CN113527099A - Beta-diketone for resisting plant pathogenic fungi - Google Patents
Beta-diketone for resisting plant pathogenic fungi Download PDFInfo
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- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
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- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
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- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/395—Saturated compounds containing a keto group being part of a ring of a five-membered ring
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- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/784—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic with all keto groups bound to a non-condensed ring
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- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
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- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
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- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
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- C07C2601/00—Systems containing only non-condensed rings
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- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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Abstract
The invention discloses a beta-diketone for resisting plant pathogenic fungi, relates to the field of biopesticides, and provides a compound for resisting crop pathogenic fungi and a preparation method thereof. At present, chemical pesticides are single in variety, diseases are easy to generate drug resistance, the pesticide effect is reduced, and pesticide residues harm the health and the environment of people. Therefore, the search for efficient, broad-spectrum and safe biological pesticides has become a difficult point and a hot point in the research and development of new pesticides at present. The technical problem to be solved is to find an active ingredient for resisting crop pathogenic fungi, thereby improving the pesticide effect, reducing the dosage and inhibiting the pesticide resistance. The invention adopts a growth rate method to measure the antibacterial activity of the medicine. The invention has better effect on plant fungal diseases such as rhizoctonia solani, cucumber fusarium wilt, botrytis cinerea, corn northern leaf blight, fusarium graminearum and the like. The control objects comprise crops such as rice, corn, wheat, soybean, rape, sesame, Chinese cabbage, melon, eggplant, green soybean, cucumber, strawberry and the like.
Description
Technical Field
The invention relates to the field of biological pesticides, and discloses beta-diketone for resisting plant pathogenic fungi.
Background
Annual plant diseases, in which the number of diseases caused by phytopathogenic fungi is at most, account for about 70% of all plant diseases, and almost every crop suffers from fungal damage, cause significant economic losses to agricultural production. According to statistics, fungal diseases have caused the production reduction of 1.25 hundred million tons/year of grain crops such as rice, wheat, corn, potato, soybean and the like in the global range. According to statistics, if no pest control technology, especially pesticide application is adopted, the yield loss of crops per year can reach 50% -70%. Pesticides make great contribution to agricultural production, but more and more disadvantages such as environmental pollution, pesticide residues, virus resistance, host injury and the like are generated in the using process. The organic synthetic pesticide is the pesticide with the highest use rate at present, but because pathogenic bacteria easily generate drug resistance or drug resistance to the organic synthetic pesticide, the pesticide effect is easily reduced, farmers are forced to increase the dosage, and as a result, pesticide residue is generated, which is harmful to the health and environment of people. Therefore, the research and development of efficient, specific, safe and green biological pesticides become the research and development focus of the current novel pesticides. Compared with chemical pesticides, the biological pesticide has the advantages of safety, small toxic and side effects, no environmental pollution and the like. The rapid development of biopesticides has become a necessary trend. At present, most of biological pesticides on the market mainly comprise crude extracts or mixtures except a few varieties with definite active ingredients, so that the application blindness is high, the drug effect is poor, and the risk of difficult prediction exists.
In order to solve the problems, the invention extracts and separates a series of components for inhibiting and killing pathogenic fungi from plants, and nine active monomer components are separated from the components through further activity screening and purification.
Disclosure of Invention
The invention aims to provide a broad-spectrum compound for preventing and treating fungal diseases, which has high drug effect, can delay the drug resistance and drug resistance of pathogenic bacteria, and has certain advantages in reducing the use amount of chemical pesticides, restoring the ecological environment, reducing pesticide residues and strengthening food.
The general structural formula of the active component is as follows:
a β -diketone compound for controlling phytopathogenic fungi, which comprises a compound represented by the formula (1) or a salt thereof:
wherein R1, R2 represent a hydrogen atom, an alkyl group, an aromatic ring, an ester group, etc.;
the pathogenic fungi include Rhizoctonia solani, Fusarium oxysporum, Botrytis cinerea, northern leaf blight, Fusarium graminearum, etc.
The compound of the above (1), wherein the compound is selected from the group consisting of methyl 2, 4-carbonylphenylbutyrate, benzoylformic acid, dibenzoylmethane, 1, 3-cyclopentanedione, methyl 2-chloro-A, G-Dioxo-phenylbutyrate, 1, 3-acetonedicarboxylic acid, 4, 6-dioxy-6-phenylhexanoic acid, 6-Hydroxy-1-phenyl-1, 3-hexanedione and 6-Hydroxy-1- (4-methylphenyl) -1, 3-dione.
