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

doi:10.6023/cjoc201408006

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (1): 159-166.DOI: 10.6023/cjoc201408006 Previous Articles Next Articles

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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

张浩^a, 李奇博^a, 刘克昌^a, 刘瑞全^a, 李青阳^a, 汪清民^b, 刘尚钟^a

a 中国农业大学理学院应用化学系北京 100193;
b 南开大学元素有机化学国家重点实验室天津 300071

收稿日期:2014-05-12 修回日期:2014-08-01 发布日期:2014-09-16
通讯作者: 汪清民, 刘尚钟 E-mail:chemlab.lnnu@163.com
基金资助:
辽宁省自然科学基金(No. 20102126)资助项目.

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

Zhang Hao^a, Li Qibo^a, Liu Kechang^a, Liu Ruiquan^a, Li Qingyang^a, Wang Qingmin^b, Liu Shangzhong^a

a Department of Applied chemistry, College of Science, China Agricultural University, Beijing 100193;
b State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071

Received:2014-05-12 Revised:2014-08-01 Published:2014-09-16
Supported by:
Project supported by the Natural Science Foundation of Liaoning Province (No. 20102126).

1. Synthesis and Herbicidal Activity of N-(4-Chloro-2-fluoro-5- substituted phenyl)isoindole-1,3-dione Derivatives.PDF(1301KB)

Abstract

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 ¹H NMR, ¹³C 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.

Key words: protoporphyrinogen oxidase inhibitor, N-phenyl isoindole-1,3-dione, phenoxy carboxylic ester, herbicidal activity

Cite this article

Zhang Hao, Li Qibo, Liu Kechang, Liu Ruiquan, Li Qingyang, Wang Qingmin, Liu Shangzhong. Synthesis and Herbicidal Activity of N-(4-Chloro-2-fluoro-5- substituted phenyl)isoindole-1,3-dione Derivatives[J]. Chin. J. Org. Chem., 2015, 35(1): 159-166.

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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

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