DDT

Kaloyanova FP, El Batawi MA Human Toxicology of Pesticides. Boca Raton, FL, CRC Press, 1991 

Misra UK, Nag D, Krishna M A study of cognitive functions in DDT sprayers. Ind Health 22 199-206, 1984 

Stone TT, Gladstone L DDT (Dichlorodiphenyl-trichloroethane) (clinical note). JAMA 145 1342-1342, 1951 

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CCls CHO. A colourless oily liquid with a pungent odour b.p. 98°C. Manut actured by the action of chlorine on ethanol it is also made by the chlorination of ethanal. When allowed to stand, it changes slowly to a white solid. Addition compounds are formed with water see chloral hydrate), ammonia, sodium hydrogen sulphite, alcohols, and some amines and amides. Oxidized by nitric acid to tri-chloroethanoic acid. Decomposed by alkalis to chloroform and a methanoate a convenient method of obtaining pure CHCI3. It is used for the manufacture of DDT. It is also used as a hypnotic. 

M.p. I08-5 C. Ordinary DDT contains about 15% of the 2,4 -isomer, and is prepared from chloral, chlorobenzene and sulphuric acid. It is non-phytotoxic to most plants. It is a powerful and persistent insecticide, used most effectively to control mosquitoes in countries where malaria is a problem. It is stored in the bodies of animals and birds. 

DDT resistant insects have the ability to convert DDT to a less toxic substance called DDE The mass spectrum of DDE shows a cluster of peaks for the molecular ion at m/z 316 318 320 322 and 324 Suggest a reasonable structure for DDE... 

The value of insecticides in controlling human and animal diseases spread by insects has been dramatic. It has been shown that between 1942 and 1952, the use of DDT in pubHc health measures to control the mosquito vectors of malaria and the human body louse vector of typhus saved five million hves and prevented 100 million illnesses (4). Insecticides have provided the means to control such important human diseases as filariasis transmitted by Culex mosquitoes and onchocerciasis transmitted by Simulium blackflies. 

Mode of Action. DDT and its analogues specifically affect the peripheral sense organs of insects and produce violent trains of afferent impulses that result in hyperactivity, convulsions, and paralysis. Death results from metaboHc exhaustion and the production of an endogenous neurotoxin. The very high lipophilic nature of these compounds faciUtates absorption through the insect cuticle and penetration to the nerve tissue. The specific site of action is thought to be the sodium channels of the axon, through inhibition of Ca " ATPase. 

DDT is slowly converted in vivo by reductive dechlorination to DDD and by further dechlorinations to 4,4 -dichlorodiphenylacetic acid [83-05-6] (DDA), the predominant excretory metaboUte. Anaerobically, it may form 4,4 -dichlorodiphenyiacetonitrile [20968-04-1] (DDCN). However, most DDT that enters the environment is sequestered as DDE, which is ubiquitously present in the body Hpids of invertebrate and vertebrate animals. In humans. 

DDT is stored ia body fats and is secreted ia milk as DDT, DDD, and DDE with traces of their o,p -isonieis. Levels of these compounds ia the body tissues of United States inhabitants have declined slowly from ca 12 ppm ia 1970 as a result of sharply curtailed usage. 

DDT is highly toxic to fish (LC q for trout and blue gill, 0.002—0.008 ppm), and it is only moderately toxic to birds (oral LD q mallard 1300 and pheasant >2240 mg/kg). However, widespread bird kills have resulted from bioconcentration of DDT through food chains, ie, from fish or earthworms. A significant environmental problem has resulted from the specific effects of DDE on eggshell formation in raptorial birds where accumulation has caused decreases in shell thickness of 10—15%, resulting in widespread breakage. 

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