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Details

Stereochemistry ACHIRAL
Molecular Formula C15H12F3NO4S
Molecular Weight 359.32
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISOXAFLUTOLE

SMILES

CS(=O)(=O)C1=CC(=CC=C1C(=O)C2=C(ON=C2)C3CC3)C(F)(F)F

InChI

InChIKey=OYIKARCXOQLFHF-UHFFFAOYSA-N
InChI=1S/C15H12F3NO4S/c1-24(21,22)12-6-9(15(16,17)18)4-5-10(12)13(20)11-7-19-23-14(11)8-2-3-8/h4-8H,2-3H2,1H3

HIDE SMILES / InChI

Molecular Formula C15H12F3NO4S
Molecular Weight 359.32
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Isoxaflutole is a selective herbicide approved for control of certain broadleaf and grass weeds in field corn and soybean. Isoxaflutole is the first member of a new structural class of herbicides called the isoxazoles. Isoxaflutole works by preventing the biosynthesis of carotenoid pigmentsin both broadleaf and grass weeds. Without carotenoid pigments, chlorophyll pigments are damaged by the sun, and the plant eventually dies. Isoxaflutole is effective against weeds resistant to other herbicide classes such as glyphosate and atrazine. Isoxaflutole was registered conditionally from 1998 to 2004 for weed control in field corn. Isoxaflutole exhibited low acute toxicity via oral, dermal, and inhalation routes of exposure and it is not a dermal sensitizer. In long-term studies via the oral route, isoxaflutole caused ocular toxicity in rats, hepatotoxicity (including liver tumor formation) and thyroid tumors in rats and mice, and hematotoxicity (toxicity to blood) in dogs and mice at high doses. The liver and ocular toxicities observed in rats were consistent with the mode of action of isoxaflutole in mammals (i.e., inhibition of the hepatic enzyme 4-hydroxyphenylpyruvate dioxygenase (HPPD)) that leads to a buildup of tyrosine in the blood and the eye.

Approval Year

PubMed

PubMed

TitleDatePubMed
Fate of the herbicide isoxaflutole in the soil of corn fields.
2001
Kinetics of chemical degradation of isoxaflutole: influence of the nature of aqueous buffers (alkanoic acid/sodium salt vs phosphate).
2001 Apr
Isoxaflutole: the background to its discovery and the basis of its herbicidal properties.
2001 Feb
Soil persistence of 4-HPPD-inhibitors in different soil types.
2002
Soil metabolism of isoxaflutole in corn.
2002 Apr
Determination of isoxaflutole (balance) and its metabolites in water using solid phase extraction followed by high-performance liquid chromatography with ultraviolet or mass spectrometry.
2002 Oct 9
Effects of moisture, temperature, and biological activity on the degradation of isoxaflutole in soil.
2002 Sep 25
Fate of isoxaflutole in soil under controlled conditions.
2003 Jan 1
The effect of five forage species on transport and transformation of atrazine and isoxaflutole (balance) in lysimeter leachate.
2003 Nov-Dec
Degradation of RPA 202248 [U-14C-phenyl]alpha(-(cyclopropylcarbonyl)-2-(methylsulfonyl)-beta-oxo-4-(trifluromethyl)benzenepropanenitrile), the primary degradation product of isoxaflutole, in an outdoor aquatic microcosm system.
2004
Effect of soil properties on the degradation of isoxaflutole and the sorption-desorption of isoxaflutole and its diketonitrile degradate.
2004 Dec 15
Reversal of the inhibition of photosynthesis by herbicides affecting hydroxyphenylpyruvate dioxygenase by plastoquinone and tocopheryl derivatives in Chlamydomonas reinhardtii.
2004 Jul
Interrelationship of macropores and subsurface drainage for conservative tracer and pesticide transport.
2004 Nov-Dec
Population dynamics of Digitaria spp submitted to selection pressure by herbicides in sugarcane crop.
2005
Characterization of fate and transport of isoxaflutole, a soil-applied corn herbicide, in surface water using a watershed model.
2005 Nov 2
Differential response of chickpea genotypes to isoxaflutole.
2006
Influence of an adjuvant on the distribution of herbicides in a sediment/water system.
2006
Sorption of isoxaflutole diketonitrile degradate (DKN) and dicamba in unsaturated soil.
2006
Influence of rainfall distribution on simulations of atrazine, metolachlor, and isoxaflutole/metabolite transport in subsurface drained fields.
2007 Jul 11
Development and validation of a multi-residue method for pesticide determination in honey using on-column liquid-liquid extraction and liquid chromatography-tandem mass spectrometry.
2007 Jun 8
Reaction pathways of the diketonitrile degradate of isoxaflutole with hypochlorite in water.
2007 Mar 7
Improved HPLC-MS/MS method for determination of isoxaflutole (balance) and its metabolites in soils and forage plants.
2007 May 16
Comparison of fate and transport of isoxaflutole to atrazine and metolachlor in 10 Iowa rivers.
2007 Oct 15
Processes affecting the dissipation of the herbicide isoxaflutole and its diketonitrile metabolite in agricultural soils under field conditions.
2007 Oct 17
Temperature and water pressure head effects on the degradation of the diketonitrile metabolite of isoxaflutole in a loamy soil under two tillage systems.
2008 Dec
[Screening method of pesticides in meat using cleanup with GPC and mini-column].
2009 Apr
Role of sorption and degradation in the herbicidal function of isoxaflutole.
2009 Jul
Bioavailability of diuron, imazapic and isoxaflutole in soils of contrasting textures.
2009 Nov
Investigation of endogenous soybean food allergens by using a 2-dimensional gel electrophoresis approach.
2010 Dec
Impact of environmental chemicals on key transcription regulators and correlation to toxicity end points within EPA's ToxCast program.
2010 Mar 15
Patents

