{"title":"Quantitative structure–activity relationship of 2,6-dimethoxy-N-(3-(4-substituted phenyl)isoxazol-5-yl)benzamide for the inhibition of chitin synthesis","authors":"Kotaro Mori, Masahiro Miyashita, Soichirou Mori, Norio Shibata, Yoshiaki Nakagawa","doi":"10.1584/jpestics.d24-004","DOIUrl":"https://doi.org/10.1584/jpestics.d24-004","url":null,"abstract":"</p><p>Previously, we found that 5-(2,6-dimethoxybenzoylamino)-3-phenylisoxazoles (IOXs) inhibit chitin synthesis in the cultured integument of <i>Chilo suppressalis</i>. In this study, IOXs with various substituents at the <i>para</i>-position of the 3-phenyl ring were synthesized, and the concentrations required to inhibit chitin synthesis to 50% (IC<sub>50</sub>) were determined for all compounds. The introduction of halogens—such as F, Cl, and Br—and small alkyls—such as Me, Et, Pr, and <i>n</i>-Bu—at the 3-phenyl ring slightly enhanced the activity. However, the activity decreased drastically with the introduction of NO<sub>2</sub>, CF<sub>3</sub>, and <i>t</i>-Bu. The quantitative analysis of the substituent effect at the 3-phenyl ring on chitin-synthesis inhibition using the Hansch-Fujita method showed that the hydrophobic substituent with the optimum value was favored for the activity, but the bulky substituent in terms of <i>E</i><sub><i>s</i></sub> was detrimental to the activity.</p>\u0000<p></p>\u0000<img alt=\"\" src=\"https://www.jstage.jst.go.jp/pub/jpestics/advpub/0/advpub_D24-004/figure/advpub_D24-004.png\"/>\u0000<span style=\"padding-left:5px;\">Fullsize Image</span>","PeriodicalId":16712,"journal":{"name":"Journal of Pesticide Science","volume":"33 1","pages":""},"PeriodicalIF":2.4,"publicationDate":"2024-05-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141061026","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}
{"title":"Biodegradation of nitenpyram (neonicotinoid insecticide) by endophytic bacterium, Bacillus thuringiensis strain NIT-2, isolated from neonicotinoid-treated plant samples","authors":"Md. Tareq Bin Salam, Koji Ito, Ryota Kataoka","doi":"10.1584/jpestics.d24-002","DOIUrl":"https://doi.org/10.1584/jpestics.d24-002","url":null,"abstract":"</p><p>Nitenpyram (neonicotinoid insecticide) is commonly used for crop protection from pests. Currently, due to its widespread use, the nitenpyram accumulation in the environment is anticipated to be high. Hence, the removal of nitenpyram residue from the environment is essential. However, the biodegradation of nitenpyram by endophytes is still unreported. Therefore, we aimed to isolate and identify a bacterial strain capable of degrading nitenpyram. We isolated approximately 300 endophytic strains from <i>Brassica rapa</i> var. <i>perviridis</i> that had been exposed to different neonicotinoid insecticides. After 14 days of incubation, a bacterial strain, NIT-2, with nitenpyram degradation capability (approximately 65%) was found. <i>Via</i> 16S rRNA gene sequencing, the strain was identified as <i>Bacillus thuringiensis</i>. In addition, metabolites, 2-[<i>N</i>-(6-chloro-3-pyridylmethyl)-<i>N</i>-ethyl]amino-2-methyliminoacetic acid, <i>N</i>-(6-chloro-3-pyridilmethyl)-<i>N</i>-ethyl-<i>N</i>-methylformamidine (CPMF), and <i>N</i>-(6-chloro-3-pyridilmethyl)-<i>N</i>-ethylformamide (CPF), were identified during the degradation. Moreover, CPMF and CPF were further degraded 71% and 18%, respectively by NIT-2. Thus, <i>B. thuringiensis</i> strain NIT-2 is the first reported endophytic bacterium capable of degrading nitenpyram.</p>\u0000<p></p>\u0000<img alt=\"\" src=\"https://www.jstage.jst.go.jp/pub/jpestics/advpub/0/advpub_D24-002/figure/advpub_D24-002.png\"/>\u0000<span style=\"padding-left:5px;\">Fullsize Image</span>","PeriodicalId":16712,"journal":{"name":"Journal of Pesticide Science","volume":"25 1","pages":""},"PeriodicalIF":2.4,"publicationDate":"2024-05-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141061027","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}
