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Chemistry

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Also known as: 1912-24-9, Gesaprim, Oleogesaprim, Chromozin, Aktikon, Atranex
Molecular Formula
C8H14ClN5
Molecular Weight
215.68  g/mol
InChI Key
MXWJVTOOROXGIU-UHFFFAOYSA-N
FDA UNII
QJA9M5H4IM

Atrazine
A selective triazine herbicide. Inhalation hazard is low and there are no apparent skin manifestations or other toxicity in humans. Acutely poisoned sheep and cattle may show muscular spasms, fasciculations, stiff gait, increased respiratory rates, adrenal degeneration, and congestion of the lungs, liver, and kidneys. (From The Merck Index, 11th ed)
1 2D Structure

Atrazine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
6-chloro-4-N-ethyl-2-N-propan-2-yl-1,3,5-triazine-2,4-diamine
2.1.2 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)
2.1.3 InChI Key
MXWJVTOOROXGIU-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCNC1=NC(=NC(=N1)Cl)NC(C)C
2.2 Other Identifiers
2.2.1 UNII
QJA9M5H4IM
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Gesamprim

2.3.2 Depositor-Supplied Synonyms

1. 1912-24-9

2. Gesaprim

3. Oleogesaprim

4. Chromozin

5. Aktikon

6. Atranex

7. Atrazin

8. Argezin

9. Atazinax

10. Atrasine

11. Fenamin

12. Fenatrol

13. Gesoprim

14. Hungazin

15. Pitezin

16. Primatol

17. Primaze

18. Radazin

19. Strazine

20. Zeazine

21. Aatrex

22. Candex

23. Cyazin

24. Inakor

25. Vectal

26. Wonuk

27. Zeazin

28. Cekuzina-t

29. Actinite Pk

30. Aktinit A

31. Atratol A

32. Aktikon Pk

33. Aktinit Pk

34. Weedex A

35. Crisatrina

36. Crisazine

37. Fenamine

38. Aatram

39. Akticon

40. Atrataf

41. Atratol

42. Griffex

43. Radizin

44. Zeapos

45. Atred

46. Atrex

47. Primatol A

48. Hungazin Pk

49. Aatrex Nine-o

50. Vectal Sc

51. Herbatoxol

52. Zeopos

53. Triazine A 1294

54. Aatrex 4l

55. Farmco Atrazine

56. Gesaprim 50

57. Aatrex 80w

58. Aneldazin

59. Gesaprin

60. Radizine

61. Azoprim

62. Maizina

63. 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine

64. Geigy 30,027

65. Shell Atrazine Herbicide

66. 2-chloro-4-ethylamino-6-isopropylamino-s-triazine

67. Hungazin (van)

68. 1,3,5-triazine-2,4-diamine, 6-chloro-n-ethyl-n'-(1-methylethyl)-

69. Aatram 20g

70. Ceasin 50

71. Crisamina

72. Farmozine

73. Laddock

74. Mebazine

75. Fogard

76. 6-chloro-n-ethyl-n'-(1-methylethyl)-1,3,5-triazine-2,4-diamine

77. 2-chloro-4-ethylamineisopropylamine-s-triazine

78. 2-ethylamino-4-isopropylamino-6-chloro-s-triazine

79. A 361

80. Aatrex 4lc

81. Atrazine [ansi:bsi:iso]

82. Atraflow

83. Primoleo

84. Zeaphos

85. Attrex

86. Atraflow Plus

87. S-triazine, 2-chloro-4-(ethylamino)-6-(isopropylamino)-

88. G 30027

89. 1-chloro-3-ethylamino-5-isopropylamino-s-triazine

90. Radazin T

91. Atrazine 4l

92. Griffex 4l

93. Atrazine 80w

94. Azinotox 500

95. 2-chloro-4-(2-propylamino)-6-ethylamino-s-triazine

96. Ai3-28244

97. S-triazine, 2-chloro-4-ethylamino-6-isopropylamino-

98. 2-aethylamino-4-chlor-6-isopropylamino-1,3,5-triazin

99. 1-chloro-3-ethylamino-5-isopropylamino-2,4,6-triazine

100. 102029-43-6

101. 6-chloro-n-ethyl-n'-isopropyl-1,3,5-triazine-2,4-diamine

102. 2-chloro-4-(ethylamino)-6-(isopropylamino)-1,3,5-triazine

103. 6-chloro-n2-ethyl-n4-isopropyl-1,3,5-triazine-2,4-diamine

104. Qja9m5h4im

105. 2-chloro-4-isopropylamino-6-ethylamino -1,3,5-triazine

106. 2-chloro-4-(ethylamino)-6-(isopropylamino)-s-triazine

107. Dtxsid9020112

108. Chebi:15930

109. 2-aethylamino-4-chlor-6-isopropylamino-1,3,5-triazin [german]

