Yueqiang Xin , Zexu Pan , Yangshan Liu , Xiang Ji , Yanjun Hao , Hongyan Cao , Yuli Sang
{"title":"苯丙酮及其结构类似物对黄颡鱼蛾(鞘翅目:拟甲科)的抗虫活性","authors":"Yueqiang Xin , Zexu Pan , Yangshan Liu , Xiang Ji , Yanjun Hao , Hongyan Cao , Yuli Sang","doi":"10.1016/j.toxicon.2025.108378","DOIUrl":null,"url":null,"abstract":"<div><div>Several studies have confirmed that the volatile oil of <em>Rhododendron anthopogonoides</em> Maxim has good anti-insect activity and is expected to become an environmentally friendly botanical insecticide, with benzylacetone as its main active component. Benzylacetone has a simple chemical structure, containing only three elements of carbon, hydrogen and oxygen, low toxicity, and easy degradation. Therefore, in this study, benzylacetone and its seven structural analogues were selected for testing their anti-insect activity to <em>Tribolium castaneum</em> Herbst (Coleoptera: Tenebrionidae), in order to explore the key structural sites where benzylacetone plays a role in combating <em>T. castaneum</em>. Benzylacetone demonstrated better repellent activity compared to the positive control pyrethroid, and when the single bonds at positions 3 and 4 were transformed into double bonds, the percent repellency increased. Additionally, the fumigation activity of benzylacetone exhibited a concentration-dependent trend and was significantly higher than that of the positive control pyrethroid. After losing two methylene groups at positions 3 and 4, the LC50 decreased to 13.10 mg/L air, which was approximately 9.4 times lower than that of benzylacetone. In terms of contact activity against <em>T. castaneum</em>, benzylacetone was about 2 times more effective than pyrethroids. Moreover, when the single bond at positions 3 and 4 became a double bond, the contact mortality was 2.5 times higher than that of benzylacetone, and the LD50 reached 10.47 μg/adult. Based on the results of repellent, fumigation, and contact toxicity experiments, it was found that the side chains of benzylacetone, carbonyl groups on the side chains, and benzene ring unsubstituted were the key structures for its prevention and control against <em>T. castaneum</em>. This study is an exploration of the structure-activity relationship of benzylacetone in the anti-insect of <em>T. castaneum</em>, providing ideas for its structural modification.</div></div>","PeriodicalId":23289,"journal":{"name":"Toxicon","volume":"261 ","pages":"Article 108378"},"PeriodicalIF":2.6000,"publicationDate":"2025-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Anti-insect activity of benzylacetone and its structural analogues against Tribolium castaneum (Coleoptera: Tenebrionidae)\",\"authors\":\"Yueqiang Xin , Zexu Pan , Yangshan Liu , Xiang Ji , Yanjun Hao , Hongyan Cao , Yuli Sang\",\"doi\":\"10.1016/j.toxicon.2025.108378\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Several studies have confirmed that the volatile oil of <em>Rhododendron anthopogonoides</em> Maxim has good anti-insect activity and is expected to become an environmentally friendly botanical insecticide, with benzylacetone as its main active component. Benzylacetone has a simple chemical structure, containing only three elements of carbon, hydrogen and oxygen, low toxicity, and easy degradation. Therefore, in this study, benzylacetone and its seven structural analogues were selected for testing their anti-insect activity to <em>Tribolium castaneum</em> Herbst (Coleoptera: Tenebrionidae), in order to explore the key structural sites where benzylacetone plays a role in combating <em>T. castaneum</em>. Benzylacetone demonstrated better repellent activity compared to the positive control pyrethroid, and when the single bonds at positions 3 and 4 were transformed into double bonds, the percent repellency increased. Additionally, the fumigation activity of benzylacetone exhibited a concentration-dependent trend and was significantly higher than that of the positive control pyrethroid. After losing two methylene groups at positions 3 and 4, the LC50 decreased to 13.10 mg/L air, which was approximately 9.4 times lower than that of benzylacetone. In terms of contact activity against <em>T. castaneum</em>, benzylacetone was about 2 times more effective than pyrethroids. Moreover, when the single bond at positions 3 and 4 became a double bond, the contact mortality was 2.5 times higher than that of benzylacetone, and the LD50 reached 10.47 μg/adult. Based on the results of repellent, fumigation, and contact toxicity experiments, it was found that the side chains of benzylacetone, carbonyl groups on the side chains, and benzene ring unsubstituted were the key structures for its prevention and control against <em>T. castaneum</em>. This study is an exploration of the structure-activity relationship of benzylacetone in the anti-insect of <em>T. castaneum</em>, providing ideas for its structural modification.