CN109810062B - A kind of phenylimidazole derivative and its synthetic method and application in pesticide - Google Patents

Abstract

The invention relates to a phenylimidazole derivative, a synthesis method thereof and application thereof in pesticides, in particular to application thereof in fungicide pesticides, belonging to the technical field of pesticides. The invention aims to provide a novel phenylimidazole derivative, a synthetic method thereof and application thereof in pesticides, wherein the structure of the compound is shown as a formula I. The compound has simple and novel structure, easy synthesis and fungicidal activity, and has good bacteriostatic or bactericidal effect on important plant pathogenic fungi such as early blight of tomato, gray mold of tomato, cucumber fusarium wilt, rice blast, rice sheath blight and the like.

Description

A kind of phenylimidazole derivative and its synthetic method and application in pesticide

technical field

The invention relates to a phenylimidazole derivative, a synthesis method thereof and its application in pesticides, especially its application in fungicides and pesticides, and belongs to the technical field of pesticides.

Background technique

Carvacrol and thymol are the main components of many aromatic plant volatile oils and are phenolic monoterpenoids. These compounds have a wide range of biological activities. Studies have found that these compounds have analgesic, anti-inflammatory, anti-arthritis, anti-cancer, anti-diabetic, myocardial protection, gastrointestinal tract protection, liver protection, nerve protection and other biological activities. Sensitive to human antibiotics and resistant to pathogenic bacteria and viruses, inhibiting pathogenic fungi, antiparasitic, insecticidal, bactericidal, antifungal, antioxidant and other biological activities. Therefore, the research on carvacrol and thymol and their derivatives has been very active in recent years.

In recent years, heterocyclic compounds have played an increasingly important role in the research and development of pesticides due to their good selectivity, high activity, low dosage, low toxicity and specificity in the physiological and biochemical reactions of harmful organisms. As one of the most important types of heterocyclic compounds, imidazole compounds have been successfully developed and sold in the field of pesticides and medicines. Due to their special structures and biological activities, imidazole compounds have become the most important research and development in the field of pesticides. Hotspots and Frontiers.

Taking natural active molecules as lead compounds, designing and synthesizing compounds with application prospects is one of the methods for the discovery of new pesticides. In the present invention, imidazole rings are introduced into the structure of natural active substances carvacrol and thymol, some phenylimidazole derivatives are designed and synthesized, and some active compounds or active leading compounds with novel structure and excellent activity are found, which are useful for the creation of new pesticides. A certain foundation has been laid. The phenylimidazole derivatives have bactericidal effect. So far, there is no report on the phenylimidazole derivatives as agricultural fungicides.

SUMMARY OF THE INVENTION

The technical problem to be solved by the present invention is to propose a phenylimidazole derivative with novel structure, excellent activity and bactericidal effect, and a synthesis method thereof, and a method for synthesizing the same, aiming at the deficiencies of limited types, general activity and lack of natural active molecular compounds in the prior art. The application in pesticides lays the foundation for the creation of new pesticides.

In order to solve the above-mentioned technical problem, the present invention provides a kind of phenylimidazole derivative, and its structure is shown in formula I:

Wherein, R ₁ is any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl or neopentyl; R ₂ is any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl or neopentyl; R ₃ is hydrogen, methyl any one of base, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, fluorine, chlorine, bromine, iodine and nitro; R ₄ is hydrogen, methyl any one of base, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, fluorine, chlorine, bromine, iodine and nitro; R ₅ is hydrogen, methyl any one of base, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, fluorine, chlorine, bromine, iodine and nitro; R ₆ is hydrogen, methyl Any of the group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, acetyl group, propionyl group, butyryl group and benzoyl group.

Preferably, the R ₁ is methyl or isopropyl, R ₂ is methyl or isopropyl, R ₃ is any one of hydrogen, methyl, ethyl, fluorine, chlorine or bromine, and R ₄ is any one of hydrogen, methyl, ethyl, fluorine, chlorine or bromine, R ₅ is any one of hydrogen, methyl, ethyl, fluorine, chlorine or bromine, and R ₆ is methyl or ethyl.

