Phenoxyquinoline compounds and their preparation methods and applications
A technology of phenoxyquinoline and compound, which is applied in the field of insecticide/acaricide and sterilization to achieve the effect of high biological activity
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Embodiment 1
[0093] Example 1 This example illustrates the preparation of compounds 81 and 82 in Table 1
[0094]
[0095] Synthesis of 2-methyl-4-amino-1-(4-trifluoromethoxyphenoxy)benzene 1) p-trifluoromethoxyphenol (0.10mol), 2-methyl-4-nitrochloride Benzene (0.10mol) and potassium carbonate (0.12mol) were dissolved in N,N-dimethylformamide (DMF, 200mL), stirred at 100-150°C for 8-12h (the reaction was monitored by TLC until complete). Cooled to room temperature, under stirring conditions, the reaction solution was slowly poured into saturated brine, extracted with ethyl acetate, the organic layer was washed with water, dried, and the solvent was removed under reduced pressure to obtain a brown viscous liquid, which was purified to obtain 2-methyl - 25.75 g of 4-nitro-1-(4-trifluoromethoxyphenoxy)benzene. 2) Under reflux and stirring conditions, add 2-methyl-4-nitro-1-(4-trifluoromethoxyphenoxy)benzene (0.05mol) and concentrated hydrochloric acid (0.001mol) to ethanol ( 50 mL) and ...
Embodiment 2
[0098] Example 2 This example illustrates the preparation of compounds 430 and 433 in Table 1
[0099]
[0100] 2,3,5-Trimethyl-6-(4-trifluoromethoxyphenoxy)quinolin-4-ol and 2,3,7-trimethyl-6-(4-trifluoromethoxy Synthesis of phenoxy) quinolin-4-ol 2-methyl-4-amino-1-(4-trifluoromethoxyphenoxy)benzene (0.03mol), 2-methyl-3-oxo Methyl butyrate (0.066mol) and p-toluenesulfonic acid (0.033mol) were refluxed in xylene (120mL) to separate water until the reaction was complete (reaction monitored by TLC). After removing part of the xylene under reduced pressure, a solid precipitated out after cooling, and was suction filtered to obtain 5.61 g of a solid product. It was confirmed by LC-MS analysis that it was 2,3,5-trimethyl-6-(4-trifluoromethoxyphenoxy)quinolin-4-ol and 2,3,7-trimethyl-6- (4-Trifluoromethoxyphenoxy)quinolin-4-ol mixtures.
[0101] 2,3,5-Trimethyl-4-(2-propargyloxy)-6-(4-trifluoromethoxyphenoxy)quinoline (430) and 2,3,7-trimethyl -Synthesis of 4-(2-propargylox...
Embodiment 3
[0103] Example 3 Preparation of 2,3,5-trimethyl-4-(2-propargyloxy)-6-(4-trifluoromethoxyphenoxy)quinoline (430) 10% tall oil
[0104] Take an appropriate amount (10% by weight) of the compound of formula (I) provided by the invention such as compound 430 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 then discharge to get 2,3,5-trimethyl-4-(2-propargyloxy)-6-(4-trifluoro Methoxyphenoxy)quinoline (430) 10% EC.
[0105] Bioassay example
[0106] The compounds of the present invention have been tested for their bacterici...
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