DDT

Dichlorodiphenyltrichloroethane (DDT) inhibits carbonic anhydrase at the amount of micrograms at which other inhibitors are inactive.

From: Encyclopedia of Analytical Science (Second Edition), 2005

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DDT (Dichlorodiphenyltrichloroethane)

S.A. Burr, in Encyclopedia of Toxicology (Third Edition), 2014

Toxicokinetics

DDT is hydrophobic and lipophilic requiring an organic solvent (e.g., oil or fat) as a vehicle. Gastrointestinal absorption is slow with symptoms taking several hours to develop. DDT is metabolized slowly by liver microsomal enzymes initially dehydrochlorinating DDT to DDE and reducing to DDD. In some rodents (rats and hamsters, but not mice) DDT induces microsomal liver enzymes to promote metabolism. DDD is converted to 2,2-bis(p-chlorophenyl)acetic acid (DDA) via hydroxylation to an acyl chloride intermediate followed by hydrolysis. DDA is the main route for DDT elimination, mostly being excreted in bile and some in urine. Lactating mothers may excrete up to 10% of DDT doses via breast milk. DDT accumulates in all tissues but the highest levels are in adipose tissue. Coexposure to DDT and dieldrin results in more DDT storage and less dieldrin storage than individual exposures. DDE is more strongly bound in tissue than DDT. The half-life of DDT in humans is 3–6 years and twice as long for DDE. Starvation mobilizes fat reserves, increasing nervous system deposition and neurotoxic effects.

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DDT and Related Compounds

In Handbook of Pollution Prevention and Cleaner Production: Best Practices in the Agrochemical Industry, 2011

6.1 Introduction

Dichlorodiphenyltrichloroethane (hereinafter referred to as DDT) is one of the most widely used and well-studied pesticides ever synthesized. Commercial grade DDT also contains the compounds dichlorodiphenyldichloroethylene (DDE) and dichlorodiphenyldichloroethane (DDD), both of which are also metabolites of DDT and have similar chemical properties (see Table 6.1). (Unless otherwise noted, DDT, DDE, and DDD will refer to p,p′-DDT, p,p′-DDE, and p,p′-DDD, respectively.) DDT is an organochlorine compound that was introduced for commercial use in 1945 and was used heavily in populated areas for vector control and in agriculture for pest control. DDT is an extremely persistent compound due to its near insolubility in water and tendency to bioaccumulate in fatty tissue and biomagnify throughout trophic levels. By 1972, DDT use was banned in the United States and worldwide production and use began to decrease as well. Despite the injurious impacts on the environment and potential adverse health effects in humans, DDT is still produced; in fact global production actually appears to be increasing (UNEP, 2008).

Table 6.1. Chemical Properties of DDT, DDE, and DDD (ATSDR, 2002)

Property
Name p,p′-DDT p,p′-DDE p,p′-DDD
Other names Dichlorodiphenyltrichloroethane; 1,1′- (2,2,2-trichloroethylidene) bis(4-chlorobenzene); 1,1,1-Trichloro-2,2-bis(4-chlorophenyl)ethane Dichlorodiphenyldichloroethylene; 1,1′-(2,2-dichloroethylidene)bis(4-chlorobenzene); 1,1-dichloro-2,2-bis(4-chlorophenyl)ethylene Dichlorodiphenyldichloroethane; 1,1-bis (4-chlorophenyl)-2,2-dichloroethane; 1,1-dichloro-2,2-bis(4-chlorophenyl)ethane
Chemical structure
CAS registry number 50-29-3 72-55-9 72-54-8
Chemical formula C14H9C5 C14H8C4 C14H10C4
Physical state Crystals or powder Crystals Crystals or powder
Color White White White
Odor Weak aromatic or odorless N/A Odorless
Molecular weight (g/mol) 354.49 318.03 320.05
Density (g/cm3) 0.98–0.99 N/A 1.385
Solubility in water (mg/L) 0.025 (at 25°C) 0.12 (at 25°C) 0.090 (at 25°C)
Miscible organic solvents Ethyl ether, acetone Lipids, many organic solvents N/A
Vapor pressure (torr) 1.60×10−7 (at 20°C) 6.0×10−6 (at 25°C) 1.35×10−6 (at 25°C)
Henry's Law constant (atm-m3/mol) 8.3×10−6 2.1×10−5 4.0×10−6
Log KOC 5.18 4.70 5.18
Log KOW 6.91 6.51 6.02
Metling point (°C) 109 89 109–110
Boiling point (°C) Decomposes 336 350
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Pesticides and removal approaches