As a further preferred scheme, the R ₁ is methyl or isopropyl, R ₂ is methyl or isopropyl, R ₃ is any one of hydrogen, methyl, fluorine or chlorine, R ₄ is hydrogen, Any one of methyl, fluorine or chlorine, R ₅ is any one of hydrogen, methyl, fluorine or chlorine, and R ₆ is methyl or ethyl.

More preferably, the structural formula of the phenylimidazole derivative is one of the following:

。

.

The synthetic method of phenylimidazole derivative of the present invention can be according to chemical synthesis method, and its synthetic technique is as follows:

。

.

The concrete steps of the synthetic method of described phenylimidazole derivative are as follows:

(1) Preparation of raw materials

Take carvacrol, thymol, imidazole and other commercially available chemical reagent raw materials for later use.

(2) Synthetic intermediate I

Add phenol (the phenol is carvacrol or thymol) to the container, dissolve with DMF, add potassium carbonate and halogenated alkane respectively after the dissolution is complete, and stir the reaction at room temperature for 10 h-24 h. The reaction was monitored by TLC. After the reaction was completed, distilled water was added, extracted with ethyl acetate, and the solvent was evaporated under reduced pressure. The obtained product was separated and purified by column chromatography to obtain Intermediate I.

(3) Synthetic intermediate II

After the intermediate I was dissolved in acetic acid and cooled to 0 ℃ in the container, liquid bromine was slowly added dropwise with a constant pressure dropping funnel under stirring. After the dropwise addition, the reaction was raised to room temperature for 6 h. After the reaction was completed, the reaction compound was poured into ice water and extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, evaporated to dryness under reduced pressure, and separated by column chromatography to obtain Intermediate II.

(4) Synthesis of target compounds

Under the protection of _N2 , intermediate II, imidazole, potassium carbonate and cuprous iodide were added to the container, and dissolved in DMF, the reaction system was evacuated and filled with nitrogen, heated to 150°C, and reacted for 40 hours. After the reaction was completed, distilled water was added, extracted with ethyl acetate, the organic phase was dried, evaporated to dryness under reduced pressure, and separated by column chromatography to obtain the target product.

The phenylimidazole derivatives of the present invention can be applied to inhibit or kill phytopathogenic fungi.

The phytopathogenic fungi are tomato early blight, tomato botrytis cinerea, cucumber fusarium wilt, rice blast or rice sheath blight.

In addition, the phenylimidazole derivatives of the present invention can also be used as active ingredients to prepare pesticides, and the pesticides have bactericidal effects. The present invention also provides a pesticide with bactericidal function, the active ingredient of which is the phenylimidazole derivative of the present invention.

Compared with the prior art, the present invention has the following beneficial effects:

The phenylimidazole derivatives of the present invention have simple and novel structures, are easy to synthesize, have bactericidal activity, and are effective against plant pathogens such as tomato early blight, tomato gray mold, cucumber fusarium wilt, rice blast or rice sheath blight. Fungi have good bactericidal effect. The phenylimidazole derivatives have not been reported in the currently known fungicides, which lays a certain foundation for the creation of new pesticides.

Description of drawings

Figure 1 is the structural formula of the phenylimidazole derivatives of the present invention.

Figure 2 shows four typical representations of the structural formula of the phenylimidazole derivatives of the present invention.

Fig. 3 is the synthetic reaction process diagram of the phenylimidazole derivative of the present invention.

Detailed ways

The specific embodiments of the present invention will be described in further detail below, and the technologies or products not specified in the examples are all existing technologies or conventional products that can be obtained by purchasing.

