WO2019120218A1

WO2019120218A1 - Pyrazole amide compound, application thereof, and microbicide

Info

Publication number: WO2019120218A1
Application number: PCT/CN2018/122050
Authority: WO
Inventors: 杨光富; 李华
Original assignee: 华中师范大学
Priority date: 2017-12-22
Filing date: 2018-12-19
Publication date: 2019-06-27
Also published as: CN109956904A; CN109956904B

Abstract

A pyrazole amide microbicide, having a structural formula of N-[2-[2-bromo-4-(trifluoromethyl)phenoxy]phenyl]-1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide. The microbicide has significant control effect against soybean rust, corn rust, wheat powdery mildew, and cucumber powdery mildew.

Description

Pyrazole amide compounds and their use and fungicides

Technical field

The invention relates to the field of pesticide bactericides, in particular to a pyrazole amide compound and application thereof, and a bactericide containing the pyrazole amide compound.

Background technique

The bactericides targeting succinate dehydrogenase (SDH, succinate dehydrogenase) are currently the most important class of fungicides. This type of fungicide kills the pathogen by inhibiting the activity of the pathogen succinate dehydrogenase. The purpose of disease prevention.

Because this kind of fungicide has a novel mechanism of action, it has no cross-resistance with most fungicides on the market, and thus has become a hot spot for the major pesticide companies in the world.

Among these fungicides, pyrazole amides are the most abundant of the listed varieties. Because of their wide spectrum of bactericidal activity and high activity, they are able to control a variety of crop diseases in agricultural production. The most widely studied class of succinate dehydrogenase inhibitors is currently under investigation.

For example, CN1226244A and CN101056858A respectively disclose the general formula of a pyrazole amide compound used as a bactericide, and in the examples, some pyrazole amide specific compounds containing a diphenyl ether structure are disclosed.

Further, CN 1226244 A discloses the following two pyrazole amide compounds 12 and 21 having a diphenyl ether structure.

CN101056858A discloses the structure of pyrazole amide derivatives containing hydrazine-substituted diphenyl ether.

As another example, CN104557709A discloses two compounds having the following structural features.

Soybean rust, corn rust, wheat powdery mildew and cucumber powdery mildew are major diseases that endanger agricultural production, although commercially available pyrazole amide succinate dehydrogenase inhibitors have bactericidal one or more of the above diseases. Pyrazole amide succinate dehydrogenase inhibitors which are active but which are capable of simultaneously controlling these major diseases at very low concentrations have not been discovered.

For example, it has been found by biological activity tests that the compounds disclosed in CN1226244A, CN101056858A and CN104557709A have better control effects against soybean rust, corn rust, wheat powdery mildew or cucumber powdery mildew only at higher concentrations. The compounds disclosed in the above prior art are less effective against soybean rust or corn rust when the drug concentration is lowered. However, the high concentration of the drug first causes the problem of increased cost, and secondly, the safety of the drug is also significantly reduced.

Summary of the invention

The object of the present invention is to overcome the poor control effect of the pyrazole amide compound of diphenyl ether provided by the prior art on soybean rust, corn rust, wheat powdery mildew and cucumber powdery mildew or the control of soybean rust at low concentration. A very poor defect provides a new pyrazole amide compound with excellent control against soybean rust, corn rust, wheat powdery mildew and cucumber powdery mildew even at low concentrations.

The inventors of the present invention found in the study that the diphenyl ether-containing pyrazole amide compound has a diphenyl ether structural substituent type and a substitution position for soybean rust, corn rust, wheat powdery mildew and cucumber powdery mildew. Bactericidal activity has an important effect. Specifically, when the diphenyl ether structure of the pyrazole amide compound of the diphenyl ether has a substituent of a bromine atom and a trifluoromethyl group, and the bromine atom is in the ortho position of the terminal benzene ring in the diphenyl ether structure, the trifluoro group When the methyl group is in the para position of the terminal benzene ring in the diphenyl ether structure, and the 5-position of the pyrazole ring is substituted without a fluorine atom, the formed compound (hereinafter also referred to as the compound of the present invention) is used for controlling soybean. When at least one of rust, corn rust, wheat powdery mildew, and cucumber powdery mildew is used, even at a low drug concentration, a good control effect can be obtained.