Abdelkrim Azzouz, ... Mohammed El-Akhrass, in Sorbents Materials for Controlling Environmental Pollution, 2021

17.2.3 Dichlorodiphenyltrichloroethane

DDT is a colorless solid belonging to the organochlorine family with a powerful capacity to kill insects. Conventional synthesis procedures usually result in the predominant formation of p,p′-DDT, denoted as DDT, and the two other isomers, namely o,o′-DDT and o,p′-DDT. It was first synthesized in 1874 with a chemical structure devoid of hydrophilic groups that confers insolubility in water. This explains somehow the relatively long half-life of 2–15 years in soils, versus 28–56 days in aqueous media where DDT occurs rather as solid suspension or emulsion in diverse organic solvents.

Up the 1970s, DDT became the most used insecticide, before being banned in some countries when certain negative impacts were noticed on the environment. In 1972, DDT was first banned in the United States when harmful character on human health was noticed, more particularly as a potential cause of some cancers, but later this insecticide has been banned by 158 countries.

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Pesticides

Paul E. Rosenfeld, Lydia G.H. Feng, in Risks of Hazardous Wastes, 2011

11.2.1 DDT

Dichlorodiphenyltrichloroethane (DDT) is one of the most widely used and well-studied pesticides ever synthesized. DDT was introduced for commercial use in 1945 and was used heavily in populated areas for vector control and in agriculture for pest control.

In 1946, the US Fish and Wildlife Service published a report warning that DDT can cause damage to fish and aquatic invertebrates (USFWS, 1946). Since then, numerous studies have shown that DDT causes eggshell thinning and reproductive damage in birds and toxicity to fish as well (Fry, 1995; Henderson et al., 1959). Because DDT accumulates in fatty tissue, it has a tendency to biomagnify through trophic levels and can be found in birds in concentrations of up to 10 million times higher than the concentration of DDT in water in which the birds feed (USFWS, 2009). By 1972, DDT use was banned in the United States and worldwide production and use began to decrease as well.

Despite the injurious impacts on the environment and potential adverse health effects in humans, DDT is still produced; in fact global production actually appears to be increasing (UNEP, 2008). A large quantity of the DDT produced today is used as an intermediate in the synthesis of the acaricide dicofol (trade name: Kelthane). In 1986, the EPA temporarily cancelled registration of dicofol because large quantities of DDT were ending up in the final product. A recent study of dicofol formulations in China found that dicofol might be a significant contributor to DDT pollution in China and could also be responsible for the unchanging DDT levels found in China more than two decades since technical DDT was banned (Qiu et al., 2005).

In the US, DDT can still be found as a residue in food products. The food sources with the highest DDT concentrations are meat, fish, poultry, and dairy products. DDT residues in food have declined since it was banned but because of the extreme persistence of DDT in the environment, it is anticipated that low levels of residues will be present in food products for decades (ATSDR, 2002). In the 1999 FDA Total Diet Study, DDT was found in 255 out of 1,040 (22%) items analyzed (FDA, 1999).