{"title":"Dimesulfazet, a novel rice paddy herbicide, is an inhibitor of very long-chain fatty acid biosynthesis","authors":"Takamasa Furuhashi, Masato Otani, Mami Iwasa","doi":"10.1584/jpestics.d23-036","DOIUrl":"https://doi.org/10.1584/jpestics.d23-036","url":null,"abstract":"</p><p>Dimesulfazet can control annual and perennial sedges in rice paddies. Here we assessed its mode of action. We performed a phenotype assay of <i>Arabidopsis</i>, conducted a metabolomic analysis of <i>Echinochloa crus-galli</i>, and analyzed the endogenous concentration of very long-chain fatty acids (VLCFAs) in <i>Schoenoplectiella juncoides</i>. Dimesulfazet treatment caused curling and greening symptoms in the leaves and <i>fiddlehead</i>-like symptoms in the inflorescences of <i>Arabidopsis</i>. These symptoms were visually indistinguishable from those caused by flufenacet and benfuresate, which belong to Herbicide Resistance Action Committee (HRAC) Group 15. We performed GC-MS/MS analysis of primary metabolites and LC-MS analysis of lipids in the herbicide-treated <i>E. crus-galli</i>, followed by Orthogonal Partial Least Squares Discriminant Analysis clustering. The results showed that dimesulfazet belongs to the HRAC Group 15 cluster. The endogenous concentrations of C24:0, C26:0, and C28:0 decreased in dimesulfazet-treated plants as compared to those in the control. Overall, the mode of action of dimesulfazet involves the inhibition of VLCFA biosynthesis.</p>\u0000<p></p>\u0000<img alt=\"\" src=\"https://www.jstage.jst.go.jp/pub/jpestics/advpub/0/advpub_D23-036/figure/advpub_D23-036.png\"/>\u0000<span style=\"padding-left:5px;\">Fullsize Image</span>","PeriodicalId":16712,"journal":{"name":"Journal of Pesticide Science","volume":"25 1","pages":""},"PeriodicalIF":2.4,"publicationDate":"2024-04-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140799395","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}
{"title":"Investigation of variability in the matrix effect on stable isotope-labeled internal standards in liquid chromatography-tandem mass spectrometry analysis of 25 pesticides in vegetables","authors":"Arisa Banno, Yoshinori Yabuki, Motohiro Sonoda, Shinji Tanimori","doi":"10.1584/jpestics.d23-060","DOIUrl":"https://doi.org/10.1584/jpestics.d23-060","url":null,"abstract":"</p><p>The matrix effects (ME) in simultaneous analysis of pesticide residue using liquid chromatography-tandem mass spectrometry (LC-MS/MS) were evaluated by comparing the slopes of matrix-matched and reagent-only calibrations of four types of vegetable samples. Both the sampling and measurement variances of the ME were also determined using one-way analysis of variance. Substantial ion suppression (ME<−20%) was observed in komatsuna, spinach, and tomato when a modified Japanese official method was implemented. The ME magnitude varied significantly due to sample variability for some pesticides, but it varied by no more than 4% as a result of analytical procedure variance. This study also showed that the addition of stable isotope-labeled internal standards at low concentrations improved the recovery of pesticides from samples at various residue levels. The findings of this study highlight the importance and practical application of internal standards and the matrix-matched calibration method in residue analysis using LC-MS/MS.</p>\u0000<p></p>\u0000<img alt=\"\" src=\"https://www.jstage.jst.go.jp/pub/jpestics/advpub/0/advpub_D23-060/figure/advpub_D23-060.png\"/>\u0000<span style=\"padding-left:5px;\">Fullsize Image</span>","PeriodicalId":16712,"journal":{"name":"Journal of Pesticide Science","volume":"7 1","pages":""},"PeriodicalIF":2.4,"publicationDate":"2024-03-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140575727","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}
