CN109232536B - 2, 4-diphenyl substituted imidazole compound and application of suspending agent thereof in preventing and treating wheat sharp eyespot - Google Patents

2, 4-diphenyl substituted imidazole compound and application of suspending agent thereof in preventing and treating wheat sharp eyespot Download PDF

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CN109232536B
CN109232536B CN201811192913.2A CN201811192913A CN109232536B CN 109232536 B CN109232536 B CN 109232536B CN 201811192913 A CN201811192913 A CN 201811192913A CN 109232536 B CN109232536 B CN 109232536B
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substituted imidazole
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李勇
李昊昱
苗永辉
杨俊皓
金敏
庞党伟
王振林
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Shandong Agricultural University
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    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
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Abstract

The invention discloses a 2, 4-diphenyl substituted imidazole compound shown in a formula I or pharmaceutically acceptable salt thereof,

Description

2, 4-diphenyl substituted imidazole compound and application of suspending agent thereof in preventing and treating wheat sharp eyespot
Technical Field
The invention relates to the field of agricultural bactericides, in particular to 2, 4-diphenyl substituted imidazole compounds and application of a suspending agent thereof in preventing and treating wheat sharp eyespot.
Background
Sheath blight of wheat is a serious soil-borne fungal disease mainly caused by rhizoctonia cerealis, and mainly occurs on leaf sheaths and stalks of wheat. The infected wheat has the symptoms of rotten buds, withered diseased seedlings, rotten stalks of flowers and stalks, withered white ears and the like in each growth stage. The sheath blight of wheat almost spreads in various temperate wheat planting areas of the world, the high yield and the stable yield of wheat are seriously influenced, and great economic loss is easily caused. With the increase of climate warming, the application amount of chemical fertilizers, particularly nitrogen fertilizers, and the advance of wheat seeding period and the increase of seeding amount, wheat sharp eyespot commonly occurs in wheat areas in China since the 80 s of the 20 th century. In the 90 s of the 20 th century, the occurrence of wheat sharp eyespot is in a trend of increasing year by year, and the high and stable yield of wheat is seriously threatened.
At present, common chemical agents for preventing and treating wheat sheath blight comprise validamycin, thifluzamide, tebuconazole, hexaconazole, diniconazole, epoxiconazole, propiconazole, benzyl-propiconazole and the like, but the defects of the common agents are still very obvious. For example, validamycin is an aminoglycoside antibiotic, and has potential toxic effects on human ears and kidneys. The benzyl-propiconazole has no harm to the seedling stage of wheat, but cannot be used together with a herbicide fluroxypyr; the water demand of the thifluzamide is large; triazoles such as tebuconazole, hexaconazole, diniconazole, epoxiconazole and propiconazole have an adverse effect on the germination of wheat.
The 2, 4-diphenyl substituted imidazole compound provided by the invention has no report on the research on the aspect of preventing and treating the wheat sharp eyespot, and provides a new research direction for preventing and treating the wheat sharp eyespot without influencing the germination and seedling emergence of wheat.
Disclosure of Invention
The invention provides a 2, 4-diphenyl substituted imidazole compound, which has a structure shown in a formula I:
Figure BDA0001828026110000021
wherein Ar is selected from the group consisting of 7-isoquinolinyl, 6-isoquinolinyl, 7-quinolyl, 6-quinolyl, 2-quinolyl, 3-isoquinolyl, 3-quinolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidyl, 4-pyrimidyl, 2-pyrazinyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 2-benzothienyl, 3-benzothienyl, 2-indolyl, 3-indolyl. Amino, 3-methoxyanilino, 1-naphthylamino, quinoline-5-amino, 1-piperidyl and 1-pyrrolidinyl.
Further, the 2, 4-diphenyl substituted imidazole compound is a pharmaceutically acceptable salt of formula I.
