Design, synthesis and insecticidal activities of novel acetamido derivatives containing N-pyridylpyrazole carboxamides

Abstract

A series of novel acetamido derivatives containing N-pyridylpyrazole carboxamides was designed and synthesized by increasing the amide bridge of chlorantraniliprole using acetamido moieties and introducing different aryl substitutions. The target compounds were characterized by (1)H NMR, (13)C NMR, IR, and elemental analysis. Bioassays indicated that some of the synthesized compounds exhibited strong insecticidal activity against Plutella xylostella. Compounds 5e, 5g and 5v were the most potent, with LC50 values of 23.72, 2.04, and 20.01 mg/L, respectively. The insecticidal activity of compound 5g was higher than that of chlorpyrifos (LC50 = 7.25 mg/L), a commonly used insecticide. These results indicate that novel acetamido derivatives containing N-pyridylpyrazole carboxamides can effectively control P. xylostella.

Keywords: (1)H NMR; (13)C NMR; ADGUQHZGKCFXFF-UHFFFAOYSA-N; AXTBANQNGCQWIH-UHFFFAOYSA-N; Acetamido derivatives; BGRHXOCUOGKOFF-UHFFFAOYSA-N; CCAIWWICQJIRNT-UHFFFAOYSA-N; FVDHIDBTYNAYHU-UHFFFAOYSA-N; HKMJJZJSINSUJI-UHFFFAOYSA-N; HODOGMBBFHOUOU-UHFFFAOYSA-N; HWFBXXMWALNJFJ-UHFFFAOYSA-N; IR; Insecticidal activity; JUCFHZIFBCHESQ-UHFFFAOYSA-N; KBIDVIJRCFEWPJ-UHFFFAOYSA-N; LC(50); LHDALURNYHPVBP-UHFFFAOYSA-N; MESJBVRMCYELSC-UHFFFAOYSA-N; N-pyridylpyrazole carboxamides; P. xylostella; PZPPOKUDKNZEPN-UHFFFAOYSA-N; Plutella xylostella; QIGAGLVKQMVUIW-UHFFFAOYSA-N; RUYMOGKRZCUDBX-UHFFFAOYSA-N; SAR; SMDGKMMSFKFABF-UHFFFAOYSA-N; Synthesis; UUQTUDLAQCJRLR-UHFFFAOYSA-N; WAQJLNODBHIJBL-UHFFFAOYSA-N; WFPFPTZXYSLGKU-UHFFFAOYSA-N; WNIMVUTWILZLSB-UHFFFAOYSA-N; WSFNQGLZXUQPCR-UHFFFAOYSA-N; YUTGLCZQUUBWPD-UHFFFAOYSA-N; ZGBYCDKJPMXJQG-UHFFFAOYSA-N; carbon nuclear magnetic resonance; infrared; median lethal concentration; melting point; mp; proton nuclear magnetic resonance; structure–activity relationship.