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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。
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引用次数: 0
A simulation model (PostPLANT-Soil) for predicting pesticide concentrations in succeeding leafy vegetables: II. Validation with experimental data on plant uptake in a growth chamber 预测后续叶菜中农药浓度的模拟模型(种后-土壤)[j]。用生长室内植物吸收的实验数据进行验证
4区 农林科学 Q2 ENTOMOLOGY Pub Date : 2023-01-01 DOI: 10.1584/jpestics.d23-007
Sayuri Namiki, Keiya Inao, Yutaka Motoki, Nobuyasu Seike, Eiki Watanabe
We validated a simulation model (PostPLANT-Soil) for predicting pesticide concentrations in succeeding leafy vegetables reported in our first paper in this series, which includes the pesticide sorption process into plant roots. As a result of the model validation with the measured data from a plant uptake study in a growth chamber, the model successfully simulated the concentration changes of pesticides in a plant shoot. However, the simulated shoot concentrations for several pesticides were overestimated compared to the measured values. The leafy vegetable (Brassica rapa) used in this study probably has a high metabolic ability for the fungicide flutolanil from the result of the uptake study under a hydroponic condition.
我们验证了一个模拟模型(PostPLANT-Soil),用于预测本系列第一篇论文中报道的后续叶类蔬菜中的农药浓度,其中包括农药在植物根系中的吸收过程。利用生长室内植物吸收研究的实测数据对模型进行验证,模型成功地模拟了植物枝条中农药浓度的变化。然而,与实测值相比,几种农药的模拟芽浓度被高估了。从水培条件下的吸收研究结果来看,本研究中使用的叶菜(Brassica rapa)可能对杀菌剂氟托拉尼具有较高的代谢能力。
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引用次数: 0
Fugacity model incorporating computational fluid dynamics for analyzing the behavior of an insecticide sprayed indoors 结合计算流体动力学的逸度模型用于分析室内喷洒杀虫剂的行为
4区 农林科学 Q2 ENTOMOLOGY Pub Date : 2023-01-01 DOI: 10.1584/jpestics.d23-011
Sayuri Tanaka, Yoshihide Matoba, Hiroaki Kondo, Tomohiko Ihara
Fugacity models are used widely to predict the time-dependent behaviors of chemicals in environments containing several media (e.g., air, sediment, soil, and water). However, these fugacity models work on the assumption that the concentration of a chemical in each medium is uniform, so they cannot describe the spatial distribution of the chemical. We developed a new fugacity model, termed InPestCFD, incorporating computational fluid dynamics to describe both the time-dependent distribution and the spatial distribution of a chemical in a medium. InPestCFD was used to calculate the behavior of an insecticide released from an aerosol canister in a room. Indoor airflow and aerosol particle behavior were calculated via computational fluid dynamics and using a Lagrangian dispersion model. Transport of the insecticide among media (aerosol particles, air, ceiling, floor, and walls) was calculated using the fugacity model. The time-dependent distributions and spatial distributions of the insecticide in the media agreed well with real measurements.
逸度模型被广泛用于预测化学物质在含有多种介质(如空气、沉积物、土壤和水)的环境中随时间变化的行为。然而,这些逸度模型是在假设每种介质中化学物质的浓度是均匀的前提下工作的,因此它们不能描述化学物质的空间分布。我们开发了一种新的逸度模型,称为InPestCFD,它结合了计算流体动力学来描述介质中化学物质的时间依赖性分布和空间分布。InPestCFD用于计算室内气溶胶罐中释放的杀虫剂的行为。通过计算流体力学和拉格朗日色散模型计算了室内气流和气溶胶颗粒的行为。使用逸度模型计算杀虫剂在介质(气溶胶颗粒、空气、天花板、地板和墙壁)之间的迁移。杀虫剂在介质中的时空分布与实测结果吻合较好。
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引用次数: 0
Discovery of a novel acaricide, acynonapyr 发现一种新的杀螨剂,无虫螨
4区 农林科学 Q2 ENTOMOLOGY Pub Date : 2023-01-01 DOI: 10.1584/jpestics.d23-028
Isami Hamamoto, Masahiro Kawaguchi, Takehiko Nakamura, Makio Yano, Keiji Koizumi, Jun Takahashi
Acynonapyr, discovered by Nippon Soda Co., Ltd., is a novel acaricide with N-pyridyloxy azabicycle as a unique core structure. Acynonapyr exhibits high activity against the spider mite species in the genera Tetranychus and Panonychus, with good efficacy at all life stages. Early in this research, cyclic amines substituted with (hetero)aryl(oxy) moieties were designed as target molecules and diversely synthesized, and 4-[4-(trifluoromethyl)phenoxy]-1-[5-(trifluoromethyl)-2-pyridyl]piperidine was found to show weak acaricidal activity. The structural optimization of this acaricidal active piperidine as the first lead compound led to the discovery of acynonapyr. In this report, our research process that led to the discovery of acynonapyr is described.