Further, the 2, 4-diphenyl substituted imidazole compound formula I is selected from compounds 1-21, and the structure is shown as follows:
Figure BDA0001828026110000022
Figure BDA0001828026110000031
the invention also provides a preparation method of the 2, 4-diphenyl substituted imidazole compound or the pharmaceutically acceptable salt thereof, which comprises the following steps: 1-methoxy-4-phenyl acetylene benzene (formula II) and benzaldehyde (formula III) react under the action of ammonium acetate and trimethyl acetic acid by heating with dimethyl sulfoxide/water as a mixed solvent (step one) to obtain an intermediate 1; and (3) reacting the obtained intermediate 1 with aryl benzyl sulfonyl chloride under an alkaline condition (step two), and finally obtaining a product with a structure shown in the formula I, wherein the reaction process is as follows:
Figure BDA0001828026110000041
further, the ratio of dimethyl sulfoxide/water required to prepare intermediate 1 (step one) is from 10:1 to 1:5, preferably 1: 1.
The 2, 4-diphenyl substituted imidazole compound formula I suspending agent comprises the following components: 1-30 parts of 2, 4-diphenyl substituted imidazole compound or pharmaceutically acceptable salt thereof, wetting agent, 1-20 parts of dispersing agent, 0.1-5 parts of defoaming agent, binder, 1-10 parts of disintegrating agent, carrier and water. Wherein the dispersing agent for dispersing is one or more of sodium lignosulphonate, calcium lignosulphonate, polycarboxylate, alkylphenol polyoxyethylene formaldehyde condensate, fatty alcohol polyoxyethylene ether sulfate and alkylphenol polyoxyethylene ether succinate sulfonate. Wherein the defoaming agent with defoaming function is one or more of emulsified silicone oil, high-carbon alcohol fatty acid ester compound, polyoxyethylene polyoxypropylene pentaerythritol ether, polyoxyethylene polyoxypropylene amine ether, polyoxypropylene glycerol ether, polyoxypropylene polyoxyethylene glycerol ether and polydimethylsiloxane. Wherein the disintegrating agent for disintegrating is one or more of urea, sodium chloride, sulfate, carbonate and sodium carboxymethylcellulose. Other dispersants with a dispersing action, other defoamers with a defoaming action and other disintegrants with a disintegrating action may also be selected for use in the present invention.
The preparation method comprises the following steps in sequence:
(1) accurately weighing the raw materials according to the proportion of the suspending agent;
(2) mixing 2, 4-diphenyl substituted imidazole compound, wetting agent, dispersing agent, defoaming agent, binder, disintegrating agent, carrier and water to obtain slurry;
(3) putting the slurry into a sand mill for superfine grinding, and controlling the average particle size to be less than or equal to 4 mu m;
(4) homogenizing in a homogenizer to homogenize the particles to obtain the 2, 4-diphenyl substituted imidazole compound suspending agent.
The invention also provides a research on the bacteriostatic activity of the compound on wheat sharp eyespot, a field drug effect test on wheat sharp eyespot and an influence test on the germination condition of wheat.
Detailed Description
Example 1: synthesis of intermediate 1
Figure BDA0001828026110000051
Adding 1-methoxy-4-phenylacetylene benzene (1.12mmo L) and DMSO/water (4m L, 1:1) into a round-bottom flask, stirring for dissolving, sequentially adding benzaldehyde (1.12mmo L), ammonium acetate (4.48mmo L) and trimethylacetic acid (1.12mmo L), heating the mixture at 140 deg.C, stirring for 30h, pouring the reaction solution into cold saturated sodium bicarbonate solution, extracting with ethyl acetate, washing the combined organic phase saturated saline solution, drying with anhydrous sodium sulfate, filtering, concentrating the filtrate by rotary evaporation, and performing silica gel column chromatography on the residuePurification of the gum (ethyl acetate/hexanes ═ 2/1) afforded intermediate 1 as a yellow solid in 85% yield.1H-NMR(CDCl3,400MHz):H 7.92(d,J＝7.6Hz,2H),7.51(d,J＝8.0Hz,2H),7.42(t,J＝8.0Hz,4H),7.37(t,J＝8.0Hz,2H),7.29(m,2H),6.84(d,J＝8.8Hz,2H),3.79(s,3H).
