title: Design, synthesis, structure, and acaricidal/insecticidal activity of novel spirocyclic tetronic acid derivatives containing an oxalyl moiety.
abstract: A series of novel spirocyclic tetronic acid derivatives containing an oxalyl moiety was designed and synthesized via the key intermediate 3-(2,4,6-trimethyl)-2-oxo-1-oxaspiro[4.4]-decyl-3-en-4-ol. The target compounds were identified by (1)H NMR and elemental analysis or high-resolution mass spectrum (HRMS). The results of bioassays indicated that most of the target compounds possessed excellent acaricidal activities against carmine spider mite larvae and eggs. Especially, diisopropylamino oxalyl compound 7g and piperidine oxalyl compound 7h were 1.4- and 2.3-fold as high as the activities of commercial Spiromesifen, respectively, against spider mite eggs. Moreover, most of the target compounds exhibited insecticidal activities against Lepidoptera pest. Interestingly, compounds containing alkylamino-substituted oxalyl moiety showed obvious selectivity between spider mite larvae and eggs because the activities against spider mite eggs of 7g and 7h were 25-fold those against spider mite larvae, whereas Spiromesifen had no significant differences in these activities. This meant that the introduction of an oxalyl moiety to spirocyclic tetronic acid might lead to novel biological activity characteristics.
authors: State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China.
authors: Zhihui
authors: Z
authors: Liu
authors: Qiong
authors: Q
authors: Lei
authors: Yongqiang
authors: Y
authors: Li
authors: Lixia
authors: L
authors: Xiong
authors: Haibin
authors: H
authors: Song
authors: Qingmin
authors: Q
authors: Wang
mesh_terms: D056810:Acaricides / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D005663:Furans / Q000737:chemistry*; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry; D007814:Larva; D015394:Molecular Structure; D010070:Oxalates / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D040102:Tetranychidae
chemical_list: D056810:Acaricides; D005663:Furans; D007306:Insecticides; D010070:Oxalates; D013141:Spiro Compounds; C003422:tetronic acid