title: 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.
authors.affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Development Center for Fine Chemicals, Guizhou University, Guiyang 550025, China.
authors.forename: Shenghong
authors.initials: S
authors.lastname: Kang
authors.forename: Baoan
authors.initials: B
authors.lastname: Song
authors.forename: Jian
authors.initials: J
authors.lastname: Wu
authors.forename: Ming
authors.initials: M
authors.lastname: He
authors.forename: Deyu
authors.initials: D
authors.lastname: Hu
authors.forename: Linhong
authors.initials: L
authors.lastname: Jin
authors.forename: Song
authors.initials: S
authors.lastname: Zeng
authors.forename: Wei
authors.initials: W
authors.lastname: Xue
authors.forename: Song
authors.initials: S
authors.lastname: Yang
mesh_terms: D000081:Acetamides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D009036:Moths / Q000187:drug effects*; D011720:Pyrazoles / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D000081:Acetamides; D007306:Insecticides; D011720:Pyrazoles
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