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| | Atrazine Chemical Properties |
| Melting point | 175°C | | Boiling point | 200°C | | density | 1.187 | | vapor pressure | 0Pa at 25℃ | | refractive index | 1.6110 (estimate) | | Fp | 11 °C | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | solubility | DMSO: 83.33 mg/mL (386.36 mM) | | pka | pKa 1.64 (Uncertain) | | form | Crystalline | | color | Crystals | | Water Solubility | Slightly soluble. 0.007 g/100 mL | | Merck | 14,871 | | BRN | 612020 | | Exposure limits | OSHA PEL: TWA 5 mg/m3; ACGIH TLV: TWA 5 mg/m3. | | Stability: | Stable. Incompatible with strong oxidizing agents. | | LogP | 2.59 at 20℃ and pH7.31-7.51 | | Surface tension | 57.6mN/m at 30mg/L and 21℃ | | Dissociation constant | 1.56 at 20℃ | | CAS DataBase Reference | 1912-24-9(CAS DataBase Reference) | | IARC | 3 (Vol. 53, 73) 1999 | | NIST Chemistry Reference | Atrazine(1912-24-9) | | EPA Substance Registry System | Atrazine (1912-24-9) |
| | Atrazine Usage And Synthesis |
| Description | Atrazine appears as an odorless white powder, belonging to a selective triazine herbicide. It can be used for stopping the growth of broadleaf and grassy weeds associated with crops including sorghum, maize, sugarcane, lupins, pine, eucalypt plantations and triazine-tolerant canola.
According to the statistics of US in 2014, it ranks 2nd as one of the most widely used herbicide, only after glyphosate. Atrazine exerts its effect through targeting on the photosynthesis II system of the weeds, blocking the photosynthesis process and causing the death of weeds. It could be manufactured through the treatment of cyanuric chloride with ethylamine and isopropyl amine. However, it has been shown that it has certain toxicity on humans and other animals through targeting on the endocrine systems.
| | Chemical Properties | Atrazine is a white, odorless, crystalline solid or powder which is often mixed with a flammable liquid. Atrazine is generally found as a dibromide salt. It has a solubility of 0.003% by weight in water and a vapor pressure of <0.0000003mmHg at 20 °C (68 °F). | | Uses | Atrazine is used as a selective herbicide to control broadleaf and grassy weeds for agriculture and other land not used for crops. In agriculture, atrazine is used on corn, sugarcane, and pineapple and for orchards, sod, tree plantations, and rangeland. Atrazine is moderately persistent in the environment because of its low solubility. It can be detected in the water table and in the upper layers of the soil profile in many areas (Huang and Frink, 1989). The Environmental Protection Agency (EPA) reported that atrazine was one of the two most commonly used agricultural herbicides in 2007 (EPA, 2011). It is an active ingredient in many brands, including Actinite PK, Atranex, Atrasine, Atrataf, Atrazin, Chromozin, Cyazin, Primatol A, Primase, AAtre, Griffex, and Weedex. | | Reference | https://en.wikipedia.org/wiki/Atrazine
http://passel.unl.edu/pages/informationmodule.php?idinformationmodule=939154153&topicorder=5&maxto=8
https://pubchem.ncbi.nlm.nih.gov/compound/atrazine#section=Biomolecular-Interactions-and-Pathways
| | Description | A major effort in evaluating the toxicity of the triazines is the
cumulative risk assessment (CRA) conducted by US Environmental
Protection Agency (EPA) as part of the tolerance reassessment
process under the Food Quality Protection Act
(FQPA) of 1996. The CRA (released 2006) was conducted for
triazines as a common mechanism group (CMG), determined
to have a ‘common mechanism of toxicity’ in acting the same
way in the body, that is, the same toxic effect occurs in the same
organ or tissue by essentially the same sequence of major
biochemical events. EPA determined that atrazine, simazine,
propazine, and the metabolites desethyl-s-atrazine (DEA),
desisopropyl-s-atrazine (DIA), and diaminochlorotriazine
(DACT) are considered as a CMG due to their ability to cause
neuroendocrine- and endocrine-related developmental, reproductive,
and carcinogenic effects. Other triazines, such as
ametryn, prometryn, prometon, metsulfuron methyl, trisulfuron,
chlorsulfuron, and DPX-M6316, were excluded
because these triazines do not share the toxicity profile of the
CMG triazines. Hydroxyatrazine was excluded based on the
lack of mammary tumor induction and no compelling
evidence of neuroendocrine-related toxicity. Propazine was
excluded from the cumulative assessment group (CAG)
because exposures to propazine are not anticipated via any of
the relevant exposure pathways. Therefore, the cumulative
assessment included only atrazine, simazine, DEA, DIA, and
DACT, referred to as ‘triazine residues.’
