Design, Synthesis and Biological Activities of Novel Anthranilic Diamide Insecticide Containing Trifluoroethyl Ether
Two series of novel anthranilic diamide insecticide containing trifluoroethyl ether were designed and synthesized, and their structures were characterized by 1H NMR spectroscopy, elemental analysis and single crystal X-ray diffraction analysis. The insecticidal activities of the new compounds were e...
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| Published in | Chinese journal of chemistry Vol. 30; no. 8; pp. 1748 - 1758 |
|---|---|
| Main Author | |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
01.08.2012
WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1001-604X 1614-7065 |
| DOI | 10.1002/cjoc.201200362 |
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| Abstract | Two series of novel anthranilic diamide insecticide containing trifluoroethyl ether were designed and synthesized, and their structures were characterized by 1H NMR spectroscopy, elemental analysis and single crystal X-ray diffraction analysis. The insecticidal activities of the new compounds were evaluated. The results of bioassays indicated that some of these title compounds exhibited excellent insecticidal activities. The insecticidal activities of compounds 19a, 19b, 19d, 19g, 19k and 19m against oriental armyworm at 2.5 mg·kg-1 were 100%. The larvicidal activities of 19a, 19b, 19c, 19d, 19e, 19g and 19n against diamond-back moth were 100% at 0.1 mg·kg-1. Surprisingly, most of them still exhibited perfect insecticidal activity against diamond-back moth when the concentration was reduced to 0.05 mg·kg-1, which was higher than the commercialized Chlorantraniliprole. |
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| AbstractList | Two series of novel anthranilic diamide insecticide containing trifluoroethyl ether were designed and synthesized, and their structures were characterized by 1H NMR spectroscopy, elemental analysis and single crystal X-ray diffraction analysis. The insecticidal activities of the new compounds were evaluated. The results of bioassays indicated that some of these title compounds exhibited excellent insecticidal activities. The insecticidal activities of compounds 19a, 19b, 19d, 19g, 19k and 19magainst oriental armyworm at 2.5 mg·kg-1 were 100%. The larvicidal activities of 19a, 19b, 19c, 19d, 19e, 19g and 19nagainst diamond-back moth were 100% at 0.1 mg·kg-1. Surprisingly, most of them still exhibited perfect insecticidal activity against diamond-back moth when the concentration was reduced to 0.05 mg·kg-1, which was higher than the commercialized Chlorantraniliprole. Two series of novel anthranilic diamide insecticide containing trifluoroethyl ether were designed and synthesized, and their structures were characterized by 1H NMR spectroscopy, elemental analysis and single crystal X‐ray diffraction analysis. The insecticidal activities of the new compounds were evaluated. The results of bioassays indicated that some of these title compounds exhibited excellent insecticidal activities. The insecticidal activities of compounds 19a, 19b, 19d, 19g, 19k and 19m against oriental armyworm at 2.5 mg·kg−1 were 100%. The larvicidal activities of 19a, 19b, 19c, 19d, 19e, 19g and 19n against diamond‐back moth were 100% at 0.1 mg·kg−1. Surprisingly, most of them still exhibited perfect insecticidal activity against diamond‐back moth when the concentration was reduced to 0.05 mg·kg−1, which was higher than the commercialized Chlorantraniliprole. Two series of novel anthranilic diamide insecticide containing trifluoroethyl ether were designed and synthesized. The insecticidal activities of the new compounds were evaluated. Surprisingly, most of them still exhibited perfect insecticidal activity against diamond‐back moth when the concentration was reduced to 0.05 mg·kg−1, which was higher than the commercialized Chlorantraniliprole. Two series of novel anthranilic diamide insecticide containing trifluoroethyl ether were designed and synthesized, and their structures were characterized by 1H NMR spectroscopy, elemental analysis and single crystal X-ray diffraction analysis. The insecticidal activities of the new compounds were evaluated. The results of bioassays indicated that some of these title compounds exhibited excellent insecticidal activities. The insecticidal activities of compounds 19a, 19b, 19d, 19g, 19k and 19m against oriental armyworm at 2.5 mg·kg-1 were 100%. The larvicidal activities of 19a, 19b, 19c, 19d, 19e, 19g and 19n against diamond-back moth were 100% at 0.1 mg·kg-1. Surprisingly, most of them still exhibited perfect insecticidal activity against diamond-back moth when the concentration was reduced to 0.05 mg·kg-1, which was higher than the commercialized Chlorantraniliprole. Two series of novel anthranilic diamide insecticide containing trifluoroethyl ether were designed and synthesized, and their structures were characterized by super(1)H NMR spectroscopy, elemental analysis and single crystal X-ray diffraction analysis. The insecticidal activities of the new compounds were evaluated. The results of bioassays indicated that some of these title compounds exhibited excellent insecticidal activities. The insecticidal activities of compounds 19a, 19b, 19d, 19g, 19k and 19m against oriental armyworm at 2.5 mg.kg super(-1) were 100%. The larvicidal activities of 19a, 19b, 19c, 19d, 19e, 19g and 19n against diamond-back moth were 100% at 0.1 mg.kg super(-1). Surprisingly, most of them