Compounds > tembotrione
Page last updated: 2024-11-12

tembotrione

Description

tembotrione : An aromatic ketone that is 2-benzoylcyclohexane-1,3-dione in which the phenyl group is substituted at positions 2, 3, and 4 by chlorine, (2,2,2-trifluoroethoxy)methyl, and methylsulfonyl groups, respectively. It is a post-emergence herbicide used (particularly in conjunction with the herbicide safener cyprosulfamide) for the control of a wide range of broad-leaved and grassy weeds in corn and other crops. [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 CID11556911
CHEMBL ID2272077
CHEBI ID132273
SCHEMBL ID116424
MeSH IDM0590324

Synonyms (40)

Synonym
tembotrione
2-{2-chloro-4-mesyl-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl}cyclohexane-1,3-dione
2-{2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl}cyclohexane-1,3-dione
335104-84-2
2-[2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl]-1,3-cyclohexanedione
CHEBI:132273
2-{2-chloro-4-(methanesulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl}cyclohexane-1,3-dione
2-[2-chloro-4-methylsulfonyl-3-(2,2,2-trifluoroethoxymethyl)benzoyl]cyclohexane-1,3-dione
unii-wa5uz202ks
tembotrione [iso]
wa5uz202ks ,
hsdb 7881
cas-335104-84-2
dtxcid3027037
tox21_302382
dtxsid5047037 ,
NCGC00256145-01
263401-02-1
tembotrione [mi]
ae-0172747
2-(2-chloro-4-(methylsulfonyl)-3-((2,2,2-trifluoroethoxy)methyl)benzoyl)-1,3-cyclohexanedione
2-(2-chloro-4-mesyl-3-((2,2,2-trifluoroethoxy)methyl)benzoyl)cyclohexane-1,3-dione
2-cyclohexen-1-one, 2-(2-chloro-4-(methylsulfonyl)-3-((2,2,2-trifluoroethoxy)methyl)benzoyl)-3-hydroxy-
2-(2-chloro-4-(methylsulfonyl)-3-((2,2,2-trifluoroethoxy)methyl)benzoyl)-3-hydroxy-2-cyclohexen-1-one
SCHEMBL116424
CHEMBL2272077
2-{2-chloro-4-methanesulfonyl-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl}cyclohexane-1,3-dione
AKOS027269927
tembotrione, pestanal(r), analytical standard
2-(2-chloro-4-(methylsulfonyl)-3-((2,2,2-trifluoroethoxy)methyl)benzoyl)cyclohexane-1,3-dione
tembotrione 100 microg/ml in acetonitrile
mfcd11840613
Q2372037
AMY11225
bdbm50264336
W15593
A935465
AS-56908
CS-0142853
HY-137910

Research Excerpts

Overview

Tembotrione is a triketone group herbicide having worldwide applications for weed management in maize. It targets the 4-Hydroxyphenylpyruvate dioxygenase enzyme of weeds.

ExcerptReferenceRelevance
"Tembotrione (TBT) is a β-triketone herbicide targeting the 4-Hydroxyphenylpyruvate dioxygenase enzyme (4-HPPD) of weeds. "( "Structural responses of non-targeted bacterial and hppd communities to the herbicide tembotrione in soil".
Barthelmebs, L; Calvayrac, C; Devers, M; Martin-Laurent, F; Suzuki, M; Terol, H; Thiour-Mauprivez, C, 2024)		3.11
"Tembotrione is a rather novel pesticide, usually used for post-emergence weed control. "( Evaluation of oxidative stress responses and primary DNA damage in blood and brain of rats exposed to low levels of tembotrione.
Kašuba, V; Katić, A; Kopjar, N; Marjanović Čermak, AM; Micek, V; Milić, M; Pavičić, I; Pizent, A; Tariba Lovaković, B; Želježić, D; Žunec, S, 2020)		2.21
"Tembotrione is a triketone group herbicide having worldwide applications for weed management in maize. "( Ultimate fate of herbicide tembotrione and its metabolite TCMBA in soil.
Duhan, A; Rani, N; Tomar, D, 2020)		2.3
"Tembotrione is a triketone herbicide, usually used for post-emergence weed control in corn. "( Assessment of oxidative stress responses and the cytotoxic and genotoxic potential of the herbicide tembotrione in HepG2 cells.
Kašuba, V; Kopjar, N; Marjanović, AM; Milić, M; Pavičić, I; Pizent, A; Rozgaj, R; Tariba, B; Vrdoljak, AL; Želježić, D; Žunec, S, 2016)		2.09

