Journal of Pesticide Science

Original Articles

ヘテロ芳香族カルボン酸アミドにおける位置異性体の構造と活性の関係

番場伸一, 吉川幸宏, 勝田裕之

2013 年 38 巻 3 号 p. 91-95
発行日: 2013/08/20
公開日: 2013/08/27
[早期公開] 公開日: 2013/08/15

DOIhttps://doi.org/10.1584/jpestics.D12-010

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Positional isomers of various aromatic heterocyclic carboxamides were synthesized and their fungicidal activity was examined. Among them, N-(biphenyl-2-yl) and N-[2-(1,3-dimethylbutyl)-3-thienyl]-1-methyl-3-CF₃-pyrazole-4-carboxamides showed high activity against gray mold, while their corresponding 5-CF₃ carboxamide isomers showed no fungicidal activity. Similar results were observed for carboxamide isomers containing CF₃-thiazole as well as methyl-substituted thiophene and furan derivatives. Docking studies were performed on these carboxamides with a fungus succinate dehydrogenase homology model. Based on our docking study, we proposed a model for the interaction between carboxamides and a conserved histidine residue in succinate dehydrogenase.

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新規殺菌剤リードとして有用な3-置換オキシ-5-メチルイソキサゾール誘導体

三宅泰司, 矢ケ崎有希, 中島健一郎, 利部伸三

2013 年 38 巻 3 号 p. 96-104
発行日: 2013/08/20
公開日: 2013/08/25
[早期公開] 公開日: 2013/08/14

DOIhttps://doi.org/10.1584/jpestics.D12-028

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The structure of the commercial fungicide hymexazol, 3-hydroxy-5-methylisoxazol, was transformed to acyloxy, 3-alkoxy, alkylcarbamoyloxy and acylamino derivatives, and their antifungal activities or disease control activities were examined. The 3-acyloxy derivatives were much more active than the other derivatives, and some of the 3-acyloxy derivatives exhibited antifungal activities or disease control activities against a wide range of pathogens, such as Pyrenophora graminea, Alternaria alternata, Cercospora beticola, Rhynchosporium secalis, Septoria tritici, Microdochium nivale, Rhizoctonia solani, Puccinia recondita, and Blumeria graminis. Among them, 5-methyl-3-isoxazolyl (α)-naphthoate and (o)-toluate and 2,2-dichloro-1,3,3-trimethylcyclopropanecarboxylate completely inhibited the mycelial growth of Rhizoctonia solani and M. nivale at 25 mg/L, respectively.

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熱ストレスを受けたイネ花粉の発芽に及ぼすブラシノステロイドとエクジステロイドの効果

Jutiporn Thussagunpanit, Kanapol Jutamanee, Lily Kaveeta, Witith Chai- ...

2013 年 38 巻 3 号 p. 105-111
発行日: 2013/08/20
公開日: 2013/08/25
[早期公開] 公開日: 2013/08/14

DOIhttps://doi.org/10.1584/jpestics.D13-029

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Heat stress is associated with a reduction in pollen germination and seed setting of rice. Brassinosteroids have been reported to counteract some stresses on plant growth and development. We investigated the effects of an exogenously applied brassinosteroid, (24-epibrassinolide; EBR) and an ecdysone analogue (7,8-dihydro-8α-20-hydroxyecdysone; DHECD) against heat stress on pollen viability of rice (Oryza sativa L.) cv. Pathum Thani 1. The plants were treated with either EBR or DHECD and exposed to a day/night heat stress regime of 40/30°C for 7 days. The results demonstrated that 0.001 µM of either chemical was effective for increasing pollen viability and reducing pollen bursting. Furthermore, these chemical treatments conferred resistance to heat stress in in vivo pollen germination and seed setting. Consequently, these results suggest EBR and DHECD should alleviate the detrimental effects of heat stress by improving pollen germination and seed setting and enable rice to withstand high temperature stress.

