diamide and anthranil

Novel anthranilic diamides with sulfilimidoyl and sulfoximidoyl functionalities were successfully prepared. Among newly-prepared organosulfur compounds, 3-bromo-1-(3-chloropyridin-2-yl)-

Topics: Animals; Antiviral Agents; Chromatography, Thin Layer; Diamide; Insecticides; Isoxazoles; Spodoptera; Structure-Activity Relationship

Anthranilic diamide insecticides control lepidopteran pests through selectively binding and activating insect ryanodine receptors. In order to search for potential insecticides targeting the ryanodine receptors, a series of anthranilic diamide analogs including trifluoromethyl, nitro, or chloro groups were designed and synthesized by the principle of bioisosterism and structural optimization.. Insecticidal data indicated that some compounds displayed good activity against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella). In particular, the larvicidal activity of 6p against P. xylostella was 95% at 0.01 mg L. Introducing trifluoromethyl, nitro, or chloro groups to a specific position in the N-phenylpyrazole could improve or maintain the activity against M. separata and P. xylostella. 6h and 6p could be used as potential lead compounds for ryanodine receptor modulators. © 2018 Society of Chemical Industry.

Topics: Animals; Diamide; Drug Design; Insecticides; Isoxazoles; Larva; Models, Chemical; Moths; Quantitative Structure-Activity Relationship; Ryanodine Receptor Calcium Release Channel

A series of novel anthranilic diamides derivatives (7a-s) containing halogen, trifluoromethyl group and cyano group were designed, synthesized, and characterized by melting point,

Topics: Animals; Cockroaches; Diamide; Heart Rate; Insecticides; Isoxazoles; Larva; Moths; Quantum Theory; Ryanodine Receptor Calcium Release Channel; Structure-Activity Relationship

Anthranilic diamide derivatives are among the most important classes of synthetic insecticides. Moreover, the 1,2,4-oxadiazole heterocycle, a bioisostere of amide, has been extensively used in pesticides. In order to discover novel molecules with high insecticidal activities, a series of anthranilic diamide analogues containing 1,2,4-oxadiazole rings were designed and synthesised.. A series of novel anthranilic diamide derivatives containing 1,2,4-oxadiazole were obtained, and confirmed by. Compound 3IIl may be used as a potential leading compound for further structural optimisation, and SARs and CoMFA models could provide reliable clues for further structural optimisation. © 2016 Society of Chemical Industry.

Topics: Animals; Chemistry Techniques, Synthetic; Diamide; Drug Design; Insecticides; Isoxazoles; Models, Molecular; Molecular Conformation; Moths; Oxadiazoles; Structure-Activity Relationship

To discover potent insecticides targeting ryanodine receptors (RyRs), a series of novel anthranilic diamides analogues (12a-12u) containing N-substituted phenylpyrazole were designed and synthesized. These compounds were characterized by (1)H NMR, (13)C NMR, and HRMS, and the structure of compound 12u was confirmed by X-ray diffraction. Their insecticidal activities indicated that these compounds displayed moderate to excellent activities. In particular, 12i showed 100 and 37% larvicidal activities against oriental armyworm (Mythimna separata) at 0.25 and 0.05 mg L(-1), equivalent to that of chlorantraniliprole (100%, 0.25 mg L(-1); and 33%, 0.05 mg L(-1)). The activity of 12i against diamondback moth (Plutella xylostella) was 95% at 0.05 mg L(-1), whereas the control was 100% at 0.05 mg L(-1). The calcium-imaging technique experiment results showed that the effects of 12i on the intracellular calcium ion concentration ([Ca(2+)]i) in neurons were concentration-dependent. After the central neurons of Helicoverpa armigera were dyed by loading with fluo-5N and treated with 12i, the free calcium released in endoplasmic reticulum indicated the target of compound 12i is RyRs or IP3Rs. The activation of RyRs by natural ryanodine completely blocked the calcium release induced by 12i, which indicated that RyRs in the central neurons of H. armigera third-instar larvae is the possible target of compound 12i.

