Dongdong Liu, Jialin Ye, Yixing Gao, Hongyan Pei, Chunfeng Luo, Huan Tian, Juan He, Jing Zhang* and Lixin Zhang*,
{"title":"含有酰亚胺分子的新型苯基吡唑衍生物的设计、合成和杀螨/杀虫活性","authors":"Dongdong Liu, Jialin Ye, Yixing Gao, Hongyan Pei, Chunfeng Luo, Huan Tian, Juan He, Jing Zhang* and Lixin Zhang*, ","doi":"10.1021/acs.jafc.4c02841","DOIUrl":null,"url":null,"abstract":"<p >Using nicofluprole as the lead compound, we designed and synthesized a series of new phenylpyrazole analogues through substituting the methyl group on the nitrogen atom of the amide with an acyl group. Bioassay results showed that compounds <b>A12</b>–<b>A17</b> with a 1-cyanocyclopropimide group exhibited outstanding insecticidal activity. The LC<sub>50</sub> values for compounds <b>A12</b>–<b>A17</b> against <i>Tetranychus cinnabarinus</i> ranged from 0.58 to 0.91 mg/L. Compound <b>A15</b> showed an LC<sub>50</sub> value of 0.29 and 3.10 mg/L against <i>Plutella xylostella</i> and <i>Myzus persicae</i>, respectively. Molecular docking indicated the potential binding interactions of compound <b>A15</b> with a gamma-aminobutyric acid receptor. Additionally, density functional theory calculations implied that the 1-cyanocyclopropimide structure might be essential for its biological activity. Phenylpyrazole derivatives, containing a 1-cyanocyclopropimide fragment, have the potential for further development as potential insecticides.</p>","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":5.7000,"publicationDate":"2024-06-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Design, Synthesis, and Acaricidal/Insecticidal Activities of New Phenylpyrazole Derivatives Comprising an Imide Moiety\",\"authors\":\"Dongdong Liu, Jialin Ye, Yixing Gao, Hongyan Pei, Chunfeng Luo, Huan Tian, Juan He, Jing Zhang* and Lixin Zhang*, \",\"doi\":\"10.1021/acs.jafc.4c02841\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >Using nicofluprole as the lead compound, we designed and synthesized a series of new phenylpyrazole analogues through substituting the methyl group on the nitrogen atom of the amide with an acyl group. Bioassay results showed that compounds <b>A12</b>–<b>A17</b> with a 1-cyanocyclopropimide group exhibited outstanding insecticidal activity. The LC<sub>50</sub> values for compounds <b>A12</b>–<b>A17</b> against <i>Tetranychus cinnabarinus</i> ranged from 0.58 to 0.91 mg/L. Compound <b>A15</b> showed an LC<sub>50</sub> value of 0.29 and 3.10 mg/L against <i>Plutella xylostella</i> and <i>Myzus persicae</i>, respectively. Molecular docking indicated the potential binding interactions of compound <b>A15</b> with a gamma-aminobutyric acid receptor. Additionally, density functional theory calculations implied that the 1-cyanocyclopropimide structure might be essential for its biological activity. Phenylpyrazole derivatives, containing a 1-cyanocyclopropimide fragment, have the potential for further development as potential insecticides.</p>\",\"PeriodicalId\":41,\"journal\":{\"name\":\"Journal of Agricultural and Food Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":5.7000,\"publicationDate\":\"2024-06-29\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Agricultural and Food Chemistry\",\"FirstCategoryId\":\"97\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.jafc.4c02841\",\"RegionNum\":1,\"RegionCategory\":\"农林科学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"AGRICULTURE, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Agricultural and Food Chemistry","FirstCategoryId":"97","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.jafc.4c02841","RegionNum":1,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"AGRICULTURE, MULTIDISCIPLINARY","Score":null,"Total":0}
Design, Synthesis, and Acaricidal/Insecticidal Activities of New Phenylpyrazole Derivatives Comprising an Imide Moiety
Using nicofluprole as the lead compound, we designed and synthesized a series of new phenylpyrazole analogues through substituting the methyl group on the nitrogen atom of the amide with an acyl group. Bioassay results showed that compounds A12–A17 with a 1-cyanocyclopropimide group exhibited outstanding insecticidal activity. The LC50 values for compounds A12–A17 against Tetranychus cinnabarinus ranged from 0.58 to 0.91 mg/L. Compound A15 showed an LC50 value of 0.29 and 3.10 mg/L against Plutella xylostella and Myzus persicae, respectively. Molecular docking indicated the potential binding interactions of compound A15 with a gamma-aminobutyric acid receptor. Additionally, density functional theory calculations implied that the 1-cyanocyclopropimide structure might be essential for its biological activity. Phenylpyrazole derivatives, containing a 1-cyanocyclopropimide fragment, have the potential for further development as potential insecticides.
期刊介绍:
The Journal of Agricultural and Food Chemistry publishes high-quality, cutting edge original research representing complete studies and research advances dealing with the chemistry and biochemistry of agriculture and food. The Journal also encourages papers with chemistry and/or biochemistry as a major component combined with biological/sensory/nutritional/toxicological evaluation related to agriculture and/or food.