Chinese Journal of Organic Chemistry >
Synthesis and Insecticidal Activity of Novel Anthranilic Diamides Containing Polyfluoroalkyl Pyrazole Moiety
Received date: 2017-01-09
Revised date: 2017-04-08
Online published: 2017-04-21
Supported by
Project supported by the National Key Technologies R&D Program of China during the 12th Five-Year Plan Period (No. 2011BAE06B01-20).
A series of novel anthranilic diamides containing polyfluoroalkyl pyrazole were synthesized using 2,3-dichloropyridine and hydrazine hydrate as starting materials via substitution, condensation, oxidation, etherification, cyclization and ring cleavage reaction. The title products were characterized by 1H NMR and HRMS. The bioassay results indicated that most of title compounds exhibited 100% insecticidal activitiy against Mythimna separata Walker at 0.8 mg/L, N-(4-chloro-2-(isopropylcarbamoyl)-6-methylphenyl)-1-(3-chloropyridin-2-yl)-3-((1-methyl-3-(perfluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl)oxy)-1H-pyrazole-5-carboxamide (8c) and N-(4-chloro-2-(cyclopropylcarbamoyl)-6-methylphenyl)-1-(3-chloropyridin-2-yl)-3-((1-methyl-3-(perfluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl)oxy)-1H-pyrazole-5-carboxamide (8d) showed more than 60% larvicidal activity against Prodenia litura Fabricius at 2 mg/L, and the mortality of N-(4-chloro-2-(dimethylcarbamoyl)-6-methylphenyl)-1-(3-chloropyridin-2-yl)-3-((1-methyl-3-(perfluoroethyl)-4-(trifluoromethyl)-1Hpyrazol-5-yl)oxy)-1H-pyrazole-5-carboxamide (8l) against Plutella xylostella Linnaeus reached 82.5% at 0.08 mg/L.
Shi Jianjun , Ren Guihua , Wu Ningjie , Liu Xinghai , Xu Tianming , Tan Chengxia . Synthesis and Insecticidal Activity of Novel Anthranilic Diamides Containing Polyfluoroalkyl Pyrazole Moiety[J]. Chinese Journal of Organic Chemistry, 2017 , 37(8) : 2131 -2138 . DOI: 10.6023/cjoc201701019
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