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1.
Yoshiaki Nakagawa Kazunari Hattori Bun-ichi Shimizu Miki Akamatsu Hisashi Miyagawa Tamio Ueno 《Pest management science》1998,53(4):267-277
N-tert-Butyl-N,N′-dibenzoylhydrazines such as tebufenozide (RH-5992) mimic the action of a molting hormone, 20-hydroxyecdysone, and cause premature molting of larvae leading to their death. Previously, it was shown that one of the benzoyl moieties in dibenzoylhydrazines plays a role similar to that of the aliphatic side chain at the C-17 position of ecdysones. In the present study, N-benzoyl-N′-benzylhydrazine, N,N′-dibenzylhydrazine, and N-alkanoyl-N′-benzoylhydrazine analogs have been synthesized to compare the effects of two carbonyl groups as well as two benzene rings of dibenzoylhydrazine. The quantitative structure–activity relationship of ecdysone agonists including dibenzoylhydrazine analogs was analyzed three-dimensionally using the CoMFA (comparative molecular field analysis) procedure. The CoMFA results suggested that the two carbonyl oxygen atoms of the diacylhydrazine skeleton probably correspond to the oxygens of the 20- and 22-OH groups of ecdysones, and that the benzoyl moiety located closer to the tert-butyl group is important for retaining high activity. © 1998 SCI 相似文献
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Yoshiaki Nakagawa Katsuhiko Kitahara Takaaki Nishioka Hajime Iwamura Toshio Fujita 《Pesticide biochemistry and physiology》1984,21(3):309-325
The larvicidal activity of a series of N-2,6-difluoro- and N-2,6-dichlorobenzoyl-N′-(4-substituted phenyl)ureas against nondiapause larvae of the rice stem borer, Chilo suppressalis Walker, was measured by topical application and oral administration methods under conditions with and without piperonyl butoxide as an inhibitor of oxidative metabolism. The effects of substituents at the anilide moiety on the larvicidal activity were analyzed quantitatively using physicochemical substituent parameters and regression analysis. The results indicate that the oxidative metabolism in the larval body which is favored by electron-donating substituents is significant in determining the activity. The activity, when the metabolic factor is eliminated, is enhanced by electron-with-drawing and hydrophobic substituents and lowered by bulky groups. The inhibitory activity against new cuticle formation of the same series of compounds was also measured using cultured integument of the rice stem borer diapause larva. The comparison of the quantitative analyses between larvicidal and integument-level activities shows that inhibition of cuticular development is the most important factor governing larvicidal activity. 相似文献
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Kotaro Mori Hideya Tokuoka Hisashi Miyagawa Yoshiaki Nakagawa 《Journal of Pesticide Science》2021,46(1):120
Benzoylphenylureas (BPUs) were discovered as novel type insecticides about a half century ago; many analogs have been launched as insecticides and acaricides. BPUs are known to inhibit chitin synthesis in insects and other arthropods, but they have no effect against microorganisms such as fungi. We designed new chitin synthesis inhibitors based on the hypothesis that biomolecules that play important roles in cellulose and chitin biosynthesis are similar. In the full automatic modeling system (FAMS), the cellulose synthase was selected as a template three-dimensional structure. Thus, we focused on the structure of cellulose synthase inhibitor, isoxaben, to develop new chemistry. The 1,1-diethylethyl [-C(CH3)(CH2CH3)2] group of isoxaben was changed to a 4-substituted phenyl group bearing Cl, Et, or Ph. These compounds significantly inhibited chitin synthesis in the cultured integument of the rice stem borer Chilo suppressalis. The activity of the 4-ethylphenyl analog was enhanced 30-fold by adding piperonyl butoxide to the culture medium. 相似文献
