Selective toxicity of N-sulfenylated derivatives of insecticidal methylcarbamate esters

Allan L. Black; Yu-Chang Chiu; Mohamed A. H. Fahmy; T. Roy Fukuto

doi:10.1021/jf60189a001

Selective toxicity of N-sulfenylated derivatives of insecticidal methylcarbamate esters

Journal of Agricultural and Food Chemistry ◽

10.1021/jf60189a001 ◽

1973 ◽

Vol 21 (5) ◽

pp. 747-751 ◽

Cited By ~ 29

Author(s):

Allan L. Black ◽

Yu-Chang Chiu ◽

Mohamed A. H. Fahmy ◽

T. Roy Fukuto

Keyword(s):

Selective Toxicity ◽

Derivatives Of

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ChemInform Abstract: SELECTIVE TOXICITY OF N-SULFENYLATED DERIVATIVES OF INSECTICIDAL METHYLCARBAMATE ESTERS

Chemischer Informationsdienst ◽

10.1002/chin.197403252 ◽

1974 ◽

Vol 5 (3) ◽

pp. no-no

Author(s):

A. L. BLACK ◽

Y. C. CHIU ◽

M. A. H. FAHMY ◽

T. R. FUKUTO

Keyword(s):

Selective Toxicity ◽

Derivatives Of

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Ionic Liquids Enhanced Alkynyl Schiff Bases Derivatives of Fipronil Synthesis and Their Cytotoxicity Studies

Molecules ◽

10.3390/molecules24183223 ◽

2019 ◽

Vol 24 (18) ◽

pp. 3223 ◽

Cited By ~ 1

Author(s):

Liu ◽

Huang ◽

Chen ◽

Li ◽

Yan ◽

...

Keyword(s):

Nuclear Magnetic Resonance ◽

Ionic Liquids ◽

Magnetic Resonance ◽

Schiff Bases ◽

Resonance Spectroscopy ◽

Selective Toxicity ◽

Toxic Activity ◽

Cytotoxicity Studies ◽

Derivatives Of ◽

Nuclear Magnetic

To obtain highly selective toxic derivatives of fipronil, a series of Schiff bases with an alkynyl group (3a–3k) were designed and synthesized from 4-ethynylbenzaldehyde (2) and 4-substituted 5-amino-N-arylpyrazole (1a–1k) via a nucleophilic addition elimination reaction in ionic liquids. Utilization of ionic liquids was demonstrated to endow the yield of each compound beyond 50%, which was enhanced over 1.5 times of the synthetic productive rates comparing the conventional method by which longer reactive time was consumed. The derivatives were characterized via nuclear magnetic resonance hydrogen spectroscopy (1H-NMR), carbon-13 nuclear magnetic resonance spectroscopy (13C-NMR), and electrospray ionization high resolution mass spectrometry (ESI-HRMS). The cytotoxicity of these derivatives on Trichoplusia ni (Hi-5) cell and Spodoptera litura cell (SL cell) was evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) bioassays. The results indicated that several compounds had potential cytotoxicity on Hi-5 cell, especially a 4-ethyl substituted alkynyl Schiff base derivative (3f) that was demonstrated to possess high selective toxicity to the Hi-5 cell than the SL cell. In addition, 3f exhibited comparable toxic activity to commercial fipronil on a Hi-5 cell while a little toxic effect on the SL cell, which satisfied the expectation for selective toxicity screening.

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