Molecular Modeling Study on the Structure−Activity Relationship of Substituted Dibenzoyl-1-tert-butylhydrazines and Their Structural Similarity to 20-Hydroxyecdysone

Qian, Xuhong

doi:10.1021/jf950269f

Cited by 22 publications

(29 citation statements)

References 11 publications

(14 reference statements)

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“…This underlies their unique mode of insecticidal activity and generates further interest in the conformational behavior of diacylhydrazines. It is difficult to model these compounds or formulate a meaningful pharmacophore without a better knowledge of the structure and flexibility of the central N−N bond than currently exists.…”

Section: Introductionmentioning

confidence: 99%

Theoretical Study of the Structure and Rotational Flexibility of Diacylhydrazines: Implications for the Structure of Nonsteroidal Ecdysone Agonists and Azapeptides

Reynolds

Hormann

1996

J. Am. Chem. Soc.

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High-level ab initio calculations have been used to determine the minimum energy structures of N,N‘-diformylhydrazine, N-methyl-N,N‘-diformylhydrazine, and N,N‘-dimethyl-N,N‘-diformylhydrazine. These calculations show that the global minimum is a nonplanar structure in which the nitrogen lone pairs are essentially perpendicular to one another. However, the energy required for (Z,Z)-diformylhydrazine to adopt a planar structure is less than 1 kcal/mol (MP2/6-31+G**). This is due to attractive intramolecular hydrogen bonds between the N-hydrogens and the carbonyl oxygens in the planar geometry. When one or both amide configurations are inverted (Z,E; E,E), or when the nitrogens are substituted, with methyl for example, these hydrogen bonds are lost and the planar structure becomes much less stable relative to the twisted rotamer. Thus, we conclude from these calculations that diacylhydrazines are intrinsically nonplanar with respect to the CO−N−N−CO torsion, and that with the exception of (Z,Z)-diformylhydrazine the rotational barriers are large. The observation of a planar crystal structure for diformylhydrazine is due to additional intermolecular hydrogen bonds which are available to planar diformylhydrazine in the crystal lattice. Finally, these calculations have significant implications for the structure and dynamical properties of nonsteroidal ecdysone agonists, azapeptides, and azatides which incorporate the diacylhydrazine structure.

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Section: Introductionmentioning

confidence: 99%

Theoretical Study of the Structure and Rotational Flexibility of Diacylhydrazines: Implications for the Structure of Nonsteroidal Ecdysone Agonists and Azapeptides

Reynolds

Hormann

1996

J. Am. Chem. Soc.

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“…Insect growth regulators are designed and synthesized to take advantage of unique aspects of development compared to other organisms ( Verloop et al 1977 ; Oberlander et al 1998 ), which makes them safe to nontargets, highly friendly to the environment, and selective for insects and acari. Therefore, IGRs have been developed in recent years by researchers throughout the world ( Qian 1996 ; Yang et al 1999 ).…”

Section: Introductionmentioning

confidence: 99%

Evaluation of etoxazole against insects and acari in vegetables in China

Yang

Wei

et al. 2014

Journal of Insect Science

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Etoxazole, 2-(2,6-difluorophenyl-4-[4-(1,1-dimethylethyl)-2-ethoxy-phenyl]-4,5-dihydrooxazole, an organofluorine chitin synthesis inhibitor, was assayed for its bioactivities against several major insect and acarus pests and compared to several other pesticides: two chitin synthesis inhibitors, hexaflumuron and chlorfluazuron; a pyrethroid, permethrin; an organophosphate, acephate; a carboximide, hexythiazox; and a tetrazine, clofentezine. The LC 50 of etoxazole was calculated using probit analysis of the concentration-dependent mortality data against susceptible and resistant strains of the beet armyworm, Spodoptera exigua (Hubner) (Lepidoptera: Noctuidae); diamondback moth, Plutella xylostella L. (Plutellidae); bean aphid, Aphis craccivora Koch (Hemiptera: Aphididae); and carmine spider mite, Tetranychus cinnabarinus (Boisduval) Boudreaux (Trombidiformes: Tetranychidae). The resistant strains were found to be resistant against all tested pesticides except etoxazole. The bioactivity of etoxazole was many times that of the other tested insecticides and acaricides widely used in vegetable crops in China. On the basis of our research, etoxazole can be expected to be extensively used on vegetable crops in China.

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“…2). In this paper we describe the preparation of fourteen new B-ring-modified RH-5992 analogues (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14) and also their insecticidal activity against the common cutworm (Spodoptera litura). MATERIALS AND METHODS…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Insecticidal Activity of 3, 5-Dimethylbenzoyl Moiety Modified Analogues of N-tert-Butyl-N′-(4-ethylbenzoyl)-3, 5-dimethylbenzohydrazide

善宏¹,

春美²,

芳久³

et al. 2002

J. Pestic. Sci.

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Molecular Modeling Study on the Structure−Activity Relationship of Substituted Dibenzoyl-1-tert-butylhydrazines and Their Structural Similarity to 20-Hydroxyecdysone

Cited by 22 publications

References 11 publications

Theoretical Study of the Structure and Rotational Flexibility of Diacylhydrazines: Implications for the Structure of Nonsteroidal Ecdysone Agonists and Azapeptides

Theoretical Study of the Structure and Rotational Flexibility of Diacylhydrazines: Implications for the Structure of Nonsteroidal Ecdysone Agonists and Azapeptides

Evaluation of etoxazole against insects and acari in vegetables in China

Synthesis and Insecticidal Activity of 3, 5-Dimethylbenzoyl Moiety Modified Analogues of <i>N</i>-<i>tert</i>-Butyl-<i>N</i>′-(4-ethylbenzoyl)-3, 5-dimethylbenzohydrazide

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