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Effect of further substitutions at 5-, 6-, 7-, or 8-position of 3-[3-(4-methoxyphenyl)-1-hydroxyprop-2-yl]coumarin on phytotoxicity. 3-[3-(4-甲氧基苯基)-1-羟基-2-基]香豆素在5-、6-、7-或8-位的进一步取代对植物毒性的影响。
IF 2.4 4区 农林科学 Q1 Agricultural and Biological Sciences Pub Date : 2023-08-20 DOI: 10.1584/jpestics.D23-016
Satoshi Yamauchi, Hazna Sartiva, Hisashi Nishiwaki

Derivatives of the coumarin ring in (R)-3-[3-(4-methoxyphenyl)-1-hydroxyprop-2-yl]coumarin 2, which is a lignan structure, were synthesized to clarify their structure-phytotoxicity relationships. The growth-inhibitory activity of the 8-OCH3 derivative 8 (IC50=228 µM) was more potent against the roots of lettuce seedlings than the compound without substituents 2. As for the roots of Italian ryegrass seedlings, the presence of the methoxy group at the 7- or 8-position was extremely effective for inhibiting growth (7-OCH3 7: IC50=121 µM, 8-OCH3 8: 56.7 µM). Methyl derivatives at the 5- or 8-position showed activity levels similar to those of the compound without substituents 2 (5-CH3 13: IC50=214 µM, 8-CH3 16: IC50=225 µM). The activities of OH- and F-derivatives were not observed or were lower.

合成了木脂素结构的(R)-3-[3-(4-甲氧基苯基)-1-羟基-2-基]香豆素2中香豆素环的衍生物,以阐明它们的结构-植物毒性关系。8-OCH3衍生物8的生长抑制活性(IC50=228 µM)比没有取代基的化合物2对莴苣幼苗的根更有效。对于意大利黑麦草幼苗的根,在7-或8-位存在甲氧基对抑制生长非常有效(7-OCH37:IC50=121 µM,8-OCH3 8:56.7 µM)。5-或8-位的甲基衍生物显示出与没有取代基2的化合物相似的活性水平(5-CH3 13:IC50=214 µM,8-CH3 16:IC50=225 µM)。OH-和F-衍生物的活性没有观察到或较低。
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引用次数: 0
Insect growth-regulating activity of 1-benzyl-2-methylbenzimidazole derivatives on silkworms. 1-苄基-2-甲基苯并咪唑衍生物对家蚕生长的调控作用。
IF 1.5 4区 农林科学 Q2 ENTOMOLOGY Pub Date : 2023-08-20 DOI: 10.1584/jpestics.D23-010
Shuhei Henmi, Ayumu Sueyoshi, Hiroshi Ono, Toshimasa Yamazaki, Konatsu Inoue, Takahiro Shiotsuki

Derivatives of 1-benzyl-2-methylbenzimidazoles (BMBIs) were synthesized to evaluate their biological activities against Bombyx mori, a lepidopteran model insect. Synthesized BMBIs exhibited two different biological activities: inhibition of development and acute lethality. From a structural perspective, the activity varied with the position of the substitutions on the 1-benzyl moiety; BMBIs with substitutions on the 2 and/or 4 positions had comparatively high activity in comparison with those with substitutions on the 3-position. There was more activity for the inhibition of development with low doses, and more for acute lethality with high doses. The activity was also affected by the applied stage, that is, application in the 4th instar mostly interfered the larval molting or pupation, whereas that in the 3rd instar caused more acute mortality. Taken together, these results suggest that BMBIs have multiple modes of action.

合成了1-苄基-2-甲基苯并咪唑衍生物(BMBIs),以评价其对鳞翅目模式昆虫家蚕的生物活性。合成的BMBI表现出两种不同的生物活性:抑制发育和急性致死。从结构角度来看,活性随着1-苄基部分上取代的位置而变化;在2和/或4位上具有取代的BMBI与在3位上具有替代的BMBI相比具有相对高的活性。低剂量对发育的抑制作用更强,高剂量对急性致死作用更强。该活性也受到施用阶段的影响,即4龄的施用主要干扰幼虫的蜕皮或化蛹,而3龄的施用则导致更严重的死亡率。总之,这些结果表明BMBI具有多种作用模式。
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引用次数: 0
Syntheses of (+)-costic acid and structurally related eudesmane sesquiterpenoids and their biological evaluations as acaricidal agents against Varroa destructor. (+)-costic acid和结构相关的真结烷倍半萜类化合物的合成及其作为灭螨剂的生物学评价。
IF 2.4 4区 农林科学 Q1 Agricultural and Biological Sciences Pub Date : 2023-08-20 DOI: 10.1584/jpestics.D23-029
Kenji Nemoto, Hirosato Takikawa, Yusuke Ogura

