1.0 2018-10-03 16:32:44 UTC 2020-06-04 20:40:38 UTC BMDB0063604 BMDB63604 atrazine Atrazine is an organic compound consisting of an s-triazine-ring is a widely used herbicide. Its use is controversial due to widespread contamination in drinking water and its associations with birth defects and menstrual problems when consumed by humans at concentrations below government standards. Although it has been banned in the European Union,[2] it is still one of the most widely used herbicides in the world (Wikipedia). Atrazine is a suspected teratogen, causing demasculinization in male northern leopard frog even at low concentrations, and an estrogen disruptor. A 2010 study found that atrazine rendered 75 percent of male frogs sterile and turned one in 10 into females. A 2002 study found that exposure to atrazine caused male tadpoles to turn into hermaphrodites - frogs with both male and female sexual characteristics. But another study, requested by EPA and funded by Syngenta, was unable to reproduce these results. 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, in spite of the restriction that used to be imposed. Its endocrine disruptor effects, possible carcinogenic effect, and epidemiological connection to low sperm levels in men has led several researchers to call for banning it in the US.Rates of biodegradation are affected by atrazine's low solubility, thus surfactants may increase the degradation rate. Though the two alkyl moieties readily support growth of certain microorganisms, the atrazine ring is a poor energy source due to the oxidized state of ring carbon. In fact, the most common pathway for atrazine degradation involves the intermediate, cyanuric acid, in which carbon is fully oxidized, thus the ring is primarily a nitrogen source for aerobic microorganisms. Atrazine may be catabolized as a carbon and nitrogen source in reducing environments, and some aerobic atrazine degraders have been shown to use the compound for growth under anoxia in the presence of nitrate as an electron acceptor, a process referred to as a denitrification. When atrazine is used as a nitrogen source for bacterial growth, degradation may be regulated by the presence of alternative sources of nitrogen. In pure cultures of atrazine-degrading bacteria, as well as active soil communitites, atrazine ring nitrogen, but not carbon are assimilated into microbial biomass. Low concentrations of glucose can decrease the bioavailability, whereas higher concentrations promote the catabolism of atrazine. Tyrone Hayes, Department of Integrative Biology, University of California, notes that all of the studies that failed to conclude that atrazine caused hermaphroditism were plagued by poor experimental controls and were funded by Syngenta, one of the companies that produce the chemical. The U.S. Environmental Protection Agency (EPA) and its independent Scientific Advisory Panel (SAP) examined all available studies on this topic including Hayes' work and concluded that there are 'currently insufficient data' to determine if atrazine affects amphibian development. Hayes, formerly part of the SAP panel, resigned in 2000 to continue studies independently. The EPA and its SAP made recommendations concerning proper study design needed for further investigation into this issue. As required by the EPA, Syngenta conducted two experiments under Good Laboratory Practices (GLP) and inspection by the EPA and German regulatory authorities. The paper concluded 'These studies demonstrate that long-term exposure of larval X. laevis to atrazine at concentrations ranging from 0.01 to 100 microg/l does not affect growth, larval development, or sexual differentiation.' Another independent study in 2008 determined that 'the failure of recent studies to find that atrazine feminizes X. laevis calls into question the herbicide's role in that decline.' A report written in Environmental Science and Technology (May 15, 2008) cites the independent work of researchers in Japan, who were unable to replicate Hayes' work. 'The scientists found no hermaphrodite frogs; no increase in aromatase as measured by aromatase mRNA induction; and no increase in vitellogenin, another marker of feminization.' 