| Identification | Back Directory | [Name]
3-(2-CHLORO-4-METHYLBENZOYL)-4-PHENYLTHIOBICYCLO[3,2,1]OCT-2-EN-4-ONE | [CAS]
156963-66-5 | [Synonyms]
Benzobicyclon-d5
Benzobicyclon 96%
Benzobicyclon [iso]
BENZOBICYCLON STANDARD
benzobicyclon (bsi, pa iso)
Benzobicyclon@100 μg/mL in Acetonitrile
Benzobicyclon@1000 μg/mL in Acetonitrile
Benzobicyclon, 10 μg /μL in Acetonitrile
3-(2-Chloro-4-mesylbenzoyl)-2-phenylthiobicyclo[3.2.1]oct-2-en-4-one
3-(2-CHLORO-4-METHYLBENZOYL)-4-PHENYLTHIOBICYCLO[3,2,1]OCT-2-EN-4-ONE
3-[2-Chloro-4-(methylsulfonyl)benzoyl]-4-(phenylthio)bicyclo[3.2.1]oct-3-en-2-one
3-(2-chloro-4-methylsulfonylbenzoyl)-2-phenylsulfanylbicyclo[3.2.1]oct-2-en-4-one
Bicyclo[3.2.1]oct-3-en-2-one,3-[2-chloro-4-(methylsulfonyl)benzoyl]-4-(phenylthio)-
3-[(2-chloro-4-methylsulfonylphenyl)-oxomethyl]-2-(phenylthio)-4-bicyclo[3.2.1]oct-2-enone | [Molecular Formula]
C22H19ClO4S2 | [MDL Number]
MFCD09751259 | [MOL File]
156963-66-5.mol | [Molecular Weight]
446.97 |
| Chemical Properties | Back Directory | [Melting point ]
186～190℃ | [Boiling point ]
651.1±55.0 °C(Predicted) | [density ]
1.45±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
Soluble in DMSO | [form ]
Solid | [color ]
Light yellow to brown | [InChI]
InChI=1S/C22H19ClO4S2/c1-29(26,27)16-9-10-17(18(23)12-16)21(25)19-20(24)13-7-8-14(11-13)22(19)28-15-5-3-2-4-6-15/h2-6,9-10,12-14H,7-8,11H2,1H3 | [InChIKey]
VIXCLRUCUMWJFF-UHFFFAOYSA-N | [SMILES]
C12CC(CC1)C(SC1=CC=CC=C1)=C(C(=O)C1=CC=C(S(C)(=O)=O)C=C1Cl)C2=O | [EPA Substance Registry System]
Benzobicyclon (156963-66-5) |
| Hazard Information | Back Directory | [Description]
Benzobicyclon is an unclassified herbicide used to control annual and perennial weeds mainly in rice crops. It has a low aqueous solubility and is not volatile. Environmental persistence data is not available. It has a low to moderate level of toxicity to most biodiversity. It has a low oral toxicity to mammals but little else has been published regarding its impacts on human health. | [Uses]
Benzobicyclon is used in the development and application of multi-residue method to determine pesticides in agricultural water. | [Definition]
ChEBI: 3-[2-chloro-4-(methylsulfonyl)benzoyl]-4-(phenylthio)bicyclo[3.2.1]oct-3-en-2-one is a carbobicyclic compound that is bicyclo[3.2.1]oct-3-en-2-one which is substituted at positions 3 and 4 by 2-chloro-4-(methylsulfonyl)benzoyl and phenylthio groups, respectively. It is a carbobicyclic compound, a cyclic ketone, an organic sulfide, a sulfone, a member of monochlorobenzenes and an aromatic ketone. | [Production Methods]
Benzobicyclon is synthesised through a carefully designed multi-step process that constructs its unique bicyclooctane skeleton and phenylthio-enol ether structure, which are essential for its herbicidal activity. The synthesis typically begins with the preparation of a chlorinated benzoyl intermediate, which is then coupled with a phenylthiol derivative to introduce the sulphur-containing moiety. This is followed by a cyclisation reaction that forms the rigid bicyclic core, often using controlled temperature and catalytic conditions to ensure structural integrity. The final step involves functionalisation to yield the active compound. | [Mechanism of action]
Selective, absorbed through roots and basal stems and translocated. Bleaching inhibition of 4-hydroxyphenyl-pyruvate-dioxygenase. | [Pesticide Type]
Herbicide |
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