Synthesis of (+)-costic acid, isolated from Dittrichia viscosa (L.) W. Greuter as a natural acaricidal sesquiterpenoid, was achieved in 16 steps from (R)-carvone with an overall yield of 4.8%, involving the radical cyclization of selenoester to construct a decalone framework as the key step. Other structurally related natural products, (+)-costal, (+)-costol, and (+)-β-selinene, were also synthesized. The acaricidal activities of these four natural products and some synthetic intermediates were also evaluated against Varroa destructor. Among them, (+)-costal especially exhibited potent acaricidal activity.

以(R)-香芹酮为原料,经16步反应合成了从粘氏Ditrichia viscosa(L.)W.Greuter中分离的天然杀螨倍半萜类化合物(+)-costic acid,总收率4.8%,关键步骤是硒醚的自由基环化以构建十氢萘骨架。还合成了其他结构相关的天然产物,(+)-costal、(+)-costol和(+)β-selinene。还对这四种天然产物和一些合成中间体的杀螨活性进行了评价。其中(+)-costal表现出较强的杀螨活性。
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引用次数: 0
Production of copper nanoparticle-immobilized chitin nanofibers and their role in plant disease control. 铜纳米粒子固定化甲壳素纳米纤维的制备及其在植物病害控制中的作用。
IF 2.4 4区 农林科学 Q1 Agricultural and Biological Sciences Pub Date : 2023-08-20 DOI: 10.1584/jpestics.D23-001
Mayumi Egusa, Shunki Watanabe, Hujun Li, Dagmawi Abebe Zewude, Shinsuke Ifuku, Hironori Kaminaka

Chitin is used in agriculture to improve crop production; however, its use is limited due to difficulties in its handling. A chitin nanofiber (CNF) overcomes this issue and, due to its elicitor activity, has great potential for crop protection. To expand CNF utilization, a copper nanoparticles-based antimicrobic CNF (CuNPs/CNF) was prepared using a chemical reduction method. The formation of CuNPs was confirmed via scanning electron microscopy. Thermogravimetric analysis revealed that the amount of CuNPs on the CNF was dose-dependent on the precursor salt, copper acetate. CuNPs endowed the CNF with strong antimicrobial activity against Alternaria brassicicola and Pectobacterium carotovorum. Moreover, the CuNPs/CNF reduced pathogen infection in cabbage. The antimicrobial activity and disease prevention of the CuNPs/CNF was increased compared to the corresponding CNF or commercial agrochemical Bordeaux treatment. These results indicate that CuNPs conferred antimicrobial activity on the CNF and increased the efficacy of plant disease protection.

甲壳素被用于农业以提高作物产量;然而,由于处理困难,其使用受到限制。甲壳素纳米纤维(CNF)克服了这一问题,并且由于其诱导子活性,在作物保护方面具有巨大的潜力。为了扩大CNF的利用率,使用化学还原方法制备了基于铜纳米颗粒的抗微生物CNF(CuNPs/CNF)。通过扫描电子显微镜证实了CuNPs的形成。热重分析显示,CNF上的CuNP的量与前体盐醋酸铜呈剂量依赖关系。CuNPs赋予CNF对brassicicola链格孢菌和carotovorum乳杆菌具有较强的抗菌活性。此外,CuNPs/CNF降低了卷心菜的病原体感染。与相应的CNF或商业化农药波尔多处理相比,CuNPs/CNF的抗菌活性和疾病预防作用有所提高。这些结果表明,CuNPs赋予CNF抗菌活性,并提高了植物病害保护的功效。
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引用次数: 0
Production of desmethyl-gregatin A, a possible causative toxin of brown stem rot in adzuki bean, by Phialophora gregata f. sp. adzukicola. 小豆褐茎腐病可能的致病毒素去甲基gregatin A的产生。
IF 2.4 4区 农林科学 Q1 Agricultural and Biological Sciences Pub Date : 2023-05-20 DOI: 10.1584/jpestics.D22-070
Moe Aizawa, Hayate Saito, Takuya Mitazaki, Takara Taketani, Keiichi Noguchi, Sho Miyazaki, Hiroshi Kawaide, Masahiro Natsume