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Yoshiaki Nakagawa Hajime Iwamura Toshio Fujita 《Pesticide biochemistry and physiology》1985,23(1):7-12
The larvicidal activity of a series of N-2,6-difluorobenzoyl-N′-[4-(substituted benzyloxy)-phenyl]-ureas against nondiapause larvae of the rice stem borer, Chilo suppressalis Walker, was measured by a topical application method under conditions in which oxidative metabolism was inhibited by piperonyl butoxide. The effects of the substituted-benzyloxy moiety on variations in the activity were analyzed quantitatively using physicochemical substituent parameters and regression analysis. Results were compared with those found previously for N-2,6-difluorobenzoyl-N′-(4-substituted phenyl)-ureas, indicating that the electron-withdrawing property of the anilide substituents participates in determining the activity through the inductive effect. The hydrophobicity of the total anilide substituents favors activity, whereas the steric dimension in terms of the width lowers it. Although inhibition of new cuticle formation on cultured integument of diapausing larva could not be determined accurately for most of the compounds because of their limited solubility in the assay medium, inhibitory activity seemed related to larvicidal activity, as was the case for previously investigated simpler congeners. 相似文献
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Juliana DF Barbosa Viviane B Silva Péricles B Alves Giuseppe Gumina Roseli LC Santos Damião P Sousa Sócrates CH Cavalcanti 《Pest management science》2012,68(11):1478-1483
BACKGROUND: Dengue fever is a severe public health problem for several countries. In order to find effective larvicides to aid control programs, the structure‐activity relationships of eugenol derivatives against Aedes aegypti (Diptera: Culicidae) larvae were evaluated. Additionally, the composition and larvicidal activity of Syzygium aromaticum essential oil was assessed. RESULTS: Four compounds representing 99.05% of S. aromaticum essential oil have been identified. The essential oil was active against Ae. aegypti larvae (LC50 = 62.3 and 77.0 ppm, field‐collected and Rockefeller larvae respectively). The larvicidal activity of eugenol, the major compound of the essential oil, was further evaluated (LC50 = 93.3 and 71.9 ppm, field‐collected and Rockefeller larvae respectively). The larvicidal activity and structure‐activity relationships of synthetic derivatives of eugenol were also assessed. The larvicidal activity of the derivatives varied between 62.3 and 1614.9 ppm. Oxidation of eugenol allylic bond to a primary alcohol and removal of the phenolic proton resulted in decreased potency. However, oxidation of the same double bond in 1‐benzoate‐2‐methoxy‐4‐(2‐propen‐1‐yl)‐phenol resulted in increased potency. CONCLUSION: Structural characteristics were identified that may contribute to the understanding of the larvicidal activity of phenylpropanoids. The present approach may help future work in the search for larvicidal compounds. Copyright © 2012 Society of Chemical Industry 相似文献
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Effects of the chitin synthesis inhibitor diflubenzuron (DFB) on the integument of 5th instarGalleria mellonella L. larvae were investigated. When larvae were fed with semi-artificial diets containing 250, 500 and 1000 ppm of the compound,
DFB affected the integument. The affected larvae failed to ecdysis, their cuticle was ruptured, lost haemolymph and blackened.
In treated larvae, cuticle deposition was disrupted and the cuticle thickness was decreased by ∼50% compared with the untreated
control, particularly at day 3 1/2. However, statistically there was no significant difference among the three concentrations
(P>0.05). This may indicate that all three concentrations are equally effective in decreasing level. DFB at 500 and 1000 ppm
also affected the epidermal cells and caused the occurrence of vacuoles.
