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Overview of Kenji Mori's pheromone synthesis series. 森健二信息素合成系列综述。
IF 2.4 4区 农林科学 Q2 ENTOMOLOGY Pub Date : 2023-02-20 DOI: 10.1584/jpestics.D22-062
Hirosato Takikawa, Shigefumi Kuwahara

It was the late Professor Kenji Mori, the giant of pheromone synthesis and pioneer of pheromone stereochemistry, who laid the foundation for the practical application of insect pheromones, which play an important role in Integrated Pest Management, one of the key concepts of agriculture in the 21st century. Therefore, it would be meaningful to retrace his achievements at this time, three and a half years after his death. In this review, we would like to introduce some of his notable synthetic studies from his Pheromone Synthesis Series and reconfirm his contributions to the development of pheromone chemistry and their impacts on natural science.

已故的森健二教授是信息素合成的巨人和信息素立体化学的先驱,他为昆虫信息素的实际应用奠定了基础,昆虫信息素在21世纪农业的关键概念之一——害虫综合治理中发挥了重要作用。因此,在他去世三年半后的今天,回顾他的成就是有意义的。在本文中,我们将介绍他在信息素合成系列中一些重要的合成研究,并再次肯定他对信息素化学发展的贡献及其对自然科学的影响。
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引用次数: 0
Novel fungicide quinofumelin shows selectivity for fungal dihydroorotate dehydrogenase over the corresponding human enzyme. 新型杀菌剂喹诺芬林对真菌二氢乙酸脱氢酶的选择性优于相应的人酶。
IF 2.4 4区 农林科学 Q2 ENTOMOLOGY Pub Date : 2023-02-20 DOI: 10.1584/jpestics.D22-035
Norikazu Higashimura, Akira Hamada, Shinichi Banba

The species selectivity of class 2 dihydroorotate dehydrogenase (DHODH), a target enzyme for quinofumelin, was examined. The Homo sapiens DHODH (HsDHODH) assay system was developed to compare the selectivity of quinofumelin for fungi with that for mammals. The IC50 values of quinofumelin for Pyricularia oryzae DHODH (PoDHODH) and HsDHODH were 2.8 nM and >100 µM, respectively. Quinofumelin was highly selective for fungal over human DHODH. Additionally, we constructed recombinant P. oryzae mutants where PoDHODH (PoPYR4) or HsDHODH was inserted into the PoPYR4 disruption mutant. At quinofumelin concentration of 0.01-1 ppm, the PoPYR4 insertion mutants could not grow, but the HsDHODH gene-insertion mutants thrived. This indicates that HsDHODH is a substitute for PoDHODH, and quinofumelin could not inhibit HsDHODH as in the HsDHODH enzyme assay. Comparing the amino acid sequences of human and fungal DHODHs indicates that the significant difference at the ubiquinone-binding site contributes to the species selectivity of quinofumelin.

研究了喹诺菲林靶酶2类二氢羟酸脱氢酶(DHODH)的物种选择性。为了比较喹诺菲林对真菌和哺乳动物的选择性,建立了智人DHODH (HsDHODH)检测系统。喹诺菲林对稻瘟霉DHODH (PoDHODH)和HsDHODH的IC50值分别为2.8 nM和>100µM。喹诺菲林对真菌的选择性高于人DHODH。此外,我们构建了重组稻瘟病菌突变体,将PoDHODH (PoPYR4)或HsDHODH插入到PoPYR4断裂突变体中。在0.01 ~ 1 ppm的喹诺菲林浓度下,PoPYR4插入突变体不能生长,而HsDHODH基因插入突变体能够生长。这表明HsDHODH是PoDHODH的替代品,喹诺菲林不能像在HsDHODH酶实验中那样抑制HsDHODH。比较人和真菌DHODHs的氨基酸序列表明,在泛素结合位点上的显著差异有助于喹诺菲林的物种选择性。
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引用次数: 0
Synthesis and herbicidal activity of optically active cinmethylin, its enantiomer, and C3-substituted cinmethylin analogs. 旋光性辛甲基林及其对映体和c3取代辛甲基林类似物的合成及其除草活性。
IF 2.4 4区 农林科学 Q2 ENTOMOLOGY Pub Date : 2023-02-20 DOI: 10.1584/jpestics.D22-051
Narihito Ogawa, Shoya Toyoshima, Shinya Sekikawa, Masahiro Ishijima, Kyosuke Katagiri, Chihiro Uematsu, Tatsuya Hirano, Akihito Ootaka, Jun Suzuki

We investigated the synthesis and herbicidal activity of optically active cinmethylin, its enantiomer, and C3-substituted cinmethylin analogs. Optically active cinmethylin could be obtained in seven steps with the Sharpless asymmetric dihydroxylation of α-terpinene. The synthesized cinmethylin and its enantiomer showed similar herbicidal activity, which was independent of the stereochemistry. Next, we synthesized cinmethylin analogs with various substituents at the C3 position. We found that analogs with methylene, oxime, ketone, or methyl groups at the C3 position show excellent herbicidal activity.

