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首页> 外文期刊>Journal of Agricultural and Food Chemistry >Reaction pathways of the diketonitrile degradate of isoxaflutole with hypochlorite in water.
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Reaction pathways of the diketonitrile degradate of isoxaflutole with hypochlorite in water.

机译：水中异亚硫酸氢盐对二酮腈的降解与异亚氯酸盐的反应途径。

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摘要

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 hypochlorite (OCl-) in tap water, yielding the benzoic acid (BA) degradate as a major product, but the complete reaction pathway and mechanism have not been elucidated. Thus, the objectives of this work were to (1) determine the stoichiometry of the reaction between DKN and OCl-; (2) identify products in addition to BA; and (3) propose a complete pathway and reaction mechanism for oxidation of DKN by OCl-. Stoichiometry of the reaction showed a molar ratio of OCl-/DKN of 2. In addition, two previously uncharacterized chlorinated intermediates were identified under conditions in which OCl- was the limiting reactant. The proposed chemical structure of a chlorinated benzoyl intermediate was inferred from a series of HPLC/MS and HPLC/MS/MS experiments andthe use of mass spectral simulation software. A chlorinated ketone intermediate was also identified using ion trap GC/MS. Two additional end products were also identified: cyclopropanecarboxylic acid (CPCA) and dichloroacetonitrile (DCAN). On the basis of the reaction stoichiometry, the structure of the chlorinated intermediates, and the identification of the products, two reaction pathways are proposed. Both pathways involve a two-step nucleophilic attack and oxidation of the diketone structure of DKN, leading to formation of BA, DCAN, and CPCA.
机译：异恶戊环醇（IXF; Balance）属于一类新的异恶唑除草剂。异沙丁胺醇在土壤中的半衰期非常短，并且会迅速降解为稳定且具有植物毒性的降解物二酮腈（DKN）。先前发现DKN可与自来水中的次氯酸盐（OCl-）快速反应，产生降解为主要产物的苯甲酸（BA），但尚未阐明完整的反应途径和机理。因此，这项工作的目的是（1）确定DKN与OCl-之间反应的化学计量; （2）识别除BA以外的产品; （3）提出了由OCl-氧化DKN的完整途径和反应机理。反应的化学计量比显示OCl- / DKN的摩尔比为2。此外，在OCl-是限制性反应物的条件下，鉴定出两种以前未表征的氯化中间体。从一系列的HPLC / MS和HPLC / MS / MS实验以及质谱模拟软件的使用中可以推断出拟议的氯化苯甲酰中间体的化学结构。还使用离子阱GC / MS鉴定了氯代酮中间体。还确定了另外两种最终产物：环丙烷羧酸（CPCA）和二氯乙腈（DCAN）。根据反应化学计量，氯化中间体的结构以及产物的鉴定，提出了两种反应途径。这两个途径都涉及两步亲核攻击和DKN二酮结构的氧化，从而导致BA，DCAN和CPCA的形成。

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