141112-29-0

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;(5-Cyclopropyl-4-isoxazolyl)[2-(methylsulfonyl)-4-(trifluoromethyl)phenyl]methanone
• CAS NO: 141112-29-0
• Molecular Formula: C₁₅H₁₂F₃NO₄S
• Molecular Weight: 359.32
• EINECS: 277-704-1
• Mol File: 141112-29-0.mol

Chemical Properties

• Melting Point: 138-138.5° (Cain); mp 140°
• Boiling Point: 575.1 °C at 760 mmHg
• Flash Point: >130 °C
• Appearance: /
• Density: 1.455 g/cm³
• Vapor Pressure: 3.15E-13mmHg at 25°C
• Refractive Index: 1.534
• Storage Temp.: 0-6°C
• Solubility: Chloroform, DCM, Ethyl Acetate, Methanol
• PKA: -4.29±0.50(Predicted)
• BRN: 8344543
• CAS DataBase Reference: ISOXAFLUTOLE(CAS DataBase Reference)
• NIST Chemistry Reference: ISOXAFLUTOLE(141112-29-0)
• EPA Substance Registry System: ISOXAFLUTOLE(141112-29-0)

Safety Data

• Hazard Codes: Xn,N
• Statements: 50/53-63
• Safety Statements: 36/37-60-61
• RIDADR: UN3077 9/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 141112-29-0(Hazardous Substances Data)

Usage

Uses

Used in Agriculture:
Isoxaflutole is used as a herbicide for controlling a wide range of broadleaf and grass weeds in maize and sugar cane. It is effective against both grass and broad-leaved weeds, providing selective control and enhancing crop yield and quality.
Used in Maize (Zea mays) Cultivation:
Isoxaflutole is used as a preand early post-emergence herbicide in maize cultivation, marketed as Balance for corn (maize) in the United States and Merlin for corn in Europe. It helps in controlling weeds that compete with maize plants for resources, thus promoting healthier growth and increased productivity.
Used in Sugarcane Cultivation:
Isoxaflutole is registered for use in sugarcane cultivation in Central and South America. It is effective in controlling weeds that affect sugarcane growth, leading to improved sugarcane yield and quality.
Used in Combination with Other Herbicides:
Isoxaflutole mixes well with other herbicides such as metolachlor, acetochlor, dimethenamid, and atrazine, providing a comprehensive weed control spectrum and allowing for reduced application rates of the latter compounds.
Used in Controlling Triazine-resistant Weeds:
Isoxaflutole is effective in controlling triazine-resistant weeds in the field, offering an alternative solution for farmers dealing with herbicide-resistant weed populations.

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).

InChI:InChI=1/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

Upstream product

• 765-43-5 Cyclopropyl methyl ketone 
• 192805-69-9 methyl 2-methylmercapto-4-(trifluoromethyl)benzoate 
• 161462-33-5 1-cyano-2-methylthio-4-trifluoromethylbenzene 
• 778-94-9 2-nitro-4-trifluoromethyl-benzonitrile 
• 1383827-77-7 2-methanesulfonyl-4-trifluoromethyl-benzonitrile 

Downstream Products

• 143701-75-1 RPA 202248 
• 142994-06-7 2-(methylsulphonyl)-4-trifluoromethylbenzoic acid 

Relevant articles and documents

Isoxaflutole synthesis method

The invention discloses a isoxaflutole synthesis method, which comprises: obtaining 1-cyclopropyl-3-(2-methylthio-4-trifluoromethylphenyl)propyl-1,3-dione by using cyclopropyl methyl ketone and 2-methylthio-4-trifluoromethyl methylbenzoate as raw materials, oxidizing to obtain 1-cyclopropyl-3-(2-methylsulfonyl-4-trifluoromethylphenyl)propyl-1,3-dione, and carrying out a reaction on the 1-cyclopropyl-3-(2-methylsulfonyl-4-trifluoromethylphenyl)propyl-1,3-dione, triethyl orthoformate and hydroxylamine hydrochloride to obtain the isoxaflutole. The isoxaflutole synthesis method of the present invention has characteristics of high yield, mild reaction condition, short reaction route, and simple operation.

