Jun Xu, Tianjiao Yang, Jiayi Wang
Jan 1, 2021
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Journal
Chemistry of Heterocyclic Compounds
Abstract
Novel 2-(8-azabicyclo[3.2.1]octan-3-yl)-3-imino-2,3-dihydro-1 H -isoindol-1-ones derived from 5-HT3 receptor antagonists hexahydroazepinylbenzamides were designed and synthesized through isocyanide insertion reaction. All target compounds were evaluated against pinewood nematodes B. xylophilus and root-knot nematodes M . incognita. Good lethal rate (75%) for 3-( tert -butylimino)-5-chloro-2-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-2,3-dihydro-1 H -isoindol-1-one and serious nervous curl effect against pinewood nematodes B. xylophilus for 3-( tert -butylimino)-2-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-2,3-dihydro-1 H -isoindol-1-one were observed at 10 mg/l. The inhibition activities of 3-[(4-methoxyphenyl)imino]-2-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-2,3-dihydro-1 H -isoindol-1-one against root-knot nematodes M . incognita were 84% at 160 mg/l and 60% at 20 mg/l for in vitro test and test tube test, respectively .