Cyanazine is a

herbicide Herbicides (, ), also commonly known as weed killers, are substances used to control undesired plants, also known as weeds.EPA. February 201Pesticides Industry. Sales and Usage 2006 and 2007: Market Estimates. Summary in press releasMain page f ...

that belongs to the group of

triazine Triazines are a class of nitrogen-containing heterocycles. The parent molecules' molecular formula is . They exist in three isomeric forms, 1,3,5-triazines being common. Structure The triazines have planar six-membered benzene-like ring but ...

s. Cyanazine inhibits

photosynthesis Photosynthesis ( ) is a system of biological processes by which photosynthetic organisms, such as most plants, algae, and cyanobacteria, convert light energy, typically from sunlight, into the chemical energy necessary to fuel their metabo ...

and is therefore used as a

History

Cyanazine is used as a herbicide to control annual grasses and broadleaf weeds. It belongs to the group of

herbicides Herbicides (, ), also commonly known as weed killers, are substances used to control undesired plants, also known as weeds.EPA. February 201Pesticides Industry. Sales and Usage 2006 and 2007: Market Estimates. Summary in press releasMain page f ...

, just as

atrazine Atrazine ( ) is a Organochlorine compound, chlorinated herbicide of the triazine class. It is used to prevent pre-emergence broadleaf weeds in crops such as maize (corn), soybean and sugarcane and on turf, such as golf courses and residential law ...

. These

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 ...

s work by inhibiting

. The majority of the cyanazine used is used for

corn Maize (; ''Zea mays''), also known as corn in North American English, is a tall stout Poaceae, grass that produces cereal grain. It was domesticated by indigenous peoples of Mexico, indigenous peoples in southern Mexico about 9,000 years ago ...

. In 1985 this was 96% of the used cyanazine. The Environmental Protection Agency ( EPA) made a profile on the Health and Environmental effects of cyanazine in 1984.U.S. EPA. HEALTH AND ENVIRONMENTAL EFFECTS PROFILE FOR CYANAZINE. U.S. Environmental Protection Agency, Washington, D.C., EPA/600/X-84/243 (NTIS PB88162409), 1984. In 1971 cyanazine was brought on the market under the names 'Bladex' and 'Fortol' by Shell. Cyanazine and the other

s have been among the group of most heavily used

s in the mid-west and the

United States of America The United States of America (USA), also known as the United States (U.S.) or America, is a country primarily located in North America. It is a federal republic of 50 states and a federal capital district, Washington, D.C. The 48 contiguo ...

. In 2002 the European Union pesticides database disapproved the usage of cyanazine as a herbicide. It is classified as a teratogen on the Hazardous Substance List, already in 1986.

Structure and reactivity

Cyanazine is the common name for 2-chloro-4-(1-cyano-1-methylethyl-amino)-6-ethylamine-1,3,5-triazine. The

molecular formula A chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as paren ...

for this compound is ,

molecular weight A molecule is a group of two or more atoms that are held together by Force, attractive forces known as chemical bonds; depending on context, the term may or may not include ions that satisfy this criterion. In quantum physics, organic chemi ...

is 240.695 g/mol. Cyanazine is a white or colourless crystalline solid. The

melting point The melting point (or, rarely, liquefaction point) of a substance is the temperature at which it changes state of matter, state from solid to liquid. At the melting point the solid and liquid phase (matter), phase exist in Thermodynamic equilib ...

is around 166.5-167.0 °C. The logP is 2.22. Cyanazine structure

Cyanazine is not very reactive in neutral and slightly acidic/basic media, it is

hydrolysed Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysis ...

by strong

acid An acid is a molecule or ion capable of either donating a proton (i.e. Hydron, hydrogen cation, H+), known as a Brønsted–Lowry acid–base theory, Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis ...

s and bases. It is stable to

heat In thermodynamics, heat is energy in transfer between a thermodynamic system and its surroundings by such mechanisms as thermal conduction, electromagnetic radiation, and friction, which are microscopic in nature, involving sub-atomic, ato ...

light Light, visible light, or visible radiation is electromagnetic radiation that can be visual perception, perceived by the human eye. Visible light spans the visible spectrum and is usually defined as having wavelengths in the range of 400– ...

and to

hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...