研究了旋光性辛甲基林及其对映体和c3取代辛甲基林类似物的合成及其除草活性。α-萜烯经Sharpless不对称二羟基化反应,经7步反应制得光学活性的五甲基林。合成的五甲基林及其对映体具有相似的除草活性,且与立体化学无关。接下来,我们合成了具有不同C3取代基的辛甲基林类似物。我们发现在C3位置上含有亚甲基、肟、酮或甲基的类似物具有良好的除草活性。
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引用次数: 0
Design and biological activity of a novel fungicide, quinofumelin. 新型杀菌剂喹诺芬林的设计及生物活性研究。
IF 2.4 4区 农林科学 Q2 ENTOMOLOGY Pub Date : 2023-02-20 DOI: 10.1584/jpestics.D22-042
Hiroyuki Ito, Takeshi Takada, Munetsugu Morimoto, Hiroyuki Komai, Fumie Kajino, Toshiaki Ohara, Yasushi Tamagawa, Mikio Tsuda, Shinichi Banba

Developed by Mitsui Chemicals Agro, Inc. (Tokyo, Japan), quinofumelin is a novel fungicide with a distinct chemical structure including 3-(isoquinolin-1-yl) quinoline, demonstrating fungicidal activity against a variety of fungi, including rice blast and gray mold. We screened our compound library to identify curative compounds for rice blast and evaluated the effect of fungicide-resistant strains of gray mold. Our research demonstrated that quinofumelin has curative effects against rice blast and is not cross-resistant to existing fungicides. Accordingly, the use of quinofumelin can be considered a novel approach for disease control in agricultural production. In this report, the discovery of quinofumelin from the initial compound is described in detail.

quinofumelin是由日本三井化学农业公司(Tokyo, Japan)开发的一种新型杀菌剂,具有独特的化学结构,包括3-(异喹啉-1-基)喹啉,对多种真菌(包括稻瘟菌和灰霉病)具有杀真菌活性。筛选化合物文库,鉴定稻瘟病治疗化合物,并评价灰霉抗杀菌剂菌株的效果。我们的研究表明,喹诺菲林对稻瘟病菌有治疗效果,而且对现有的杀菌剂没有交叉抗性。因此,喹诺菲林的使用可被认为是农业生产中疾病控制的一种新方法。在这篇报告中,详细描述了从最初的化合物中发现喹诺菲林的过程。
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引用次数: 0
Quantitative evaluation of the biological activity of various brassinosteroids using spiral root induction in rice seeds 水稻螺旋根诱导对油菜素内酯生物活性的定量评价
4区 农林科学 Q2 ENTOMOLOGY Pub Date : 2023-01-01 DOI: 10.1584/jpestics.d23-044
Bunta Nishikawa, Kotaro Mori, Seisuke Takimoto, Bunta Watanabe, Midori Matsuo, Takeshi Nakano, Yoshiaki Nakagawa, Hisashi Miyagawa
Spiral roots are induced in germinated rice seeds through treatment with nanomolar brassinosteroids (BRs) but not with other plant hormones. Here, we determined the minimum effective concentration (MEC) of various BRs to induce spiral roots in germinated rice seeds. The reciprocal logarithm of MEC, pMEC, was used as the BL-like activity index, which was linearly correlated with the reciprocal logarithm of a 50% effective dose (pED50) as evaluated in the rice lamina inclination assay. Furthermore, a ligand-receptor docking simulation was performed against the BL receptor complex, Arabidopsis thaliana BRI1/SERK1, and the binding free energy (ΔGbind) was calculated for the tested BRs. The ΔGbind calculation was performed using the molecular mechanics/generalized Born surface area method on an ensemble of uncorrelated snapshots collected via molecular dynamics to predict biological activity.
