SIMAZINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H12ClN5
Molecular Weight	201.657
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCNC1=NC(NCC)=NC(Cl)=N1

InChI

InChIKey=ODCWYMIRDDJXKW-UHFFFAOYSA-N

InChI=1S/C7H12ClN5/c1-3-9-6-11-5(8)12-7(13-6)10-4-2/h3-4H2,1-2H3,(H2,9,10,11,12,13)

HIDE SMILES / InChI

Molecular Formula	C7H12ClN5
Molecular Weight	201.657
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17193734
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/28486186 | https://www.ncbi.nlm.nih.gov/pubmed/25078261 | https://www.ncbi.nlm.nih.gov/pubmed/26955487

Simazine is a selective triazine herbicide, that used to control broad-leaved weeds and annual grasses in a field, berry fruit, vegetable and ornamental crops, on turfgrass, and in orchards and vineyards. At higher rates, it is used for nonselective weed control in industrial areas. Before 1992, simazine was used to control submerged weeds and algae in large aquariums, farm ponds, fish hatcheries, swimming pools, ornamental ponds and cooling towers. Simazine is available in wettable powder, water dispersible granule, liquid and granular formulations. Simazine is highly toxic if inhaled, moderately toxic if ingested, and slightly toxic via dermal exposure. No cases of poisoning in humans have been reported from ingestion of Simazine.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
photosynthesis 1 Target ID: GO:0015979 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17193734	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Disturbed relaxin signaling pathway and testicular dysfunction in mouse offspring upon maternal exposure to simazine.	2012	22984576
Urinary biomarkers of prenatal atrazine exposure and adverse birth outcomes in the PELAGIE birth cohort.	2011-07	21367690
Activity profiles of 309 ToxCast™ chemicals evaluated across 292 biochemical targets.	2011-03-28	21251949
In vivo alternative assessment of the chemicals that interfere with anterior pituitary POMC expression and interrenal steroidogenesis in POMC: EGFP transgenic zebrafish.	2010-11-01	20732339
Impact of environmental chemicals on key transcription regulators and correlation to toxicity end points within EPA's ToxCast program.	2010-03-15	20143881
Chlorotriazine herbicides and metabolites activate an ACTH-dependent release of corticosterone in male Wistar rats.	2009-11	19690231
Effect of a subchronic exposure to simazine on energetic metabolism of common carp (Cyprinus carpio).	2009-02	19130373
Trial femoral head loss in to the soft tissues of pelvis during primary total hip replacement: a case report.	2008-09-12	18789144
Occurrence and fate of pesticides in four contrasting agricultural settings in the United States.	2008-05-06	18453432
Effects of possible endocrine disruptors on MyD88-independent TLR4 signaling.	2008-03	18177342
Atrazine-induced aromatase expression is SF-1 dependent: implications for endocrine disruption in wildlife and reproductive cancers in humans.	2007-05	17520059
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006-11	16497524
Effects of possible endocrine disrupting chemicals on bacterial component-induced activation of NF-kappaB.	2006-10	17015962
Sorption of pesticides on kaolinite and montmorillonite as a function of hydrophilicity.	2006	16753953
Transgenic rice plants expressing human CYP1A1 remediate the triazine herbicides atrazine and simazine.	2005-11-02	16248553
Simazine biodegradation in soil: analysis of bacterial community structure by in situ hybridization.	2005-09	16015577
The combined antiandrogenic effects of five commonly used pesticides.	2004-11-15	15519604
Effect of endocrine disrupting chemicals on lipopolysaccharide-induced tumor necrosis factor-alpha and nitric oxide production by mouse macrophages.	2004-07	15256756
Induction of apoptosis by yomogin in human promyelocytic leukemic HL-60 cells.	2004-07	15256749
Measured concentrations of herbicides and model predictions of atrazine fate in the Patuxent River estuary.	2004-04-13	15074811
Potential mechanisms responsible for chlorotriazine-induced alterations in catecholamines in pheochromocytoma (PC12) cells.	2003-10-31	14550852
Simazine and metolachlor removal by subsurface flow constructed wetlands.	2003-05-30	12772955
Prostate cancer risk in California farm workers.	2003-03	12661182
Movement of simazine in runoff water and weed control from citrus orchard as affected by reduced rate of herbicide application.	2003-02	12688468
Simazine runoff from citrus orchards affected by shallow mechanical incorporation.	2003-01-29	12549545
Influence of plant age and size on simazine toxicity and uptake.	2002-12-10	12469861
Selective sensing of triazine herbicides in imprinted membranes using ion-sensitive field-effect transistors and microgravimetric quartz crystal microbalance measurements.	2002-11	12475039
Field effects of simazine at lower trophic levels--a review.	2002-09-16	12398331
Fate of pesticides in tropical soils of Brazil under field conditions.	2002-02-12	11837430
Differentiating nonpoint sources of deisopropylatrazine in surface water using discrimination diagrams.	2001-10-02	11577893
Effects of chloro-s-triazine herbicides and metabolites on aromatase activity in various human cell lines and on vitellogenin production in male carp hepatocytes.	2001-10	11675267
Herbicide transport to surface waters at field and watershed scales in a Mediterranean vineyard area.	2001-06-13	11401289
Major herbicides in ground water: results from the National Water-Quality Assessment.	2001-06-13	11401272
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.	2001-03	11258977
Optimizing microwave-assisted solvent extraction (MASE) of pesticides from soil.	2001-01	11281258
Role of prolactin in chloro-S-triazine rat mammary tumorigenesis.	2000-11	11071396
Effects of selected herbicides on cytokine production in vitro.	2000-05-19	10883730
2-Chloro-s-triazine herbicides induce aromatase (CYP19) activity in H295R human adrenocortical carcinoma cells: a novel mechanism for estrogenicity?	2000-03	10746939
Changes in rat liver cytochrome P450 enzymes by atrazine and simazine treatment.	1998-07	9711812
The inhibition of estrogen receptor-mediated responses by chloro-S-triazine-derived compounds is dependent on estradiol concentration in yeast.	1996-10-03	8858116
Failure of chloro-S-triazine-derived compounds to induce estrogen receptor-mediated responses in vivo and in vitro.	1996-03	8812239

