Quantitative structure‐activity analysis of larvicidal 1‐(substituted benzoyl)‐2‐benzoyl‐1‐tert‐butylhydrazines against <i>Chilo suppressalis</i>

Oikawa, Nobuhiro; Nakagawa, Yoshiaki; Nishimura, Keiichiro; Ueno, Tamio; Fujita, Toshio

doi:10.1002/ps.2780410210

Cited by 55 publications

(47 citation statements)

References 32 publications

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“…1) on the larvicidal potency were analyzed quantitatively using the Hansch-Fujita QSAR method. [10][11][12][13][14][15] The QSAR results reinforced clearly the above described similarity in larvicidal activity among the same insect orders and difference between different insect orders in terms of physicochemical effects. These structure-activity studies are useful for elucidating the structures of potent larvicides.…”

Section: Introductionsupporting

confidence: 72%

“…These observations are consistent with the results of our previous studies. [10][11][12][13][14][15] The significance of the log P term in Eq. 3 indicates that hydrophobic para-substituents enhance the binding of DBHs to the receptor.…”

Section: Discussionmentioning

confidence: 99%

“…In our previous QSAR study for the larvicidal activity of the same series of compounds against C. suppressalis, steric parameters, L and V w , were significant instead of B 1 . 10,11) The parameter L represents the length and B 5 represents the maximum width of the substituent. 21) The significance of B 1 , but not of B 5 or L, means that, in the receptor binding, the steric repulsion in the para position occurs from the side where their width is minimum.…”

Section: Discussionmentioning

confidence: 99%

“…8) In addition, because these insecticides are safe to aquatic organisms and beneficial insects, they are environmentally and ecologically acceptable as part of an integrated pest management (IPM) program. 9) Previously, we measured larvicidal activities of various series of DBHs in two lepidopteran species, the rice stem borer Chilo suppressalis 10,11) and the beet armyworm Spodoptera exigua, 12,13) as well as the coleopteran Colorado potato beetle Leptinotarsa decemlineata. 14,15) The relationship of larvicidal potency to the substitution pattern on two benzene rings of DBHs was similar for the activities against two lepidopteran insect species, but entirely different for activities against lepidopteran and coleopteran insects.…”

Section: Introductionmentioning

confidence: 99%

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QSAR for Binding Affinity of Substituted Dibenzoylhydrazines to Intact Sf-9 Cells

et al. 2005

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The binding affinity to intact Sf-9 cells was measured in a series of N-t-butyl-N,NЈ-dibenzoylhydrazine congeners. The benzene ring close to the t-butyl group of the compounds was substituted with Cl at the ortho-position and the other benzene ring was variously substituted at the para-position. The effects of the substituent on the binding affinity were analyzed quantitatively using the Hansch-Fujita QSAR method. The introduction of hydrophobic and electron-donating substituents at the para-position enhanced the binding affinity toward the ecdysone receptor protein. Steric repulsion between the substituent and receptor surface was also suggested.

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Section: Introductionsupporting

confidence: 72%

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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QSAR for Binding Affinity of Substituted Dibenzoylhydrazines to Intact Sf-9 Cells

et al. 2005

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“…18,19) 2. P-gp ATPase activity Human P-glycoprotein expressed by Sf9 insect cells was purified according to a previous report.…”

Section: Methodsmentioning

confidence: 99%

Substrate recognition by P-glycoprotein efflux transporters: Structure-ATPase activity relationship of diverse chemicals and agrochemicals

et al. 2013

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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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Quantitative structure-activity studies of insect growth regulators xiv. Three-dimensional quantitative structure-activity relationship of ecdysone agonists including dibenzoylhydrazine analogs

et al. 1998

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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 e †ects of two carbonyl groups as well as two benzene rings of dibenzoylhydrazine. The quantitative structureÈactivity relationship of ecdysone agonists including dibenzoylhydrazine analogs was analyzed three-dimensionally using the CoMFA (comparative molecular Ðeld 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 ( Pestic. Sci., 53, 267È277 (1998)

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Quantitative structure‐activity analysis of larvicidal 1‐(substituted benzoyl)‐2‐benzoyl‐1‐tert‐butylhydrazines against Chilo suppressalis

Cited by 55 publications

References 32 publications

QSAR for Binding Affinity of Substituted Dibenzoylhydrazines to Intact Sf-9 Cells

QSAR for Binding Affinity of Substituted Dibenzoylhydrazines to Intact Sf-9 Cells

Substrate recognition by P-glycoprotein efflux transporters: Structure-ATPase activity relationship of diverse chemicals and agrochemicals

Quantitative structure-activity studies of insect growth regulators xiv. Three-dimensional quantitative structure-activity relationship of ecdysone agonists including dibenzoylhydrazine analogs

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