Quantitative structure-activity relationships in acaricidal 4H-1,3,4-oxadiazin-5(6H)-ones

Dekeyser, Mark A.; Borth, David M.; Moore, Richard C.; Mishra, Anupama

doi:10.1021/jf00002a030

Cited by 19 publications

(12 citation statements)

References 8 publications

(10 reference statements)

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“…This report outlines a short history of its discovery. system enhanced activity [4]. Therefore, we synthesized and evaluated a few structurally-diverse ortho-biphenyl-substituted hydrazine derivatives.…”

Section: Introductionmentioning

confidence: 99%

The Discovery of Bifenazate, a Novel Carbazate Acaricide

Dekeyser¹,

McDonald²,

Angle³

2003

Chimia

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A history of the discovery of the novel carbazate acaricide, bifenazate, is outlined. When a novel ortho-biphenyl substituted hydrazide compound showed acaricidal activity in the pesticide discovery screen, a small number of analogs were made to confirm and explore acaricidal effects. An ortho-biphenylcarbazate analog gave significantly greater acaricidal activity. Thereafter, several hundred structurally-diverse biphenyl-substituted carbazate analogs were synthesized and evaluated in a bioassay with the two-spotted spider mite (Tetranychus urticae Koch) in order to optimize the acaricidal activity. As a result of the optimization process, bifenazate, the analog with a methoxybiphenyl substituent to the terminal nitrogen atom of isopropyl carbazate, was selected for development and registration.

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Section: Introductionmentioning

confidence: 99%

The Discovery of Bifenazate, a Novel Carbazate Acaricide

Dekeyser¹,

McDonald²,

Angle³

2003

Chimia

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“…± A diversity of biological effects is associated with 1,3,4-oxadiazine and its derivatives, they exhibit cardiovascular [1 ± 3], antibacterial [4], plant-growth regulating [5], miticidal and nematocidal [6], acricidal [7], and insecticidal activities [8] and monoamine-oxidase (MAO) inhibition [9]. The promising therapeutic potential of this class of compounds prompted us to synthesize and biologically screen a series of structural variants of 4H-1,3,4-oxidiazine-5(6H)-ones.…”

mentioning

confidence: 99%

Synthesis and Biological Screening of 2-Substituted 5,6-Dihydro-5-oxo- 4H-1,3,4-oxadiazine-4-propanenitriles and of Their Intermediates

Khan

Rahat

Choudhary

et al. 2002

HCA

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To evaluate the effect of substituents on biological activities of electron-rich N-containing heterocycles, the variably 2-substituted 5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitriles 26 ± 33 were synthesized and evaluated for antibacterial, antifungal, and enzyme-inhibition activities. The target compounds were obtained from alkyl 4-or 3-hydroxy benzoates 1 and 2, respectively, and from methyl indoleacetate 3. The phenolic OH group of benzoates 1 and 2 were substituted with p-toluenesulfonyl ( 3 4 and 5), benzoyl ( 3 6 and 7), and benzyl groups ( 3 8 and 9) and then converted to 5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitriles. To establish structure-activity relationships (SAR), a pharmacological screening of the intervening intermediates was also conducted, which revealed that the intermediate hydrazide 11 possesses significant antimicrobial and MAO-A inhibiting properties and intermediates 12, 24, 28, and 29 appreciable antifungal activities. Compound 7 inhibits a-chymotrypsin. Introduction. ± A diversity of biological effects is associated with 1,3,4-oxadiazine and its derivatives, they exhibit cardiovascular [1 ± 3], antibacterial [4], plant-growth regulating [5], miticidal and nematocidal [6], acricidal [7], and insecticidal activities [8]and monoamine-oxidase (MAO) inhibition [9]. The promising therapeutic potential of this class of compounds prompted us to synthesize and biologically screen a series of structural variants of 4H-1,3,4-oxidiazine-5(6H)-ones. To establish structure activity relationships (SAR), the activities of the intervening intermediates were also determined. Thus, the readily available alkyl benzoates 1, 2, and 4 ± 9 and the indoleacetate 3 were transformed to the target 5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitriles 26 ± 33 in excellent yields. The structures of 26 ± 33 were established by spectroscopic techniques, and their biological activities were determined.

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“…QSAR analyses of other acaricides were also executed, and it was shown that hydrophobicity is an important physicochemical property for activity [29][30][31][32][33] . For instance, acaricidal activities of pyrethroids 31) and alkanesulfonates 29) were parabolically correlated with hydrophobicity parameters such as p and log kЈ.…”

Section: Discussionmentioning

confidence: 99%

QSAR of 2,4-diphenyl-1,3-oxazolines for ovicidal activity against the two-spotted spider mite Tetranychus urticae

Suzuki¹,

Tanji²,

Ota³

et al. 2006

J. Pestic. Sci.

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Ovicidal activity of 2,4-diphenyl-1,3-oxazoline congeners with various substituents on the 4-phenyl ring against two-spotted spider mites Tetranychus urticae was quantitatively analyzed using the classical QSAR (HanschFujita) method. In QSAR analysis, hydrophobicity in terms of log P (P: partition coefficient between 1-octanol and water) was the most significant parameter with its square term. The optimum log P value for 2,4-diphenyl-1,3-oxazoline analogs was evaluated as about 7.1. The introduction of substituents with inductive electron-withdrawing properties was also favorable to activity, but the presence of substituents at the ortho-and meta-positions was not promising.

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Quantitative structure-activity relationships in acaricidal 4H-1,3,4-oxadiazin-5(6H)-ones

Cited by 19 publications

References 8 publications

The Discovery of Bifenazate, a Novel Carbazate Acaricide

The Discovery of Bifenazate, a Novel Carbazate Acaricide

Synthesis and Biological Screening of 2-Substituted 5,6-Dihydro-5-oxo- 4H-1,3,4-oxadiazine-4-propanenitriles and of Their Intermediates

QSAR of 2,4-diphenyl-1,3-oxazolines for ovicidal activity against the two-spotted spider mite Tetranychus urticae

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