Substituted diphenylamine compounds and application thereof

A technology of a compound, diphenylamine, which is applied to substituted diphenylamine compounds and their application fields, and can solve the problems that the application of diphenylamine compounds as insecticides and acaricides has not been reported.

Active Publication Date: 2014-01-29
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
View PDF10 Cites 14 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] But, as shown in the present invention, the substituted diphenylami

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 diphenylamine compounds and application thereof
  • Substituted diphenylamine compounds and application thereof
  • Substituted diphenylamine compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0121] Embodiment 1: the preparation of compound 25

[0122]

[0123] Add 0.83g (0.004mol) of 2,6-dichloro-4-nitroaniline in batches to 0.32g (0.008mol) of 60% sodium hydride in 10mL of N,N-methylformamide (DMF) suspension After the addition was completed, stir at room temperature for 30 minutes, then add 1.04 g (0.0048 mol) 2-chloro-3,5-dinitrotoluene in batches within 30 minutes, and continue the reaction at room temperature for 3 hours. After the completion of the TLC monitoring reaction, the reaction solution was poured into 50mL saturated brine, extracted with ethyl acetate, the extract was dried with anhydrous magnesium sulfate and precipitated under reduced pressure, column chromatography (eluent was ethyl acetate and sherwood oil (boiling (range 60-90°C), volume ratio 1:10) to obtain compound 25, 0.96 g of yellow solid, melting point 146-148°C. 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 )δ (ppm): 9.00 (s, 1H), 8.95 (d, 1H), 8.29 (s, 2H), 8.26 (d, 1H), ...

Embodiment 2

[0124] Embodiment 2: the preparation of compound 158

[0125]

[0126] Intermediate A was prepared according to the method described in Example 1, a yellow solid with a melting point of 124-126°C. 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 )δ(ppm):9.06(s,1H),8.98(d,1H),8.19(d,1H),7.19-7.27(m,1H),6.96-7.03(m,2H),2.02(s,3H ).

[0127] Dissolve 0.80g (0.0026mol) of intermediate A in 30mL of butanone, add 1.26g (0.010mol) of dimethyl sulfate and 2.76g (0.020mol) of potassium carbonate, and react under reflux for 8 hours. The completion of the reaction was monitored by TLC, filtered, the filtrate was precipitated under reduced pressure, and purified by column chromatography (eluent: ethyl acetate and petroleum ether (boiling range 60-90°C), volume ratio: 1:20) to obtain intermediate B, brown The solid is 0.76g, and the melting point is 116-118°C. 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 )δ(ppm):8.53(d,1H),8.23(d,1H),7.05-7.08(m,1H),6.87-6.93(m,2H),...

Embodiment 3

[0142] Embodiment 3: 30% wettable powder

[0143]

[0144] Compound 7 and other components were fully mixed and pulverized by a superfine pulverizer to obtain a 30% wettable powder product.

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
Melting pointaaaaaaaaaa
Login to view more

Abstract

The invention discloses substituted diphenylamine compounds. The substituted diphenylamine compounds are shown in general formula I, wherein all the substituents in the formula are defined in the specification. The compounds in the general formula I can present very good activity to various injurious insects and injurious mites in the technical fields of agriculture, civil uses and animals, and especially can present very good treatment and control effects on diamondback moth, armyworm, aphid and tetranychus cinabarinus boisdu. Simultaneously, the raw materials for synthesizing the substituted diphenylamine compounds are easily available, the synthesis method is simple and convenient, the cost is low when compared with that of known insecticides and miticides, and therefore the substituted diphenylamine compounds are wide in application prospect.

Description

technical field [0001] The invention belongs to the field of pesticides and acaricides for agriculture, civilian use and animal technology. In particular, it relates to a substituted diphenylamine compound and its application. Background technique [0002] Journal of the Chemical Society (1924), Transactions, 125, 2400-4; Journal of the Chemical Society (1930), 1218-22; Journal of the Chemical Society (1932), 2363-4; Journal of the Chemical Society (1951 ), 110-15; Helvetica Chimica Acta (1975), 58 (1), 257-68; Science of Synthesis (2004), 17, 55-115; Chemische Berichte (1962), 95, 1711-21 disclosed C- 1. Compounds such as C-2, but their biological activity has not been reported. [0003] [0004] ACS Symposium Series (1992), 504 (Synth.Chem.Agrochem.III), 336-48 reported that the compound shown in the following general formula has acaricidal activity, wherein compound C-3 is active against citrus rust mite at 1000ppm 19%. [0005] [0006] Patent JP58113151 report...

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
IPC IPC(8): C07C211/56C07C209/10C07C255/58C07C253/30A01N33/18A01N37/44A01P7/02A01P7/04
Inventor 李慧超关爱莹宋玉泉杨吉春王斌刘长令
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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