1263133-33-0

Triflumezopyrim, a mesoionic insecticide, has high efficiency at a low dosage, and is mainly used to control hopper species. Triflumezopyrim mainly acts on the nicotinic acetylcholine receptor (nAChR) inhibition, which is very highly efficient, rapidly effective, and nearly nontoxic to nontarget arthropods[1].

Triflumezopyrim is commercially produced through a multi-step synthesis that begins with the preparation of the key intermediate N-[(5-pyrimidinyl)methyl]-2-pyridinamine via a one-pot sequence. First, the imidization of pyrimidine-5-carboxaldehyde with 2-aminopyridine in refluxing toluene using catalytic p-toluenesulfonic acid and a Dean-Stark trap for water azeotropic removal is undertaken yielding the imine N-(5-pyrimidinylmethylene)-2-pyridinamine. Secondly, methanol is added to form the methoxy adduct N-[methoxy(5-pyrimidinyl)methyl]-2-pyridinamine, and finally selective reduction with sodium borohydride in toluene is conducted followed by aqueous workup, extraction into dichloromethane, concentration, and crystalliz=sation from dichloromethane/heptanes. This intermediate is then coupled with a pre-formed malonyl derivative bearing the 3-(trifluoromethyl)phenyl group—typically a dithiomalonate or equivalent activated species, under basic conditions via enolization and condensation, followed by cyclisation to form the crude product.

Induces an adverse pysiological reaction. Nicotinic acetylcholine receptor (nAChR) channel blocker.

[1] Chen L, et al. The population growth, development and metabolic enzymes of the white-backed planthopper, Sogatella furcifera (Hemiptera: Delphacidae) under the sublethal dose of triflumezopyrim. Chemosphere. 2020;247:125865. DOI:10.1016/j.chemosphere.2020.125865
[2] Wen S, Liu C, et al. Oxidative stress and DNA damage in earthworm (Eisenia fetida) induced by triflumezopyrim exposure. Chemosphere. 2021 Feb;264(Pt 2):128499. DOI:10.1016/j.chemosphere.2020.128499
[3] Mishra R, et al. Residue dynamics and bio-efficacy of triflumezopyrim against Nilaparvata lugens and non-targeted effect on natural enemies in a rice ecosystem. Environ Sci Pollut Res Int. 2022 Apr;29(20):30206-30216. DOI:10.1007/s11356-022-18551-1
[4] Wang L, et al. Toxicity and Sublethal Effect of Triflumezopyrim Against Red Imported Fire Ant (Hymenoptera: Formicidae). J Econ Entomol. 2020 Aug 13;113(4):1753-1760. DOI:10.1093/jee/toaa083

Insecticide