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A kind of piperazine benzonitrile compound and application thereof
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A kind of technology of piperazine phthalonitrile and compound, applied in the field of piperazine phthalonitrile compounds, can solve problems such as unreported structural compound
Active Publication Date: 2017-07-21
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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[0009] In the prior art, the structure of the compound shown in the general formula I of the present invention has not been reported
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Embodiment 1
[0224] Example 1: Preparation of tert-butyl 4-(2,3,5-trichloro-4,6-dicyanophenyl)piperazinecarboxylate
[0225]
[0226] To 10.0g (0.054mol) piperazine-1-carboxylic acid tert-butyl ester in 60mL N,N-dimethylformamide solution, add 11.0g (0.081mol) potassium carbonate, and slowly add 2,4,5 under stirring ,6-Tetrachloro-1,3-phthalonitrile 14.4g (0.054mol), 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 Combine, wash with water, wash with saturated brine, dry, filter, desolvate, and purify the residue by column chromatography (eluent is ethyl acetate and petroleum ether (boiling range 60-90℃), volume ratio 1:7) to obtain the product 20.0g, which is tert-butyl 4-(2,3,5-trichloro-4,6-dicyanophenyl)piperazinecarboxylate. Light yellow solid, yield: 89.0%, melting point 185-187°C.
Embodiment 2
[0227] Example 2: Preparation of 2,4,5-3chloro-6-(piperazin-1-yl)isophthalonitrile hydrochloride
[0228]
[0229] Put 5.0g (0.012mol) of tert-butyl 4-(2,3,5-trichloro-4,6-dicyanophenyl)piperazinecarboxylate into a 250mL single-neck bottle, add 50mL of tetrahydrofuran to it, and then 3.7 g (0.036 mol) of concentrated hydrochloric acid was added and reacted at room temperature for 4 hours. After the reaction was monitored by TLC, the solvent was removed under reduced pressure to obtain 3.5 g of white solid, yield: 82.6%.
Embodiment 3
[0230] Example 3: Preparation of Compound 3500
[0231]
[0232] 0.20g (0.0014mol) potassium carbonate was added to the 20mL tetrahydrofuran solution of 0.50g (0.0014mol) of compound II, and 0.27g (0.0019mol) tetrahydrofuran solution containing 0.27g (0.0019mol) methyl iodide was added dropwise with stirring. After the addition, the mixture was stirred at room temperature for 4h. After the reaction was monitored by TLC, the reaction solution was poured into water, extracted with ethyl acetate, the organic phases were combined, washed with saturated brine, dried, and dissolved, and the residue was column chromatographed (eluent: ethyl acetate and petroleum ether (boiling range) 60-90°C), the volume ratio is 1:3) and purified to obtain 0.25 g of the product, namely compound 3500. Yield: 54.2%, melting point 171-173°C.
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Abstract
The invention discloses a piperazine benzene dinitrile compound which is shown as a general formula I. The structural formula is as shown in the specification. In the formula, each substituent group is defined in the specification. The compound of the general formula I has broad spectrum bactericidal activity in the field of agriculture and has excellent effects of controlling multiple pathogenic bacteria such as cucumber downy mildew, wheat powdery mildew, corn rust, rice blast and cucumber gray mold. Particularly, the compound has excellent effects of controlling the cucumber downy mildew and rice blast under low dosage. Moreover, the raw materials for synthesizing the compounds are readily available, and the synthetic method is simple and convenient and has wide application prospects.
Description
Technical field [0001] The invention belongs to the field of agricultural fungicides. Specifically, it relates to a piperazine phthalonitrile compound and its application. Background technique [0002] The document Tetrahedron (2007), 63(45), 10971-10978 discloses the compound represented by the following general formula and compound KC1. The literature only mentions that the compound of the general formula has important biological activity, but there is no report of specific biological activity. [0003] [0004] The literature Tetrahedron (2002), 58(43), 8793-8798 and Tetrahedron Letters (2001), 42(40), 7127-7129 all disclose the compound represented by the following general formula and the following specific compounds KC2, KC3, KC4. [0005] [0006] Patent WO2011048082 discloses compound KC5 with the following structure as a Janus kinase (JAK) inhibitor for the treatment or prevention of immune, inflammatory, autoimmune, allergic disorders and immune-mediated diseases, but ther...
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