110. 2-aethylamino-4-isopropylamino-6-chlor-1,3,5-triazin [german]

111. 6-chloro-n-ethyl-n'-(propan-2-yl)-1,3,5-triazine-2,4-diamine

112. 6-chloro-4-n-ethyl-2-n-propan-2-yl-1,3,5-triazine-2,4-diamine

113. Atrazine 100 Microg/ml In Toluene

114. 1,3,5-triazine-2,4-diamine, 6-chloro-n-ethyl-n'-(1-methylethyl)- (9ci)

115. Atrazine 1000 Microg/ml In Acetone

116. Atrazine 10 Microg/ml In Cyclohexane

117. 2-aethylamino-4-isopropylamino-6-chlor-1,3,5-triazin

118. Atrazine 10 Microg/ml In Acetonitrile

119. Nsc-163046

120. 1-chloro-3-(ethylamino)-5-(isopropylamino)-s-triazine

121. 2-chloro-4-(2-propylamino)-6-(ethylamino)-s-triazine

122. 6-chloro-4-(ethylamino)-2-(isopropylamino)-s-triazine

123. Atrazine 100 Microg/ml In Acetonitrile

124. 2-chloro-4-isopropylamino-6-ethylamino-1,3,5-triazine

125. Dsstox_cid_112

126. 1,3,5-triazine-2,4-diamine, 6-chloro-n2-ethyl-n4-(1-methylethyl)-

127. 6-chloro-2-n-ethyl-4-n-(propan-2-yl)-1,3,5-triazine-2,4-diamine

128. Dsstox_rid_75374

129. Dsstox_gsid_20112

130. Atrazine, Analytical Standard

131. Caswell No. 063

132. 1-chloro-3-(ethylamino)-5-(isopropylamino)-2,4,6-triazine

133. Atrazine [iso]

134. Smr000255992

135. Cas-1912-24-9

136. Ccris 1025

137. Hsdb 413

138. Einecs 217-617-8

139. Unii-qja9m5h4im

140. Epa Pesticide Chemical Code 080803

141. Nsc 163046

142. Brn 0612020

143. Zeapho

144. Fermco Atrazine

145. 6-chloro-n2-ethyl-n4-(propan-2-yl)-1,3,5-triazine-2,4-diamine

146. Primitol A

147. Atrazine Solution

148. Oleogesaprim 200

149. Gesaprim 500

150. Mfcd00041810

151. Atrazine (unlabeled)

152. 2-chloro-4-ethylamino-6-isopropylamino-sym-triazine

153. Spectrum_001821

154. Atrazine [hsdb]

155. Atrazine [iarc]

156. Specplus_000422

157. 6-chloro-n4-ethyl-n2-isopropyl-1,3,5-triazine-2,4-diamine

158. Atrazine [mi]

159. Spectrum2_001880

160. Spectrum3_000821

161. Spectrum4_000661

162. Spectrum5_001954

163. Bmse000835

164. Ec 217-617-8

165. Oprea1_839865

166. Schembl36936

167. Bspbio_002341

168. Kbiogr_001061

169. Kbioss_002326

170. Spectrum330029

171. 2-chloro-4-ethylamino-6-isopropylamine-s-triazine

172. Mls000389718

173. Mls001055469

174. Bidd:er0403

175. Chembl15063

176. Divk1c_006518

177. 2-chloro-4-(ethylamino)-6-(isopropylamino)triazine

178. Spbio_001760

179. Schembl21045984

180. Kbio1_001462

181. Kbio2_002323

182. Kbio2_004891

183. Kbio2_007459

184. Kbio3_001841

185. Atrazine 1000 Ug/ml In Acetone

186. Hms2541c15

187. Hms3604n05

188. Bcp12774

189. Hy-n7091

190. Zinc3078958

191. Tox21_201986

192. Tox21_301021

193. Atrazine 100 Microg/ml In Methanol

194. Atrazine 200 Microg/ml In Methanol

195. Ccg-39357

196. Nsc163046

197. S5171

198. Stl115099

199. 6-chloro-n~2~-ethyl-n~4~-(propan-2-yl)-1,3,5-triazine-2,4-diamine

200. Akos001023901

201. Am84660

202. Db07392

203. Ncgc00090784-01

204. Ncgc00090784-02

205. Ncgc00090784-03

206. Ncgc00090784-04

207. Ncgc00090784-05

208. Ncgc00090784-06

209. Ncgc00090784-07

210. Ncgc00090784-08

211. Ncgc00090784-09

212. Ncgc00090784-10

213. Ncgc00254923-01

214. Ncgc00259535-01

215. Ac-12056

216. As-13785

217. Atrazine 1000 Microg/ml In Acetonitrile

218. Wln: T6n Cn Enj Bmy1&1 Dm2 Fg

219. Atrazine 2000 Microg/ml In Dichloromethane

220. Db-044759

221. Atrazine, Pestanal(r), Analytical Standard

222. Cs-0077590

223. Ft-0602866