In particular, benzene fluconazole is currently a heavy product for the treatment of Asian soybean rust, however, the inventors of the present invention unexpectedly found in the study that the compound of the present invention is resistant to soybean rust and benzene fluoride At present, due to the large amount of irrational use of benzotrifenazole, benzotrifen-resistant strains have appeared in Brazil and other regions. Therefore, the development of novel and highly efficient agents for the control of soybean rust Diseases are of great significance. Based on the above findings, the inventors of the present invention have completed the technical solution of the present invention.

In order to achieve the above object, a first aspect of the invention provides a pyrazole amide compound having a structure represented by the following formula (1):

A second aspect of the invention provides the use of the compound of the first aspect described above for controlling soybean rust.

A third aspect of the invention provides the use of the compound of the first aspect described above for controlling corn rust.

A fourth aspect of the invention provides the use of the compound of the first aspect described above for controlling wheat powdery mildew.

A fifth aspect of the invention provides the use of the compound of the first aspect described above for controlling cucumber powdery mildew.

A sixth aspect of the invention provides the use of the compound of the first aspect described above for the preparation of a pesticide for controlling at least two diseases of soybean rust, corn rust, wheat powdery mildew and cucumber powdery mildew.

Particularly preferably, the present invention provides the use of the compound of the first aspect described above for the simultaneous control of soybean rust, corn rust, wheat powdery mildew and cucumber powdery mildew.

A seventh aspect of the invention provides a bactericide which is composed of an active ingredient and an auxiliary material, the active ingredient comprising the pyrazole amide compound of the first aspect of the invention.

Preferably, the active ingredient is present in an amount from 1 to 99.9% by weight.

Preferably, the dosage form of the bactericide is at least one selected from the group consisting of an emulsifiable concentrate, a suspending agent, a wettable powder, a powder, a granule, a liquid, a bait, a mother liquor, and a mother powder.

The pyrazole amide compound of the structure represented by the formula (1) provided by the present invention has good control effects against soybean rust, corn rust, wheat powdery mildew and cucumber powdery mildew at a low concentration.

Another important research significance of the present invention is that the compound of the present invention has good control effect against wheat powdery mildew, cucumber powdery mildew and soybean rust by field experiment data. It is known to those skilled in the art that the new pesticide-initiating compounds are firstly subjected to greenhouse potting screening, and it is found through indoor verification that the compound having high activity enters the field test. However, due to the more complex factors in the field trials (such as temperature, light, rain, soil, etc.), many of the high-activity compounds found in greenhouse screening failed to show excellent results when they entered the field trial. For example, the fungicide enestrobin showed extremely high activity against wheat powdery mildew when screened indoors, but when it entered the field trial, the difference between its control effect and indoor activity was significant. Therefore, there are few compounds that can exhibit excellent control effects after entering the field test through indoor screening. The discovery of compounds that still exhibit excellent control during field trials is often required to be discovered by researchers with a lot of creative labor.

Specifically, the field experiment data of the present invention confirmed that the compound of the present invention is significantly more effective against wheat powdery mildew, cucumber powdery mildew, and soybean rust than the current main commercial chemicals for the aforementioned crop diseases, or the present invention. The control effect of the compound on wheat powdery mildew, cucumber powdery mildew and soybean rust is equivalent to the current control effect of the main commercial chemicals for the aforementioned crop diseases.

Detailed ways

The endpoints and any values of the ranges disclosed herein are not limited to the precise range or value, and such ranges or values should be understood to include values that are close to the ranges or values. For numerical ranges, the endpoint values of the various ranges, the endpoint values of the various ranges and the individual point values, and the individual point values can be combined with one another to yield one or more new ranges of values. The scope should be considered as specifically disclosed herein.

