CN114208835A - Application of 3-trifluoromethylpyrazole compounds in preventing and treating agricultural fungal diseases - Google Patents
Application of 3-trifluoromethylpyrazole compounds in preventing and treating agricultural fungal diseases Download PDFInfo
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- CN114208835A CN114208835A CN202111579697.9A CN202111579697A CN114208835A CN 114208835 A CN114208835 A CN 114208835A CN 202111579697 A CN202111579697 A CN 202111579697A CN 114208835 A CN114208835 A CN 114208835A
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- trifluoromethylpyrazole
- fungal diseases
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
Abstract
The invention belongs to the technical field of pesticides, and particularly relates to application of 3-trifluoromethylpyrazole compounds with the following structural general formula in prevention and treatment of agricultural fungal diseases, wherein the compound has the structural general formula:
in the general formula (I), R1Selected from p-fluorophenyl, p-methylphenyl, p-methoxyphenyl,
Or
R2Selected from hydrogen atom, glycine hydrochloride, alanine hydrochloride, beta-alanine hydrochloride,
Or
Compared with the traditional agricultural bactericide, the compound provided by the invention has a unique structure, an action mechanism different from that of the existing bactericide, and no cross resistance risk for generating resistant strains for the existing bactericide.
Description
Technical Field
The invention belongs to the technical field of pesticides, and particularly relates to application of 3-trifluoromethylpyrazole compounds in prevention and treatment of agricultural fungal diseases.
Background
The 3-trifluoromethylpyrazole compound AR-12 (shown in the following figure) is a kinase inhibitor, and can effectively inhibit the growth of cancer cells such as prostate, breast cancer, liver cancer and the like.
In the prior art, the compound used as AR-12 is low in activity of antifungal pesticides, and the inhibition rate of the compound on common fungal pathogens is 20-30% at the concentration of 100ppm (see table 2), so that the high-activity agricultural fungicide needs to be invented through structural modification.
Disclosure of Invention
The invention provides application of a high-activity 3-trifluoromethylpyrazole compound with a structure shown as a general formula (I) in preventing and treating agricultural fungal diseases.
The invention adopts the following technical scheme:
the application of the 3-trifluoromethylpyrazole compound in preventing and treating agricultural fungal diseases is shown in the general formula (I):
in the general formula (I), R1Selected from p-fluorophenyl, p-methylphenyl, p-methoxyphenyl,
R2Selected from hydrogen atom, glycine hydrochloride, alanine hydrochloride, beta-alanine hydrochloride,
The compounds having anti-agricultural fungal activity of the present invention are illustrated by the specific compounds listed in table 1, but are not intended to limit the present invention.
TABLE 13 trifluoromethylpyrazoles
When the above-mentioned 3-trifluoromethylpyrazole compound is used for controlling agricultural fungal diseases, a more preferable compound is a compound represented by the formula (7), the formula (11) or the formula (12):
when the 3-trifluoromethylpyrazole compound is applied to control of agricultural fungal diseases, the most preferable compound is a compound represented by the formula (11):
the 3-trifluoromethyl pyrazole compound can be used for preparing a bactericide and has a good control effect on diseases caused by various germs such as phytophthora root rot of cabbage, small leaf spot of corn, scab of wheat, fusarium wilt of watermelon and the like.
Compared with the prior art, the invention has the beneficial effects that:
(1) the 3-trifluoromethylpyrazole compound provided by the invention has high-efficiency bactericidal activity compared with a lead compound AR-12. Has better prevention and treatment effects on phytophthora blight of Chinese cabbage, corn small leaf spot, wheat scab or watermelon fusarium wilt. The inhibition rate of the high-activity compound (the compound shown in the formula 11) under the concentration of 100ppm can reach 100%.
(2) The compound provided by the invention is different from any bactericide in the market, so that the cross resistance risk does not exist for the generation of resistant strains of the existing bactericide.
Drawings
FIG. 1 shows the inhibitory effect of compounds 7, 11, 12 and a control compound on several phytopathogens. The plant pathogenic bacteria a, b, c and d are watermelon fusarium wilt, wheat scab, cabbage phytophthora blight and corn small spot disease respectively.
Detailed Description
Embodiments of the present invention are further described. The following examples are intended to better illustrate the technical solutions of the present invention, but not to limit the scope of the present invention.
The 3-trifluoromethylpyrazole compound prepared by the invention has better control effect on agricultural fungal diseases, and is explained in more detail by the following examples, but the protection scope of the invention is not limited by the following examples.
Example 1
Determination of biological activity of 3-trifluoromethylpyrazole compound at concentration of 100ppm
The inhibition effect of the compounds on crop pathogenic bacteria under indoor conditions is determined as follows: the assay was performed by agar plate culture.
Compounds were diluted with dimethyl sulfoxide (DMSO) to a concentration of 10000. mu.g/mL of mother liquor, respectively.
