Compounds > metamitron
Page last updated: 2024-12-06

metamitron

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

Description

metamitron : A member of the class of 1,2,4-triazines that is 1,2,4-triazin-5(4H)-one substituted by an amino group at position 4, a methyl group at position 3 and a phenyl group at position 6. [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]

Cross-References

ID SourceID
PubMed CID38854
CHEMBL ID3187145
CHEBI ID6791
SCHEMBL ID66369
MeSH IDM0137769

Synonyms (58)

Synonym
BIDD:ER0471
as-triazin-5(4h)-one, 4-amino-3-methyl-6-phenyl-
1,2,4-triazin-5(4h)-one, 4-amino-3-methyl-6-phenyl-
41394-05-2
goltix
metamitron
4-amino-3-methyl-6-phenyl-1,2,4-triazin-5-one, 97%
methiamitron [french]
metamitron [german]
4-amino-4,5-dihydro-3-methyl-6-phenyl-1,2,4-triazin-5-one
4-amino-3-methyl-6-phenyl-1,2,4-triazin-5(4h)-one
brn 0613129
metamitrone [iso-french]
metamiton
metamitron [bsi:iso]
bay-drw 1139
methiamitron [belgium]
herbrak
einecs 255-349-3
drw 1139
3-methyl-4-amino-6-phenyl-1,2,4-triazin(4h)-on [german]
4-amino-3-methyl-6-phenyl-1,2,4-triazin-5-one
3-methyl-4-amino-6-phenyl-1,2,4-triazin-5(4h)-one
dtxcid5027568
tox21_302665
dtxsid7047568 ,
cas-41394-05-2
NCGC00256694-01
A825543
4-azanyl-3-methyl-6-phenyl-1,2,4-triazin-5-one
h69rgo1qo6 ,
5-26-04-00395 (beilstein handbook reference)
unii-h69rgo1qo6
metamitrone
3-methyl-4-amino-6-phenyl-1,2,4-triazin(4h)-on
methiamitron
FT-0630619
AKOS015905026
metamitron [mi]
metamitron [iso]
SCHEMBL66369
3-methyl-4-amino-6-phenyl-1,2,4-triazin-5-one
4-amino-3-methyl-6-phenyl-1,2,4-triazin-5-(4h)-one
CHEBI:6791 ,
3-methyl-4-amino-6-phenyl-1,2,4-triazin(4h)-one
CHEMBL3187145
M2388
STL451248
4-amino-3-methyl-6-phenyl-4,5-dihydro-1,2,4-triazin-5-one
metamitron, pestanal(r), analytical standard
metamitron 10 microg/ml in acetonitrile
metamitron 100 microg/ml in acetonitrile
F21304
mfcd00055524
Q2293747
AS-13452
CS-W015509
HY-W014793

Research Excerpts

Overview

Metamitron (MTM) is a typical and widely used triazine herbicide. It is used in low rate weed control programs in sugar beet.

ExcerptReferenceRelevance
"Metamitron (MTM) is a typical and widely used triazine herbicide in agricultural production. "( Selection and colorimetric application of ssDNA aptamers against metamitron based on magnetic bead-SELEX.
Huang, W; Shen, G; Wang, L; Xie, X; Yu, H, 2022)		2.4
"Metamitron is a key herbicide in modern low rate weed control programs in sugar beet. "( Resistance to metamitron in Chenopodium album from sugar beet. a tale of the (un)expected?
Bulcke, R; Maeghe, L; Mechant, E, 2005)		2.13

Effects

ExcerptReferenceRelevance
"Metamitron has shown a good efficacy in the thinning of apple fruits."( EFFICACY OF METAMITRON IN APPLE THINNING IN SERBIA.
Aleksic, G; Andjelkovic, A; Dolovac, N; Gavrilovic, V; Marisavljevic, D; Radivojevic, L; Stevanovic, M, 2015)		1.52