The method for producing a pyrazole amide compound having a structure represented by the formula (1) is not particularly limited, and for example, a pyrazole amide compound having a structure represented by the formula (1) can be produced by the following synthetic route:

When the pyrazole amide compound having the structure represented by the formula (1) provided by the present invention is used for controlling soybean rust, corn rust, wheat powdery mildew or cucumber powdery mildew, the pyrazole amide compound having the structure represented by the formula (1) can be used. The substance is distributed as an active ingredient into a pesticidal composition, and is applied to the crop in a controlled amount.

The excipients in the bactericide of the present invention may be conventional excipients used in the art for forming various suitable dosage forms including, but not limited to, surfactants and the like.

The invention will be described in detail below by way of examples. The various reagents described in the following examples are commercially available without particular explanation.

Example 1

The pyrazole amide compound of the structure represented by the formula (1) (that is, the following compound 1) is prepared by the synthetic route described above according to the present invention, specifically as follows:

(1) Preparation of the compound shown in 1-3

3 mmol of the compound represented by 1-2, 3.3 mmol of the compound represented by 1-1, and 3.6 mmol of potassium carbonate were added to a 50 mL round bottom flask, and then 20 mL of DMF was added thereto, and the temperature was raised to 100 ° C, and the reaction of the starting material was monitored by TLC. After the reaction was stopped, 50 mL of ethyl acetate was added, and the mixture was washed twice with 50 mL of brine, dried over anhydrous sodium sulfate and evaporated.

Brown ^{liquid, 1 H NMR (600MHz, DMSO} ) δ8.07 (s, 1H), 7.68 (d, J = 8.6Hz, 1H), 7.05-7.00 (m, 1H), 6.88 (dd, J = 8.1,1.6 Hz, 2H), 6.77 (d, J = 8.7 Hz, 1H), 6.62 - 6.58 (m, 1H), 5.03 (s, 2H). GC-MS: m/z 331.14 [M] ⁺ .

(2) Preparation of a compound represented by Formula 1

2 mmol of the compound represented by 1-3 was dissolved in 20 mL of dichloromethane, 3 mmol of triethylamine was added, and the compound shown by 1-4 (2.4 mmol) was slowly added dropwise under ice-cooling. After the TLC monitoring reaction was completed, 30 mL of dichloromethane was added to the system, and the mixture was washed three times with 50 mL of saturated brine, dried over anhydrous sodium sulfate, and purified by column chromatography to give the compound of formula 1 in a yield of 56%.

White powder, ¹ H NMR (600 MHz, DMSO) δ 9.67 (s, 1H), 8.36 (s, 1H), 8.07 (d, J = 2.0 Hz, 1H), 7.73 (ddd, J = 10.8, 7.9, 3.4 Hz, 2H), 7.33–7.28 (m, 2H), 7.21 (t, J=54 Hz, 1H), 7.10–7.06 (m, 1H), 7.03 (d, J=8.6 Hz, 1H), 3.92 (s, 3H) .HRMS (MALDI) calcd for _{_{_{_{C 19 H 13 BrF 5 N 3}}}} O 2 [M + H] +: 490.01841, found 490.01674.

Test Example 1: Screening results of bactericidal activity

Test method: Each compound in Table 1 was formulated into a 5% by weight emulsifiable concentrate. The experiments were carried out in live pots, and the effective concentrations of the compounds are shown in Table 1.

Soy rust

The 2-leaf stage soybean potted seedlings with uniform growth were selected for foliar spray treatment, and a blank control of sprayed water was set up, repeated 3 times. Soybean rust spore suspension was inoculated on the second day after treatment. After inoculation, the artificial climate chamber (temperature: 20 ° C - 25 ° C, relative humidity: > 95%) was placed in moisturizing culture, and placed in a greenhouse after 8-16 hours (25 ° C ± 1 ° C). ) Normal management. After 7 days, the control effect was investigated when the blank control was sufficient.