224. Ft-0662335

225. C06551

226. F21351

227. 029a436

228. A813475

229. Ag-668/02857017

230. G-30027

231. Q408652

232. 2-aethylamino-4-chlor-6-isopropylamino-1,5-triazin

233. 2-chloro-4-ethyl-amino-6-isopropylamino-s-triazine

234. J-012357

235. Atrazine, Certified Reference Material, Tracecert(r)

236. Brd-k45535217-001-02-2

237. 1-chloro-3-(ethylamino)-5-(isopropylamino)-2,6-triazine

238. 2-chloro-4-(ethylamino)-6-(isopropylamino)-1,5-triazine

239. 1,5-triazine-2,4-diamine, 6-chloro-n-ethyl-n'-(1-methylethyl)-

240. 6-chloranyl-n4-ethyl-n2-propan-2-yl-1,3,5-triazine-2,4-diamine

241. 6-chloro-n-ethyl-n'-(1-methylethyl)-1,5-triazine-2,4-diamine

242. 6-chloro-n4-ethyl-n2-propan-2-yl-1,3,5-triazine-2,4-diamine

243. N-[4-chloro-6-(ethylamino)-1,3,5-triazin-2-yl]-n-isopropylamine

244. 6-chloro-4-n-ethyl-2-n-(propan-2-yl)-1,2,3,4-tetrahydro-1,3,5-triazine-2,4-diimine

245. 6-chloro-n(sup 2)-ethyl-n(sup 4)-isopropyl-1,3,5-triazine-2,4-diamine

246. Atrazine Solution, 100 Mug/ml In Methanol, Pestanal(r), Analytical Standard

247. Atrazine Solution, Certified Reference Material, 1000 Mug/ml In Methyl Tert-butyl Ether

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 215.68 g/mol
Molecular Formula C8H14ClN5
XLogP32.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count4
Exact Mass215.0937732 g/mol
Monoisotopic Mass215.0937732 g/mol
Topological Polar Surface Area62.7 Ų
Heavy Atom Count14
Formal Charge0
Complexity166
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Herbicides

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)


4.2 Absorption, Distribution and Excretion

Atrazine (ATR) is a widely used chlorotriazine herbicide, a ubiquitous environmental contaminant, and a potential developmental toxicant. To quantitatively evaluate placental/lactational transfer and fetal/neonatal tissue dosimetry of ATR and its major metabolites, physiologically based pharmacokinetic models were developed for rat dams, fetuses and neonates. These models were calibrated using pharmacokinetic data from rat dams repeatedly exposed (oral gavage; 5mg/kg) to ATR followed by model evaluation against other available rat data. Model simulations corresponded well to the majority of available experimental data and suggest that: (1) the fetus is exposed to both ATR and its major metabolite didealkylatrazine (DACT) at levels similar to maternal plasma levels, (2) the neonate is exposed mostly to DACT at levels two-thirds lower than maternal plasma or fetal levels, while lactational exposure to ATR is minimal, and (3) gestational carryover of DACT greatly affects its neonatal dosimetry up until mid-lactation. To test the model's cross-species extrapolation capability, a pharmacokinetic study was conducted with pregnant C57BL/6 mice exposed (oral gavage; 5mg/kg) to ATR from gestational day 12 to 18. By using mouse-specific parameters, the model predictions fitted well with the measured data, including placental ATR/DACT levels. However, fetal concentrations of DACT were overestimated by the model (10-fold). This overestimation suggests that only around 10% of the DACT that reaches the fetus is tissue-bound. These rodent models could be used in fetal/neonatal tissue dosimetry predictions to help design/interpret early life toxicity/pharmacokinetic studies with ATR and as a foundation for scaling to humans.