The structure of the phenylimidazole derivatives of the present invention is shown in formula I:

Wherein, R ₁ is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl or neopentyl; R ₂ is methyl, ethyl base, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl or neopentyl; R ₃ is hydrogen, methyl, ethyl, n-propyl, iso- Propyl, n-butyl, isobutyl, tert-butyl, phenyl, fluorine, chlorine, bromine, iodine, nitro; R ₄ is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl base, isobutyl, tert-butyl, phenyl, fluorine, chlorine, bromine, iodine, nitro; R ₅ is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl , tert-butyl, phenyl, fluorine, chlorine, bromine, iodine, nitro; R ₆ is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, Acetyl, propionyl, butyryl, benzoyl.

Its synthetic steps of the synthetic method of phenylimidazole derivatives of the present invention are as follows:

。

.

The application of the phenylimidazole derivatives of the present invention in pesticides is used to inhibit or kill phytopathogenic fungi, and the phytopathogenic fungi to be inhibited or killed are tomato early blight, tomato botrytis cinerea, cucumber fusarium wilt, rice Blast fungus or Rhizoctonia solani.

（C₁₅H₂₀N₂O）的合成。Example 1: Phenylimidazole compound

Synthesis of (C ₁₅ H ₂₀ N ₂ O).

The concrete steps of the synthetic method of this phenylimidazole derivative are as follows:

(1) Synthesis of intermediate 4-isopropyl-3-ethoxytoluene

In a 10 mL round-bottomed flask, 10 mmol of thymol was dissolved in 2 mL of DMF. After the dissolution was complete, 12 mmol of potassium carbonate and 12 mmol of ethyl bromide were added, and the reaction was stirred at room temperature for 15 h. The reaction was monitored by TLC. After the reaction was completed, distilled water was added, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure. The obtained crude product was separated and purified by column chromatography (petroleum ether:ethyl acetate=10:1) to obtain the intermediate 4-isopropyl-3-ethoxytoluene.

(2) Synthesis of intermediate 2-methyl-5-isopropyl-4-ethoxybromobenzene

10 mmol of the intermediate 4-isopropyl-3-ethoxytoluene was dissolved in 20 mL of acetic acid and cooled to 0 °C. After stirring, 11 mmol of liquid bromine was added dropwise with a constant pressure dropping funnel within 20 min. After the dropwise addition was completed, the reaction was raised to room temperature and the reaction was continued for 6 h. The reaction was stopped, the reaction solution was poured into 50 mL of ice water, extracted three times with 30 mL of dichloromethane, the organic phases were combined, the organic phases were dried over anhydrous sodium sulfate, evaporated to dryness under reduced pressure, and separated by column chromatography to obtain Intermediate 2 -Methyl-5-isopropyl-4-ethoxybromobenzene.

(3) Synthesis of target compounds

Under _N2 protection, 10 mmol of intermediate 2-methyl-5-isopropyl-4-ethoxybromobenzene, 15 mmol of imidazole, 20 mmol of potassium carbonate, 2 mmol of cuprous iodide, dissolved in 5 mL of In DMF, evacuated and filled with nitrogen for 3 times, heated to 150° C., and reacted for 40 hours. After the reaction was completed, 30 mL of distilled water was added, extracted three times with 30 mL of ethyl acetate, and the organic phases were combined, dried over anhydrous sodium sulfate, evaporated to dryness under reduced pressure, and separated by column chromatography to obtain the target compound.

Spectral data for the resulting product are as follows: ¹ H NMR (500 MHz, DMSO- d ₆ ) δ 7.73 (t, J = 1.1 Hz, 1H, Ar-H), 7.30 (t, J = 1.3 Hz, 1H, Ar-H ), 7.07 – 7.01 (m, 2H, Ar-H), 6.95 (s, 1H, Ar-H), 4.09 (m, J = 7.0 Hz, 2H, -CH ₂ ), 3.22 (p, J = 6.9 Hz , 1H, -CH), 2.07 (s, 3H, -CH ₃ ), 1.37 (t, J = 6.9 Hz, 3H, -CH ₃ ), 1.16 (d, J = 6.9 Hz, 6H, -CH ₃ ). ¹³ C NMR (125 MHz, DMSO- d ₆ ) δ 155.8, 138.3, 135.2, 132.0, 129.7, 128.9, 124.4, 121.6, 114.4, 64.1, 26.8, 22.8, 17.6, 15.2.

