Dichlorvos
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Dichlorvos (2,2-dichlorovinyl dimethyl phosphate, commonly abbreviated as an DDVP) is an
organophosphate In organic chemistry, organophosphates (also known as phosphate esters, or OPEs) are a class of organophosphorus compounds with the general structure , a central phosphate molecule with alkyl or aromatic substituents. They can be considered ...
widely used as an
insecticide Insecticides are pesticides used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. The major use of insecticides is in agriculture, but they are also used in home and garden settings, i ...
to control household pests, in public health, and protecting stored products from insects. The compound has been commercially available since 1961. It has become controversial because of its prevalence in urban waterways and the fact that its toxicity extends well beyond insects. Since 1988, dichlorvos cannot be used as a plant protection product in the EU.


Use

Dichlorvos is effective against mushroom flies,
aphid Aphids are small sap-sucking insects in the Taxonomic rank, family Aphididae. Common names include greenfly and blackfly, although individuals within a species can vary widely in color. The group includes the fluffy white Eriosomatinae, woolly ...
s,
spider mite Spider mites are members of the family Tetranychidae, which includes about 1,200 species. They are part of the subclass Acari (mites). Spider mites generally live on the undersides of leaves of plants, where they may spin protective silk webs, a ...
s,
caterpillar Caterpillars ( ) are the larval stage of members of the order Lepidoptera (the insect order comprising butterflies and moths). As with most common names, the application of the word is arbitrary, since the larvae of sawflies (suborder ...
s,
thrips Thrips (Order (biology) , order Thysanoptera) are minute (mostly long or less), slender insects with fringed wings and unique asymmetrical mouthparts. Entomologists have species description , described approximately 7,700 species. They fly on ...
, and
whiteflies Whiteflies are Hemipterans that typically feed on the undersides of plant leaves. They comprise the family Aleyrodidae, the only family in the superfamily Aleyrodoidea. More than 1550 species have been described. Description and taxonomy The A ...
in greenhouses and in outdoor crops. It is also used in the milling and grain handling industries and to treat a variety of
parasitic worm Parasitic worms, also known as helminths, are a polyphyletic group of large macroparasites; adults can generally be seen with the naked eye. Many are intestinal worms that are soil-transmitted and infect the gastrointestinal tract. Other par ...
infections in animals and humans. It is fed to livestock to control
botfly Botflies, also known as warble flies, heel flies, and gadflies, are flies of the family Oestridae. Their larvae are internal parasites of mammals, some species growing in the host's flesh and others within the gut. '' Dermatobia hominis'' is ...
larvae in manure. It acts against insects as both a contact
poison A poison is any chemical substance that is harmful or lethal to living organisms. The term is used in a wide range of scientific fields and industries, where it is often specifically defined. It may also be applied colloquially or figurati ...
and an ingested poison. It is available as an
aerosol An aerosol is a suspension (chemistry), suspension of fine solid particles or liquid Drop (liquid), droplets in air or another gas. Aerosols can be generated from natural or Human impact on the environment, human causes. The term ''aerosol'' co ...
and soluble concentrate. It is also used in pet
flea collar An animal collar is a device that attaches to the neck of an animal to allow it to be harnessed or restrained. Types of collars Pet collar A piece of material put around the neck of certain pet animals, such as dogs, cats, or pigs, for co ...
s and "no-pest strips" in the form of a pesticide-impregnated plastic; this material has been available to households since 1964 and has been the source of some concern, partly due to misuse.


Properties

Dichlorvos is a colourless liquid with aromatic odour. Its density is at , melting point below and a boiling point of at 27
hPa The pascal (symbol: Pa) is the unit of pressure in the International System of Units (SI). It is also used to quantify internal pressure, stress, Young's modulus, and ultimate tensile strength. The unit, named after Blaise Pascal, is an S ...
. Dichlorvos is soluble in water.


Mechanism of action

Dichlorvos, like other organophosphate insecticides, inhibits
acetylcholinesterase Acetylcholinesterase (HUGO Gene Nomenclature Committee, HGNC symbol ACHE; EC 3.1.1.7; systematic name acetylcholine acetylhydrolase), also known as AChE, AChase or acetylhydrolase, is the primary cholinesterase in the body. It is an enzyme th ...
, associated with the nervous systems of insects. Evidence for other modes of action, applicable to higher animals, have been presented. It is claimed to damage
DNA Deoxyribonucleic acid (; DNA) is a polymer composed of two polynucleotide chains that coil around each other to form a double helix. The polymer carries genetic instructions for the development, functioning, growth and reproduction of al ...
of insects.