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Chlorinated Hydrocarbons

J.W. Farrington, in Encyclopedia of Ocean Sciences, 2001

DDT

DDT is not a naturally occurring compound. It was first synthesized in 1874 and its insecticidal properties were discovered in 1939. Initial large use of DDT as an insecticide began in 1944 and continued into the late 1960s. It was used with success against vectors of human diseases such as malaria and with dramatic effect in agriculture around the world in controlling insect pests. The environmental problems associated with DDT in terms of adverse effects on nontarget organisms such as birds were brought to popular attention in the highly influential book ‘Silent Spring’ by Rachael Carson in 1962. Further studies of DDT in the mid 1960s to early 1970s documented the presence of DDT and several other chlorinated pesticides in marine organisms at all major sectors in the marine food web. Analyses of samples from organisms dwelling in the deep part of the oceans, for example 4000–5000 m depth in the North Atlantic, and from Arctic and Antarctic marine ecosystems contained measurable concentrations of DDT. Evidence of adverse effects on nontarget terrestrial, freshwater and marine organisms, especially birds, resulted in curtailed use or bans on the use of DDT in several developed countries in the early 1970s. The legacy of past releases to the environment is present in marine ecosystems in the form of measurable concentrations of DDT compounds. In addition, the use of DDT continues in a few countries.

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DDT (Dichlorodiphenyltrichloroethane)

Benny L. Blaylock, in Encyclopedia of Toxicology (Second Edition), 2005

Environmental Fate

DDT is highly environmentally stable with a reported half-life of between 2 and 15 years. The insecticide is immobile in most soils and loss is the result of runoff, volatilization, photolysis, and biodegradation. Due to its extremely low solubility in water, DDT will be retained to a greater degree by soils and soil fractions. However, due to its persistence, DDT may be able to eventually leach into groundwater, especially in soils with little soil organic matter.

DDT may reach surface waters primarily by runoff, atmospheric transport, drift, or by direct application (e.g., to control mosquito-borne malaria). The reported half-life for DDT in the water environment is 56 days in lake water and ∼28 days in river water. The main pathways for loss are volatilization, photodegradation, adsorption to waterborne particulates, and sedimentation. Aquatic organisms, as noted above, also readily take up and store DDT and its metabolites.

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Volume 5

Amir Miodovnik, in Encyclopedia of Environmental Health (Second Edition), 2019

Dichlorodiphenyldichloroethylene, Dichlorodiphenyltrichloroethane, and Hexachlorobenzene

DDT is probably best known for its effect on the reproductive cycle of predatory birds such as peregrine falcons, osprey, and eagles as depicted in Rachel Carson’s book, Silent Spring (1962). Data regarding neurodevelopmental toxicities of DDT, dichlorodiphenyldichloroethylene (DDE, the major persistent metabolite of DDT), or HCB in humans are limited. A few studies have demonstrated associations of prenatal DDE and DDT exposures with poor infant neuromuscular and cognitive development and, for DDT, subsequent childhood cognition through age 4 years. HCB was used as a fungicide in the United States until it was discontinued in 1984; it continues to be formed during waste incineration or as a byproduct in the manufacture of pesticides. Prenatal HCB exposures have been associated with adverse behaviors, including ADHD-related symptoms, in heavily exposed Spanish children but not in a US study of children.

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Environmental fate of organic pollutants and effect on human health

Manita Thakur, Deepak Pathania, in Abatement of Environmental Pollutants, 2020

2.1.1 Dichlorodiphenyltrichloroethane

DDT is a crystalline chemical compound, which is a colorless, tasteless, hydrophobic, odorless, and low water-soluble compound but shows good solubility in organic solvents, fats, and oils. It has been widely used in World War Second to protect soldiers and civilians from typhus and malaria spread by insects (Alvarez et al., 2003; Santacruz et al., 2005; Qu et al., 2015; Tian et al., 2009a,b; Pang et al., 2010). After this, DDT was continued to be used against mosquitoes to control malaria and sprayed on agricultural crops, mostly cotton. Owing to its high persistence, it can remain 50% in the soil up to 10–15 years after application. DDT residues have been found all over the place, even its residual has been found in the Arctic because of its wide applicability.

DDT is readily adsorbed to soils, sediments, and can act as sinks and long-term sources of exposure. It is hydrophobic in nature; therefore in aquatic ecosystems, DDT and its constituents are absorbed by aquatic organisms. However, a little adsorbed on suspended particles send off little DDT dissolved in the water (Kang et al., 2016; Tian et al., 2009a,b; Han et al., 2016; Neerja et al., 2016). Its breakdown metabolites such as dichlorodiphenyldichloroethylene (DDE) and dichlorodiphenyldichloroethane (DDD) are highly persistent and have similar chemical and physical properties. DDT and its breakdown products have been transported from warmer areas to the Arctic because of global distillation and accumulate in the food web.

