CN101289434B - 1,5-difuranyl pentadienones, preparation method and sterilization activity thereof - Google Patents
1,5-difuranyl pentadienones, preparation method and sterilization activity thereof Download PDFInfo
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- CN101289434B CN101289434B CN2008100447293A CN200810044729A CN101289434B CN 101289434 B CN101289434 B CN 101289434B CN 2008100447293 A CN2008100447293 A CN 2008100447293A CN 200810044729 A CN200810044729 A CN 200810044729A CN 101289434 B CN101289434 B CN 101289434B
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- 238000002360 preparation method Methods 0.000 title abstract description 6
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- 201000010099 disease Diseases 0.000 claims abstract description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
- 241000894006 Bacteria Species 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 2
- JUKHVNMXKSHNQY-UHFFFAOYSA-N penta-3,4-dien-2-one Chemical class CC(=O)C=C=C JUKHVNMXKSHNQY-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- -1 1, 5-difuryl pentadiene ketones compound Chemical class 0.000 abstract description 13
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- 239000003899 bactericide agent Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
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- 241000589771 Ralstonia solanacearum Species 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 241001272684 Xanthomonas campestris pv. oryzae Species 0.000 description 2
- 244000273928 Zingiber officinale Species 0.000 description 2
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- IEMMBWWQXVXBEU-UHFFFAOYSA-N 2-acetylfuran Chemical class CC(=O)C1=CC=CO1 IEMMBWWQXVXBEU-UHFFFAOYSA-N 0.000 description 1
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- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 239000005746 Carboxin Substances 0.000 description 1
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- 241000588698 Erwinia Species 0.000 description 1
- 241000526118 Fusarium solani f. radicicola Species 0.000 description 1
- 241001344131 Magnaporthe grisea Species 0.000 description 1
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- 206010027146 Melanoderma Diseases 0.000 description 1
- 241001480037 Microsporum Species 0.000 description 1
- 241000932831 Pantoea stewartii Species 0.000 description 1
- 241000588702 Pectobacterium carotovorum subsp. carotovorum Species 0.000 description 1
- 241000172199 Phyllospora Species 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
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- 244000098338 Triticum aestivum Species 0.000 description 1
- 241000589636 Xanthomonas campestris Species 0.000 description 1
- 241001668516 Xanthomonas citri subsp. malvacearum Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006013 carbendazim Substances 0.000 description 1
- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 description 1
- GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- ACMXQHFNODYQAT-UHFFFAOYSA-N cyflufenamid Chemical compound FC1=CC=C(C(F)(F)F)C(C(NOCC2CC2)=NC(=O)CC=2C=CC=CC=2)=C1F ACMXQHFNODYQAT-UHFFFAOYSA-N 0.000 description 1
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- BUDVPGDSBALRCO-UHFFFAOYSA-N furan;prop-2-enal Chemical class C=CC=O.C=1C=COC=1 BUDVPGDSBALRCO-UHFFFAOYSA-N 0.000 description 1
- 238000009630 liquid culture Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- BSDQITJYKQHXQR-UHFFFAOYSA-N methyl prop-2-eneperoxoate Chemical compound COOC(=O)C=C BSDQITJYKQHXQR-UHFFFAOYSA-N 0.000 description 1
- 238000009629 microbiological culture Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
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- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention relates to the preparation of a 1, 5-difuryl pentadiene ketones compound, which is the compound of the structural formula (I), wherein, R1 is fluoride atom, chlorine atom, bromine atom, methyl, ethyl, propyl and isopropyl; R2 is fluoride atom, chlorine atom, bromine atom, methyl, ethyl, propyl and isopropyl. The preparation can be applied to controlling plant diseases caused by bacteria or fungi.
Description
Technical Field
The invention relates to a preparation method of 1, 5-difuranyl pentadiene ketone compound, which can be applied to the prevention and treatment of plant diseases caused by bacteria or fungi.
Background
Plant diseases caused by plant bacteria or fungi are the large enemies of agricultural production, and the average yield reduction loss caused by the plant suffering from the diseases is 10-15% of the total yield according to the statistics of the Food and Agriculture Organization (FAO) of the United nations. Due to the difficulty of control, great loss is caused to agricultural production, for example, in 2007, the agricultural loss caused by plant diseases caused by plant bacteria or fungi reaches 100 hundred million RMB.
