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N-aryloxy/thiobenzyl difluoromethyl pyrilamine compound as well as preparation method and application thereof

A technology of thiobenzyldifluoromethylpyrimidinamine and compounds, which is applied in the fields of botany equipment and methods, applications, organic chemistry, etc., can solve the problem that the bactericidal activity of the compound has not been reported, and the insecticidal and acaricidal activities are far inferior to others. question

Pending Publication Date: 2022-05-20
湖南海利常德农药化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Pyrimidine amine compounds have broad-spectrum biological activity. CN201610954548.9 discloses the biologically active pyrimidine amine compounds represented by formula (D), and reports the N-aryloxybenzyl alkyl pyrimidine amine compounds represented by D1 (compound I5 in the specification) and N-aryloxybenzyltrifluoromethylpyrimidine amine compound shown in D2 (compound I14 in the specification), the data disclosed in CN201610954548.9 shows that D1 has good insecticidal and acaricidal activity , the insecticidal and acaricidal activity of D2 is far less than that of D1; the bactericidal activity of the compound in CN201610954548.9 has not been reported

Method used

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  • N-aryloxy/thiobenzyl difluoromethyl pyrilamine compound as well as preparation method and application thereof
  • N-aryloxy/thiobenzyl difluoromethyl pyrilamine compound as well as preparation method and application thereof
  • N-aryloxy/thiobenzyl difluoromethyl pyrilamine compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] Example 1 This example illustrates the preparation method of compound 02 in Table 1

[0091]

[0092]

[0093] 4-(4-methylphenoxy)benzonitrile p-cresol (0.10mol), 50% aqueous potassium hydroxide solution (11.20g) and toluene (100mL) were heated under stirring to remove toluene and water to obtain 4- Methylphenol potassium salt. Add N,N-dimethylformamide (100 mL), p-bromobenzonitrile (0.10 mol) and cuprous bromide (0.012 mol), and react under stirring and reflux for 2-5 h until the reaction is complete. The reaction solution was slowly poured into ice water with stirring, and the resulting solid was filtered and recrystallized with 95% ethanol to obtain 15.60 g of the title compound as an off-white solid.

[0094] 4-(4-methylphenoxy)benzylamine under nitrogen protection, 4-(4-methylphenoxy)benzonitrile (0.06mol), tetrahydrofuran (150mL) and sodium borohydride (0.12mol), in Under the condition of stirring and reflux, react for 6-20h until the reaction is complete....

Embodiment 2

[0099] Embodiment 2 This embodiment illustrates the preparation method of compound 83 in Table 1

[0100]

[0101]Add sodium methoxide dropwise to a solution of acetamidine hydrochloride (0.33mol) and methanol (50mL) at 5-10°C with stirring (0.63mol) in 30% methanol solution, continue to stir for 2-3h after dropping, add 2-chloro-3-oxo-4,4-difluorobutanoic acid ethyl ester dropwise, let it warm up to room temperature to complete the reaction. After methanol was removed, ethyl acetate was added, insoluble matter was filtered off, and the filtrate was concentrated to obtain 32.90 g of the title product as a yellow solid, which was directly used in the next reaction.

[0102] 4,5-dichloro-2-methyl-6-difluoromethylpyrimidine at 0~5℃ under the condition of stirring, 5-chloro-2-methyl-6-difluoromethylpyrimidin-4-ol (0.15mol) was added in batches to phosphorus oxychloride (0.35mol), and after complete dissolution, triethylamine (0.17mol) was added dropwise. Naturally warm up to ...

Embodiment 3

[0105] Example 3 Preparation of 5-chloro-6-difluoromethyl-N-(4-(4-methylphenoxy)benzyl)pyrimidin-4-amine (02) 10% emulsifiable concentrate

[0106] Take an appropriate amount (10% by weight) of the compound of formula (I) provided by the invention such as compound 02 in Table 1, an appropriate amount of cosolvent (such as ethyl acetate or acetone), an appropriate amount of pesticide auxiliary agent and solvent (such as Toluene) etc. into the reactor, first add a certain amount of solvent (such as toluene) and defoamer and stir for 10-30 minutes, then add an appropriate amount of stabilizer, synergist, penetrating agent and other components, continue stirring for 10-30 minutes , adjust the pH value, then put an effective amount of solvent into the kettle, stir evenly and discharge to get 5-chloro-6-difluoromethyl-N-(4-(4-methylphenoxy)benzyl) Pyrimidin-4-amine (02) 10% EC.

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Abstract

The invention discloses an N-aryloxy / thiobenzyl difluoromethyl pyrimidinamine compound as shown in a formula (I) as well as a preparation method and application of the N-aryloxy / thiobenzyl difluoromethyl pyrimidinamine compound. R, R1, R2, R3, W, m and n in the formula are defined in the specification. The compound shown in the formula (I) has insecticidal / acaricidal and / or bactericidal biological activity, and especially has very high activity on diseases such as powdery mildew and rust disease.

Description

technical field [0001] The invention belongs to the field of insecticide / mite and bactericide, and in particular relates to N-aryloxy / thiobenzyl difluoromethylpyrimidinamine compounds with insecticide / mite and bactericidal biological activity, a preparation method thereof, and a compound containing said compound Insecticide / mite, fungicide composition, and use and method of using these compounds to control pests / mite and harmful germs. Background technique [0002] The control of pests / mites and harmful germs is very important in achieving efficient agricultural processes. The control of pests / mite and harmful bacteria is also very important in the fields of forestry, animal husbandry, sideline, fishery and public health. Although there are many pest / mite and harmful bacteria control agents on the market, due to the continuous expansion of the market, foreign pests / mite and harmful bacteria, resistance of pests / mite and harmful bacteria, drug service life, drug economy and ...

Claims

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Application Information

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IPC IPC(8): C07D239/42A01N43/54A01P7/04A01P7/02A01P3/00
CPCC07D239/42A01N43/54Y02A50/30
Inventor 彭长春柳爱平杨自力任叶果李建明杨小龙柳孜王琴刘民华冯蛟龙
Owner 湖南海利常德农药化工有限公司
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