Structures and pesticidal activities of derivatives of dinitrophenols. VIII.—effects of substitution with C<sub>5</sub> to C<sub>13</sub>‐s‐alkyl groups and of esterification on the acaricidal activity of dinitrophenols

Pianka, M.; Edwards, J. D.

doi:10.1002/jsfa.2740190202

Cited by 8 publications

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References 4 publications

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“…While studying the structure-activity relationship for drugs, Hansch (4) proposed the correlation equation (6): log LD50 = C7T2 + Dr + Eo-+ F (6) where ir is defined as earlier, oc is the Hammett constant, and C, D, E, and F are constants. Attempts were made to test such a correlation.…”

Section: Discussionmentioning

confidence: 99%

Chemical structure and properties of selected benzene compounds in relation to biological activity.

Freed¹,

Haque²

1976

Environ Health Perspect

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Four fundamental physical parameters of series of benzene derivatives were studied to ascertain correlations with biological activity. These included octanol/water coefficient, vapor pressure, infrared absorption (out-of-plane C-H vibration), and the pi values. Each physicochemical constant exhibited a partial correlation with biological activity suggesting that each played a role. It was presumed that more precise and specific data on the biological activity would have permitted a better correlation. It is postulated that the biological activity of a compound is due to the sum of such physicochemical factors as: partition coefficient, molecular geometry and spatial orientation, electronic characteristics of the molecular orbitals, and vibrational-rotational frequencies of constituent groups.

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Section: Discussionmentioning

confidence: 99%

Chemical structure and properties of selected benzene compounds in relation to biological activity.

Freed¹,

Haque²

1976

Environ Health Perspect

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Structures and pesticidal activities of derivatives of dinitrophenols. IX.—Effects of substitution of dinitrophenols with C₄ to C₁₃ α‐branched alkyl groups and of esterification on the eradication of apple mildew

Pianka¹,

Sweet

1968

J Sci Food Agric

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The eradication of apple mildew caused by Podosphaera leucotricha (Ell. and Everh.) Salm. with 2-(C4 to C13 a-branched alkyl)-4,6-dinitrophenols and 4424 to Cln a-branched alkyl)-2,6-dinitrophenols was examined. 4-(l-Ethylbutyl)-and most 4-(C7 to Cla a-branched alkyl)-2,6-dinitrophenols were significantly more active than their 2-alkyl-4,6-dinitrophenol analogues. Compounds containing 4-C13 alkyls did not show significant activity. Activity generally increased as the a-alkyl branch lengthened.Methyl carbonates did not show lower activity than the parent phenols, but esterification of 4-(C12 or c 1 3 a-branched a.lkyl)-2,6-dinitrophenols to ethyl carbonates or crotonates gave compounds with reduced activity. Methyl-, ethyl-or isopropyl-carbonates and crotonates of 4-(1-ethylhexyl)-2,6-dinitrophenol had much higher activity than the corresponding esters of the 4-(l-methylheptyl) isomer or of 2-(l-ethylhexyl)-4,6-dinitrophenol. Compounds containing long ester chains (C7 or CS) had less activity than 4-( 1 -ethylhexyl)-2,6-dinitrophenol.0-Methylation produced compounds with less activity than the parent 4-(l-ethylhexyl)-and 4-(l-propylpentyl)-2,6-dinitrophenols.

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Structures and pesticidal activities of derivatives of dinitrophenols. X.—Effects of substitution of dinitrophenols with C₃ to C₁₃ α‐branched alkyl groups and of esterification on the eradication of barley mildew

Pianka

Sweet

1968

J Sci Food Agric

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The studies of the eradication of barley mildew due to Erysiphe graminis Mbat with alkyldinitrophenols reported earlier1 were continued. The degree of eradication was highest with 44C9 a-branched alky1)-2,6-dinitrophenols. 4-Alkyl-2,6-dinitrophenols containing a heptyl or higher alkyl branch were significantly less active, and compounds containing the Clz or c 1 3 alkyls were not active since the most compact of the Ciz a-branched alkyls is 1-pentylheptyl. 2-(l-Methylheptyl)-and 2-(l-propylpentyl)-4,6-dinitrophenols had high activity, but their esters showed reduced activity. Esterification of 4-(a-branched alkyl)-2,6-dinitrophenols to methyl carbonates did not affect the activity shown by the compounds, but when certain 4-Go and C11 alkyl-2,6-dinitrophenols were esterified to ethyl carbonates the activity of the products was reduced. Also activity was diminished by conversion of some 4-CS and Cio alkyl-2,6-dinitrophenols to crotonates. Whereas the methyl-and ethyl-carbonates of 4-(1-ethylhexyl)-2,6-dinitrophenol gave consistently high degrees of eradication of barley mildew, the performance of the crotonate of this phenol was not consistent. Lower aliphatic esters of the active Cs-alkyl phenols were themselves active. Esterification of 4-(1-ethylhexyl)-2,6-dinitrophenol to the benzoate, isopropyl carbonate or S-methyl thiolocarbonate gave compounds with substantially reduced activity. 2-t-Butyl-4,6-dinitrophenyl or 4-t-butyl-or t-octyl-2,6-dinitrophenyl esters gave little or no significant eradication.

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Structures and pesticidal activities of derivatives of dinitrophenols. VIII.—effects of substitution with C₅ to C₁₃‐s‐alkyl groups and of esterification on the acaricidal activity of dinitrophenols

Cited by 8 publications

References 4 publications

Chemical structure and properties of selected benzene compounds in relation to biological activity.

Chemical structure and properties of selected benzene compounds in relation to biological activity.

Structures and pesticidal activities of derivatives of dinitrophenols. IX.—Effects of substitution of dinitrophenols with C₄ to C₁₃ α‐branched alkyl groups and of esterification on the eradication of apple mildew

Structures and pesticidal activities of derivatives of dinitrophenols. X.—Effects of substitution of dinitrophenols with C₃ to C₁₃ α‐branched alkyl groups and of esterification on the eradication of barley mildew

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Structures and pesticidal activities of derivatives of dinitrophenols. VIII.—effects of substitution with C5 to C13‐s‐alkyl groups and of esterification on the acaricidal activity of dinitrophenols

Cited by 8 publications

References 4 publications

Chemical structure and properties of selected benzene compounds in relation to biological activity.

Chemical structure and properties of selected benzene compounds in relation to biological activity.

Structures and pesticidal activities of derivatives of dinitrophenols. IX.—Effects of substitution of dinitrophenols with C4 to C13 α‐branched alkyl groups and of esterification on the eradication of apple mildew

Structures and pesticidal activities of derivatives of dinitrophenols. X.—Effects of substitution of dinitrophenols with C3 to C13 α‐branched alkyl groups and of esterification on the eradication of barley mildew

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Structures and pesticidal activities of derivatives of dinitrophenols. VIII.—effects of substitution with C₅ to C₁₃‐s‐alkyl groups and of esterification on the acaricidal activity of dinitrophenols

Structures and pesticidal activities of derivatives of dinitrophenols. IX.—Effects of substitution of dinitrophenols with C₄ to C₁₃ α‐branched alkyl groups and of esterification on the eradication of apple mildew

Structures and pesticidal activities of derivatives of dinitrophenols. X.—Effects of substitution of dinitrophenols with C₃ to C₁₃ α‐branched alkyl groups and of esterification on the eradication of barley mildew