在萌发的水稻种子中,通过纳摩尔油菜素内酯(BRs)处理,而不是其他植物激素处理,可以诱导出螺旋根。本研究确定了不同BRs诱导水稻萌发种子螺旋根的最低有效浓度(MEC)。用MEC的倒数对数(pMEC)作为样bl活性指数,其与水稻层倾角试验中评估的50%有效剂量(pED50)的倒数对数呈线性相关。此外,对BL受体复合物拟南芥BRI1/SERK1进行了配体-受体对接模拟,并计算了所测BRs的结合自由能(ΔGbind)。ΔGbind计算采用分子力学/广义Born表面积法对通过分子动力学收集的不相关快照集合进行计算,以预测生物活性。
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引用次数: 0
Discovery of flometoquin, a novel quinoline insecticide 新型喹啉类杀虫剂氟美托昆的发现
4区 农林科学 Q2 ENTOMOLOGY Pub Date : 2023-01-01 DOI: 10.1584/jpestics.d23-035
Takeru Kobayashi, Hiroki Hotta, Takaaki Miyake, Masahiro Nomura, Ryo Horikoshi, Kazumi Yamamoto
Flometoquin, 2-ethyl-3,7-dimethyl-6-[4-(trifluoromethoxy)phenoxy]quinolin-4-yl methyl carbonate, is a novel insecticide with a structurally unique phenoxy-quinoline. It was discovered in 2004 by the collaborative research of Nippon Kayaku and Meiji Seika Kaisha, Ltd. (currently, Mitsui Chemicals Crop & Life Solutions, Inc.). The compound demonstrates strong and quick insecticidal action against a variety of thrips species at the nymphal and adult stages through contact and feeding activity, which could minimize crop damage and economic loss by insect pest species. In addition, flometoquin is safe for tested non-target arthropods, which makes it suitable for controlling the insect pests mentioned above under Integrated Pest Management (IPM) programs. Here, we describe a structure–activity relationship study from lead generation to the discovery of flometoquin and its insecticidal properties, including knockdown activity and effects against non-targeted arthropods.
Flometoquin, 2-乙基-3,7-二甲基-6-[4-(三氟甲氧基)苯氧基]喹啉-4-基碳酸甲酯是一种结构独特的新型杀虫剂。它是由日本Kayaku和Meiji Seika Kaisha株式会社(现为三井化学作物与生命解决方案株式会社)于2004年共同研究发现的。该化合物通过接触和取食对多种蓟马若虫期和成虫期具有强效、快速的杀虫作用,可最大限度地减少害虫对作物的危害和经济损失。此外,氟米托昆对非靶节肢动物是安全的,这使得它适用于害虫综合管理(IPM)项目中上述害虫的控制。在这里,我们描述了一个结构-活性关系的研究,从铅的产生到发现氟美托昆及其杀虫特性,包括敲除活性和对非靶向节肢动物的作用。
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引用次数: 0
Biological activities of nitromethylene analogues of imidacloprid with a 4,5-dimethylated imidazolidine ring 具有4,5-二甲基化咪唑烷环的咪氯啉亚甲基类似物的生物活性
4区 农林科学 Q2 ENTOMOLOGY Pub Date : 2023-01-01 DOI: 10.1584/jpestics.d23-024
Madoka Yamamura, Satoshi Yamauchi, Hisashi Nishiwaki
Four nitromethylene analogues of imidacloprid (CH-IMIs) having a 4,5-dimethylated (diMe) imidazolidine ring were stereospecifically synthesized to evaluate their affinity for the nicotinic acetylcholine receptors of the housefly Musca domestica. Among the analogues, the 4S,5R-diMe analogue showed the highest receptor affinity (Ki=0.39 nM). The insecticidal activity against M. domestica of the synthesized compounds was also measured under synergistic and nonsynergistic conditions. Under nonsynergistic conditions, the insecticidal activity of the 4S,5R-diMe analogue was the highest. The order of the insecticidal potency of the four diMe-CH-IMIs (4S,5R->4R,5S-=4R,5R->4S,5S-diMe analogues) was the same as that of the receptor affinity. Piperonyl butoxide (PBO) did not synergize with the test compounds, but both PBO and NIA16388 applications strengthened the activity of analogues other than the 4S,5S-diMe analogue. This suggests that the configuration of the substituents on the imidazolidine ring should influence the metabolism process of CH-IMI in houseflies.
