Triazofos is a

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

used in

acaricide Acaricides are pesticides that kill members of the arachnid subclass '' Acari'', which includes ticks and mites. Acaricides are used both in medicine and agriculture, although the desired selective toxicity differs between the two fields. Termi ...

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 ...

s, and

nematicide A nematicide is a type of chemical pesticide used to kill plant- parasitic nematodes. Nematicides have tended to be broad-spectrum toxicants possessing high volatility or other properties promoting migration through the soil. Aldicarb (Temik), a ...

History

Triazofos has been registered in the

Federal Office of Consumer Protection and Food Safety The Federal Office of Consumer Protection and Food Safety (BVL) is an agency of the Government of Germany, German government that comes under Federal Ministry of Food and Agriculture (Germany), Federal Ministry of Food and Agriculture (BMEL). It ...

since 1975 and authorized as an

in the EU until 31 December 2004 (Commission Regulation No 2076/2002). As of 25 July 2003 it was revoked under Commission Regulation No 1336/2003. The production of triazofos began in the 1980s as a Hoechst patent by the company

Bayer Bayer AG (English: , commonly pronounced ; ) is a German multinational pharmaceutical and biotechnology company and is one of the largest pharmaceutical companies and biomedical companies in the world. Headquartered in Leverkusen, Bayer' ...

. In 2011

announced termination of the sale of this product, due to its

poisonous 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 ...

properties.

Synthesis and available forms

Synthesis

Triazofos can be synthesized through various reactions. A method of manufacturing triazofos produces the substance in the presence of

triethylamine Triethylamine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N. Like triethanolamine and the tetraethylammonium ion, it is often abbreviated TEA. It is a colourless volatile liquid with a strong fishy odor remini ...

by reacting 1-phenyl-3-hydroxy-1H-1,2,4-triazole suspended in

acetone Acetone (2-propanone or dimethyl ketone) is an organic compound with the chemical formula, formula . It is the simplest and smallest ketone (). It is a colorless, highly Volatile organic compound, volatile, and flammable liquid with a charact ...

with diethoxythiophosphoryl chloride.Toxnet. (Undated). HSDB: Triazophos: Methods of Manufacturing. Retrieved on March 10th 2017, from website: https://www.nlm.nih.gov/toxnet/index.html Another method produces the substance by the reaction of

phenylhydrazine Phenylhydrazine is the chemical compound with the formula . It is often abbreviated as . It is also found in edible mushrooms. Properties Phenylhydrazine forms monoclinic prisms that melt to an oil around room temperature which may turn yellow ...

with

Sodium cyanate Sodium cyanate is the inorganic compound with the formula NaOCN. A white solid, it is the sodium salt of the cyanate anion. Structure The anion is described by two resonance structures: The salt adopts a body centered rhombohedral crystal latt ...

formamide Formamide is an amide derived from formic acid. It is a colorless liquid which is miscible with water and has an ammonia-like odor. It is chemical feedstock for the manufacture of sulfa drugs and other pharmaceuticals, herbicides and pesticides, ...

and O,O-diethyl phosphorochlorothioate using

cyanate The cyanate ion is an anion with the chemical formula . It is a resonance of three forms: (61%) ↔ (30%) ↔ (4%). Cyanate is the derived anion of isocyanic acid, H−N=C=O, and its lesser tautomer cyanic acid (a.k.a. cyanol), H−O−C� ...

additions,

condensation Condensation is the change of the state of matter from the gas phase into the liquid phase, and is the reverse of vaporization. The word most often refers to the water cycle. It can also be defined as the change in the state of water vapor ...

and

dehydrochlorination In chemistry, dehydrohalogenation is an elimination reaction which removes a hydrogen halide from a substrate. The reaction is usually associated with the synthesis of alkenes, but it has wider applications. Dehydrohalogenation from alkyl halide ...

. An improved process for manufacturing triazofos uses

phase transfer catalyst In chemistry, a phase-transfer catalyst or PTC is a catalyst that facilitates the transition of a reactant from one phase into another phase where reaction occurs. Phase-transfer catalysis is a special form of catalysis and can act through homog ...

to achieve higher yields and purity. By comprising substituted 1-phenyl 3-hydroxy-1, 2, 4-triazole with 0, -diethylthiophosphoryl chloride in the presence of acide scavengers and 0.2% to 2.0% phase transfer catalyst at a temperature between 20-45 degrees

Celsius The degree Celsius is the unit of temperature on the Celsius temperature scale "Celsius temperature scale, also called centigrade temperature scale, scale based on 0 ° for the melting point of water and 100 ° for the boiling point ...

in a suitable solvent like

water Water is an inorganic compound with the chemical formula . It is a transparent, tasteless, odorless, and Color of water, nearly colorless chemical substance. It is the main constituent of Earth's hydrosphere and the fluids of all known liv ...