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薬物排出に関わるP-糖タンパク質の基質認識機構：さまざまな化学物質および農薬の構造とATPase活性との関係

金岡怜志, 木村泰久, 藤川真章, 中川好秋, 植田和光, 赤松美紀

2013 年 38 巻 3 号 p. 112-122
発行日: 2013/08/20
公開日: 2013/08/26
[早期公開] 公開日: 2013/08/14

DOIhttps://doi.org/10.1584/jpestics.D13-022

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P-glycoprotein (P-gp) is a member of the ATP-binding cassette transporter family. It actively transports a wide variety of compounds out of cells and functions as an energy-dependent efflux pump to protect humans from xenobiotics. P-gp also plays an important role in multidrug resistance in the treatment of cancers. However, the mechanism of P-gp substrate recognition is complicated and still poorly understood. In this study, we screened diverse chemicals, especially agrochemicals by measuring the ATPase activity of human P-gp and found that several classes of chemicals including dibenzoylhydrazine (DBH) insecticides could be substrates of P-gp. ATPase activity was quantitatively analyzed using a 3D quantitative structure-activity relationship, comparative molecular field analysis (CoMFA), and the favorable and unfavorable properties of ligands for ATPase activity were clarified. We also performed a docking simulation of a DBH-type compound with P-gp to predict the binding mode, which was supported by the CoMFA results.

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新規メタジアミド殺虫化合物と一般的な非競合的アンタゴニストのハスモンヨトウRDL GABA受容体に対する作用機作の比較

中尾俊史, 平瀬寒月

2013 年 38 巻 3 号 p. 123-128
発行日: 2013/08/20
公開日: 2013/08/25
[早期公開] 公開日: 2013/08/14

DOIhttps://doi.org/10.1584/jpestics.D13-024

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Novel meta-diamides [3-benzamido-N-(4-(perfluoropropan-2-yl)phenyl)benzamides] are a distinct class of RDL GABA receptor antagonists with high larvicidal activity against Spodoptera litura. Genotyping showed that the S. litura RDL GABA receptor subunit (SL-RDL) gene had Ser at its 2′ position, which was widely distributed among field S. litura larvae in Japan. We investigated the modes of action of meta-diamides on SL-RDLbd homomers using a membrane potential assay. S2′N and T6′V mutations had profound effects on the inhibitory activities of fipronil and α-endosulfan, whereas these mutations had no effect on the inhibitory activities of meta-diamides. In contrast, a G319M mutation abolished the inhibitory activities of meta-diamides, whereas it had only a small effect on the activities of fipronil and α-endosulfan. These results suggest that the site of action of meta-diamides is near G319 in the third transmembrane segment of SL-RDL homomers, which is distinct from those of fipronil and α-endosulfan.

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地上ブームスプレーヤーにおける農薬のドリフトと沈着を予測するためのOML-スプレードリフトモデル

Per Løfstrøm, Marianne Bruus, Helle Vibeke Andersen, Christian Kjær, D ...

2013 年 38 巻 3 号 p. 129-138
発行日: 2013/08/20
公開日: 2013/08/30
[早期公開] 公開日: 2013/08/28

DOIhttps://doi.org/10.1584/jpestics.D12-064

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In order to predict the exposure of hedgerows and other neighboring biotopes to pesticides from field-spray applications, an existing Gaussian atmospheric dispersion and deposition model was developed to model the changes in droplet size due to evaporation affecting the deposition velocity. The Gaussian tilting plume principle was applied inside the stayed track. The model was developed on one set of field experiments using a flat-fan nozzle and validated against another set of field experiments using an air-induction nozzle. The vertical spray-drift profile was measured using hair curlers at increasing distances. The vertical concentration profile downwind has a maximum just above the ground in our observations and calculations. The model accounts for the meteorological conditions, droplet ejection velocity and size spectrum. Model validation led to an R² value of 0.78, and 91% of the calculated drift values were within a factor of four of the measurements.

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Notes

Stenotrophomonas maltophilia CGMCC 1.1788の前処理によるイミダクロプリド殺アリマキ活性の増強

Zhonghua Liu, Yumin Cao, Yijun Dai, Jueping Ni, Hua Wei, Sheng Yuan

2013 年 38 巻 3 号 p. 139-143
発行日: 2013/08/20
公開日: 2013/08/27
[早期公開] 公開日: 2013/08/15

DOIhttps://doi.org/10.1584/jpestics.D13-010

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When imidacloprid was first pretreated in a solution of Stenotrophomonas maltophilia CGMCC 1.1788 in the presence of succinate for 8 days and then applied directly to soils, its aphicidal activity was raised more than twofolds. Analysis explored that a part of imidacloprid was cometabolically biotransformed to highly active metabolites. This paper offers a new, economical way to apply bacterial transformation to improve insecticidal activity, which can decrease the dosage of imidacloprid and reduce environmental residue caused by insecticides.

