Phenoxyl pyrilamine compound and application

A technology of phenoxypyrimidine amines and compounds, which is applied in the field of phenoxypyrimidine amines and can solve the problems that the structure of phenoxypyrimidine amines has not been reported.

Active Publication Date: 2014-05-07
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0030] In the prior art, the structure of the phenoxypyrimidine amine compo...

Method used

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  • Phenoxyl pyrilamine compound and application
  • Phenoxyl pyrilamine compound and application
  • Phenoxyl pyrilamine compound and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0240] Example 1: Preparation of intermediate 4,5-dichloro-6-methylpyrimidine

[0241] 1) Preparation of 4-hydroxy-5-chloro-6-methylpyrimidine

[0242]

[0243] Under stirring at room temperature, to 11.30g (0.11mol) of formamidine acetate in 50ml of methanol was slowly added dropwise 8.80g (0.16mol) of sodium methoxide in methanol, after dripping at room temperature, continue to stir for 2h. Then 11.17g (0.068mol) of the intermediate ethyl 2-chloroacetoacetate was added dropwise to the above solution, and the reaction was stirred at room temperature 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, suction filtration to obtain an orange-yellow solid, the aqueous phase was extracted with (3×50ml) ethyl acetate, dried with anhydrous magnesium sulfate, filtered and desolventized. The residue was dissolved in 50 ml of ethyl acetate, left overnight, and filtered to obtain ...

Embodiment 2

[0247] Example 2: Preparation of intermediate 4-(2-chloro-4-trifluoromethylphenoxy)phenethylamine

[0248] 1) Preparation of 4-(2-chloro-4-trifluoromethylphenoxy)benzeneacetonitrile

[0249]

[0250] Add 25.8g (0.12mol) of 3,4-dichlorotrifluoromethylbenzene, 13.3g (0.1mol) of p-hydroxybenzeneacetonitrile and 27.60g (0.2mol) of potassium carbonate to 150ml of N,N-dimethylformamide After stirring, heat to reflux and react overnight. After the reaction is monitored by TLC, the solvent is evaporated under reduced pressure, and 300ml of ethyl acetate is added for extraction. The organic phase is washed with 5% sodium hydroxide aqueous solution and 50ml saturated brine in turn. After desolvation Column chromatography of the residue (eluent is ethyl acetate and petroleum ether (boiling range 60-90°C), volume ratio 1:4) to obtain 14.55 g of white solid, yield 46.2%, melting point 66.2°C.

[0251] 2) Preparation of 4-(2-chloro-4-trifluoromethylphenoxy)phenethylamine hydrochloride

[0252]

[...

Embodiment 3

[0254] Example 3: Preparation of intermediate 4-(2,6-dichloro-4-nitrophenoxy)phenethylamine hydrochloride

[0255] 1) Preparation of N-Boc-4-hydroxyphenethylamine

[0256]

[0257] Dissolve 11.3g (0.1mol) 4-hydroxyphenethylamine in 80ml tetrahydrofuran, add 10.08g (0.12mol) sodium bicarbonate, 50ml water, 21.80g (0.1mol) di-tert-butyl dicarbonate with stirring at room temperature After dropping the ester, continue the reaction for 4-10 hours. After the reaction is monitored by TLC, the solvent is evaporated under reduced pressure, and (3×50ml) ethyl acetate is added for extraction. The organic phase is washed with 50ml of saturated brine. Chromatography (eluent is ethyl acetate and petroleum ether (boiling range 60-90°C), volume ratio 1:3) to obtain 23.37g of colorless oily liquid, yield 98.6%.

[0258] 2) Preparation of N-Boc-4-(2,6-dichloro-4-nitrophenoxy)phenethylamine

[0259]

[0260] Add 2.10g (0.01mol) N-Boc-4-hydroxyphenethylamine and 2.33g (0.01mol) 3,5-dichloro-4-fluoronitr...

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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 bactericidal insecticides and acaricides, and specifically relates to a novel phenoxypyrimidinamine compound and its use. Background technique [0002] Patent EP0370704 and JP2009161472 disclose the following compound general formula and specific compound CK1 (the numbers in the two patents are compound 47 and compound A respectively), which have bactericidal and insecticidal activities. The compound has now been developed as a commercial bactericide, the common name is fluoxazone (the English common name is diflumetorim). Pesticide Science. 1999, 55: 896-902 also discloses the above compound (numbered as compound 5 in the literature), and the bioassay results show that it has certain activity against wheat rust and barley powdery mildew. [0003] [0004] CK1 (fluoxazone) [0005] The patents JP11012253, JP11049759, and EP0665225 disclose the preparation method of the following compound CK2 (numbered as comp...

Claims

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Application Information

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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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