Topics: Animals; Calcium Channel Agonists; Diamide; Drug Design; Insect Proteins; Insecticides; Isoxazoles; Larva; Molecular Structure; Moths; Ryanodine Receptor Calcium Release Channel; Structure-Activity Relationship; X-Ray Diffraction

Anthranilic diamide insecticides containing pyridylpyrazole-5-carboxamide are extremely important in modern agriculture. New structurally modified compounds with high insecticidal activity were discovered by designing a series of novel pyridylpyrazole-4-carboxamides (9I to 9IV) and pyridylpyrazole-4-carboxamides (10I to 10IV), the latter designed by the cyclisation of two amides. The structure-activity relationship (SAR) between the two series is of interest.. Two series of novel anthranilic diamides containing pyridylpyrazole-4-carboxamide were synthesised and characterised via melting point, (1)H NMR, (13)C NMR, MS and elemental analyses. The insecticidal activities of these compounds against Plutella xylostella were evaluated. At a concentration of 100 mg L(-1), the compounds with unmodified amide moieties (9I to 9IV) exhibited much better larvicidal activities than the other derivative compounds (10I to 10IV). Most of the compounds 9I to 9IV showed over 90% larvicidal activity at 100 mg L(-1). Furthermore, compounds 9IIIa, 9IIIc, 9IIId and 9IVd displayed significant insecticidal activity at 10 mg L(-1). Density functional theory (DFT) calculation was carried out to provide more information regarding SAR.. Thirty-two new anthranlic diamides containing pyridylpyrazole-4-carboxamide were designed and obtained. SAR analysis and DFT calculation results revealed that the amide moiety had a very important effect on bioactivity. This work has provided information that could aid investigations of novel insecticides.

Topics: Animals; Biological Assay; Diamide; Drug Design; Insecticides; Isoxazoles; Larva; Magnetic Resonance Spectroscopy; Molecular Structure; Moths; Pyrazoles; Structure-Activity Relationship

Many turf managers prefer to control foliage- and root-feeding pests with the same application, so-called multiple-targeting, using a single broad-spectrum insecticide or a premix product containing two or more active ingredients. We compared the impact of a neonicotinoid (clothianidin), a premix (clothianidin + bifenthrin), and an anthranilic diamide (chlorantraniliprole), the main insecticide classes used for multiple targeting, on four species of beneficial insects: Harpalus pennsylvanicus, an omnivorous ground beetle, Tiphia vernalis, an ectoparasitoid of scarab grubs, Copidosoma bakeri, a polyembryonic endoparasitoid of black cutworms, and Bombus impatiens, a native bumble bee. Ground beetles that ingested food treated with clothianidin or the premix suffered high mortality, as did C. bakeri wasps exposed to dry residues of those insecticides. Exposure to those insecticides on potted turf cores reduced parasitism by T. vernalis. Bumble bee colonies confined to forage on white clover (Trifolium repens L.) in weedy turf that had been treated with clothianidin or the premix had reduced numbers of workers, honey pots, and immature bees. Premix residues incapacitated H. pennsylvanicus and C. bakeri slightly faster than clothianidin alone, but otherwise we detected no synergistic or additive effects. Chlorantraniliprole had no apparent adverse effects on any of the beneficial species. Implications for controlling turf pests with least disruption of non-target invertebrates are discussed.

Topics: Animals; Bees; Coleoptera; Diamide; Guanidines; Hymenoptera; Insecticides; Isoxazoles; Neonicotinoids; ortho-Aminobenzoates; Plant Weeds; Pyrethrins; Thiazoles

Anthranilic diamides are one of the most important classes of modern agricultural insecticides. To discover new structure-modified compounds with high activity, series of novel carbonyl thioureas, carbonyl ureas, oxadiazoles, carbonyl thiophosphorylureas, oxadiazole-containing amides, and thiazoline-containing amides were designed through the modification of the amide bridge based on the structure of chlorantraniliprole and were synthesized, and bioassays were carried out. The compounds were characterized and confirmed by melting point, IR, (1)H NMR, and elemental analyses or HRMS. Preliminary bioassays indicated that some compounds exhibited significant insecticidal activities against oriental armyworm, diamondback moth, beet armyworm, corn borer, and mosquito. Among them, trifluoroethoxyl-containing carbonyl thiourea 20a showed best larvicidal activity against oriental armyworm, with LC50 and LC95 values of 0.1812 and 0.7767 mg/L, respectively. Meanwhile, 20c and 20e showed 86 and 57% death rates against diamondback moth at 0.005 mg/L, and the LC50 values of the two compounds were 0.0017 and 0.0023 mg/L, respectively, which were lower than that of the control chlorantraniliprole. The relationship between structure and insecticidal activity was discussed, and the HF calculation results indicated that the carbonyl thiourea moiety plays an important role in the insecticidal activity. The present work demonstrated that the trifluoroethoxyl-containing carbonyl thioureas can be used as lead compounds for further development of novel insecticides.

