Synthesis and acaricidal activity of novel pyrazole-heterocyclic anthranilic amides

Pyrazole-heterocyclic anthranilic amides were synthesized from chlorantraniliproles and fipronils. All 24 new compounds were characterized by 1H NMR, IR and APCI-MS. Compounds 5-bromo-N-(4-chloro-2-methyl-6-(methyl-carbamoyl)phenyl)-1-(2,6-dichloro-4-(trifluoromethyl)-phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole -3-carboxamide (5k) and 5-bromo-N-(4-bromo-2-methyl-6-(methylcarbamoyl)phenyl)-1-(2, 6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoro-methyl)sulfinyl)-1H-pyrazole-3-carboxamide(5l) exhibited 100% mortality against Tetranychus cinnabarinus at 500 mg/L. At 100 mg/L, the mortality dropped to 30% and 50%, respectively. These results provided further insights into the relationship between the structures and biological activity of this novel pyrazole-heterocyclic anthranilic amides.