Effective DDT analogs with altered aliphatic moieties. Isobutanes and chloropropanes

Coats, Joel R.; Metcalf, Robert L.; Kapoor, Inder P.

doi:10.1021/jf60212a023

Cited by 24 publications

(15 citation statements)

References 24 publications

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“…Specifically, alkyl, alkyloxy, alkylthio, and halogen groups are suitably lipophilic; and hydroxyl, amino, carboxy, sulfonyl, and nitro groups are too polar to allow penetration of the nerve sheath. The size of the X and Y substituents in active compounds are generally no larger than butyl or butoxy groups (3)(4)(5)(6).…”

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%

“…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%

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

Coats

1990

Environ Health Perspect

134

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“…Several theories for the interaction of DDT with nerve membranes have been proposed based on the three-dimensional structure of DDT and on structure-activity relationships of analogues. One example of these models is that proposed by Holan (1969), a model that was modified by Coats et al (1977) to account for activity of nonsymmetrical DDT analogues (Fig. 8-4; Fukuta, 1976).…”

Section: Physicochemical Interactions Of Ddt With Membrane Channelsmentioning

confidence: 99%

“…2.1.3). Impressive examples of analogue syntheses and evaluation are found in the reports by Coats et al (1977) and by Holan (1971). For reviews, see and .…”

Section: Analogues Of Ddtmentioning

confidence: 99%

Biochemistry of the Elemental Halogens and Inorganic Halides

Kirk

1991

314

216

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“…Electron donating substituents (at least one) on the rings also provide for greater insecticidal potency (Holan, 1969;Metcalf et al, 1971;Coats et al, 1977). Hence, the only 2-chloro-2-nitroethane synthesized by Skerrett and Woodcock lacked insecticidal activity, probably due to poor stability and low intrinsic toxicity, both resulting from the £,£ f -dichloro substituents.…”

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confidence: 99%