Synthesis, Physicochemical Properties, and Biological Activities of 4-(<i>S</i>-Methyl-<i>N</i>-(2,2,2-Trifluoroacetyl)Sulfilimidoyl) Anthranilic Diamide
Novel anthranilic diamides with sulfilimidoyl and sulfoximidoyl functionalities were successfully prepared. Among newly-prepared organosulfur compounds, 3-bromo-1-(3-chloropyridin-2-yl)-<i>N</i>-(2-methyl-6-(methylcarbamoyl)-4-(methylthio)phenyl)-1<i>H</i>-pyrazole-5-carboxam...
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| Format: | Article |
| Language: | English |
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MDPI AG
2019-09-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/19/3451 |
| _version_ | 1818578780835282944 |
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| author | Hwan Jung Lim Won Hyung Lee Seong Jun Park |
| author_facet | Hwan Jung Lim Won Hyung Lee Seong Jun Park |
| author_sort | Hwan Jung Lim |
| collection | DOAJ |
| description | Novel anthranilic diamides with sulfilimidoyl and sulfoximidoyl functionalities were successfully prepared. Among newly-prepared organosulfur compounds, 3-bromo-1-(3-chloropyridin-2-yl)-<i>N</i>-(2-methyl-6-(methylcarbamoyl)-4-(methylthio)phenyl)-1<i>H</i>-pyrazole-5-carboxamide and (<i>S</i>,<i>E</i>)-3-bromo-1-(3-chloropyridin-2-yl)-<i>N</i>-(2-methyl-4-(S-methyl-<i>N</i>-(2,2,2-trifluoroacetyl)sulfinimidoyl)-6-(methylcarbamoyl)phenyl)-1<i>H</i>-pyrazole-5-carboxamide showed good levels of efficacy and a strong correlation between insecticidal activities and physical properties, respectively. In particular, available data indicated that the <i>N</i>-trifluoroacetyl sulfilimine moiety could be an appealing structural scaffold for the discovery of a new crop-protecting agent. |
| first_indexed | 2024-12-16T06:51:15Z |
| format | Article |
| id | doaj.art-0a248aded18f4faf87465eef5feda9ba |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-16T06:51:15Z |
| publishDate | 2019-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-0a248aded18f4faf87465eef5feda9ba2022-12-21T22:40:24ZengMDPI AGMolecules1420-30492019-09-012419345110.3390/molecules24193451molecules24193451Synthesis, Physicochemical Properties, and Biological Activities of 4-(<i>S</i>-Methyl-<i>N</i>-(2,2,2-Trifluoroacetyl)Sulfilimidoyl) Anthranilic DiamideHwan Jung Lim0Won Hyung Lee1Seong Jun Park2Bio & Drug Discovery Division, Korea Research Institute of Chemical Technology (KRICT), 141 Gajeong-ro, Yuseong-gu, Daejeon 34114, KoreaCentral Research Institute, Kyung Nong Co. Ltd., 34-14 Summeori-gil, Kyongju 38175, Kyongsangbuk-do, KoreaBio & Drug Discovery Division, Korea Research Institute of Chemical Technology (KRICT), 141 Gajeong-ro, Yuseong-gu, Daejeon 34114, KoreaNovel anthranilic diamides with sulfilimidoyl and sulfoximidoyl functionalities were successfully prepared. Among newly-prepared organosulfur compounds, 3-bromo-1-(3-chloropyridin-2-yl)-<i>N</i>-(2-methyl-6-(methylcarbamoyl)-4-(methylthio)phenyl)-1<i>H</i>-pyrazole-5-carboxamide and (<i>S</i>,<i>E</i>)-3-bromo-1-(3-chloropyridin-2-yl)-<i>N</i>-(2-methyl-4-(S-methyl-<i>N</i>-(2,2,2-trifluoroacetyl)sulfinimidoyl)-6-(methylcarbamoyl)phenyl)-1<i>H</i>-pyrazole-5-carboxamide showed good levels of efficacy and a strong correlation between insecticidal activities and physical properties, respectively. In particular, available data indicated that the <i>N</i>-trifluoroacetyl sulfilimine moiety could be an appealing structural scaffold for the discovery of a new crop-protecting agent.https://www.mdpi.com/1420-3049/24/19/3451anthranilic diamidesulfiliminesulfoximineinsecticide |
| spellingShingle | Hwan Jung Lim Won Hyung Lee Seong Jun Park Synthesis, Physicochemical Properties, and Biological Activities of 4-(<i>S</i>-Methyl-<i>N</i>-(2,2,2-Trifluoroacetyl)Sulfilimidoyl) Anthranilic Diamide Molecules anthranilic diamide sulfilimine sulfoximine insecticide |
| title | Synthesis, Physicochemical Properties, and Biological Activities of 4-(<i>S</i>-Methyl-<i>N</i>-(2,2,2-Trifluoroacetyl)Sulfilimidoyl) Anthranilic Diamide |
| title_full | Synthesis, Physicochemical Properties, and Biological Activities of 4-(<i>S</i>-Methyl-<i>N</i>-(2,2,2-Trifluoroacetyl)Sulfilimidoyl) Anthranilic Diamide |
| title_fullStr | Synthesis, Physicochemical Properties, and Biological Activities of 4-(<i>S</i>-Methyl-<i>N</i>-(2,2,2-Trifluoroacetyl)Sulfilimidoyl) Anthranilic Diamide |
| title_full_unstemmed | Synthesis, Physicochemical Properties, and Biological Activities of 4-(<i>S</i>-Methyl-<i>N</i>-(2,2,2-Trifluoroacetyl)Sulfilimidoyl) Anthranilic Diamide |
| title_short | Synthesis, Physicochemical Properties, and Biological Activities of 4-(<i>S</i>-Methyl-<i>N</i>-(2,2,2-Trifluoroacetyl)Sulfilimidoyl) Anthranilic Diamide |
| title_sort | synthesis physicochemical properties and biological activities of 4 i s i methyl i n i 2 2 2 trifluoroacetyl sulfilimidoyl anthranilic diamide |
| topic | anthranilic diamide sulfilimine sulfoximine insecticide |
| url | https://www.mdpi.com/1420-3049/24/19/3451 |
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