DDT can bioaccumulate in predatory birds because of its lipophilic properties. DDT is very toxic to living organisms including marine animals such as sea shrimp, crayfish, daphnids, and many species of fish. DDT, DDE, and DDD are stored mainly in body fat and resistant to metabolism in humans. It also causes eggshell thinning in birds and a major reason for the decline of the peregrine falcon, bald eagle, brown pelican, and osprey (Gebresemati and Soha, 2016; Neitsch et al., 2016; Balawejder et al., 2016). DDT is an endocrine disruptor and carcinogen to humans. DDE acts as a weak androgen receptor antagonist but not as an estrogen.

DDT is highly carcinogenic, toxic, and hazardous but indirect exposure is relatively nontoxic for humans. Chronic exposure of DDT can affect reproductive capabilities, embryo or fetus, and breast cancer.

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Biodiversity

E.L. Thompson, in Encyclopedia of the Anthropocene, 2018

Dichlorodiphenyltrichloroethane

DDT is an organochlorine insecticide. It was synthesized in the late 1870s and discovered as an insecticide in late 1930. DDT was used globally in the 1940s and 1950s to eradicate malaria, and following that, for 20 years, it was used extensively in agriculture. The use was not just on a commercial scale as the application of DDT was transferred into household insect eradication products. DDT has had major impacts on wildlife, especially marine organisms and bird species. It is thought to be responsible for egg shell thinning and subsequent embryo death in many birds of prey species, which has led to the decline of these species. Its general commercial use has been banned worldwide; however, it is still known to be used in India and North Korea. DDT is readily absorbed into soil and adsorbed onto sediment and is therefore known as a persistent organic pollutant (POP), meaning it is resistant to environmental degradation. Apart from being bound up in soil and sediment, it is able to travel long distances from its original source and be accumulated in tissue of organisms, enabling its trophic transfer through food chains.

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Analytical Methodology of POPs

Eric J. Reiner, ... Jean-François Focant, in Environmental Forensics for Persistent Organic Pollutants, 2014

3.10.3 OC Pesticides

DDT was first synthesized in 1874, but not used as a pesticide until 1939. DDT was used to control mosquitoes for malaria and lice for typhus during the Second World War [80]. DDT and other OCs were used extensively in 1940s and 50s to control pests and to increase crop yields. Prior to the development of ECD, DDT was analyzed using a colorimetric method [80]. In this method, DDT and degradation products (dichlorodiphenyldichloroethylene (DDE) and dichlorodiphenyldichloroethane (DDD)) were subjected to fuming nitric acid to produce a tetranitro-DDT complex that is reacted with a sodium methylate-methanol reagent. Levels as low as 10 μg/g (~10 ppm) could be detected. Significantly greater sensitivity and selectivity was achieved with GC–ECD enabling the analysis of all of the OCs. The majority of OCs were banned in the 1970s and globally by the Stockholm Convention in 2001 and are now rarely detected in samples. Lindane was used until 2009 when it was added to the Stockholm Convention list, Endosulphan is still produced in China and India and used in restricted applications. DDT was originally banned, but is now in restricted use for mosquito control in areas like Africa where malaria is still present and for the production of dicofol a less bioaccumulative form of DDT. Many of the other OC pesticides are now very rarely detected in environmental samples. As indicated above, PCBs and OC pesticides are often analyzed together. Dual column GC–ECD is still used in many applications which requires extract fractionation on Florisil® or silica. GC–MS or GC×GC–ECD can be used without fractionation [40,43]. Carbon-13 standards are available for all of the common OC pesticides but are typically not used because they are expensive. Isotope dilution using carbon-13 labeled standards and GC–HRMS is used in litigation when sensitivity, selectivity, and accuracy are required. Many of the OC pesticides degrade by dechlorination. Dirty GC injector liners can catalyze the degradation, therefore it is important to regularly assess and clean liners.

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