In order to prevent and treat plant diseases caused by plant bacteria or fungi, various researches are carried out, and from the middle leaves of the 20 th century 60 years, cis-butenamide bactericides carboxin with a treatment effect on the plant diseases, particularly broad-spectrum, efficient and low-toxicity benzimidazole bactericides benomyl, carbendazim and the like are successfully developed by human beings, so that the fact that the human beings adopt chemical weapons to control the plant diseases makes a major breakthrough is marked, and the chemical prevention and treatment of the plant diseases and the development of the bactericides enter a brand-new historical period. The occurrence of systemic bactericides stimulates the enthusiasm of human beings for using a large amount of chemical pesticides to prevent and treat plant diseases. However, they also have different problems, which limit their applications. For example, cyflufenamid has poor systemic activity and cannot be well absorbed by tissues; triazolone is a systemic treatment type bactericide, has a single action mechanism and action site, is frequently used for a long time, and has relatively serious resistance to diseases [ the institute of agriculture and forestry, science and technology university, northwest, (Nature science edition), 2005, 33, 233-; the methoxy acrylate bactericide has a unique action mechanism, but pathogenic bacteria are easy to generate resistance.
Disclosure of Invention
The invention aims to provide a 1, 5-difuranyl pentadiene ketone compound which can be applied to the control of plant diseases caused by bacteria or fungi.
The present invention is a compound of the following structural formula (I):
wherein,
R1is fluorine atom, chlorine atom, bromine atom, methyl, ethyl, propyl, isopropyl;
R2is fluorine atom, chlorine atom, bromine atom, methyl, ethyl, propyl or isopropyl.
The compounds of general formula (I) are prepared by aldol condensation of various substituted 2-acetylfurans with substituted furan propenals in protic solvents such as ethanol.
In the formula R1，R2The same as above.
The compound with the general formula (I) has better control on plant diseases caused by bacteria or fungi.
The 1, 5-difuranyl pentadiene ketone compound is easy to synthesize, low in cost, good in inhibition effect on plant bacteria or plant fungi, novel in structure and free of reports in the existing compounds with good inhibition effect on plant germs and plant fungi. The design and synthesis of the invention meet the requirements of environment-friendly and green chemistry.
The foregoing aspects of the present invention will be described in further detail with reference to specific embodiments. This is not to be construed as limiting the invention.
Detailed Description
The 1, 5-difuranyl pentadienones of the following examples are all from the institute for pesticide and crop protection of Sichuan university, the pathogenic bacteria of the tested plants are from Sichuan university, institute for biology of the national institute of Olympic, China general microbiological culture Collection center and Sichuan province academy of agricultural science, and the tested agricultural pests are from the field of the institute for pesticide and crop protection of Sichuan university.
Example 1 Compounds
Preparation of
5-Methylacetofuran (10mmol, 1.24g) was dissolved in 10ml of ethanol, and furalacldehyde (10mmol, 1.22g) was added. NaOH powder (1mmol, 0.040g) was added in portions with constant stirring, and stirred uniformly. Keeping the temperature of the reaction system at 0 ℃, after the addition is finished, continuing to react for 24 hours at room temperature, adding 100ml of water for dilution, separating out yellow solid, filtering out the solid, washing, drying by infrared rays, and recrystallizing with absolute ethyl alcohol to obtain 1.58g of light yellow crystal with the yield of 69.30%.
1H-NMR(400MHz，CDCl3)：2.43(3H，s)，6.19～6.20(1H，m)，6.45～6.49(2H，m)，6.76(1H，d，J＝15.2Hz)，6.86～6.94(2H，m)，7.17(1H，d，J＝3.2Hz)，7.45(1H，s)，7.53～7.60(1H，m)
Example 21, 5-Difuropyranylpentadienones fungicidal Activity assay for plant pathogenic bacteria and fungi
1 test plant pathogenic bacteria
1.1 test for plant pathogenic bacteria
Rice bacterial blight (Xanthomonas oryzae pv. oryzae), cotton angular leaf spot (Xanthomonas campestris pv. malvacearum), corn bacterial blight (Pantoea stewartii subsp. stewartii), tobacco bacterial wilt (Pseudomonas solanacearum pv. tabaci), potato soft rot (Erwinia carotovora subsp. carotovora), ginger bacterial wilt (Ralstonia solanacearum), cabbage black rot (Xanthomonas campestris pv. Camptorrhoea), cabbage soft rot (Erwinia carotoyoidea).