{"title":"Selective detection of paraquat by a cucurbit[7]uril-based fluorescent probe","authors":"Pei-Hui Shan, Ding-Wu Pan, Chun-Rong Li, Tie-Hong Meng, Carl Redshaw, Zhu Tao, Xin Xiao","doi":"10.1584/jpestics.d23-062","DOIUrl":"https://doi.org/10.1584/jpestics.d23-062","url":null,"abstract":"</p><p>A simple fluorescent “on-off” system that can be utilized for the selective identification and determination of paraquat (PQ) is presented herein. <sup>1</sup>H NMR spectroscopic data indicated that in aqueous solution the alkaloid palmatine can be partially encapsulated within the cucurbit[7]uril (Q[7]) cavity, whereby a stable 1 : 1 host–guest inclusion complex is formed. Other characterization techniques including mass spectrometry, UV-Vis and fluorescence spectroscopy also provided further evidence, and the host-guest inclusion complex was found to exhibit reasonable fluorescence intensity. It is noteworthy that the addition of PQ resulted in quenching the fluorescence of the host-guest inclusion complex, whereas the presence of 12 other pesticides did not significantly affect the fluorescence intensity. Given the linear relationship between the intensity of the fluorescence and the PQ concentration, the PQ concentration in aqueous solution was easily detected. Thus, a new method for identifying and determining the fluorescence quenching of PQ has been developed in this work.</p>\u0000<p></p>","PeriodicalId":16712,"journal":{"name":"Journal of Pesticide Science","volume":"8 1","pages":""},"PeriodicalIF":2.4,"publicationDate":"2024-03-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140199999","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}
{"title":"Degradation of the strobilurin fungicide mandestrobin in illuminated water–sediment systems","authors":"Takeshi Adachi, Yusuke Suzuki, Takuo Fujisawa","doi":"10.1584/jpestics.d23-056","DOIUrl":"https://doi.org/10.1584/jpestics.d23-056","url":null,"abstract":"</p><p>The degradation behavior of mandestrobin (<b>1</b>) was investigated in aerobic aquatic water–sediment systems exposed to continuous artificial sunlight (λ>290 nm). [<sup>14</sup>C]mandestrobin uniformly labeled at the phenoxy or benzyl ring was individually applied to the overlying water of the system at a rate equivalent to 262.5 g a.i./ha. The transformation of <b>1</b> was mainly proceeded <i>via</i> photoinduced bond cleavage at the benzyl phenyl ether and the subsequent rearrangement reaction. Interestingly, some of the photodegradates and microbial metabolites of <b>1</b> observed in the aquatic photodegradation and water–sediment (dark) studies, respectively, were never detected. Furthermore, the observed photoproducts were less formed and were steadily degraded or metabolized to carbon dioxide or strongly adsorbed to bottom sediment. The fate of <b>1</b> and its degradates in illuminated water–sediment systems was considered to reflect realistic conditions more precisely, as it accounts for various effects attributed to sunlight.</p>\u0000<p></p>\u0000<img alt=\"\" src=\"https://www.jstage.jst.go.jp/pub/jpestics/advpub/0/advpub_D23-056/figure/advpub_D23-056.png\"/>\u0000<span style=\"padding-left:5px;\">Fullsize Image</span>","PeriodicalId":16712,"journal":{"name":"Journal of Pesticide Science","volume":"4 1","pages":""},"PeriodicalIF":2.4,"publicationDate":"2024-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139911176","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}
Dinh Thi Chi, Ho Le Thi, Le Van Vang, Tran Thanh Thy, Masanobu Yamamoto, Tetsu Ando
