Page last updated: 2024-11-06

hexazinone

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Hexazinone is a triazine herbicide that is used to control broadleaf weeds in a variety of crops, including soybeans, corn, and cotton. It is a selective herbicide, meaning that it kills weeds without harming the crop plants. Hexazinone is absorbed by the roots and leaves of plants and inhibits photosynthesis. It is also a systemic herbicide, meaning that it is translocated throughout the plant. The synthesis of hexazinone involves a multi-step process that begins with the reaction of cyanuric chloride with an amine. The resulting product is then reacted with a substituted phenylurea, which gives hexazinone. Studies have shown that hexazinone can have both positive and negative effects on the environment. It is toxic to fish and aquatic invertebrates, and it can persist in the soil for several months. However, it is also effective at controlling weeds and reducing the need for other herbicides. As a result, it is important to use hexazinone in a responsible manner to minimize its negative impacts on the environment. Hexazinone is studied to better understand its environmental effects and to develop more effective and environmentally friendly herbicides. This research is essential to ensuring the sustainable use of herbicides and protecting the environment.'

hexazinone: RN given refers to parent cpd; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID39965
CHEMBL ID2252598
CHEBI ID5705
SCHEMBL ID66377
MeSH IDM0085235

Synonyms (65)

Synonym
AC-16229
1,3,5-triazine-2,4(1h,3h)-dione, 3-cyclohexyl-6-(dimethylamino)-1-methyl-
3-cyclohexyl-1-methyl-6-(dimethylamino)-s-trazine-2,4(1h,3h)-dione
51235-04-2
hexazinone
NCGC00164460-01
hsdb 6670
velpar weed killer
brushkiller
caswell no. 271aa
velpar l
3-cyclohexyl-6-(dimethylamino)-1-methyl-s-triazine-2,4(1h,3h)-dione
hexazinone [ansi:bsi:iso]
s-triazine-2,4(1h,3h)-dione, 3-cyclohexyl-6-(dimethylamino)-1-methyl-
gridball
epa pesticide chemical code 107201
velpar
brn 0618801
einecs 257-074-4
ccris 5273
3-cyclohexyl-6-dimethylamino-1-methyl-1,2,3,4-tetrahydro-1,3,5-triazine-2,4-dione
sha 107201
dpx 3674
3-cyclohexyl-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1h,3h)-dione
NCGC00168317-01
3-cyclohexyl-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4-dione
NCGC00168317-03
NCGC00168317-02
cas-51235-04-2
tox21_300745
NCGC00254651-01
dtxsid4024145 ,
NCGC00259214-01
dtxcid804145
tox21_201665
A828499
unii-y51727mr1y
y51727mr1y ,
5-26-10-00171 (beilstein handbook reference)
FT-0630643
AKOS015914992
chebi:5705 ,
CHEMBL2252598
3-cyclohexyl-6-dimethylamino-1-methyl-1,3,5-triazine-2,4(1h,3h)-dione
dpx-3674
hexazinone [hsdb]
hexazinone [mi]
hexazinone [iso]
SCHEMBL66377
1-methyl-3-cyclohexyl-6-dimethylamino-s-triazine-2,4(1h,3h)-dione
H1686
hexazinon
3-cyclohexy-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1h,3h)-dione
hexazinoe
hexazinone, pestanal(r), analytical standard
bdbm50487023
hexazinone 100 microg/ml in acetonitrile
hexazinone 10 microg/ml in acetonitrile
Q408234
A12586
CS-0013917
HY-B1849
hexazinone 1000 microg/ml in toluene
BS-32507
hexazinone-d6 (n,n-dimethyl-d6-amino)

Research Excerpts

Overview

Hexazinone is a post-emergence herbicide/arboricides. Its acute poisoning has rarely been reported. It is widely used in sugarcane cultivation and has a potential to contaminate water resources.