Sample Use Guides

LD50 Rat oral >5000 mg/kg LD50 Rabbit dermal >2000 mg/kg
Route of Administration: Other
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:58:29 GMT 2023
Edited
by admin
on Fri Dec 15 17:58:29 GMT 2023
Record UNII
0T9R0O0EYT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ISOXAFLUTOLE
HSDB   ISO   MI  
Common Name English
(5-CYCLOPROPYL-1,2-OXAZOL-4-YL)(.ALPHA.,.ALPHA.,.ALPHA.-TRIFLUORO-2-MESYL-P-TOLYL)METHANONE
Common Name English
ISOXAFLUTOLE [ISO]
Common Name English
ISOXAFLUTOLE [MI]
Common Name English
RPA-201772
Code English
5-CYCLOPROPYL-4-(2-METHANESULFONYL-4-TRIFLUOROMETHYLBENZOYL)ISOXAZOLE
Systematic Name English
ISOXAFLUTOLE [HSDB]
Common Name English
(5-CYCLOPROPYL-4-ISOXAZOLYL)(2-(METHYLSULFONYL)-4-(TRIFLUOROMETHYL)PHENYL)METHANONE
Systematic Name English
BALANCE
Brand Name English
264-EUP-99
Code English
5-CYCLOPROPYLISOXAZOL-4-YL 2-MESYL-4-TRIFLUOROMETHYLPHENYL KETONE
Systematic Name English
MERLIN
Brand Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 123000
Created by admin on Fri Dec 15 17:58:29 GMT 2023 , Edited by admin on Fri Dec 15 17:58:29 GMT 2023
Code System Code Type Description
CHEBI
141213
Created by admin on Fri Dec 15 17:58:29 GMT 2023 , Edited by admin on Fri Dec 15 17:58:29 GMT 2023
PRIMARY
FDA UNII
0T9R0O0EYT
Created by admin on Fri Dec 15 17:58:29 GMT 2023 , Edited by admin on Fri Dec 15 17:58:29 GMT 2023
PRIMARY
RXCUI
1371313
Created by admin on Fri Dec 15 17:58:29 GMT 2023 , Edited by admin on Fri Dec 15 17:58:29 GMT 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
ANNEX I INDEX 606-054-00-7
Created by admin on Fri Dec 15 17:58:29 GMT 2023 , Edited by admin on Fri Dec 15 17:58:29 GMT 2023
PRIMARY
PUBCHEM
84098
Created by admin on Fri Dec 15 17:58:29 GMT 2023 , Edited by admin on Fri Dec 15 17:58:29 GMT 2023
PRIMARY
EPA CompTox
DTXSID5034723
Created by admin on Fri Dec 15 17:58:29 GMT 2023 , Edited by admin on Fri Dec 15 17:58:29 GMT 2023
PRIMARY
HSDB
7275
Created by admin on Fri Dec 15 17:58:29 GMT 2023 , Edited by admin on Fri Dec 15 17:58:29 GMT 2023
PRIMARY
DRUG BANK
DB12938
Created by admin on Fri Dec 15 17:58:29 GMT 2023 , Edited by admin on Fri Dec 15 17:58:29 GMT 2023
PRIMARY
MESH
C415327
Created by admin on Fri Dec 15 17:58:29 GMT 2023 , Edited by admin on Fri Dec 15 17:58:29 GMT 2023
PRIMARY
ALANWOOD
isoxaflutole
Created by admin on Fri Dec 15 17:58:29 GMT 2023 , Edited by admin on Fri Dec 15 17:58:29 GMT 2023
PRIMARY
CAS
141112-29-0
Created by admin on Fri Dec 15 17:58:29 GMT 2023 , Edited by admin on Fri Dec 15 17:58:29 GMT 2023
PRIMARY
CHEBI
3612
Created by admin on Fri Dec 15 17:58:29 GMT 2023 , Edited by admin on Fri Dec 15 17:58:29 GMT 2023
PRIMARY
MERCK INDEX
m6553
Created by admin on Fri Dec 15 17:58:29 GMT 2023 , Edited by admin on Fri Dec 15 17:58:29 GMT 2023
PRIMARY Merck Index