. Followed by cooling and separating/extracting the aqueous layer from the organic layer by using a

solvent A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...

such as

xylene In organic chemistry, xylene or xylol (; IUPAC name: dimethylbenzene) are any of three organic compounds with the formula . They are derived from the substitution of two hydrogen atoms with methyl groups in a benzene ring; which hydrogens are su ...

toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon with the chemical formula , often abbreviated as , where Ph stands for the phenyl group. It is a colorless, water Water is an inorganic compound with the c ...

methylene dichloride Methylene may refer to: * Methylene group or methylene bridge (CH2< or equivalently −CH2−), a part of a molecule connected to the rest of the molecule by two single bonds. * An older name for methylidene group (=CH2), a part of a molecule ...

for complete recovery of at least 92% triazofos purity.

Available forms

Triazofos is available in several forms; as an emulsifiable concentrate (40%), wettable concentrates,

wettable powder A wettable powder (WP) is an insecticide or other pesticide formulation consisting of the active ingredient An active ingredient is any ingredient that provides biologically active or other direct effect in the diagnosis, cure, mitigation, trea ...

s (30%), ultralow-volume liquids (25%, 40%) and granules (5%) at various concentrations.

Chemical properties

Structure and reactivity

Triazofos 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 ...

pesticide Pesticides are substances that are used to control pests. They include herbicides, insecticides, nematicides, fungicides, and many others (see table). The most common of these are herbicides, which account for approximately 50% of all p ...

used in

acaricides Acaricides are pesticides that kill members of the arachnid subclass ''Acari'', which includes ticks and mites. Acaricides are used both in medicine and agriculture, although the desired selective toxicity differs between the two fields. Termino ...

insecticides 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, in ...

and

nematicides A nematicide is a type of chemical pesticide used to kill plant-parasitic nematodes. Nematicides have tended to be broad-spectrum toxicants possessing high volatility or other properties promoting migration through the soil. Aldicarb (Temik), a c ...

.Cameo Chemicals. (Undated). Triazofos. Retrieved on March 17th 2017 from website: https://cameochemicals.noaa.gov/chemical/5222 Its chemical formula is : C₁₂H₁₆N₃O₃PS containing a

molar mass In chemistry, the molar mass () (sometimes called molecular weight or formula weight, but see related quantities for usage) of a chemical substance ( element or compound) is defined as the ratio between the mass () and the amount of substance ...

of 313,31 g/mol. The chemical compound is susceptible to highly toxic and flammable

phosphine gas Phosphine (IUPAC name: phosphane) is a colorless, flammable, highly toxic compound with the chemical formula , classed as a pnictogen hydride. Pure phosphine is odorless, but technical grade samples have a highly unpleasant odor like rotting f ...

formation in the presence of strong

reducing agent In chemistry, a reducing agent (also known as a reductant, reducer, or electron donor) is a chemical species that "donates" an electron to an (called the , , , or ). Examples of substances that are common reducing agents include hydrogen, carbon ...

s (such as

hydrides In chemistry, a hydride is formally the anion of hydrogen (H−), a hydrogen ion with two electrons. In modern usage, this is typically only used for ionic bonds, but it is sometimes (and has been more frequently in the past) applied to all co ...

). It belongs to the reactive groups of:

amines In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...

phosphines Organophosphines are organophosphorus compounds with the formula PR''n''H3−''n'', where R is an organic substituent. These compounds can be classified according to the value of ''n'': primary phosphines (''n'' = 1), secondary phosphine ...

and

pyridines Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom . It is a highly flammable, weakly alkaline, water-miscible liquid with a ...

