Substituted isoxazoline compound and pest control agent
A compound, isoxazoline technology, applied in the direction of heterocyclic compound active ingredients, plant growth regulators, biocides, etc., can solve problems such as unknown usefulness of pest control agents
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[0610] Hereinafter, the present invention will be described in more detail by specifically describing synthesis examples and test examples of the compounds of the present invention as Examples, but the present invention is not limited thereto.
Synthetic example 1
[0613] N-[2-Chloro-4-[5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]phenyl]methanol -2-(methylthio)acetamide (Compound No. 1-005 of the present invention).
[0614] Step 1: Production of 3-chloro-4-methylbenzaldehyde oxime
[0615] To a solution of 5.0 g of 3-chloro-4-methylbenzaldehyde in 40 ml of methanol and 30 ml of water was added 4.7 g of hydroxylamine hydrochloride, followed by stirring at room temperature for 2 hours. After the reaction was finished, the reaction mixture was diluted with 70ml of ethyl acetate and washed with water (30ml×1), dehydrated and dried with saturated brine and anhydrous sodium sulfate successively, and the solvent was distilled off under reduced pressure to obtain the target product as white crystals. Compound 5.1g. The target product was directly used in the next step without further purification.
[0616] Melting point 66.0~68.0℃
[0617] 1 H NMR (CDCl 3 , Me 4 Si, 300MHz) δ8.12(bs, 1H), 8.07(s, 1H), 7.56(s, 1H)...
Synthetic example 2
[0633] N-[1-[4-[5-[3,5-bis(trifluoromethyl)phenyl]-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]phenyl ]ethyl]-2-(methylthio)acetamide (Compound No. 1-001 of the present invention).
[0634] Step 1: Production of 5-[3,5-bis(trifluoromethyl)phenyl]-3-(4-ethylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole
[0635] To a solution of 1.49 g of 4-ethylbenzaldoxime in 10 ml of N,N-dimethylformamide was added 1.60 g of N-chlorosuccinimide, followed by stirring at room temperature for 2 hours. Next, 3.00 g of 3,5-bis(trifluoromethyl)-1-(1-trifluoromethylvinyl)benzene and 3.00 g of potassium bicarbonate were added to the reaction mixture, and stirring was continued at room temperature for 14 hours. . After the reaction was completed, 10 ml of water was added to the reaction mixture and extracted with ethyl acetate (50 ml × 1), the organic layer was washed with 20 ml of water, then dehydrated with saturated brine, anhydrous sodium sulfate, dried, and distilled under reduced pressure. So...
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