Dosage Studied

ExcerptRelevanceReference
" Even though Goltix and Oleo were used at a higher dosage (10 times higher), the application of Goltix resulted in smaller effects and the additive Oleo was the least-active compound, with minor stimulation of test parameters at later observation times."( Monitoring impact of a pesticide treatment on bacterial soil communities by metabolic and genetic fingerprinting in addition to conventional testing procedures.
Backhaus, H; Engelen, B; Heuer, H; Malkomes, HP; Meinken, K; von Wintzingerode, F, 1998)		0.3
"In two independent dose-response greenhouse trials, there was a positive correlation between the strength of the stimulatory response during parental preconditioning and the magnitude of transgenerational changes in herbicide sensitivity and hormesis expression."( Low herbicide doses can change the responses of weeds to subsequent treatments in the next generation: metamitron exposed PSII-target-site resistant Chenopodium album as a case study.
Belz, RG, 2020)		0.77
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
environmental contaminantAny minor or unwanted substance introduced into the environment that can have undesired effects.
xenobioticA 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.
herbicideA substance used to destroy plant pests.
[role 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]

Drug Classes (1)

ClassDescription
1,2,4-triazinesAny compound with a 1,2,4-triazine skeleton, in which nitrogen atoms replace carbon at positions 1, 2 and 4 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 (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency54.84420.003041.611522,387.1992AID1159552; AID1159555
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency61.13060.001530.607315,848.9004AID1259401
farnesoid X nuclear receptorHomo sapiens (human)Potency21.87510.375827.485161.6524AID743220
estrogen nuclear receptor alphaHomo sapiens (human)Potency46.69380.000229.305416,493.5996AID743075; AID743079
aryl hydrocarbon receptorHomo sapiens (human)Potency40.23090.000723.06741,258.9301AID743085; AID743122
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (41)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (4.88)18.7374
1990's3 (7.32)18.2507
2000's17 (41.46)29.6817
2010's16 (39.02)24.3611
2020's3 (7.32)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 33.43

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 Index33.43 (24.57)
Research Supply Index3.74 (2.92)
Research Growth Index5.25 (4.65)
Search Engine Demand Index65.76 (26.88)
Search Engine Supply Index3.00 (0.95)

