Compounds > isoxaflutole
Page last updated: 2024-12-07

isoxaflutole

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

Description

Isoxaflutole is a pre-emergent herbicide used to control broadleaf weeds in various crops, including corn, soybeans, and cotton. It is a member of the isoxazole chemical class. Its synthesis involves multiple steps, starting with the reaction of 2-chloro-5-trifluoromethylpyridine with 3-hydroxy-2-butanone, followed by cyclization and oxidation. Isoxaflutole inhibits the enzyme 4-hydroxyphenylpyruvate dioxygenase (HPPD), which is crucial for carotenoid biosynthesis in plants. By inhibiting HPPD, isoxaflutole disrupts the production of carotenoids, leading to bleaching and death of susceptible weeds. Isoxaflutole is studied due to its selective herbicidal activity, which allows it to control weeds while being safe for the target crop. Extensive research is conducted to understand its mode of action, environmental fate, and potential for resistance development. '

isoxaflutole: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

isoxaflutole : A member of the class of isoxazoles that is 1,2-oxazole substituted by a 2-(methanesulfonyl)-4-(trifluoromethyl)benzoyl group and a cyclopropyl group at positions 4 and 5, respectively. It is a 4-hydroxyphenylpyruvate dioxygenase inhibitor which is used as a herbicide for weed control in maize and sugarcane. [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 CID84098
CHEMBL ID1887147
CHEBI ID141213
SCHEMBL ID66989
MeSH IDM0372201

Synonyms (61)

Synonym
NCGC00164004-01
(5-cyclopropylisoxazol-4-yl)[2-(methylsulfonyl)-4-(trifluoromethyl)phenyl]methanone
141112-29-0
isoxaflutole
NCGC00164004-02
balance
(5-cyclopropyl-4-isoxazolyl)[2-(methylsulfonyl)-4-(trifluoromethyl)phenyl]methanone
merlin
rp 201772
CHEBI:141213
(5-cyclopropyl-1,2-oxazol-4-yl)[2-(methylsulfonyl)-4-(trifluoromethyl)phenyl]methanone
5-cyclopropyl-1,2-oxazol-4-yl alpha,alpha,alpha-trifluoro-2-mesyl-p-tolyl ketone
(5-cyclopropyl-1,2-oxazol-4-yl)(alpha,alpha,alpha-trifluoro-2-mesyl-p-tolyl)methanone
rpa 201772
(5-cyclopropylisoxazol-4-yl)(alpha,alpha,alpha-trifluoro-2-mesyl-p-tolyl)methanone
5-cyclopropyl-4-[2-methanesulfonyl-4-(trifluoromethyl)benzoyl]-1,2-oxazole
exp 31130a
(5-cyclopropyl-1,2-oxazol-4-yl)-[2-methylsulfonyl-4-(trifluoromethyl)phenyl]methanone
NCGC00164004-03
methanone, (5-cyclopropyl-4-isoxazolyl)(2-(methylsulfonyl)-4-(trifluoromethyl)phenyl)-
unii-0t9r0o0eyt
einecs annex i index 606-054-00-7
ift cpd
0t9r0o0eyt ,
(5-cyclopropyl-4-isoxazolyl)(2-(methylsulfonyl)-4-(trifluoromethyl)phenyl)methanone
isoxaflutole [iso]
hsdb 7275
NCGC00254825-01
dtxcid3014723
dtxsid5034723 ,
tox21_300923
cas-141112-29-0
rpa-201772
isoxaflutole [hsdb]
5-cyclopropylisoxazol-4-yl 2-mesyl-4-trifluoromethylphenyl ketone
(5-cyclopropyl-1,2-oxazol-4-yl)(.alpha.,.alpha.,.alpha.-trifluoro-2-mesyl-p-tolyl)methanone
isoxaflutole [mi]
5-cyclopropyl-4-(2-methanesulfonyl-4-trifluoromethylbenzoyl)isoxazole
264-eup-99
AKOS015904028
(5-cyclopropylisoxazol-4-yl)(2-(methylsulfonyl)-4-(trifluoromethyl)phenyl)methanone
SCHEMBL66989
CHEMBL1887147
AC-24497
methanone, (5-cyclopropyl-4-isoxazolyl)[2-(methylsulfonyl)-4-(trifluoromethyl)phenyl]-
mfcd03095707
isoxaflutole, pestanal(r), analytical standard
C72620
J-007462
DB12938
DS-11149
merlin;rp 201772
Q15632908
AMY3578
rp-201772
rp201772
isoxaflutole 1000 microg/ml in acetone
A925421
CS-0064124
Z3234892128
EN300-7479955

Research Excerpts

Overview

Isoxaflutole is a herbicide activated in soils and plants to its diketonitrile derivative. It has been marketed as a substitute for atrazine.

