Biaobiao Jiang, Di Feng, Jun Shi, Wei Wu, Yawen Dong, Hai Ren
{"title":"含有酰肼分子的异噁唑啉衍生物的设计、合成和杀虫活性","authors":"Biaobiao Jiang, Di Feng, Jun Shi, Wei Wu, Yawen Dong, Hai Ren","doi":"10.1021/acs.jafc.4c04005","DOIUrl":null,"url":null,"abstract":"The long-term use of agricultural insecticides has led to the development of resistant strains. In this context, the isoxazoline structure has become an active area of pesticide research owing to its wide insecticidal spectrum, nontoxicity to mammals, and lack of cross-resistance with known insecticides. In the present study, based on the discovery of compound <b>G22</b> in our previous work, a series of novel isoxazoline compounds containing acylhydrazine were designed and synthesized using a scaffold hopping strategy. The insecticidal activities of the target compounds were assessed, and compound <b>L17</b> (LC<sub>50</sub> = 0.489 mg/L) showed insecticidal activity against <i>Spodoptera frugiperda</i> superior to those of the commercial insecticides indoxacarb (LC<sub>50</sub> = 3.14 mg/L) and fluralaner (LC<sub>50</sub> = 0.659 mg/L). Theoretical calculations indicated that the introduction of acylhydrazine plays an important role in the biological activity of the target compounds. Furthermore, the enzyme-linked immunosorbent assay and molecular docking results indicated that <b>L17</b> may act on the GABA receptor of the target insect. These results indicated that <b>L17</b> is a potential candidate compound for controlling <i>S. frugiperda</i> populations in agriculture.","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":5.7000,"publicationDate":"2024-09-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Design, Synthesis, and Insecticidal Activity of Isoxazoline Derivatives Incorporating an Acylhydrazine Moiety\",\"authors\":\"Biaobiao Jiang, Di Feng, Jun Shi, Wei Wu, Yawen Dong, Hai Ren\",\"doi\":\"10.1021/acs.jafc.4c04005\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"The long-term use of agricultural insecticides has led to the development of resistant strains. In this context, the isoxazoline structure has become an active area of pesticide research owing to its wide insecticidal spectrum, nontoxicity to mammals, and lack of cross-resistance with known insecticides. In the present study, based on the discovery of compound <b>G22</b> in our previous work, a series of novel isoxazoline compounds containing acylhydrazine were designed and synthesized using a scaffold hopping strategy. The insecticidal activities of the target compounds were assessed, and compound <b>L17</b> (LC<sub>50</sub> = 0.489 mg/L) showed insecticidal activity against <i>Spodoptera frugiperda</i> superior to those of the commercial insecticides indoxacarb (LC<sub>50</sub> = 3.14 mg/L) and fluralaner (LC<sub>50</sub> = 0.659 mg/L). Theoretical calculations indicated that the introduction of acylhydrazine plays an important role in the biological activity of the target compounds. Furthermore, the enzyme-linked immunosorbent assay and molecular docking results indicated that <b>L17</b> may act on the GABA receptor of the target insect. These results indicated that <b>L17</b> is a potential candidate compound for controlling <i>S. frugiperda</i> populations in agriculture.\",\"PeriodicalId\":41,\"journal\":{\"name\":\"Journal of Agricultural and Food Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":5.7000,\"publicationDate\":\"2024-09-16\",\"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://doi.org/10.1021/acs.jafc.4c04005\",\"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://doi.org/10.1021/acs.jafc.4c04005","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 Insecticidal Activity of Isoxazoline Derivatives Incorporating an Acylhydrazine Moiety
The long-term use of agricultural insecticides has led to the development of resistant strains. In this context, the isoxazoline structure has become an active area of pesticide research owing to its wide insecticidal spectrum, nontoxicity to mammals, and lack of cross-resistance with known insecticides. In the present study, based on the discovery of compound G22 in our previous work, a series of novel isoxazoline compounds containing acylhydrazine were designed and synthesized using a scaffold hopping strategy. The insecticidal activities of the target compounds were assessed, and compound L17 (LC50 = 0.489 mg/L) showed insecticidal activity against Spodoptera frugiperda superior to those of the commercial insecticides indoxacarb (LC50 = 3.14 mg/L) and fluralaner (LC50 = 0.659 mg/L). Theoretical calculations indicated that the introduction of acylhydrazine plays an important role in the biological activity of the target compounds. Furthermore, the enzyme-linked immunosorbent assay and molecular docking results indicated that L17 may act on the GABA receptor of the target insect. These results indicated that L17 is a potential candidate compound for controlling S. frugiperda populations in agriculture.
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.