2-Chloro-4-(ethylamino)-6-(isopropylamino)-1,3,5-triazine 2-Chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine 2-Chloro-4-ethylamino-6-isopropylamino-S-triazine 2-CHLORO-4-isopropylamino-6-ethylamino-1,3,5-triazine 2-Ethylamino-4-isopropylamino-6-chloro-S-triazine 6-Chloro-N-ethyl-n'-(1-methylethyl)-1,3,5-triazine-2,4-diamine 6-Chloro-N-ethyl-n'-isopropyl-1,3,5-triazine-2,4-diamine 1-Chloro-3-(ethylamino)-5-(isopropylamino)-2,4,6-triazine 1-Chloro-3-(ethylamino)-5-(isopropylamino)-S-triazine 2-Aethylamino-4-chlor-6-isopropylamino-1,3,5-triazin 2-Chloro-4-(2-propylamino)-6-(ethylamino)-S-triazine 2-Chloro-4-(ethylamino)-6-(isopropylamino)-S-triazine 2-Chloro-4-ethylamineisopropylamine-S-triazine 2-Chloro-4-isopropylamino-6-ethylamino -1,3,5-triazine 6-Chloro-4-(ethylamino)-2-(isopropylamino)-S-triazine 6-Chloro-N-ethyl-n'-(propan-2-yl)-1,3,5-triazine-2,4-diamine Aatram Aatrex Aatrex 4l Aatrex 4LC Aatrex 80W Aatrex nine-O Actinite PK Akticon Aktikon Aktikon PK Aktinit a Aktinit PK Argezin Atazinax Atraflow Atraflow plus Atranex Atrasine Atrataf Atratol Atratol a Atrazin Atrazine 4l Atrazine 80W Atred Atrex Attrex ATZ Azinotox 500 Candex Cekuzina-T Chromozin Crisamina Crisatrina Crisazine Cyazin Farmco atrazine Farmozine Fenamin Fenamine Fenatrol Fogard Gesaprim Gesaprim 50 Gesoprim Griffex Griffex 4l Herbatoxol Hungazin Hungazin PK Inakor Laddock Maizina Mebazine Oleogesaprim Pitezin Primatol Primatol a Primaze Primoleo Radazin Radazin T Radizin Radizine Strazine Triazine a 1294 Vectal Vectal SC Weedex a Wonuk Zeaphos Zeapos Zeazin Zeazine Zeopos Gesamprim C8H14ClN5 215.683 215.09377318 6-chloro-N2-ethyl-N4-(propan-2-yl)-1,3,5-triazine-2,4-diamine atrazine 1912-24-9 CCN=C1NC(NC(Cl)=N1)=NC(C)C 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) MXWJVTOOROXGIU-UHFFFAOYSA-N belongs to the class of organic compounds known as chloro-s-triazines. These are aromatic compounds containing a 1,3,5-triazine ring that is substituted at the 2-position with a chlorine atom. Organic compounds Organoheterocyclic compounds Triazines 1,3,5-triazines Chloro-s-triazines Aryl chlorides Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Organochlorides Organonitrogen compounds Organopnictogen compounds Aromatic heteromonocyclic compound Aryl chloride Aryl halide Azacycle Chloro-s-triazine Heteroaromatic compound Hydrocarbon derivative Organic nitrogen compound Organochloride Organohalogen compound Organonitrogen compound Organopnictogen compound Aromatic heteromonocyclic compounds <i>s</i>-triazine Triazine herbicides chloro-1,3,5-triazine diamino-1,3,5-triazine logp 1.69 ALOGPS logs -2.78 ALOGPS logp 2.2 ChemAxon pka_strongest_acidic 14.48 ChemAxon pka_strongest_basic 3.2 ChemAxon iupac 6-chloro-N2-ethyl-N4-(propan-2-yl)-1,3,5-triazine-2,4-diamine ChemAxon average_mass 215.683 ChemAxon mono_mass 215.09377318 ChemAxon smiles CCN=C1NC(NC(Cl)=N1)=NC(C)C ChemAxon formula C8H14ClN5 ChemAxon 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) ChemAxon inchikey MXWJVTOOROXGIU-UHFFFAOYSA-N ChemAxon polar_surface_area 62.73 ChemAxon refractivity 62.22 ChemAxon polarizability 22.58 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::NmrOneD 2271 Specdb::NmrOneD 2971 Specdb::CMs 25366 Specdb::CMs 29690 Specdb::CMs 31700 Specdb::CMs 102271 Specdb::CMs 102272 Specdb::CMs 134982 Specdb::CMs 142716 Specdb::EiMs 401 Specdb::MsMs 45405 Specdb::MsMs 45406 Specdb::MsMs 45407 Specdb::MsMs 143736 Specdb::MsMs 143737 Specdb::MsMs 143738 Specdb::MsMs 441406 Specdb::MsMs 441407 Specdb::MsMs 441408 Specdb::MsMs 441409 Specdb::MsMs 441410 Specdb::MsMs 442003 Specdb::MsMs 442004 Specdb::MsMs 442005 Specdb::MsMs 442006 Specdb::MsMs 442007 Specdb::MsMs 442008 Specdb::MsMs 442009 Specdb::MsMs 442010 Specdb::MsMs 442011 Specdb::MsMs 442012 Specdb::MsMs 442013 Specdb::MsMs 442014 Specdb::MsMs 442015 Specdb::MsMs 442016 Milk 0.00927 - 0.0185 uM Commercial pasteurized full milk (n=45) Tekel' J, Farkas P, Schultzova K, Kovacicova J, Szokolay A: Analysis of triazine herbicides residues in butter and pasteurized milk. Z Lebensm Unters Forsch. 1988 Apr;186(4):319-22. 3381593 DB07392 2169 C06551 15930 2256 ATRAZINE Atrazine Tekel' J, Farkas P, Schultzova K, Kovacicova J, Szokolay A: Analysis of triazine herbicides residues in butter and pasteurized milk. Z Lebensm Unters Forsch. 1988 Apr;186(4):319-22. 3381593