The compounds are respectively as follows in the attached drawings of the specification: FIG. 1 is a structural general formula of compound (1), FIG. 1-1 is methyl 2, 4-carbonylphenylbutyrate, FIG. 1-2 is benzoylcarboxylic acid, FIG. 1-3 is dibenzoylmethane, FIG. 1-4 is 1, 3-cyclopentanedione, FIG. 1-5 is methyl 2-chloro-A, G-Dioxo-phenylbutyrate, FIG. 1-6 is 1, 3-acetonedicarboxylic acid, FIG. 1-7 is 4, 6-dioxy-6-phenylhexanoic acid, FIG. 1-8 is 6-Hydroxy-1-phenyl-1, 3-hexanedione, FIG. 1-9 is 6-Hydroxy-1- (4-methylphenyl) -1, 3-dione.
The compound according to the above (1), wherein the content of the compound (1) or a salt thereof is 0.1 to 80% by mass of the entire pesticide.
The compound according to the above (1), wherein at least one solvent is contained, and the mass of the solvent is 1% to 80% of the total pesticide mass. The solvent can be selected from acetone, methanol, dichloromethane, ethanol, water, ethyl acetate, ethylenediamine, ethylene glycol, dioxane, toluene, pyridine, piperidine and tween, and these solvents can be used alone or in combination.
Table 1 shows preferred examples of the compounds represented by the above formula (1).
Preferred examples of the compounds of Table 1
| Name (R) | R1 | R2 |
| 2, 4-Carbonylphenylbutyric acid methyl ester | CH3OCO | Ph |
| Benzoic acid | OH | Ph |
| Dibenzoyl methane | Ph | Ph |
| 1, 3-cyclopentanedione | -CH2CH2- | -CH2CH2- |
| 1, 3-acetonedicarboxylic acid | OH | OHCOCH2- |
Further, the content of the active ingredients of the biological pesticide is 1: 900-900: 1, preferably 60: 1-1: 50; further preferably 55: 1 to 50: 10; more preferably 50: 1 to 50: 5.
In a specific embodiment of the invention, the content of active ingredients in the biopesticide is 50: 1 or 50: 5.
The invention provides a biological pesticide which can be prepared from the compound alone, can be used by matching several active ingredients, or can be prepared from the compound and an auxiliary agent or a carrier in the field of pesticides.
The biological pesticide is mainly used for preventing and treating fungal diseases of crops.
The biopesticide can be prepared into agriculturally acceptable formulations such as suspending agents, water dispersible granules, emulsion in water, water dispersible granules, missible oil, wettable powder, granules and the like by adding corresponding additives or carriers according to a method recognized by a person skilled in the art. For example, useful adjuvants or carriers include solvents, emulsifiers, wetting agents, stabilizers, antifreezes, defoamers, thickeners, surfactants or other substances which are beneficial to the stabilization and efficacy of the active ingredient in the formulation, and are all of the various ingredients commonly used or permitted for use in the biopesticide formulation art.
The biopesticides of the present invention may be prepared by methods conventional in the art.
The invention also comprises the application of the biological pesticide compound or the pesticide in the prevention and treatment of fungal diseases.
Furthermore, the control objects comprise vegetables, fruits and crops such as rice, corn, wheat, soybean, rape, sesame, Chinese cabbage, melon, eggplant, green soybean, cucumber, strawberry and the like.
Further, the plant fungal diseases include rhizoctonia solani, fusarium oxysporum, botrytis cinerea, alternaria turcicola, fusarium graminearum and the like.
The starting materials used in the present invention are either commercially available or prepared by methods conventional in the art.
On the basis of the common knowledge in the field, the above-mentioned preferred conditions can be combined with each other to obtain preferred embodiments of the invention.
Further, it is to be understood that terms such as "comprising," "including," and "containing" are also intended to include "consisting of," "made of," and the like.
The compound represented by the formula (1) is an active ingredient extracted and separated from plants, and has certain effect on gray mold and Rhizoctonia solani.
The compound represented by the formula (1) has a broad-spectrum antibacterial effect, and can inhibit rhizoctonia solani, fusarium oxysporum, botrytis cinerea, alternaria maydis, fusarium graminearum and the like.