{"title":"Mass trapping of the diamondback moth (Plutella xylostella L.) by a combination of its sex pheromone and allyl isothiocyanate in cabbage fields in southern Vietnam","authors":"Dinh Thi Chi, Ho Le Thi, Le Van Vang, Tran Thanh Thy, Masanobu Yamamoto, Tetsu Ando","doi":"10.1584/jpestics.d23-042","DOIUrl":"https://doi.org/10.1584/jpestics.d23-042","url":null,"abstract":"</p><p>A lure composed of (<i>Z</i>)-11-hexadecenal, (<i>Z</i>)-11-hexadecenyl acetate, and (<i>Z</i>)-11-hexadecen-1-ol at a ratio of 5 : 5 : 1 at a dose of 0.01 mg was optimal for the attraction of the Vietnamese strain of the diamondback moth (DBM). The combination of the sex pheromone with a plant volatile, allyl isothiocyanate, significantly increased the attraction of the pheromone trap. Females were also attracted, but they were only about 2% of all moths captured. In plots with 120–130 traps per ha, mass trapping with the combined lures reduced the DBM larval densities in cabbage fields as effectively as the spraying of insecticides 6 to 8 times. The weekly trap catches indicated that DBM adult densities in the mass-trapping fields were low until 28 days after transplantation, and then were kept to a modest increase until day 49. This field study also shows that the trap catches were well correlated with the DBM larval densities.</p>\u0000<p></p>\u0000<img alt=\"\" src=\"https://www.jstage.jst.go.jp/pub/jpestics/advpub/0/advpub_D23-042/figure/advpub_D23-042.png\"/>\u0000<span style=\"padding-left:5px;\">Fullsize Image</span>","PeriodicalId":16712,"journal":{"name":"Journal of Pesticide Science","volume":"131 1","pages":""},"PeriodicalIF":2.4,"publicationDate":"2024-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139919661","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}
{"title":"Using RNA interference targeting a nicotinic acetylcholine receptor subunit to counteract insecticide accommodation mechanisms: example of the β1 subunit in the imidacloprid-accommodated American cockroach, Periplaneta americana","authors":"Sebastien Ligonniere, Alexandre Bantz, Valerie Raymond, Delphine Goven","doi":"10.1584/jpestics.d23-027","DOIUrl":"https://doi.org/10.1584/jpestics.d23-027","url":null,"abstract":"</p><p>Insecticide accommodation and resistance are limiting factors to the much-needed increase in agricultural production. Various physiological and cellular modifications, such as the changes of insecticide molecular targets, have been linked to these events. Thus, a previous study demonstrated that the imidacloprid accommodation set up by the cockroach <i>Periplaneta americana</i> after an exposure to a sublethal dose of this insecticide involves functional alterations of two nicotinic acetylcholine receptor (nAChR) subtypes. As RNA interference (RNAi) is one of the most promising strategies for controlling pest insects, we evaluated, in this study, the use of RNAi that targets the β1 nAChR subunit to counteract the imidacloprid accommodation phenomenon in cockroaches. Interestingly, we showed that ingestion of dsRNA-β1 increased the sensitivity to imidacloprid of accommodated cockroaches. Thus, we have demonstrated for the first time that RNAi that targets an nAChR subunit can counteract the accommodation mechanism to insecticide targeting nAChRs set up by an insect.</p>\u0000<p></p>\u0000<img alt=\"\" src=\"https://www.jstage.jst.go.jp/pub/jpestics/advpub/0/advpub_D23-027/figure/advpub_D23-027.png\"/>\u0000<span style=\"padding-left:5px;\">Fullsize Image</span>","PeriodicalId":16712,"journal":{"name":"Journal of Pesticide Science","volume":"332 1","pages":""},"PeriodicalIF":2.4,"publicationDate":"2024-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139582548","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}