Example 2: synthesis of intermediate 2
Figure BDA0001828026110000052
Adding NaH (2.5 equivalent) into a dried round-bottom flask, adding an anhydrous THF solution under ice bath after nitrogen protection, stirring for 5min under ice bath, dropwise adding an anhydrous THF (2.5m L) solution of an intermediate 1(0.5mmo L), after the addition is finished, dropwise adding an anhydrous THF solution of isoquinoline-7-methanesulfonyl chloride (1.5 equivalent) under ice bath, after the dropwise adding is finished, slowly raising the reaction liquid to room temperature, heating and stirring at 70 ℃ in oil bath for 12h, cooling the reaction liquid to room temperature, adding a saturated sodium chloride solution, extracting with ethyl acetate, washing the combined organic phase saturated saline solution with anhydrous sodium sulfate, drying, filtering, carrying out rotary evaporation and concentration on the filtrate, and purifying column chromatography residue silica gel (ethyl acetate/n-hexane is 1/1) to obtain a compound 1, namely a yellow solid, wherein the yield is 73%.1H-NMR(CDCl3,400MHz):8.31-8.28(m,2H),7.94(d,J＝7.6Hz,2H),7.53(d,J＝8.0Hz,2H),7.49-7.44(m,2H),7.43(t,J＝8.0Hz,4H),7.41-7.39(m,2H),7.39(t,J＝8.0Hz,2H),7.29(m,2H),6.85(d,J＝8.8Hz,2H),3.80(s,3H),3.02(s,2H).
Example 3: 10% suspension of Compound 1
Firstly, prescription:
110g of compound, 15g of sodium dodecyl sulfate (wetting agent), 20g of sodium lignosulfonate (dispersing agent), 2g of emulsified silicone oil (defoaming agent), 2g of gelatin (binder), 5g of urea (disintegrating agent), 10g of diatomite (carrier) and 36g of water.
II, operating steps:
(1) accurately weighing the raw materials according to the proportion of the suspending agent;
(2) mixing the compound 1, sodium dodecyl sulfate, sodium lignosulphonate, emulsified silicone oil, gelatin, urea, diatomite and water to obtain slurry;
(3) putting the slurry into a sand mill for superfine grinding, and controlling the average particle size to be less than or equal to 4 mu m;
(4) homogenizing in a homogenizer to homogenize the particles to obtain a 10% suspension of compound 1.
Example 4: 20% suspending agent of Compound 1
Firstly, prescription:
120g of compound, 15g of sodium dodecyl sulfate (wetting agent), 15g of sodium lignosulfonate (dispersing agent), 2g of emulsified silicone oil (defoaming agent), 2g of gelatin (binder), 5g of urea (disintegrating agent), 8g of diatomite (carrier) and 33g of water.
II, operating steps:
(1) accurately weighing the raw materials according to the proportion of the suspending agent;
(2) mixing the compound 1, sodium dodecyl sulfate, sodium lignosulphonate, emulsified silicone oil, gelatin, urea, diatomite and water to obtain slurry;
(3) putting the slurry into a sand mill for superfine grinding, and controlling the average particle size to be less than or equal to 4 mu m;
(4) homogenizing in a homogenizer to homogenize the particles to obtain a 20% suspension of compound 1.
Example 5: 2% seed coating preparation of Compound 1
Firstly, prescription:
12g of compound, 10g of modified starch, 3g of alkylphenol polyoxyethylene tetraether (OP-4), 10g of alkyl naphthalene formaldehyde condensation product sodium sulfonate, 10g of sodium dodecyl sulfate, 0.8g of propylene glycol, 0.8g of hydroxyethyl cellulose, 0.5g of silicone, 2g of alkaline rose essence and the balance of water to 100 g.
