Sulfonate derivatives bearing an amide unit: design, synthesis and biological activity studies
Abstract Pest disasters which occurs on crops is a serious problem that not only cause crop yield loss or even crop failure but can also spread a number of plant diseases.Sulfonate derivatives have been widely used in insecticide and fungicide research in recent years. On this basis, a series of sul...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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BMC
2024-03-01
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| Series: | BMC Chemistry |
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| Online Access: | https://doi.org/10.1186/s13065-024-01151-0 |
| _version_ | 1797266943539937280 |
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| author | You-hua Liu Chang-kun Li Mao-yu Nie Fa-li Wang Xiao-li Ren Lin-hong Jin Xia Zhou |
| author_facet | You-hua Liu Chang-kun Li Mao-yu Nie Fa-li Wang Xiao-li Ren Lin-hong Jin Xia Zhou |
| author_sort | You-hua Liu |
| collection | DOAJ |
| description | Abstract Pest disasters which occurs on crops is a serious problem that not only cause crop yield loss or even crop failure but can also spread a number of plant diseases.Sulfonate derivatives have been widely used in insecticide and fungicide research in recent years. On this basis, a series of sulfonate derivatives bearing an amide unit are synthesized and the biological activities are evaluated. The bioassay results showed that compounds A 8 , A 13 , A 16 , B 1 , B 3 , B 4 , B 5 , B 10 , B 12 − 20 , C 3 , C 5 , C 9 , C 10 , C 14 , C 15 , C 17 and C 19 showed 100% activity at a concentration of 500 µg/mL against the Plutella xylostella (P. xylostella). Among them, B 15 which contains a thiadiazole sulfonate structure still shows 100% activity at 50 µg/mL concentration against P. xylostella and had the lowest median lethal concentration (LC50) (7.61 µg/mL) among the target compounds. Further mechanism studies are conducted on compounds with better insecticidal activity. Molecular docking results shows that B 15 formed hydrophobic interactions π-π and hydrogen bonds with the indole ring of Trp532 and the carboxyl group of Asp384, respectively, with similar interaction distances or bond lengths as those of diflubenzuron. Moreover, chitinase inhibition assays are performed to further demonstrate its mode of action. In addition, the anti-bacterial activity of the series of compounds is also tested and the results showed that the series of compounds has moderate biological activity against Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas oryzae pv. oryzicola (Xoc), with inhibition rates of 91%, 92% and 92%, 88% at the concentration of 100 µg/mL, respectively. Our study indicates that B 15 can be used as a novel insecticide for crop protection. Graphical Abstract |
| first_indexed | 2024-04-25T01:08:43Z |
| format | Article |
| id | doaj.art-ce0442c398444802a833c69b4b00bffb |
| institution | Directory Open Access Journal |
| issn | 2661-801X |
| language | English |
| last_indexed | 2024-04-25T01:08:43Z |
| publishDate | 2024-03-01 |
| publisher | BMC |
| record_format | Article |
| series | BMC Chemistry |
| spelling | doaj.art-ce0442c398444802a833c69b4b00bffb2024-03-10T12:05:02ZengBMCBMC Chemistry2661-801X2024-03-0118111310.1186/s13065-024-01151-0Sulfonate derivatives bearing an amide unit: design, synthesis and biological activity studiesYou-hua Liu0Chang-kun Li1Mao-yu Nie2Fa-li Wang3Xiao-li Ren4Lin-hong Jin5Xia Zhou6National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou UniversityNational Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou UniversityNational Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou UniversityNational Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou UniversityNational Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou UniversityNational Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou UniversityNational Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou UniversityAbstract Pest disasters which occurs on crops is a serious problem that not only cause crop yield loss or even crop failure but can also spread a number of plant diseases.Sulfonate derivatives have been widely used in insecticide and fungicide research in recent years. On this basis, a series of sulfonate derivatives bearing an amide unit are synthesized and the biological activities are evaluated. The bioassay results showed that compounds A 8 , A 13 , A 16 , B 1 , B 3 , B 4 , B 5 , B 10 , B 12 − 20 , C 3 , C 5 , C 9 , C 10 , C 14 , C 15 , C 17 and C 19 showed 100% activity at a concentration of 500 µg/mL against the Plutella xylostella (P. xylostella). Among them, B 15 which contains a thiadiazole sulfonate structure still shows 100% activity at 50 µg/mL concentration against P. xylostella and had the lowest median lethal concentration (LC50) (7.61 µg/mL) among the target compounds. Further mechanism studies are conducted on compounds with better insecticidal activity. Molecular docking results shows that B 15 formed hydrophobic interactions π-π and hydrogen bonds with the indole ring of Trp532 and the carboxyl group of Asp384, respectively, with similar interaction distances or bond lengths as those of diflubenzuron. Moreover, chitinase inhibition assays are performed to further demonstrate its mode of action. In addition, the anti-bacterial activity of the series of compounds is also tested and the results showed that the series of compounds has moderate biological activity against Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas oryzae pv. oryzicola (Xoc), with inhibition rates of 91%, 92% and 92%, 88% at the concentration of 100 µg/mL, respectively. Our study indicates that B 15 can be used as a novel insecticide for crop protection. Graphical Abstracthttps://doi.org/10.1186/s13065-024-01151-0Sulfonate derivativesSynthesisPesticidesBiological activity |
| spellingShingle | You-hua Liu Chang-kun Li Mao-yu Nie Fa-li Wang Xiao-li Ren Lin-hong Jin Xia Zhou Sulfonate derivatives bearing an amide unit: design, synthesis and biological activity studies BMC Chemistry Sulfonate derivatives Synthesis Pesticides Biological activity |
| title | Sulfonate derivatives bearing an amide unit: design, synthesis and biological activity studies |
| title_full | Sulfonate derivatives bearing an amide unit: design, synthesis and biological activity studies |
| title_fullStr | Sulfonate derivatives bearing an amide unit: design, synthesis and biological activity studies |
| title_full_unstemmed | Sulfonate derivatives bearing an amide unit: design, synthesis and biological activity studies |
| title_short | Sulfonate derivatives bearing an amide unit: design, synthesis and biological activity studies |
| title_sort | sulfonate derivatives bearing an amide unit design synthesis and biological activity studies |
| topic | Sulfonate derivatives Synthesis Pesticides Biological activity |
| url | https://doi.org/10.1186/s13065-024-01151-0 |
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