Tyclopyrazoflor is an anthranilamide compound with pesticidal activity.
ChEBI: Tyclopyrazoflor is a member of the class of pyrazoles that is 1H-pyrazole which is substituted at positions 1, 3 and 4 by a pyridin-3-yl group, chloro group and an ethyl{3-[(3,3,3-trifluoropropyl)sulfanyl]propanoyl}nitrilo group, respectively. It is an insecticide from Dow AgroSciences LLC. It has a role as an insecticide. It is an organofluorine compound, a member of pyrazoles, a member of pyridines, a tertiary carboxamide, an organic sulfide and an organochlorine compound.
Tyclopyrazoflor is produced commercially through a process that begins with a [3+2] cyclization of 3-hydrazinopyridine hydrochloride and methyl acrylate to form a pyrazolidinone, followed by chlorination and oxidation to a disubstituted pyrazole. Regioselective nitration, reduction to the aminopyrazole, and acylation with 3-((3,3,3-trifluoropropyl)thio)propanoyl chloride yield a secondary amide intermediate, which is then alkylated to the final product. Key innovations include a thiol-ene reaction for the trifluoropropyl thioester precursor, achieving high regioselectivity using a benzoyl peroxide/N,N-dimethylaniline initiator system at low temperatures in semibatch mode, and an Ullmann coupling of N-(3-chloro-1H-pyrazol-4-yl)acetamide with 3-bromopyridine, catalysed by copper(I) chloride and 1,2-dimethylethylenediamine.
Unclear but thought to interfer with an insect's nervous system, specifically its neurotransmission, interacting with the chordotonal TRPV channels