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ビールおよび麦芽中におけるパラコートとジクワットのLC-MS/MSによる迅速分析法

永富康司, 吉岡俊暁, 柳沢真由美, 宇山敦生, 望月直樹

2013 年 38 巻 3 号 p. 144-146
発行日: 2013/08/20
公開日: 2013/08/27
[早期公開] 公開日: 2013/08/14

DOIhttps://doi.org/10.1584/jpestics.D13-008

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Paraquat and diquat are fast-acting herbicides that have been used worldwide. While they might pose food safety risks, their extremely basic and polar properties make it difficult to sensitively analyze these herbicides in food components. In the present study, a rapid and sensitive analysis (LOQ=10 µg/kg) of beer and malt samples using LC-MS/MS was performed under ion pair chromatography conditions. Samples were prepared by extraction with dilute HCl and purification with a weak cation exchange SPE cartridge.

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テブコナゾール誘導体は強力なストリゴラクトン生合成阻害剤である

伊藤晋作, 梅原三貴久, 花田篤志, 山口信次郎, 浅見忠男

2013 年 38 巻 3 号 p. 147-151
発行日: 2013/08/20
公開日: 2013/08/27
[早期公開] 公開日: 2013/08/14

DOIhttps://doi.org/10.1584/jpestics.D13-011

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To find strigolactone (SL) biosynthesis inhibitors, we screened the azole-containing chemicals that reduce the level of 2′-epi-5-deoxystrigol (epi-5DS) in rice. As a result of the screening, tebuconazole, a known fungicide targeting ergosterol biosynthesis, was selected as a potent SL biosynthesis inhibitor. A structure-activity relationship study of tebuconazole was carried out to discover more potent SL biosynthesis inhibitors. By evaluating the inhibitory activity on epi-5DS biosynthesis, we found that 2-(2-chlorophenyl)-4-(4-chlorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (4b) and 4-(4-chlorophenyl)-2-(4-phenoxyphenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (4e) showed potent ability to reduce epi-5DS biosynthesis.

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除草剤ピロキサスルホンのコムギおよびボウムギ幼苗間の択性に関わる代謝の役割

種谷良貴, 池田光政, 角康一郎, 清水力, 松本宏

2013 年 38 巻 3 号 p. 152-156
発行日: 2013/08/20
公開日: 2013/08/25
[早期公開] 公開日: 2013/08/14

DOIhttps://doi.org/10.1584/jpestics.D13-014

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Metabolism of pyroxasulfone in a tolerant crop, wheat and a susceptible plant, rigid ryegrass, was studied using ¹⁴C-pyroxasulfone. The main metabolites were a cysteine conjugate of the isoxazoline ring (M-26), deaminated M-26 (M-29) and a glucose conjugate of M-29, suggesting that the main metabolic route in both plants was the cleavage of the methylenesulfonyl linkage caused by glutathione conjugation. The difference in the metabolic activity was assumed to be one of the factors in determining the selectivity of pyroxasulfone between wheat and rigid ryegrass.

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PCR-RFLP法を用いたフィプロニル抵抗性ウンカ類のGABA受容体RDLサブユニットのA2′N変異の検出

中尾俊史, 平瀬寒月

2013 年 38 巻 3 号 p. 157-160
発行日: 2013/08/20
公開日: 2013/08/25
[早期公開] 公開日: 2013/08/14

DOIhttps://doi.org/10.1584/jpestics.D13-028

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Sogatella furcifera and Laodelphax striatellus are serious pests of rice plants that have developed fipronil resistance in Asia. The A2′N mutation in the RDL γ-aminobutyric acid (GABA) receptors conferred fipronil resistance and was suggested to be a heterozygous mutation. We have developed a rapid PCR-RFLP assay to detect the A2′N mutation in individual insects. This assay is useful for monitoring S. furcifera and L. striatellus carrying the A2′N mutation in field populations and may contribute to managing these pests.

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Society Awards 2013

農薬補助剤のライフサイクルに関与する環境微生物の分子生態学的研究

堀田雄大

2013 年 38 巻 3 号 p. 161-163
発行日: 2013/08/20
公開日: 2013/08/25
[早期公開] 公開日: 2013/08/14

DOIhttps://doi.org/10.1584/jpestics.J13-02

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The life cycle impact assessment of chemicals in the environment is essential for establishing an environmentally conscious, material-recycling society. To understand the life cycle of chemicals through the environmental problems arising from the alkylphenol polyethoxylate (APEO_n) issue, our research has focused as follows; (1) clarification of environmental fate based on interaction between bacteria and environmental factors; (2) establishment of a rapid and simple bacterial identification method. Environmental elements, such as Ca²⁺, Mg²⁺ and Fe³⁺, may influence the activity and rate of APEO_n biodegradation in the environment. A highly reliable method for phylogenetic analysis at the strain level, named the S10-GERMS (S10-spc-alpha operon gene encoded ribosomal protein mass spectrum) method, was developed using bacterial ribosomal subunit proteins as theoretical biomarkers encoded in the S10-spc-alpha operon with a validation procedure.

