Substitute 2,3-dihydrogen thiazole [4,5-d] pyrimidine-7(6H)- ketone (imines) having weed removal active and preparation thereof
The technology of dihydrothiazole and pyrimidine is applied in the field of substituted 2,3-dihydrothiazolo[4,5-d]pyrimidin-7(6H)-one (imine) with herbicidal activity and its preparation. Solve problems such as many steps, few reports on pesticide activity, and harsh conditions
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Embodiment 1
[0035] Preparation of Compound 1, Method A,
[0036] In a dry round-bottomed flask, add 1 mmol of phosphinimine, then add 15 ml of anhydrous dichloroethane to dissolve, add 1.1 mmol of phenyl isocyanate dropwise, and after standing at 10°C for 6 hours, add 1.1 One millimole of n-diethylamine, stirred and reacted for 1 hour, after the reaction was complete, removed most of the solvent under reduced pressure, then added 15 milliliters of absolute ethanol and 0.6 mmol of sodium alkoxide solution, and stirred and reacted for 12 hours at a temperature below 15°C. Precipitation was precipitated, filtered, and recrystallized with dichloroethane / petroleum ether to obtain the pure product of the target compound as a light yellow solid with a yield of 73.6%. M.p.206.2~207.1℃;
[0037] Elemental analysis (%): Calculated value (C 21 h 20 N 4 OS 2 ):: C, 61.74; H, 4.93; N, 13.71; S, 15.70; Found: C, 61.31; H, 5.01; N, 13.50; S, 15.23;
[0038] IR(υ / cm -1 ): 2974 (C-H), 1687 (C=O),...
Embodiment 2
[0066] Preparation of compound 3
[0067] In a dry round-bottomed flask, add 1 mmol of phosphinimine, then add 15 ml of anhydrous chloroform to dissolve, add 1.2 mmol of phenyl isocyanate dropwise, react at below 50°C for 24 hours, then add 1.2 mmol of Diisopropylamine, stirred and reacted for 24 hours. After the reaction was complete, removed most of the solvent under reduced pressure, then added 15 ml of anhydrous isopropanol and 1.0 mmol of pyridine solution, and stirred and reacted for 8 hours below 20°C. Precipitated, filtered, and recrystallized with chloroform / petroleum ether to obtain the pure product of the target compound as light yellow crystals, with a yield of 77.8%, m.p.254.1-255.6°C;
[0068] 1 H NMR (400MHz CDCl 3 ): δ (ppm): 0.82 (d, J=6.4, 12H, 4CH 3 ), 3.49 (m, 2H, 2CH), 7.25-7.58 (m, 10H, Ph-H);
[0069] IR(KBr)υ(cm -1 ): 2962 (C-H), 1689 (C=O), 1571, 1525 (Ph);
[0070] Elemental analysis (%). Calculated value (C 23 h 24 N 4 OS 2 :): C, 63.27; ...
Embodiment 3
[0103] Preparation of Compound 11
[0104] In a dry round-bottomed flask, add 1 mmol of phosphinimine, then add 15 ml of anhydrous ether to dissolve, add 0.9 mmol of p-chlorophenylisocyanate dropwise, and let it stand for reaction below -20°C for 12 hours, then add 1.0 mmol of diisopropylamine, stirred for 24 hours, after the reaction was complete, removed most of the solvent under reduced pressure, then added 15 ml of anhydrous n-propanol and 0.9 mmol of diethylamine solution, stirred below 0°C After reacting for 6 hours, a precipitate was precipitated, filtered, and recrystallized with dichloromethane / petroleum ether to obtain the pure product of the target compound as white crystals, with a yield of 79.7%, m.p.>270°C.
[0105] 1 H NMR (400MHz CDCl 3 ): δ (ppm): 0.85 (d, J=6.4, 12H, 4CH 3 ), 3.47(m, 2H, 2CH), 7.22-7.60(m, 9H, Ph-H);
[0106] IR(KBr)υ(cm -1 ): 2981 (C-H), 1675 (C=O), 1570, 1529 (Ph);
[0107] Elemental analysis (%). Calculated value (C 23 h 23 ClN ...
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