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

Abstract

A series of N'-benzoheterocyclecarbonyl-N-tert-butyl-3,5-dimethylbenzohydrazide analogues possessing a variety of substituents on the benzene rings of the benzoheterocyle moieties were synthesized and tested for their insecticidal activity. The introduction of a methyl group at the R1 position of the benzoheterocycle moiety strongly increased the insecticidal activity. Among the analogues synthesized, N'-tert-butyl-N'-(3,5-dimethylbenzoyl)-5-methyl-6-chromanecarbohydrazide showed the highest insecticidal activity (LC50 = 0.89 mg litre(-1)).

Multidimensional Quantitative Structure–Activity Relationships of Diacylhydrazine Toxicity to Lepidopteran and Coleopteran Insect Pests

“…The disposition of a steric-enhancing CoMFA contour for BAW and a negative charge-enhacing contour for RSB near the B-ring is also consistent with the high Lepidopteran potency found for chromafenozide (ANS-118), a newer ecdysteroid agonist which possesses a B-fused chroman ring in the RSB negative charge-enhancing region. These contours are absent for CPB, for which chromafenozide shows only a low toxicity [5].…”

Cell-Based Screening Systems for Insecticides

“…Commercial DAH compounds, i.e. RH-2485 or methoxyfenozide, RH-0345 or halofenozide, and RH-5992 or tebufenozide from Rohm & Haas Co, Spring House, PA; now Dow AgroSciences, Indianapolis, IN; and ANS-118 or chromafenozide from Sankyo Agro Co. Ltd (presently Mitsui Agro Inc., Japan) and Nippon-Kayaku Co. Ltd (both Tokyo, Japan) Sawada et al 2003 ) , are mainly used to control lepidopteran pests although halofenozide formulations also exist against soil-dwelling coleopterans (Dhadialla et al , 2005 . Other non-steroidal analogs include AAKs (which resemble much DAHs; Tice et al 2003a, b ) and THQs (Smith et al 2003 ;Palli et al 2005b ) (Fig.…”

“…Screens have focused on the isolation of non-steroidal analogs that are suf fi ciently apolar to penetrate the insect's cuticle, are relatively resistant to metabolic enzymes and display high af fi nity for the ecdysone receptor complex. The group of chemicals that has been investigated mostly and for which commercial compounds were isolated are DAHs (Dhadialla et al , 2005Sawada et al 2003 ) . Commercial DAH compounds, i.e.…”

Synthesis and insecticidal activity of benzoheterocyclic analogues of N′‐benzoyl‐N‐(tert‐butyl)benzohydrazide: Part 3. Modification of N‐tert‐butylhydrazine moiety

“…In previous papers1, 2 we reported the synthesis and insecticidal activity of N ′‐benzoheterocyclecarbonyl‐ N‐tert ‐butyl‐3,5‐dimethylbenzohydrazide analogues. Among them, N ′‐ tert ‐butyl‐ N ′‐(3,5‐dimethylbenzoyl)‐5‐methyl‐2,3‐dihydro‐1,4‐benzodioxine‐6‐carbohydrazide ( 1 ) and N ′‐ tert ‐butyl‐ N ′‐(3,5‐dimethylbenzoyl)‐5‐methylchromane‐6‐carbohydrazide ( 2 , chromafenozide) showed the highest insecticidal activity (Fig 1).…”

“…Among them, N ′‐ tert ‐butyl‐ N ′‐(3,5‐dimethylbenzoyl)‐5‐methyl‐2,3‐dihydro‐1,4‐benzodioxine‐6‐carbohydrazide ( 1 ) and N ′‐ tert ‐butyl‐ N ′‐(3,5‐dimethylbenzoyl)‐5‐methylchromane‐6‐carbohydrazide ( 2 , chromafenozide) showed the highest insecticidal activity (Fig 1). 1, 2…”