For the triazines, the major toxicity of concern involves the
neuroendocrine system with the key toxicity mechanism being
luteinizing hormone (LH)-dependent effects. The changes in
circulating endocrine hormones regardless of rat strain is the
basis for assuming commonality of mechanism, which were
noted in the same range of doses for these triazines.
The relevance of the induction of mammary tumors in
female Sprague–Dawley (SD) rats to humans continues to
be a subject of discussion and research on the endocrine
effects of triazines. Another consideration is whether the
chemicals’ effects on endocrine responses have an impact on reproduction, development, and the brain related or unrelated
to carcinogenesis. Significant research into the mechanism of
mammary tumor formation was conducted in which the effects
of atrazine, simazine, and other triazines were studied on estrus
cycle, estrogen-mediated responses, estrogen receptor binding,
and hormonal induction and metabolism in several species,
but mostly in the rat. Both the in vivo and in vitro data suggest
that atrazine and simazine disrupt ovarian cycling and induce
mammary tumors in female SD rates, and alteration of the
estrous state is directly associated with the incidence of
mammary tumors.
Atrazine and its metabolites appear to affect reproductive
function of the male as well as the female reproductive and
development parameters. However, they have not been tested
with exposure at all critical periods of development in the
young, evaluated in standard guideline neurotoxicity assay, and
the earlier reproductive toxicity studies did not include sensitive
measures of endocrine disruption that are now included.
Additional studies have been published since the CRA in 2006.
The US EPA FIFRA panel reevaluated the database and reaffirmed
the conclusion on the toxicity of the triazines and the
mammary tumor determination in 2010. | | Chemical Properties | Atrazine is a colorless, crystalline solid. Although atrazine is very stable, it is only slightly
soluble in water, but soluble in N-pentane, chloroform, dimethyl sulfoxide, ethyl acetate,
diethyl ether, and methanol. Atrazine is a broad-spectrum triazine herbicide and is used
as a selective herbicide for weed control in corn and asparagus, in the culture of sugarcane
and pineapple. Additionally, it is used as a total herbicide on roads and public places as well
as on uncultivated ground in combination with amitrol, bromacil, dalapon, and growth
promoters. Atrazine inhibits photosynthesis and other metabolic processes in plants. There
are no natural sources of atrazine. It is produced from cyanuric acid chloride with ethylamine
and isopropylamine. The reaction takes place successively in tetrachloromethane.
All atrazine produced is released into the environment. The formulations include granules,
water dispersible granules, liquid, suspension concentrate, wettable powder, and a combination
with many other herbicides. Atrazine is compatible with various insecticides and
fungicides.
Atrazine was banned in the European Union (EU) in 2004 because of its persistent
groundwater contamination. In the United States, however, atrazine is one of the most
widely used herbicides, with 76 million pounds of it applied each year. It is probably the
most commonly used herbicide in the world. | | Uses | Preemergence and postemergence herbicide for control of some annual grasses and
broad-leaved weeds in corn, fallow land, rangeland, sorghum, non-cropland, certain trop ical plantations, evergreen nurseries, fruit crops and lawns. | | Uses | Chlorotriazine herbicides have the characteristic triazine
(three-nitrogen) aromatic ring, with one chlorine substituent.
