The crystal structure of 2-(4-bromophenyl)-4-(2-fluoroethyl)-5,6-dihydro-4H-1,3,4-oxadiazine hydrochloride, an octopaminergic insecticide/miticide

Abstract

Abstract:The crystal structure of 2-(4-bromophenyl)-4-(2-fluoroethyl)-5,6-dihydro-4H-1,3,4-oxadiazine hydrochloride, a new octopamine agonist, has been established by Patterson and Fourier methods and refined to a final R value of 0.0293 for 2123 absorption-corrected observed data. The crystals are monoclinic, n = 14.336(3), b = 12.649(3), c = 6.989(1) A, P = 93.48(1)", and the space group is P2,lc. Its structural similarities with the crystal structure of the invertebrate neurotransmitter, octopamine, are described and support the hypothesis that the pesticidal properties of dihydrooxadiazines are, at least partially, due to perturbation of octopaminergic systems.Key words: dihydrooxadiazine, octopamine agonist.

Synthesis and Octopaminergic-Agonist Activity of 2-(Arylimino)oxazolidines and 2-(Substituted Benzylamino)-2-oxazolines

“…1) and the a-atom (** in Fig.1) of phenyl group in each structure ; these features have been postulated to be important for OA activity. 17,18) RESULTS AND DISCUSSION Typical dose-response experiments were exemplified by OA, AIO 12 and SBO 22 as shown in Fig. 2.…”

Synthesis, in vitro Antimicrobial, and Cytotoxic Activities of New 1,3,4‐Oxadiazin‐5(6H)‐one Derivatives from Dehydroabietic Acid

“…The 1,3,4‐oxadiazines represent an important type of six‐membered heterocycles with two adjacent nitrogen atoms. Many 1,3,4‐oxadiazine derivatives exhibit a great diversity of biological effects, such as antibacterial, antitumor, antileishmanial, miticidal, insecticidal, and monoamine oxidase (MAO) inhibitory activities . Some 1,3,4‐oxadiazine derivatives, e.g., indoxacarb, have been developed as a potent voltage‐dependent sodium channel blocker and have been widely used as a commercially successful insecticide .…”