P-dicyanoaniline-containing compounds and applications thereof

A technology of dicyanoaniline and compounds, applied in the fields of insecticide, agricultural fungicide, and herbicide, can solve the problems of 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 th

Method used

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  • P-dicyanoaniline-containing compounds and applications thereof
  • P-dicyanoaniline-containing compounds and applications thereof
  • P-dicyanoaniline-containing compounds and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0167] Example 1: Preparation of Compound I-A-8

[0168]

[0169] Add 0.60 g (0.015 mol) of sodium hydroxide to 1.64 g (0.0075 mol) of 2,6-dichloro-4-nitroaniline in 40 ml of N, N-dimethylformamide solution, and slowly add 2 , 3,5,6-tetrachloro-1,4-benzenedicarbonitrile 2g (0.0075mol), continue to stir at room temperature for 5h after addition, after TLC monitors the reaction is completed, the reaction solution is poured into water, extracted with ethyl acetate , the organic phase was washed successively with water, washed with saturated brine, dried, filtered, and precipitated, and the residue was subjected to column chromatography (the eluent was ethyl acetate and petroleum ether (boiling range 60-90° C.), the volume ratio was 1:4) Purified product 3.1g, namely compound I-A-8. Yellow solid, melting point 156-158°C.

[0170] 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 ), δ (ppm): 6.63 (s, 1H, NH), 8.31 (s, 2H, Ph-3, 5-2H).

example 2

[0171] Example 2: Preparation of Compound I-A-13

[0172]

[0173] Add 0.30 g (0.0075 mol) of sodium hydroxide to 0.7 g (0.0037 mol) of 3-trifluoromethyl-4-cyanoaniline in 40 ml of N, N-dimethylformamide solution, and slowly add 2 , 3,5,6-tetrachloro-1,4-benzenedicarbonitrile 1g (0.0037mol), continue stirring at room temperature for 5h after adding, after TLC monitors that the reaction is complete, the reaction solution is poured into water, and a solid is precipitated, and the Suction filtration to obtain 1.3 g of the product, namely compound I-A-13. Yellow solid, melting point 176-178°C.

[0174] 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 ), δ (ppm): 6.86 (dd, 1H, Ph-6-1H), 7.16 (d, 1H, Ph-2-1H), 7.73 (d, 1H, Ph-5-1H).

example 3

[0175] Example 3: Preparation of Compound I-B-2

[0176]

[0177] Add 0.60 g (0.015 mol) of sodium hydroxide to 1.3 g (0.0075 mol) of 2-amino-5-bromopyridine in 40 ml of N, N-dimethylformamide solution, slowly add 2, 3, 5 , 2g (0.0075mol) of 6-tetrachloro-1,4-benzenedicarbonitrile, after the addition, continue to stir the reaction 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: 1:3) to obtain product 2.5 g, namely compound I-B-2. Yellow solid, melting point 154-156°C.

[0178] 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 ), δ (ppm): 9.78 (s, 1H, NH), 6.62 (d, 1H, Py-3-1H), 7.73 (dd, 1H, Py-4-1H), 8.27 (d, 1H, Py- 6-1H)...

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Abstract

The invention discloses p-dicyanoaniline-containing compounds represented by a general formula I, wherein substituent groups are defined as in the specification. 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 compound containing p-dicyanoaniline 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] WO 9727250 discloses 2-amino-4-(2,4,5-trifluoro-3,6-dicyanophenylamino)benzenesulfonic acid as an intermediate in the synthesis of a dye component, but no biological activity is reported ; Journal of Medicinal Chemistry (1978), 21 (9), 906-13 discloses that numbering is that the compound of 28g has certain anti-inflammatory activity; compound, and reported that the compound has certain activity against related diseases such as grape downy mildew (Plasmopora viticola) at high doses. [0004] [0005] In the prior art, there is ...

Claims

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Application Information

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IPC IPC(8): C07C255/58C07C253/30C07D213/74A01N43/40A01N37/34A01P3/00A01P7/00A01P13/00
CPCA01N43/40A01N37/34
Inventor 郝树林关爱莹兰杰姜艾汝李志念李慧超梁博崔东亮宋玉泉刘长令
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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