Jianwei Xu, Zihan Dou, Sihui Zuo, Min Lv, Yanyan Wang, Meng Hao, Lin Chen, Hui Xu
{"title":"槐果碱基异噁唑啉衍生物的半制备、X 射线单晶结构及其杀虫效果和毒理学研究","authors":"Jianwei Xu, Zihan Dou, Sihui Zuo, Min Lv, Yanyan Wang, Meng Hao, Lin Chen, Hui Xu","doi":"10.1021/acs.jafc.3c08101","DOIUrl":null,"url":null,"abstract":"Recently, research and development of novel pesticides from natural plant products have received much attention. To accelerate the application of sophocarpine as the agrochemical candidate, a series of novel sophocarpine-based isoxazoline derivatives were prepared by the 1,3-dipolar [2 + 3] cycloaddition reaction of sophocarpine with different chloroximes. Their structures were well characterized by high-resolution mass spectra, infrared spectra, and proton/carbon-13 nuclear magnetic resonance spectra. Eight steric configurations of compounds <b>5a</b>, <b>5e’</b>, <b>5f</b>, <b>5g</b>, <b>5h</b>, <b>5i</b>, <b>5r</b>, and <b>5u’</b> were further determined by X-ray single-crystallography. Against <i>Aphis citricola</i> Van der Goot, compounds <b>5n</b> (LD<sub>50</sub>: 0.032 μg/nymph) and <b>5o</b> (LD<sub>50</sub>: 0.024 μg/nymph) exhibited greater than 3.7- and 4.9-fold potent aphicidal activity compared to sophocarpine (LD<sub>50</sub>: 0.118 μg/nymph). Against <i>Tetranychus cinnabarinus</i> Boisduval, derivative <b>5g</b> displayed the most promising acaricidal activity with the LC<sub>50</sub> value of 0.247 mg/mL, which was 14.2-fold that of sophocarpine. Compounds <b>5d</b> and <b>5g</b> also exhibited good control efficacy against <i>T. cinnabarinus</i>. Scanning electron microscopy images indicated that compound <b>5g</b> can destroy the mite cuticle layer. These results will provide the foundation for the structural modification and use of sophocarpine derivatives as agrochemicals in the future.","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":5.7000,"publicationDate":"2024-10-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Semi-Preparation and X-ray Single-Crystal Structures of Sophocarpine-Based Isoxazoline Derivatives and Their Pesticidal Effects and Toxicology Study\",\"authors\":\"Jianwei Xu, Zihan Dou, Sihui Zuo, Min Lv, Yanyan Wang, Meng Hao, Lin Chen, Hui Xu\",\"doi\":\"10.1021/acs.jafc.3c08101\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Recently, research and development of novel pesticides from natural plant products have received much attention. To accelerate the application of sophocarpine as the agrochemical candidate, a series of novel sophocarpine-based isoxazoline derivatives were prepared by the 1,3-dipolar [2 + 3] cycloaddition reaction of sophocarpine with different chloroximes. Their structures were well characterized by high-resolution mass spectra, infrared spectra, and proton/carbon-13 nuclear magnetic resonance spectra. Eight steric configurations of compounds <b>5a</b>, <b>5e’</b>, <b>5f</b>, <b>5g</b>, <b>5h</b>, <b>5i</b>, <b>5r</b>, and <b>5u’</b> were further determined by X-ray single-crystallography. Against <i>Aphis citricola</i> Van der Goot, compounds <b>5n</b> (LD<sub>50</sub>: 0.032 μg/nymph) and <b>5o</b> (LD<sub>50</sub>: 0.024 μg/nymph) exhibited greater than 3.7- and 4.9-fold potent aphicidal activity compared to sophocarpine (LD<sub>50</sub>: 0.118 μg/nymph). Against <i>Tetranychus cinnabarinus</i> Boisduval, derivative <b>5g</b> displayed the most promising acaricidal activity with the LC<sub>50</sub> value of 0.247 mg/mL, which was 14.2-fold that of sophocarpine. Compounds <b>5d</b> and <b>5g</b> also exhibited good control efficacy against <i>T. cinnabarinus</i>. Scanning electron microscopy images indicated that compound <b>5g</b> can destroy the mite cuticle layer. These results will provide the foundation for the structural modification and use of sophocarpine derivatives as agrochemicals in the future.\",\"PeriodicalId\":41,\"journal\":{\"name\":\"Journal of Agricultural and Food Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":5.7000,\"publicationDate\":\"2024-10-26\",\"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.3c08101\",\"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.3c08101","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}
Semi-Preparation and X-ray Single-Crystal Structures of Sophocarpine-Based Isoxazoline Derivatives and Their Pesticidal Effects and Toxicology Study
Recently, research and development of novel pesticides from natural plant products have received much attention. To accelerate the application of sophocarpine as the agrochemical candidate, a series of novel sophocarpine-based isoxazoline derivatives were prepared by the 1,3-dipolar [2 + 3] cycloaddition reaction of sophocarpine with different chloroximes. Their structures were well characterized by high-resolution mass spectra, infrared spectra, and proton/carbon-13 nuclear magnetic resonance spectra. Eight steric configurations of compounds 5a, 5e’, 5f, 5g, 5h, 5i, 5r, and 5u’ were further determined by X-ray single-crystallography. Against Aphis citricola Van der Goot, compounds 5n (LD50: 0.032 μg/nymph) and 5o (LD50: 0.024 μg/nymph) exhibited greater than 3.7- and 4.9-fold potent aphicidal activity compared to sophocarpine (LD50: 0.118 μg/nymph). Against Tetranychus cinnabarinus Boisduval, derivative 5g displayed the most promising acaricidal activity with the LC50 value of 0.247 mg/mL, which was 14.2-fold that of sophocarpine. Compounds 5d and 5g also exhibited good control efficacy against T. cinnabarinus. Scanning electron microscopy images indicated that compound 5g can destroy the mite cuticle layer. These results will provide the foundation for the structural modification and use of sophocarpine derivatives as agrochemicals in the future.
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.