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Chemical Identification
Common Name
Isoxaflutole
中文通用名
异噁唑草酮
IUPAC
5-cyclopropyl-4-(2-methylsulfuron-4-trifluoromethylbenzoyl) isoxazole
CAS
(5-cyclopropyl-4-isoxazolyl)[2-(methylsulfonyl)-4-(trifluoromethyl)phenyl]methanone
CAS No.
141112-29-0
Molecular Formula
C15H12F3NO4S
Molecular Structure
Category
Activity
Herbicide
Isoxaflutole is a systemic herbicide – it is translocated throughout the plant following absorption through the roots and foliage and is rapidly converted in planta to the biologically active diketonitrile, which is then detoxified to the inactive metabolite, 2-methylsulphonyl-4-trifluoromethylbenzoic acid. The activity of the product is through the inhibition of the enzyme p-hydroxy phenyl pyruvate dioxygenase (HPPD), which converts p-hydroxy phenyl pyruvate to homogentisate, a key step in plastoquinone biosynthesis.


Isoxaflutole can be applied pre-emergence, pre-plant or pre-plant incorporated in maize and pre-emergence or early post-emergence in sugar cane. The higher rate is required for pre-plant applications.

Control of more than 40 broadleaf and grass weeds can be achieved with Balance though combinations with reduced rates of graminicides such as acetochlor are recommended for improved grass control. The difference in mode of action from the triazine family suggests that isoxaflutole will play a role in the management of triazine resistant weed species. Following application, weeds either do not emerge or emerge bleached. Optimum activity is obtained when the product is applied in moist conditions. Isoxaflutole applied pre-plant may provide 8-10 weeks residual action and a unique ‘recharge’ effect has been demonstrated in field trials where weeds up to 2 inches (5 cm) tall can be controlled following rainfall. Under certain conditions, some transient phytotoxicity to young maize plants may occur. The company reports that rotation crops are unaffected by isoxaflutole.

For applications to sugar cane in Australia, Balance is not susceptible to degradation on hot, dry soil, and does not need to be incorporated into the soil by mechanical means.

Aventis identified a number of options for use of the 4SC formulation launched in 2001. The product can be used in a one-pass program or used in conjunction with a low rate of atrazine. Two-pass programs (e.g. Balance Pro followed by Liberty) are also recommended.

Reports in the literature (Weed Science, 1999) suggest that injury to maize following pre-emergence treatments of isoxaflutole can be reduced by the use of safeners such as R-29148 or MON-13900 and that the mechanism of safening is via enhanced oxidative metabolism of both parent and diketonitrile.

In field trials, isoxaflutole gave similar levels of control to standard herbicide treatments but at application rates nearly 50 times lower. It controls triazine-resistant weeds both when used alone and in mixtures. The company recommends that it is used in mixtures, and in rotation or sequence with other herbicides to delay the onset of resistance.

This product must not be applied to sandy or loamy soils or to soils with less than 2% organic matter. In order to counteract potential toxicity to fish, aquatic plants and invertebrates, a 22 metre buffer zone is required to protect sensitive areas, such as wetlands, ponds, lakes and rivers.
CropUse
CropUses:
chickpeas, cotton, maize, ornamentals, potatoes, sugar cane, sweet potatoes

Sugar cane

75 g ai/ha (dry season), 112.5 g ai/ha (wet season)

Maize

60-130 g ai/ha

Premix
Thiencarbazone-methyl+isoxaflutole
Isoxaflutole+Atrazine

Suspension concentrate (SC) ;Water-dispersible granule (WG) 
Premix Parters: copper oxychloride; phthalide;

Physical Properties
Molecular weight:359.3; Physical form:Off-white or pale yellow solid. Density:1.590; Composition:Tech. is c. 98% pure. Melting point:140 °C; Vapour pressure:1 × 10-3 mPa (25 °C); Henry constant:1.87 × 10-5 Pa m3 mol-1 (20 °C); Partition coefficient(n-octanol and water):logP = 2.32; Solubility:In water 6.2 mg/l ( pH 5.5, 20 °C).; Stability:Stable to heat (14 d at 54 °C) and to light. DT50 in water 1 d at pH 7.
Toxicology
Oral:Acute oral LD50 for rats >5000 mg/ kg. Percutaneous:Acute percutaneous LD50 for rabbits >2000 mg/kg. Not a skin irritant; minimal eye irritation (rabbits). Not a skin sensitiser. Inhalation: LC50 (4 h) for rats >5.23 mg/l. ADI:0.056 mg/ kg b.w.
Environmental Profile

Ecotoxicology: 
Algae: EC50 for Selenastrum capricornutum 0.016 mg/l.Bees:< LD50 (oral and contact) >100 μg/bee.Birds:Acute oral LD50 (14 d) for quail and mallard ducks >2150 mg/ kg; dietary LC50(8 d) >5000 ppm.Daphnia:Non-toxic at limit of water solubility.Fish:Non-toxic at limit of water solubility.Worms:Non-toxic at 1000 mg/ kg.Other aquatic spp.: EC50 (96 h) for Eastern oyster (Crassostrea virginica) 3.4 mg/l, mysid shrimp (Mysidopsis bahia) 18 μg/l. 

Environmental fate: 
Animals:Following oral administration, isoxaflutole is rapidly excreted.Soil:In laboratory soil studies, degradation proceeds via hydrolysis and microbial degradation, with final mineralisation to CO2. Isoxaflutole and its major metabolites are potentially mobile in soil under simulated high rainfall;  Plant metabolism study demonstrated that residue levels at harvest are very low, and comprise mainly a non-toxic metabolite.
Fate in soil:

Isoxaflutole is degraded microbially and chemically in soil.
Soil photolysis: Half-life 23 hours
Soil metabolism: Half-life 2.4 days (aerobic soil)
Soil metabolism: Half-life < 2 hours (anaerobic aquatic soil)
Field dissipation: Half-life 1.4 - 3.0 days.
Soil mobility: very mobile in sand / sandy loam soils. Low mobility in silty clay and loam sediment.
Soil mobility (aged): Generally not found below 6cm soil depth
Hydrolysis: Half-life 11.1, 20.1, 3.2 hours at pH 5, 7, 9
Aqueous photolysis: Half-life 6.7 days
The primary metabolite (diketonitrile RPA 202248) is stable to hydrolysis at pH7, stable to photolysis in water, is potentially very mobile and has a half-life of 61 days in aerobic soil metabolism studies.
The terminal metabolite (RPA 203328) is stable to hydrolysis at pH7, stable to photolysis in water, is potentially very mobile and has a half-life of 977 days in aerobic soil metabolism studies.
The EPA pesticide factsheet reports that the persistence and mobility of isoxaflutole and the diketonitrile is likely to lead to accumulation in groundwater and surface waters. Modelling data indicate that diketonitrile may accumulate in concentrations that could cause phytotoxicity in non-target plant species. Consequently, a programme of prospective groundwater and surface water monitoring was initiated in order to clarify the environmental impact of isoxaflutole.

Transport Information
Signal Word:CAUTION; Hazard Class:III(Slightly hazardous)

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