Di(5-methyl-1,2,3-thiadiazole-4-formoxyl urea) compounds, and preparation method and application thereof
A technology of thiadiazoles and compounds, applied in the field of dual-type compounds, can solve problems such as no biological activity
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Embodiment 1
[0025] Preparation of intermediate 5-methyl-1,2,3-thiadiazole-4-formyl isocyanate II:
[0026] Take a 50 ml three-necked flask, add 3.5 mmoles of 5-methyl-1,2,3-thiadiazole-4-carboxamide I and 10 ml of 1,2-dichloroethane, stir to make the amide in the solvent Disperse evenly in the medium, add dropwise 7.0 mmol of oxalyl chloride diluted with 5 ml of 1,2-dichloroethane with a dropping funnel under ice bath, add dropwise in 30 minutes, then stir at room temperature for 1 hour, and then heat to Reflux at 80°C for 24 hours; after the reaction, the solvent was removed by rotary evaporation to obtain the intermediate 5-methyl-1,2,3-thiadiazole-4-formyl isocyanate II, which was directly used in subsequent reactions without further purification.
Embodiment 2
[0028] Preparation of bis(5-methyl-1,2,3-thiadiazole-4-formylurea) compound IV:
[0029] Add 1.4 mmol of diamine compound H into a 50 mL round bottom flask 2 N-Q-NH 2 III, add 20 ml of 1,2-dichloroethane and stir until the amine compound is completely dissolved, then add 3.5 mmol of 5-methyl-1,2,3-thiadiazole-4-methanol dropwise under stirring Acyl isocyanate II was dissolved in 5 ml of 1,2-dichloroethane solution, and the dropwise addition was completed in 20 minutes. The reaction liquid turned from a red turbid liquid to a light yellow turbid liquid. The reaction system was stirred at room temperature for 3 hours. After the reaction was completed, The reaction mixture was left to stand, and the solid was collected by suction filtration, which was the crude product IV; the filtrate was rotovapped to remove the solvent, and then recrystallized with ethyl acetate and petroleum ether with a volume ratio of 1:3, and the solids were combined and dried to obtain a pure light yello...
Embodiment 3
[0032] The insecticidal activity of two (5-methyl-1,2,3-thiadiazole-4-formylurea) compounds IV of the present invention:
[0033] The synthetic new compound of the present invention is shown in Table 3 to the measuring result of insecticidal activity of diamondback moth and mosquito larvae, and table 3 shows, ZHF-114, ZHF-117, ZHF-120, ZHF-121, ZHF-124, ZHF-128 in The insecticidal activity against Plutella xylostella at a concentration of 400 mg / L was significantly greater than 12.5% of that of the corresponding control agent diflubenzuron. The insecticidal activity of all compounds against Spodoptera litura at a concentration of 400 mg / L was significantly less than 15% of that of the corresponding control agent diflubenzur. The insecticidal activity of all compounds against mosquito larvae at a concentration of 5 mg / L was significantly greater than or equal to 40% of the insecticidal activity of the corresponding control agent diflubenzuron. Therefore, this class of compou...
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