Adding 10mL of agar culture medium (PDA) into a culture dish, then respectively adding 0.1mL of mother liquor of the compound with the concentration of 10000 mug/mL, and vibrating in parallel to uniformly mix the mother liquor and the culture medium to obtain a culture medium plate with the concentration of the compound of the invention of 100 mug/mL; negative control dishes were supplemented with 0.1mL of dimethyl sulfoxide (DMSO) without the compound of the invention, and each treatment was repeated three times. In addition, control compounds of the formula were also compared together:
and taking activated pathogenic bacteria cakes, respectively putting the activated pathogenic bacteria cakes into the center of a prepared culture medium plate in each culture dish, putting 1 bacterial cake into each culture dish, carrying out inverted culture in a constant-temperature incubator at 25 ℃, measuring the diameter of a bacterial colony by adopting a cross method after culturing for 60 hours, and calculating the average growth diameter and the hypha growth inhibition rate of the bacterial colony.
Wherein the colony growth diameter is the colony diameter-the cake diameter;
the hypha growth inhibition ratio (control colony growth diameter-drug-treated colony growth diameter)/control colony growth diameter × 100%.
The method is used for measuring the inhibition rate of the compounds on the hypha growth of pathogenic bacteria. The pathogenic bacteria are phytophthora infestans of Chinese cabbage, corn small leaf spot, wheat fusarium graminearum, watermelon fusarium oxysporum and the like.
The hyphal growth inhibition rates for the four pathogenic bacteria at 100ppm concentrations of the different compounds are shown in Table 2:
TABLE 2 inhibition of hyphal growth of four pathogenic bacteria at 100ppm concentration of different compounds
The above-mentioned embodiments are only for explaining the present invention, and not for limiting the implementation scope of the present invention, and it is obvious to those skilled in the art that other embodiments can be easily made by replacing or changing the technical content disclosed in the present specification, so that the changes and modifications made by the principles and process conditions of the present invention should be included in the claims of the present invention.
Claims (4)
- The application of the 3-trifluoromethyl pyrazole compound in preventing and treating agricultural fungal diseases is characterized in that the structure of the compound is shown as the general formula (I):
in the general formula (I), R1Selected from p-fluorophenyl, p-methylphenyl, p-methoxyphenyl,
R2Selected from hydrogen atom, glycine hydrochloride, alanine hydrochloride, beta-alanine hydrochloride,
- 2. The use of 3-trifluoromethylpyrazole compounds according to claim 1 for controlling agricultural fungal diseases, characterized in that the structural formula of the compounds is formula (7), formula (10) or formula (11):
- 3. the use of 3-trifluoromethylpyrazole compounds according to claim 2 for controlling agricultural fungal diseases, characterized in that the structural formula of the compounds is formula (11):
- 4. the use of 3-trifluoromethylpyrazole compounds according to claim 1 for controlling agricultural fungal diseases, characterized in that the fungal diseases are phytophthora blight of cabbage, northern leaf blight, wheat scab, or watermelon fusarium wilt.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202111579697.9A CN114208835B (en) | 2021-12-22 | 2021-12-22 | Application of 3-trifluoromethylpyrazole compound in preventing and treating agricultural fungal diseases |
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| CN202111579697.9A CN114208835B (en) | 2021-12-22 | 2021-12-22 | Application of 3-trifluoromethylpyrazole compound in preventing and treating agricultural fungal diseases |
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| CN114208835A true CN114208835A (en) | 2022-03-22 |
| CN114208835B CN114208835B (en) | 2023-04-11 |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005037271A2 (en) * | 2003-10-17 | 2005-04-28 | Tanabe Seiyaku Co., Ltd. | Large conductance calcium-activated k channel opener |
| JP2006316054A (en) * | 2005-04-15 | 2006-11-24 | Tanabe Seiyaku Co Ltd | High-conductance type calcium-sensitive k channel opening agent |
| CN108849912A (en) * | 2018-07-26 | 2018-11-23 | 河南省农业科学院植物保护研究所 | Application of the 1,5- diaryl -3- trifluoromethyl pyrazol class compound in prevention and treatment agricultural fungal diseases |
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2021
- 2021-12-22 CN CN202111579697.9A patent/CN114208835B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005037271A2 (en) * | 2003-10-17 | 2005-04-28 | Tanabe Seiyaku Co., Ltd. | Large conductance calcium-activated k channel opener |
| JP2006316054A (en) * | 2005-04-15 | 2006-11-24 | Tanabe Seiyaku Co Ltd | High-conductance type calcium-sensitive k channel opening agent |
| CN108849912A (en) * | 2018-07-26 | 2018-11-23 | 河南省农业科学院植物保护研究所 | Application of the 1,5- diaryl -3- trifluoromethyl pyrazol class compound in prevention and treatment agricultural fungal diseases |
Non-Patent Citations (1)
| Title |
|---|
| GEN LI等: "P(III)/P(V)-Catalyzed Methylamination of Arylboronic Acids and Esters: Reductive C−N Coupling with Nitromethane as a Methylamine Surrogate", 《JACS》 * |
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