Patents

Sample Use Guides

In Vivo Use Guide

Rats and guinea pigs fed 100 mg/kg daily for 6 months had decreased weight gain, increased white blood cell counts, decreased blood cholinesterase activity and deterioration and inflammation of the stomach. In a 28-day study, oral doses of 2,500 mg/kg/day to rats resulted in stomach ulcers, damage to the small intestine, and death

Route of Administration: Oral

In Vitro Use Guide

MCF-7 and MDA-MB-231 cells were seeded into 96-well plates either in maintenance media (MCF-7 and MDA-MB-231) or in reduced media (MCF-7). Twenty-four hours after plating, the media were replaced with maintenance (MCF-7 and MDA-MB-231) or reduced (MCF-7) media containing atrazine, simazine, or cyanazine at 0.1-, 1-, and 10-fold the EPA safe levels or DMSO control. Atrazine was added at 0.3, 3.0, or 30 ppb (𝜇g/L; 0.64–64 𝜇M), cyanazine was added at 0.1, 1.0, or 10 ppb (0.17–17 𝜇M), and simazine was added at 0.4, 4.0, or 40 ppb (0.92–92 𝜇M). After twenty-four hours, 3 𝜇g resazurin was added and allowed to incubate for three hours prior to reading absorbance at 570 and 595nm on iMark Microplate Absorbance Reader (Bio-Rad, Hercules, CA).We performed univariate analysis of variance (ANOVA) using SPSS

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:36:27 GMT 2025` Edited by `admin` on `Mon Mar 31 17:36:27 GMT 2025`
Record UNII	SG0C34SMY3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SIMAZINE

Common Name

English

NSC-25999

Preferred Name

English

SIMAZINE [HSDB]

Common Name

English

6-CHLORO-N,N'-DIETHYL-1,3,5-TRIAZINE-2,4-DIAMINE

Systematic Name

English

SIMAZINE [ISO]

Common Name

English

6-CHLORO-N(SUP 2),N(SUP 4)-DIETHYL-1,3,5-TRIAZINE-2,4-DIAMINE

Systematic Name

English

SIMAZINE [MI]

Common Name

English

SIMAZINE [IARC]

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

80807