Chloro-s-triazines may have substitution at the R1 (2 position)
by chlorine, thiomethyl, or methoxy. The more extensively
studied ones include atrazine (6-chloro-N-ethyl-N0-isopropyl-
1,3,5-triazine-2,4-diamine), simazine (2-chloro-4,6-bis
(ethylamino)-s-triazine), propazine (2-chloro-4,6-bis
(isopropylamino)-s-triazine), and terbuthylazine (2-(tertbutylamino)-
4-chloro-6-(ethylamino)-s-triazine).
Atrazine and simazine are selective pre- and postemergence
herbicides used on crops for control of broad leaf and grassy
weeds and in rights-of-way maintenance. Atrazine, first marketed
in 1957, is widely used on cauliflower, corn, sorghum,
and sugarcane, and in noncropped areas such as wheat fallow.
Simazine, introduced in 1956, is used on corn, almonds,
grapes, and oranges. Major triazine use occurs in the midwestern
cornbelt region of the United States. | | Uses | Atrazine is widely used as a selective herbicide to control
broadleaf and grassy weeds in corn, sorghum, rangeland,
sugarcane, orchards, pineapple, and turf grass sod. It is also
used for selective weed control in conifer restoration and
Christmas tree plantations. It is also used as a nonselective
herbicide for vegetation control in noncrop land. | | Production Methods | Atrazine is prepared by reacting cyanuric chloride with one
equivalent of ethylamine, followed by one equivalent of
isopropylamine in the presence of an acid-binding agent. | | Definition | ChEBI: A diamino-1,3,5-triazine that is 1,3,5-triazine-2,4-diamine substituted by a chloro group at position 6 while one of hydrogens of each amino group is replaced respectively by an ethyl and a propan-2-yl group. | | General Description | White crystalline solid. Melting point 173-175°C. Sinks in water. A selective herbicide used for season-long weed control in a variety of crops. | | Air & Water Reactions | Insoluble in water. | | Reactivity Profile | Atrazine undergoes slow hydrolysis at 158° F under neutral conditions. Hydrolysis is more rapid in acidic or alkaline conditions. Forms salts with acids . | | Hazard | Hematologic, preproductive and develop-
mental effects. Questionable carcinogen.
| | Health Hazard | Acute oral toxicity of atrazine in experimen-tal animals was found to be moderate. Inhumans, the acute and chronic toxicity islow. There is no reported case of poisoning. The toxic symptoms in animals includeataxia, dyspnea, and convulsion. Other symptoms are abdominal pain, diarrhea, vomitingand irritation of mucous membranes. Theoral LD50 values in rats and rabbits are 672and 750 mg/kg, respectively (NIOSH 1986).
The toxicity signs reported in rabbitsincluded conjuctivitis, excessive salivation,sneezing, and muscle weakness (Salem et al1985a,b). There was a gradual reductionin the hemoglobin content and erythrocyteand leukocyte count; an increase in glucose,cholesterol, total proteins, and the enzymeserum transminases. The oral LD50 valuereported is 3320 mg/kg. Rabbits fed atrazine-treated maize for 6 months developed loss ofappetite, debility, progressive anemia, enteritis, and muscle weakness. Most organs wereaffected.
Rats treated orally with atrazine 12 mg/100 g for 7 days were found to contain theunchanged atrazine, as well as its metabolites in the liver, kidney, and brain. Thehighest concentration of unchanged atrazinewas detected in the kidney, while its majormetabolite, diethylatrazine, was found in thebrain (Gojmerac and Kniewald 1989). Whena single dose of atrazine (0.53 mg) was administered to rats by gavage, 15% of itwas retained in the body tissues, mostly inthe liver, kidneys, and lungs, and the restexcreted out in 72 hours.