II, operating steps:
firstly, uniformly shearing and mixing modified starch, alkylphenol polyoxyethylene tetraether (OP-4), alkyl naphthalene formaldehyde condensate sodium sulfonate, sodium dodecyl sulfate, propylene glycol, hydroxyethyl cellulose, silicone and water at a high speed, then adding the compound 1 into a sand mill, grinding for 3 hours to ensure that the particle size is less than 5 mu m, finally adding alkaline rose essence, and uniformly mixing to prepare the 2% seed coating agent of the compound 1.
Example 6: preparation of 2% seed coating agent of tebuconazole
Firstly, prescription:
2g of tebuconazole, 10g of modified starch, 3g of alkylphenol polyoxyethylene tetraether (OP-4), 10g of alkyl naphthalene formaldehyde condensate sodium sulfonate, 10g of sodium dodecyl sulfate, 0.8g of propylene glycol, 0.8g of hydroxyethyl cellulose, 0.5g of silicone, 2g of alkaline rose essence and the balance of water to 100 g.
II, operating steps:
firstly, uniformly shearing and mixing modified starch, alkylphenol polyoxyethylene tetraether (OP-4), alkyl naphthalene formaldehyde condensate sodium sulfonate, sodium dodecyl sulfate, propylene glycol, hydroxyethyl cellulose, silicone and water at a high speed, then adding tebuconazole into a sand mill to be ground for 3 hours until the particle size is less than 5 mu m, finally adding alkaline rose essence, and uniformly mixing to prepare the 2% seed coating agent of tebuconazole.
Test example 1: bacteriostatic activity of compound 1 on rhizoctonia cerealis
1. A potato glucose culture medium (PDA) is prepared by weighing 200g peeled potato, cutting into small pieces, adding 1L water, boiling for 0.5h, filtering out potato pieces with gauze, adding water to 1L, adding 18g glucose and 15g agar, heating to melt agar, filtering with gauze, packaging, and sterilizing.
2. The test method comprises the following steps:
(1) and (3) culturing pathogenic bacteria: inoculating Rhizoctonia cerealis into PDA plate, and culturing in dark at 12 deg.C for 10 days.
(2) The indoor toxicity test method comprises respectively preparing compound 1 and positive control drug diniconazole with DMSO to concentration of 1 × 105Mu.g/m L mother liquor, stored in a 4 ℃ refrigerator, when measuring virulence, respectively diluted into 8 concentration gradients by DMSO, respectively 0, 0.5, 1, 2.5, 5, 10, 25 and 50 mu.g/m L, absorbing each concentration of medicament 60 mu L by a pipette, adding the medicament into sterilized 60m L PDA culture medium cooled to 45 ℃, after mixing uniformly, pouring the PDA culture medium with the medicament into 9 cm-diameter culture dishes, each dish is 15m L, each medicament concentration is repeated for 4 times, and setting up a blank control by only adding 60 mu L DMSO.
Making Rhizoctonia cerealis plate cultured for 10 days along colony edge by using puncherPreparing fungus cake with diameter of 0.5cm, inoculating hypha face down in the culture medium with medicine and blank control, culturing in 12 deg.C incubator in dark, measuring colony diameter after 10 days, and calculating hypha growth inhibition rate. And (3) converting the concentration of the medicament into a logarithmic value (X) with the base of 10 by taking the inhibition rate as a Y value, and calculating a toxicity regression curve equation for the wheat sheath blight disease by taking the X-Y as a regression line. Concentration EC of 50% maximum Effect of Compound 1 and Positive control drug diniconazole50Value and 90% inhibitory concentration EC90The values are given in table 1 below.