Regulation

The
United States Environmental Protection Agency The Environmental Protection Agency (EPA) is an independent agency of the United States government tasked with environmental protection matters. President Richard Nixon proposed the establishment of EPA on July 9, 1970; it began operation on De ...
has reviewed the safety data of dichlorvos several times. In 1995 a voluntary agreement was reached with the supplier, Amvac Chemical Corporation, which restricted the use of dichlorvos in many, but not all, domestic uses, all aerial applications, and other uses. Additional voluntary cancellations were implemented in 2006, 2008, and 2010. Major concerns focus on acute and chronic toxicity and the fact that this pesticide is prevalent in urban waterways. A 2010 study found that each 10-fold increase in urinary concentration of organophosphate metabolites was associated with a 55% to 72% increase in the odds of
ADHD Attention deficit hyperactivity disorder (ADHD) is a neurodevelopmental disorder characterised by symptoms of inattention, hyperactivity, impulsivity, and emotional dysregulation that are excessive and pervasive, impairing in multiple ...
in children. Between 2000 and 2013, thirty-one cases of acute dichlorvos pest strip-related illness were reported to the National Institute for Occupational Safety and Health (NIOSH) sentinel system. 65% of the 31 cases involved DDVP misuse contrary to instructions and safety labels. Common violations included pest strip use in occupied, poorly-ventilated living areas (e.g., kitchens, bedrooms), lack of skin protection, cutting and tearing strips, and using a heater and fan to accelerate vapor dissemination from strips.


Production

Dichlorvos can be produced by dehydrochlorinating
trichlorfon Metrifonate ( INN) or trichlorfon ( USAN) is an irreversible organophosphate acetylcholinesterase inhibitor. It is a prodrug which is activated non-enzymatically into the active agent dichlorvos. It is used as an insecticide. According to the US ...
in an aqueous alkali at 40-50 °C. It is also produced by the reaction of
trimethyl phosphate Trimethyl phosphate is the trimethyl ester of phosphoric acid. It is a colourless, nonvolatile liquid. It has some specialized uses in the production of other compounds. Production Trimethyl phosphate is prepared by treating phosphorus oxychlor ...
and chloral. As of 1990, it was produced in Argentina, Brazil, Germany, India, Israel, Japan, the Republic of Korea, Mexico, the USA, Switzerland, Sweden, Spain, and the Netherlands.


Environment

Dichlorvos enters the air, water, and soil when it is used and manufactured. It also can enter the environment when waste containing dichlorvos is disposed of in landfills. Dichlorvos is soluble in water, so it dissolves when it enters a body of water. Dichlorvos evaporates into the air easily, but is broken down by water vapor such as humidity. It does not bind to soil, but dichlorvos is broken down slower in soil than in the air. The broken down products are far less harmful than dichlorvos is. Dichlorvos is not stored in plants, animals, or humans.


Safety

People can be exposed to dichlorvos in the workplace by breathing it in, skin absorption, swallowing it, and eye contact. The
Occupational Safety and Health Administration The Occupational Safety and Health Administration (OSHA; ) is a regulatory agency of the United States Department of Labor that originally had federal visitorial powers to inspect and examine workplaces. The United States Congress established ...
(OSHA) has set the legal limit (
permissible exposure limit The permissible exposure limit (PEL or OSHA PEL) is a legal limit in the United States for exposure of an employee to a chemical substance or physical agents such as high level noise. Permissible exposure limits were established by the Occupational ...
) for dichlorvos exposure in the workplace as 1 mg/m3 over an 8-hour workday. The
National Institute for Occupational Safety and Health The National Institute for Occupational Safety and Health (NIOSH, ) is the List of United States federal agencies, United States federal agency responsible for conducting research and making recommendations for the prevention of work-related occ ...
(NIOSH) has set a
recommended exposure limit A recommended exposure limit (REL) is an occupational exposure limit that has been recommended by the United States National Institute for Occupational Safety and Health. The REL is a level that NIOSH believes would be protective of worker safety ...
(REL) of 1 mg/m3 over an 8-hour workday. At levels of 100 mg/m3, dichlorvos is
immediately dangerous to life or health The term immediately dangerous to life or health (IDLH) is defined by the US National Institute for Occupational Safety and Health (NIOSH) as exposure to airborne contaminants that is "likely to cause death or immediate or delayed permanent adver ...
(IDLH).


Treatment Technology

Different physicochemical methods have been developed for the removal of DDVP from contaminated environments, and microbial degradation is regarded as a promising method to solve several harmful residuals caused by DDVP. The biodegradation mechanism of many OPs has been studied deeply, especially for the methyl parathion, whose degradation genes and enzymes were cloned and purified. There is a need to select more useful strains, since only a few bacteria have been studied thoroughly in relation to the functional enzymes and genes.


