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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
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] But, as shown in the present invention, the substituted diphenylamine compound and its application as insecticide and acaricide have no report

Method used

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  • 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.

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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

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Application Information

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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
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