PMID:23958493 Lin Z et al; Toxicol Appl Pharmacol 273 (1): 140-58 (2013)


... The atrazine (ATZ) concentrations in urine samples of the workers collected from an atrazine plant were determined by /a gas chromatograph-electron capture detector/ method /for detecting ATZ and its metabolites (deethylatrazine (DEA), deisopropylatrazine (DIA), deethyldeisopropylatrazine (DEDIA)) in human urine/. The concentration ranges were 0.003 -0.301 mg/L for DEDIA, 0.005 -0.011 mg/L for DEA, 0.006 -0.276 mg/L for DIA, and 0.005 -0.012 mg/L for ATZ.

PMID:18161334 Xu R et al; Se Pu. 25 (5): 758-61 (2007)


Small amount of parent ... atrazine ... /was/ excreted in urine of cows fed unlabeled herbicide for 4 days.

Kearney, P.C., and D. D. Kaufman (eds.) Herbicides: Chemistry, Degredation and Mode of Action. Volumes 1 and 2. 2nd ed. New York: Marcel Dekker, Inc., 1975., p. 170


Seventy-two hr /after ingestion/ 65.5% of radiolabeled atrazine was found in urine of rats, while 20.3% was found in the feces. Less than 0.1% was found in expired air, thus indicating s-triazine ring was not appreciably metabolized to carbon dioxide. Tissue analysis revealed that 15.8% of reactivity was retained, with high concentrations observed in the liver, kidney, and lung, and lower concentrations observed in muscle tissue and fat.

American Conference of Governmental Industrial Hygienists. Documentation of the TLVs and BEIs with Other World Wide Occupational Exposure Values. 7th Ed. CD-ROM Cincinnati, OH 45240-1634 2013., p. 2


For more Absorption, Distribution and Excretion (Complete) data for Atrazine (7 total), please visit the HSDB record page.


4.3 Metabolism/Metabolites

Atrazine (ATR) is a widely used chlorotriazine herbicide, a ubiquitous environmental contaminant, and a potential developmental toxicant. To quantitatively evaluate placental/lactational transfer and fetal/neonatal tissue dosimetry of ATR and its major metabolites, physiologically based pharmacokinetic models were developed for rat dams, fetuses and neonates. These models were calibrated using pharmacokinetic data from rat dams repeatedly exposed (oral gavage; 5mg/kg) to ATR followed by model evaluation against other available rat data. Model simulations corresponded well to the majority of available experimental data and suggest that: (1) the fetus is exposed to both ATR and its major metabolite didealkylatrazine (DACT) at levels similar to maternal plasma levels, (2) the neonate is exposed mostly to DACT at levels two-thirds lower than maternal plasma or fetal levels, while lactational exposure to ATR is minimal, and (3) gestational carryover of DACT greatly affects its neonatal dosimetry up until mid-lactation. To test the model's cross-species extrapolation capability, a pharmacokinetic study was conducted with pregnant C57BL/6 mice exposed (oral gavage; 5mg/kg) to ATR from gestational day 12 to 18. By using mouse-specific parameters, the model predictions fitted well with the measured data, including placental ATR/DACT levels. However, fetal concentrations of DACT were overestimated by the model (10-fold). This overestimation suggests that only around 10% of the DACT that reaches the fetus is tissue-bound. These rodent models could be used in fetal/neonatal tissue dosimetry predictions to help design/interpret early life toxicity/pharmacokinetic studies with ATR and as a foundation for scaling to humans.

PMID:23958493 Lin Z et al; Toxicol Appl Pharmacol 273 (1): 140-58 (2013)


Atrazine (ATR) is a widely used herbicide. There are several types of reactions in its metabolism. Herein, the mechanism of three paths of hydrolysis reactions in its metabolism and predictions of toxicities of its metabolites in the three paths will be presented. The calculation results by B3LYP (Becke, 3-parameter, Lee-Yang-Parr), one of the approaches in density functional theory, indicated that (1) there were three models in the three hydrolysis paths of ATR. The dissociation mechanisms of C(9/11)-N(8/10), C(4/6)-N(8/10), and C-Cl were dealkylation, deamination, and Cl substitution, respectively. (2) The energy barrier of C-Cl dissociation was lower. The dissociation was advantageous in dynamics and the primary reaction in the three hydrolysis paths. In these hydrolysis reactions, the different intermediates had different concentrations because of the impact of the reaction rate. (3) In addition, it was necessary to consider the solvent effect to investigate hydrolysis reaction. The conductor-like polarizable continuum model (CPCM) was used to simulate the hydrolysis reaction in bond length and energy barrier because of the solvent effect. Experimental or predictive results showed that atrazine and its metabolites in the three hydrolysis paths were carcinogenic.