1.2 test for phytopathogenic fungi
Pyricularia oryzae (Piricularia oryzae Cav), Rhizoctonia solani (Rhizoctonia solani), Fusarium graminearum (Fusarium graminearum), Microsporum maydis (Bipolaris maydis), Phytophthora infestans (Phytophthora infestans), Nicotiana tabacum (Colcotrichum nicotianae), Phyllospora brassicae (Alternaria brassica), Botrytis cinerea (Botrytis cinerea).
2, experimental method:
2.11, 5-Difuranyl pentadienones for determining the bacteriostatic activity of plant pathogenic bacteria
The colony inhibition (%) was determined by the growth rate method:
the plant pathogenic bacteria 1.1 are respectively diluted to certain concentration, added into a liquid culture medium of the 1, 5-difuryl pentadiene ketone compounds (the final concentration of the 1, 5-difuryl pentadiene ketone compounds is prepared into a series of 1, 5-difuryl pentadiene ketone compound concentration gradient culture mediums by adopting a test tube double dilution method), each series is inoculated with a test bacteria suspension, each concentration is repeated for 3 times, and sterile water is used as a blank control. After culturing at 35-38 deg.C for 18-24 hr, the serial cultures are subjected to bacteria count by gradient dilution method, and colony inhibition rate is determined according to colony number, and the formula is as follows:
2.21 antibacterial activity determination of 5-difuranyl pentadiene ketone compound on plant pathogenic fungi the relative inhibition ratio (%) of hyphae is determined by a toxic medium method:
firstly diluting 1, 5-difuryl pentadiene ketone compound with sterile water, then mixing with PDA culture medium, adopting double dilution method to make a series of medicine-containing plates with uniform thickness, using sterile water as blank control, repeating every treatment for 3 times. After the culture medium is solidified, inoculating the test fungus cake of plant pathogenic fungi on the solidified culture medium, culturing at 27-28 deg.C for 3-5 days, measuring the diameter of the fungus cake to be 0.4cm, and calculating the inhibition rate of hypha growth by cross method.
3 results of the experiment
The result of the determination of the bacteriostatic activity of the 1, 5-difuranyl pentadienones on the plant pathogenic bacteria is shown in Table 1. The results in Table 1 show that the 1, 5-difuranyl pentadienones have good inhibitory action on plant pathogenic bacteria.
TABLE 1 relative inhibition (%), at 50mg/L, of the compound of example 1 against phytopathogenic bacteria
| Bacterial strain | Colony inhibition (%) | Bacterial strain | Colony inhibition (%) |
| Bacterial blight of rice | 100 | Cotton angular leaf spot germ | 85.37 |
| Bacterial wilt of corn | 90.31 | Bacterial wilt of tobacco | 96.30 |
| Soft rot of potato | 88.64 | Soft rot of Chinese cabbage | 100 |
| Cabbage black rot | 73.25 | Ginger bacterial wilt | 46.28 |
The results of the measurement of the inhibitory activity of 1, 5-difuranyl pentadienones against phytopathogenic fungi are shown below (see Table 2). The results in Table 2 show that the 1, 5-difuranyl pentadienones compound also has good inhibitory action on plant pathogenic fungi.
TABLE 2 relative inhibition (%). of the compound of example 1 at 50mg/L against phytopathogenic fungi
| Bacterial strain | Relative inhibition ratio (%) | Bacterial strain | Relative inhibition ratio (%) |
| Magnaporthe grisea | 100 | Rhizoctonia solani of rice | 100 |
| Wheat scab germ | 68.30 | Corn leaf spot germ | 90.38 |
| Black spot of Chinese cabbage | 87.34 | Late blight of potato | 79.30 |
| Botrytis cinerea | 98.36 | Tobacco anthracnose pathogen | 79.69 |
In conclusion, the 1, 5-difuranyl pentadiene ketone compound has good broad-spectrum bactericidal activity on plant pathogenic bacteria, is developed into a novel stable, efficient and nontoxic green pesticide, and has wide prospects.
Claims (3)
1. A5-difuranyl pentadienones characterized by being compounds of structure (I):
wherein,
R1is fluorine atom, chlorine atom, bromine atom, methyl, ethyl, propyl, isopropyl;
R2is fluorine atom, chlorineAtom, bromine atom, methyl, ethyl, propyl and isopropyl.
2. A method of synthesizing a compound according to claim 1, comprising the reaction of:
wherein,
R1，R2has the meaning of claim 1.
3. The use of 1, 5-difuranyl pentadienones according to claim 1, characterized by their use for controlling plant diseases caused by bacteria or fungi.
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