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HomeProduct name listISOXAFLUTOLE

ISOXAFLUTOLE

Synonym(s):5-Cyclopropyl-4-[2-(methylsulfonyl)-4-(trifluoromethyl)benzoyl]isoxazole

  • CAS NO.:141112-29-0
  • Empirical Formula: C15H12F3NO4S
  • Molecular Weight: 359.32
  • MDL number: MFCD03095707
  • EINECS: 277-704-1
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-07 13:31:19
ISOXAFLUTOLE Structural

What is ISOXAFLUTOLE?

Description

Isoxaflutole is a 4-benzoyl isoxazole molecule and is used as a pre- and early post-emergence herbicide for the control of a wide range of important broadleaf and grass weeds in maize (Zea mays), both in Europe and in North America. It is also registered for use in sugarcane in Central and South America (2–4). It causes characteristic bleaching of newly developed tissues of susceptible species followed by growth cessation and necrosis. Marketed as Balance for corn (maize) in the United States, and Merlin for corn in Europe; and in sugarcane, it mixes well with metolachlor, acetochlor, dimethenamid, and atrazine to complete the weed spectrum and to reduce the application rates of the latter compounds (2). Isoxaflutole also controls triazineresistant weeds in the field (4).

The Uses of ISOXAFLUTOLE

Herbicide.

The Uses of ISOXAFLUTOLE

Isoxaflutole is an pesticide used to selectively control both grass and broad-leaved weeds in maize and sugar cane. Isoxaflutole is known to work by inhibiting the enzyme 4-Hydroxyphenylpyruvate dioxygenase (HPPD) which results in the disruption of pigment biosynthesis.

Definition

ChEBI: Isoxaflutole is 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. It has a role as an EC 1.13.11.27 (4-hydroxyphenylpyruvate dioxygenase) inhibitor, a proherbicide and an agrochemical. It is a member of cyclopropanes, a member of isoxazoles, an aromatic ketone, a member of (trifluoromethyl)benzenes and a sulfone.

Background

Balance has been investigated for the treatment of Chronic Renal Failure and Peritoneal Membrane Disorder.

Pharmacology

Isoxaflutole is readily taken up by roots and foliar tissues and then rapidly degraded to a diketonitrile derivative (2-cyclopropyl-3-(2-mesyl-4-trifluoromethylphenyl)- 3-oxo propanenitrile) , which is translocated throughout the plant via xylem and phloem (2,3,6,8). It is this metabolite that inhibits HPPD (7), thereby depleting the plastoquinone pools in developing leaves. Plastoquinone is a cofactor in the desaturation of phytoene, levels of which increase in bleached leaves, concomitant with decreases in colored carotenoids (6). Although bleaching is the primary symptom associated with HPPD inhibition, subsequent growth suppression and necrosis are also believed to be a consequence (8).
Isoxaflutole also degrades to the diketonitrile derivative in the soil (3,8). The half-life of isoxaflutole in soil is dependent on soil type, pH, and moisture, ranging from 12 hours to 3 days under laboratory conditions (8). The physicochemical properties of isoxaflutole and of diketonitrile play an important role in both soil and herbicidal activity and selectivity (8).

Metabolism

Not Available

Properties of ISOXAFLUTOLE

Melting point: 138-138.5° (Cain); mp 140°
Boiling point: 575.1±50.0 °C(Predicted)
Density  1.59
Flash point: >130 °C
storage temp.  Sealed in dry,2-8°C
solubility  Chloroform, DCM, Ethyl Acetate, Methanol
form  neat
pka -4.29±0.50(Predicted)
form  Solid
color  White
BRN  8344543
CAS DataBase Reference 141112-29-0
EPA Substance Registry System Isoxaflutole (141112-29-0)

Safety information for ISOXAFLUTOLE

Signal word Warning
Pictogram(s)
ghs
Health Hazard
GHS08
ghs
Environment
GHS09
GHS Hazard Statements H410:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes P202:Do not handle until all safety precautions have been read and understood.
P273:Avoid release to the environment.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P391:Collect spillage. Hazardous to the aquatic environment
P308+P313:IF exposed or concerned: Get medical advice/attention.
P405:Store locked up.

Computed Descriptors for ISOXAFLUTOLE

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