Mono-substituted p-tert-butylthiacalix[4]arene: Regioselective Synthesis and Toxicological Activity Against Cowpea Aphid, Aphis craccivora (Koch)

Sharaf, Mohamed; Moustafa, Amr H.; Drar, Ali M.; Mohamed, Mounir A. A.; Omran, Omran A.

doi:10.21608/sjsci.2024.277800.1190

	Mono-substituted p-tert-butylthiacalix[4]arene: Regioselective Synthesis and Toxicological Activity Against Cowpea Aphid, Aphis craccivora (Koch)
Sohag Journal of Sciences
Volume 9, Issue 4, December 2024, Page 423-428 PDF (390.71 K)
Document Type: Regular Articles
DOI: 10.21608/sjsci.2024.277800.1190
View on SCiNiTO
Authors
Mohamed Sharaf ¹; Amr H. Moustafa¹^{, 2}; Ali M. Drar³; Mounir A. A. Mohamed¹; Omran A. Omran¹
¹Department of Chemistry, Faculty of Science, Sohag University, Sohag 82524, Egypt.
²Faculty of Science, King Salman International University, RasSudr 46612, Sinai, Egypt.
³Research Institute of Plant Protection, Agricultural Research Center, Giza 12112, Egypt.
Abstract
Tetraethylamonium bromide (TEAB) in dry benzene has been utilized as the base enabling Phase Transfer Catalysis PTC for the synthesis of some novel mono-substituted thiacalix[4]arene 2 and 3 at the lower rim from 2-chloro(p-tolyl)acetamide and 2-chloro(p-acetylphenyl)acetamide, respectively. Bromine and mono-p-acetylphenylacetamide-p-tert-butylthiacalix[4]arene 3 were reacted in chloroform under solar radiation to give mono-p-phenacylbromideacetamide-p-tert-butylthiacalix[4]arene 4. Derivatives of mono-substituted thiacalix[4]arenes 2-4 were reacted with Lawesson reagent (LR) affording mono-substituted thiacalix[4]arene derivatives 5-7, respectively. The temple of the novel compounds was illustrated based on elemental analyses, ¹H-, ¹³C-, and Dept-NMR spectroscopy. Synthesized derivatives have been tested against adult and nymph Cowpea Aphid (Aphis craccivora) in laboratory conditions as insecticidal agents. to calculate the LC₅₀ values for each one of them. Bioassay experiments showed that synthesized compounds 4 and 7 possess the highest insecticidal bio-efficacy, with LC₅₀values of 1.16 and 2.08 ppm, respectively against nymphs, and 11.96 and 13.52 ppm, respectively, against adults of Aphis craccivora.
Keywords
Thiacalix[4]arene; Tetraethylamonium bromide; Lawesson reagent; Aphis craccivora; Eco-friendly insecticides


Statistics Article View: 174 PDF Download: 127