. Azo,

diazo In organic chemistry, the diazo group is an organic moiety consisting of two linked nitrogen atoms at the terminal position. Overall charge-neutral organic compounds containing the diazo group bound to a carbon atom are called diazo compounds ...

azido In chemistry, azide (, ) is a linear, polyatomic anion with the formula and structure . It is the conjugate base of hydrazoic acid . Organic azides are organic compounds with the formula , containing the azide functional group. The dominant a ...

hydrazine Hydrazine is an inorganic compound with the chemical formula . It is a simple pnictogen hydride, and is a colourless flammable liquid with an ammonia-like odour. Hydrazine is highly hazardous unless handled in solution as, for example, hydraz ...

and

organic azide Organic may refer to: * Organic, of or relating to an organism, a living entity * Organic, of or relating to an anatomical organ (anatomy), organ Chemistry * Organic matter, matter that has come from a once-living organism, is capable of decay or ...

compounds.

esters In chemistry, an ester is a chemical compound, compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds c ...

sulfate The sulfate or sulphate ion is a polyatomic anion with the empirical formula . Salts, acid derivatives, and peroxides of sulfate are widely used in industry. Sulfates occur widely in everyday life. Sulfates are salts of sulfuric acid and many ...

esters,

phosphate Phosphates are the naturally occurring form of the element phosphorus. In chemistry, a phosphate is an anion, salt, functional group or ester derived from a phosphoric acid. It most commonly means orthophosphate, a derivative of orthop ...

thiophosphate Thiophosphates (or phosphorothioates, PS) are chemical compounds and anions with the general chemical formula (''x'' = 0, 1, 2, or 3) and related derivatives where organic groups are attached to one or more O or S. Thiophosphates feature tetrahedr ...

and

borate A borate is any of a range of boron oxyanions, anions containing boron and oxygen, such as orthoborate , metaborate , or tetraborate ; or any salt of such anions, such as sodium metaborate, and borax . The name also refers to esters of su ...

. Liquids with these reactive groups have been known to react with mineral-based and clay-based absorbents. Furthermore, partial

oxidation Redox ( , , reduction–oxidation or oxidation–reduction) is a type of chemical reaction in which the oxidation states of the reactants change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is ...

of the organophosphate can result in the toxic

phosphorus Phosphorus is a chemical element; it has Chemical symbol, symbol P and atomic number 15. All elemental forms of phosphorus are highly Reactivity (chemistry), reactive and are therefore never found in nature. They can nevertheless be prepared ar ...

oxide An oxide () is a chemical compound containing at least one oxygen atom and one other element in its chemical formula. "Oxide" itself is the dianion (anion bearing a net charge of −2) of oxygen, an O2− ion with oxygen in the oxidation st ...

s release.

Metabolism and mechanisms of action

Metabolism

The metabolic fate of triazofos has been studied in rats and dogs. 23 female Wistar (WISKf (SPF 71)) rats were given triazofos labelled at the 3 position ( radiochemical purity, 98%) as a single oral dose of about 5 mg/kg bw in

sesame oil Sesame oil is an edible vegetable oil derived from sesame seeds. The oil is one of the earliest-known crop-based oils. Worldwide mass modern production is limited due to the inefficient manual harvesting process required to extract the oil. ...

by gastric intubation.InChem. (Undated). Triazophos. Retrieved on March 17th from website: http://www.inchem.org/documents/jmpr/jmpmono/v86pr18.htm Twenty of the rats were used to examine

excretion Excretion is elimination of metabolic waste, which is an essential process in all organisms. In vertebrates, this is primarily carried out by the lungs, Kidney (vertebrates), kidneys, and skin. This is in contrast with secretion, where the substa ...

and

metabolism Metabolism (, from ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cellular processes; the co ...

and the other three for blood assays. The maximum blood drug concentration (

Cmax is the maximum (or peak) serum concentration that a drug achieves in a specified compartment or test area of the body after the drug has been administered and before the administration of a second dose. It is a standard measurement in pharma ...

) was achieved after about 4 hours. The average

half-life Half-life is a mathematical and scientific description of exponential or gradual decay. Half-life, half life or halflife may also refer to: Film * Half-Life (film), ''Half-Life'' (film), a 2008 independent film by Jennifer Phang * ''Half Life: ...

(t1⁄2) of

radioactivity Radioactive decay (also known as nuclear decay, radioactivity, radioactive disintegration, or nuclear disintegration) is the process by which an unstable atomic nucleus loses energy by radiation. A material containing unstable nuclei is conside ...

in the blood was 3.8 hours. After 96 hours, the recovery rate was 98%, indicating that ''

'' was nearly complete. Over 90% of the administered

was

excreted Excretion is elimination of metabolic waste, which is an essential process in all organisms. In vertebrates, this is primarily carried out by the lungs, kidneys, and skin. This is in contrast with secretion, where the substance may have specific ...

via the

urine Urine is a liquid by-product of metabolism in humans and many other animals. In placental mammals, urine flows from the Kidney (vertebrates), kidneys through the ureters to the urinary bladder and exits the urethra through the penile meatus (mal ...

within 48 hours. 4.5% of the excretion was accounted for by faecal elimination after 48 hours. From all the tissues that were analysed, the highest concentration of

was found in the

kidney In humans, the kidneys are two reddish-brown bean-shaped blood-filtering organ (anatomy), organs that are a multilobar, multipapillary form of mammalian kidneys, usually without signs of external lobulation. They are located on the left and rig ...

and the

liver The liver is a major metabolic organ (anatomy), organ exclusively found in vertebrates, which performs many essential biological Function (biology), functions such as detoxification of the organism, and the Protein biosynthesis, synthesis of var ...