The invention can also reduce the dosage of effective components, reduce the cost, delay the drug resistance and drug resistance of pathogenic bacteria, and ensure the safety and quality of agricultural products such as vegetables, tea and the like in the production process to a certain extent.
Detailed Description
The compounds represented by the formula (1) used below are all isolated from natural products in an amount of 90% to 99%, and commercially available compounds having similar structures are also included within the scope of the present invention; the rest of the reagents are all commercial products.
Solvent: methanol, acetone, dichloromethane and ethanol.
Preparing a drug-containing flat plate: weighing a certain amount of the compound represented by the formula (1), dissolving with a proper amount of acetone or other solvents, adding a certain amount of mother liquor into 200mL of PDA culture medium, and uniformly mixing to prepare a drug-containing flat plate with a certain concentration. Beating cultured active test bacteria into a bacteria block with the diameter of 5mm from the edge of the hypha, placing the bacteria block in the middle of a culture dish, and repeating the treatment for 3 times; acetone/tween-80 mixture without plant extract was used as a blank control. And then placing the culture dish in a constant-temperature incubator at 25 ℃ for culture, respectively measuring the diameters of bacterial colonies after culturing for a period of time, comparing the diameters with a blank control, and calculating the growth inhibition rate.
Raw materials of a culture medium: glucose, agar and potato.
The following materials are all required to reach the constant weight of water loss.
Example 1 preparation of a drug solution of a compound represented by formula (1).
The formula is as follows: a stock solution of a compound represented by the formula (1) was prepared into drug solutions of different concentrations using acetone.
Test example 1
The compound liquid medicine of the formula (1) is used for preventing and treating rhizoctonia solani.
1.1. Purpose of the experiment
The control effect and the dosage of the liquid medicine of the compound shown in the formula (1) on rhizoctonia solani are improved.
1.2. Test conditions and test objects
1.2.1 test subjects:
rhizoctonia solani.
The preparation method is the same as example 1.
1.2.2 test Environment
The test is carried out in the agricultural laboratory of Qinghua Changsheng research institute of the Asia-Tailu Zhejiang province in the southern lake region of Jiaxing city, Zhejiang, 2019 from 10 months to 11 months.
The strain used in the test is from the microbiological laboratory of Zhejiang university.
1.3 test design and arrangement
1.3.1 Agents
A compound of formula (1) of example 1 in liquid form.
1.3.2 control Agents
The control used an equal amount of acetone.
The amounts of each drug solution are shown in Table 2 below.
TABLE 2 dilution factor of the compound of formula (1)
1.3.3 Medium consumption and number of repetitions
Culture medium: 8 ml.
The number of repetitions: each concentration was repeated 3 times.
1.4 test methods
1.4.1 methods of use: pouring 8ml of culture medium into a culture dish, inoculating pathogenic fungi onto the culture medium after the culture medium is solidified, putting a filter paper sheet with a medicament after the fungi grow to a certain size, and putting the culture medium in a constant-temperature incubator to observe the growth state of the fungi.
1.4.2 Observation methods
The growth of the bacterial mass is observed every 24 hours until the culture dish is full of the bacterial mass of the control group, and the diameters of the bacterial mass of the control group and the bacterial mass of the experimental group are measured by using a ruler.
1.4.3 method of calculating drug efficacy
Growth inhibition (%) was (control colony diameter-treated colony diameter)/(control colony diameter-5 mm) × 100%
1.5 results and analysis
The test results are shown in Table 3.
TABLE 3 test results of the control of Rhizoctonia solani by the compound represented by formula (1)
The results of test example 1 show that the compounds (1) preferably selected from several active ingredient compounds have a good inhibitory effect on Rhizoctonia solani. For example, the bacteriostasis rates of the benzoylformic acid diluted by 400 times are respectively 75 percent; when the dibenzoyl methane is diluted by 200 times, the bacteriostasis rate of rhizoctonia solani is 92 percent; the 2, 4-carbonyl methyl phenylbutyrate is diluted by 600 times to 400 times, the bacteriostasis rate is improved along with the increase of the concentration, certain concentration dependence is shown, when the concentration is diluted to 200 times, the bacteriostasis rate is not obviously improved, and the concentration dependence is reduced.
Test example 2
Experiment for preventing and treating cucumber fusarium wilt by using compound liquid medicine of formula (1).