The obtained phenylimidazole derivatives are used for the determination of the antibacterial activity of phytopathogenic fungi as follows:

Tested plant pathogenic fungi: tomato early blight, tomato botrytis cinerea, cucumber fusarium wilt, rice blast, rice sheath blight.

The experimental method adopted: take 5 mg of the compound to be tested, dissolve it in acetone to prepare mother liquors of different concentrations, add the mother liquor to the PDA medium at a ratio of 1%, and obtain a toxic medium with a concentration of 50 ppm after cooling. An equal amount of acetone was added to the PDA medium, which was used as a blank control after cooling. The activated bacterial species to be tested was made into a bacterial cake with a diameter of 5 mm with a hole punch, which was inoculated into the poisoned medium and the blank control medium respectively, and repeated 3 times. All petri dishes were cultured at a constant temperature of 25-26 °C. When the colony diameter of the blank control treatment grew to nearly 8 cm, the colony diameter of each treatment was measured by the cross method, and the inhibition rate of mycelial growth was calculated by the following formula:

Experimental results: Table 1 shows the measurement results of the antibacterial activity of the phenylimidazole derivatives against phytopathogenic fungi.

Table 1 The inhibitory activity of the compound of Example 1 against phytopathogenic fungi at 50 mg·L ^-1

It can be seen from Table 1 that the compound obtained in Example 1 has a good inhibitory effect on Fusarium wilt of cucumber, M. oryzae and Rhizoctonia solani.

（C₁₄H₁₈N₂O）的合成。Example 2: Phenylimidazole compound

Synthesis of (C ₁₄ H ₁₈ N ₂ O).

The concrete steps of the synthetic method of this phenylimidazole derivative are as follows:

(1) Synthesis of intermediate 4-isopropyl-2-methoxytoluene

In a 10 mL round-bottomed flask, 10 mmol of carvacrol was dissolved in 2 mL of DMF. After the dissolution was complete, 12 mmol of potassium carbonate and 12 mmol of methyl iodide were added, and the reaction was stirred at room temperature for 24 h. The reaction was monitored by TLC. After the reaction was completed, distilled water was added, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure. The obtained crude product was separated and purified by column chromatography to obtain the intermediate 4-isopropyl-2-methoxytoluene.

(2) Synthesis of intermediate 5-methyl-2-isopropyl-4-methoxybromobenzene

10 mmol of the intermediate 4-isopropyl-2-methoxytoluene was dissolved in 20 mL of acetic acid and cooled to 0 °C. After stirring, 11 mmol of liquid bromine was added dropwise with a constant pressure dropping funnel within 20 min. After the dropwise addition, the reaction was raised to room temperature and continued for 6 h. Stop the reaction, pour the reaction solution into 50 mL of ice water, extract three times with 30 mL of dichloromethane, combine the organic phases, dry the organic phases with anhydrous sodium sulfate, evaporate to dryness under reduced pressure, and separate by column chromatography to obtain the intermediate 5-Methyl-2-isopropyl-4-methoxybromobenzene.

(3) Synthesis of target compounds

Under _N2 protection, 10 mmol of intermediate 5-methyl-2-isopropyl-4-methoxybromobenzene, 15 mmol of imidazole, 20 mmol of potassium carbonate, 2 mmol of cuprous iodide, dissolved in 5 mL of In DMF, evacuated and filled with nitrogen for 3 times, heated to 150° C., and reacted for 40 hours. After the reaction was completed, 30 mL of distilled water was added, extracted three times with 30 mL of ethyl acetate, and the organic phases were combined, dried over anhydrous sodium sulfate, evaporated to dryness under reduced pressure, and separated by column chromatography to obtain the target compound.