http://www.phytoparasitica.org posting Dec. 16, 2003. 相似文献
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BACKGROUND: Tyramine (TA) and octopamine (OA) are considered to be the invertebrate counterparts of the vertebrate adrenergic transmitters. Because these two phenolamines are the only biogenic amines whose physiological significance is presumably restricted to invertebrates, the attention of pharmacologists has been focused on the corresponding receptors, which are believed to represent promising targets for novel insecticides. For example, the formamidine pesticides, such as chlordimeform and amitraz, have been shown to activate OA receptors. RESULTS: A full‐length cDNA (designated CsTyR1) from the rice stem borer, Chilo suppressalis (Walker), has been obtained through homology cloning in combination with rapid amplification of cDNA ends/polymerase chain reaction (RACE‐PCR). The mRNA of CsTyR1 is present in various tissues, including hemocytes, fat body, midgut, Malpighian tubules, nerve cord and epidermis, and it is found predominantly in the larval nerve cord with 16–80‐fold enrichment compared with other tissues. The authors generated a HEK 293 cell line stably expressing CsTyR1 in order to examine functional and pharmacological properties of this receptor. Both TA and OA at 0.01–100 µM can reduce forskolin‐stimulated intracellular cAMP levels in a dose‐dependent manner (TA, EC50 = 369 nM ; OA, EC50 = 978 nM ). In agonist assays, activation of CsTyR1 by clonidine and amitraz but not by naphazoline and chlordimeform can also significantly inhibit forskolin‐stimulated cAMP production. The inhibitory effect of TA at 10 µM is eliminated by coincubation with yohimbine, phentolamine or chlorpromazine (each 10 µM ). CONCLUSION: This study represents a comprehensive molecular and pharmacological characterisation of a tyramine receptor in the rice stem borer. Copyright © 2012 Society of Chemical Industry 相似文献
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Saad M. M. Ismail Richard A. Baines Roger G. H. Downer Mark A. Dekeyser 《Pest management science》1996,46(2):163-170
Dihydrooxadiazines are structural analogs of octopamine and were compared with octopamine for their ability to compete with [3H]dihydroergocryptine ([3H]DHE) for binding sites on DHE-sensitive receptors, to stimulate adenylate cyclase activity in nervous system homogenates of Periplaneta americana L., and to modulate the action of the peptide proctolin on the oviducal muscles of Locusta migratoria L. [3H]DHE binding was inhibited by low concentrations (μM range) of octopamine, phentolamine, N-demethylchlordimeform (DCDM) and several dihydrooxadiazines. The tested dihydrooxadiazines acted as aminergic agonists in stimulating cyclic AMP production in cockroach nervous system homogenates and did not show additive effects with octopamine, whereas additivity was observed with 5-hydroxytryptamine. The relative potency of octopaminergic antagonists, including mianserin, cyproheptadine, phentolamine, and gramine, to block octopamine-mediated elevation of cyclic AMP production was similar to the rank-order potency of the same antagonists to inhibit dihydrooxadiazine-mediated elevation of cyclic AMP production. Octopamine, 2-(4-bromophenyl)-5,6-dihydro-4H-1,3,4-oxadiazine (4-Br-PDHO), and 8-Br-cyclic AMP caused increased phosphorylation of proteins that are phosphorylated by exogenously added cyclic AMP-dependent protein kinase. These results indicate that the dihydrooxadiazine-induced rise in cyclic AMP levels in homogenates of the cockroach nervous system results directly in activation of an endogenous cyclic AMP-dependent protein kinase. 4-Br-PDHO behaved similarly to octopamine in modulating the action of proctolin-induced contractions in locust oviducal muscles. These observations suggest that dihydrooxadiazines act as octopamine agonists and have an octopaminergic action in modulating the action of proctolin. Thus, it is proposed that dihydrooxadiazines exert at least part of their insecticidal and miticidal actions through interaction with the octopaminergic system. 相似文献
