diamide and anthranilic-acid

diamide has been researched along with anthranilic-acid* in 7 studies

Other Studies

7 other study(ies) available for diamide and anthranilic-acid

ArticleYear
Synthesis and insecticidal activity study of novel anthranilic diamides analogs containing a diacylhydrazine bridge as effective Ca
    Chemical biology & drug design, 2018, Volume: 92, Issue:5

    Anthranilic diamides is a class of insecticides target at ryanodine receptors (RyRs). To discover potent insecticides targeting at RyRs, a series of novel anthranilic diamides with a diacylhydrazine bridge were designed and synthesized. Their insecticidal activities were evaluated and a preliminary structure-activity relationship (SAR) was summarized. In particular, compound 5g exhibited good lethality against oriental armyworm (Mythimna separata) at a concentration of 5 mg/L. The calcium imaging experimental results indicated that the compound 5g can serve as effective insect Ca

    Topics: Animals; Calcium; Diamide; Drug Design; Hydrazines; Insecticides; Neurons; ortho-Aminobenzoates; Spodoptera; Structure-Activity Relationship

2018
Bicyclic heterocyclic anthranilic diamides as ryanodine receptor modulators with insecticidal activity.
    Bioorganic & medicinal chemistry, 2016, Feb-01, Volume: 24, Issue:3

    The diamide insecticides act on the ryanodine receptor (RyR). The synthesis of various bicyclic anthranilic derivatives is reported. Their activity against the insect ryanodine receptor (RyR) and their insecticidal activity in the greenhouse is presented, as well as structure activity relationship considerations.

    Topics: Animals; Aphids; Diamide; Dose-Response Relationship, Drug; Insecticides; Molecular Structure; ortho-Aminobenzoates; Ryanodine Receptor Calcium Release Channel; Spodoptera; Structure-Activity Relationship

2016
Synthesis and insecticidal evaluation of novel anthranilic diamides containing N-substitued nitrophenylpyrazole.
    Bioorganic & medicinal chemistry, 2014, Jan-01, Volume: 22, Issue:1

    To cope with developing pest resistance and ecological problems associated with conventional insecticides and to search for potent insecticides targeting at ryanodine receptor (RyR), a series of novel anthranilic diamides containing N-substitued nitrophenylpyrazole were designed and synthesized. The insecticidal activities of target compounds against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella) were evaluated in our greenhouse by bio-assay tests and the relative structure-activity relationships were briefly discussed. Most compounds exhibited moderate to high activities, in which G₇ and K₅ showed high activity against oriental armyworm and K₂ and K₄ against diamondback moth even better than the control-chlorantraniliprole. The calcium imaging technique was used to investigate the effects of several typical title compounds on the [Ca(2+)](i), especially the effects of G₇ on the intracellular calcium ion concentration ([Ca(2+)](i)) in neurons, which indicated that some title compounds were potent activators of the RyR.

    Topics: Diamide; Drug Design; Molecular Structure; ortho-Aminobenzoates; Pyrazoles; Structure-Activity Relationship

2014
Novel chlorantraniliprole derivatives as potential insecticides and probe to chlorantraniliprole binding site on ryanodine receptor.
    Bioorganic & medicinal chemistry letters, 2014, Apr-15, Volume: 24, Issue:8

    The lepidopteran pests such as diamondback moth are the regularly harmful pests of crops in the world, which brings enormous losses in crop production. Chlorantraniliprole is an anthranilic diamide insecticide registered for the control of lepidopteran pests with high insecticidal activity, however with uncertain binding site action target of chlorantraniliprole on ryanodine receptor, a series of new chlorantraniliprole derivatives were synthesized and the insecticidal activities of these compounds against diamondback moth were evaluated with chlorantraniliprole and indoxacarb as control. All compounds except 8h, 8p and 8t exhibited varying degree of activities against diamondback moth. Especially, compounds 8c, 8i, 8k and 8l displayed good insecticidal activities against diamondback moth and the activities are even better than that of indoxacarb during 72 h period. The Ki values of all synthesized compounds were calculated through autodocking program respectively. The relationship between calculation value of molecular docking and results of insecticidal activities indicated that the proposed specific receptor, the membrane-spanning domain protein of diamondback moth ryanodine receptor in our study might have chlorantraniliprole binding sites.

