5-n-propyl-4-hydroxypyrrole-2-ketone derivative as well as preparation method and application thereof
A technology of hydroxypyrrole and n-propyl, which is applied in the field of chemistry and pesticides, can solve the problems of high price and high toxicity, and achieve the effect of improved herbicidal activity and obvious activity
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Embodiment 1
[0052] Embodiment 1 Synthesis of eight kinds of 5-n-propyl-4-hydroxypyrrol-2-one derivatives
[0053] 1, Synthesis of 5-acetyl-2,2-dimethyl-1,3-dioxane-4,6-dione (1a)
[0054] Dissolve cycloisopropylidene malonate (1.44g, 10mmol) and DMAP (2.44g, 20mmol) in a 100mL eggplant-shaped flask filled with acetonitrile (20mL) Stirring under the condition of -5°C), acetyl chloride (0.86g, 11mmol) was dissolved in anhydrous acetonitrile (5mL), and added dropwise to the above solution within 1h, and the ice-salt bath was removed after 1h to make it The temperature was gradually returned to room temperature, and the mixture was stirred at room temperature for 16 h, followed by TLC until the end of the reaction. Add 20 mL of 1 mol / L hydrochloric acid to the above mixed solution, stir for 5 min until the solution is clear, remove excess acetonitrile by rotary evaporation, and obtain product 1a after suction filtration. The yield was 83%. Product 1a is characterized as follows: 1 H NMR (...
Embodiment 2
[0094] Example 2 Inhibitory effect of 5-n-propyl-4-hydroxypyrrol-2-one derivatives on weeds
[0095] 1. Pretreatment of the test materials: put the seeds to be tested (purslane, reflexa) into the germination box, add an appropriate amount of distilled water, soak in a constant temperature box at 28°C for 12 hours, filter out the water, and then put them into the germination box. In the germination box, place the seeds in an incubator at 30°C to germinate the seeds until they are white. Accurately weigh 25.00 mg each of atrazine and 2,4-D into a 10 mL centrifuge tube, add a small amount of methanol to it to dissolve, transfer to a 25 mL volumetric flask, dilute to 25 mL, and prepare 1000 mg / L mother liquor for later use.
[0096] 2. Preparation of the compound to be tested: Accurately weigh 25.00 mg of eight kinds of 5-n-propyl-4-hydroxypyrrole-2-one derivatives, add a small amount of methanol to it to dissolve, after dissolving, transfer the solution to a capacity of 25 mL ...
Embodiment 3
[0104] Embodiment 3 compound 3a and 3h control effect on weeds
[0105] The target compounds 3a and 3h with the best germination inhibitory effect were measured at 6 concentrations of 100mg / L, 50mg / L, 10mg / L, 1mg / L, 0.1mg / L and 0.01mg / L, respectively. EC of 3a and 3h on root length inhibition of 2 kinds of weeds 50 value. The results are shown in Table 2.
[0106] EC 50 value
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[0108] According to the measurement results, the drug efficacy was calculated according to the following formula, and the statistical data of the experiment were analyzed by Duncan's new multiple range (DMRT) method. The results are shown in Table 3.
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[0110] In the formula, PT is the number of surviving plants in the treatment area; CK is the number of surviving plants in the blank control area.
[0111] Table 3 target compound 3a and 3h to the control effect of two kinds of weeds pre-emergence and post-emergence (15d after application)
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