Insecticidal activity of 1,1,1-trichloro-2,2-bis(p-chlorophenyl)ethane (DDT) analogs

Abu-El-Haj, Sameer; Fahmy, M. A. H.; Fukuto, T. R.

doi:10.1021/jf60222a020

Cited by 7 publications

(2 citation statements)

References 7 publications

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“…Chloronitro analogs have been demonstrated to be quite active, but dichloronitroethanes are less effective (8). Polyfluoroalkane analogs were relatively inactive, probably due to excessive electronegativity in the Z group (13). An optimum a* is apparently 0.4 to 2.6.…”

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%

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

Coats

1990

Environ Health Perspect

134

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“…Notably, α -difluoromethylated diarylmethanes possess potent cytotoxic activity against HCT116 cells [ 53 , 54 ]. Moreover, we applied our protocol in the synthesis of a fluorinated analogue of the insecticide 1,1,1-trichloro-2,2-bis( p -chloro phenyl)ethane (DDT) [ 55 ]. Here, treatment of the trifluoromethylation product 3i with H 2 SO 4 followed by ethylation produced the DDT analogue 7b in 67% overall yield.…”

Section: Resultsmentioning

confidence: 99%

1,6-Nucleophilic Di- and Trifluoromethylation of para-Quinone Methides with Me3SiCF2H/Me3SiCF3 Facilitated by CsF/18-Crown-6

Chen,

Huang,

Liang

et al. 2024

Molecules

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The direct 1,6-nucleophilic difluoromethylation, trifluoromethylation, and difluoroalkylation of para-quinone methides (p-QMs) with Me3SiRf (Rf = CF2H, CF3, CF2CF3, CF2COOEt, and CF2SPh) under mild conditions are described. Although Me3SiCF2H shows lower reactivity than Me3SiCF3, it can react with p-QMs promoted by CsF/18-Crown-6 to give structurally diverse difluoromethyl products in good yields. The products can then be further converted into fluoroalkylated para-quinone methides and α-fluoroalkylated diarylmethanes.

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Suppression of Metabolic Resistance Through Chemical Structure Modification

Fukuto

Mallipudi

1983

Pest Resistance to Pesticides

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Insecticidal activity of 1,1,1-trichloro-2,2-bis(p-chlorophenyl)ethane (DDT) analogs

Cited by 7 publications

References 7 publications

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

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

1,6-Nucleophilic Di- and Trifluoromethylation of para-Quinone Methides with Me3SiCF2H/Me3SiCF3 Facilitated by CsF/18-Crown-6

Suppression of Metabolic Resistance Through Chemical Structure Modification

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