Corn rust

The 2-3 leaf stage corn potted seedlings with uniform growth were selected, and the leaf surface spray treatment was carried out according to the designed concentration. A blank control of the sprayed water was additionally set, and the repetition was repeated three times. On the second day after the treatment, the corn rust spore suspension was inoculated. After inoculation, the artificial climate chamber (temperature: 昼25°C, night 20°C, relative humidity: 95～100%) was moisturized and cultured, and placed in the greenhouse after 24 hours (25°C±1). °C) Normal management. After 7 days, the control effect was investigated when the blank control was sufficient.

Wheat powdery mildew

The 2-potted wheat potted seedlings with uniform growth were selected, and the leaf surface spray treatment was carried out according to the designed concentration. A blank control of the sprayed water was additionally set up, and the repetition was repeated three times. On the second day after the treatment, the spores were shaken off, and the inoculated crops were placed in a greenhouse (25 °C ± 1 °C) for normal management. After 7 days, the control effect was investigated when the blank control was sufficient.

Cucumber powdery mildew

Choose a true leaf stage, grow the same cucumber seedlings, spray dry and dry for 24h. The fresh spores on the leaves of the powdery cucumbers were washed and filtered with double-layer gauze to prepare a suspension having a spore concentration of about 100,000/mL, which was inoculated by spraying. After the inoculation, the test materials were naturally air-dried, and then moved to the constant temperature room light (21-23 ° C). After 8 days, the incidence of the blank control was graded and the control effect was calculated according to the disease index.

Survey method: The grading standard adopts the “Pesticide Field Efficacy Test Guidelines”, and the disease prevention index is used to calculate the control effect%.

Disease index = ∑ (number of diseased leaves at each level × relative value) × 100 / (total number of leaves × 9);

Control effect (%) = (control disease index - treatment of disease index) × 100 / control disease index;

The test results are shown in Table 1.

The structural formulas of the compounds 2-11 used for comparison in Table 1 are as follows:

Table 1

"-" means not tested

As can be seen from the results in Table 1, the compounds provided by the present invention exhibited good control effects against corn rust, soybean rust, wheat powdery mildew and cucumber powdery mildew at low concentrations. In particular, the compounds provided by the present invention are significantly more effective against wheat powdery mildew and cucumber powdery mildew at lower concentrations than the compounds provided by the prior art.

Comparing the structural formulas of the compound 2 and the compound 4 with the compound provided by the present invention, it can be seen that the difference between the structures of the aforementioned compound 2 and the compound 4 and the compound provided by the present invention lies only in the freedom of the diphenyl ether of the compound 2 and the compound 4. The ortho substituents on the phenyl group are a chlorine atom and an iodine atom, respectively (the corresponding position of the compound provided by the present invention is a bromine atom), and the pyrazole ring of the compound 2 and the compound 4 has a fluorine atom substituent at the 5-position ( The corresponding positions of the compounds provided herein are free of fluorine atoms). It can be seen from the results in Table 1 that the compound 2 and the compound 4 have the same control effect on corn rust and soybean rust at a concentration of 25 mg/L or more, and the compound of the present invention is equivalent to the corresponding disease, but at a concentration of At 6.25 mg/L, the effects of Compound 2 and Compound 4 on corn rust and soybean rust are inferior to those of the compounds of the present invention against the corresponding diseases. Further, at the same concentration, the control effects of Compound 2 and Compound 4 on wheat powdery mildew and cucumber powdery mildew were significantly lower than those of the compounds of the present invention against wheat powdery mildew and cucumber powdery mildew. From this, it can be seen that the substitution type of the halogen atom on the free phenyl group of the diphenyl ether and the fluorine atom substitution at the 5-position of the pyrazole ring have an important influence on the effect and application range of the pyrazole amide compound.