To elucidate the cause of brown stem rot in the adzuki bean, we re-evaluated the phytotoxins produced in cultures of the causative agent, Phialophora gregata f. sp. adzukicola. The ethyl acetate-soluble acidic fraction of the culture, as well as the neutral fraction, inhibited the growth of alfalfa seedlings. In the neutral fraction, known phytotoxins gregatin A, B, and C or D and penicilliol A were present. Although the phytotoxins in the acidic fraction were unstable, liquid chromatography-mass spectrometry analysis of the partially purified material suggested that one phytotoxin present was the non-methylated gregatin desmethyl-gregatin A (gregatinic acid A).

为了阐明小豆褐色茎腐病的原因,我们重新评估了病原菌phalophora gregata f. sp. adzukicola培养物中产生的植物毒素。乙酸乙酯可溶性酸性部分和中性部分抑制了苜蓿幼苗的生长。在中性部分中,存在已知的植物毒素gregatin A, B和C或D和青霉醇A。虽然酸性部分中的植物毒素不稳定,但液相色谱-质谱分析部分纯化的物质表明,其中一种植物毒素是未甲基化的gregatin去甲基-gregatin A (gregatin acid A)。
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引用次数: 0
Metagenomic analysis of ready biodegradability tests to ascertain the relationship between microbiota and the biodegradability of test chemicals. 对现成的生物降解性试验进行元基因组分析,以确定微生物群与试验化学品的生物降解性之间的关系。
IF 1.5 4区 农林科学 Q2 ENTOMOLOGY Pub Date : 2023-05-20 DOI: 10.1584/jpestics.D22-067
Yoshinari Takano, Saki Takekoshi, Kotaro Takano, Yoshihide Matoba, Makiko Mukumoto, Osamu Shirai

Ready biodegradability tests conducted in accordance with the Organisation for Economic Co-operation and Development guidelines (test 301C or test 301F) are performed using activated sludge (AS) prepared by the Chemicals Evaluation and Research Institute (AS-CERI) or that taken from a sewage treatment plant (AS-STP). It had been reported that AS-CERI had lower activity than AS-STP in biodegrading test chemicals, and that biodegradation was accelerated by increasing the volume of the test medium. However, these phenomena have not been clarified from the perspective of the microbiota. In this study, using metagenomic analysis, we first showed that the microbiota of AS-CERI was biased in its distribution of phyla, less diverse, and had greater lot-to-lot variability than that of AS-STP. Second, after cultivation for a long period of time, the microbiota of AS-STP and AS-CERI became more similar to each other in terms of community structure. Third, determining degraders of test substances when each substance was actively biodegraded was found to be an effective approach. Finally, we clarified experimentally that a large volume of test medium increased the number of species that could degrade test substances in the condition where the initial concentrations of each substance and AS-STP were kept constant.

根据经济合作与发展组织准则(试验 301C 或试验 301F)进行的即用生物降解性试验,使用的是化学品评估和研究所(AS-CERI)制备的活性污泥(AS)或从污水处理厂提取的活性污泥(AS-STP)。据报道,AS-CERI 在生物降解测试化学品方面的活性低于 AS-STP,而且生物降解会随着测试介质体积的增加而加快。然而,这些现象尚未从微生物群的角度得到澄清。在本研究中,我们首先利用元基因组分析表明,与 AS-STP 相比,AS-CERI 的微生物区系在门类分布上存在偏差,多样性较低,批次间的变异性较大。其次,经过长期培养后,AS-STP 和 AS-CERI 的微生物群在群落结构上变得更加相似。第三,我们发现在每种物质被积极生物降解时测定其降解者是一种有效的方法。最后,我们通过实验证明,在每种物质和 AS-STP 的初始浓度保持不变的情况下,大量的试验培养基增加了能够降解试验物质的物种数量。
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引用次数: 0
Effectiveness of Cordyceps fumosorosea Wettable Powder Formulation against Metisa plana (Walker) and Its Side Effects on Elaeidobius kamerunicus in Oil palm Plantation. 冬虫夏草可湿性粉剂对油棕田斑螨的防治效果及对卡美尼比斯的毒副作用。
IF 2.4 4区 农林科学 Q1 Agricultural and Biological Sciences Pub Date : 2023-05-20 DOI: 10.1584/jpestics.D22-072
Ashraf Arif Nasir, Nurul Yaqin Syarif, Dzolkhifli Omar, Norhayu Asib

