CHEBI:15930 - atrazine

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ChEBI Name atrazine
ChEBI ID CHEBI:15930
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:2916, CHEBI:49479, CHEBI:13865, CHEBI:22672
Supplier Information ChemicalBook:CB1325292, eMolecules:486473, ZINC000000402767
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Atrazine is a 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 lawns. Atrazine's primary manufacturer is Syngenta and it is one of the most widely used herbicides in the United States, Canadian, and Australian agriculture. Its use was banned in the European Union in 2004, when the EU found groundwater levels exceeding the limits set by regulators, and Syngenta could not show that this could be prevented nor that these levels were safe. At least two significant Canadian farm well studies showed that atrazine was the most common contaminant found. As of 2001, atrazine was the most commonly detected pesticide contaminating drinking water in the U.S.: 44  Studies suggest it is an endocrine disruptor, an agent that can alter the natural hormonal system. However, in 2006 the U.S. Environmental Protection Agency (EPA) had stated that under the Food Quality Protection Act "the risks associated with the pesticide residues pose a reasonable certainty of no harm", and in 2007, the EPA said that atrazine does not adversely affect amphibian sexual development and that no additional testing was warranted. The EPA's 2009 review concluded that "the agency's scientific bases for its regulation of atrazine are robust and ensure prevention of exposure levels that could lead to reproductive effects in humans". However, in their 2016 Refined Ecological Risk Assessment for Atrazine, it was stated that "it is difficult to make definitive conclusions about the impact of atrazine at a given concentration but multiple studies have reported effects to various endpoints at environmentally-relevant concentrations." EPA started a registration review in 2013. The EPA's review has been criticized, and the safety of atrazine remains controversial. EPA has however stated that "If at any time EPA determines there are urgent human or environmental risks from atrazine exposure that require prompt attention, we will take appropriate regulatory action, regardless of the status of the registration review process."
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Formula C8H14ClN5
Net Charge 0
Average Mass 215.68316
Monoisotopic Mass 215.09377
InChI InChI=1S/C8H14ClN5/c1-4-10-7-12-6(9)13-8(14-7)11-5(2)3/h5H,4H2,1-3H3,(H2,10,11,12,13,14)
InChIKey MXWJVTOOROXGIU-UHFFFAOYSA-N
SMILES CCNc1nc(Cl)nc(NC(C)C)n1
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Application(s): herbicide
A substance used to destroy plant pests.
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ChEBI Ontology
Outgoing atrazine (CHEBI:15930) has functional parent 6-chloro-1,3,5-triazine-2,4-diamine (CHEBI:27726)
atrazine (CHEBI:15930) has role environmental contaminant (CHEBI:78298)
atrazine (CHEBI:15930) has role herbicide (CHEBI:24527)
atrazine (CHEBI:15930) has role xenobiotic (CHEBI:35703)
atrazine (CHEBI:15930) is a chloro-1,3,5-triazine (CHEBI:38168)
atrazine (CHEBI:15930) is a diamino-1,3,5-triazine (CHEBI:38170)
Incoming 4-ethylamino-6-isopropylamino-1,3,5-triazin-2-ol (CHEBI:18316) has functional parent atrazine (CHEBI:15930)
IUPAC Name
6-chloro-N-ethyl-N'-(propan-2-yl)-1,3,5-triazine-2,4-diamine
Synonyms Sources
2-chloro-4-(ethylamino)-6-(isopropylamino)-1,3,5-triazine IUBMB
2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine ChemIDplus
2-chloro-4-ethylamino-6-isopropylamino-s-triazine ChemIDplus
2-CHLORO-4-ISOPROPYLAMINO-6-ETHYLAMINO-1,3,5-TRIAZINE PDBeChem
2-ethylamino-4-isopropylamino-6-chloro-s-triazine NIST Chemistry WebBook
6-chloro-N-ethyl-N'-(1-methylethyl)-1,3,5-triazine-2,4-diamine NIST Chemistry WebBook
6-chloro-N-ethyl-N'-isopropyl-1,3,5-triazine-2,4-diamine IUPAC
Atrazine KEGG COMPOUND
atrazine UniProt
Manual Xrefs Databases
43 PPDB
Atrazine Wikipedia
ATRAZINE MetaCyc
ATZ PDBeChem
c0002 UM-BBD
C06551 KEGG COMPOUND
DB07392 DrugBank
HMDB0041830 HMDB
LSM-18990 LINCS
View more database links
Registry Numbers Types Sources
1912-24-9 CAS Registry Number KEGG COMPOUND
1912-24-9 CAS Registry Number ChemIDplus
1912-24-9 CAS Registry Number NIST Chemistry WebBook
612020 Reaxys Registry Number Reaxys
Citations
Chevrier C, Serrano T, Lecerf R, Limon G, Petit C, Monfort C, Hubert-Moy L, Durand G, Cordier S (2014)
Environmental determinants of the urinary concentrations of herbicides during pregnancy: the PELAGIE mother-child cohort (France).
Environment international 63, 11-18 [PubMed:24246238]
[show Abstract]
Fang H, Cai L, Yang Y, Ju F, Li X, Yu Y, Zhang T (2014)
Metagenomic analysis reveals potential biodegradation pathways of persistent pesticides in freshwater and marine sediments.
The Science of the total environment 470-471, 983-992 [PubMed:24239819]
[show Abstract]
Peyre L, Zucchini-Pascal N, Rahmani R (2014)
Atrazine represses S100A4 gene expression and TPA-induced motility in HepG2 cells.
Toxicology in vitro : an international journal published in association with BIBRA 28, 156-163 [PubMed:24211529]
[show Abstract]
Last Modified
25 February 2016