Donna and coworkers (1986) conducteda 130-month study to test the carcinogenic-ity of atrazine in male Swiss albino mice.Intraperitoneal administration of a total doseof 0.26 mg/kg showed a statistically sig-nificant increase of plasma cell type andhistiocytic type of lymphomas in the ani-mals. IARC has listed atrazine as possiblycarcinogenic to human (Group 2B Carcinogen) (IARC 1991). Lifetime administrationof atrazine in rats caused mammary tumors.EPA has classified atrazine as a possiblehuman carcinogen. It produced severe eyeirritation in rabbit. Irritant action on skinis mild.
Atrazine has been detected in surface- andgroundwaters in many parts of the UnitedStates. The U.S. EPA has set the MCL(maximum contaminant level) for atrazinein the drinking waters as 3μg/L. In otherwords, the maximum permissible level inwater delivered to any user of a public watersystem must not be at this level or exceedthis level. | | Fire Hazard | Special Hazards of Combustion Products: Irritating hydrogen chloride and toxic oxides of nitrogen may be formed. | | Agricultural Uses | Herbicide, Plant growth regulator: Not approved for use in EU countries. A U.S.
EPA restricted Use Pesticide (RUP). In 2009 a report from
the Natural Resources Defense Council (NRDC) reported
that atrazine is the most commonly detected pesticide in
U.S. waters. Atrazine is a selective pre-and post-emergence herbicide used for the control of broadleaf and
grassy weeds in crops, such as corn (field and sweet),
guava, hay, macadamia nuts, range grasses for the establishment of permanent grass cover on range lands and pastures in Oklahoma, Nebraska, Texas and Oregon, wheat,
residential and recreational turf and sod farms, sorghum,
sugarcane, pineapples, and Christmas trees and ornamentals. It is also used in forestry and, at higher application
rates, for non-selective weed control in non-crop areas.
It is the most widely used pesticide in the United States.
Use data from 1900 to 1997 indicate that approximately
76.5 million pounds of atrazine active ingredient is used
domestically each year. Certified herbicide workers may
spread atrazine on crops or crop lands as a powder, liquid,
or in a granular form. Atrazine is usually used in the spring
and summer months. For it to be active, atrazine needs to
dissolve in water and enter the plants through their roots.
It then acts in the shoots and leaves of the weed to stop
photosynthesis. Atrazine is taken up by all plants, but in
plants not affected by atrazine it is broken down before it
can have an effect on photosynthesis. Atrazine degrades
into hydroxy compounds and chlorotriazine degradates.
The application of atrazine to crops as a herbicide accounts
for almost all of the atrazine that enters the environment,
but some may be released from manufacture, formulation,
transport, and disposal. Atrazine does not tend to accumulate in living organisms such as algae, bacteria, clams, or
fish, and, therefore, does not tend to build up in the food
chain. Atrazine can be applied by ground boom sprayer,
aircraft, tractor-drawn spreader, rights-of-way sprayer,
hand-held sprayer, backpack sprayer, lawn handgun, pushtype spreader, and bellygrinder. | | Agricultural Uses | Atrazine is the generic name for 2-chloro-4-ethylamino-
6-isopropylamino-s-triazine.A trazine is an example of
photosynthesis inhibitors and herbicides.