, at a relatively low concentration of <0.004 ppm. the urine showed three identifiable metabolites: 1-phenyl-3-hydroxy-(1H)-1,2,4-triazole (43% of the administered dose) and its glucuronide (36%) and sulfate conjugates (13%). The glucuronide was converted back to the parent compound at room temperature, due to it being unstable. Unchanged triazofos was not detected in the

, and quantities of

in the

faeces Feces (also known as faeces American and British English spelling differences#ae and oe, or fæces; : faex) are the solid or semi-solid remains of food that was not digested in the small intestine, and has been broken down by bacteria in the ...

were too low for defining of the chemical species. The metabolic fate of triazofos was also examined in two female

beagle The Beagle is a small breed of scent hound, similar in appearance to the much larger foxhound. The beagle was developed primarily for hunting rabbit or hare, known as beagling. Possessing a great sense of smell and superior tracking inst ...

dogs, with the same treatment and sampling regimen as for

rats Rats are various medium-sized, long-tailed rodents. Species of rats are found throughout the order Rodentia, but stereotypical rats are found in the genus ''Rattus''. Other rat genera include ''Neotoma'' (pack rats), '' Bandicota'' (bandicoot ...

. 14C triazofos at a dose of 4.4–4.8 mg/kg bodyweight was administered in

by gastric intubation. Of the administered dose, an average of 85% after 24 hours and 92% after 48 hours was

via the

. Only 0.3% after 24 hours and 7.2% after 48 hours was accounted for by faecal elimination. Maximum blood drug concentration was achieved after 2 hours. After 48 hours, there was no detectable

in the blood, and the average half-life was 3.6 hours. Altogether, the metabolic fate of triazofos in

dog The dog (''Canis familiaris'' or ''Canis lupus familiaris'') is a domesticated descendant of the gray wolf. Also called the domestic dog, it was selectively bred from a population of wolves during the Late Pleistocene by hunter-gatherers. ...

s was similar to that in

rat Rats are various medium-sized, long-tailed rodents. Species of rats are found throughout the order Rodentia, but stereotypical rats are found in the genus ''Rattus''. Other rat genera include '' Neotoma'' (pack rats), '' Bandicota'' (bandicoo ...

s . The

consisted of the same three

metabolite In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...

s as in

s. However, there was one other

found only in the dog's

representing 11% of the administered dose. It was considered to be another

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

conjugate of the 1-phenyl-3-hydroxy-(1H)-1,2,4-triazole

. There was no unchanged triazofos found in the

of the

s. The

contained low concentrations of triazofos and the free 1-phenyl-3-hydroxy-(1H)-1,2,4-triazole

as well as five unidentified

s at about 0.7, 0.3 and 7.3% of the administered dose, respectively.

Effects on animals

The signal of oral

poisoning Poisoning is the harmful effect which occurs when Toxicity, toxic substances are introduced into the body. The term "poisoning" is a derivative of poison, a term describing any chemical substance that may harm or kill a living organism upon ...

similarly happen in

mice A mouse (: mice) is a small rodent. Characteristically, mice are known to have a pointed snout, small rounded ears, a body-length scaly tail, and a high breeding rate. The best known mouse species is the common house mouse (''Mus musculus' ...

s and

s, characterized by tremors,

abdominal The abdomen (colloquially called the gut, belly, tummy, midriff, tucky, or stomach) is the front part of the torso between the thorax (chest) and pelvis in humans and in other vertebrates. The area occupied by the abdomen is called the abdominal ...

position,

squatting Squatting is the action of occupying an abandoned or unoccupied area of land or a building (usually residential) that the squatter does not own, rent or otherwise have lawful permission to use. The United Nations estimated in 2003 that there wer ...