Topics: Animals; Biological Assay; Diamide; Drug Design; Insecta; Insecticides; Isoxazoles; Molecular Structure; Structure-Activity Relationship

The Asian citrus psyllid, Diaphorina citri (Hemiptera: Psyllidae), is the most destructive pest of citrus in Florida. The development of insecticide resistance in several populations of D. citri has been documented. There is an urgent need to develop and integrate novel tools for the successful management of D. citri and also to prevent the development of insecticide resistance.. The effects of a relatively newer chemistry, cyantraniliprole, against D. citri were investigated. The contact toxicity of cyantraniliprole was 297-fold higher against D. citri than its primary parasitoid, Tamarixia radiata (Hymenoptera: Eulophidae). D. citri settled and fed less on cyantraniliprole-treated plants than controls at concentrations as low as 0.025 and 0.125 µg AI mL⁻¹ respectively. D. citri egg production, first-instar emergence and adult emergence were significantly reduced on plants treated with 0.25, 0.02 and 0.25 µg AI mL⁻¹ of cyantraniliprole, respectively, when compared with control plants. Under field conditions, foliar and drench treatments with cyantraniliprole (1436.08 g ha⁻¹) reduced numbers of D. citri adults and nymphs, as well as of a secondary pest, citrus leafminer, Phyllocnistis citrella (Lepidoptera: Gracillariidae), more than a standard insecticide.. These results suggest that cyantraniliprole should be a valuable new tool for rotation into D. citri management programs. For insecticide resistance management, cyantraniliprole may be particularly useful for rotation with neonicotinoids. In addition, cyantraniliprole was much less toxic to T. radiata than to D. citri and thus may have less impact on biological control than other currently used broad-spectrum insecticides, such as organophosphates and pyrethroids.

Topics: Animals; Citrus; Diamide; Hemiptera; Insecticides; Isoxazoles; ortho-Aminobenzoates; Plant Diseases; Pyrazoles

In searching for environmentally benign insecticides with high activity, low toxicity and low residue, two series of novel anthranilic diamide containing methyl ether and isopropyl ether group were designed and synthesized. All of the compounds were characterized by (1)H NMR spectroscopy, (13)C NMR spectroscopy and elemental analysis. The single crystal structure of 19j was determined by X-ray diffraction. The insecticidal activities of the new compounds were evaluated. The results showed that some compounds exhibited excellent insecticidal activities against Lepidoptera pests. Among this series, compound, 18l showed 100 % larvicidal activity against Mythimna separate Walker, Plutella xylostella Linnaeus and Laphygma exigua Hubner at the test concentration, which was equal to the available chlorantraniliprole.

Topics: Animals; Diamide; Ethers; Insecticides; Isoxazoles; Larva; Lepidoptera; Magnetic Resonance Spectroscopy; Maleates; Methyl Ethers; Molecular Structure; ortho-Aminobenzoates; Structure-Activity Relationship; X-Ray Diffraction

In order to look for novel insecticides targeting the ryanodine receptor, four new series of anthranilic diamides containing modified N-pyridylpyrazoles were designed and synthesized. All of the compounds were characterized and confirmed by (1)H NMR, (13)C NMR, and HRMS. The single crystal structure of 10c was determined by X-ray diffraction. Their insecticidal activities against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella) indicated that most of the compounds showed moderate to high activities at the tested concentration, while compound 19 showed comparable higher activity at the concentration of 0.125 mg/L. The preliminary structure-activity relationship (SAR) was discussed.

Topics: Animals; Diamide; Insecticides; Isoxazoles; Molecular Structure; Moths; Pyrazoles; Structure-Activity Relationship