Atrazine was the first s-triazine used in maize. The use
of this herbicide and others in the same group has
expanded to selective application in perennial crops and
orchids as well as for non-crop and industrial sites. | | Trade name | AI3-28244®; AATRAM®; AATREX®;
ACTINITE PK®; ACTINIT A®; AGIMIX®
Atrazine; AKTIKON®; AKTIKON PK®; AKTINIT
A®; ALAZINE®; ARGEZIN®; ATAZINAX®;
ATERBUTEX®; ATERBUTOX®; ATLAS ATRAZINE®;
ATLAZIN D-WEED®; ATRANEX®; ATRASINE®;
ATRATAF®; ATRATOL®; ATRAZINEK®;
ATRAZINE 90DF®; ATREX®; AXIOM® Atrazine;
AZINOTOX®; BICEP®; BLADEX/ATRAZINE
(2:1) 80 W®[C]; BUCTRIL + ATRAZINE GEL®[C];
CANDEX®; CEKUZINA-T®; CHROMOZIN®; CO-OP
ATRAZINE®[C]; CRISATRINA®; CRISAZINE®;
CYAZIN®; DOW ATRAZINE 80 W HERBICIDE®[C];
ERUNIT 500 FW®; FARMCO® ATRAZINE;
FENAMIN®; FENATROL®[C]; FIELD MASTER®;
FLOWABLE ATRAZINE®; G 30027®; GEIGY 30,027®;
GESAPRIM®; GESOPRIM®; GRIFFEX®; GRIFFIN
ATRAZINE 90 DRY FLOWABLE HERBICIDE®[C];
HAVILAND ATRAZINE LINURON WEED
KILLER®[C]; HELENA ATRAZINE TECHNICAL®[C];
GUARDSMAN® herbicide (mixture of atrazine and di-
methenamid); HELENA BRAND ATRAZINE®[C];
HERBATOXOL®; HERBIMIX SC®; HERBITRIN 500
BR®; HUNGAZIN®; INAKOR®; LADDOK®; LANCO
ATRAZINE®[C]; LARIAT®; LEADOFF®; MAGIC
CARPET FERTILIZER WITH ATRAZINE®[C];
MALLET PM BROMOXYNIL, ATRAZINE
BROADLEAF HERBICIDE®[C]; MARKSMAN®;
MARZONE ATRAZINE®[C]; MITAC®; NEW
CHLOREA®; NU-TRAZINE 900 DF®; NU-ZINOLE
AA®; OLEOGESAPRIM®; PATRIOT®; PITEZIN®;
POSMIL®; PRIMATOP®; PRIMOLE®; PROKIL
ATRAZINE 80 W®[C]; RADAZIN®; RADIZINE®;
READY MASTER®; RESIDOX®; SHELL® ATRAZINE
80 W HERBICIDE[C]; SIMAZAT®; STRAZINE®
TRIAZINE A 1294; TRIPART® ATRAZINE 50 SC;
VECTAL®; WEEDEX®; WONUK®; ZEAZIN®;
ZEAZINE® | | Pharmacology | In plants, themajor
pathways of atrazine transformation include hydroxylation,
N-dealkylation, and glutathione conjugation. Hydroxylation
of atrazine and other s-triazines occurs in a wide range of plants and is considered a detoxification
mechanism because hydroxyatrazine is not phytotoxic.
Hydroxylation is catalyzed via reaction with the naturally
occurring compound, benzoxazinone (127). A hypothetical
ether-linked intermediate has been proposed to undergoes
hydrolysis to produce hydroxylated triazine and
regenerated benzoxazinone. This reaction occurs in many
susceptible and resistant plant species, and the rate of
this reaction is governed by the amount of benzoxazinone
present in the tissue. The hydroxylation reaction predominates
in root tissue, whereas GSH conjugation is more
prominent in leaf tissue of plants containing a GST that
has substrate specificity for atrazine. Because atrazine
is a photosystem II (PS II) inhibitor, possession of a rapid
detoxification system, such as a specific GST, is paramount
to provide tolerance to this compound. | | Safety Profile | Poison by
intraperitoneal route. Moderately toxic by
ingestion. Mildly toxic by inhalation and skin
contact. An experimental teratogen. Other
experimental reproductive effects. Human
mutation data reported. A skin and severe
eye irritant. Questionable carcinogen with
experimental tumorigenic data. When heated
to decomposition it emits toxic fumes of ClandNOx. | | Potential Exposure | Atrazine is an herbicide and plant
growth regulator used for season-long weed control in corn,
sorghum, and certain other crops. Banned for use as a pesticide
in the EU. US annual use . 75 millon pounds. | | Carcinogenicity | An increase in mammary adenomas
and fibroadenomas was observed in female rats fed
1000 ppm, but not 500 ppm atrazine or less for their lifetime.
