| Identification | Back Directory | [Name]
Proquinazid | [CAS]
189278-12-4 | [Synonyms]
dpx-kq926
Proquinazid [iso]
Proquinazid Solution
Proquinazid in Acetonitrile
Proquinazid 100 μg/ml Acetonitrile
Proquinazid@100 μg/mL in Acetonitrile
6-iodo-2-propoxy-3-propylquinazolin-4(3H)-one
L16542000CY Proquinazid 10μg/mLin Cyclohexane
4(3H)-Quinazolinone, 6-iodo-2-propoxy-3-propyl- | [Molecular Formula]
C14H17IN2O2 | [MDL Number]
MFCD11616763 | [MOL File]
189278-12-4.mol | [Molecular Weight]
372.2 |
| Chemical Properties | Back Directory | [storage temp. ]
Hygroscopic, -20°C Freezer, Under inert atmosphere | [solubility ]
DMSO (Slightly, Heated), Methanol (Slightly) | [color ]
White to Off-White | [Henry's Law Constant]
3.3×101 mol/(m3Pa) at 25℃, Maniere et al. (2011) | [Major Application]
agriculture
environmental | [InChI]
1S/C14H17IN2O2/c1-3-7-17-13(18)11-9-10(15)5-6-12(11)16-14(17)19-8-4-2/h5-6,9H,3-4,7-8H2,1-2H3 | [InChIKey]
FLVBXVXXXMLMOX-UHFFFAOYSA-N | [SMILES]
CCCOC1=Nc2ccc(I)cc2C(=O)N1CCC | [EPA Substance Registry System]
4(3H)-Quinazolinone, 6-iodo-2-propoxy-3-propyl- (189278-12-4) |
| Hazard Information | Back Directory | [Chemical Properties]
Pure product is white crystalline solid, melting point 61.5-62 ℃, vapor pressure 9 × 10-2mPa (25 ℃), KowIgP = 5.5, Henry's constant 3 × 10-2Pa - m3/mol, relative density 1.57 (20 ℃). Solubility in water 0.93 mg/L (pH 7.25°C). Solubility in organic solvents (25℃, g/L): acetone, dichloromethane, DMF, ethyl acetate, n-hexane, n-octanol, o-xylene in >250 (g/kg ,25℃), acetonitrile 154, methanol 136.Stability:pH 4, 7 and 9, hydrolytically stable (20℃). No decomposition between pH 2.4 and 11.6. | [Uses]
6-?Iodo-?2-?propoxy-?3-?propylquinazolin-?4(3H)?-?one is a fungicidal agent. Pesticide. | [Definition]
ChEBI: A member of the class of quinazolines that is quinazolin-4-one substituted at positions 2, 3 and 6 by propoxy, propyl and iodo groups respectively. A fungicide with the potential to control powdery mildew in a range of crops including cereals and grapes. | [Production Methods]
Proquinazid is commercially produced via a multi-step synthesis starting from 2-amino-4,6-dichlorobenzoic acid, which undergoes condensation with 3-iodobenzoyl chloride in the presence of triethylamine in dichloromethane to form the amide intermediate. This is cyclised to the quinazolinone core using ammonium acetate under reflux in acetic acid, followed by selective iodination at the 6-position with N-iodosuccinimide in DMF. The iodo group is then replaced via palladium-catalysed Sonogashira coupling with 1-propyne, yielding proquinazid. | [General Description]
Proquinazid belongs to the quinazolinone class of fungicides. | [Mechanism of action]
Preventative and curative activity. Translocates and inhibits appressoria development stopping infections. Signal transduction | [Pesticide Type]
Fungicide |
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Sigma-Aldrich
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