立体定向合成了4个具有4,5-二甲基化(diMe)咪唑烷环的吡虫啉(CH-IMIs)亚甲基类似物,以评价它们对家蝇烟碱乙酰胆碱受体的亲和力。其中,4S,5R-diMe类似物的受体亲和力最高(Ki=0.39 nM)。测定了合成化合物在协同和非协同条件下对家蝇的杀虫活性。在非增效条件下,4S,5R-diMe类似物的杀虫活性最高。4个diMe-CH-IMIs的杀虫效价顺序为4S、5R->4R、5S-=4R、5R->4S、5S- dime类似物)与受体亲和力顺序相同。胡椒酰丁醇(PBO)与实验化合物没有协同作用,但PBO和NIA16388的应用都增强了除4S,5S-diMe类似物外的类似物的活性。这表明咪唑烷环上取代基的构型可能影响家蝇CH-IMI的代谢过程。
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引用次数: 0
Identification of two phthalide derivatives and an oxindole compound isolated from the edible mushroom <i>Pleurotus ostreatus</i> and their inhibitory activities against plant pathogenic microorganisms 食用菌平菇(Pleurotus ostreatus&lt;/i&gt)中两个邻苯酞衍生物和一个氧化吲哚化合物的鉴定及其对植物病原微生物的抑制作用
4区 农林科学 Q2 ENTOMOLOGY Pub Date : 2023-01-01 DOI: 10.1584/jpestics.d23-039
Enrico M. Cabutaje, Kotomi Ueno, Kumiko Osaki-Oka, Kazutaka Kido, Thomas Edison E. dela Cruz, Atsushi Ishihara
The excessive use of chemical pesticides in agricultural fields for controlling plant pathogenic microorganisms harms human health, the environment, and other beneficial microorganisms in the soil and plants. To address this challenge, it is essential to isolate and discover bioactive compounds from biological resources that could inhibit plant pathogenic microorganisms. In this study, the culture filtrate of the edible mushroom Pleurotus ostreatus was subjected to bioassay-guided isolation, and two phthalide derivatives—4,6-dimethoxyphthalide (1) and 5,7-dimethoxyphthalide (2)—were identified, along with an oxindole compound—3-hydroxy-3-methyloxindole (3). The inhibitory activities of the three compounds were evaluated against four fungal and five bacterial pathogens. Remarkably, 1 and 2 exhibited the lowest IC50 values against the conidial germination and germ tube elongation of the rice blast fungus Pyricularia oryzae. However, their effectiveness against bacterial pathogens was relatively low. The (S) and (R)-enantiomers of 3-hydroxy-3-methyloxindole showed different activities against plant fungal pathogens and bacterial plant pathogens.
为了控制植物病原微生物,在农业领域过量使用化学农药危害人类健康、环境以及土壤和植物中的其他有益微生物。为了应对这一挑战,必须从生物资源中分离和发现能够抑制植物病原微生物的生物活性化合物。本研究对食用菌平菇(Pleurotus ostreatus)的培养滤液进行了生物测定指导分离,鉴定出两种邻苯酞衍生物4,6-二甲氧基酞(1)和5,7-二甲氧基酞(2),以及一种氧吲哚化合物-3-羟基-3-甲基氧吲哚(3),并对这三种化合物对四种真菌和五种细菌病原体的抑制活性进行了评价。值得注意的是,1号和2号对稻瘟病菌孢子萌发和胚管伸长的IC50值最低。然而,它们对细菌病原体的有效性相对较低。3-羟基-3-甲基氧吲哚的(S)和(R)-对映体对植物真菌病原菌和细菌病原菌表现出不同的活性。
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引用次数: 0
A simulation model (PostPLANT-Soil) for predicting pesticide concentrations in succeeding leafy vegetables: I. Validation with experimental data in a Japanese Andosol field 预测后续叶菜中农药浓度的模拟模型(种植后-土壤):1 .日本安多索田间试验数据的验证
4区 农林科学 Q2 ENTOMOLOGY Pub Date : 2023-01-01 DOI: 10.1584/jpestics.d23-006
Keiya Inao, Sayuri Namiki, Yutaka Motoki, Nobuyasu Seike, Eiki Watanabe
We developed a simulation model for predicting pesticide concentrations in succeeding leafy vegetables (PostPLANT-Soil), which includes the process of pesticide uptake from plant roots. To validate the model, we compared pesticide concentrations simulated by the model with values measured from field experiments in an upland Andosol. The model validation showed that pesticide concentrations in the plant shoot were correlated with the concentrations in the soil solution rather than those of the water-extracted pesticides. The model successfully simulated the concentration changes in plant shoots when the simulated concentrations of the pesticides in the soil solution were fitted to the measured values by considering the key parameter - the corrective coefficient for the soil adsorption coefficient. However, the simulated shoot concentrations at the appropriate harvest period exceeded the measured values. This indicates that the leafy vegetable used in this study may have some metabolic capacity for the pesticides.
