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
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
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.
Originator
Approval Year
PubMed
Title | Date | PubMed |
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Fate of the herbicide isoxaflutole in the soil of corn fields. | 2001 |
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Kinetics of chemical degradation of isoxaflutole: influence of the nature of aqueous buffers (alkanoic acid/sodium salt vs phosphate). | 2001 Apr |
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Isoxaflutole: the background to its discovery and the basis of its herbicidal properties. | 2001 Feb |
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Soil persistence of 4-HPPD-inhibitors in different soil types. | 2002 |
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Soil metabolism of isoxaflutole in corn. | 2002 Apr |
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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 |
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Effects of moisture, temperature, and biological activity on the degradation of isoxaflutole in soil. | 2002 Sep 25 |
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Degradation of isoxaflutole (balance) herbicide by hypochlorite in tap water. | 2003 Dec 31 |
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Fate of isoxaflutole in soil under controlled conditions. | 2003 Jan 1 |
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The effect of five forage species on transport and transformation of atrazine and isoxaflutole (balance) in lysimeter leachate. | 2003 Nov-Dec |
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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 |
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Effect of soil properties on the degradation of isoxaflutole and the sorption-desorption of isoxaflutole and its diketonitrile degradate. | 2004 Dec 15 |
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Reversal of the inhibition of photosynthesis by herbicides affecting hydroxyphenylpyruvate dioxygenase by plastoquinone and tocopheryl derivatives in Chlamydomonas reinhardtii. | 2004 Jul |
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Interrelationship of macropores and subsurface drainage for conservative tracer and pesticide transport. | 2004 Nov-Dec |
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Population dynamics of Digitaria spp submitted to selection pressure by herbicides in sugarcane crop. | 2005 |
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Characterization of fate and transport of isoxaflutole, a soil-applied corn herbicide, in surface water using a watershed model. | 2005 Nov 2 |
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Differential response of chickpea genotypes to isoxaflutole. | 2006 |
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Influence of an adjuvant on the distribution of herbicides in a sediment/water system. | 2006 |
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Sorption of isoxaflutole diketonitrile degradate (DKN) and dicamba in unsaturated soil. | 2006 |
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Influence of rainfall distribution on simulations of atrazine, metolachlor, and isoxaflutole/metabolite transport in subsurface drained fields. | 2007 Jul 11 |
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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 |
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Reaction pathways of the diketonitrile degradate of isoxaflutole with hypochlorite in water. | 2007 Mar 7 |
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Improved HPLC-MS/MS method for determination of isoxaflutole (balance) and its metabolites in soils and forage plants. | 2007 May 16 |
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Comparison of fate and transport of isoxaflutole to atrazine and metolachlor in 10 Iowa rivers. | 2007 Oct 15 |
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Processes affecting the dissipation of the herbicide isoxaflutole and its diketonitrile metabolite in agricultural soils under field conditions. | 2007 Oct 17 |
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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 |
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[Screening method of pesticides in meat using cleanup with GPC and mini-column]. | 2009 Apr |
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Role of sorption and degradation in the herbicidal function of isoxaflutole. | 2009 Jul |
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Bioavailability of diuron, imazapic and isoxaflutole in soils of contrasting textures. | 2009 Nov |
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Investigation of endogenous soybean food allergens by using a 2-dimensional gel electrophoresis approach. | 2010 Dec |
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Impact of environmental chemicals on key transcription regulators and correlation to toxicity end points within EPA's ToxCast program. | 2010 Mar 15 |
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EPA PESTICIDE CODE |
123000
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1371313
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ANNEX I INDEX 606-054-00-7
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C415327
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isoxaflutole
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SUBSTANCE RECORD