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Substituted diphenylamine compounds and preparation and application thereof

A compound, diphenylamine technology, applied in the field of acaricide, insecticide, agricultural sterilization, can solve the problem of no biological activity report

Active Publication Date: 2011-09-28
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In addition, the journal Chemische Berichte (1962), 951711-21; Chemische Berichte (1963), 96 (7), 1936-44; Journal of Organic Chemistry (1954), 19, 1641-5, Journal of the Chemical Society, Transactions (1913 ), 103982-8 and Journal ofthe Chemical Society, Transactions (1921), 119, 187-92, etc. disclose the following compounds, but there is no biological activity report

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0142] Example 1: Preparation of compound 2

[0143]

[0144] Take 0.4g (0.01mol) of 60% sodium hydride in the reaction flask, wash with petroleum ether, add 20ml of tetrahydrofuran and stir, add 0.81g (0.005mol) of 2,4-dichloroaniline in batches, and stir at room temperature after adding After 30 minutes, 1.56 g (0.006 mol) of 2,6-dichloro-3,5-dinitrotoluene was dissolved in 30 ml of tetrahydrofuran and then dropped into the reaction flask. After about 30 minutes, the addition was completed, and the stirring was continued at room temperature for 5 hours. After the reaction was monitored by TLC, the reaction solution was filtered, the filtrate was desolvated under reduced pressure, and the compound was purified by column chromatography (eluent: ethyl acetate and petroleum ether (boiling range 60-90°C), volume ratio 1:20) 2. Yellow solid 1.37g, melting point 136-137°C.

[0145] 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 ) δ (ppm): 2.14 (s, 3H), 6.53 (d, 1H), 7.17 (d, 1H...

example 2

[0146] Example 2: Preparation of compound 38

[0147]

[0148] Dissolve 0.56g (0.0015mol) of Compound 2 in 5ml of concentrated sulfuric acid (96%, the same below) and cool to 0℃, mix 0.15g of fuming nitric acid (95%) and 3ml of concentrated sulfuric acid and add to the reaction flask, continue After stirring for 5 minutes, the reaction was monitored by TLC. The reaction solution was poured into ice water. A solid precipitated out. It was filtered. The filter cake was washed with water and dried to obtain compound 38, a brown solid 0.59 g, with a melting point of 156-158°C.

[0149] 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 ) δ (ppm): 2.09 (s, 3H), 7.66 (s, 1H), 8.01 (s, 1H), 8.60 (s, 1H), 9.75 (s, 1H).

example 3

[0150] Example 3: Preparation of compound 43

[0151]

[0152] Take 0.32g (0.008mol) of 60% sodium hydride in the reaction flask, wash with petroleum ether, add 10ml DMF and stir, add 0.83g (0.004mol) of 2,6-dichloro-4-nitroaniline in batches, add After the completion, it was stirred at room temperature for 30 minutes, and then 1.20 g (0.0048 mol) of 2,6-dichloro-3,5-dinitrotoluene was added in portions within 30 minutes, and the reaction was continued for 3 hours at room temperature. After the reaction was monitored by TLC, the reaction solution was poured into 50ml of saturated brine, extracted with ethyl acetate, and the extract was dried over anhydrous magnesium sulfate to remove the solvent under reduced pressure. Column chromatography (eluent: ethyl acetate and petroleum ether (boiling) (Range 60-90℃), volume ratio 1:10) purified to obtain compound 43, yellow solid 1.20g, melting point 157-158℃.

[0153] 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 ) δ (ppm): 2.02 ...

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Abstract

The invention discloses substituted diphenylamine compounds, which is shown as the general formula I. In the formula, each substituent is defined as the description. The compounds shown as the general formula have high activity for various germs in the field of agriculture, and particularly has good control effect on cucumber downy mildew under the condition of small dosage; and the compounds also have higher pesticidal and acaricidal activity. Meanwhile, raw materials for synthesizing the compounds are readily available, the synthesis method is simple and convenient, and the compounds have low cost compared with known bactericides, and have wide application prospect.

Description

Technical field [0001] The invention belongs to the field of agricultural sterilization, insecticide and acaricides. Specifically, it relates to a substituted diphenylamine compound and its preparation and application. Background technique [0002] Diphenylamine and fluazinam are known fungicides. The former is mainly used to prevent and control storage diseases of fruits and vegetables, and the latter is mainly used to prevent and control various diseases of field crops. [0003] The prior art reports that the compounds represented by the following general formula can be used as insecticides, acaricides, fungicides, herbicides, rodenticides or other uses: [0004] [0005] For example, patents BR7900462, CH626323, CN1188757, DE2509416, DE2642147, DE2642148, EP26743, EP60951, GB1544078, GB1525884, JP58113151, JP64001774, JP01186849, WO2002060878, WO2005035498, WO2009037707, US3948US957, US3948988, US4041172, US3948988479, US42US14516, 4,184,460 US4407820, US4459304, US4670596, etc....

Claims

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Application Information

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IPC IPC(8): C07C211/56C07C255/58C07C217/92C07C323/36C07C225/22C07C317/36C07C229/58C07C229/60C07C237/40C07C237/30C07D213/643C07C327/48C07C209/10C07C209/76A01N33/18A01N37/44A01N35/04A01N41/10A01N43/40A01P3/00A01P7/02
CPCC07C255/58C07C327/48A01N37/44C07C237/30A01N37/34A01N33/22A01N41/10C07C237/40C07D213/643A01N43/40A01N33/18C07C317/36C07C323/36C07D213/70C07C211/56
Inventor 刘长令李慧超李志念黄光张弘
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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