3-Methoxypyrazole amide compound and its application
A technology of methoxypyrazole amide and compound, applied in the field of 3-methoxy pyrazole amide compound, can solve the problem that the insecticidal activity of 3-methoxy pyrazole amide compound is not disclosed and the like
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example 1
[0074] The preparation of example 1, compound 1
[0075] (1), the synthesis of 3-chloro-2-hydrazinopyridine
[0076]
[0077] Add 2,3-dichloropyridine (50 g, 0.34 mol) and tetrahydrofuran (500 ml) into a 1000 ml reaction flask, and add hydrazine hydrate (106 g, 1.69 mol) dropwise at 40° C. for 3 hours. Continue to react for 10 hours until the reaction is complete. The pH value of the reaction solution was adjusted to 8-9 with saturated sodium bicarbonate solution, the tetrahydrofuran was evaporated under reduced pressure, and a solid precipitated out, and 36 g of an off-white solid was obtained by filtration, with a yield of 74% and a melting point of 167-170°C.
[0078] 1 H NMR (300MHz, DMSO-d 6 ): 8.12 (dd, 1H), 7.85 (dd, 1H), 6.83 (dd, 1H).
[0079] (2), the synthesis of 1-(3-chloropyridin-2-yl)-3-pyrazolidinone-5-carboxylic acid ethyl ester
[0080]
[0081] Add 100 ml of absolute ethanol and sodium ethylate (5.1 g, 76 mmol), 3,5-dichloro-2-hydrazinopyridine (10...
example 2
[0102] Example 2, the preparation of compound 28
[0103] (1), 3, the synthesis of 5-dichloro-2-hydrazinopyridine
[0104]
[0105] Add 2,3,5-trichloropyridine (20 grams, 0.11 moles), 80% hydrazine hydrate (34 grams, 0.55 moles) and 200 milliliters of dioxane successively in a 100 milliliter reaction flask, and stir at reflux temperature for 20 hours . The reaction liquid was cooled overnight, white crystals were precipitated, filtered, and dried to obtain 14 g of solid, yield: 72%, melting point: 187-189°C.
[0106] 1 H NMR (300MHz, DMSO-d 6 ): 8.12(d, 1H), 7.84(d, 1H).
[0107] (2), the synthesis of 1-(3,5-dichloropyridin-2-yl)-3-pyrazolidinone-5-carboxylic acid ethyl ester
[0108]
[0109] Add 150 ml of absolute ethanol and sodium ethylate (4.1 g, 61 mmol), 3,5-dichloro-2-hydrazinopyridine (10 g, 56 mmol) in a 500 ml reaction flask, and the mixture is heated to reflux for 5 minutes , diethyl maleate (10 g, 61 mmol) was added dropwise. Heating to reflux was con...
example 3
[0130] Example 3, the preparation of compound 29
[0131] (1), 2-(3-methoxy-1-(3,5-dichloropyridin-2-yl)-1H-5-pyrazolyl)-6-cyano-8-chloro-4H-benzene Preparation of [d][1,3]oxazin-4-one
[0132]
[0133]Add methanesulfonyl chloride (0.23 g, 1.98 mmol) and acetonitrile (5 ml) to a 100 ml three-necked flask, and add 1-(3,5-dichloropyridin-2-yl)-3-methoxy Base-1H-pyrazole-5-carboxylic acid (0.52 g, 1.80 mmol. See Example 2, step (5) for its preparation) and triethylamine (0.18 g, 1.80 mmol) in acetonitrile (5 ml), 10 Minutes drop, react for 1 hour, add 3-chloro-5-cyano-2-aminobenzoic acid (0.35 g, 1.80 mmol) to the reaction system, the solution is brown, stir for 30 minutes, drop triethylamine (0.36 g, 3.60 mmol) in acetonitrile (5 ml), a yellow solid was generated, stirred for 1 hour, then added methanesulfonyl chloride (0.23 g, 1.98 mmol) in acetonitrile (5 ml), the solution was yellow , a large amount of solids were formed, reacted for 1 hour, then added dropwise a soluti...
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