2.1. Purpose of the experiment
The control effect and the dosage of the liquid medicine of the compound shown in the formula (1) on cucumber fusarium wilt are shown.
2.2. Test conditions and test objects
2.2.1 test subjects
Cucumber fusarium wilt bacteria.
The preparation method is the same as example 1.
2.2.2 test Environment
The test is carried out in the agricultural laboratory of Qinghua Changsheng research institute of the Asia-Tailu Zhejiang province in the southern lake region of Jiaxing city, Zhejiang, 2019 from 10 months to 11 months.
The strain used in the test is from the microbiological laboratory of Zhejiang university.
2.3 test design and arrangement
2.3.1 Agents
A compound of formula (1) of example 1 in liquid form.
2.3.2 control Agents
The control used an equal amount of acetone.
The dosage of each liquid medicine is shown in table 2.
2.3.3 Medium consumption and number of repetitions
Culture medium: 8 ml.
The number of repetitions: each concentration was repeated 3 times.
2.4 test methods
2.4.1 methods of use: pouring 8ml of culture medium into a culture dish, inoculating pathogenic fungi onto the culture medium after the culture medium is solidified, putting a filter paper sheet with a medicament after the fungi grow to a certain size, and putting the culture medium in a constant-temperature incubator to observe the growth state of the fungi.
2.4.2 Observation methods
The growth of the bacterial mass is observed every 24 hours until the culture dish is full of the bacterial mass of the control group, and the diameters of the bacterial mass of the control group and the bacterial mass of the experimental group are measured by using a ruler.
2.4.3 method for calculating drug effect
Growth inhibition (%) was (control colony diameter-treated colony diameter)/(control colony diameter-5 mm) × 100%
2.5 results and analysis
The test results are shown in Table 4.
TABLE 4 bacteriostatic effect of Compound (1) on Fusarium oxysporum f.sp.cubense
The active ingredient compound provided in test example 2 has a good inhibitory effect on cucumber fusarium oxysporum. For example, the bacteriostasis rate is 86% when the benzoylformic acid is diluted by 400 times; the bacteriostasis rate of the dibenzoyl methane diluted by 200 times is 95 percent; the bacteriostasis rate of the 1, 3-cyclopentanedione diluted by 400 times is 79 percent; the 2, 4-carbonyl methyl phenylbutyrate is diluted by 600 times to 400 times, the bacteriostasis rate is improved along with the increase of the concentration, certain concentration dependence is shown, when the concentration is diluted to 200 times, the bacteriostasis rate is not obviously improved, and the concentration dependence is reduced.
Test example 3
Experiment of preventing and treating gray mold with the compound liquid medicine of formula (1).
3.1. Purpose of the experiment
The control effect and the dosage of the liquid medicine of the compound shown in the formula (1) on the gray mold are shown.
3.2. Test conditions and test objects
3.2.1 test subjects
Botrytis cinerea.
The preparation method is the same as example 1.
3.2.2 test Environment
The test is carried out in the agricultural laboratory of Qinghua Changsheng research institute of the Asia-Tailu Zhejiang province in the southern lake region of Jiaxing city, Zhejiang, 2019 from 10 months to 11 months.
The strain used in the test is from the microbiological laboratory of Zhejiang university.
3.3 Experimental design and arrangement
3.3.1 Agents
A compound of formula (1) of example 1 in liquid form.
3.3.2 control Agents
The control used an equal amount of acetone.
The dosage of each liquid medicine is shown in table 2.
3.3.3 Medium consumption and number of repetitions
Culture medium: 8 ml.
The number of repetitions: each concentration was repeated 3 times.
3.4. Test method
3.4.1 methods of use: pouring 8mI culture medium into a culture dish, inoculating pathogenic fungi onto the culture medium after the culture medium is solidified, putting filter paper sheets with medicaments after the fungi grow to a certain size, and putting the culture medium in a constant-temperature incubator to observe the growth state of the fungi.
3.4.2 Observation method
The growth of the bacterial mass is observed every 24 hours until the culture dish is full of the bacterial mass of the control group, and the diameters of the bacterial mass of the control group and the bacterial mass of the experimental group are measured by using a ruler.
3.4.3 method of calculating drug efficacy
Growth inhibition (%) was (control colony diameter-treated colony diameter)/(control colony diameter-5 mm) × 100%
3.5 results and analysis
The test results are shown in Table 5.