ExcerptReferenceRelevance
"Isoxaflutole is a preemergence herbicide that has been marketed as a substitute for atrazine. "( Adsorption of isoxaflutole degradates to aluminum and iron hydrous oxides.
Goyne, KW; Lerch, RN; Lin, CH; Wu, SH, )		1.93
"Isoxaflutole is a herbicide activated in soils and plants to its diketonitrile derivative, the active herbicide principle. "( Cleavage of the diketonitrile derivative of the herbicide isoxaflutole by extracellular fungal oxidases.
Boyer, FD; Caminade, E; Mougin, C; Rama, R, 2000)		1.99

Effects

Isoxaflutole has a very short soil half-life and rapidly degrades to a stable and phytotoxic metabolite, diketonitrile.

ExcerptReferenceRelevance
"Isoxaflutole has a very short soil half-life and rapidly degrades to a stable and phytotoxic metabolite, diketonitrile (DKN)."( Degradation of isoxaflutole (balance) herbicide by hypochlorite in tap water.
Garrett, HE; George, MF; Lerch, RN; Lin, CH, 2003)		1.39
"Isoxaflutole has a very short half-life in soil and rapidly degrades to a stable and phytotoxic degradate, diketonitrile (DKN)."( Reaction pathways of the diketonitrile degradate of isoxaflutole with hypochlorite in water.
Leigh, ND; Lerch, RN; Lin, CH, 2007)		1.31
"Isoxaflutole has a very short soil half-life and rapidly degrades to a stable and phytotoxic metabolite, diketonitrile (DKN)."( Degradation of isoxaflutole (balance) herbicide by hypochlorite in tap water.
Garrett, HE; George, MF; Lerch, RN; Lin, CH, 2003)		1.39
"Isoxaflutole has a very short half-life in soil and rapidly degrades to a stable and phytotoxic degradate, diketonitrile (DKN)."( Reaction pathways of the diketonitrile degradate of isoxaflutole with hypochlorite in water.
Leigh, ND; Lerch, RN; Lin, CH, 2007)		1.31

Toxicity

ExcerptReferenceRelevance
" The results of the 90-days subchronic feeding study demonstrated that the GM soybean FG72 is as safe as the conventional non-GM soybean Jack."( No subchronic toxicity of multiple herbicide-resistant soybean FG72 in Sprague-Dawley rats by 90-days feeding study.
He, X; Huang, K; Liu, X; Xie, Z; Xu, W; Zou, S, 2018)		0.48
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
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).
proherbicideA compound that, on administration, must undergo chemical conversion by biochemical (enzymatic), chemical (possibly following an enzymatic step), or physical (e.g. photochemical) activation processes before becoming the pharmacologically active herbicide for which it is a proherbicide.
agrochemicalAn agrochemical is a substance that is used in agriculture or horticulture.
[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 (5)

ClassDescription
cyclopropanesCyclopropane and its derivatives formed by substitution.
isoxazolesOxazoles in which the N and O atoms are adjacent.
aromatic ketoneA ketone in which the carbonyl group is attached to an aromatic ring.
(trifluoromethyl)benzenesAn organofluorine compound that is (trifluoromethyl)benzene and derivatives arising from substitution of one or more of the phenyl hydrogens.
sulfoneAn organosulfur compound having the structure RS(=O)2R (R =/= H).
[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)
AR proteinHomo sapiens (human)Potency27.30600.000221.22318,912.5098AID1259243
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency48.55770.001022.650876.6163AID1224838
glucocorticoid receptor [Homo sapiens]Homo sapiens (human)Potency3.98110.000214.376460.0339AID588533
pregnane X nuclear receptorHomo sapiens (human)Potency70.79460.005428.02631,258.9301AID720659
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_aHomo sapiens (human)Potency76.95880.001723.839378.1014AID743083
Histone H2A.xCricetulus griseus (Chinese hamster)Potency35.73510.039147.5451146.8240AID1224845
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency68.58960.000627.21521,122.0200AID651741
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (40)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's26 (65.00)29.6817
2010's8 (20.00)24.3611
2020's6 (15.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 44.11

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 Index44.11 (24.57)
Research Supply Index3.78 (2.92)
Research Growth Index5.57 (4.65)
Search Engine Demand Index65.02 (26.88)
Search Engine Supply Index2.11 (0.95)