. It is also stable to UV irradiation under practical conditions. Cyanazine can

decompose Decomposition is the process by which dead organic substances are broken down into simpler organic or inorganic matter such as carbon dioxide, water, simple sugars and mineral salts. The process is a part of the nutrient cycle and is essen ...

on heating. This produces

corrosive Corrosion is a natural process that converts a refined metal into a more chemically stable oxide. It is the gradual deterioration of materials (usually a metal) by chemical or electrochemical reaction with their environment. Corrosion engine ...

fumes of

hydrogen chloride The Chemical compound, compound hydrogen chloride has the chemical formula and as such is a hydrogen halide. At room temperature, it is a colorless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric water vapor. Hyd ...

nitrogen oxide Nitrogen oxide may refer to a binary compound of oxygen and nitrogen, or a mixture of such compounds: Charge-neutral *Nitric oxide (NO), nitrogen(II) oxide, or nitrogen monoxide * Nitrogen dioxide (), nitrogen(IV) oxide * Nitrogen trioxide (), o ...

s and

cyanide In chemistry, cyanide () is an inorganic chemical compound that contains a functional group. This group, known as the cyano group, consists of a carbon atom triple-bonded to a nitrogen atom. Ionic cyanides contain the cyanide anion . This a ...

s. Cyanazine has one of the lowest rate constant of reactivity with

ozone Ozone () (or trioxygen) is an Inorganic compound, inorganic molecule with the chemical formula . It is a pale blue gas with a distinctively pungent smell. It is an allotrope of oxygen that is much less stable than the diatomic allotrope , break ...

from different

s. Among four different

groups, cyanazine degrades the fastest in soil.

Synthesis

Cyanazine is a chloro-1,3,5-triazine that is substituted at positions 6 and 4 by an ethyl amino and an

amino group 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 ...

respectively. It can be prepared by reacting

cyanuric chloride Cyanuric chloride is an organic compound with the formula (NCCl)3. This white solid is the chlorinated derivative of 1,3,5-triazine. It is the trimer of cyanogen chloride. Cyanuric chloride is the main precursor to the popular but controversi ...

with

ethylamine Ethylamine, also known as ethanamine, is an organic compound with the chemical formula, formula CH3CH2NH2. This colourless gas has a strong ammonia-like odor. It condenses just below room temperature to a liquid miscibility, miscible with virtual ...

and 2-amino-2-methylpropionitrile.

Available forms

Cyanazine is available as a soluble concentrate, flowable concentrate, emulsifiable concentrate, wettable powder and granular product

Mechanisms of action

Cyanazine inhibits

and is therefore used as a

. It destroys unwanted

vegetation Vegetation is an assemblage of plants and the ground cover they provide. It is a general term, without specific reference to particular Taxon, taxa, life forms, structure, Spatial ecology, spatial extent, or any other specific Botany, botanic ...

, especially various types of weeds,

grasses Poaceae ( ), also called Gramineae ( ), is a large and nearly ubiquitous family of monocotyledonous flowering plants commonly known as grasses. It includes the cereal grasses, bamboos, the grasses of natural grassland and species cultivated in ...

and

woody plant A woody plant is a plant that produces wood as its structural tissue and thus has a hard stem. In cold climates, woody plants further survive winter or dry season above ground, as opposed to Herbaceous plant, herbaceous plants that die back to t ...

s. The primary site of inhibition was on the reducing side of

photosystem II Photosystem II (or water-plastoquinone oxidoreductase) is the first protein complex in the light-dependent reactions of oxygenic photosynthesis. It is located in the thylakoid membrane of plants, algae, and cyanobacteria. Within the photosystem ...

. They inhibit the

electron The electron (, or in nuclear reactions) is a subatomic particle with a negative one elementary charge, elementary electric charge. It is a fundamental particle that comprises the ordinary matter that makes up the universe, along with up qua ...

transfer step between the primary electron acceptor (Q) and the

plastoquinone Plastoquinone (PQ) is a terpenoid-quinone ( meroterpenoid) molecule involved in the electron transport chain in the light-dependent reactions of photosynthesis. The most common form of plastoquinone, known as PQ-A or PQ-9, is a 2,3-dimethyl-1,4- ...

pool of the

electron transport chain An electron transport chain (ETC) is a series of protein complexes and other molecules which transfer electrons from electron donors to electron acceptors via redox reactions (both reduction and oxidation occurring simultaneously) and couples th ...