TABLE 5 preventive and therapeutic effects on gray mold of the compounds represented by the formula (1)
The active ingredient compound provided in test example 3 had a good inhibitory effect against Botrytis cinerea. For example, the bacteriostasis rate of the benzoyl formic acid to botrytis cinerea is 78% when the benzoyl formic acid is diluted by 400 times; the bacteriostasis rate of dibenzoyl methane to botrytis cinerea is 84% when the dibenzoyl methane is diluted by 200 times; 2, 4-carbonyl methyl phenylbutyrate is 600 times to 400 times diluted, the bacteriostasis rate is improved from 58% to 82% along with the increase of concentration, certain concentration dependence is shown, when the concentration is 200 times diluted, the bacteriostasis rate is not obviously improved, and the concentration dependence is reduced.
Test example 4
Experiment of preventing and treating corn northern leaf blight with the compound liquid medicine of formula (1).
4.1. Purpose of the experiment
The control effect and the dosage of the liquid medicine of the compound shown in the formula (1) on the corn northern leaf blight are improved.
4.2. Test conditions and test objects
4.2.1 test subjects
Northern leaf blight of corn.
The preparation method is the same as example 1.
4.2.2 test Environment
The test is carried out in the agricultural laboratory of Qinghua Changsheng research institute of the Asia-Tailu Zhejiang province in the southern lake region of Jiaxing city, Zhejiang, 2019 from 10 months to 11 months.
The strain used in the test is from the microbiological laboratory of Zhejiang university.
4.3 test design and arrangement
4.3.1 test Agents
A compound of formula (1) of example 1 in liquid form.
4.3.2 control Agents
The control used an equal amount of acetone.
The dosage of each liquid medicine is shown in table 2.
4.3.3 Medium usage and repetition
Culture medium: 8 ml.
The number of repetitions: each concentration was repeated 3 times.
4.4 test methods
4.4.1 methods of use: pouring 8ml of culture medium into a culture dish, inoculating pathogenic fungi onto the culture medium after the culture medium is solidified, putting a filter paper sheet with a medicament after the fungi grow to a certain size, and putting the culture medium in a constant-temperature incubator to observe the growth state of the fungi.
4.4.2 Observation methods
The growth of the bacterial mass is observed every 24 hours until the culture dish is full of the bacterial mass of the control group, and the diameters of the bacterial mass of the control group and the bacterial mass of the experimental group are measured by using a ruler.
4.4.3 method for calculating drug efficacy
Growth inhibition (%) was (control colony diameter-treated colony diameter)/(control colony diameter-5 mm) × 100%
4.5 results and analysis
The test results are shown in Table 6.
TABLE 6 preventive and therapeutic effects on northern leaf blight by Compounds of formula (1)
The active ingredient compound provided in test example 4 has a good inhibitory effect on northern leaf blight. For example, the bacteriostasis rate is 74% when the benzoylformic acid is diluted by 400 times; the inhibition rate of dibenzoyl methane on corn northern leaf blight is 86% when the dibenzoyl methane is diluted by 200 times; the inhibition rate of the 1, 3-cyclopentanedione diluted by 400 times to the corn northern leaf blight is 80%; the 2, 4-carbonyl methyl phenylbutyrate is diluted by 600 times to 400 times, the bacteriostasis rate is improved along with the increase of the concentration, certain concentration dependence is shown, and the bacteriostasis effect is good.
Test example 5
Experiment of preventing fusarium graminearum with the compound liquid medicine of formula (1).
5.1. Purpose of the experiment
The control effect and the dosage of the liquid medicine of the compound shown in the formula (1) on fusarium graminearum are improved.
5.2 test conditions, test subjects
5.2.1 test subjects
Fusarium graminearum.
The preparation method is the same as example 1.
5.2.2 test Environment
The test is carried out in the agricultural laboratory of Qinghua Changsheng research institute of the Asia-Tailu Zhejiang province in the southern lake region of Jiaxing city, Zhejiang, 2019 from 10 months to 11 months.
The strain used in the test is from the microbiological laboratory of Zhejiang university.
5.3 test design and arrangement
5.3.1 Agents
A compound of formula (1) of example 1 in liquid form.
5.3.2 control Agents
The control used an equal amount of acetone.
The dosage of each liquid medicine is shown in table 2.
