10.1134/S0036024407010050
The study investigates the kinetics and mechanism of the alcoholysis of symmetrical dioctylurea in inert solvents, with n-octanol as the alcohol involved. The reaction follows two parallel pathways: one involving the dissociation of initial urea and the other, bimolecular interaction. The researchers used various solvents, including decane, phenetole, o-dichlorobenzene, benzonitrile, and nitrobenzene, to study the influence of solvent properties on the reaction rate. The reaction products were analyzed using proton NMR spectroscopy and photocolorimetry. The study found that the specific rate of the alcoholysis of N,N'-dioctylurea linearly depended on the initial concentration of octanol, indicating that the reaction proceeds via both dissociative and associative routes. The rate constants for these processes were determined and correlated with solvent properties using the Palm–Koppel equation.
10.1002/ps.2780450411
The research aimed to develop a novel synthesis route for the insecticides MTI-800 and desfluoro MTI-800, and to evaluate their insecticidal activities against the tobacco caterpillar Spodoptera litura. The study utilized a tandem Friedel-Crafts acylation and other chemical reactions, diethyl sulfate played a crucial role as a reagent in the alkylation step of the synthesis process. Specifically, it was used to convert the phenolic compound 3-(4-hydroxyphenyl)-3-methyl-2-butanone (2) into 3-(4-ethoxyphenyl)-3-methyl-2-butanone (3). The synthesis process included multiple steps, including acylation, alkylation, aldol condensation, reduction, chlorination, and hydrogenation, to produce the target compounds and their intermediates. The results showed that MTI-800 (7b) and desfluoro MTI-800 (7a) exhibited excellent insecticidal activity comparable to the well-known synthetic pyrethroids fenvalerate and cypermethrin. The study concluded that the central link structure and the presence of a fluoro substitution significantly influenced the insecticidal activity, with the alkane central link showing high activity regardless of the fluoro substitution. The research provides a simpler and cost-effective synthesis route for these insecticides and offers insights into the structure-activity relationship for further development of effective insecticidal compounds.