Metabolism

The

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 ...

pathways of cyanazine have been describe for different

animal Animals are multicellular, eukaryotic organisms in the Biology, biological Kingdom (biology), kingdom Animalia (). With few exceptions, animals heterotroph, consume organic material, Cellular respiration#Aerobic respiration, breathe oxygen, ...

and

plant species Flora (: floras or florae) is all the plant life present in a particular region or time, generally the naturally occurring ( indigenous) native plants. The corresponding term for animals is ''fauna'', and for fungi, it is '' funga''. Sometimes ...

. Different studies showed that in

animal models A model organism is a non-human species that is extensively studied to understand particular biological phenomena, with the expectation that discoveries made in the model organism will provide insight into the workings of other organisms. Mod ...

(

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 ...

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 &

cows Cattle (''Bos taurus'') are large, domesticated, bovid ungulates widely kept as livestock. They are prominent modern members of the subfamily Bovinae and the most widespread species of the genus '' Bos''. Mature female cattle are called co ...

) the cyanazine is quickly absorbed in the

intestines 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. ...

. For the degradation of the absorbed cyanazine the following metabolic pathways are involved: de-

alkylation Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting al ...

& conjugation with

glutathione Glutathione (GSH, ) is an organic compound with the chemical formula . It is an antioxidant in plants, animals, fungi, and some bacteria and archaea. Glutathione is capable of preventing damage to important cellular components caused by sources ...

, which results in different

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. After undergoing these metabolic pathways the metabolites leave the body in 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 ...

and

feces 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 ...

. For example, in

s there were found seven

s in

and

after oral intake of cyanazine. Another major route of degradation for cyanazine in

mammal A mammal () is a vertebrate animal of the Class (biology), class Mammalia (). Mammals are characterised by the presence of milk-producing mammary glands for feeding their young, a broad neocortex region of the brain, fur or hair, and three ...

s is N-De- ethylation, which leads to the yield of an

ethyl group In organic chemistry, an ethyl group (abbr. Et) is an alkyl substituent with the formula , derived from ethane (). ''Ethyl'' is used in the International Union of Pure and Applied Chemistry The International Union of Pure and Applied ...

. The free

will then by excreted by breathing. In plants the following metabolic pathways are involved

, N-de-

and conjugation with

, resulting in different

s (shown in the figure below). Degradation Pathway of Cyanazine

Indications

Cyanazine is used as a

to control annual

and broadleaf weeds in

grain A grain is a small, hard, dry fruit (caryopsis) – with or without an attached husk, hull layer – harvested for human or animal consumption. A grain crop is a grain-producing plant. The two main types of commercial grain crops are cereals and ...

sorghum ''Sorghum bicolor'', commonly called sorghum () and also known as great millet, broomcorn, guinea corn, durra, imphee, jowar, or milo, is a species in the Poaceae, grass genus ''Sorghum (genus), Sorghum'' cultivated for its grain. The grain i ...

cotton Cotton (), first recorded in ancient India, is a soft, fluffy staple fiber that grows in a boll, or protective case, around the seeds of the cotton plants of the genus '' Gossypium'' in the mallow family Malvaceae. The fiber is almost pure ...

and

wheat Wheat is a group of wild and crop domestication, domesticated Poaceae, grasses of the genus ''Triticum'' (). They are Agriculture, cultivated for their cereal grains, which are staple foods around the world. Well-known Taxonomy of wheat, whe ...

fallow.

Efficacy

Cyanazine is used in the following doses: for preventing weeds, a dose of 0,14 kg/km2 – 0,54 kg/km2 is used. To treat existing weeds, 0.136 kg/km2 – 0,23 kg/km2 is used. In

s and

algae Algae ( , ; : alga ) is an informal term for any organisms of a large and diverse group of photosynthesis, photosynthetic organisms that are not plants, and includes species from multiple distinct clades. Such organisms range from unicellular ...

, the

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 ...

LC50 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 requir ...

EC50 ] Half maximal effective concentration (EC50) is a measure of the concentration of a drug, antibody or toxicant which induces a stimulus–response model, biological response halfway between the baseline and maximum after a specified exposure tim ...

are as following: After repeated doses of 25 ppm cyanazine mixed in

diets, no toxic effects were seen.