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蛍光分光法を用いたフェンバレレートの光励起ラジカル検出に関する研究

鈴木祐介

2013 年 38 巻 3 号 p. 164-166
発行日: 2013/08/20
公開日: 2013/08/25
[早期公開] 公開日: 2013/08/14

DOIhttps://doi.org/10.1584/jpestics.J13-03

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A novel approach to detect short-lived free radicals was investigated by combining a radical-trapping technique with highly sensitive and selective fluorescence spectroscopy. The generated benzyl radicals formed via homolytic cleavage of the ester linkage by photochemical decarboxylation of fenvalerate could be trapped by a nitroxide spin label possessing a primary amino group. The instantaneous and quantitative reaction of the resultant trapping adducts with fluorescamine, a specific fluorescent probe precursor for a primary amino compound, formed the highly fluorescent derivatives suitable for fluorescence-detection HPLC. The chemical structures of the fluorescence derivatives were identified by LC/MS spectrometry.

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新規殺菌剤「ペンチオピラド」の研究開発

柳瀬勇次, 勝田裕之, 冨谷完治, 榎本幹, 坂本修

2013 年 38 巻 3 号 p. 167-168
発行日: 2013/08/20
公開日: 2013/08/25
[早期公開] 公開日: 2013/08/14

DOIhttps://doi.org/10.1584/jpestics.J13-01

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Penthiopyrad is a novel fungicide belonging to the carboxamide group. This compound was discovered by Mitsui Chemicals Agro, Inc., and launched in Japan in 2010 under the trade name Affet® SC in the fruit and the vegetable market and in 2009 under the name Gaia® WDG in the turf market. Penthiopyrad has broad antifungal spectrum of not only Basidiomycetes but also Ascomycetes and Deuteromycetes, and as a result, the broad antifungal spectrum contributes to its excellent ability to control various kinds of diseases on important crops in one treatment.

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農作物中の残留農薬濃度に関する変動要因の評価

藤田眞弘, 飯島和昭

2013 年 38 巻 3 号 p. 169-170
発行日: 2013/08/20
公開日: 2013/08/25
[早期公開] 公開日: 2013/08/14

DOIhttps://doi.org/10.1584/jpestics.J13-04

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To evaluate the various factors affecting pesticide residue levels in Japanese raw agricultural commodities (RACs), acetamiprid and cypermethrin residues in apple, broccoli, cabbage, grape, and sweet pepper samples were investigated. The individual variations of pesticide residue levels in apples were greater than other factors, such as field-to-field variations and separate analyses of edible and inedible portions. The results from various RACs indicate that differences in the distributions of the two pesticides might be due to the influence of various factors, such as differences in crop species, plant cultivation methods, and physicochemical properties of the pesticides. The statistical results indicate that a sufficient sampling size is required to obtain accurate analytical results. This study provided valuable information on estimating variations in pesticide residue levels in RACs in accordance with Japanese common agricultural practices.

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新規水稲除草剤「ピリミスルファン」の研究開発

吉村巧, 池内利祐, 大野修二, 朝倉草平, 濱田祐介

2013 年 38 巻 3 号 p. 171-172
発行日: 2013/08/20
公開日: 2013/08/25
[早期公開] 公開日: 2013/08/14

DOIhttps://doi.org/10.1584/jpestics.J13-05

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Pyrimisulfan is a novel paddy herbicide that was discovered and developed by Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.; and K-I Chemical Research Institute Co., Ltd. It was registered in Japan in 2010 and launched the first one-shot herbicide containing only one active ingredient (a.i.) developed with our original formulation technology. The compound is sulfonanilide, having a pyrimidinyl-containing group at the 2′-position and an acetolactate synthase (ALS) inhibitor. Pyrimisulfan shows broad-spectrum weed control against annual grass, sedge, broadleaf, and sulfonylurea-resistant weeds without causing phytotoxic injury to rice. At doses of 50–75 g a.i./ha, pyrimisulfan has a wide application window and exhibits long residual activity against these weeds. Pyrimisulfan has favorable toxicological, ecotoxicological, and environmental profiles.

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