PMID:24807108 Li J et al; J Agric Food Chem 62 (21): 4852-63 (2014)


Compounds of the s-triazine family are among the most heavily used herbicides over the last 30 years. Some of these derivatives are suspected to be carcinogens. In this study the identity of specific phase-I enzymes involved in the metabolism of s-triazine derivatives (atrazine, terbuthylazine, ametryne, and terbutryne) by human liver microsomes was determined. Kinetic studies demonstrated biphasic kinetics for all pathways examined (S-oxidation, N-dealkylation, and side-chain C-oxidation). Low Km values were in a range of about 1-20 uM, whereas high Km values were up to 2 orders of magnitude higher. For a correlation study, 30 human liver microsomal preparations were screened for seven specific P450 activities, and these were compared to activities for the metabolites derived from these s-triazines. A highly significant correlation in the high-affinity concentration range was seen with cytochrome P450 1A2 activities. Chemical inhibition was most effective with alpha-naphthoflavone an furafylline at low s-triazine concentrations and additionally with ketoconazole and gestodene at high substrate concentrations. Studies with 10 heterologously expressed P450 forms demonstrated that several P450 enzymes are capable of oxidizing these s-triazines, with different affinities and regioselectivities. P450 1A2 was confirmed to be the low-Km P450 enzyme involved in the metabolism of these s-triazines. A potential participation of flavin-containing monooxygenases (FMOs) in sulfoxidation reactions of the thiomethyl derivatives ametryne and terbutryne in human liver was also evaluated. Sulfoxide formation in human inhibition indicated no significant involvement of flavin-containing monooxygenases. Finally, purified recombinant FMO3, the major flavin-containing monooxygenase in human liver, exhibited no significant activity (< 0.1 nmol (nmol of FMO3)-1 min-1) in the formation of the parent sulfoxides of ametryne and terbutryne. Therefore, P450 1A2 alone is likely to be responsible for the hepatic oxidative phase-I metabolism of the s-triazine derivatives in exposed humans.

PMID:9305587 Lang DH et al; Chemical Research in Toxicology 10 (9): 1037-1044 (1997)


A large number of urinary metabolites was isolated and 15.8% was detected in the carcasses at 72 hr post-exposure. Dealkylation of atrazine in vitro, predominated over glutathione conjugation. Metabolites identified from rat and rabbit urine contained an intact triazine ring suggesting initial loss of ethyl or methyl groups from the alkyl side chains. In the miniature pig, atrazine and its metabolites were seen in urine for slightly more than 24 hr; diethylatrazine was also identified. Excretion by sheep and cattle is rapid with no residues seen in the milk of cows receiving 5 ppm atrazine in the diet for 4 days.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V4 1246


For more Metabolism/Metabolites (Complete) data for Atrazine (16 total), please visit the HSDB record page.


4.4 Biological Half-Life

The whole body half-life of elimination /in rats/ was determined as 31.3 +/- 2.8 hours...

California Environmental Protection Agency/Department of Pesticide Regulation; Toxicology Data Review Summary for Atrazine (1912-24-9) p.31 (January 28, 2008). Available from, as of October 17, 2017: https://www.cdpr.ca.gov/docs/risk/toxsums/toxsumlist.htm


4.5 Mechanism of Action

Atrazine (ATZ) is probably the most widely used herbicide in the world. However there are still many controversies regarding its impacts on human health. Our investigations on the role of pesticides in liver dysfunctions have led us to detect an inhibition of FSP1 expression of 70% at 50 um and around 95% at 500 uM of ATZ (p<0.01). This gene encodes the protein S100a4 and is a clinical biomarker of epithelial-mesenchymal transition (EMT), a key step in the metastatic process. Here we investigated the possible effect of ATZ on cell migration and noticed that it prevents the EMT and motility of the HepG2 cells induced by the phorbol ester TPA. ATZ decreases Fak pathway activation but has no effect on the Erk1/2 pathway known to be involved in metastasis in this cell line. These results suggest that ATZ could be involved in cell homeostasis perturbation, potentially through a S100a4-dependant mechanism.

PMID:24211529 Peyre L et al; Toxicol In Vitro 28 (2): 156-63 (2014)


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