N-(2-氟-4-氯-5-取代苯基)异吲哚-1,3-二酮衍生物的合成及除草活性

Synthesis and Herbicidal Activity of N-(4-Chloro-2-fluoro-5-substituted phenyl)isoindole-1,3-dione Derivatives

为了发现新的农药先导化合物,以氯酰亚酞和苯氧羧酸酯结构为基础,通过活性亚结构拼接方法,设计合成了一系列新型的N-(2-氟-4氯-5-取代苯基)异吲哚-1,3-二酮衍生物6a^6f和7a^7k.目标化合物以2-氯-4-氟-5-硝基苯酚为原料,经4步反应制得,其结构经过1H NMR,13C NMR,HRMS确证.初步生物活性测试结果表明,大部分化合物在1500 g/ha剂量下,对双子叶杂草苘麻、反枝苋具有优异的芽前芽后除草活性.进一步活性筛选发现,化合物6d在750g/ha剂量下对苘麻、反枝苋具有100%抑制活性,化合物7a,7i在22.5 g/ha剂量下对苘麻的芽后抑制率大于80%,远高于对照药剂三氟羧草醚.

In order to find new herbicidal leading compounds, a series of N-（4-chloro-2-fluoro-5-substituted phenyl）- isoindole-1,3-dione derivatives （6a^6f, 7a^7k ） were designed and synthesized via the strategy of linking active sub-structures which are chlorophthalim and phenoxy carboxylic ester. The target compounds were synthesized from starting material 2-chloro-4-fluoro-5-nitrophenol in four steps, and their structures were confirmed by 1^H NMR, 13^C NMR and HRMS. The preliminary bioassay results indicated that most compounds exhibited excellent herbicidal activities at 1500 g/ha in both pre- and post-emergence treatments against Abutilon theophrasti and Amaranthus retroflexus. On the basis of advanced screening tests, compound 6d exhibited 100% inhibitory effect against Abutilon theophrasti and Amaranthus retroflexus at 750 g/ha, compounds 7a and 7i were much more effective against Abutilon theophrasti than commercial acifluorfen with 80%~ 86% inhibitory activity at 22.5 g/ha.