ExcerptReferenceRelevance
"Hexazinone is a post-emergence herbicide/arboricides, and its acute poisoning has rarely been reported. "( [A case of acute poisoning caused by oral administration of large dose hexazinone].
Lin, L; Song, W; Zhan, F; Zhang, J, 2022
)
2.4
"Hexazinone is an herbicide widely used in sugarcane cultivation and has a potential to contaminate water resources."( Sensitivity of the macrophytes Pistia stratiotes and Eichhornia crassipes to hexazinone and dissipation of this pesticide in aquatic ecosystems.
Alencar, BTB; da Costa, VAM; Dos Santos, JB; Dos Santos, NMC; Francino, DMT; Ribeiro, VHV; Silva, DV; Souza, MF, 2019
)
1.46
"Hexazinone is a moderate to severe eye irritant in the rabbit and produced only mild erythema in rabbit skin at 5278 mg/kg, a dose which did not produce lethality or other clinical signs."( Acute and environmental toxicity studies with hexazinone.
Kennedy, GL, 1984
)
1.25

Effects

ExcerptReferenceRelevance
"Hexazinone has been detected at levels ranging from 0.2 to 50 micrograms/L in many groundwater samples from eastern Maine over the past decade. "( Determination of hexazinone in groundwater by direct-injection high-performance liquid chromatography.
Bushway, RJ; Katz, LE; Perkins, LB,
)
1.91

Toxicity

ExcerptReferenceRelevance
" The material is slightly to moderately toxic when given as a single oral dose; its LD50 in male rats is 1690 mg/kg, in male guinea pigs 860 mg/kg, and in male dogs greater than 3400 mg/kg although in the dog emesis prevented accurate quantitation."( Acute and environmental toxicity studies with hexazinone.
Kennedy, GL, 1984
)
0.53
" Ninety-day feeding of up to 1000 ppm produced no signs of a toxic response in rats."( Chronic toxicity, reproductive, and teratogenic studies of hexazinone.
Kaplan, AM; Kennedy, GL, 1984
)
0.51

Dosage Studied

ExcerptRelevanceReference
" Here we developed and applied a new protocol allowing dose-response assessment of four samples within 2 h (8 dilutions in duplicate)."( Rapid exposure assessment of PSII herbicides in surface water using a novel chlorophyll a fluorescence imaging assay.
Bengtson Nash, SM; Escher, BI; Mueller, JF; Muller, R; Quayle, P; Schreiber, U, 2008
)
0.35
" The dose-response curves (DRCs) between the observed inhibition toxicities and the doses of the pesticides or the mixtures were modeled by using the nonlinear least square fitting."( Combined photobacterium toxicity of herbicide mixtures containing one insecticide.
Liu, HL; Liu, SS; Song, XQ; Zhang, J; Zhang, YH, 2009
)
0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
1,3,5-triazinesAny compound with a 1,3,5-triazine skeleton, in which nitrogen atoms replace carbon at positions 1, 3 and 5 of the core benzene ring structure.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (7)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
GLI family zinc finger 3Homo sapiens (human)Potency45.62880.000714.592883.7951AID1259368; AID1259369
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency65.00490.003041.611522,387.1992AID1159555
retinoid X nuclear receptor alphaHomo sapiens (human)Potency46.20450.000817.505159.3239AID1159531
pregnane X nuclear receptorHomo sapiens (human)Potency65.00490.005428.02631,258.9301AID1346982
Caspase-7Cricetulus griseus (Chinese hamster)Potency32.57960.006723.496068.5896AID1346980
caspase-3Cricetulus griseus (Chinese hamster)Potency32.57960.006723.496068.5896AID1346980
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Photosystem II protein D1Spinacia oleracea (spinach)IC50 (µMol)0.10990.06500.48491.9000AID1090208
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID1090208Inhibition of photosynthetic electron transport at the PSII level in intact chloroplasts from Spinacia oleracea (spinach) leaves assessed as inhibition of in vitro activity by Hill reaction assay2005Journal of agricultural and food chemistry, May-18, Volume: 53, Issue:10
Pyrazole derivatives as photosynthetic electron transport inhibitors: new leads and structure-activity relationship.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (69)

TimeframeStudies, This Drug (%)All Drugs %
pre-19908 (11.59)18.7374
1990's9 (13.04)18.2507
2000's25 (36.23)29.6817
2010's23 (33.33)24.3611
2020's4 (5.80)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 31.54

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index31.54 (24.57)
Research Supply Index4.34 (2.92)
Research Growth Index4.78 (4.65)
Search Engine Demand Index79.74 (26.88)
Search Engine Supply Index3.99 (0.95)

This Compound (31.54)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies1 (1.32%)4.05%
Observational0 (0.00%)0.25%
Other75 (98.68%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]