Synthesis and Insecticidal Activity of N-tert-Butyl-N,N′-diacylhydrazines Containing 1,2,3-Thiadiazoles

Abstract

N-tert-Butyl-N,N'-diacylhydrazines are nonsteroidal ecdysone agonists used as environmental benign pest regulators. In this paper, two series of new N-tert-butyl-N,N'-diacylhydrazine derivatives containing 1,2,3-thiadiazole were designed and synthesized. All structures of the synthesized compounds were confirmed by proton nuclear magnetic resonance ((1)H NMR), infrared spectroscopy (IR), and high-resolution mass spectrometry (HRMS). Bioasssay results indicated that most of the synthesized compounds possessed good insecticidal activities against Plutella xylostella L. and Culex pipiens pallens as compared with the positive control, tebufenozide. The results of this study indicated that 1,2,3-thiadiazoles, as an important active substructure, could improve or maintain the activity of the dicylhydrazines and favor novel pesticide development.

Synthesis, Crystal Structure, and Fungicidal Activity of a Novel 1,2,3-Thiadiazole Compound

“…For example, many 1,2,3-thiadiazoles exhibited plant inducer activity, 11 anti-HBV activity, 12 fungicidal activity, 13 and insecticidal activity. 14 1,2,3-Thiadiazoles as examples of pesticide precursors have become one of the area of focus of developing agrochemicals in academia and industry. The piperidine ring also exhibited excellent biological properties, such as antifungal, 15 antimalarial 16 and antileukemic activities, 17 GABA inhibitors, 18 VLA-4 inhibitors, 19 and herbicidal activity.…”

Turning renewable resources into value-added products: Development of rosin-based insecticide candidates

“…1. Meanwhile, thiadiazole heterocyclic group has been documented to show a wide range of bioactivities, for instance, insecticidal, antimicrobic, antifungal, antineoplastic, herbicidal, etc (Gomha et al, 2015;Lin et al, 2014;Popiołek et al, 2015;Sobhy et al, 2012;Suzuki et al, 2011;Wang et al, 2011). Enlightened by all of the descriptions above, 37 rosin-based amide derivatives containing thiadiazole group were synthesized.…”

Synthesis and Characterization of Various Alkyl, Aryl and Hetero Aryl Substituted Hydrazines and Study of their Biological Activity

“…Diacylhydrazines have been identified as one of the most important types of insect regulators [11][12][13] . Several commercial compounds, s u c h a s t e bu fe n o z i d e, m e t h ox y fe n o z i d e, chromafenozide,and halofenozide, are all classified as diacylhydrazines, and all of these insecticides 14,15 .…”

“…Several commercial compounds, s u c h a s t e bu fe n o z i d e, m e t h ox y fe n o z i d e, chromafenozide,and halofenozide, are all classified as diacylhydrazines, and all of these insecticides 14,15 . Diacylhydrazines have attracted significant attention because of their high insecticidal selectivity,simple structure, and low toxicity to vertebrates 13 .…”