Acynonapyr是日本汽水公司发现的一种新型杀螨剂,其独特的核心结构为n -吡啶氧基氮杂二环。对叶螨属和全爪螨属的螨类均有较强的杀灭作用,且在各个生命阶段均有良好的杀灭效果。本研究早期以(杂)芳基(氧)基取代的环胺为靶分子,进行了多种合成,发现4-[4-(三氟甲基)苯氧基]-1-[5-(三氟甲基)-2-吡啶]哌啶具有较弱的杀螨活性。该杀螨活性胡椒碱作为第一个先导化合物进行结构优化,从而发现了刺虫精。在这篇报告中,我们的研究过程导致了acynonapyr的发现。
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引用次数: 0
Characteristics biological activities of the novel acaricide flupentiofenox against phytophagous mites 新型杀螨剂氟虫腈对植食性螨的生物学活性研究
4区 农林科学 Q2 ENTOMOLOGY Pub Date : 2023-01-01 DOI: 10.1584/jpestics.d23-033
Shingo Yoshimura, Shigeyuki Mukawa
Flupentiofenox, which has a unique chemical structure, is a novel acaricide that has been developed by the Kumiai Chemical Industry Co., Ltd. Flupentiofenox exerted significant acaricidal activities against spider mites Tetranychus urticae and Panonychus citri at all developmental stages even at extremely low concentrations, as compared with its practical concentration (80 ppm) for use in mites and was effective against spider mite populations that are resistant to widely used commercial acaricides. These results suggested that flupentiofenox could be used effectively for the control and prevention of spider mite infestation. Additionally, flupentiofenox had a more rapid effect than acetyl CoA carboxylase inhibitors, but it had a relatively slower effect than mitochondrial electron transport inhibitors and glutamate-gated chloride channel modulators. Overall, flupentiofenox is assumed to have a new mode of action.
fluupentiofenox是Kumiai化学工业有限公司开发的一种新型杀螨剂,具有独特的化学结构。与螨虫的实际使用浓度(80 ppm)相比,氟虫芬诺在所有发育阶段对荨叶螨和柑橘全爪螨都具有显著的杀螨活性,并且对对广泛使用的商业杀螨剂产生抗性的蜘蛛螨种群有效。结果表明,氟虱螨可有效防治蜘蛛螨的侵害。此外,氟哌啶芬诺比乙酰辅酶a羧化酶抑制剂起效更快,但比线粒体电子传递抑制剂和谷氨酸门控氯通道调节剂起效相对较慢。总的来说,fluupentiofenox被认为具有一种新的作用模式。
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引用次数: 0
A simple reliable quantification of glyphosate in human urine using MonoSpin TiO extraction and isotope dilution mass spectrometry 单旋钛萃取和同位素稀释质谱法测定人尿中草甘膦的简单可靠的定量
4区 农林科学 Q2 ENTOMOLOGY Pub Date : 2023-01-01 DOI: 10.1584/jpestics.d23-030
Takamitsu Otake, Keisuke Nakamura, Nobuyasu Hanari
A method of quantifying glyphosate (Gly) in human urine by means of MonoSpin TiO extraction and 9-fluorenylmethoxycarbonyl chloride (FMOC-Cl) derivatization with isotope dilution mass spectrometry (IDMS) was investigated and optimized. The method’s quantification limit under optimized conditions was 0.3 µg/kg for FMOC-Gly, which was comparable to or lower than those described in previous studies. When a spike test using human urine samples was carried out with optimized analytical conditions, the trueness for FMOC-Gly was as follows: 101.6–104.9% for a spike level of 0.5 µg/kg and 99.2–101.0% for a spike level of 30 µg/kg. The intra-day repeatability and inter-day reproducibility were <6.5%. The spike test results for validation between the “with” and “without” derivatization methods were comparable at 1 µg/kg. Our results indicate that using MonoSpin TiO extraction and FMOC-Cl derivatization with IDMS is an accurate method for analyzing Gly in human urine.
研究了单旋TiO萃取- 9-氟酰甲氧羰基氯(FMOC-Cl)衍生-同位素稀释质谱法(IDMS)测定人尿中草甘膦(Gly)含量的方法并进行了优化。优化条件下,FMOC-Gly的定量限为0.3µg/kg,与前人研究结果相当或更低。在优化的分析条件下,对人尿样品进行尖峰检测,FMOC-Gly的准确率为:尖峰水平为0.5µg/kg时为101.6 ~ 104.9%,尖峰水平为30µg/kg时为99.2 ~ 101.0%。日内重复性和日内重复性均<6.5%。“有”衍生化和“没有”衍生化方法之间验证的峰值测试结果在1µg/kg时具有可比性。本研究结果表明,单旋体TiO萃取和IDMS - FMOC-Cl衍生化是一种准确分析人尿中甘氨酸的方法。
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引用次数: 0
Basic Technology and Recent Trends in Agricultural Formulation and Application Technology. 农业配方与应用技术的基础技术与最新趋势。
IF 2.4 4区 农林科学 Q2 ENTOMOLOGY Pub Date : 2022-11-20 DOI: 10.1584/jpestics.D22-055
Takeo Ohkouchi, Kozo Tsuji

Recent requirements of the pesticide industry have become much severer, and pesticides (formulated products) are required to satisfy higher safety to both human beings and the environment, higher biological efficacy, lower price, and labor-saving. This review explains the outline of basic pesticide formulation technology, followed by recent advances in developing new formulations and application technologies. Labor-saving formulations and application technologies, environmental load reduction technologies, and user-friendly formulations and application technologies are elucidated.

近年来,农药行业对农药的要求越来越高,要求农药(配方产品)对人类和环境的安全性更高、生物功效更高、价格更低、更省力。本文概述了农药基本配方技术,并介绍了新配方的开发和应用技术的最新进展。阐述了省力配方及应用技术、环保减载技术、人性化配方及应用技术。
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引用次数: 1
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Journal of Pesticide Science
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