Development of mycoinsecticides with Cordyceps fumosorosea as an active ingredient is established as an alternate way to control the Metisa plana population while reducing chemical insecticide dependence. Three mycoinsecticide formulations (SS6, SS7, and SS8) with dispersing and wetting agents were developed as wettable powder formulations in this trial. SS8 demonstrated the best wettability, suspensibility, and dispersibility with viability at 107 (CFU)/mL even after three months of storage. However, SS7 developed with C. fumosorosea as an active ingredient was found to effectively reduce the bagworm population by more than 95%. The application of all mycoinsecticide formulations in the infested oil palm area was able to reduce the M. plana population by more than 95%, 30 DAT. The formulations also show no significant increase in mortality of the oil palm pollinator, Elaeidobius kamerunicus. This finding indicates that the C. fumosorosea tested has potential for managing bagworms without harming pollinators on oil palm plantations.

以冬虫夏草为有效成分的真菌杀虫剂的开发是控制梅沙种群的另一种方法,同时减少对化学杀虫剂的依赖。本试验研制了含有分散剂和润湿剂的3种真菌杀虫剂制剂(SS6、SS7和SS8)作为可湿性粉剂。SS8表现出最好的润湿性、悬浮性和分散性,即使在储存3个月后,其活力也保持在107 (CFU)/mL。以烟孢梭菌为有效成分开发的SS7可有效减少95%以上的蛴螬。在受感染的油棕区使用所有真菌杀虫剂制剂,可使平面支原体种群减少95%以上。这些配方也没有显著增加油棕传粉者的死亡率,Elaeidobius kamerunicus。这一发现表明,所测试的C. fumosorosea具有在不伤害油棕种植园传粉者的情况下管理袋虫的潜力。
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引用次数: 0
Cycloprop-2-ene-1-carboxylates: Potential chemical biology tools in the early growth stage of Arabidopsis thaliana. 环丙-2-烯-1-羧酸盐:拟南芥生长早期潜在的化学生物学工具。
IF 2.4 4区 农林科学 Q1 Agricultural and Biological Sciences Pub Date : 2023-05-20 DOI: 10.1584/jpestics.D22-034
Tomoyuki Koyama, Ikuo Takahashi, Tadao Asami

Cyclopropene derivatives have been used as extremely reactive units in organic chemistry owing to their high ring-strain energy. They have become popular reagents both for bioorthogonal chemistry and for chemical biology because of their small size and ability to be genetically encoded. In this context, we conducted an exploratory study to identify the biologically active cyclopropenes that affect normal plant growth. We synthesized several cycloprop-2-ene-1-carboxylic acid derivatives and evaluated their effects on the early growth stage of Arabidopsis thaliana. Eventually, we identified the chemicals that affect apical hook development in Arabidopsis thaliana. Their mode of action is different from those of ethylene receptor inhibition and gibberellin biosynthesis inhibition. We expect that some of the chemicals reported here can be new tools in chemical biology to determine useful molecular targets for herbicides or plant growth regulators.

环丙烯衍生物由于具有较高的环应变能,在有机化学中被用作极活泼的单元。由于它们体积小且能够进行基因编码,它们已成为生物正交化学和化学生物学的热门试剂。在此背景下,我们进行了一项探索性研究,以确定影响正常植物生长的生物活性环丙烯。合成了几种环丙-2-烯-1-羧酸衍生物,并评价了它们对拟南芥生长早期的影响。最终,我们确定了影响拟南芥顶端钩发育的化学物质。它们的作用方式不同于乙烯受体抑制和赤霉素生物合成抑制。我们期望这里报道的一些化学物质可以成为化学生物学的新工具,以确定除草剂或植物生长调节剂的有用分子靶点。
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引用次数: 0
Fungicidal spectrum and biological properties of a new fungicide, pyriofenone. 新型杀菌剂吡虫酮的杀菌谱及生物学特性。
IF 2.4 4区 农林科学 Q1 Agricultural and Biological Sciences Pub Date : 2023-05-20 DOI: 10.1584/jpestics.D22-068
Munekazu Ogawa, Akihiro Nishimura, Yuzuka Abe, Yohei Fukumori, Kazumi Suzuki, Shigeru Mitani