Dosage Studied

ExcerptRelevanceReference
" Dose-response experiments indicated that the level of resistance to the HPPD inhibitor mesotrione is at least tenfold relative to sensitive biotypes."( Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States.
Hager, AG; Hausman, NE; Kaundun, SS; Polge, ND; Riechers, DE; Singh, S; Thomas, DA; Tranel, PJ, 2011)		0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
herbicideA substance used to destroy plant pests.
agrochemicalAn agrochemical is a substance that is used in agriculture or horticulture.
EC 1.13.11.27 (4-hydroxyphenylpyruvate dioxygenase) inhibitorAn EC 1.13.11.* (oxidoreductase acting on single donors and incorporating 2 atoms of oxygen) inhibitor that interferes with the activity of 4-hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27).
carotenoid biosynthesis inhibitorAny pathway inhibitor that acts on the carotenoid biosynthesis pathway.
[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 (7)

ClassDescription
sulfoneAn organosulfur compound having the structure RS(=O)2R (R =/= H).
cyclic ketone
aromatic ketoneA ketone in which the carbonyl group is attached to an aromatic ring.
monochlorobenzenesAny member of the class of chlorobenzenes containing a mono- or poly-substituted benzene ring in which only one substituent is chlorine.
organofluorine compoundAn organofluorine compound is a compound containing at least one carbon-fluorine bond.
etherAn organooxygen compound with formula ROR, where R is not hydrogen.
beta-triketoneA triketone in which the each ketone functionality is located beta- to the other two.
[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 (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
acetylcholinesteraseHomo sapiens (human)Potency29.98160.002541.796015,848.9004AID1347395; AID1347398
estrogen nuclear receptor alphaHomo sapiens (human)Potency27.52230.000229.305416,493.5996AID743069
[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)
4-hydroxyphenylpyruvate dioxygenaseArabidopsis thaliana (thale cress)Ki0.01300.01300.01300.0130AID1480422
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (1)

Processvia Protein(s)Taxonomy
tyrosine catabolic process4-hydroxyphenylpyruvate dioxygenaseArabidopsis thaliana (thale cress)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (1)