This Compound (44.11)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (2.33%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other42 (97.67%)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.		3.5320benzoic 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
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)		2.0310halide anion;
monoatomic bromine
glycine
[no description available]		2.1710alpha-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
atrazine
[no description available]		2.9840chloro-1,3,5-triazine;
diamino-1,3,5-triazine		environmental contaminant;
herbicide;
xenobiotic
dicamba
Dicamba: A chlorinated organic herbicide.. dicamba : A methoxybenzoic acid that is O-methylsalicylic acid substituted by chloro groups at positions 3 and 6.		7.0310dichlorobenzene;
methoxybenzoic acid		agrochemical;
environmental contaminant;
herbicide;
synthetic auxin;
xenobiotic
diuron
Diuron: A pre-emergent herbicide.. diuron : A member of the class of 3-(3,4-substituted-phenyl)-1,1-dimethylureas that is urea in which both of the hydrogens attached to one nitrogen are substituted by methyl groups, and one of the hydrogens attached to the other nitrogen is substituted by a 3,4-dichlorophenyl group.		7.05103-(3,4-substituted-phenyl)-1,1-dimethylurea;
dichlorobenzene		environmental contaminant;
mitochondrial respiratory-chain inhibitor;
photosystem-II inhibitor;
urea 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.		2.4420aromatic amide;
benzenes;
ether;
organochlorine compound
isoxazoles
Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.		6.08370isoxazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
tocopherols
[no description available]		2.0210
dichloroacetonitrile
dichloroacetonitrile: by-product of water chlorination; structure given in first source		7.610aliphatic nitrile
phosphoric acid, trisodium salt
[no description available]		210sodium phosphate
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.		2.4320chlorine oxoacid;
reactive oxygen species		EC 2.5.1.18 (glutathione transferase) inhibitor;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
human metabolite
chlorine
Chlorine: An element with atomic symbol Cl, atomic number 17, and atomic weight 35, and member of the halogen family.		2.610diatomic chlorine;
gas molecular entity		bleaching agent
chloramine
[no description available]		2.610halide
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.		2.4420
potassium phosphate
potassium phosphate: used in dental materials and to treat hypophosphatemia; RN given refers to cpd with unspecified MF. tripotassium phosphate : An inorganic potassium salt that is the tripotassium salt of phosphoric acid.		210inorganic phosphate salt;
inorganic potassium salt
foe 5043
FOE 5043: an oxyacetamide with herbicidal activity; structure given in first source. flufenacet : An aromatic amide that is acetamide in which the amino hydrogens have been replaced by a propan-2-yl and 4-fluorophenyl groups while the methyl hydrogen is replaced by a [5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy group.		2.5320aromatic amide;
monofluorobenzenes;
thiadiazoles		environmental contaminant;
herbicide;
xenobiotic
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.		2.0110aromatic ketone;
beta-triketone;
cyclohexanones;
sulfone		carotenoid biosynthesis inhibitor;
environmental contaminant;
herbicide;
xenobiotic
ac 263,222
imazapic: imidazolinone herbicide. imazapic : A racemate comprising equimolar amounts of (R)- and (S)-imazapic. It is a selective imidazolinone herbicide for pre- and post-emergent control of some annual and perennial grasses and broadleaf weeds. It kills plants by inhibiting the activity of the enzyme acetohydroxy acid synthase (AHAS).. 5-methyl-2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]pyridine-3-carboxylic acid : A pyridinemonocarboxylic acid that is 5-methylpyridine-3-carboxylic acid which is substituted at position 2 by a 4,5-dihydro-imidazol-2-yl group, which in turn is substituted at positions 4, 4, and 5 by isopropyl, methyl, and oxo groups, respectively.		2.0510imidazolines;
imidazolone;
methylpyridines;
pyridinemonocarboxylic acid
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.		2.0110aromatic ketone;
beta-triketone;
C-nitro compound;
sulfone		carotenoid biosynthesis inhibitor;
EC 1.13.11.27 (4-hydroxyphenylpyruvate dioxygenase) inhibitor;
environmental contaminant;
herbicide;
xenobiotic
riboflavin
vitamin B2 : Any member of a group of vitamers that belong to the chemical structural class called flavins that exhibit biological activity against vitamin B2 deficiency. Symptoms associated with vitamin B2 deficiency include glossitis, seborrhea, angular stomaitis, cheilosis and photophobia. The vitamers include riboflavin and its phosphate derivatives (and includes their salt, ionised and hydrate forms).		7.2110flavin;
vitamin B2		anti-inflammatory agent;
antioxidant;
cofactor;
Escherichia coli metabolite;
food colouring;
fundamental metabolite;
human urinary metabolite;
mouse metabolite;
photosensitizing agent;
plant metabolite
sodium bicarbonate
Sodium Bicarbonate: A white, crystalline powder that is commonly used as a pH buffering agent, an electrolyte replenisher, systemic alkalizer and in topical cleansing solutions.		210one-carbon compound;
organic sodium salt		antacid;
food anticaking agent
plastoquinone
[no description available]		2.0210plastoquinone
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.		3.5580(trifluoromethyl)benzenes;
aromatic ketone;
beta-diketone;
cyclopropanes;
nitrile;
sulfone		agrochemical;
EC 1.13.11.27 (4-hydroxyphenylpyruvate dioxygenase) inhibitor;
herbicide
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.		2.0110
ConditionIndicatedRelationship StrengthStudiesTrials