The spectral data of the obtained product are as follows: ¹ H NMR (500 MHz, DMSO- d ₆ ) δ 7.70 (s, 1H, Ar-H), 7.27 (s, 1H, Ar-H), 7.18 – 7.02 (m, 2H, Ar-H), 6.97 (s, 1H, Ar-H), 3.86 (s, 3H, -CH ₃ ), 2.57 – 2.45 (m, 1H, -CH ), 2.13 (s, 3H, -CH ₃ ), 1.13 (d, J = 6.9 Hz, 6H, -CH ₃ ). ¹³ C NMR (125 MHz, DMSO- d ₆ ) δ 158.3, 143.8, 129.2, 127.8, 124.5, 108.2, 56.1, 28.0, 24.2, 15.7.

The obtained phenylimidazole derivatives are used for the determination of the antibacterial activity of phytopathogenic fungi as follows:

Tested plant pathogenic fungi: tomato early blight, tomato botrytis cinerea, cucumber fusarium wilt, rice blast, rice sheath blight.

Using the same experimental method as Example 1, the results of the measurement of the antibacterial activity of the phenylimidazole derivatives against phytopathogenic fungi are obtained as shown in Table 2.

Table 2 The inhibitory activity of the compound of Example 2 against phytopathogenic fungi at 50 mg·L ^-1

It can be seen from Table 2 that the compound of Example 2 has a good inhibitory effect on tomato early blight, tomato botrytis cinerea, cucumber fusarium wilt, rice blast and rice sheath blight.

（C₁₅H₂₀N₂O）的合成。Example 3: Phenylimidazole compound

Synthesis of (C ₁₅ H ₂₀ N ₂ O).

The concrete steps of the synthetic method of this phenylimidazole derivative are as follows:

(1) Synthesis of intermediate 4-isopropyl-2-ethoxytoluene

In a 10 mL round-bottomed flask, 10 mmol of carvacrol was dissolved in 2 mL of DMF. After the dissolution was complete, 12 mmol of potassium carbonate and 12 mmol of ethyl bromide were added, and the reaction was stirred at room temperature for 10 h. The reaction was monitored by TLC. After the reaction was completed, distilled water was added, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure. The obtained crude product was separated and purified by column chromatography (petroleum ether:ethyl acetate=10:1) to obtain the intermediate 4-isopropyl-2-ethoxytoluene.

(2) Synthesis of intermediate 5-methyl-2-isopropyl-4-ethoxybromobenzene

10 mmol of the intermediate 4-isopropyl-2-ethoxytoluene was dissolved in 20 mL of acetic acid and cooled to 0 °C. After stirring, 11 mmol of liquid bromine was added dropwise with a constant pressure dropping funnel within 20 min. After the dropwise addition was completed, the reaction was raised to room temperature and the reaction was continued for 6 h. The reaction was stopped, the reaction solution was poured into 50 mL of ice water, extracted three times with 30 mL of dichloromethane, the organic phases were combined, the organic phases were dried over anhydrous sodium sulfate, evaporated to dryness under reduced pressure, and separated by column chromatography to obtain intermediate 5 -Methyl-2-isopropyl-4-ethoxybromobenzene.

(3) Synthesis of target compounds

Under the protection of _N2 , 10 mmol of intermediate 5-isopropyl-2-methyl-4-ethoxybromobenzene, 15 mmol of imidazole, 20 mmol of potassium carbonate, 2 mmol of cuprous iodide, were dissolved in 5 mL of In DMF, evacuated and filled with nitrogen for 3 times, heated to 150° C., and reacted for 40 hours. After the reaction was completed, 30 mL of distilled water was added, extracted three times with 30 mL of ethyl acetate, and the organic phases were combined, dried over anhydrous sodium sulfate, evaporated to dryness under reduced pressure, and separated by column chromatography to obtain the target compound.