</div></div>\",\"PeriodicalId\":23289,\"journal\":{\"name\":\"Toxicon\",\"volume\":\"261 \",\"pages\":\"Article 108378\"},\"PeriodicalIF\":2.6000,\"publicationDate\":\"2025-04-29\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Toxicon\",\"FirstCategoryId\":\"3\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0041010125001527\",\"RegionNum\":4,\"RegionCategory\":\"医学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"PHARMACOLOGY & PHARMACY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Toxicon","FirstCategoryId":"3","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0041010125001527","RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"PHARMACOLOGY & PHARMACY","Score":null,"Total":0}
Anti-insect activity of benzylacetone and its structural analogues against Tribolium castaneum (Coleoptera: Tenebrionidae)
Several studies have confirmed that the volatile oil of Rhododendron anthopogonoides Maxim has good anti-insect activity and is expected to become an environmentally friendly botanical insecticide, with benzylacetone as its main active component. Benzylacetone has a simple chemical structure, containing only three elements of carbon, hydrogen and oxygen, low toxicity, and easy degradation. Therefore, in this study, benzylacetone and its seven structural analogues were selected for testing their anti-insect activity to Tribolium castaneum Herbst (Coleoptera: Tenebrionidae), in order to explore the key structural sites where benzylacetone plays a role in combating T. castaneum. Benzylacetone demonstrated better repellent activity compared to the positive control pyrethroid, and when the single bonds at positions 3 and 4 were transformed into double bonds, the percent repellency increased. Additionally, the fumigation activity of benzylacetone exhibited a concentration-dependent trend and was significantly higher than that of the positive control pyrethroid. After losing two methylene groups at positions 3 and 4, the LC50 decreased to 13.10 mg/L air, which was approximately 9.4 times lower than that of benzylacetone. In terms of contact activity against T. castaneum, benzylacetone was about 2 times more effective than pyrethroids. Moreover, when the single bond at positions 3 and 4 became a double bond, the contact mortality was 2.5 times higher than that of benzylacetone, and the LD50 reached 10.47 μg/adult. Based on the results of repellent, fumigation, and contact toxicity experiments, it was found that the side chains of benzylacetone, carbonyl groups on the side chains, and benzene ring unsubstituted were the key structures for its prevention and control against T. castaneum. This study is an exploration of the structure-activity relationship of benzylacetone in the anti-insect of T. castaneum, providing ideas for its structural modification.
期刊介绍:
Toxicon has an open access mirror Toxicon: X, sharing the same aims and scope, editorial team, submission system and rigorous peer review. An introductory offer Toxicon: X - full waiver of the Open Access fee.
Toxicon''s "aims and scope" are to publish:
-articles containing the results of original research on problems related to toxins derived from animals, plants and microorganisms
-papers on novel findings related to the chemical, pharmacological, toxicological, and immunological properties of natural toxins
-molecular biological studies of toxins and other genes from poisonous and venomous organisms that advance understanding of the role or function of toxins
-clinical observations on poisoning and envenoming where a new therapeutic principle has been proposed or a decidedly superior clinical result has been obtained.
-material on the use of toxins as tools in studying biological processes and material on subjects related to venom and antivenom problems.
-articles on the translational application of toxins, for example as drugs and insecticides
-epidemiological studies on envenoming or poisoning, so long as they highlight a previously unrecognised medical problem or provide insight into the prevention or medical treatment of envenoming or poisoning. Retrospective surveys of hospital records, especially those lacking species identification, will not be considered for publication. Properly designed prospective community-based surveys are strongly encouraged.
-articles describing well-known activities of venoms, such as antibacterial, anticancer, and analgesic activities of arachnid venoms, without any attempt to define the mechanism of action or purify the active component, will not be considered for publication in Toxicon.
-review articles on problems related to toxinology.
To encourage the exchange of ideas, sections of the journal may be devoted to Short Communications, Letters to the Editor and activities of the affiliated societies.