Synthesis and antifeeding activities of Tonghaosu analogues.
Tonghaosu (1), a lead for a botanical antifeedant, and its 22 analogues were synthesized according to a previously reported concise and straightforward procedure. The structures of all new compounds were confirmed by NMR, IR, MS, and HREIMS or elemental analysis. Their insect antifeedant activities against the large white butterfly (Pieris brassicae L.) were examined, and six analogues (Z- and E-6h and Z-isomers of 6i-l), which contain 1,3-diyn or 3,4-methylenedioxyphenyl acetylene group, showed considerable antifeedant activity. Interestingly, Z-isomers of 6i-k are much more active than their corresponding E-isomers.
Chen
Li
L
State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.
Xu
Han-Hong
HH
Yin
Biao-Lin
BL
Xiao
Chun
C
Hu
Tai-Shan
TS
Wu
Yu-Lin
YL
D000480:Alkynes / Q000032:analysis* / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D002080:Butterflies / Q000502:physiology*; D031202:Chrysanthemum / Q000737:chemistry; D004435:Eating / Q000187:drug effects*; D007306:Insecticides / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000032:analysis* / Q000737:chemistry / Q000494:pharmacology
D000480:Alkynes; D007306:Insecticides; D013141:Spiro Compounds; C493678:tonghaosu