A method for the preparation of isoxazole compounds (by machine translation)

The invention belongs to the field of chemical synthesis, discloses a the isoxazole compounds are of the formula (2) as shown by a compound, the method comprising: in the presence of organic solvent, of formula (1) shown in contact with the water and hydroxylamine compound. The method of the invention without requiring the use of capture can be prepared under the conditions of high purity and high yield of formula (2) shown in the isoxazole compounds. (by machine translation)

NOXIOUS ARTHROPOD CONTROL AGENT CONTAINING AMIDE COMPOUND

An object of the present invention is to provide a compound having the controlling activity on a noxious arthropod, and a noxious arthropod controlling agent containing an amide compound of formula (I): wherein X represents a nitrogen atom or a CH group, p represents 0 or 1, A represents a tetrahydrofuranyl group or the like, R1, R2, R3, R4, R5, R6 and R7 represent a hydrogen atom or the like, n represents 1 or 2, Y represents an oxygen atom or the like, m represents any integer of 0 to 7, and Q represents a C1-8 chain hydrocarbon group optionally having a phenyl group or the like, has the excellent noxious arthropod controlling effect.

Isoxaflutole synthesizing method

The invention discloses an isoxaflutole synthesizing method. According to the method, 2-nitro-4-trifluoromethylbenzonitrile serves as an initial raw material; and isoxaflutole is formed through methylthiolation, catalytic oxidation, condensation, hydrolysis, enolization and a ring-closure reaction. The synthesizing route provided in the method is reasonable; the conversion rate of each step is high; generated intermediates are high in purity; all the intermediates do not need further purification treatment; the process is simple; and the total yield of the isoxaflutole is greater than 73%, and HPLC purity is greater than 98%.

Dicarbonyl aromatic compound and its preparation method and two carbonyl aromatic composition and method for the preparation of isoxazole compounds

Belonging to the field of chemical synthesis, the invention discloses a dicarbonyl aromatic compound shown as formula (1) or its enol form tautomer and a preparation method thereof. The method includes contacting the compound shown as formula (2) with water in the presence of an organic solvent. The invention also discloses a dicarbonyl aromatic composition and a preparation method of an isoxazole compound shown as formula (3). The method includes contacting the compound shown as formula (1) and/or its enol form tautomer with hydroxylamine. The method provided by the invention can prepare high purity and high yield isoxazole compound shown as formula (3) without using an acid-binding agent. (formula (1), formula (2) and formula (3)).

A PROCESS FOR PREPARING ISOXAFLUTOLE

A process for preparing isoxaflutole of formula (I) wherein the process comprises: admixing (5-cyclopropyl-4-isoxazolyl)[2-(methylthio)-4- (trifluoromethyl)phenyl]-methanone of formula (II) with acetic acid, acetic anhydride and hydrogen peroxide in the presence of a strong acid.

Pesticide treatment

A method of accelerating the decomposition of an isoxazole and/or a dione pesticide by contacting them with halogen and/hypohalite. A crop seed containing a halogen and/or hypohalite within the seed or at its surface or in a coating on the seed.

Herbicidal compositions

The invention relates to herbicidal compositions comprising: (a) a 4-benzoylisozaxole of formula I: STR1 wherein R, R1 and R2 are as defined in the description and (b) a chloroacetamide herbicide.

Synergistic herbicidal compositions comprising 4-benzoylisoxazole and dinitroaniline herbicides

The invention relates to synergistic compositions comprising: (a) a 4-benzoylisoxazole of formula (I) STR1 wherein R, R1, R2 and n are as defined in the specification; and (b) a dinitroaniline herbicide; and to the use of these compounds as herbicides.