143701-75-1

Usage

Uses

RPA 202248 is a derivative of isoxaflutole, a herbicide used for weed control.

InChI:InChI=1/C15H12F3NO4S/c1-24(22,23)12-6-9(15(16,17)18)4-5-10(12)14(21)11(7-19)13(20)8-2-3-8/h4-6,8,11H,2-3H2,1H3

Upstream product

• 141112-29-0 isoxaflutole 

Downstream Products

• 13885-13-7 2-cyclopropyl-2-oxoacetic acid 
• 142994-06-7 2-(methylsulphonyl)-4-trifluoromethylbenzoic acid 

Relevant academic research and scientific papers

Kinetics of chemical degradation of isoxaflutole: Influence of the nature of aqueous buffers (alkanoic acid/sodium salt vs phosphate)

A kinetic study of the chemical degradation of isoxaflutole (5-cyclopropyl-1,2-oxazol-4-ylααα-trifluoro-2-mesyl-p-tolyl ketone) into its diketonitrile derivative (DKN), which is its active herbicide principle, in organic buffers at different pH values was carried out using a HPLC/UV detection method. The values of the pseudo-first-order rate constants Kobs for the reaction were calculated and compared with those previously obtained in inorganic buffers. In both cases, Kobs was found to be dependent on pH and temperature, but at pH 5.2 the degradation of isoxaflutole in CH3COOH/CH3COONa buffers was considerably faster than in KH2PO4/Na2HPO4 buffers, indicating that the compound was sensitive to the nature of the reagents used to prepare buffered solutions. The influence of phosphate and acetate concentrations and the influence of the R-substituent in RCOOH/RCOONa buffers were investigated. For the HA/A- buffers studied, the values of Kobs were linearly dependent on HA and A- concentrations, which meant that the degradation of isoxaflutole was subject to general catalysis. The values of Kobs were also found to be dependent on the number and the position of the CH3 groups of the R-substituent. The known degradation product of DKN (a benzoic acid derivative) was not detected throughout this study.

Reaction pathways of the diketonitrile degradate of isoxaflutole with hypochlorite in water

Isoxaflutole (IXF; Balance) belongs to a new class of isoxazole herbicides. Isoxaflutole has a very short half-life in soil and rapidly degrades to a stable and phytotoxic degradate, diketonitrile (DKN). DKN was previously discovered to rapidly react with

Soil metabolism of isoxaflutole in corn

The herbicide isoxaflutole 1 (5-cyclopropyl-4- isoxazolyl)[2-(methylsulfonyl)-4-(trifluoromethyl)phenyl]- methanone) has been applied preemergence at the rate of 125 g ha-1 on corn crops grown on fields located in regions different as to their soil textures. Its metabolite diketonitrile 2(2-cyano-3-cyclopropyl-1- (2-methylsulfonyl-4-trifluoromethylphenyl)-propane-1,3-dione) - which is the herbicide's active compound - and its nonherbicide metabolite 3 (2-methylsulfonyl-4-trifluoromethylbenzoic acid) were measured in the 0-10 cm surface soil layer of the corn crops after the treatment and until the harvest. At the opposite of what occurred in plant shoots, the transformation of isoxaflutole 1 into diketonitrile 2 was not immediate in soil. In the 0-10 cm surface soil layer, this transformation occurred progressively according to an apparent second-order kinetics, and the soil half-lives of isoxaflutole 1 self were comprised between 9 and 18 days. The adsorption of isoxaflutole 1 onto the solid phase of the soil and its organic matter should explain the stabilization effect of soil, increased by the application of fresh organic fertilizer. The sum of the concentrations of isoxaflutole 1 and diketonitrile 2 disappeared in the 0-10 cm surface soil layer according to an apparent first-order kinetics, and the soil half-lives of this sum were comprised between 45 and 65 days. The sum of the concentrations of isoxaflutole 1 and of its metabolites diketonitrile 2 and acid 3 did not account for the amount of isoxaflutole 1 applied. The discrepancy increased with the delay after the application, showing that the acid 3 was further metabolized in soil into common nontoxic products, and ultimately into CO2. The conjunction of the adsorption of isoxaflutole and its metabolites (which reduced their mobilities) onto the soil and its organic matter, and their further metabolism should explain why isoxaflutole and its metabolites were not detected in the 10-15 and 15-20 cm surface soil layers during the crops.

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 2-cyano-1,3-diones

Herbicides derived from 2-cyano-1,3-diones have the formula: STR1 wherein R, R1, R2 R3, R4 and R5 are as defined in the description. The compounds are intended for use pre- and post-emergence as selective herbicides in maize and a large number of other monocotyledon crops.

2-Cyano-1,3-dione herbicides

Compounds of formula: wherein:, R represent an optionally substituted alkyl or an optionally substituted cycloalkyl group;, R1 represents halogen, hydrogen, nitro, -O(CH2)mOR5, cyano, -SR5, R5, OR5, CO2R5 or alkyl substituted by OR5;, R2 and R3 represent a halogen, hydrogen, R5, alkyl substituted by -OR5, -O(CH2)mOR5, nitro, cyano, -OR5 or -CO2R5;, R4 and R5 represent an optionally substituted alkyl group;, n represents zero, 1 or 2 and, m represents an integer from 1 to 3;, and agriculturally acceptable salts of enolic tautomeric forms thereof are useful as herbicides.