5.3.3 Medium consumption and number of repetitions
Culture medium: 8 ml.
The number of repetitions: each concentration was repeated 3 times.
5.4 test methods
5.4.1 methods of use: pouring 8ml of culture medium into a culture dish, inoculating pathogenic fungi onto the culture medium after the culture medium is solidified, putting a filter paper sheet with a medicament after the fungi grow to a certain size, and putting the culture medium in a constant-temperature incubator to observe the growth state of the fungi.
5.4.2 Observation methods
The growth of the bacterial mass is observed every 24 hours until the culture dish is full of the bacterial mass of the control group, and the diameters of the bacterial mass of the control group and the bacterial mass of the experimental group are measured by using a ruler.
5.4.3 method for calculating drug effect
Growth inhibition (%) was (control colony diameter-treated colony diameter)/(control colony diameter-5 mm) × 100%
5.5 results and analysis
The test results are shown in Table 7.
TABLE 7 preventive and therapeutic effects of a compound represented by the formula (1) on Fusarium graminearum
The active ingredient compound provided in test example 5 has a good inhibitory effect on fusarium graminearum. For example, the bacteriostasis rate of the benzoylformic acid is 83% when the benzoylformic acid is diluted by 400 times; the bacteriostasis rate of the dibenzoyl methane diluted by 200 times is 87%; the 2, 4-carbonyl methyl phenylbutyrate is diluted from 600 times to 400 times, the bacteriostasis rate is improved from 62% to 85% along with the increase of the concentration, certain concentration dependence is shown, when the methyl phenylbutyrate is diluted to 200 times, the bacteriostasis rate is not obviously improved, and the concentration dependence is reduced.
Although the invention has been described in detail hereinabove with respect to a general description and specific embodiments thereof, it will be apparent to those skilled in the art that modifications or improvements may be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (8)
1. The invention includes the use of the pesticide compound or the pesticide for the control of fungal diseases.
2. The control objects include rice, corn, wheat, soybean, rape, sesame, Chinese cabbage, melon, eggplant, green soybean, cucumber, strawberry, etc.
3. The plant fungal diseases comprise rhizoctonia solani, fusarium oxysporum, botrytis cinerea, northern leaf blight, fusarium graminearum and the like.
4. The invention is to protect the compound of the formula (1)
A compound of the general structural formula.
5. The active ingredients include 2, 4-carbonyl benzene methyl butyrate, benzoyl formic acid, dibenzoyl methane, 1, 3-cyclopentanedione, methyl 2-chloro-A, G-Dioxo-benzene methyl butyrate, 1, 3-acetone dicarboxylic acid, 4, 6-dioxy-6-phenylhexanoic acid, 6-Hydroxy-1-phenyl-1, 3-hexanedione and 6-Hydroxy-1- (4-methylphenyl) -1, 3-dione.
6. The invention provides a pesticide which can be prepared from the compounds independently, can also be prepared from the compounds in a compounding way or can be prepared from the compounds and auxiliary agents or carriers in the field of pesticides, and other combinations which are not in the specification are also in the protection scope of the patent.
7. In a specific embodiment of the invention, the content of active ingredients in the pesticide compound is 50: 1-50: 5.
8. The content of the active ingredients in the pesticide compound is 1: 900-900: 1, preferably 60: 1-1: 50; further preferably 55: 1-50: 10; more preferably 50: 1 to 50: 5.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115536537A (en) * | 2022-09-21 | 2022-12-30 | 华中农业大学 | Propranolol derivative and application thereof in inhibiting phytopathogen |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6060074A (en) * | 1994-03-14 | 2000-05-09 | Morse Enterprises Limited, Inc. | Method of controlling fungus |
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2020
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6060074A (en) * | 1994-03-14 | 2000-05-09 | Morse Enterprises Limited, Inc. | Method of controlling fungus |
Non-Patent Citations (1)
| Title |
|---|
| CAS数据库: "登记号为451485-68-0等的化合物", REGISTRY, pages 1 - 6 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115536537A (en) * | 2022-09-21 | 2022-12-30 | 华中农业大学 | Propranolol derivative and application thereof in inhibiting phytopathogen |
| CN115536537B (en) * | 2022-09-21 | 2023-09-22 | 华中农业大学 | Propranolol derivative and application thereof in inhibiting plant pathogenic bacteria |
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