, jerky respiration,

lachrymation Tears are a clear liquid secreted by the lacrimal glands (tear gland) found in the eyes of all land mammals. Tears are made up of water, electrolytes, proteins, lipids, and mucins that form layers on the surface of eyes. The different types of ...

saliva Saliva (commonly referred as spit or drool) is an extracellular fluid produced and secreted by salivary glands in the mouth. In humans, saliva is around 99% water, plus electrolytes, mucus, white blood cells, epithelial cells (from which ...

tion, saltatory spasm, tonic

convulsion A convulsion is a medical condition where the body muscles contract and relax rapidly and repeatedly, resulting in uncontrolled shaking. Because epileptic seizures typically include convulsions, the term ''convulsion'' is often used as a synony ...

s.Inchem. (1982). Pesticide Residues in food – 1982. Retrieved on March 17th 2017, from website: http://www.inchem.org/documents/jmpr/jmpmono/v82pr33.htmHamernik, K.L. (Undated). Pesticide residues in food – 2002- Joint FAO/WHO meeting on pesticide residues: Triazophos. Retrieved on March 17th 2017, from website: http://www.inchem.org/documents/jmpr/jmpmono/2002pr14.htm *

Acute Toxicity Acute toxicity describes the adverse effects of a substance that result either from a single exposure or from multiple exposures in a short period of time (usually less than 24 hours). To be described as ''acute'' toxicity, the adverse effect ...

: In

s and guinea-pigs, the acute

LD50 In toxicology, the median lethal dose, LD50 (abbreviation for "lethal dose, 50%"), LC50 (lethal concentration, 50%) or LCt50 is a toxic unit that measures the lethal dose of a given substance. The value of LD50 for a substance is the dose requ ...

value of triazofos ranged from 26–82 mg/kg body weight, while

s have higher values up to 500 mg/kg body weight. Deaths occurred within minutes to several days after oral administration. Resulting in

WHO The World Health Organization (WHO) is a specialized agency of the United Nations which coordinates responses to international public health issues and emergencies. It is headquartered in Geneva, Switzerland, and has 6 regional offices and 15 ...

's consideration of triazofos as a highly hazardous compound. *

Genotoxicity Genotoxicity is the chemical property, property of chemical agents that damage the genetic information within a cell causing mutations, which may lead to cancer. While genotoxicity is often confused with mutagenicity, all mutagens are genotoxic, bu ...

: In the study of

toxicity Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacteria, bacterium, or plant, as well as the effect o ...

and

carcinogen A carcinogen () is any agent that promotes the development of cancer. Carcinogens can include synthetic chemicals, naturally occurring substances, physical agents such as ionizing and non-ionizing radiation, and biologic agents such as viruse ...

icity effects in mice and rats, triazofos induced no significant or consistent increase in any tumour types. *

Reproductive toxicity Reproductive toxicity refers to the potential risk from a given chemical, physical or biologic agent to adversely affect both male and female fertility as well as teratogen, offspring development. Reproductive toxicants may adversely affect sexu ...

: Signs of

such as aggressive behaviour and decreased body weight and food consumption were seen only in F1 parent. Hence, there is no significant effect observed for the

reproductive toxicity Reproductive toxicity refers to the potential risk from a given chemical, physical or biologic agent to adversely affect both male and female fertility as well as teratogen, offspring development. Reproductive toxicants may adversely affect sexu ...

Mechanism of action

Triazofos interacts with several enzymes and signalling pathways according to various bio-assay results:PubChem Compound Database. (Undated). Triazophos: Biological Test Results (Bioassay results). Retrieved on March 17th 2017, from website:https://pubchem.ncbi.nlm.nih.gov/compound/Triazophos#section=BioAssay-Results * inhibits

vitamin D Vitamin D is a group of structurally related, fat-soluble compounds responsible for increasing intestinal absorption of calcium, magnesium, and phosphate, along with numerous other biological functions. In humans, the most important compo ...

receptor (VDR). * acts as a small molecule disruptors of the mitochondrial

membrane potential Membrane potential (also transmembrane potential or membrane voltage) is the difference in electric potential between the interior and the exterior of a biological cell. It equals the interior potential minus the exterior potential. This is th ...

. * acts as a disruptor of small molecule activators of the human pregnane X receptor (

PXR In the field of molecular biology, the pregnane X receptor (PXR), also known as the steroid and xenobiotic sensing nuclear receptor (SXR) or nuclear receptor subfamily 1, group I, member 2 (NR1I2) is a protein that in humans is encoded by the ' ...

