Structure-activity correlations of the insecticide Prolan and its analogs

Lee, An-Horng; Metcalf, Robert L.; Williams, John W.; Hirwe, Asha S.; Sanborn, James R.; Coats, Joel R.; Fukuto, T. R.

doi:10.1016/0048-3575(77)90003-7

Cited by 19 publications

(15 citation statements)

References 13 publications

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“…The van der Waals volume V, (5,10,11) and the Taft Es value (9,12) have been used to describe steric relationships of analogs (5). The STERIMOL constants have also been successfully employed in some QSAR analyses (10,11).…”

Section: Ddt-type Insecticidesmentioning

confidence: 99%

“…Lee et al. (9) determined that r of 1.5 to 2.0 for the aromatic substituents in a large series of prolan (2-nitropropanes) analogs conferred optimal toxicity (LD50 to ffies). A study of DDT analogs on cockroach nerve preparations indicated that higher values for the X and Y substituents resulted in higher neurotoxicity thresholds (less bioactivity), but all analogs tested were relatively lipophilic, with fT-values from -0.04 to 3.14 (10).…”

Section: Ddt-type Insecticidesmentioning

confidence: 99%

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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%

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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“…Data of Metcalf and Metcalf 1973, Lee et al 1977, Fahmy el al. 1978, Fukuto 1983, Umetsu 1984 reported (Welling et af.…”

mentioning

confidence: 99%

Insecticide metabolism and selective toxicity

Brooks

1986

Xenobiotica

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Current research is focused on means to improve the environmental acceptability and selective toxicity of existing classes of insecticides and the search for new and species selective modes of insecticidal action. The study of species differences in metabolism and its modulation by changes in chemical structure is a vital component of this effort. The importance of metabolism is illustrated by examples from the major classes of insect control chemicals, namely organophosphorus and carbamate insecticides, DDT, pyrethroids and insect growth regulators.

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“…Synthesis Pathway A 3-step reaction pathway was followed, using reactions previously described. Reactions I and II are described by Lee, et al, 1977. Reaction III was adapted from Tindall (1943;1946 In Reaction II, the crude carbinol was mixed with a 3-6 fold excess of the substituted benzene and dripped into cold acid mixture, with stirring.…”

mentioning

confidence: 99%

“…Other synthesis and structure-activity progress with diphenylnitroalkane insecticides include work by Jacob et al, 1951;Holan 1971a;1971b;Boehner et al, 1974;Kaufman and Strong, 1975;Lee et al, 1977;and Coats, 1983. Synthesis Pathway A 3-step reaction pathway was followed, using reactions previously described.…”

mentioning

confidence: 99%