142994-06-7Relevant articles and documents
Soil metabolism of isoxaflutole in corn
Rouchaud,Neus,Eelen,Bulcke
, p. 280 - 285 (2002)
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.
Reaction pathways of the diketonitrile degradate of isoxaflutole with hypochlorite in water
Lerch,Lin,Leigh
, p. 1893 - 1899 (2007)
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
Synthesis method of 2-methylsulfonyl-4-trifluoromethyl benzoic acid
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, (2020/12/14)
The invention belongs to the field of preparation of pesticide intermediates, and particularly relates to a synthesis method of an intermediate 2-methylsulfonyl-4-trifluoromethyl benzoic acid for preparing important pesticides such as sulfonyl pyrazole an
Cleavage of the diketonitrile derivative of the herbicide isoxaflutole by extracellular fungal oxidases
Mougin,Boyer,Caminade,Rama
, p. 4529 - 4534 (2007/10/03)
Isoxaflutole is a herbicide activated in soils and plants to its diketonitrile derivative, the active herbicide principle. The diketonitrile derivative undergoes cleavage to the inactive benzoic acid analogue. In this paper, it is established that an oxidative mechanism implicating two successive reactions in the presence of dimethyldioxirane can chemically initiate the cleavage of the diketonitrile. It is also shown that two white rot strains, Phanerochaete chrysosporium and Trametes versicolor, are able to convert the diketonitrile to the acid when cultured in liquid media. This main metabolite amounts to 24.6 and 15.1% of initial herbicide content after 12-15 days of culture. Another polar metabolite represents a time course similar to that of diketonitrile degradation. Purified laccase (EC 1.10.3.2), in the presence of 2 mM 2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) acting as a redox mediator at pH 3 supports the reaction with rates of 0.3-0.4 nmol h-1 unit-1.
Herbicidal 2-cyano-1,3-diones
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, (2008/06/13)
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.
4-Benzoylisoxazole derivatives and their use as herbicides
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, (2008/06/13)
4-Benzoyl isoxazole derivatives of general formula (I): wherein:, R1 represents cyclopropyl;, R2 represents -S(O)nR;, R3 represents chlorine, bromine or trifluoromethyl;, R represents methyl; and, n represents 2;, and their use as herbicides is
4 Benzoyl isoxazole derivatives
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, (2008/06/13)
4-Benzoyl isoxazole derivatives of the formula I: wherein:, R represents alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, optionally substituted cycloalkyl, -CO2R3,-COR5,cyano,nitro, -CONR31R4 or a halogen atom;, R1 represents :-, hydrogen , alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl or optionally substituted cycloalkyl, R2 represents :-, halogen, R5, -SR5, -SOR5, -SO2R5, -SO2NR31R4,-CO2R3, -COR5, -CONR31R4, -CSNR31R4, -OR5, a nitro group, a cyano group, a group -O(CH2)q-OR5 or alkyl substituted by OR5;, R3, R31 and R4, which may be the same or different, each represents:-, hydrogen, alkyl or haloalkyl;, R5 represents alkyl or haloalkyl;, n represents an integer from 1 to 5; and, q represents an integer from 1 to 3;, and agriculturally acceptable salts thereof and their use as herbicides is described.
2-Cyano-1,3-dione herbicides
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, (2008/06/13)
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.