TABLE 1 bacteriostatic effect of Compound 1 and Positive control on Rhizoctonia cerealis
Group of Regression curve equation of virulence EC50(μg/mL) EC90(μg/mL)
Compound 1 y＝2.0209x+3.9809(r＝0.9805) 0.02 0.06
Positive control drug y＝1.1009x+6.0294(r＝0.9233) 0.05 0.10
As is clear from Table 1, Compound 1 has a significant inhibitory effect on the growth of hyphae of Rhizoctonia cerealis.EC of Compound 150Value and EC90The value is obviously smaller than that of a positive control drug, and the excellent activity of inhibiting the rhizoctonia cerealis is shown.
Test example 2: test of field drug effect of wheat sheath blight
Referring to section 108 of pesticide field efficacy test criteria (second): the bactericide is used for preventing and treating wheat sharp eyespot: GB/T17980.108-2004 carries out the field efficacy test. The disease index was investigated before application in a random array according to the treatment of the cells of the example 3 group, the example 4 group, the positive control thifluzamide suspension and the blank control, and the control effect was investigated twice before each application and 7 days after the last application. Four points are randomly selected for investigation in each cell, two plants are investigated in each point, and all leaves are investigated in each plant.
Classification method (in units of leaves):
level 0: no disease spots;
level 1: the lesion area accounts for less than 5% of the whole leaf area;
and 3, level: the lesion area accounts for 6 to 10 percent of the whole leaf area;
and 5, stage: the lesion area accounts for 11% -25% of the whole leaf area;
and 7, stage: the lesion area accounts for 26-50% of the whole leaf area;
and 9, stage: the lesion area accounts for more than 50% of the whole leaf area.
Disease index is ∑ (relative grade number of disease leaves × at each stage)/(total leaf number of investigation × highest grade value 9) × 100
Relative preventing and treating effect (%) (control disease index-treating disease index)/control disease index × 100
The results of the tests are shown in Table 2 below.
TABLE 2 test results of field drug effect of wheat sheath blight
Figure BDA0001828026110000081
Figure BDA0001828026110000091
The test results show that different contents of the compound 1 suspending agent (example 3, example 4) have different degrees of effect on wheat sharp eyespot. Compared with the positive control drug thifluzamide (24% suspending agent), the example 4 (20% suspending agent of the compound 1) has better effect of preventing and treating sheath blight under different time periods and treatment doses.
Test example 3: effect of Compound 1 seed coating agent on wheat Germination
1. Test materials:
example 5 (2% seed coating of compound 1), example 6 (2% seed coating of tebuconazole), and wheat 411.
2. The test method comprises the following steps:
the Jing 411 wheat was treated with the seed coating agent of example 5 and the seed coating agent of example 6 at a ratio of 0.15, 0.3, 0.6, 1.2, 2.4gai/kg, respectively, and sowed in a sand culture dish sterilized at high temperature and containing 17% of water, 50 grains per dish, 25 grains per pot, and 3 times of treatment were repeated, and then cultured in an incubator. And (4) measuring the germination vigor, the germination rate and the emergence rate. The test results are shown in Table 3.
TABLE 3 influence on wheat germination and emergence
Figure BDA0001828026110000092
Test results show that compared with a positive control medicament, namely tebuconazole, the compound 1 with different coating dosages has no change on the germination vigor, the germination rate and the emergence rate of wheat, and the compound 1 has no interference on seed germination; the triazole antibacterial agent tebuconazole interferes with the germination of seeds.

Claims (10)

  1. A2, 4-diphenyl substituted imidazole compound or a pharmaceutically acceptable salt thereof has a structure shown in formula I:
    Figure DEST_PATH_IMAGE001
    wherein Ar is selected from the group consisting of 7-isoquinolinyl, 6-isoquinolinyl, 7-quinolyl, 6-quinolyl, 2-quinolyl, 3-isoquinolyl, 3-quinolyl, 2-pyridyl, 3-pyridyl4-pyridyl, 2-pyrimidyl, 4-pyrimidyl, 2-pyrazinyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 2-benzothienyl, 3-benzothienyl, 2-indolyl, 3-indolyl.