{"title":"Effects of flusulfamide on spore germination of Plasmodiophora brassicae","authors":"Taito Sasaki, Ryohei Naito, Toshiaki Ohara, Kosei Sakane, Shuhei Tanaka, Kazunori Sasaki, Aoi Osato, Yuki Nomura, Shin-ichi Ito","doi":"10.1584/jpestics.d23-031","DOIUrl":"https://doi.org/10.1584/jpestics.d23-031","url":null,"abstract":"</p><p>Flusulfamide inhibits germination of <i>Plasmodiophora brassicae</i> resting spores to suppress clubroot disease, but its mechanism of action on the germination of <i>P. brassicae</i> resting spores remains unclear. In this study, <i>P. brassicae</i> resting spores were treated with flusulfamide and visualized using transmission electron microscopy (TEM). The gene expression of <i>P. brassicae</i> resting spores was analyzed using RT-PCR, followed by immunoblotting analysis. TEM results revealed that flusulfamide suppressed the primary zoosporogenesis of <i>P. brassicae</i> resting spores during the early phase, and RT-PCR results revealed that flusulfamide affected the gene expression during the germination of the resting spores. Immunoblot and RT-qPCR analyses revealed that <i>PbCyp3</i>, an immunophilin (peptidyl-prolyl-isomerase) gene, was highly expressed, resulting in the unusual accumulation of PbCYP3 protein in <i>P. brassicae</i> resting spores immediately after treatment with flusulfamide. This suggests that flusulfamide may cause aberrant folding of proteins involved in primary zoosporogenesis, thereby inhibiting germination.</p>\u0000<p></p>\u0000<img alt=\"\" src=\"https://www.jstage.jst.go.jp/pub/jpestics/advpub/0/advpub_D23-031/figure/advpub_D23-031.png\"/>\u0000<span style=\"padding-left:5px;\">Fullsize Image</span>","PeriodicalId":16712,"journal":{"name":"Journal of Pesticide Science","volume":"211 1","pages":""},"PeriodicalIF":2.4,"publicationDate":"2024-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139515800","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}
{"title":"Insecticidal activity against rice pest of oxazosulfyl, a novel sulfyl insecticide","authors":"Masashi Kamezaki, Junko Otsuki, Katsuya Natsuhara","doi":"10.1584/jpestics.d23-057","DOIUrl":"https://doi.org/10.1584/jpestics.d23-057","url":null,"abstract":"</p><p>The development and commercialization of new chemical classes of insecticides are important for efficient crop protection, particularly for combatting insecticide resistance and providing sustainable agricultural production. This study reports on oxazosulfyl, a novel “sulfyl” class of insecticide, against a wide range of insect pests of rice. In the laboratory assay, oxazosulfyl showed insecticidal activity against all developmental stages of the brown planthopper <i>Nilaparvata lugens</i> (Stål). Phosphor imaging assays and soil drench bioassays demonstrated good systemic distribution in rice plants. Oxazosulfyl showed insecticidal activity against imidacloprid- and fipronil-resistant field populations of <i>N. lugens</i>, the white-backed planthopper <i>Sogatella furcifera</i> (Horváth), and the small brown planthopper <i>Laodelphax striatellus</i> (Fallén), as well as the respective susceptible strains. No cross-resistance was observed among oxazosulfyl, imidacloprid, and fipronil. Oxazosulfyl with a wide insecticidal spectrum is a potentially useful pest management tool for sustainable rice production.</p>\u0000<p></p>\u0000<img alt=\"\" src=\"https://www.jstage.jst.go.jp/pub/jpestics/advpub/0/advpub_D23-057/figure/advpub_D23-057.png\"/>\u0000<span style=\"padding-left:5px;\">Fullsize Image</span>","PeriodicalId":16712,"journal":{"name":"Journal of Pesticide Science","volume":"43 1","pages":""},"PeriodicalIF":2.4,"publicationDate":"2024-01-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139481120","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}