Pyriofenone is a new fungicide developed by Ishihara Sangyo Kaisha, Ltd. To determine the fungicidal spectrum of pyriofenone, in vivo pot tests and in vitro mycelial growth-inhibition tests were conducted. Pyriofenone showed excellent activity against wheat and cucumber powdery mildew and moderate efficacy against rice blast in the pot tests. In the mycelial growth-inhibition tests, most fungi were not affected by pyriofenone except for Botrytis cinerea, Helminthosporium sacchari, Pseudocercosporella herpotrichoides, Pyricularia oryzae, Rosellinia necatrix, and Verticillium dahliae. The fungicidal properties of pyriofenone on powdery mildew in cucumber and wheat were evaluated precisely. Pyriofenone exhibited excellent preventive and residual activities. It had high rainfastness in the cucumber leaves against powdery mildew. Pyriofenone also showed inhibitory activity on lesion development upon application until 2 days after inoculation, and the lesion expansion and sporulation of the cucumber powdery mildew fungus were effectively controlled. Furthermore, pyriofenone showed translaminar and vapor activities.

Pyriofenone是石原Sangyo Kaisha株式会社开发的一种新型杀菌剂。通过体内盆栽试验和体外菌丝生长抑制试验确定吡虫酮的抑菌谱。在盆栽试验中,吡虫酮对小麦和黄瓜白粉病表现出优异的防治效果,对稻瘟病表现出中等的防治效果。在菌丝体生长抑制试验中,除灰葡萄孢、糖化蠕虫孢、蛇尾假孢子菌、稻瘟病菌、桃红玫瑰菌和大丽花黄萎病菌外,大多数真菌不受嘧菌酮的影响。对吡虫酮对黄瓜和小麦白粉病的杀灭性能进行了精确评价。吡虫酮具有良好的预防和残留活性。对黄瓜叶片抗白粉病有较高的耐雨性。在接种后2 d内,吡虫酮对黄瓜白粉病菌的病变发展也有抑制作用,有效地控制了黄瓜白粉病菌的病变扩大和产孢。此外,吡喃酮具有跨层流和水蒸气活性。
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引用次数: 0
Visualization of azoxystrobin penetration in wheat leaves using mass microscopy imaging. 利用质显微成像技术可视化小麦叶片中偶氮嘧菌酯的渗透。
IF 2.4 4区 农林科学 Q1 Agricultural and Biological Sciences Pub Date : 2023-05-20 DOI: 10.1584/jpestics.D22-063
Soichiro Ikuta, Eiichiro Fukusaki, Shuichi Shimma

Fungicides must penetrate the internal tissues of plants to kill pathogenic fungi. Mass spectrometers have been used to confirm this penetration, but conventional mass spectrometric methods cannot distinguish the fungicides in different internal tissues owing to the extraction steps. However, matrix-assisted laser desorption/ionization mass spectrometry imaging (MALDI-MSI) can detect the penetration of fungicides into leaf sections through direct analysis of the sample surfaces. Therefore, the objective of this study was to establish a method for visualizing fungicide penetration in wheat leaf cross sections using MALDI-MSI. The penetration of azoxystrobin from the epidermal to the internal tissue of the leaves was observed. Moreover, azoxystrobin accumulates in the cells around the vascular bundle. This study suggests that MSI can be useful for the evaluation of fungicide penetration in plant leaves.

杀菌剂必须渗透到植物的内部组织才能杀死致病真菌。质谱已被用来证实这种渗透,但由于提取步骤的原因,传统的质谱方法无法区分不同内部组织中的杀菌剂。然而,基质辅助激光解吸/电离质谱成像(MALDI-MSI)可以通过直接分析样品表面来检测杀菌剂对叶片的渗透。因此,本研究的目的是建立一种利用MALDI-MSI可视化小麦叶片横截面杀菌剂渗透的方法。观察到氮嘧菌酯从表皮渗透到叶片内部组织。此外,偶氮氧嘧啶在维管束周围的细胞中积累。本研究表明,MSI可用于评价杀菌剂在植物叶片中的渗透。
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引用次数: 0
期刊
Journal of Pesticide Science
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