Adverse effects

Cyanazine was found to pollute surface waters and drinking waters in multiple

countries A country is a distinct part of the Earth, world, such as a state (polity), state, nation, or other polity, political entity. When referring to a specific polity, the term "country" may refer to a sovereign state, List of states with limited r ...

North America North America is a continent in the Northern Hemisphere, Northern and Western Hemisphere, Western hemispheres. North America is bordered to the north by the Arctic Ocean, to the east by the Atlantic Ocean, to the southeast by South Ameri ...

and in

groundwater Groundwater is the water present beneath Earth's surface in rock and Pore space in soil, soil pore spaces and in the fractures of stratum, rock formations. About 30 percent of all readily available fresh water in the world is groundwater. A unit ...

s in the

Netherlands , Terminology of the Low Countries, informally Holland, is a country in Northwestern Europe, with Caribbean Netherlands, overseas territories in the Caribbean. It is the largest of the four constituent countries of the Kingdom of the Nether ...

. However, cyanazine or cyanazine degradation products have not been detected in

food Food is any substance consumed by an organism for Nutrient, nutritional support. Food is usually of plant, animal, or Fungus, fungal origin and contains essential nutrients such as carbohydrates, fats, protein (nutrient), proteins, vitamins, ...

. Based on data from Canada and the Netherlands, intake from

drinking water Drinking water or potable water is water that is safe for ingestion, either when drunk directly in liquid form or consumed indirectly through food preparation. It is often (but not always) supplied through taps, in which case it is also calle ...

is around an estimate 0.2-0.3 μg/day. The

World Health Organization The World Health Organization (WHO) is a list of specialized agencies of the United Nations, specialized agency of the United Nations which coordinates responses to international public health issues and emergencies. It is headquartered in Gen ...

(WHO) set a maximum value of 0.198 μg/kg body weight, due to possible toxic effects to

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. Furthermore, as seen in the table above, aquatic lifeforms are affected at a much lower

concentration In chemistry, concentration is the abundance of a constituent divided by the total volume of a mixture. Several types of mathematical description can be distinguished: '' mass concentration'', '' molar concentration'', '' number concentration'', ...

of cyanazine than

terrestrial animal Terrestrial animals are animals that live predominantly or entirely on land (e.g. cats, chickens, ants, most spiders), as compared with aquatic animals, which live predominantly or entirely in the water (e.g. fish, lobsters, octopuses), ...

s. That, combined with the fact that cyanazine quickly washes out of the

soil Soil, also commonly referred to as earth, is a mixture of organic matter, minerals, gases, water, and organisms that together support the life of plants and soil organisms. Some scientific definitions distinguish dirt from ''soil'' by re ...

to the surrounding waters, makes that the

aquatic ecosystem An aquatic ecosystem is an ecosystem found in and around a body of water, in contrast to land-based terrestrial ecosystems. Aquatic ecosystems contain communities of organisms—aquatic life—that are dependent on each other and on their environ ...

s are most compromised by cyanazine.

Toxicity

Triazine Triazines are a class of nitrogen-containing heterocycles. The parent molecules' molecular formula is . They exist in three isomeric forms, 1,3,5-triazines being common. Structure The triazines have planar six-membered benzene-like ring but ...

s like cyanazine are extremely

toxic 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, bacterium, or plant, as well as the effect on a subst ...

to certain types of

plant Plants are the eukaryotes that form the Kingdom (biology), kingdom Plantae; they are predominantly Photosynthesis, photosynthetic. This means that they obtain their energy from sunlight, using chloroplasts derived from endosymbiosis with c ...

s. This is why they are so effective in killing specific species of broadleaf weeds. Cyanazine will result in the dysfunction of

by binding important proteins which are required for this process. When this important step in

fails, a plant is not able to produce sugars which are crucial for its growth and

Toxicity in humans

* Acute effects Contact with cyanazine may cause

dermatitis Dermatitis is a term used for different types of skin inflammation, typically characterized by itchiness, redness and a rash. In cases of short duration, there may be small blisters, while in long-term cases the skin may become thickened ...

depending on the severity of the contact. Also, when high levels of cyanazine are being ingested,

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 ...

can occur.

Inhalation Inhalation (or inspiration) happens when air or other gases enter the lungs. Inhalation of air Inhalation of air, as part of the cycle of breathing, is a vital process for all human life. The process is autonomic (though there are exceptions ...

of cyanazine fumes may lead to airway irritation. *

Carcinogenesis Carcinogenesis, also called oncogenesis or tumorigenesis, is the formation of a cancer, whereby normal cell (biology), cells are malignant transformation, transformed into cancer cells. The process is characterized by changes at the cellular, G ...

