Design, Synthesis, and Insecticidal Activities of New N-Benzoyl-N′-phenyl-N′-sulfenylureas

Abstract

A series of new N'-alkylaminothio, N'-arylaminothio (or dithio), and N',N'-thio (or dithio) derivatives of N-benzoyl-N'-phenylureas were designed and synthesized as insect-growth regulators with sulfur dichloride or disulfur dichloride as the original reactant. The new compounds were identified by (1)H nuclear magnetic resonancee (NMR) spectroscopy, elemental analysis [or high-resolution mass spectrometry (HRMS)], and single-crystal X-ray diffraction analysis. The X-ray results demonstrated that there exist N-S-N or N-S-S-N bonds in these new compounds. In comparison to the parent N-benzoyl-N'-phenylureas, these derivatives displayed better solubility. The insecticidal activities of the target compounds were evaluated. The results of bioassays showed that compounds 1-24 retained the larvicidal activities of the corresponding benzoylphenylureas (BPUs) and some compounds exhibited better larvicidal activities against oriental armyworm and mosquitoes than the parent BPUs. The larvicidal activities of the selected target compounds 1 and 24 against diamondback moth were better than that of the corresponding parent compounds E and triflumuron.

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 .…”

Evaluation of etoxazole against insects and acari in vegetables in China

“…The mechanism of action of etoxazole (inhibition of the moulting process during insect and mite development) is similar to that of benzoylphenylureas ( Lee et al 2004 ; Nauen et al 2006 ; Asahara et al 2008 ; Sun et al 2008 ), a class of insecticides known to interfere with chitin biosynthesis. However, benzoylphenylureas as insect growth regulators have some shortcomings, such as a quite narrow spectrum of efficacy only on Lepidoptera and a high acute toxicity to nontarget insects ( Sun et al 2009 ).…”

Evaluation of Etoxazole against Insects and Acari in Vegetables in China

“…However, benzoylphenylureas as insect growth regulators have some shortcomings, such as a quite narrow spectrum of efficacy only on Lepidoptera and a high acute toxicity to nontarget insects ( Sun et al 2009 ). …”