Synthesis and insecticidal evaluation of N-tert-butyl-N'-thio[1-(6-chloro-3-pyridylmethyl)-2-nitroiminoimidazolidine]-N,N'-diacylhydrazines.
A series of novel N-tert-butyl-N'-thio[1-(6-chloro-3-pyridylmethyl)-2-nitroiminoimidazolidine]-N,N'-diacylhydrazines were synthesized by the reaction of chlorosulfenyl(N-tert-butyl-N,N'-diacylhydrazines) with 1-(6-chloro-3-pyridylmethyl)-2-nitroiminoimidazolidine (imidacloprid) in the presence of sodium hydride. Their larvicidal activities were evaluated. All of them exhibited insecticidal activities against Oriental armyworm and bean aphids. Toxicity assays indicated that at higher concentrations (200 mg L(-1)) the title compounds can kill aphids as fast as the parent imidacloprid in 2 h, whereas at lower concentration (10 mg L(-1)), the title compounds can induce a premature, abnormal and lethal larval moult after 3 days of treatment, like the parent diacylhydrazines.
Shang
Jian
J
Chemistry and Biologic College, Yantai University, Yantai 264005, Shandong Province, People's Republic of China. shangjian.@126.com
Sun
Ranfen
R
Li
Yongqiang
Y
Huang
Runqiu
R
Bi
Fuchun
F
Wang
Qingmin
Q
D000818:Animals; D001042:Aphids / Q000187:drug effects; D006834:Hydrazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D007814:Larva / Q000187:drug effects; D015394:Molecular Structure; D009036:Moths / Q000187:drug effects; D013329:Structure-Activity Relationship
D006834:Hydrazines; D007306:Insecticides; C029424:hydrazine