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Cyanide-containing diphenylamine compounds and their applications

A technology of cyanodiphenylamine and compounds, which is applied in the field of cyanodiphenylamine-containing compounds, and can solve problems such as unreported structural compounds

Active Publication Date: 2015-10-21
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] 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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  • Cyanide-containing diphenylamine compounds and their applications
  • Cyanide-containing diphenylamine compounds and their applications
  • Cyanide-containing diphenylamine compounds and their applications

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0135] Example 1: Preparation of compound 3

[0136]

[0137] To 1.03g (0.008mol) 2,6-difluoroaniline in 40ml N,N-dimethylformamide solution, add 0.64g (0.016mol) of sodium hydroxide, slowly add 2, 4, 5, 6-Tetrachloro-1,3-phthalonitrile 2.13g (0.008mol), after the addition, continue to stir and react at room temperature for 5h. After the reaction is monitored by TLC, the reaction solution is poured into water, extracted with ethyl acetate, and the organic phase is sequentially After washing with water, washing with saturated brine, drying, filtering, desolventizing, the residue is purified by column chromatography (eluent is ethyl acetate and petroleum ether (boiling range 60-90℃), volume ratio 1:4) to obtain the product 1.65 g, which is compound 3. Light yellow solid, melting point 264-266°C. 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 ) δ (ppm): 6.70 (s, 1H, NH), 7.07 (t, 2H, Ph-3, 5-2H, J=8.1 Hz), 7.37 (m, 1H, Ph-4-1H).

example 2

[0138] Example 2: Preparation of compound 4

[0139]

[0140] First put 0.68g (0.002mol) of compound 3 in 20ml concentrated sulfuric acid solution in an ice bath, slowly add the prepared mixed acid (the amount of nitric acid and sulfuric acid are 0.004mol and 0.006mol, respectively) under stirring, and control the temperature at Below 20°C. After the addition is completed, the reaction is continued for 5 min. After the completion of the reaction as monitored by TLC, the reaction solution is poured into ice water and stirred. After cooling to room temperature, extraction with ethyl acetate, the organic phase was washed with saturated brine, dried, filtered, desolventized, and the residue was column chromatographed (eluents are ethyl acetate and petroleum ether (boiling range 60-90°C), The volume ratio is 1:4) 0.40 g of the product was purified, namely compound 4. Light white solid, melting point 204-206°C. 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 )δ(ppm): 6.70(s, 1...

example 3

[0141] Example 3: Preparation of compound 131

[0142]

[0143] To 10.33g (0.039mol) 4-amino-3,5-dichlorobenzoic acid methyl ester (the preparation method refers to WO2010060379, CN101337940) in 60ml N, N-dimethylformamide solution, add 3.12g sodium hydroxide ( 0.078mol), slowly add 10.37g (0.039mol) of 2,4,5,6-tetrachloro-1,3-phthalonitrile under stirring. After the addition, continue to stir and react at room temperature for 5h. After the reaction is monitored by TLC, The reaction solution was poured into water, extracted with ethyl acetate, the organic phase was washed with water, washed with saturated brine, dried, filtered, desolventized, and the residue was column chromatographed (eluent: ethyl acetate and petroleum ether (boiling range 60- 90°C), the volume ratio is 1:5) 13.65 g of the product, compound 131, was purified. Light yellow solid, melting point 229-231°C. 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 )δ(ppm): 3.96(s, 3H, CH 3 ), 6.92 (s, 1H, NH), 8.11 ...

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Abstract

The invention discloses cyano-diphenylamine-containing compounds or salts thereof. The compounds are represented by a general formula I, wherein substituent groups are defined as in the specifications. The compounds represented by the general formula I have broad-spectrum bactericidal activities in the agricultural field, and have excellent controlling effects against various pathogenic bacteria such as cucumber downy mildew, wheat powdery mildew, maize rust disease, paddy rice blast, cucumber gray mold, and the like. Especially, with relatively low dosages, the compounds still have excellent controlling effects against maize rust disease, paddy rice blast, cucumber gray mold, and cucumber downy mildew. Meanwhile, part of the compounds provided by the invention have good pesticidal activities which can be used in controlling diamond-back moth, aphids, and the like; and / or good herbicidal activities which can be used in controlling green bristlegrass herb, barnyard grass, and the like. Raw materials for synthesizing the compounds are easy to obtain, and the synthesis method is simple. Compared with known bactericidal agents, the compounds have the advantage of low cost and good application prospect.

Description

Technical field [0001] The invention belongs to the field of agricultural sterilization, insecticide and herbicide. Specifically, it relates to a cyano-containing diphenylamine compound and its 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] Patent CN101391981A discloses that the compound represented by the following general formula can be used as an intermediate for synthesizing a new polyhalogenated acridone compound with fluorescence activity and potential drug activity. Among them, compound KC1 (compound code IV-A ), KC2 (Compound Code IV-B), KC3 (Compound Code IV-D), KC4 (Compound Code IV-E), KC5 (Compound Code IV-H), KC6 (Compound Code IV-C), but none Biological activity report; literature Pesticide Science (1988), 24(2), 111-21 reported that com...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/58C07C255/59C07C255/60C07C253/30C07C317/36C07C315/04C07C323/36C07C319/20C07C311/39C07C303/40A01N41/10A01N41/06A01N37/48A01N37/44A01N37/34A01P3/00A01P7/04A01P7/02A01P13/00
CPCA01N37/34A01N37/44A01N37/48A01N41/06A01N41/10
Inventor 刘长令黄光兰杰李慧超李志念郝树林宋玉泉关爱莹崔东亮
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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