Processvia Protein(s)Taxonomy
4-hydroxyphenylpyruvate dioxygenase activity4-hydroxyphenylpyruvate dioxygenaseArabidopsis thaliana (thale cress)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID1104960Herbicidal activity against Amaranthus tuberculatus biotype MCR 12 assessed as visual injury at 92 g/ha applied as spray after 21 days under green house conditions relative to untreated control2011Pest management science, Mar, Volume: 67, Issue:3
Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States.
AID1104987Herbicidal activity against Amaranthus tuberculatus biotype MCR 15 assessed as visual injury at 92 g/ha applied as spray after 7 days under green house conditions relative to untreated control2011Pest management science, Mar, Volume: 67, Issue:3
Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States.
AID1104990Herbicidal activity against Amaranthus tuberculatus biotype MCR 12 assessed as visual injury at 92 g/ha applied as spray after 7 days under green house conditions relative to untreated control2011Pest management science, Mar, Volume: 67, Issue:3
Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States.
AID1104976Herbicidal activity against Amaranthus tuberculatus biotype MCR 12 assessed as visual injury at 92 g/ha applied as spray after 14 days under green house conditions relative to untreated control2011Pest management science, Mar, Volume: 67, Issue:3
Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States.
AID1480422Inhibition of Arabidopsis thaliana HPPD expressed in Escherichia coli JM109 using HPPA as substrate after 10 mins2017Journal of medicinal chemistry, 05-25, Volume: 60, Issue:10
4-Hydroxyphenylpyruvate Dioxygenase and Its Inhibition in Plants and Animals: Small Molecules as Herbicides and Agents for the Treatment of Human Inherited Diseases.
AID1104969Herbicidal activity against Amaranthus tuberculatus biotype MCR 16 assessed as visual injury at 92 g/ha applied as spray after 14 days under green house conditions relative to untreated control2011Pest management science, Mar, Volume: 67, Issue:3
Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States.
AID1104978Herbicidal activity against Amaranthus tuberculatus biotype ACR assessed as visual injury at 92 g/ha applied as spray after 14 days under green house conditions relative to untreated control2011Pest management science, Mar, Volume: 67, Issue:3
Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States.
AID1104996Herbicidal activity against Amaranthus tuberculatus biotype WCS assessed as visual injury at 92 g/ha applied as spray after 7 days under green house conditions relative to untreated control2011Pest management science, Mar, Volume: 67, Issue:3
Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States.
AID1104963Herbicidal activity against Amaranthus tuberculatus biotype ACR assessed as visual injury at 92 g/ha applied as spray after 21 days under green house conditions relative to untreated control2011Pest management science, Mar, Volume: 67, Issue:3
Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States.
AID1104972Herbicidal activity against Amaranthus tuberculatus biotype MCR 15 assessed as visual injury at 92 g/ha applied as spray after 14 days under green house conditions relative to untreated control2011Pest management science, Mar, Volume: 67, Issue:3
Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States.
AID1104954Herbicidal activity against Amaranthus tuberculatus biotype MCR 16 assessed as visual injury at 92 g/ha applied as spray after 21 days under green house conditions relative to untreated control2011Pest management science, Mar, Volume: 67, Issue:3
Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States.
AID1104993Herbicidal activity against Amaranthus tuberculatus biotype ACR assessed as visual injury at 92 g/ha applied as spray after 7 days under green house conditions relative to untreated control2011Pest management science, Mar, Volume: 67, Issue:3
Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States.
AID1104981Herbicidal activity against Amaranthus tuberculatus biotype WCS assessed as visual injury at 92 g/ha applied as spray after 14 days under green house conditions relative to untreated control2011Pest management science, Mar, Volume: 67, Issue:3
Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States.
AID1104957Herbicidal activity against Amaranthus tuberculatus biotype MCR 15 assessed as visual injury at 92 g/ha applied as spray after 21 days under green house conditions relative to untreated control2011Pest management science, Mar, Volume: 67, Issue:3
Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States.
AID1104984Herbicidal activity against Amaranthus tuberculatus biotype MCR 16 assessed as visual injury at 92 g/ha applied as spray after 7 days under green house conditions relative to untreated control2011Pest management science, Mar, Volume: 67, Issue:3
Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States.
AID1104966Herbicidal activity against Amaranthus tuberculatus biotype WCS assessed as visual injury at 92 g/ha applied as spray after 21 days under green house conditions relative to untreated control2011Pest management science, Mar, Volume: 67, Issue:3
Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (22)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's10 (45.45)24.3611
2020's12 (54.55)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 40.95

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index40.95 (24.57)
Research Supply Index3.14 (2.92)
Research Growth Index4.65 (4.65)
Search Engine Demand Index77.01 (26.88)
Search Engine Supply Index2.74 (0.95)