This Compound (33.43)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other41 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
ammonium hydroxide
azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.		1.9610azane;
gas molecular entity;
mononuclear parent hydride		EC 3.5.1.4 (amidase) inhibitor;
metabolite;
mouse metabolite;
neurotoxin;
NMR chemical shift reference compound;
nucleophilic reagent;
refrigerant
bromide
Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)		2.0510halide anion;
monoatomic bromine
carbamates
[no description available]		2.4320amino-acid anion
glycine
[no description available]		2.4320alpha-amino acid;
amino acid zwitterion;
proteinogenic amino acid;
serine family amino acid		EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor;
fundamental metabolite;
hepatoprotective agent;
micronutrient;
neurotransmitter;
NMDA receptor agonist;
nutraceutical
nitrates
Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.		1.9610monovalent inorganic anion;
nitrogen oxoanion;
reactive nitrogen species
nitrites
Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)		1.9610monovalent inorganic anion;
nitrogen oxoanion;
reactive nitrogen species		human metabolite
pyruvic acid
Pyruvic Acid: An intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed). pyruvic acid : A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis.		1.98102-oxo monocarboxylic acidcofactor;
fundamental metabolite
succinic acid
Succinic Acid: A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851). succinic acid : An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.		1.9810alpha,omega-dicarboxylic acid;
C4-dicarboxylic acid		anti-ulcer drug;
fundamental metabolite;
micronutrient;
nutraceutical;
radiation protective agent
1-aminobenzotriazole
[no description available]		2.0710
acetochlor
acetochlor : A monocarboxylic acid amide that is N-phenylacetamide carrying an ethyl and a methyl group at positions 2 and 6 respectively on the benzene ring while one of the methyl hydrogens as well as the hydrogen attached to the nitrogen atom have been replaced by a chloro and an ethoxymethyl group respectively.		2.0310aromatic amide;
monocarboxylic acid amide;
organochlorine compound		environmental contaminant;
herbicide;
xenobiotic
atrazine
[no description available]		3.2860chloro-1,3,5-triazine;
diamino-1,3,5-triazine		environmental contaminant;
herbicide;
xenobiotic
bentazone
bentazone: RN given refers to parent cpd; structure. bentazone : A benzothiadiazine that is 1H-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide substituted by an isopropyl group at position 3.		2.4620benzothiadiazineenvironmental contaminant;
herbicide;
xenobiotic
metolachlor
metolachlor: structure given in first source. metolachlor : A racemate that consists of equimolar amounts of (R)- and (S)-metolachlor.. 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide : An organochlorine compound that is 2-chloroacetamide substituted by a (2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl) group at the nitrogen atom.		2.0310aromatic amide;
benzenes;
ether;
organochlorine compound
trifluralin
Trifluralin: A microtubule-disrupting pre-emergence herbicide.. trifluralin : A substituted aniline that is N,N-dipropylaniline substituted by a nitro groups at positions 2 and 6 and a trifluoromethyl group at position 4. It is an agrochemical used as a pre-emergence herbicide.		2.0210(trifluoromethyl)benzenes;
C-nitro compound;
substituted aniline		agrochemical;
environmental contaminant;
herbicide;
xenobiotic
piperonyl butoxide
[no description available]		2.0710benzodioxolespesticide synergist
alanine
Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.		2.4620alanine zwitterion;
alanine;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid		EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor;
fundamental metabolite
linuron
Linuron: A selective pre- and post-emergence herbicide. (From Merck Index, 11th ed). linuron : A member of the class of phenylureas that is N-methyl urea substituted by a methoxy group at position 1 and a 3,4-dichlorophenyl group at position 3.		2.4620dichlorobenzene;
phenylureas		agrochemical;
environmental contaminant;
herbicide;
xenobiotic
dinoterb
[no description available]		1.9910C-nitro compound;
phenols
terbutylazine
terbutylazine : A diamino-1,3,5-triazine that is N-tert-butyl-N'-methyl-1,3,5-triazine-2,4-diamine substituted by a chloro group at position 6.		2.0510chloro-1,3,5-triazine;
diamino-1,3,5-triazine		environmental contaminant;
herbicide;
xenobiotic
titanium
Titanium: A dark-gray, metallic element of widespread distribution but occurring in small amounts with atomic number, 22, atomic weight, 47.867 and symbol, Ti; specific gravity, 4.5; used for fixation of fractures.		2.2110titanium group element atom
cerium
Cerium: An element of the rare earth family of metals. It has the atomic symbol Ce, atomic number 58, and atomic weight 140.12. Cerium is a malleable metal used in industrial applications.		2.2110f-block element atom;
lanthanoid atom
gold
Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.		2.4110copper group element atom;
elemental gold
phenmedipham