    Topics: Animals; Binding Sites; Diamide; Inhibitory Concentration 50; Insecticides; Models, Biological; Molecular Structure; Moths; ortho-Aminobenzoates; Protein Binding; Ryanodine Receptor Calcium Release Channel

2014
Synthesis, insecticidal activity, and structure-activity relationship (SAR) of anthranilic diamides analogs containing oxadiazole rings.
    Organic & biomolecular chemistry, 2013, Jun-28, Volume: 11, Issue:24

    A series of anthranilic diamides analogs (3–11, 16–24) containing 1,2,4- or 1,3,4-oxadiazole rings were synthesized and characterized by (1)H NMR, MS and elemental analyses. The structure of 3-bromo-N-(2-(3-(4-bromophenyl)-1,2,4-oxadiazol-5-yl)-4-chloro-6-methylphenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide (18, CCDC-) was determined by X-ray diffraction crystallography. The insecticidal activities against Plutella xylostella and Spodoptera exigua were evaluated. The results showed that most of title compounds displayed good larvicidal activities against P. xylostella, especially compound 3-bromo-N-(4-chloro-2-methyl-6-(5-(methylthio)-1,3,4-oxadiazol-2-yl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide (6), which displayed 71.43% activity against P. xylostella at 0.4 μg mL(-1) and 33.33% against S. exigua at 1 μg mL(-1). The structure-activity relationship showed that compounds decorated with a 1,3,4-oxadiazole were more potent than compounds decorated with a 1,2,4-oxadiazole, and different substituents attached to the oxadiazole ring also affected the insecticidal activity. This work provides some hints for further structure modification and the enhancement of insecticidal activity.

    Topics: Animals; Crystallography, X-Ray; Diamide; Dose-Response Relationship, Drug; Insecticides; Larva; Models, Molecular; Molecular Structure; Moths; ortho-Aminobenzoates; Oxadiazoles; Structure-Activity Relationship

2013
Anthranilic acid-based diamides derivatives incorporating aryl-isoxazoline pharmacophore as potential anticancer agents: design, synthesis and biological evaluation.
    European journal of medicinal chemistry, 2012, Volume: 54

    A series of novel anthranilic diamides derivatives containing aryl-isoxazoline moiety were designed and synthesized as a part of our ongoing search for potential anticancer agents. Their structures were confirmed by (1)H NMR, (13)C NMR and ESI-MS analyses. The preliminary assays showed that some of the compounds displayed moderate to good antitumor activities against human lung cancer (NCI-H460), hepatocellular liver carcinoma (HepG2), gastric cancer (SGC-7901 and BGC-823) and breast epithelial adenocarcinoma (MCF-7) cell lines at μM level, which might be developed as novel lead scaffold for potential anticancer agents.

    Topics: Antineoplastic Agents; Cell Line, Tumor; Cell Proliferation; Diamide; Drug Design; Humans; Inhibitory Concentration 50; Isoxazoles; ortho-Aminobenzoates

2012
Synthesis and insecticidal activities of novel anthranilic diamides containing acylthiourea and acylurea.
    Journal of agricultural and food chemistry, 2012, Aug-08, Volume: 60, Issue:31

    Two series of anthranilic diamides containing acylthiourea and acylurea linkers were designed and synthesized, with changed length and flexibility of the linkers to compare to known anthranilic diamide insecticides. In total, 26 novel compounds were synthesized, and all compounds were characterized by (1)H nuclear magnetic resonance and high-resolution mass spectrometry. Their insecticidal activities against oriental armyworm (Mythimna separata), mosquito larvae (Culex pipiens pallens), and diamondback moth (Plutella xylostella) were evaluated. The larvicidal activities against oriental armyworm indicated that the introduction of acylthiourea into some structures could retain their insecticidal activity; 8 of the 15 compounds (13a-13e, 14a-14e, and 15a-15e) exhibited 100% larvicidal activity at 10 mg/L. However, the introduction of acylurea decreased the insecticidal activity; only 3 of the 11 compounds (17a-17k) exhibited 100% larvicidal activity at 200 mg/L. The whole-cell patch-clamp technique indicated that compound 13b and chlorantraniliprole exhibited similar effects on the voltage-gated calcium channel. The calcium-imaging technique was also applied to investigate the effects of compounds 13b and 15a on the intracellular calcium ion concentration ([Ca(2+)](i)), which indicated that they released stored calcium ions from endoplasmic reticulum. Experimental results denoted that several new compounds are potential activators of the insect ryanodine receptor (RyR).

    Topics: Animals; Culex; Diamide; Drug Design; Insecticides; Larva; Moths; ortho-Aminobenzoates; Structure-Activity Relationship

2012