Heterocyclic diamide invertebrate pest control agents
A kind of technology of heteroaromatic ring and benzene ring, applied in the field of preventing and controlling invertebrate pests
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Embodiment 1
[0254] 5-methyl-N-(1-methylethyl)-4-[[4-trifluoromethoxy)benzoyl]amino]-3-pyridinecarbonyl
[0255] Preparation of amines
[0256] Step A: Preparation of ethyl 4-azido-5-methyl-3-pyridinecarboxylate
[0257] Put 14.1 g (78 mmol) of 1,4-dihydro-5-methyl-4-oxo-3-pyridinecarboxylic acid ethyl ester (prepared according to Horvath, G.; Dvortsak, PJHeterocycl.Chem.1980,359) in The slurry in 30 mL of phosphoryl chloride was refluxed for 1 hour. After cooling, use a rotary evaporator to remove volatiles. The residue was poured into cold saturated aqueous sodium bicarbonate solution. Dichloromethane was added and the mixture was filtered through Celite. Separate these layers. The organic layer was dried (sodium sulfate) and the solvent was removed with a rotary evaporator. The residue was dissolved in 150 mL of dimethylformamide. 15.2 g (234 mmol) sodium azide are added. The mixture was heated at 95°C for 1 hour. After cooling, the solvent was removed with a rotary evaporator. The resid...
Embodiment 2
[0269] 1-methyl-N-(1-methylethyl)-5-[[4-trifluoromethoxy)benzoyl]amino]-1H-pyrazole-4-
[0270] Formamide preparation
[0271] Step A: Preparation of 5-amino-1-methyl-N-(1-methylethyl)-1H-pyrazole-4-carboxamide
[0272]1.0g (8.0mmol) of 2-cyano-N-(1-methylethyl)acetamide (prepared according to the method of Cheikh et al. J.Org.Chem., 1991, 56, 970) and 3.1 mL of triethyl Alkyl ortho formate, 5 mL of acetic anhydride and 0.01 g of anhydrous zinc chloride are mixed. The mixture was refluxed for 1 hour. The distillation head was placed on the flask and the reaction was heated at 120°C for 8 hours. After standing for 2 days, the mixture was heated again at 120°C for 12 hours. Use a rotary evaporator to remove the volatiles. Add ethanol and use a rotary evaporator to remove the volatiles again. This material was dissolved in 15 mL ethanol. Add 0.34 mL (6.4 mmol) methylhydrazine. The reaction mixture was refluxed for 5 hours and then allowed to stand overnight at room temperature. Th...
Embodiment 3
[0278] 4-methyl-N-(1-methylethyl)-3-[[4-trifluoromethyl)benzoyl]amino]-2-thiophenecarboxamide
[0279] Preparation
[0280] Step A: 7-Methyl-2H-thieno[3,2-d][1,3]oxazine-2,4(1H)-dione
[0281] Add phosgene-dissolved toluene (4.4g, 20%, 8.88mmol) to the sodium salt of 3-amino4-methyl-thiophene-2-carboxylic acid (1g, 5.58mmol) in water (17mL) at 0°C in. The mixture was heated to room temperature and stirred for 1 hour. The mixture was filtered. After drying under vacuum, 0.49 g (47%) of a solid product was obtained.
[0282] IR(Nujol_)1785, 1696, 1580, 1513, 1236, 988, 918, 848, 826cm -1 .
[0283] 1 H NMR(DMSO-d 6 ) δ 2.20 (s, 3H), 7.88 (s, 1H).
[0284] Step B: 7-Methyl-2-[4-(trifluoromethyl)phenyl)-4H-thieno[3,2-d][1,3]oxazine -4-one
[0285] 4-(Dimethylamino)pyridine (0.66 g, 5.41 mmol) was added to the dioxane (10 mL) in which the product from step A was dissolved. 4-(Trifluoromethyl)benzoyl chloride (1.13 g, 5.42 mmol) was added to the mixture, and the mixture was boiled ...
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