Effects on humans

Since it is an
acetylcholinesterase inhibitor Acetylcholinesterase inhibitors (AChEIs) also often called cholinesterase inhibitors, inhibit the enzyme acetylcholinesterase from breaking down the neurotransmitter acetylcholine into choline and acetate, thereby increasing both the level an ...
, symptoms of dichlorvos exposure include weakness, headache, tightness in chest, blurred vision, salivation, sweating, nausea, vomiting, diarrhea, abdominal cramps, eye and skin irritation,
miosis Miosis, or myosis (), is excessive constriction of the pupil.Farlex medical dictionary
citing: ...
(pupil constriction), eye pain, runny nose,
wheezing A wheeze is a clinical symptom of a continuous, coarse, whistling sound produced in the respiratory airways during breathing. For wheezes to occur, part of the respiratory tree must be narrowed or obstructed (for example narrowing of the lower ...
,
laryngospasm Laryngospasm is an uncontrolled or involuntary muscular contraction ( spasm) of the vocal folds. It may be triggered when the vocal cords or the area of the trachea below the vocal folds detects the entry of water, mucus, blood, or other subst ...
,
cyanosis Cyanosis is the change of Tissue (biology), tissue color to a bluish-purple hue, as a result of decrease in the amount of oxygen bound to the hemoglobin in the red blood cells of the capillary bed. Cyanosis is apparent usually in the Tissue (bi ...
,
anorexia Anorexia nervosa (AN), often referred to simply as anorexia, is an eating disorder characterized by Calorie restriction, food restriction, body image disturbance, fear of gaining weight, and an overpowering desire to be thin. Individuals wit ...
,
muscle fasciculation A fasciculation, or muscle twitch, is a spontaneous, involuntary muscle contraction and relaxation, involving fine muscle fibers. They are common, with as many as 70% of people experiencing them. They can be benign, or associated with more seriou ...
, paralysis, dizziness,
ataxia Ataxia (from Greek α- negative prefix+ -τάξις rder= "lack of order") is a neurological sign consisting of lack of voluntary coordination of muscle movements that can include gait abnormality, speech changes, and abnormalities in e ...
, convulsions,
hypotension Hypotension, also known as low blood pressure, is a cardiovascular condition characterized by abnormally reduced blood pressure. Blood pressure is the force of blood pushing against the walls of the arteries as the heart pumps out blood and is ...
(low blood pressure), and
cardiac arrhythmia Arrhythmias, also known as cardiac arrhythmias, are irregularities in the heartbeat, including when it is too fast or too slow. Essentially, this is anything but normal sinus rhythm. A resting heart rate that is too fast – above 100 beat ...
s. It is also known to affect DNA replication in bacteria. Acute Effects Dichlorvos is irritating to the skin. The substance may affect the nervous system by inhibiting cholinesterase. The effects of exposure may be delayed but a high level could be fatal. Medical observation is indicated Tests involving acute exposure of rats, mice, and rabbits have demonstrated that dichlorvos has high to extremely acute toxicity from oral or dermal exposure and extremely acute toxicity from inhalation Long-Term Effects Prolonged contact with skin may cause dermatitis and skin sensitization. If drinking water contaminated by dichlorvos is ingested long-term it may cause oral cancer. Reproductive/Developmental Effects There is no information available on the reproductive or developmental effects of dichlorvos in humans. In studies conducted with rat models, birth defects in fetal rats were observed. Mouse models also demonstrated sperm abnormalities. However, studies with other animal subjects found no birth defects.


Trivia

Dichlorvos is mentioned in
John Brunner John Brunner may refer to: * Sir John Brunner, 1st Baronet (1842–1919), British industrialist and Liberal Member of Parliament * John L. Brunner (1929–1980), Pennsylvania politician * Sir John Brunner, 2nd Baronet (1865–1929), British Libe ...
's science fiction novel ''
The Sheep Look Up ''The Sheep Look Up'' is a 1972 dystopian science fiction novel by British author John Brunner, dealing with the deterioration of the environment in the United States. It was nominated for the 1972 Nebula Award for Best Novel. The novel is th ...
''. One of the book's many vignettes tells of a woman who nearly dies, having taken barbiturates and gone to sleep in a closed room where a fly-killing strip doused with the material was placed.


See also

*
Metrifonate Metrifonate ( INN) or trichlorfon ( USAN) is an irreversible organophosphate acetylcholinesterase inhibitor. It is a prodrug which is activated non-enzymatically into the active agent dichlorvos. It is used as an insecticide. According to th ...
(converts into dichlorvos) *
Naled Naled (Dibrom) is an organophosphate insecticide. Its chemical name is dimethyl 1,2-dibromo-2,2-dichloroethylphosphate. Naled is stable in anhydrous condition and must be stored away from light. It must also be stored under normal pressure and ...
(can convert into dichlorvos)


References


External links


Extension Toxicology Network - Pesticide Information Profiles - Dichlorvos
(last maintained 1996)


Australian Pesticides & Veterinary Medicines Authority Chemical Review Program - Dichlorvos

Material Safety Data Sheet (MSDS) for Dichlorvos
*
BBC News: Insecticide ban amid cancer fears
{{Acetylcholine metabolism and transport modulators Acetylcholinesterase inhibitors IARC Group 2B carcinogens Organochlorides Organophosphate insecticides