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The inhibitory activity of commercial and experimental triazole fungicides on the target enzyme, sterol 14α-demethylase (P45014DM), was studied in a cell-free sterol synthesis assay of Botrytis cinerea Pers. ex Fr. In order to assess structure-activity relationships, the inhibitory activities of the compounds on radial growth of the fungus were tested as well. The EC50 values (concentrations of fungicide inhibiting radial growth of B. cinerea on PDA by 50%) of all triazoles tested ranged between 10?8 and 10?5 m. IC50 values (concentrations of fungicide inhibiting incorporation of [2-14C]mevalonate into C4-desmethyl sterols by 50%) generally ranged between 10?9 and 10?7 M and correlated with inhibition of radial mycelial growth. However, differences in IC50 values did not reflect quantitatively the observed differences in EC50 values, since the ratio between EC50 and IC50 increased with decreasing fungitoxicity. For a limited number of compounds the correlation between intrinsic inhibitory activity and fungitoxicity was low. Both in-vitro tests were used to investigate structure-activity relationships for stereoisomers of cyproconazole, SSF-109 and tebucona-zole. Fungitoxicity and the potency to inhibit cell-free C4-desmethyl sterol synthesis correlated for all stereoisomers tested. Mixtures of isomers of tebucona-zole or cyproconazole were slightly less active than the most potent isomer. The high activity of several commercial triazoles in both experiments implies that poor field performance of triazole fungicides against B. cinerea is due neither to insensitivity of the P45014DM nor to low in-vitro sensitivity of the fungus. 相似文献
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通过2011—2013年应用黏胶型性诱捕器和灯测2种方法对水稻二化螟越冬代成虫同地对比诱测试验,结果表明：性诱测第2蛾峰高峰日,与灯诱测的雌蛾始盛期相吻合,可以作为不同地理生态区和非灯诱监测区简化精准预测第1代二化螟发生期的重要依据,具有较强的实际指导价值。可以将该地此蛾峰日、峰日后的3-4d、10-11d分别作为预测雌蛾的发蛾始盛期、高峰期、盛末期,不同地区可根据实际确定和选取相应期距值。在此基础上,再加上相应的产卵前期和卵历期,就可对第1代二化螟卵孵始盛期、高峰期、盛末期作出预测。2011—2013年性诱预测结果与实际相符合。该法预测准确,简便易行,建议该技术在基层测报点推广应用。 相似文献
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Darren R. Chandler Robert G. King Philip Jewess Stuart E. Reynolds 《Pest management science》1991,31(3):295-304
The toxic effects of six acylurea insecticides on larvae of the tobacco hornworm were investigated at each of four environmental temperatures (20, 25, 30 and 35°C). This spans the range of temperatures which the insects can tolerate. For all the acylureas tested, mortality increased with temperature when either newly hatched or fourth-instar larvae were given insecticide in their food. Sub-lethal growth inhibition also became more pronounced at progressively higher environmental temperatures. This temperature dependence of acylurea action was not due to altered uptake of the insecticide, since there was no significant variation with temperature in the amount of [14C]flufenoxuron taken up by fifth-instar larvae when given a single meal containing labelled insecticide. Additionally, mortality of fourth-instar larvae given a single intra-haemocoelic injection of flufenoxuron was significantly greater at higher temperatures, implying that temperature affects a process that occurs after insecticide uptake. The intrinsic ability of acylureas to inhibit chitin synthesis is temperaturesensitive, since flufenoxuron inhibited the incorporation of [14C]N-acetylalucosamine into chitin by proleg epidermis in vitro significantly less well at 20°C than at the higher temperatures tested. However, there was no significant variation between the effectiveness of in-vitro chitin synthesis inhibition at 25, 30 and 35°C. These data show that the effectiveness of acylurea insecticides is subject to strong temperature effects in the range of temperatures likely to be experienced in the field. 相似文献
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Yih-Shen Hwang Mir S. Mulla Mary Mistrot Pope Cesar Rodriguez 《Pest management science》1982,13(5):517-522
