Diamide derivatives containing a trifluoromethylpyridine skeleton:Design,synthesis,and insecticidal activity

Diamide derivatives are biologically active molecules that have been widely applied in recent years in research on pesticides,especially insecticides.Using a simple and environmentally friendly scheme,a series of new diamide derivatives containing a trifluoromethylpyridine skeleton was designed,synthesized,and confirmed by^(1)H,^(19)F and^(13)C NMR,and HR-MS.Their insecticidal activities against Plutella xylostella and Helicoverpa armigera were measured and the relationship between structure and activity was investigated.Eight of the title compounds(D2,D5,D10,D21,D28,D29,D30 and D33)showed 100%activity against P.xylostella at 500 mg L^(-1).One compound,D33,still showed 100%activity against P.xylostella at 100 mg L^(-1)and had the lowest LC_(50)(lethal concentration 50%,3.7 mg L^(-1))among the synthesized compounds.Molecular docking analysis revealed that D33 could be thoroughly embedded in the active pocket of the ryanodine receptor via hydrogen bonding in a manner similar to the commercial insecticide chlorantraniliprole.

Discovery of Novel Anthranilic Diamide Derivatives Bearing Sulfoximine Group as Potent Insecticide Candidates

The fall armyworm,Spodoptera frugiperda(S.frugiperda),represents the most resistant insect species and poses serious threat to grain yield.Chlorantraniliprole(CHL),which targets the ryanodine receptors(RyRs)in insects,has demonstrated the efficacy in controlling S.frugiperda.Nevertheless,this has led to emerging resistance in several countries.To counter this resistance,a viable approach involves the development of novel compounds that bind against RyRs via distinct binding sites or modes.In this study,a series of 22 novel anthranilic diamide derivatives was designed and synthesized,and their insecticidal activities were evaluated.Most of these derivatives showed moderate to good insecticidal activity against S.frugiperda and Mythimna separata.Time-lapse fluorescence measurements of endoplasmic reticulum luminal calcium revealed that most derivatives elicited cellular responses similar as CHL when assessed on HEK293 cells expressing S.frugiperda ryanodine receptors(SfRyRs).The mode of action of compound 13a was studied and verified on the isolated neurons by calcium imaging technique.Finally,molecular docking analysis was employed to predict the binding mechanism of compound 13a against SfRyRs.Overall,these novel diamide derivatives hold promise as a valuable resource for guiding the future design of insecticidal compounds targeting RyRs.

Targeted Synthesis of Anthranilic Diamides Insecticides Containing Trifluoroethoxyl Phenylpyrazole

A series of novel anthranilic diamides analogues(9a-9t)containing trifluoroethoxyl pyrazole moiety was designed and synthesized and their insecticidal bioactivities against Mythimna separata(Walker,M.separata)and Plutellaxylostella(P.xylostella)were evaluated.The structures of the title compounds were confirmed by^(1)H NMR,^(13)C NMR and HRMS.Preliminary insecticidal activities showed that some of the title compounds possessed good to excellent bioactivities towards M.separata and P.xylostella.Compounds 9c and 9t exhibited 100%mortality rate against M.separate at 0.2 mg/L.For the P.xylostella,the synthesized compounds(9c-9e,9i and 9o)showed 70%,80%,75%,65%and 60%insecticidal activities at 1×10^(−6)mg/L,respectively,higher than that of chlorantraniliprole(0).Based on excellent insecticidal activities,the mode of the action was tested by the calcium-imaging technique,the results of which demonstrated that the novel compounds shared the same target with chlorantraniliprole.The binding pose of the most active compound 9t in RyRs of P.xylostella was predicted by molecular docking,which showed that compound 9t interacted with the residues Glu140(A)and His147(A)via hydrogen bond.

Separation of chiral phosphorus compounds on the substituted P-cyclodextrin stationary phase in normal-phase liquid chromatog-raphy

The separation of enantiomers of a series of eighteen novel nitrogen mustard linked phosphoryl diamide derivatives was investigated on the prepared phenyl carbamate derivative β-cy-clodextrin bonded phase in normal-phase HPLC. Some of the enantiomers could be separated in baseline. The chiral recognition mechanism was also suggested for the separation of chiral phosphorus organic compounds.