  2. 2. The 2, 4-diphenyl-substituted imidazole compound or pharmaceutically acceptable salt thereof according to claim 1, which has the following specific structure:
    Figure 72613DEST_PATH_IMAGE003
    Figure DEST_PATH_IMAGE004
    Figure 989753DEST_PATH_IMAGE005
    。
  3. 3. the use of a 2, 4-diphenyl-substituted imidazole compound or a pharmaceutically acceptable salt thereof according to claim 1 for the control of wheat blight.
  4. 4. The process for the preparation of 2, 4-diphenyl-substituted imidazoles or pharmaceutically acceptable salts thereof as claimed in claim 1 wherein:
    the method comprises the following steps: 1-methoxy-4-phenyl acetylene benzene (formula II) and benzaldehyde (formula III) are heated and reacted by taking dimethyl sulfoxide/water as a mixed solvent under the action of ammonium acetate and trimethylacetic acid to obtain an intermediate 1;
    step two: the obtained intermediate 1 reacts with aryl benzyl sulfonyl chloride under the conditions of NaH and THF to finally obtain a product with a structure shown in a formula I, wherein the reaction process is as follows:
    Figure DEST_PATH_IMAGE006
    。
  5. 5. the method of claim 4, wherein: the ratio of dimethyl sulfoxide to water required in the first step is 10:1-1: 5.
  6. 6. A suspending agent is characterized in that: the active ingredient containing the 2, 4-diphenyl substituted imidazole compound or the pharmaceutically acceptable salt thereof according to claim 1, a wetting agent, a dispersing agent, an antifoaming agent, a binder, a disintegrating agent, a carrier and water.
  7. 7. The suspension as claimed in claim 6, wherein: the formula ratio of the 2, 4-diphenyl substituted imidazole compound or the pharmaceutically acceptable salt thereof is 1-30 parts.
  8. 8. The suspension as claimed in claim 6, wherein: the dispersing agent is selected from one or more of sodium lignosulfonate, calcium lignosulfonate, polycarboxylate, alkylphenol polyoxyethylene formaldehyde condensate, fatty alcohol polyoxyethylene ether sulfate and alkylphenol polyoxyethylene ether succinate sulfonate, and the formula proportion of the dispersing agent is 1-20 parts.
  9. 9. The suspension as claimed in claim 6, wherein: the defoaming agent is selected from one or more of emulsified silicone oil, a high-alcohol fatty acid ester compound, polyoxyethylene polyoxypropylene pentaerythritol ether, polyoxyethylene polyoxypropylene amine ether, polyoxypropylene glycerol ether, polyoxypropylene polyoxyethylene glycerol ether and polydimethylsiloxane, and the formula ratio of the defoaming agent is 0.1-5 parts.
  10. 10. The suspension as claimed in claim 6, wherein: the disintegrating agent is selected from one or more of urea, sodium chloride, sulfate, carbonate and sodium carboxymethyl cellulose, and the formula proportion of the disintegrating agent is 1-10 parts.
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000273088A (en) * 1999-01-18 2000-10-03 Nippon Soda Co Ltd Triphenylimidazole
JP2001163861A (en) * 1999-12-07 2001-06-19 Nippon Soda Co Ltd Diphenylimidazole compound and fungicide for agriculture and horticulture

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000273088A (en) * 1999-01-18 2000-10-03 Nippon Soda Co Ltd Triphenylimidazole
JP2001163861A (en) * 1999-12-07 2001-06-19 Nippon Soda Co Ltd Diphenylimidazole compound and fungicide for agriculture and horticulture

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Metal-Free, Acid-Promoted Synthesis of Imidazole Derivatives via a Multicomponent Reaction;Chung-Yu Chen等;《ORGANIC LETTERS》;20131126;第15卷(第2期);第6116-6119页 *

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