N,N-Diethyl-, N,N-dipropyl-, N,N-di-isopropyl, and N,N-di-isobutylalkanamides in which the acyl moiety ranged from C8 to C21 were synthesised, and their larvicidal activity was determined against the first-instar larvae of the southern house mosquito Culex quinquefasciatus Say. The four homologous series of amides generally showed an increase in their larvicidal activity as the carbon number in the acyl moiety of the amides increased, until the activity reached a maximum. Subsequently, an increment of carbon number resulted in declining activity in the higher homologues, until the activity disappeared. N,N-Diethyltetradecanamide, N,N-dipropylundecanamide, N,N-di-isopropylundecanamide, and N,N-di-isobutlynonanamide or -dodecanamide were the most active compounds in their respective homologous series of amides; however, they were less active than their analogous N,N-dimethylalkanamides previously studied. 相似文献
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研究了雷公藤根皮乙醇提取物对茭白二化螟的生物活性 ,结果表明 ,提取物对二化螟幼虫有较强的拒食作用、生长发育抑制作用、毒杀作用和内吸毒力。对 2龄 1日幼虫选择性与非选择性的拒食中浓度 (AFC50)分别为111.57μg/mL和 144.28μg/mL ,生长发育的抑制中浓度 (EC50)为 134.39μg/mL。内吸毒杀作用在 1600μg/mL浓度下能达到 90%以上 ,胃毒作用在 800μg/mL下 ,处理 5d后的死亡率为 73.71% ,对二化螟蚁螟的触杀作用不明显 ,对天敌螟黄足绒茧蜂安全。 相似文献
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15%阿维·毒乳油防治水稻二化螟田间药效试验 总被引：1，自引：0，他引：1
进行了15%阿维菌素·毒死蜱乳油防治水稻二化螟田间药效试验,结果表明,该药剂能有效防治水稻二化螟,每667㎡用40～80ml喷雾防治,药后20 d防治效果达76.24%～98.66%,防治效果随用药量的增加而提高,且对试验作物安全。 相似文献
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不同食料对人工饲养的二化螟生长发育和产卵量的影响 总被引：7，自引：2，他引：7
以浙江省 3种主栽水稻品种浙辐 910、杂交稻 (Ⅱ优 3027)、秀水 11的稻苗为供试食料喂饲二化螟 ,研究了 3种食料对二化螟生长发育和产卵量的影响。结果发现 ,3种食料对二化螟的存活率及性比影响较显著 ,对其发育历期的影响仅在低龄时有显著差异。不同的食料对二化螟蛹和成虫大小及产卵量的影响不大 ;在同样的食料条件下 ,不同性别间的发育历期差别不大 ,但二化螟蛹及成虫的大小在两性间差异显著 ,初蛹体重、体长以及成虫体重、体长 ,都是雌性极显著大于雄性 相似文献
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Substitution of silicon for carbon was explored in etofenprox and MTI-800, primarily to establish the suitability of silicon for pesticide construction and to probe steric effects. It was shown that silicon is an effective building block for insecticides with subtle qualitative and quantitative differences relative to the carbon analogs. The silanes were slightly less toxic to insects than the carbon analogs (relative potency of 0.2-0.6) but the silane analog of MTI-800 was considerably less toxic to fish (0% mortality at ≥50 mg liter?1) than MTI-800 itself (LC50 = 3 mg liter?1). The mode of action of both carbon and silicon compounds was similar in the intact, electrode-implanted cockroach and involved repetitive firing of a sensory nerve; potency measurements were also made using an in-vitro nerve assay. The possible metabolic and physicochemical contributions to the observed insecticide potencies were explored using synergism studies, physical chemistry measurements and quantum mechanical calculations. 相似文献
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Ranil Waliwitiya Christopher J Kennedy Carl A Lowenberger 《Pest management science》2009,65(3):241-248
BACKGROUND: Aedes aegypti L. is the major vector of dengue fever and dengue hemorrhagic fever. In an effort to find effective tools for control programs to reduce mosquito populations, the authors assessed the acute toxicities of 14 monoterpenoids, trans‐anithole and the essential oil of rosemary against different larval stages of Ae. aegypti. The potential for piperonyl butoxide (PBO) to act as a synergist for these compounds to increase larvicidal activity was also examined, and the oviposition response of gravid Ae. aegypti females to substrates containing these compounds was evaluated in behavioral bioassays. RESULTS: Pulegone, thymol, eugenol, trans‐anithole, rosemary oil and citronellal showed high larvicidal activity against all larval stages of Ae. aegypti (LC50 values 10.3–40.8 mg L?1). The addition of PBO significantly increased the larvicidal activity of all test compounds (3–250‐fold). Eugenol, citronellal, thymol, pulegone, rosemary oil and cymene showed oviposition deterrent and/or repellent activities, while the presence of borneol, camphor and β‐pinene increased the number of eggs laid in test containers. CONCLUSIONS: This study quantified the lethal and sublethal effects of several phytochemical compounds against all larval stages of Aedes aegypti, providing information that ultimately may have potential in mosquito control programs through acute toxicity and/or the ability to alter reproductive behaviors. Copyright © 2008 Society of Chemical Industry 相似文献