It can be seen from the structural formula of the compound 3 and the compound provided by the present invention that the difference between the structure of the above compound 3 and the compound provided by the present invention is only that the pyrazole ring of the compound 3 contains a fluorine atom substituent at the 5-position. The corresponding positions of the compounds provided by the invention are free of fluorine atoms). It can be seen from the results in Table 1 that the compound 3 has a control effect on corn rust and soybean rust at a concentration of 25 mg/L or more, and the compound of the present invention is equivalent to the corresponding disease, but at a concentration of 6.25 mg/ At L, the control effect of Compound 3 on corn rust and soybean rust is inferior to that of the compound of the present invention against the corresponding diseases. Further, at the same concentration, the control effect of Compound 3 on wheat powdery mildew and cucumber powdery mildew was significantly lower than that of the compound of the present invention against wheat powdery mildew and cucumber powdery mildew. From this, it can be seen that the substitution of the fluorine atom at the 5-position of the pyrazole ring has an important influence on the effect and application range of the pyrazole amide compound.

Comparing the structural formulas of the compound 5, the compound 10 and the compound 11 with the compound provided by the present invention, it can be seen that the difference between the structures of the foregoing compound 5, compound 10 and compound 11 and the compound provided by the present invention is only in the diphenyl group of the compound 5. The ortho substituent on the free phenyl group of the ether is an iodine atom, the ortho substituent on the free phenyl group of the diphenyl ether of the compound 11 is a chlorine atom, and the ortho position substitution on the free phenyl group of the diphenyl ether of the compound 10 Both the base and the para substituent are chlorine atoms (the ortho substituent of the compound provided by the present invention is a bromine atom and the para substituent is a trifluoromethyl group). It can be seen from the results in Table 1 that the compound 5, the compound 10 and the compound 11 have the same control effect on corn rust and soybean rust at a concentration of 25 mg/L or more, and the compound of the present invention has the same effect on the corresponding disease, but At a concentration of 6.25 mg/L, Compound 5, Compound 10 and Compound 11 were less effective against corn rust than the compounds of the present invention against the corresponding diseases. Further, at the same concentration, the control effects of Compound 5, Compound 10 and Compound 11 on wheat powdery mildew and cucumber powdery mildew were significantly lower than those of the present invention against wheat powdery mildew and cucumber powdery mildew. From this, it can be seen that the type of the halogen atom substituent on the free phenyl group of the diphenyl ether has an important influence on the effect and application range of the pyrazole amide compound.

Comparing the structural formulas of the compound 6, the compound 8 and the compound provided by the present invention, it can be seen that the difference between the structures of the foregoing compound 6, the compound 8 and the compound provided by the present invention is only in the freedom of the diphenyl ether of the compound 6 and the compound 8. The 2,5-position substituent on the phenyl group is a trifluoromethyl group (the substitution position of the compound provided by the present invention is 2, 4-position, and the 2-position is a bromine atom substitution, and the 4-position is a trifluoromethyl substitution. Further, the pyrazole ring of the compound 8 further contains a fluorine atom substituent at the 5-position of the pyrazole ring. It can be seen from the results in Table 1 that when the concentration of the compound 6 and the compound 8 is 100 mg/L or more, the control effect on soybean rust is equivalent to the control effect of the compound of the present invention on the corresponding disease, but the concentration is less than 100 mg/ At L, the control effects of Compound 6 and Compound 8 on soybean rust are significantly inferior to those of the compounds of the present invention against the corresponding diseases. Further, at the same concentration, the control effects of Compound 6 and Compound 8 on wheat powdery mildew, soybean rust and cucumber powdery mildew were significantly lower than those of the compounds of the present invention against wheat powdery mildew, soybean rust and cucumber powdery mildew. From this, it can be seen that the type and substitution position of the substituent on the free phenyl group of the diphenyl ether and the substitution of the fluorine atom at the 5-position of the pyrazole ring have an important influence on the effect and application range of the pyrazole amide compound.

