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)

Document Type : Regular Articles

Authors

¹ Department of Chemistry, Faculty of Science, Sohag University, Sohag 82524, Egypt.

² Faculty of Science, King Salman International University, RasSudr 46612, Sinai, Egypt.

³ Research Institute of Plant Protection, Agricultural Research Center, Giza 12112, Egypt.

10.21608/sjsci.2024.277800.1190

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.

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