This Compound (40.95)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (13.64%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other19 (86.36%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
benzoic acid
Benzoic Acid: A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.. benzoic acid : A compound comprising a benzene ring core carrying a carboxylic acid substituent.. aromatic carboxylic acid : Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.		2.0810benzoic acidsalgal metabolite;
antimicrobial food preservative;
drug allergen;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
EC 3.1.1.3 (triacylglycerol lipase) inhibitor;
human xenobiotic metabolite;
plant metabolite
atrazine
[no description available]		7.8330chloro-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.		2.1310titanium group element atom
hypochlorous acid
Hypochlorous Acid: An oxyacid of chlorine (HClO) containing monovalent chlorine that acts as an oxidizing or reducing agent.. hypochlorous acid : A chlorine oxoacid with formula HOCl; a weak, unstable acid, it is the active form of chlorine in water.		2.1110chlorine oxoacid;
reactive oxygen species		EC 2.5.1.18 (glutathione transferase) inhibitor;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
human metabolite
potassium persulfate
[no description available]		2.1310
chlorine
Chlorine: An element with atomic symbol Cl, atomic number 17, and atomic weight 35, and member of the halogen family.		2.1110diatomic chlorine;
gas molecular entity		bleaching agent
titanium dioxide
titanium dioxide: used medically as protectant against externally caused irritation & sunlight; high concentrations of dust may cause irritation to respiratory tract; RN given refers to titanium oxide (TiO2); structure. titanium dioxide : A titanium oxide with the formula TiO2. A naturally occurring oxide sourced from ilmenite, rutile and anatase, it has a wide range of applications.		2.1310titanium oxidesfood colouring
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.		5.92160
pinocembrin
pinocembrin : A dihydroxyflavanone in which the two hydroxy groups are located at positions 5 and 7. A natural product found in Piper sarmentosum and Cryptocarya chartacea.		3.2510(2S)-flavan-4-one;
dihydroxyflavanone		antineoplastic agent;
antioxidant;
metabolite;
neuroprotective agent;
vasodilator agent
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.		10.0460aromatic ketone;
beta-triketone;
cyclohexanones;
sulfone		carotenoid biosynthesis inhibitor;
environmental contaminant;
herbicide;
xenobiotic
nitisinone
[no description available]		3.2510(trifluoromethyl)benzenes;
C-nitro compound;
cyclohexanones;
mesotrione		EC 1.13.11.27 (4-hydroxyphenylpyruvate dioxygenase) inhibitor
mesotrione
mesotrione: brandname is after the Callistemon (MYRTACEAE) plant it was found in; structure in first source. mesotrione : An aromatic ketone that is cyclohexa-1,3-dione in which one of the hydrogens at position 2 is substituted by a 4-(methanesulfonyl)-2-nitrobenzoyl group.		5.0460aromatic ketone;
beta-triketone;
C-nitro compound;
sulfone		carotenoid biosynthesis inhibitor;
EC 1.13.11.27 (4-hydroxyphenylpyruvate dioxygenase) inhibitor;
environmental contaminant;
herbicide;
xenobiotic
(+)-usnic acid
[no description available]		3.2510usnic acid
leptospermone
leptospermone: a beta-triketone phloroglucinol derivative and constituent of essential oil extracted from Leptospermum scoparium (manuka oil); structure in first source		3.2510
topramezone
topramezone: corn herbicide, an inhibitor of 4-hydroxyphenylpyruvate dioxygenase; structure in first source. topramezone : An aromatic ketone that is phenyl 1H-pyrazol-4-yl ketone in which the pyrazolyl group is substituted at positions 1 and 5 by methyl and hydroxy groups, respectively, and in which the phenyl group is substituted at positions 2, 3, and 4 by methyl, 4,5-dihydro-1,2-oxazol-3-yl, and methylsulfonyl groups, respectively. A potent inhibitor of 4-hydroxyphenylpyruvate dioxygenase (HPPD) that is rapily metabolised by corn to non-active substances, it is used as a herbicide for the treatment of broadleaf weeds.		3.9130
alpha(-(cyclopropylcarbonyl)-2-(methyvlsulfonyl)-beta-oxo-4-(trifluromethyl)benzenepropanenitrile)
diketonitrile: structure in first source. 2-cyano-3-cyclopropyl-1-(2-mesyl-4-trifluoromethylphenyl)propan-1,3-dione : A beta-diketone and nitrile resulting from the the degradation of the isoxazole ring of isoxaflutole. The active herbicide of the proherbicide isoxaflutole.		3.2510(trifluoromethyl)benzenes;
aromatic ketone;
beta-diketone;
cyclopropanes;
nitrile;
sulfone		agrochemical;
EC 1.13.11.27 (4-hydroxyphenylpyruvate dioxygenase) inhibitor;
herbicide
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.		2.610chlorophyll;
methyl ester		cofactor
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.		2.2510
ConditionIndicatedRelationship StrengthStudiesTrials
4 Hydroxyphenylpyruvate Dioxygenase Deficiency Disease
[description not available]		03.0610
Alcaptonuria
[description not available]		03.0610
Alkaptonuria
An inborn error of amino acid metabolism resulting from a defect in the enzyme HOMOGENTISATE 1,2-DIOXYGENASE, an enzyme involved in the breakdown of PHENYLALANINE and TYROSINE. It is characterized by accumulation of HOMOGENTISIC ACID in the urine, OCHRONOSIS in various tissues, and ARTHRITIS.		03.0610
Tyrosinemias
A group of disorders which have in common elevations of tyrosine in the blood and urine secondary to an enzyme deficiency. Type I tyrosinemia features episodic weakness, self-mutilation, hepatic necrosis, renal tubular injury, and seizures and is caused by a deficiency of the enzyme fumarylacetoacetase. Type II tyrosinemia features INTELLECTUAL DISABILITY, painful corneal ulcers, and keratoses of the palms and plantar surfaces and is caused by a deficiency of the enzyme TYROSINE TRANSAMINASE. Type III tyrosinemia features INTELLECTUAL DISABILITY and is caused by a deficiency of the enzyme 4-HYDROXYPHENYLPYRUVATE DIOXYGENASE. (Menkes, Textbook of Child Neurology, 5th ed, pp42-3)		03.0610
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		02.3110
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