Discovery of Novel Thiazolyl Anthranilic Diamide Derivatives as Insecticidal Candidates

Background

Agricultural pests have caused huge losses in agricultural production and threaten global food security. Synthetic insecticides remain the major control method. However, with the rapid development of pest resistance and the increasingly stringent regulations on pesticide usage, the development of efficient insecticides with novel structures is particularly urgent.

Results

26 novel anthranilic diamide derivatives containing thiazole moiety were designed based on the scaffold hopping strategy. Bioassay results indicated that compound 6e exhibited excellent insecticidal activity against a susceptible strain of diamondback moth (Plutella xylostella) with the median lethal concentration (LC₅₀) being 0.65 mg/L, which was similar to chlorantraniliprole (LC₅₀ = 0.53 mg/L). When treated on larvae of Plutella xylostella that were chlorantraniliprole‐resistant, compound 6e showed marginally lower insecticidal activity than chlorantraniliprole (LC₅₀ = 50.45 mg/L and 31.98 mg/L, respectively), suggesting a cross‐resistance of compound 6e with chlorantraniliprole (resistance ratios, 77.6‐fold and 60.3‐fold, respectively). Compound 6e also showed good insecticidal activity against fall armyworm and beet armyworm with the mortalities of pests being 74% and 64%, respectively, at the concentration of 5 mg/L. In addition, compounds 6e and 12a showed delayed toxicity against red imported fire ant with mortality rates being 84% and 85% after 5 days of treatment at 1.0 mg/L, which was superior to chlorantraniliprole.

Conclusion

The introduction of thiazole into anthranilic diamide scaffolds resulted in insecticidal leads 6e and 12a with excellent insecticidal activities and potential application in controlling red imported fire ants. The work also guides the discovery of insecticidal molecules with thiazole‐containing anthranilic diamide scaffold.

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