Substituted nitroaniline compound and its application

A technology of nitroaniline and compounds, which is applied in the field of substituted nitroaniline compounds, and can solve problems such as unreported structural compounds

Active Publication Date: 2012-12-19
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the prior art, the structure of the compound shown in the general formula I of the present invention has not been reported

Method used

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  • Substituted nitroaniline compound and its application
  • Substituted nitroaniline compound and its application
  • Substituted nitroaniline compound and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0126] Embodiment 1: the preparation of compound IA-1

[0127]

[0128] Dissolve 0.47g (0.005mol) of 2-aminopyridine in 10mL of N,N-methylformamide, add 0.4g (0.01mol) of sodium hydroxide under stirring, and add 1.26g (0.005mol) to it after 10 minutes After adding 2,6-dichloro-3,5-dinitrotoluene, continue stirring at room temperature for 5 hours. After TLC monitors that the reaction is complete, the reaction solution is poured into 50 mL of saturated brine, extracted with ethyl acetate, the organic phase is dried with anhydrous magnesium sulfate and precipitated under reduced pressure, and the residue is column chromatographed (eluent is ethyl acetate and petroleum ether). (boiling range 60-90°C), volume ratio 1:10) purified to obtain 1.21 g of solid, namely compound IA-1. The melting point is 111-113°C.

[0129] 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 )δ(ppm):2.26(s,3H),6.90(d,1H),6.96-7.00(m,1H),7.65-7.71(m,1H),8.19-8.22(m,1H),8.60(s ,1H), 8.94(d,1H). ...

Embodiment 2

[0130] Embodiment 2: the preparation of compound IA-28

[0131]

[0132] Dissolve 0.64g (0.005mol) of 2-amino-5-chloropyridine in 10mL of N,N-dimethylformamide, add 0.4g (0.01mol) of sodium hydroxide under stirring, and add 1.26 g (0.005mol) 2,6-dichloro-3,5-dinitrotoluene, after the addition, continue to stir at room temperature for 5 hours. After TLC monitors that the reaction is complete, the reaction solution is poured into 50 mL of saturated brine, extracted with ethyl acetate, the organic phase is dried with anhydrous magnesium sulfate and precipitated under reduced pressure, and the residue is column chromatographed (eluent is ethyl acetate and petroleum ether). (Boiling range 60-90°C, volume ratio 1:10) Purified to obtain 1.45 g of solid, namely compound IA-28. The melting point is 168-170°C.

[0133]1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 )δ (ppm): 2.25 (s, 3H), 6.86 (d, 1H), 7.63 (dd, 1H), 8.13 (d, 1H), 8.59 (s, 1H), 8.89 (s, 1H).

Embodiment 3

[0134] Embodiment 3: the preparation of compound IA-230

[0135]

[0136] Dissolve 1.16g (0.005mol) of 3-amino-2,6-dichloro-4-trifluoromethylpyridine in 10mL of N,N-dimethylformamide, and add 0.4g (0.01mol) of hydrogen under stirring Sodium oxide, 1.26g (0.005mol) 2,6-dichloro-3,5-dinitrotoluene was added to it after 10 minutes, and stirring at room temperature was continued for 5 hours after the addition. After TLC monitors that the reaction is complete, the reaction solution is poured into 50 mL of saturated brine, extracted with ethyl acetate, the organic phase is dried with anhydrous magnesium sulfate and precipitated under reduced pressure, and the residue is column chromatographed (eluent is ethyl acetate and petroleum ether). (Boiling range 60-90°C, volume ratio 1:10) Purified to obtain 1.88g of compound IA-230. The melting point is 130-132°C.

[0137] 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 )δ (ppm): 2.00 (s, 3H), 7.67 (s, 1H), 8.74 (s, 1H), 9.59 ...

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Abstract

The invention discloses a substituted nitroaniline compound. The structure of the compound is represented by formula I, and all substituents in the formula I are defined in the specification. The compound of the general formula I has a very good bacterial activity in the agricultural field, and especially has a very good control effect on rice blast, cucumber downy mildew, cucumber gray mold, wheat powdery mildew and corn rust at a low dosage.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides. Specifically, it relates to a substituted nitroaniline compound and its application. Background technique [0002] Fluazinam (fluazinam) is a known nitroaniline fungicide, which has shown excellent control of pepper blight, potato late blight, cucumber downy mildew, cucumber gray mold, pear scab and other diseases Effect. [0003] DE3905238, DE4029772 reported that the compound of the following general formula (1) can be used as a fungicide, insecticide, acaricide or nematocide; JP57126476, JP57058667, JP56030963 reported that the compound of the following general formula (2) can be used as an insecticide or Fungicides; JP60064963 reported that the compound of the following general formula (3) is used as a fungicide; JP56065804, US4659363, JP61015877 reported that the compound of the following general formula (4) has insecticidal and bactericidal activity; EP139613, DE3618353, GB2137991 r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/74C07D237/20C07D239/42C07D241/20A01N43/40A01N43/54A01N43/58A01N43/60A01P3/00
Inventor 关爱莹李慧超李志念郝树林兰杰刘长令
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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