Anthranilic diamides are one of the most important classes of modern agricultural insecticides, among which Chlorantraniliprole (Rynaxypyr) and Cyantraniliprole (Cyazypyr) are two important commercial insecticides as highly potent and selective activators of the insect ryanodine receptor (RyR). To discover new structure-modified compounds with high activities, series of compounds were designed by changing amide bridge to carbonyl thiourea, carbonyl urea, oxadiazole, carbonyl thiophosphorylurea, N-hydroxyl amide, �-lactam, thiazolinone, aziridine, thiazoline amide, and aminomethylphosphonate moieties with substituted N-pyridylpyrazole ring based on the structure of Chlorantraniliprole and were synthesized successfully. Preliminary bioassays indicated that some types of compounds exhibited significant insecticidal activities. Among them, one of trifluoroethoxyl-containing carbonyl thioureas showed best larvicidal activity against oriental armyworm, with LC50 and LC95 values of 0.1812 mg/L and 0.7767 mg/L, respectively. Meanwhile two of this kind of compounds possessed LC50values of 0.0017 mg/L and 0.0023 mg/L against diamondback moth, respectively, and which were prior to that of the control Chlorantraniliprole. The relationship between structure and insecticidal activity will be discussed. Furthermore, some compounds with amide bridge-modified structures were found to have excellent fungicidal activities, though they showed weak insecticidal activities.

Studies on the amide bridge modification of anthranilic diamide insecticides and biological activities based on the insect RyR

248th National Meeting (2014)

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