我们开发了一个模拟模型,用于预测后续叶菜(后植物-土壤)中的农药浓度,其中包括植物根系对农药的吸收过程。为了验证该模型,我们将该模型模拟的农药浓度与旱地安多索的田间试验值进行了比较。模型验证表明,植物茎部农药浓度与土壤溶液浓度相关,而与水提农药浓度无关。该模型通过考虑土壤吸附系数的校正系数这一关键参数,将土壤溶液中农药的模拟浓度拟合到实测值,成功地模拟了植物枝条中的浓度变化。但在适当采收期,模拟枝条浓度超过实测值。这表明本研究使用的叶菜可能具有一定的农药代谢能力。
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引用次数: 0
The structure–activity relationship of aryloxyacetylthioureas for the inhibition of <i>Orobanche minor</i> radicle elongation 芳基氧乙酰硫脲抑制&lt;i&gt;小环切菌&lt;/i&gt的构效关系胚根伸长
4区 农林科学 Q2 ENTOMOLOGY Pub Date : 2023-01-01 DOI: 10.1584/jpestics.d23-034
Atsushi Okazawa, Shizuki Noda, Yusuke Mimura, Kotaro Fujino, Takatoshi Wakabayashi, Daisaku Ohta, Yukihiro Sugimoto, Motohiro Sonoda
Orobanchaceae root parasitic weeds cause significant damage to agriculture and become threats to global food security. Integrated pest management is a key concept in modern agriculture and requires chemicals with various modes of action. Planteose accumulates as a storage carbohydrate in the dry seeds of root parasitic weeds. In Orobanche minor seeds, planteose is hydrolyzed by an α-galactosidase, OmAGAL2, during germination. It was found that the OmAGAL2 inhibitor, PI-28, suppressed the radicle elongation of germinating O. minor seeds. This inhibitory activity against O. minor radicle elongation was evaluated for a series of aryloxyacetylthioureas synthesized based on the structure of PI-28. Compounds with a 3-Cl or 4-Cl substituent on the benzene ring in the phenoxy moiety in PI-28 exhibited more potent activity than the parent PI-28. This is the first report on the effect of aryloxyacetylthioureas on a root parasitic weed and will contribute to the development of control reagents for root parasitic weeds.
根寄生杂草对农业造成严重危害,对全球粮食安全构成威胁。有害生物综合治理是现代农业的一个重要概念,需要多种作用方式的化学品。植物糖作为储存碳水化合物在根寄生杂草的干燥种子中积累。在Orobanche minor种子中,植物糖在萌发时被α-半乳糖苷酶OmAGAL2水解。发现OmAGAL2抑制剂PI-28抑制萌发的O. minor种子的胚根伸长。以PI-28的结构为基础合成了一系列芳基乙酰硫脲,并对其自由基伸长的抑制活性进行了评价。PI-28苯氧基部分苯环上含有3-Cl或4-Cl取代基的化合物比母体PI-28具有更强的活性。本文首次报道了芳基乙酰硫脲对根寄生杂草的防治作用,为根寄生杂草防治试剂的开发提供参考。
{"title":"The structure–activity relationship of aryloxyacetylthioureas for the inhibition of &lt;i&gt;Orobanche minor&lt;/i&gt; radicle elongation","authors":"Atsushi Okazawa, Shizuki Noda, Yusuke Mimura, Kotaro Fujino, Takatoshi Wakabayashi, Daisaku Ohta, Yukihiro Sugimoto, Motohiro Sonoda","doi":"10.1584/jpestics.d23-034","DOIUrl":"https://doi.org/10.1584/jpestics.d23-034","url":null,"abstract":"Orobanchaceae root parasitic weeds cause significant damage to agriculture and become threats to global food security. Integrated pest management is a key concept in modern agriculture and requires chemicals with various modes of action. Planteose accumulates as a storage carbohydrate in the dry seeds of root parasitic weeds. In Orobanche minor seeds, planteose is hydrolyzed by an α-galactosidase, OmAGAL2, during germination. It was found that the OmAGAL2 inhibitor, PI-28, suppressed the radicle elongation of germinating O. minor seeds. This inhibitory activity against O. minor radicle elongation was evaluated for a series of aryloxyacetylthioureas synthesized based on the structure of PI-28. Compounds with a 3-Cl or 4-Cl substituent on the benzene ring in the phenoxy moiety in PI-28 exhibited more potent activity than the parent PI-28. This is the first report on the effect of aryloxyacetylthioureas on a root parasitic weed and will contribute to the development of control reagents for root parasitic weeds.","PeriodicalId":16712,"journal":{"name":"Journal of Pesticide Science","volume":"50 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136304458","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
期刊
Journal of Pesticide Science
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