phenmedipham: minor descriptor (72-84); on-line search CARBAMATES (72-84); Index Medicus search HERBICIDES, CARBAMATE (75-84), CARBAMATES (72-75). phenmedipham : A carbamate ester that is (3-methylphenyl)carbamic acid in which the hydrogen of the hydroxy group has been replaced by a 3-[(methoxycarbonyl)amino]phenyl group.		7.4320carbamate esterenvironmental contaminant;
herbicide;
xenobiotic
tiletamine hydrochloride
Cyclohexanones: Cyclohexane ring substituted by one or more ketones in any position.. cyclohexanones : Any alicyclic ketone based on a cyclohexane skeleton and its substituted derivatives thereof.		2.0210
methabenzthiazuron
[no description available]		1.9710benzothiazoles
metribuzin
metribuzin : A member of the class of 1,2,4-triazines that is 1,2,4-triazin-5(4H)-one substituted by an amino group at position 4, tert-butyl group at position 6 and a methylsulfanyl group at position 3.		8.11501,2,4-triazines;
cyclic ketone;
organic sulfide		agrochemical;
environmental contaminant;
herbicide;
xenobiotic
ethofumesate
ethofumesate: structure in first source. ethofumesate : A racemate comprising of equimolar amounts of (S)- and (R)-ethofumesate.. 2-ethoxy-3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl methanesulfonate : A methanesulfonate ester that is methanesulfonic acid in which the hydrogen of the hydroxy group has been replaced by a 2-ethoxy-3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl group.		7.43201-benzofurans;
ether;
methanesulfonate ester
isoproturon
isoproturon : A member of the class of phenylureas that is 1,1-dimethylurea substituted by a p-cumenyl group at position 3. A selective, systemic herbicide used to control annual grasses and broadleaf weeds in cereals, its use within the EU has been banned after September 2017 on the grounds of potential groundwater contamination and risks to aquatic life; there have also been concerns about its endocrine-disrupting properties.		3.13503-(3,4-substituted-phenyl)-1,1-dimethylureaagrochemical;
environmental contaminant;
herbicide;
xenobiotic
metalaxyl
metalaxyl: RN given refers to (DL-Ala)-isomer. metalaxyl : A racemate comprising equal amounts of (R)- and (S)-metalaxyl. A systemic fungicide, it is active against phytopathogens of the order Peronosporales and is used to conrtrol Pythium in a number of vegetable crops.. methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate : An alanine derivative that is methyl alaninate in which one of the hydrogens attached to the nitrogen is substituted by a methoxyacetyl group, while the other is substituted by a 2,6-dimethylphenyl group.		2.4620alanine derivative;
aromatic amide;
carboxamide;
ether;
methyl ester
triazoles
Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.		2.07101,2,3-triazole
1,2,4-triazine
[no description available]		2.13101,2,4-triazines;
triazine
ceric oxide
ceric oxide: RN given refers to cpd with MF CeO2. ceric oxide : A metal oxide with formula CeO2. It is used for polishing glass, in coatings for infra-red filters to prevent reflection, and as an oxidant and catalyst in organic synthesis.		2.2110cerium molecular entity;
metal oxide
dimethenamid
dimethenamid: structure in first source. dimethenamid : A racemate composed of equimolar amounts of (R)- and (S)-dimethenamid. A herbicide, it is applied to the soil for the control of various broad-leaved weeds and grasses. Only the S enantiomer (generally known as dimethenamid-P) is active.. 2-chloro-N-(2,4-dimethylthiophen-3-yl)-N-(1-methoxypropan-2-yl)acetamide : An organochlorine compound that is 2-chloroacetamide substituted by a 2,4-dimethylthiophen-3-yl and a 1-methoxypropan-2-yl group at the nitrogen atom.		2.0310aromatic amide;
ether;
organochlorine compound;
thiophenes
sulcotrione
sulcotrione: a bleaching herbicide. sulcotrione : An aromatic ketone that is cyclohexane-1,3-dione substituted by a 2-chloro-4-(methylsulfonyl)benzoyl group at position 2.		2.0210aromatic ketone;
beta-triketone;
cyclohexanones;
sulfone		carotenoid biosynthesis inhibitor;
environmental contaminant;
herbicide;
xenobiotic
benzofurans
Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.		2.4320
lead
Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.		7.2110carbon group element atom;
elemental lead;
metal atom		neurotoxin
ribose
ribopyranose : The pyranose form of ribose.		1.9810D-ribose;
ribopyranose
chlorophyll a
Chlorophyll: Porphyrin derivatives containing magnesium that act to convert light energy in photosynthetic organisms.. chlorophyll : A family of magnesium porphyrins, defined by the presence of a fifth ring beyond the four pyrrole-like rings. The rings can have various side chains which usually include a long phytol chain.		2.7330chlorophyll;
methyl ester		cofactor
phosphinothricin
phosphinothricin: RN given refers to parent cpd with unspecified isomeric designation; structure. phosphinothricin(1-) : Conjugate base of phosphinothricin arising from deprotonation of the phosphinate function.		2.4320organic anion
clay
Clay: A naturally-occurring rock or soil constituent characterized by particles with a diameter of less than 0.005 mm. It is composed primarily of hydrous aluminum silicates, trace amounts of metal OXIDES, and organic matter.		2.0210
ConditionIndicatedRelationship StrengthStudiesTrials
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.4320