Structure-Activity for Uptake and Toxicity of DDT-Type Insecticides Utilizing an NMR Method for Estimating Σ*

Coats, Joel R.; Williams, John W.; Chang, Carolyn; Lee, An-Horng; Metcalf, Robert L.

doi:10.1897/1552-8618(1989)8[45:sfuato]2.0.co;2

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“…An optimum a* is apparently 0.4 to 2.6. The a* value has been used to demonstrate the importance ofthe aliphatic moiety electronegativity in mammalian toxicity QSAR as well with an optimum a apparent at 1.5-2.5 (14). In summary, the current QSAR status entails a very general hydrophobicity requirement, relatively strict steric conditions, and an optimum for electronic character, especially in the aliphatic moiety.…”

Section: Ddt-type Insecticidesmentioning

confidence: 99%

Mechanisms of toxic action and structure-activity relationships for organochlorine and synthetic pyrethroid insecticides.

Coats

1990

Environ Health Perspect

134

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The mechanisms and sites of action of organochlorine (DDT-types and chlorinated alicyclics) and synthetic pyrethroid insecticides are presented with discussion of symptoms, physiological effects, and selectivity. The structural requirements for toxicity are assessed, and structure-activity relationships are considered for each subclass. Lipophilicity is important for all the groups because it facilitates delivery of these neurotoxicants to the site of action in the nerve. Steric factors including molecular volume, shape, and isomeric configuration greatly influence toxicity. Electronic parameters also have been demonstrated to affect biological activity in some of the groups of insecticides, e.g., Hammett's sigma and Taft's sigma * as indicators of electronegativity. New synthetic pyrethroids continue to be developed, with varied structures and different physicochemical and biological properties. Environmental Health Perepectives Vol. 87, pp. 255-262, 1990 Mechanisms of Toxic Action and StructureActivity Relationships for Organochiorine and Synthetic Pyrethroid Insecticides by Joel R. Coats* The mechanisms and sites of action of organochlorine (DDT-types and chlorinated alicyclics) and synthetic pyrethroid insecticides are presented with discussion of symptoms, physiological effects, and selectivity. The structural requirements for toxicity are assessed, and structure-activity relationships are considered for each subclass. Lipophilicity is important for all the groups because it facilitates delivery of these neurotoxicants to the site of action in the nerve. Steric factors including molecular volume, shape, and isomeric configuration greatly influence toxicity. Electronic parameters also have been demonstrated to affect biological activity in some of the groups of insecticides, e.g., Hammett's a and Taft's a* as indicators of electronegativity. New synthetic pyrethroids continue to be developed, with varied structures and different physicochemical and biological properties.

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Section: Ddt-type Insecticidesmentioning

confidence: 99%