An increase in the incidence of mammary carcinomas was
seen at 70, 500, and 1000 ppm, but not at 10 ppm. The
biological significance of these findings is not known but may
be related to a hormonally mediated mechanism. Rats
fed 375 or 750 ppmatrazine for 2 years showed an increase in
mammary tumors in males at 750 ppm. Uterine carcinomas
increased in both groups and the incidence of malignant
tumors also increased in both sexes. | | Environmental Fate | Atrazine is highly persistent in soil. In soil and water, atrazine degrades by hydrolysis, followed by biodegradation by soil microorganisms. Hydrolysis is rapid in acidic or basic environments, but is slower around neutral pH. Sunlight and evaporation do not affect its removal rate. Atrazine can persist for longer than 1 year under dry or cold conditions. It is moderately to highly mobile in soils with low clay or low organic matter content. Because it does not adsorb strongly to soil particles and has a lengthy half-life (60 to >100 days), it has a high potential for groundwater contamination despite being only moderately soluble in water. It is frequently detected in drinking water wells. | | Shipping | UN2763 Triazine pesticides, solid, toxic, Hazard
Class: 6.1; Labels: 6.1-Poisonous materials. | | Toxicity evaluation | According to US EPA, the underlying mechanism for tumor
induction in female SD rats involves a reduction in the release
of gonadotropin releasing hormone (GnRH) from the hypothalamic–
pituitary–gonadal axis in the rats, followed by
attenuation of the afternoon pituitary LH surge, leading to
a lengthening of the estrus cycle that increases estrogen levels
that in turn is associated with an increased incidence of
mammary tumors in SD rats. The decrease GnRH release
follows these postulated events: hypothalamic changes results
in an increase in the release of corticotropin releasing
hormone (CRH), elevated CRH stimulates release of adrenocorticotropic
hormone (ACTH) from the pituitary, elevated
ACTH stimulates production of corticosterone and progesterone
by the adrenal, and some or all of these events
decrease GnRH release. Atrazine and some of its metabolites
act to attenuate the spontaneous preovulatory LH surge, block
the gonadal steroid inducted LH surge and attenuate
concomitant GnRH neuronal activation, inhibit LH secretion,
and increase the concentration of GnRH in the median
eminence (a measure of reduced release). This mode of action
(premature reproductive aging or senescence) hastens the
onset of mammary gland tumors.
The central nervous system (CNS) mode of action that
results in altered pituitary hormone function, especially LH and prolactin (PRL) secretions, occurs in both adults and the
young. The triazine-mediated changes in the hypothalamus–
pituitary–gonadal axis relating to neuroendocrine and
neuroendocrine-related developmental and reproductive
toxicity are considered relevant to humans. On the other hand,
the exact mechanism by which the mode of action changes
neurotransmitters and neuropeptides within the CNS is not
understood. It was noted that although atrazine alters hypothalamic
norepinephrine and dopamine, these effects do not
necessarily represent its primary site of action, but that these
CNS alterations may be a signal of potential upstream effects
on other neurotransmitters. It is unclear if atrazine directly
affects the hypothalamus, setting off the cascade of events, or
affect indirectly through the hypothalamus–pituitary–adrenal
axis or both | | Incompatibilities | Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explosions.
Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides. | | Waste Disposal | Atrazine is hydrolyzed by
either acid or base. The hydroxy compounds are generally
herbicidally inactive, but their complete environmental
effects are uncertain. However, the method appears
suitable for limited use and quantities of triazine. Atrazine
underwent .99% decomposition when burned in a polyethylene
bag, and combustion with a hydrocarbon fuel would
appear to be a generally suitable method for small quantities.
Combustion of larger quantities would probably
require the use of a caustic wet scrubber to remove nitrogen
oxides and HCl from the product gases. |
| | Atrazine Preparation Products And Raw materials |
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