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

A compound, fluorophenyl 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: 2005-09-28
ISK AMERICAS
View PDF27 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Despite their broad scope, these patents do not describe the general structure of the compounds of the present invention

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Substituted benzene compounds, process for their preparation, and herbicidal and defoliant compositions containing them
  • Substituted benzene compounds, process for their preparation, and herbicidal and defoliant compositions containing them
  • Substituted benzene compounds, process for their preparation, and herbicidal and defoliant compositions containing them

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0078] Scheme 9 shows the preparation method of the intermediate represented by general formula V. The starting material represented by the general formula XXXIX can be prepared according to the literature method of Japanese Patent 01186849 (1989), by nitrating XXXVII to obtain XXXVIII, and then reducing to XXXIX. The amino group in XXXIX is protected by the formation of amide or carbamate XL and nitration of the latter to XLI. XLI deprotection to obtain o-nitroaniline V. V can be converted into the desired compound represented by the general formula XLV according to the method shown in the scheme.

[0079] Process 9

[0080]

[0081] (a)H 2 SO 4 -HNO 3 ; (B) Fe-AcOH; (c) pyridine-ClCOOEt (such as J=NHCOOEt); (d) H 2 SO 4 -HNO 3 ; (E) HBr-AcOH; (f) 1) triphosgene 2) NaH, 3-amino-4,4,4-trifluorobutenoic acid ethyl ester 3) CH 3 I(Q=uracil ring in X, R 1 =CH 3 , R 2 =CF 3 ); (g) ROH, alkali (example T=O, R=CH 3 )(h)Fe-AcOH(i)(CF 3 CO) 2 O (e.g. Z=NHCO CF 3 )

...

Embodiment 1

[0115] Preparation of 3-(4-chloro-6-fluoro-3-methoxy-2-nitrophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound No. 1 -1)

[0116] At -15°C, 3-(4-chloro-6-fluoro-3-methoxyphenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (10.0 g, 29.5mmol) was slowly added to the stirring 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 obtain a pale yellow precipitate, which was separated by filtration to obtain the title compound (9.1 g). The NMR data of this compound are listed in Table XVIII.

Embodiment 2

[0118] 3-(4-Chloro-6-fluoro-3-methoxy-2-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione Preparation (Compound No. 1-5)

[0119] The 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 potassium carbonate (3.9g, 28.2mmol) and dimethyl sulfate (10.2g, 47mmol) were added to this solution under 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 with anhydrous sodium sulfate. The solvent was removed to obtain the crude product, which was purified by silica gel column chromatography. The column was eluted with dichloromethane to obtain the title compound (7.8 g).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
particle sizeaaaaaaaaaa
Login to view more

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 application is a divisional application of Chinese Patent Application No. 98812711.3 filed on June 27, 2000. [0002] The present invention relates to substituted benzene compounds, their preparation methods, and herbicide and defoliant compositions containing them. Background of the invention [0003] There have been reports of using uracil as a herbicide. For example, U.S. Patent Nos. 4,859,229 and 4,746,352 describe 3-phenyluracil derivatives as herbicides. However, there are only four substituents in the benzene ring of the compound. US Patent 4,927,451 describes herbicidal compounds with dihydrouracil rings with five substituents on the benzene ring. EP Patent 0705829 describes a uracil herbicide with a five-substituent benzene ring attached to the 2-position of the benzene ring. U.S. Patents 5,346,881, 5,419,925, 5,169,431, 5476834, 5,602,077 and WO patents 97 / 08170, 08171, 12886, and 42188 describe fused five-substituted benzene rings (where the 2-position of the...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap