Cis-nitenpyram analog containing carboxylic acid-substituted methyl ester and preparation method and application thereof
A technology of nitenpyram and its analogues, which is applied in the field of cis-methalin analogues containing carboxylic acid-substituted methyl esters, its preparation and application, and can solve the problem of insect resistance to nitenpyram photoinstability and Problems such as poor hydrophobicity, to achieve the effects of human and animal safety, shortened reaction time, and good insecticidal activity
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Embodiment 1
[0051] Preparation of (Ia) cis-[3-methylpyridine-4-[(N-6-chloro-3-pyridylmethyl)ethylamino]-5-nitridine-1,2,3,6-tetrahydropyrimidine -1-yl]-tetrahydrofuryl acetate
[0052] Add 20mL tetrahydrofuran methanol to a 100mL three-necked bottle (with a dry lye absorption device), cool in an ice-salt bath to -10°C ~ -15°C, add 3.60mL freshly steamed thionyl chloride dropwise under magnetic stirring, and control the rate of addition Make the reaction temperature not exceed -5°C, react for 1 hour and then naturally warm up to room temperature to obtain a thionyl chloride-tetrahydrofurfuryl alcohol solution. Add 1.60 g of glycine to the thionyl chloride-tetrahydrofurfuryl alcohol solution, heat at 75 to 85° C. for 10 hours, remove the solvent and excess thionyl chloride under reduced pressure, and obtain a black oil, namely glycine tetrahydrofuryl methyl ester hydrochloride ( IIa), directly used in the next reaction without purification.
[0053] Dissolve 2.707g of nitenpyram, 2.347g o...
Embodiment 2
[0059] Preparation of (Ib) cis-[3-methyl-4-[(N-6-chloro-3-pyridylmethyl)ethylamino]-5-nitro-1,2,3,6-tetrahydropyrimidine -1-yl]-propionic acid tetrahydrofuryl methyl ester.
[0060] Add 20mL tetrahydrofuran methanol to a 100mL three-necked bottle (with a dry lye absorption device), cool in an ice-salt bath to -10°C ~ -15°C, add 3.60mL freshly steamed thionyl chloride dropwise under magnetic stirring, and control the rate of addition The reaction temperature was kept below -5°C, and after 1 hour of reaction, the temperature was naturally raised to room temperature to obtain a thionyl chloride-tetrahydrofuran methanol solution. Add 1.85g of β-alanine to a solution of thionyl chloride-tetrahydrofuran, heat at 75-85°C for 6 hours, remove the solvent and excess thionyl chloride under reduced pressure, and obtain a black oily substance, namely β-alanine tetrahydrofuran The methyl ester hydrochloride (IIb) was directly used in the next reaction without purification.
[0061] 2.707g...
Embodiment 3
[0067] Preparation of (Ic) cis-[3-methylpyridine-4-[(N-6-chloro-3-pyridylmethyl)ethylamino]-5-nitridine-1,2,3,6-tetrahydropyrimidine -1-yl]-tetrahydrofurylmethyl butyrate.
[0068] Add 20mL tetrahydrofuran methanol to a 100mL three-necked bottle (with a dry lye absorption device), cool in an ice-salt bath to -10°C ~ -15°C, add 3.60mL freshly steamed thionyl chloride dropwise under magnetic stirring, and control the rate of addition The reaction temperature was kept below -5°C, and after 1 hour of reaction, the temperature was naturally raised to room temperature to obtain a thionyl chloride-tetrahydrofuran methanol solution. Add 1.24g of γ-aminobutyric acid to the methanol solution of thionyl chloride-tetrahydrofuran and heat at 75-85°C for 5 hours, remove the solvent and excess thionyl chloride under reduced pressure to obtain a black oily substance, i.e. γ-aminobutyric acid tetrahydrofuran Methanol hydrochloride (IIc) was directly used in the next reaction without purificat...
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