Substituted benzene compounds, process for their preparation and herbicidal and defoliant composition containing them

A compound, haloalkyl technology, applied in the field of herbicide and defoliant composition, can solve the problem of not describing the general structure of the compound

Inactive Publication Date: 2001-02-07
ISK AMERICAS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Despite their broad scope, these patents do not describe the

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  • Substituted benzene compounds, process for their preparation and herbicidal and defoliant composition containing them

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Preparation of 3-(4-chloro-6-fluoro-3-methoxy-2-nitrophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound No. 1 -1)

[0063] 3-(4-Amino-6-fluoro-3-methoxyphenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (10 .0g, 29.5mmol) was slowly added to a stirred mixture of concentrated sulfuric acid (36ml) and concentrated nitric acid (4ml). The solution was then slowly warmed to room temperature and allowed to stir for 2 hours. This solution was added to ice water to give a pale yellow precipitate which was isolated by filtration to give the title compound (9.1 g). The NMR data for this compound are listed in Table XVIII. Example 2

Embodiment 2

[0064] 3-(4-Chloro-6-fluoro-3-methoxy-2-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione Preparation (Compound No. 1-5)

[0065] 3-(4-Chloro-6-fluoro-3-methoxy-2-nitrophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (9g, 23. 5mmol) was dissolved in dimethylformamide (90ml), and to this solution were added potassium carbonate (3.9g, 28.2mmol) and dimethyl sulfate (10.2g, 47mmol) with stirring. The solution was stirred at room temperature for 12 hours and water was added. The product was extracted into ethyl acetate and the organic layer was washed with water and dried over anhydrous sodium sulfate. Removal of the solvent gave the crude product, which was purified by silica gel column chromatography. The column was eluted with dichloromethane to give the title compound (7.8g).

Embodiment 3

[0067] Preparation of 3-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound No. 1-4)

[0068] 3-(4-Chloro-6-fluoro-3-methoxy-2-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (7.5g, 18.9mmol) was dissolved in acetic acid (75ml), and 4.2g (75.6mmol) of iron powder was added. The solution was stirred at room temperature under a nitrogen atmosphere for 6 hours and water was added. Extract with ethyl acetate. The organic layer was washed with water, brine, and dried over anhydrous sodium sulfate, followed by evaporation to give the title compound (6.8 g).

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Abstract

Novel herbicidal and defoliant substituted aniline derived compounds represented by general structure (I) are described. W, X, Y, Z, and Q are as defined in the disclosure. Also described are the processes for the manufacture of these compounds and agriculturally suitable compositions containing these as active ingredients which are useful as herbicides for general or selective pre-emergent or post-emergent control of undesired plant species and defoliants at very low concentrations of these biologically active compounds.

Description

[0001] This invention relates to substituted benzene compounds, processes for their preparation, and herbicide and defoliant compositions containing them. Background of the invention [0002] The use of uracil as a herbicide has been previously reported. For example, US Patents 4859229 and 4746352 describe 3-phenyluracil derivatives as herbicides. But the compound has only four substituents in the benzene ring. US Patent 4927451 describes herbicidal compounds having a dihydrouracil ring with five substituents on the benzene ring. EP patent 0705829 describes a uracil herbicide with a pentasubstituent benzene ring linked by carbon at the 2-position of the benzene ring. U.S. Patents 5,346,881, 5,441,925, 5,169,431, 5,476,834, 5,602,077 and WO Patents 97 / 08170, 08171, 12886, and 42188 describe compounds with fused pentasubstituted benzene rings where the 2-position of the benzene ring is substituted by carbon, oxygen, or nitrogen. Uracil herbicide. U.S. Patent No. 5116404 and ...

Claims

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Application Information

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IPC IPC(8): A01N37/32A01N37/34A01N43/38A01N43/40A01N43/54A01N43/56A01N43/58A01N43/64A01N43/653A01N43/713A01N43/90A01N47/06A01N47/20A01N47/22A01N47/24A01N47/30A01N47/34C07C211/52C07C217/84C07D209/48C07D231/16C07D237/14C07D239/54C07D239/553C07D239/56C07D249/12C07D257/04C07D401/12C07D401/14C07D405/12C07D409/12C07D409/14C07D471/04C07D487/04
CPCA01N47/30C07D471/04C07D237/14A01N47/24C07C211/52C07C217/84A01N47/20A01N43/64C07D249/12C07D257/04A01N43/653A01N43/54A01N43/40C07D239/553A01N47/06A01N43/56A01N37/34A01N47/34A01N37/32C07D231/16C07D209/48A01N43/58A01N43/90A01N47/22C07D487/04C07D239/54A01N43/713
Inventor S·古普塔吴少勇塚本正满D·A·普尔曼应百平
Owner ISK AMERICAS
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