The

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 ...

ic effects of cyanazine were unclear for a long time. However, it is not likely that this

will have any

ic effects on humans. More research is needed to fully confirm that cyanazine is not

ic. This is why the

USEPA 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 ...

rated cyanazine as a group C

chemical A chemical substance is a unique form of matter with constant chemical composition and characteristic properties. Chemical substances may take the form of a single element or chemical compounds. If two or more chemical substances can be combin ...

; this means that it could be

ic.

Toxicity in animals

* Endocrine-related effects Research has shown that

is able to influence the LH and prolactin secretion of female

s. These

hormonal A hormone (from the Greek participle , "setting in motion") is a class of signaling molecules in multicellular organisms that are sent to distant organs or tissues by complex biological processes to regulate physiology and behavior. Hormones a ...

changes appear to be caused by an altered function of the

pituitary The pituitary gland or hypophysis is an endocrine gland in vertebrates. In humans, the pituitary gland is located at the base of the brain, protruding off the bottom of the hypothalamus. The pituitary gland and the hypothalamus control much of th ...

. As cyanazine belongs to the same class of

s as

, the effect on the

status of rats by cyanazine could be the same. Cyanazine may also influence GABAA-receptors in the

brain The brain is an organ (biology), organ that serves as the center of the nervous system in all vertebrate and most invertebrate animals. It consists of nervous tissue and is typically located in the head (cephalization), usually near organs for ...

s, depending on the dosage that is given. This can cause disruptions in

GnRH Gonadotropin-releasing hormone (GnRH) is a releasing hormone responsible for the release of follicle-stimulating hormone (FSH) and luteinizing hormone (LH) from the anterior pituitary. GnRH is a tropic peptide hormone synthesized and released ...

-release. * Teratogenesis Cyanazine may cause

malformations A birth defect is an abnormal condition that is present at birth, regardless of its cause. Birth defects may result in disabilities Disability is the experience of any condition that makes it more difficult for a person to do certain act ...

in the

embryo An embryo ( ) is the initial stage of development for a multicellular organism. In organisms that reproduce sexually, embryonic development is the part of the life cycle that begins just after fertilization of the female egg cell by the male sp ...

nal development of some

species A species () is often defined as the largest group of organisms in which any two individuals of the appropriate sexes or mating types can produce fertile offspring, typically by sexual reproduction. It is the basic unit of Taxonomy (biology), ...

. In Silurana tropicalis, exposure to

s like cyanazine may cause severe abnormalities. It is unclear whether these effects could be seen in humans too. Also, eye defects in

foetuses A fetus or foetus (; : fetuses, foetuses, rarely feti or foeti) is the unborn offspring of a viviparous animal that develops from an embryo. Following the embryonic stage, the fetal stage of development takes place. Prenatal development is a ...

could be the effect of

toxic properties 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 ...

of cyanazine. * Synergistic toxicity Different

s appear to have a synergistic effect on specific

animal species A species () is often defined as the largest group of organisms in which any two individuals of the appropriate sexes or mating types can produce fertile offspring, typically by sexual reproduction. It is the basic unit of classification and ...

. In the case of cyanazine,

can cause effects on non-target species like Chironomus tentans.

Atrazine Atrazine ( ) is a Organochlorine compound, chlorinated herbicide of the triazine class. It is used to prevent pre-emergence broadleaf weeds in crops such as maize (corn), soybean and sugarcane and on turf, such as golf courses and residential law ...

is able to influence the activity of

P450 Cytochromes P450 (P450s or CYPs) are a superfamily of enzymes containing heme as a cofactor that mostly, but not exclusively, function as monooxygenases. However, they are not omnipresent; for example, they have not been found in ''Escherichi ...

enzymes in midges and therefore cause increased

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 ...

of these

s.Y. Jin-Clark, M. J. Lydy, and K. Y. Zhu, "Effects of atrazine and cyanazine on chlorpyrifos toxicity in Chironomus tentans (Diptera: Chironomidae)," ''Environ. Toxicol.'', vol. 21, pp. 598–603, 2002.

References

{{Herbicides Triazines Herbicides Suspected teratogens Group 5 herbicides