Chinese Journal of Organic Chemistry >
Synthesis and Biological Activities of Novel 8-((3,4,4-Trifluorobut-3-en-1-yl)thio)-substituted Methylxanthines and Their Derivatives
Received date: 2020-12-01
Revised date: 2020-12-31
Online published: 2021-02-22
Supported by
National Natural Science Foundation of China(21772103); National Natural Science Foundation of China(22077070)
Using 8-chlorotheophylline and 4-bromo-1,1,2-trifluorobut-1-ene as materials, a series of novel 8-((3,4,4-tri- fluorobut-3-en-1-yl)thio)-substituted methylxanthines and their derivatives were successfully synthesized through nucleophilic substitution, protection, deprotection, and oxidation. The structures of the title compounds were confirmed and characterized by melting point, 1H NMR, 13C NMR, 19F NMR and HRMS. Their preliminary bioassay results showed that most of the compounds in this series have good insecticidal activity. Among them, 1,3,7-trimethyl-8-((3,4,4-trifluorobut-3-en-1-yl)thio)- 3,7-dihydro-1H-purine-2,6-dione (5a), 7-isobutyl-1,3-dimethyl-8-((3,4,4-trifluorobut-3-en-1-yl)thio)-3,7-dihydro-1H-purine- 2,6-dione (5c) and 7-isobutyl-1,3-dimethyl-8-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)-3,7-dihydro-1H-purine-2,6-dione (5h) had 70% lethality rate against Mythimna separata Walker at a concentration of 200 mg?L–1. 5a, 5c and 1,3,7-trimethyl- 8-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)-3,7-dihydro-1H-purine-2,6-dione (5f) exhibited lethality rates of 72%, 80% and 65% against Plutella xylostellaL. at a concentration of 10 mg?L–1, respectively. Some of the compounds also showed certain fungicidal activity at 50 mg?L–1, among which 7-(cyclopropylmethyl)-1,3-dimethyl-8-((3,4,4-trifluorobut-3-en-1-yl)thio)-3,7- dihydro-1H-purine-2,6-dione (5b) possessed inhibition rates of 66.7% and 61.1% against Phytophthora capsici and Botrytis cinerea, respectively. 5c held a 55.6% inhibition rate towards Botrytis cinerea. This type of compounds provides new lead structures for the further research and development of novel insecticides.
Hang Liu , Shuyun Zhang , Huan Li , Yan Zhang , Zhengming Li , Baolei Wang . Synthesis and Biological Activities of Novel 8-((3,4,4-Trifluorobut-3-en-1-yl)thio)-substituted Methylxanthines and Their Derivatives[J]. Chinese Journal of Organic Chemistry, 2021 , 41(5) : 2091 -2098 . DOI: 10.6023/cjoc202012006
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