| Identification | More | [Name]
Fenclorim | [CAS]
3740-92-9 | [Synonyms]
2-PHENYL-4,6-DICHLORO PYRIMIDINE
4,6-DICHLORO-2-PHENYLPYRIMIDINE
FENCLORIM
SOFIT
4,6-dichloro-2-phenyl-pyrimidin
cga-123407
fenclorime
femclorim
Soft
4,6-dichloro-2-phenylpyrimidineHerbicideSafenerFenclorim
FENCLORIM PESTANAL, 250 MG
Herbicide Safener Fenclorim
fenchlorim
Jiecaoding
2,4-Dichloro-2-phenylpyrimidine
4,6-Dichloro-6-phenylpyrimidine | [EINECS(EC#)]
609-426-7 | [Molecular Formula]
C10H6Cl2N2 | [MDL Number]
MFCD00754193 | [Molecular Weight]
225.07 | [MOL File]
3740-92-9.mol |
| Chemical Properties | Back Directory | [Appearance]
White to off-white solid | [Melting point ]
92-93°C | [Boiling point ]
235.5±33.0 °C(Predicted) | [density ]
1.363±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
Chloroform (Slightly), DMSO (Slightly), Methanol (Sparingly) | [form ]
neat | [pka]
-4.69±0.30(Predicted) | [color ]
Off-White to Pale Yellow | [Water Solubility ]
Insoluble in water | [BRN ]
142293 | [InChI]
InChI=1S/C10H6Cl2N2/c11-8-6-9(12)14-10(13-8)7-4-2-1-3-5-7/h1-6H | [InChIKey]
NRFQZTCQAYEXEE-UHFFFAOYSA-N | [SMILES]
C1(C2=CC=CC=C2)=NC(Cl)=CC(Cl)=N1 | [CAS DataBase Reference]
3740-92-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20:Harmful by inhalation.
R43:May cause sensitization by skin contact. | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
3077 | [WGK Germany ]
2 | [RTECS ]
UV8258400 | [HS Code ]
2933.59.1000 | [HazardClass ]
9 | [PackingGroup ]
III |
| Hazard Information | Back Directory | [Description]
Fenclorim (4,6-dichloro-2-phenylpyrimidine) is a pyrimidine herbicide safener that effectively protects rice (Oryza sativa L.) from the phytotoxicity of certain herbicides. It improves rice tolerance to chloroacetanilide herbicides by enhancing the expression of detoxifying glutathione S-transferase (GST). Compared with seed treatment with safener alone, sequential seed treatment with safener and insecticide minimizes the release of fenclorim without causing residue problems in the ecosystem and harvested rice. | [Chemical Properties]
White to off-white solid | [Uses]
Herbicide safener. | [Definition]
ChEBI: Fenclorim is a member of pyrimidines and an organohalogen compound. | [Synthesis]
The general procedure for the synthesis of 4,6-dichloro-2-phenyl-pyrimidine from 2-phenylpyrimidine-4,6-diol was as follows: 300 ml of phosphoryl chloride was added to 40 g of 2-phenylpyrimidine-4,6-diol. The reaction mixture was heated to reflux at 100 °C for 48 hours. Upon completion of the reaction, the excess phosphoryl chloride was removed by distillation under reduced pressure (20 mbar). Subsequently, 200 ml of chloroform and 100 ml of ice water were added to the reaction mixture and stirred thoroughly for 30 minutes. The pH of the mixture was adjusted to 5-6 with aqueous sodium carbonate. the organic layer was separated and the aqueous phase was extracted three times with 200 mL of chloroform. All chloroform phases were combined, dried with magnesium sulfate, filtered and the chloroform was removed by evaporation under reduced pressure. The resulting crude product can be purified by distillation under reduced pressure or by column chromatography using 60 mesh silica gel (with chloroform as eluent). | [References]
[1] Patent: US2003/162764, 2003, A1
[2] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 8, p. 2627 - 2634
[3] Patent: US6372751, 2002, B1. Location in patent: Example Pr3
[4] Australian Journal of Chemistry, 2015, vol. 68, # 5, p. 814 - 824
[5] Farmaco, 1997, vol. 52, # 1, p. 61 - 65 |
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