The spectral data of the obtained product are as follows: ¹ H NMR (500 MHz, DMSO- d ₆ ) δ: 7.67 (s, 1H), 7.24 (s, 1H), 7.07 – 7.01 (m, 2H), 6.95 (s, 1H) , 4.12 (m, J = 6.9 Hz, 2H, -CH2), 2.56 – 2.46 (m, 1H, -CH), 2.13 (s, 3H), 1.37 (t, J = 6.9 Hz, 3H), 1.12 (d , J =6.9 Hz, 6H). ¹³ C NMR (125 MHz, DMSO-d ₆ ) δ: 157.5, 143.7, 129.3, 129.0, 127.7, 124.7, 109.2, 64.1, 27.9, 24.2, 15.7, 15.2.

The obtained phenylimidazole derivatives are used for the determination of the antibacterial activity of phytopathogenic fungi as follows:

Tested plant pathogenic fungi: tomato early blight, tomato botrytis cinerea, cucumber fusarium wilt, rice blast, rice sheath blight.

Using the same experimental method as Example 1, the results of the measurement of the antibacterial activity of the phenylimidazole derivatives against phytopathogenic fungi are obtained as shown in Table 3.

Table 3 Inhibitory activity of the compound of Example 3 on phytopathogenic fungi at 50 mg·L ^-1

It can be seen from Table 3 that the compound of Example 3 has a good inhibitory effect on tomato early blight, tomato botrytis cinerea, cucumber fusarium wilt, rice blast, and rice sheath blight.

（C₁₄H₁₈N₂O）的合成。Example 4: Phenylimidazole compound

Synthesis of (C ₁₄ H ₁₈ N ₂ O).

The concrete steps of the synthetic method of this phenylimidazole derivative are as follows:

(1) Synthesis of intermediate 4-isopropyl-3-methoxytoluene

In a 10 mL round-bottomed flask, 10 mmol of carvacrol was dissolved in 2 mL of DMF. After the dissolution was complete, 12 mmol of potassium carbonate and 12 mmol of iodine were added, and the reaction was stirred at room temperature for 24 h. The reaction was monitored by TLC. After the reaction was completed, distilled water was added, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure. The obtained crude product was separated and purified by column chromatography to obtain the intermediate 4-isopropyl-3-methoxytoluene.

(2) Synthesis of intermediate 5-methyl-2-isopropyl-4-methoxybromobenzene

10 mmol of the intermediate 4-isopropyl-3-methoxytoluene was dissolved in 20 mL of acetic acid and cooled to 0 °C. After stirring, 11 mmol of liquid bromine was added dropwise with a constant pressure dropping funnel within 20 min. After the dropwise addition, the reaction was raised to room temperature and continued for 6 h. The reaction was stopped, the reaction solution was poured into 50 mL of ice water, extracted three times with 30 mL of dichloromethane, the organic phases were combined, the organic phases were dried over anhydrous sodium sulfate, evaporated to dryness under reduced pressure, and separated by column chromatography to obtain intermediate 5 -Methyl-2-isopropyl-4-methoxybromobenzene.

(3) Synthesis of target compounds

Under _N2 protection, 10 mmol of intermediate 2-isopropyl-5-methyl-4-methoxybromobenzene, 15 mmol of imidazole, 20 mmol of potassium carbonate, 2 mmol of cuprous iodide, dissolved in 5 mL of In DMF, evacuated and filled with nitrogen for 3 times, heated to 150° C., and reacted for 40 hours. After the reaction was completed, 30 mL of distilled water was added, extracted three times with 30 mL of ethyl acetate, and the organic phases were combined, dried over anhydrous sodium sulfate, evaporated to dryness under reduced pressure, and separated by column chromatography to obtain the target compound.