) signalling pathway. * acts as a

genotoxic Genotoxicity is the property of chemical agents that damage the genetic information within a cell causing mutations, which may lead to cancer. While genotoxicity is often confused with mutagenicity, all mutagens are genotoxic, but some genotoxic s ...

compound against isogenic chicken DT40 cell lines. * acts as a small molecule

antagonist An antagonist is a character in a story who is presented as the main enemy or rival of the protagonist and is often depicted as a villain.oestrogen Estrogen (also spelled oestrogen in British English; see spelling differences) is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three m ...

receptor alpha ( Er-alpha) signalling pathway. * acts as a small molecule that activates the Aryl (AHR) hydrocarbon receptor signalling pathway. * acts as a small molecule antagonist of the constitutive androstane receptor (CAR) signalling pathway.

Efficacy and toxicity

Efficacy

The use of triazofos as an

in many Asian countries such

China China, officially the People's Republic of China (PRC), is a country in East Asia. With population of China, a population exceeding 1.4 billion, it is the list of countries by population (United Nations), second-most populous country after ...

India India, officially the Republic of India, is a country in South Asia. It is the List of countries and dependencies by area, seventh-largest country by area; the List of countries by population (United Nations), most populous country since ...

and

Indonesia Indonesia, officially the Republic of Indonesia, is a country in Southeast Asia and Oceania, between the Indian Ocean, Indian and Pacific Ocean, Pacific oceans. Comprising over List of islands of Indonesia, 17,000 islands, including Sumatra, ...

is widely known due to many insects and pests playing important roles in the market production of staple plant food production.Lal, R. Jat, B.J. "Bio-efficacy of insecticides and biorationals against the incidence of whitefly, Bemisia tabaci (Genn.) and yellow mosaic virus in mungbean. Departments of Entomology, CCS Haryana Agricultural University, India. African Journal of Agricultural Research. Vol. !0 (10) pp. 1050-1056. Among various constraints,

leafhopper Leafhopper is the common name for any species from the family (biology), family Cicadellidae: based on the type genus ''Cicadella''. These minute insects, colloquially known as hoppers, are plant feeders that suck plant sap from grass, shrubs, or ...

s (Amarasca devastans) 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 ...

(

Bemisia ''Bemisia'' is a genus of whitefly in the family Aleyrodidae. Species *'' Bemisia afer'' Priesner & Hosny, 1934 *'' Bemisia alni'' Takahashi, 1957 *'' Bemisia antennata'' Gameel, 1968 *'' Bemisia bambusae'' Takahashi, 1942 *'' Bemisia berberic ...

tabaci) are one of the major factors in cultivation problems due to their capability to suck the cell sap of plants. An experiment was conducted by

Horticultural Horticulture (from ) is the art and science of growing fruits, vegetables, flowers, trees, shrubs and ornamental plants. Horticulture is commonly associated with the more professional and technical aspects of plant cultivation on a smaller and mo ...

Ecosystem in India about the efficacy of triazofos as an

for

s and

on Brinjal (Solamum melongena L), one of the prominent crops in

.Kumar, P. (2010). "Efficacy of Triazophos 40 EC against pest complex of brinjal". Kittur Rani Channamma College of Horticulture, Karnataka, India. Pest Management in Horticultural Ecosystems. Vol. 16 (1). Pp 87-89. The investigation was arranged with various market names of triazofos with varying concentrations. The analysis was established after 20 days of transplanting and observing the pest incidence. Before spraying the

, there were no observations of significant numbers between

s and

with the respect to leaf samples. The visual observations were also constructed in assessing

phytotoxic Phytotoxins are substances that are poisonous or toxic to the growth of plants. Phytotoxic substances may result from human activity, as with herbicides, or they may be produced by plants, by microorganisms, or by naturally occurring chemical react ...

symptoms such as injury on leaf tips or surface,

wilting Wilting is the loss of rigidity of non-woody parts of plants. This occurs when the turgor pressure in non- lignified plant cells falls towards zero, as a result of diminished water in the cells. Wilting also serves to reduce water loss, as it ...

, etc. Nonetheless, no

symptoms were observed on the plants with the treatment. In conclusion, the triazofos of 1250 ml/ ha was most effective against

and shoot and fruit borer of

brinjal Eggplant ( US, CA, AU, PH), aubergine ( UK, IE, NZ), brinjal ( IN, SG, MY, ZA, SLE), or baigan ( IN, GY) is a plant species in the nightshade family Solanaceae. ''Solanum melongena'' is grown worldwide for its edible fruit, typic ...

