Synthesis and insecticidal activity of benzoheterocyclic analogues of N′‐benzoyl‐N‐(tert‐butyl)benzohydrazide: Part 1. Design of benzoheterocyclic analogues

Abstract

The N'-benzoyl group of N-tert-butyl-N'-benzoyl-3,5-dimethylbenzohydrazide (1) was converted to a series of benzoheterocyclecarbonyl groups in order to investigate the potential usefulness of superimposing a hydrazine insecticide on 20-hydroxyecdysone. A series of analogues with benzodioxole, benzodioxane, benzodioxapine, indole, benzoxazole, benzoxazine or benzothiazole instead of the phenyl group of (1) were synthesized and tested for their insecticidal activity against the common cutworm (Spodoptera litura F). N-tert-Butyl-N'-(3,5-dimethylbenzoyl)-1,3-benzodioxole-5-carbohydrazide and N-tert-butyl-N'-(3,5-dimethylbenzoyl)-2,3-dihydro-1,4-benzodioxine-6-carbohydrazide showed high insecticidal activities, superior to that of (1) and equal to that of the commercial insecticide tebufenozide (RH-5992).

Synthesis and insecticidal activity of benzoheterocyclic analogues of N′‐benzoyl‐N‐(tert‐butyl)benzohydrazide: Part 2. Introduction of substituents on the benzene rings of the benzoheterocycle moiety

“…5‐Methyl‐2,3‐dihydro‐1,4‐benzodioxine‐6‐carbonyl chloride, obtained by reacting the corresponding benzoic acid Ib 8 (970 mg, 5 mmol) with thionyl chloride (2 ml), was dissolved in dichloromethane (2 ml). The solution was added dropwise to a stirred mixture of V 6 (1.1 g, 5 mmol), triethylamine (610 mg, 6 mmol) and dichloromethane (5 ml) in an ice bath. After stirring the mixture at room temperature for 3 h, ethyl acetate (100 ml) was added to the reaction mixture.…”

“…In the first of this series of three papers,6 we reported the structure–activity relationships of a series of N ′‐benzoheterocyclecarbonyl‐ N ‐ tert ‐butyl‐3,5‐dimethylbenzohydrazides. The most active analogue among them, N ′‐ tert ‐butyl‐ N ′‐(3,5‐dimethylbenzoyl)‐1,3‐benzodioxole‐5‐carbohydrazide ( 1 ) and N ′‐ tert ‐butyl‐ N ′‐(3,5‐dimethylbenzoyl)‐2,3‐dihydro‐1,4‐benzodioxine‐6‐carbohydrazide ( 3 ), exerted insecticidal activity against common cutworm ( Spodoptera litura L) larvae almost equal to that of tebufenozide 6…”

Synthesis of 3,4,5-trihydroxybenzohydrazone and evaluation of their urease inhibition potential

“…Benzohydrazones having heterocyclic rings were reported to have antiglycation, anticonvulsant, Phosphodiesterase-1 inhibitors, antiproliferative, antifungal and anti-HIV activities (Kabak et al, 1999;Ku¨c¸u¨kgu¨zel et al, 2004;Khan et al, 2014a;Jamil et al, 2015;Pandeya et al, 1999). Several benzohydrazones reported interesting bioactivities, such as antifungal, anticonvulsant, anti-inflammatory, antibacterial, antimalarial, antiplatelets, analgesic, antituberculosis, antioxidant (Loncle et al, 2004;Ku¨c¸u¨kgu¨zel et al, 2003;Todeschini et al, 1998;Melnyk et al, 2006;Lima et al, 2000;Cunha et al, 2003;Kaymakc¸ıog˘lu et al, 2006;Aziz et al, 2014), antileishmanial, insecticidal, immunoconjugates, antimycobacterial, adriamycin proteinase inhibition and activity against protozoan parasite (Sawada et al, 2003;Taha et al, 2013;Ku¨c¸u¨kgu¨zel and Rollas, 2002;Greenfield et al, 1990;Caffery et al, 2002). Other benzohydrazone derivatives have reported b-glucuronidase ) and aglucosidase inhibition activity .…”

Exploration of the binding affinities between ecdysone agonists and EcR/USP by docking and MM-PB/GBSA approaches

“…1), which was the first nonsteroidal ecdysone agonist of EcR to be discovered [4]. Surprisingly, neither RH-5849 nor any other commercialized DBHs, such as halofenozide (1c), tebufenozide (1f), methoxyfenozide (1g), and chromafenozide (1i), are structurally similar to the natural substrate 20E [5][6][7][8]. DBHs overcome the above-mentioned disadvantage of 20E as they have favorable physicochemical properties.…”