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ISOXAFLUTOLE

Basic information Safety Supplier Related

ISOXAFLUTOLE Basic information

Product Name:
ISOXAFLUTOLE
Synonyms:
  • MERLIN
  • BALANCE
  • ISOXAFLUTOLE
  • ISOXAFLUTOLE 45% SOLUTION
  • 5-cyclopropyl-4-[2-(methylsulfonyl)-4-(trifluoromethyl)benzoyl]isoxazole
  • isoxaflutole (bsi, pa iso)
  • isoxaflutole (ISO) 5-cyclopropyl-1,2-oxazol-4-yl α,α,α-trifluoro-2-mesyl-p-tolyl ketone
  • Isoxaflutole 0
CAS:
141112-29-0
MF:
C15H12F3NO4S
MW:
359.32
EINECS:
277-704-1
Mol File:
141112-29-0.mol
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ISOXAFLUTOLE Chemical Properties

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. 
0-6°C
form 
neat
pka
-4.29±0.50(Predicted)
BRN 
8344543
CAS DataBase Reference
141112-29-0
EPA Substance Registry System
Isoxaflutole (141112-29-0)
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Safety Information

Hazard Codes 
Xn,N
Risk Statements 
50/53-63
Safety Statements 
36/37-60-61
RIDADR 
UN3077 9/PG 3
WGK Germany 
3
Toxicity
LD50 in rats, quails, mallard ducks (mg/kg): >5000, >2150, >2150 orally; in rabbits (mg/kg): >2000 dermally (Luscombe)
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ISOXAFLUTOLE Usage And Synthesis

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).

Uses

Herbicide.

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).

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