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Phenoxypyrimidine amine compounds and their uses

A phenoxypyrimidinamine and compound technology, applied in the field of phenoxypyrimidinamine compounds, can solve problems such as unreported structural phenoxypyrimidinamine compounds

Active Publication Date: 2015-09-09
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0028] In the prior art, the structure of the phenoxypyrimidine amine compounds shown in the general formula I of the present invention has not been reported

Method used

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  • Phenoxypyrimidine amine compounds and their uses
  • Phenoxypyrimidine amine compounds and their uses
  • Phenoxypyrimidine amine compounds and their uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0241] Embodiment 1: the preparation of intermediate 4,5-dichloro-6-methylpyrimidine

[0242] 1) Preparation of 4-hydroxyl-5-chloro-6-methylpyrimidine

[0243]

[0244] Slowly add 8.80 g (0.16 mol) of sodium methoxide in methanol solution dropwise to 11.30 g (0.11 mol) of formamidine acetate in 50 ml of methanol under stirring at room temperature, and continue stirring at room temperature for 2 h after dropping. Then, 11.17 g (0.068 mol) of intermediate ethyl 2-chloroacetoacetate was added dropwise to the above solution, and the stirring reaction at room temperature was continued for 5-7 hours. After the reaction was monitored by TLC, the solvent was evaporated under reduced pressure, and the pH was adjusted to 5 with hydrochloric acid. ~6, the orange solid was obtained by suction filtration, and the aqueous phase was extracted with (3×50ml) ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and precipitated. The residue was dissolved in 50ml of ethyl acetate...

Embodiment 2

[0248] Embodiment 2: the preparation of intermediate 4-(2-chloro-4-trifluoromethylphenoxy) phenethylamine

[0249] 1) Preparation of 4-(2-chloro-4-trifluoromethylphenoxy)phenylacetonitrile

[0250]

[0251] Add 25.8g (0.12mol) of 3,4-dichlorotrifluoromethylbenzene, 13.3g (0.1mol) of p-hydroxyphenylacetonitrile and 27.60g (0.2mol) of potassium carbonate into 150ml of N,N-dimethylformamide, Heated to reflux under stirring, reacted overnight, after the reaction was monitored by TLC, the solvent was evaporated under reduced pressure, 300ml of ethyl acetate was added for extraction, the organic phase was washed successively with 5% aqueous sodium hydroxide solution and 50ml of saturated saline, and the remaining Column chromatography (eluent: ethyl acetate and petroleum ether (boiling range 60-90°C), volume ratio: 1:4) gave 14.55 g of white solid, yield 46.2%, melting point 66.2°C.

[0252] 2) Preparation of 4-(2-chloro-4-trifluoromethylphenoxy)phenethylamine hydrochloride

[...

Embodiment 3

[0255] Embodiment 3: the preparation of intermediate 4-(2,6-dichloro-4-nitrophenoxy) phenethylamine hydrochloride

[0256] 1) Preparation of N-Boc-4-hydroxyphenethylamine

[0257]

[0258] Dissolve 11.3g (0.1mol) of 4-hydroxyphenethylamine in 80ml of tetrahydrofuran, add 10.08g (0.12mol) of sodium bicarbonate and 50ml of water in turn, and add 21.80g (0.1mol) of di-tert-butyl dicarbonate dropwise under stirring at room temperature After dropping the ester, continue to react for 4-10 hours. After the reaction is monitored by TLC, evaporate the solvent under reduced pressure, add (3×50ml) ethyl acetate for extraction, and wash the organic phase with 50ml of saturated brine. Chromatography (eluent: ethyl acetate and petroleum ether (boiling range: 60-90°C), volume ratio: 1:3) gave 23.37 g of a colorless oily liquid with a yield of 98.6%.

[0259] 2) Preparation of N-Boc-4-(2,6-dichloro-4-nitrophenoxy)phenethylamine

[0260]

[0261] Add 2.10g (0.01mol) N-Boc-4-hydroxyphen...

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Abstract

The invention discloses a phenoxyl pyrilamine compound which has a structural general formula I as shown in the specification, wherein definitions of substituents in the formula are as shown in the specification. The compound has broad-spectrum bactericidal, insecticidal and acaricidal activity, has excellent prevention and control effects on diamondback moths, armyworms, myzus persicae and tetranychus cinabarinus boisdu, and particularly has the better prevention effect on the myzus persicae and the tetranychus cinabarinus boisdu. The compound shows the good bactericidal activity at the same time, and a part of the compound has the excellent prevention and control effects on diseases such as cucumber downy mildew, wheat powdery mildew, puccinia sorghi and rice blast at a very low dose.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides, insecticides and acaricides, and specifically relates to a novel phenoxypyrimidine amine compound and its application. Background technique [0002] Patents EP0370704 and JP2009161472 disclose the following compound formula and specific compound CK1 (numbers in the two patents are respectively compound 47 and compound A), which have bactericidal and insecticidal activities. The compound has been developed into a commercialized fungicide with the common name of fluoxanstrobin (English common name diflumetorim). Pesticide Science.1999, 55: 896-902 also discloses the above-mentioned compound (numbered as compound 5 in the literature), and bioassay results show that it has certain activity against wheat rust and barley powdery mildew. [0003] [0004] Patents JP11012253, JP11049759, and EP0665225 disclose the preparation method of the following compound CK2 (numbered as compound 7 in JP110...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/42A01N43/54A01P3/00A01P7/04A01P7/02
CPCA01N43/54C07D239/42
Inventor 刘长令王立增宋玉泉孙旭峰兰杰张金波冯聪柴宝山孙芹王斌刘少武
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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