156963-66-5

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.

Benzobicyclon is used in the development and application of multi-residue method to determine pesticides in agricultural water.

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.

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.

Selective, absorbed through roots and basal stems and translocated. Bleaching inhibition of 4-hydroxyphenyl-pyruvate-dioxygenase.

Herbicide