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首页> 外文期刊>Journal of Agricultural and Food Chemistry >Synthesis and Herbicidal Activity of lsoindoline-1,3-dione Substituted Benzoxazinone Derivatives Containing a Carboxylic Ester Group
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Synthesis and Herbicidal Activity of lsoindoline-1,3-dione Substituted Benzoxazinone Derivatives Containing a Carboxylic Ester Group

机译：含羧酸酯基的1,3-二吲哚啉-1,3-二酮取代的苯并恶嗪酮衍生物的合成及除草活性

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A carboxylic ester group was introduced to three series of isoindolinedione substituted benzoxazinone derivatives. Some of these analogues exhibited good herbicidal activities, and the injury symptoms against weeds included leaf cupping, crinkling, bronzing, and necrosis, typical of protox inhibitor herbicides. Structurally, they were classified as Chemical Group A (4-carboxylic ester group-6-isoindolinyl-benzoxazinones), B (4-carboxylic ester group-7-isoindolinyl-benzoxazinones), and C (4-carboxylic ester group-6- tetrahydroisoindolinyl-benzoxazinones). All of the tested compounds were structurally confirmed by ~1H NMR, IR, mass spectroscopy, and elemental analysis. Preliminary bioassay data of these three classes of compounds showed that, in general, the order of the herbicidal effectiveness is C > A > B. Several of the lead compounds, for example, C10 (methyl 2-(6-(1,3-dioxo-4,5,6,7-tetrahydro-1 H-isoindol-2(3H)-yl)-7-f luoro-2-methyl-3-oxo-2H-benzo[b][1,4] ox-azin-4(3H)-yl) propano-ate), C12 (ethyl 2-(6-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindoi-2(3H)-yl)-7-fluoro-2- methyl-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl) propanoate), and C13 (ethyl 2-(6-(1,3-di-oxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-7-fluoro-2-methyl-3-oxo-2H-benzo-[i)][1,4]oxazin-4(3H)-yl) butanoate), exhibited greater than 80% control at 75 g a.i./ha in both pre- and postemergence treatments against dicotyledonous weeds, such as Abutilon theophrasti Medic, Chenopodium album L, and Amaranthus ascendens L, and monocotyledon weeds, such as Digitaria sanguinalis L, Echinochloa crus-galli L, and Setaria viridis L. On the basis of advanced screening tests and crop selectivity, compounds C10, C12, and C13 are safer to crops than flumioxazin. Compounds C10, C12, and C13 are potent to develop as pre-emergent herbicides used in peanut, soybean, maize, and cotton fields.
机译：将羧酸酯基引入三个系列的异吲哚二酮取代的苯并恶嗪酮衍生物中。这些类似物中的一些表现出良好的除草活性，对杂草的伤害症状包括叶拔罐，起皱，烫金和坏死，这是protox抑制剂除草剂的典型特征。在结构上，它们被分类为化学组A（4-羧酸酯基-6-异吲哚基-苯并恶嗪酮），B（4-羧酸酯基-7-异吲哚基-苯并恶嗪酮）和C（4-羧酸酯基-6-四氢异吲哚基） -苯并恶嗪酮）。所有测试化合物均通过〜1 H NMR，IR，质谱和元素分析在结构上确认。这三类化合物的初步生物测定数据表明，一般而言，除草效果的顺序为C> A>B。几种先导化合物，例如C10（甲基2-（6-（1,3- dioxo-4,5,6,7-tetrahydro-1 H-isoindol-2（3H）-yl）-7-f luoro-2-methyl-3-oxo-2H-benzo [b] [1,4] ox -azin-4（3H）-基）丙酸酯），C12（乙基2-（6-（1,3-二氧代-4,5,6,7-四氢-1H-isoindoi-2（3H）-基） ）-7-氟-2-甲基-3-氧代-2H-苯并[b] [1,4]恶嗪-4（3H）-基）丙酸酯）和C13（2-（6-（1,3）乙基-di-oxo-4,5,6,7-tetrahydro-1H-isoindol-2（3H）-yl）-7-fluoro-2-methyl-3-oxo-2H-benzo- [i）] [1， 4] oxazin-4（3H）-基）丁酸酯）在芽前和芽后处理中均对双子叶杂草（如Abutilon theophrasti Medic，Cheopodium album L和Amaranthus ascendens）表现出大于80％的防治效果（75 g ai / ha） L，以及单子叶杂草，例如Digitaria sanguinalis L，Echinochloa crus-galli L和Setaria viridisL。在高级筛选试验和作物选择性的基础上，复合C10，C12和C13比氟米嗪对农作物更安全。化合物C10，C12和C13有可能发展为发芽前除草剂，用于花生，大豆，玉米和棉田。

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