10.1021/acs.jafc.5b02036.s001
Rong Wang
Rong
Wang
Xiaoyan Zhi
Xiaoyan
Zhi
Jie Li
Jie
Li
Hui Xu
Hui
Xu
Synthesis of Novel Oxime Sulfonate Derivatives of 2′(2′,6′)-(Di)chloropicropodophyllotoxins
as Insecticidal Agents
American Chemical Society
2015
podophyllotoxin
compounds 4 c
chlorine
compound 5 f
introduction
oxime sulfonate derivatives
insecticidal activity
Novel Oxime Sulfonate Derivatives
NMR
picropodophyllotoxin
Di
HRMS
2015-08-05 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Synthesis_of_Novel_Oxime_Sulfonate_Derivatives_of_2_2_6_Di_chloropicropodophyllotoxins_as_Insecticidal_Agents/2144434
To
discover novel natural-product-based pesticidal agents, we prepared
a series of oxime sulfonate derivatives of 2′(2′,6′)-(Di)chloropicropodophyllotoxins
by structural modification of podophyllotoxin. Their structures were
well-characterized by proton nuclear magnetic resonance (<sup>1</sup>H NMR), high-resolution mass spectrometry (HRMS), optical rotation,
and melting point. Moreover, the key steric structure of compound <b>5f</b> was unambiguously determined by single-crystal X-ray diffraction.
Additionally, their insecticidal activity was evaluated at 1 mg/mL
against the pre-third-instar larvae of oriental armyworm (Mythimna separata Walker), a typical lepidopteran
pest. Among all derivatives, compounds <b>4c</b>, <b>5c</b>, and <b>5d</b> exhibited more promising insecticidal activity,
with the final mortality rates greater than 60%, when compared to
their precursor podophyllotoxin and the positive control, toosendanin.
It demonstrated that introduction of the chlorine atom at the C-2′
or C-2′,6′ position on the E ring of picropodophyllotoxin
or oxime sulfonate derivatives of picropodophyllotoxin was important
for the insecticidal activity and introduction of a halogen (e.g.,
fluorine, chlorine, or bromine) atom-substituted phenylsulfonyl group
on the oxime fragment of 2′(2′,6′)-(di)chloropicropodophyllones
could lead to more promising compounds.