The spectral data of the obtained product are as follows: ¹ H NMR (500 MHz, DMSO- d ₆ ) δ: 7.73 (s, 1H, Ar-H), 7.30 (s, 1H, Ar-H), 7.05 (d, J = 6.7 Hz, 2H, Ar-H), 6.97 (s, 1H, Ar-H), 3.84 (s, 3H, -CH ₃ ), 3.21 (p, J = 6.9 Hz, 1H, -CH), 2.08 (s, 3H, -CH ₃ ), 1.15(d, J = 7.0 Hz, 6H, -CH ₃ ). ¹³ C NMR (125 MHz, DMSO-d ₆ ) δ: 156.5, 138.3, 135.0, 132.1, 129.7, 128.9, 124.4 , 121.6, 113.5, 56.3, 26.5, 22.8, 17.7.

The obtained phenylimidazole derivatives are used for the determination of the antibacterial activity of phytopathogenic fungi as follows:

Tested plant pathogenic fungi: tomato early blight, tomato botrytis cinerea, cucumber fusarium wilt, rice blast, rice sheath blight.

Using the same experimental method as in Example 1, the results of the measurement of the antibacterial activity of the phenylimidazole derivatives against phytopathogenic fungi are obtained as shown in Table 4.

Table 4 Inhibitory activity of the compound of Example 4 against phytopathogenic fungi at 50 mg·L ^-1

It can be seen from Table 4 that the compound of Example 4 has a good inhibitory effect on tomato early blight, tomato botrytis cinerea, cucumber fusarium wilt, rice blast, and rice sheath blight.

The technical content of the present invention has been described above, but the protection scope of the present invention is not limited to the content, within the scope of knowledge possessed by those of ordinary skill in the art, the present invention can also be reviewed without departing from the purpose of the present invention. Various changes are made to the technical content of the present invention, and any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention shall be included within the protection scope of the present invention.

Claims (4)

1. A phenylimidazole derivative is characterized in that the structure of the phenylimidazole derivative is shown as a formula I:

the structural formula of the phenylimidazole derivative is one of the following formulas:

2. a method for synthesizing a phenylimidazole derivative according to claim 1, which comprises: the synthesis steps of the phenylimidazole derivative are as follows:

the synthesis method comprises the following specific steps:

2.1 preparation of the starting Material

Taking carvacrol, thymol and imidazole as chemical reagent raw materials sold in markets for standby;

2.2 Synthesis of intermediate I

Adding carvacrol or thymol into a container, dissolving with DMF, respectively adding potassium carbonate and halogenated alkane after complete dissolution, and stirring at room temperature for reaction for 10-24 h; monitoring the reaction by TLC, adding distilled water after the reaction is finished, extracting by using ethyl acetate, evaporating the solvent under reduced pressure, and separating and purifying the obtained product by column chromatography to obtain an intermediate I;

2.3 Synthesis of intermediate II

Dissolving the intermediate I in acetic acid in a container, cooling to 0 ℃, slowly dropwise adding liquid bromine by using a constant-pressure dropping funnel while stirring, and heating the reaction to room temperature after dropwise adding is finished to continue reacting for 6 hours; after the reaction is finished, pouring the reaction compound into ice water, extracting with dichloromethane, drying an organic phase with anhydrous sodium sulfate, then evaporating to dryness under reduced pressure, and separating by column chromatography to obtain an intermediate II;

2.4 Synthesis of the target Compound

N₂Under protection, adding the intermediate II, imidazole, potassium carbonate and cuprous iodide into a container, dissolving with a solvent DMF, vacuumizing a reaction system, filling nitrogen, and addingHeating to 150 ℃, and reacting for 40 hours; and adding distilled water after the reaction is finished, extracting with ethyl acetate, drying an organic phase, evaporating to dryness under reduced pressure, and separating by column chromatography to obtain a target product.

3. Use of the phenylimidazole derivatives according to claim 1 or 2 in pesticides characterized in that: the phenylimidazole derivatives are useful for inhibiting or killing phytopathogenic fungi.

4. The use of phenylimidazole derivatives according to claim 3 in pesticides, characterized in that: the plant pathogenic fungi are early blight of tomato, gray mold of tomato, cucumber fusarium wilt, rice blast or rice sheath blight.

Images