CN114208835B - Application of 3-trifluoromethylpyrazole compound in preventing and treating agricultural fungal diseases - Google Patents
Application of 3-trifluoromethylpyrazole compound in preventing and treating agricultural fungal diseases Download PDFInfo
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- CN114208835B CN114208835B CN202111579697.9A CN202111579697A CN114208835B CN 114208835 B CN114208835 B CN 114208835B CN 202111579697 A CN202111579697 A CN 202111579697A CN 114208835 B CN114208835 B CN 114208835B
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- trifluoromethylpyrazole
- fungal diseases
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- 208000031888 Mycoses Diseases 0.000 title claims abstract description 13
- -1 3-trifluoromethylpyrazole compound Chemical class 0.000 title claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- PYXNITNKYBLBMW-UHFFFAOYSA-N 5-(trifluoromethyl)-1h-pyrazole Chemical class FC(F)(F)C1=CC=NN1 PYXNITNKYBLBMW-UHFFFAOYSA-N 0.000 claims description 6
- 235000012828 Citrullus lanatus var citroides Nutrition 0.000 claims description 5
- 241000209140 Triticum Species 0.000 claims description 5
- 235000021307 Triticum Nutrition 0.000 claims description 5
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims description 4
- 241000223218 Fusarium Species 0.000 claims description 4
- 241000233614 Phytophthora Species 0.000 claims description 4
- 206010039509 Scab Diseases 0.000 claims description 4
- 240000007124 Brassica oleracea Species 0.000 claims description 3
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 claims description 3
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 claims description 3
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 claims description 3
- 244000241235 Citrullus lanatus Species 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 8
- 239000003899 bactericide agent Substances 0.000 abstract description 7
- 239000000575 pesticide Substances 0.000 abstract description 3
- ILYVXUGGBVATGA-DKWTVANSSA-N (2s)-2-aminopropanoic acid;hydrochloride Chemical compound Cl.C[C@H](N)C(O)=O ILYVXUGGBVATGA-DKWTVANSSA-N 0.000 abstract description 2
- IVLXQGJVBGMLRR-UHFFFAOYSA-N 2-aminoacetic acid;hydron;chloride Chemical compound Cl.NCC(O)=O IVLXQGJVBGMLRR-UHFFFAOYSA-N 0.000 abstract description 2
- PDLNHDSYGLTYDS-UHFFFAOYSA-N 3-aminopropanoic acid;hydrochloride Chemical compound Cl.NCCC(O)=O PDLNHDSYGLTYDS-UHFFFAOYSA-N 0.000 abstract description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 abstract description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 abstract description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 abstract description 2
- 206010034133 Pathogen resistance Diseases 0.000 abstract description 2
- 229960001269 glycine hydrochloride Drugs 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 244000052616 bacterial pathogen Species 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 230000012010 growth Effects 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 241000219109 Citrullus Species 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- 239000001963 growth medium Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 2
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 2
- 235000000536 Brassica rapa subsp pekinensis Nutrition 0.000 description 2
- 241000499436 Brassica rapa subsp. pekinensis Species 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 230000009036 growth inhibition Effects 0.000 description 2
- 230000028644 hyphal growth Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000223195 Fusarium graminearum Species 0.000 description 1
- 241000223221 Fusarium oxysporum Species 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 244000000005 bacterial plant pathogen Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000005907 cancer growth Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000002888 effect on disease Effects 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229940043355 kinase inhibitor Drugs 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
Images
Classifications
-
- 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
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention belongs to the technical field of pesticides, and particularly relates to a 3-trifluoromethylpyrazole compound with the following structural general formulaThe application of the compound in preventing and controlling agricultural fungal diseases is that the structural general formula of the compound is as follows:
in the general formula (I), R 1 Selected from p-fluorophenyl, p-methylphenyl, p-methoxyphenyl,
Or
R 2 Selected 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 as an antifungal pesticide, 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 bactericide 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), R 1 Selected from p-fluorophenyl, p-methylphenyl, p-methoxyphenyl,
R 2 Selected 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 1 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 following formula were also compared together:
and (3) taking the activated pathogenic bacteria cakes, respectively putting the activated pathogenic bacteria cakes into the centers of prepared culture medium plates in the culture dishes, putting 1 fungus cake into each culture dish, carrying out inverted culture in a constant-temperature incubator at 25 ℃, measuring the diameters of the colonies by adopting a cross method after culturing for 60 hours, and calculating the average growth diameter and the hypha growth inhibition rate of the colonies.
Wherein, colony growth diameter = colony diameter-cake diameter;
hypha growth inhibition = (control colony growth diameter-agent-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 used for explaining the present invention, and do not limit the 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 contents disclosed in the present specification, and therefore, the changes and modifications made by the principles and process conditions of the present invention should be included in the scope of the present invention.
Claims (3)
- The application of the 3-trifluoromethyl pyrazole compound in preventing and treating agricultural fungal diseases is characterized in that,the structural formula of the compound is formula (7), formula (11) or formula (12):
- 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 (11):
- 3. 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.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111579697.9A CN114208835B (en) | 2021-12-22 | 2021-12-22 | Application of 3-trifluoromethylpyrazole compound in preventing and treating agricultural fungal diseases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114208835A CN114208835A (en) | 2022-03-22 |
| CN114208835B true CN114208835B (en) | 2023-04-11 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111579697.9A Active CN114208835B (en) | 2021-12-22 | 2021-12-22 | Application of 3-trifluoromethylpyrazole compound in preventing and treating agricultural fungal diseases |
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| CN (1) | CN114208835B (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007518686A (en) * | 2003-10-17 | 2007-07-12 | 田辺製薬株式会社 | High conductance calcium-sensitive K channel opener |
| JP2006316054A (en) * | 2005-04-15 | 2006-11-24 | Tanabe Seiyaku Co Ltd | High-conductance type calcium-sensitive k channel opening agent |
| CN108849912B (en) * | 2018-07-26 | 2020-06-30 | 河南省农业科学院植物保护研究所 | Application of 1, 5-diaryl-3-trifluoromethylpyrazole compound in preventing and treating agricultural fungal diseases |
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- 2021-12-22 CN CN202111579697.9A patent/CN114208835B/en active Active
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