Chemical Property of Atrazine
Chemical Property:
- Appearance/Colour:colourless crystals or white powder
- Vapor Pressure:0.00156mmHg at 25°C
- Melting Point:175 °C
- Refractive Index:1.589
- Boiling Point:368.5 °C at 760 mmHg
- PKA:pKa 1.64 (Uncertain)
- Flash Point:176.7 °C
- PSA：62.73000
- Density:1.269 g/cm3
- LogP:1.92310
- Storage Temp.:APPROX 4°C
- Water Solubility.:Slightly soluble. 0.007 g/100 mL
- XLogP3:2.6
- Hydrogen Bond Donor Count:2
- Hydrogen Bond Acceptor Count:5
- Rotatable Bond Count:4
- Exact Mass:215.0937732
- Heavy Atom Count:14
- Complexity:166
- Purity/Quality:
-
97% tech *data from raw suppliers
Atrazine *data from reagent suppliers
Safty Information:
- Pictogram(s):
Xn,
N
- Hazard Codes:Xn;N,N,Xn,T,F,Xi
- Statements:
43-48/22-50/53-39/23/24/25-23/24/25-11-38-36/37/38-20/21/22-52/53
- Safety Statements:
2-36/37-60-61-45-16-7-36-26
- MSDS Files:
-
SDS file from LookChem
Total 1 MSDS from other Authors
Useful:
- Chemical Classes:Pesticides -> Herbicides, Triazine
- Canonical SMILES:CCNC1=NC(=NC(=N1)Cl)NC(C)C
- Inhalation Risk:A harmful concentration of airborne particles can be reached quickly when dispersed.
- Effects of Short Term Exposure:The substance is severely irritating to the eyes.
- Effects of Long Term Exposure:The substance may have effects on the liver. This may result in tissue lesions.
-
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. 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.
-
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. 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. 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. 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.