still exhibited perfect insecticidal activity against diamond-back moth when the concentration was reduced to 0.05 mg.kg super(-1), which was higher than the commercialized Chlorantraniliprole. Two series of novel anthranilic diamide insecticide containing trifluoroethyl ether were designed and synthesized. The insecticidal activities of the new compounds were evaluated. Surprisingly, most of them still exhibited perfect insecticidal activity against diamond-back moth when the concentration was reduced to 0.05 mg.kg super(-1), which was higher than the commercialized Chlorantraniliprole. Two series of novel anthranilic diamide insecticide containing trifluoroethyl ether were designed and synthesized, and their structures were characterized by 1H NMR spectroscopy, elemental analysis and single crystal X-ray diffraction analysis. The insecticidal activities of the new compounds were evaluated. The results of bioassays indicated that some of these title compounds exhibited excellent insecticidal activities. The insecticidal activities of compounds 19a, 19b, 19d, 19g, 19k and 19m against oriental armyworm at 2.5 mg center dot kg-1 were 100%. The larvicidal activities of 19a, 19b, 19c, 19d, 19e, 19g and 19n against diamond-back moth were 100% at 0.1 mg center dot kg-1. Surprisingly, most of them still exhibited perfect insecticidal activity against diamond-back moth when the concentration was reduced to 0.05 mg center dot kg-1, which was higher than the commercialized Chlorantraniliprole. Two series of novel anthranilic diamide insecticide containing trifluoroethyl ether were designed and synthesized, and their structures were characterized by 1 H NMR spectroscopy, elemental analysis and single crystal X‐ray diffraction analysis. The insecticidal activities of the new compounds were evaluated. The results of bioassays indicated that some of these title compounds exhibited excellent insecticidal activities. The insecticidal activities of compounds 19a , 19b , 19d , 19g , 19k and 19m against oriental armyworm at 2.5 mg·kg −1 were 100%. The larvicidal activities of 19a , 19b , 19c , 19d , 19e , 19g and 19n against diamond‐back moth were 100% at 0.1 mg·kg −1 . Surprisingly, most of them still exhibited perfect insecticidal activity against diamond‐back moth when the concentration was reduced to 0.05 mg·kg −1 , which was higher than the commercialized Chlorantraniliprole. |
| Author | Wang, Hongxue Zhao, Yu Li, Yongqiang Xiong, Lixia Li, Zhengming |
| AuthorAffiliation | National Pesticidal Engineering Centre （ Tianjin）, State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China |
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| Copyright | Copyright © 2012 SIOC, CAS, Shanghai & WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim Copyright © 2012 SIOC, CAS, Shanghai & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim |
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| Keywords | trifluoroethyl ether N-PYRIDYLPYRAZOLE POTENT anthranilic diamide ryanodine receptor insecticidal activity |
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| Notes | 31-1547/O6 anthranilic diamide, ryanodine receptor, trifluoroethyl ether, insecticidal activity Two series of novel anthranilic diamide insecticide containing trifluoroethyl ether were designed and synthesized, and their structures were characterized by 1H NMR spectroscopy, elemental analysis and single crystal X-ray diffraction analysis. The insecticidal activities of the new compounds were evaluated. The results of bioassays indicated that some of these title compounds exhibited excellent insecticidal activities. The insecticidal activities of compounds 19a, 19b, 19d, 19g, 19k and 19m against oriental armyworm at 2.5 mg·kg-1 were 100%. The larvicidal activities of 19a, 19b, 19c, 19d, 19e, 19g and 19n against diamond-back moth were 100% at 0.1 mg·kg-1. Surprisingly, most of them still exhibited perfect insecticidal activity against diamond-back moth when the concentration was reduced to 0.05 mg·kg-1, which was higher than the commercialized Chlorantraniliprole. Zhao Yu, Li Yongqiang, Xiong Lixia, Wang Hongxue,Li Zhengming（National Pesticidal Engineering Centre （ Tianjin）, State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China） the National Basic Research Program of China - No. 2010CB126106 ark:/67375/WNG-33M0VHMD-K ArticleID:CJOC201200362 the Specialized Research Fund for the Doctoral Program of Higher Education - No. 20110031120011 the Fundamental Research Funds for the Central Universities istex:4C57F4B6BFEFCC314C7767D27595F88A429DACD0 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23 |
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| Snippet | Two series of novel anthranilic diamide insecticide containing trifluoroethyl ether were designed and synthesized, and their structures were characterized by... Two series of novel anthranilic diamide insecticide containing trifluoroethyl ether were designed and synthesized, and their structures were characterized by 1... |
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| SubjectTerms | anthranilic diamide Bioassays Chemistry Chemistry, Multidisciplinary insecticidal activity Insecticides Physical Sciences ryanodine receptor Science & Technology trifluoroethyl ether X-ray diffraction 三氟 乙基 二苯乙烯苷 合成 杀虫剂 生物活性 设计 邻氨基 |
| Title | Design, Synthesis and Biological Activities of Novel Anthranilic Diamide Insecticide Containing Trifluoroethyl Ether |
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