Toxicity

Triazofos (O,O-diethyl O-1-phenyl-1H-1,2,4-triazol-3-yl phosphorothioate) is considered an

organophosphorus Organophosphorus chemistry is the scientific study of the synthesis and properties of organophosphorus compounds, which are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarb ...

toxicologically by JMPR in 1982, 1986 and 1991. With an ADI of 0–0.001 mg/kg bodyweight. This establishment was made regarding the view of triazofos in causing delayed

neurotoxicity Neurotoxicity is a form of toxicity in which a biological, chemical, or physical agent produces an adverse effect on the structure or function of the central and/or peripheral nervous system. It occurs when exposure to a substance – specifical ...

Toxicological Toxicology is a scientific discipline (academia), discipline, overlapping with biology, chemistry, pharmacology, and medicine, that involves the study of the adverse effects of chemical substances on living organisms and the practice of diagnos ...

evaluation revealed the maximum level of triazofos which causes no

toxicological Toxicology is a scientific discipline (academia), discipline, overlapping with biology, chemistry, pharmacology, and medicine, that involves the study of the adverse effects of chemical substances on living organisms and the practice of diagnos ...

effect and the maximum level of exposure considered acceptable for

human Humans (''Homo sapiens'') or modern humans are the most common and widespread species of primate, and the last surviving species of the genus ''Homo''. They are Hominidae, great apes characterized by their Prehistory of nakedness and clothing ...

s. The estimated acceptable daily intake for

s is 0–0.001 mg/kg bodyweight.(See Table 2 and 3)

Adverse effects and health hazards in humans

Acute exposure to triazofos may produce the following signs and symptoms:

sweating Perspiration, also known as sweat, is the fluid secreted by sweat glands in the skin of mammals. Two types of sweat glands can be found in humans: eccrine glands and apocrine glands. The eccrine sweat glands are distributed over much of the ...

blurred vision Blurred vision is an ocular symptom where vision becomes less precise and there is added difficulty to resolve fine details. Temporary blurred vision may involve dry eyes, eye infections, alcohol poisoning, hypoglycemia, or low blood pressur ...

headache A headache, also known as cephalalgia, is the symptom of pain in the face, head, or neck. It can occur as a migraine, tension-type headache, or cluster headache. There is an increased risk of Depression (mood), depression in those with severe ...

dizziness Dizziness is an imprecise term that can refer to a sense of disorientation in space, vertigo, or lightheadedness. It can also refer to Balance disorder, disequilibrium or a non-specific feeling, such as giddiness or foolishness. Dizziness is a ...

, profound weakness,

muscle spasms A spasm is a sudden involuntary contraction of a muscle, a group of muscles, or a hollow organ, such as the bladder. A spasmodic muscle contraction may be caused by many medical conditions, including dystonia. Most commonly, it is a musc ...

seizures A seizure is a sudden, brief disruption of brain activity caused by abnormal, excessive, or synchronous neuronal firing. Depending on the regions of the brain involved, seizures can lead to changes in movement, sensation, behavior, awareness, o ...

coma A coma is a deep state of prolonged unconsciousness in which a person cannot be awakened, fails to Nociception, respond normally to Pain, painful stimuli, light, or sound, lacks a normal Circadian rhythm, sleep-wake cycle and does not initiate ...

mental confusion In psychology, confusion is the quality or emotional state of being bewildered or unclear. The term "acute mental confusion"

and

psychosis In psychopathology, psychosis is a condition in which a person is unable to distinguish, in their experience of life, between what is and is not real. Examples of psychotic symptoms are delusions, hallucinations, and disorganized or inco ...

, excessive

tion,

nausea Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. It can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the throat. Over 30 d ...

vomiting Vomiting (also known as emesis, puking and throwing up) is the forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose. Vomiting can be the result of ailments like food poisoning, gastroenteritis, pre ...

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 ...

, and

diarrhea Diarrhea (American English), also spelled diarrhoea or diarrhœa (British English), is the condition of having at least three loose, liquid, or watery bowel movements in a day. It often lasts for a few days and can result in dehydration d ...

. Respiratory signs include

dyspnoea Shortness of breath (SOB), known as dyspnea (in AmE) or dyspnoea (in BrE), is an uncomfortable feeling of not being able to breathe well enough. The American Thoracic Society defines it as "a subjective experience of breathing discomfort that c ...

pulmonary oedema Pulmonary edema (British English: oedema), also known as pulmonary congestion, is excessive fluid accumulation in the tissue or air spaces (usually alveoli) of the lungs. This leads to impaired gas exchange, most often leading to shortness ...

respiratory depression Hypoventilation (also known as respiratory depression) occurs when ventilation is inadequate (''hypo'' meaning "below") to perform needed respiratory gas exchange. By definition it causes an increased concentration of carbon dioxide (hypercapni ...

and

respiratory paralysis Respiratory failure results from inadequate gas exchange by the respiratory system, meaning that the arterial oxygen, carbon dioxide, or both cannot be kept at normal levels. A drop in the oxygen carried in the blood is known as hypoxemia; a ris ...

