Cyano-diphenylamine-containing compounds and applications thereof

A technology containing cyanodiphenylamine and compounds, which can be used in the fields of agricultural sterilization, herbicides and insecticides, 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

[0009] In the prior art, the structure of the compound shown in th

Method used

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  • Cyano-diphenylamine-containing compounds and applications thereof
  • Cyano-diphenylamine-containing compounds and applications thereof
  • Cyano-diphenylamine-containing compounds and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0135] Example 1: Preparation of Compound 3

[0136]

[0137] To 1.03g (0.008mol) of 2,6-difluoroaniline in 40ml of N,N-dimethylformamide solution, add 0.64g (0.016mol) of sodium hydroxide, slowly add 2,4,5 while stirring, 2.13g (0.008mol) of 6-tetrachloro-1,3-benzenedicarbonitrile. After the addition, continue to stir 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 Washed with water, washed with saturated brine, dried, filtered, precipitated, and the residue was purified by column chromatography (eluent: ethyl acetate and petroleum ether (boiling range 60-90°C), volume ratio: 1:4) to obtain the product 1.65 g, namely compound 3. Pale 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 place 0.68g (0.002mol) of compound 3 in 20ml of concentrated sulfuric acid solution in an ice bath, slowly add the prepared mixed acid (the amounts 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 dropwise addition, the reaction was continued for 5 min. After the reaction was monitored by TLC, the reaction solution was poured into ice water and stirred. After cooling to room temperature, ethyl acetate was extracted, and the organic phase was successively washed with saturated brine, dried, filtered, and desolvated, and the residue was column chromatographed (eluents were ethyl acetate and petroleum ether (boiling range 60-90°C), The volume ratio is 1:4) to obtain 0.40 g of the product, namely compound 4. Light white solid, melting point 204-206°C. 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 )δ (ppm): ...

example 3

[0141] Example 3: Preparation of compound 131

[0142]

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

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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 fields 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 control diseases of fruits and vegetables in storage, and the latter is mainly used to control various diseases of field crops. [0003] Patent CN101391981A discloses that the compound shown in the following general formula can be used as an intermediate for synthesizing a new polyhalogenated acridone compound with fluorescence activity and potential drug activity, wherein 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 without any Biological activity report; literature Pesticide Science (1988), 24 (2), 111-21 reported that compound KC1 (wher...

Claims

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Application Information

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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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