
• Mol File: 161326-34-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 137°
• Boiling Point: 443°Cat760mmHg
• Flash Point: 221.7°C
• Appearance: /
• Density: 1.285
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.638
• Storage Temp.: 0-6°C
• PKA: 0.49±0.40(Predicted)
• CAS DataBase Reference: FENAMIDONE(CAS DataBase Reference)
• NIST Chemistry Reference: FENAMIDONE(161326-34-7)
• EPA Substance Registry System: FENAMIDONE(161326-34-7)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61
• RIDADR: UN3077 9/PG 3
• WGK Germany: 2
• Hazardous Substances Data: 161326-34-7(Hazardous Substances Data)

Usage

Description

Fenamidone, also known as RPA 407213 or (S)-5-methyl-2-methylthio-5-phenyl-3-phenylamino-3,4-dihydroimidazol-4-one, is a complex III inhibitor that belongs to the imidazolinone chemical class. It is a white woolly powder with the following characteristics: melting point (mp) = 137°C, water solubility = 7.8 mg/L, logarithm of the partition coefficient (logP) = 2.8, and vapor pressure (vp) = 3.4×10^-7 Pa. Fenamidone was first described by Mercer et al. in 1998, and only the S-enantiomer exhibits antifungal activity, allowing for a reduction in application rates compared to the racemic mixture.

Uses

Used in Agriculture:
Fenamidone is used as a fungicide for the control of Oomycete diseases such as downy mildew and certain leaf spot diseases. It is effective against a wide range of fungal pathogens, providing protection to crops and improving yield and quality.
Used in Crop Protection:
Fenamidone is employed as a crop protection agent, targeting various fungal infections that can damage or destroy crops. Its selective activity against the S-enantiomer makes it an efficient and cost-effective option for farmers and growers.
Used in Plant Pathology Research:
Fenamidone is utilized in plant pathology research to study the mechanisms of action and resistance development in fungal pathogens. This knowledge can contribute to the development of new strategies for disease management and the improvement of existing fungicides.

Hazard

Moderately toxic by ingestion and skin contact. Low toxicity by inhalation.

Toxicity evaluation

Fenamidone has an acute oral LD50 > 5,000 and an acute dermal LD50 > 2,000 mg/kg in rats. Fenamidone is not a skin or eye irritant, is negative in the Ames test, and is nonteratogenic. It shows low toxicity to birds in acute and dietary studies but has a 96-h fish LC50 of 0.74 mg/L.

InChI:InChI=1/C17H17N3OS/c1-17(13-9-5-3-6-10-13)15(21)20(16(18-17)22-2)19-14-11-7-4-8-12-14/h3-12,19H,1-2H3/t17-/m0/s1

Upstream product

• 252268-16-9 (+)-[methyl (2S)-2-isothiocyanato-2-phenylpropionate] 
• 74-88-4 methyl iodide 
• 100-63-0 phenylhydrazine 

Downstream Products

• 161326-48-3 (+)-(4S)-4-methyl-2-methoxy-4-phenyl-1-phenylamino-2-imidazolin-5-one 

Relevant articles and documents

Fungicidal 2-imidazolin-5-ones and 2-imidazoline-5-thiones

Fungicidal 2-imidazolin-5-ones and 2-imidazoline-5-thiones, processes for their preparation, fungicidal compositions containing them, and methods of using them to treat or prevent fungal disease in crops.

Fungicidal 2-imidazolin-5-ones and 2-imidazoline-5-thiones

Fungicidal 2-imidazolin-5-ones and 2-imidazoline-5-thiones, processes for their preparation, fungicidal compositions containing them and methods of using them to treat or prevent fungal disease in crops.