. Chest pains are also reported. The

contains material with

cholinesterase The enzyme cholinesterase (EC 3.1.1.8, choline esterase; systematic name acylcholine acylhydrolase) catalyses the hydrolysis of choline-based esters: : an acylcholine + H2O = choline + a carboxylate Several of these serve as neurotransmitte ...

inhibitor which corresponds to the acts on the

central nervous system The central nervous system (CNS) is the part of the nervous system consisting primarily of the brain, spinal cord and retina. The CNS is so named because the brain integrates the received information and coordinates and influences the activity o ...

. Organic phosphorus

s can be absorbed by the

skin Skin is the layer of usually soft, flexible outer tissue covering the body of a vertebrate animal, with three main functions: protection, regulation, and sensation. Other animal coverings, such as the arthropod exoskeleton, have different ...

respiratory The respiratory system (also respiratory apparatus, ventilatory system) is a biological system consisting of specific organs and structures used for gas exchange in animals and plants. The anatomy and physiology that make this happen varies gr ...

and

gastrointestinal The gastrointestinal tract (GI tract, digestive tract, alimentary canal) is the tract or passageway of the digestive system that leads from the mouth to the anus. The tract is the largest of the body's systems, after the cardiovascular system. ...

tracts.

Antidote

The following

antidote An antidote is a substance that can counteract a form of poisoning. The term ultimately derives from the Greek term φάρμακον ἀντίδοτον ''(pharmakon antidoton)'', "(medicine) given as a remedy". An older term in English which is ...

s can relieve poisoning obtained from triazofos.

Pralidoxime Pralidoxime (2-pyridine aldoxime methyl chloride) or 2-PAM, usually as the chloride or iodide salts, belongs to a family of compounds called oximes that bind to organophosphate-inactivated acetylcholinesterase. It is used to treat organophosph ...

, a treatment of choice

pralidoxime Pralidoxime (2-pyridine aldoxime methyl chloride) or 2-PAM, usually as the chloride or iodide salts, belongs to a family of compounds called oximes that bind to organophosphate-inactivated acetylcholinesterase. It is used to treat organophosph ...

(Protopam, 2-PAM) can be used as a

reactivator in cases of severe

. Less than 48 hours after

relieves the

nicotinic Nicotinic acetylcholine receptors, or nAChRs, are receptor polypeptides that respond to the neurotransmitter acetylcholine. Nicotinic receptors also respond to drugs such as the agonist nicotine. They are found in the central and peripheral ner ...

and

muscarinic A muscarinic acetylcholine receptor agonist, also simply known as a muscarinic agonist or as a muscarinic agent, is an agent that activates the activity of the muscarinic acetylcholine receptor. The muscarinic receptor has different subtypes, lab ...

effects. It works by reactivating the

and also by slowing the ageing process of

phosphorylated In biochemistry, phosphorylation is described as the "transfer of a phosphate group" from a donor to an acceptor. A common phosphorylating agent (phosphate donor) is ATP and a common family of acceptor are alcohols: : This equation can be writt ...

to its non-reactivable form. Another

Atropine Atropine is a tropane alkaloid and anticholinergic medication used to treat certain types of nerve agent and pesticide poisonings as well as some types of slow heart rate, and to decrease saliva production during surgery. It is typically give ...

is effective against

manifestation but not to

actions such as muscle weakness and twitching and

. The use of

atropine Atropine is a tropane alkaloid and anticholinergic medication used to treat certain types of nerve agent and pesticide poisonings as well as some types of slow heart rate, and to decrease saliva production during surgery. It is typically give ...

has been reported to improve

respiratory distress Shortness of breath (SOB), known as dyspnea (in AmE) or dyspnoea (in BrE), is an uncomfortable feeling of not being able to breathe well enough. The American Thoracic Society defines it as "a subjective experience of breathing discomfort that c ...

, decrease bronchial secretions and increase the oxygenation.

References

{{Acetylcholine metabolism and transport modulators Acetylcholinesterase inhibitors Organophosphate insecticides Acaricides Nematicides Ethyl esters Triazoles