Comparing the structural formula of the compound 7 with the compound provided by the present invention, it can be seen that the difference between the structure of the aforementioned compound 7 and the compound provided by the present invention is only that the pyrazole ring of the compound 7 contains a fluorine atom substituent at the 5-position ( Whereas the compound of the invention does not have the substituent at the corresponding position), and the 2-position substituent on the free phenyl group of the diphenyl ether of compound 7 is a trifluoromethyl group (and the substituent of the compound of the invention at the corresponding position) Is a bromine atom). It can be seen from the results in Table 1 that the compound 7 has a control effect against corn rust and soybean rust at a concentration of 25 mg/L or more, and the compound of the present invention is equivalent to the corresponding disease, but at a concentration of 6.25 mg/ At L, compound 7 is less effective against corn rust and soybean rust than the compounds of the present invention against the corresponding diseases. Further, at the same concentration, the control effect of Compound 7 on wheat powdery mildew and cucumber powdery mildew was significantly lower than that of the compound of the present invention against wheat powdery mildew and cucumber powdery mildew. From this, it can be seen that the substitution of the fluorine atom at the 5-position of the pyrazole ring and the type of the substituent on the free phenyl group of the diphenyl ether have an important influence on the effect and application range of the pyrazole amide compound.

Comparing the structural formula of the compound 9 with the compound provided by the present invention, it can be seen that the difference between the structure of the aforementioned compound 9 and the compound provided by the present invention is only the 2-position substituent on the free phenyl group of the diphenyl ether of the compound 9. And the 4-position substituent are a trifluoromethyl group and a bromine atom, respectively (while the substituent of the compound of the present invention at the corresponding position is a bromine atom and a trifluoromethyl group, respectively). It can be seen from the results in Table 1 that the compound 9 has a control effect against corn rust and soybean rust at a concentration of 25 mg/L or more, and the compound of the present invention is equivalent to the corresponding disease, but at a concentration of 6.25 mg/ At L, the control effect of Compound 9 on corn rust and soybean rust is inferior to that of the compound of the present invention against the corresponding diseases. Further, at the same concentration, the control effect of Compound 9 on wheat powdery mildew and cucumber powdery mildew was significantly lower than that of the compound of the present invention against wheat powdery mildew and cucumber powdery mildew. It can be seen that the substitution position of the substituent on the free phenyl group of diphenyl ether has an important influence on the effect and application range of the pyrazole amide compound.

Test Example 2: Rescreening at a lower concentration

The compound provided by the present invention and a part of the compound for comparison were subjected to rescreening in the same manner as in Test Example 1. Unlike Test Example 1, the effective concentration of the compound in the test example is shown in Table 2.

The test results of this test example are shown in Table 2.

Table 2

"-" means not tested

It can be seen from the results in Table 2 that the compound 5, the compound 10 and the compound 11 have a control effect on soybean rust at a concentration of 3.125 mg/L or more, and the compound of the present invention is equivalent to the corresponding disease, but at a concentration When the amount is lower than 3.125 mg/L, the effects of the compound 5, the compound 10 and the compound 11 on soybean rust are inferior to those of the compound of the present invention against the corresponding diseases. Moreover, the control effects of Compound 5, Compound 10 and Compound 11 on cucumber powdery mildew at various concentrations were significantly inferior to those of the compounds of the present invention against the corresponding diseases. From this, it can be seen that the type of the substituent on the free phenyl group of the diphenyl ether has an important influence on the effect and application range of the pyrazole amide compound.

It can also be seen from the results in Table 2 that the compounds provided by the present invention are superior to azoxystrobin in the control of soybean rust and have comparable efficacy to prothioconazole and benzotrifluoxazole. Further, the compound of the present invention is superior to cucumber powdery mildew in the treatment of azoxystrobin, prothioconazole, benzotrifluzazole, difenoconazole and ethylpyrrol.

Test Example 3

Test method: host plant culture

The greenhouse is cultivated to a true leaf stage for use.

Test operation steps:

A sample of each compound was dissolved in dimethyl sulfoxide to prepare a mother liquor for use. During the test, the compound sample and the control medicinal 0.5% by weight Tween 80 water were formulated into a series concentration gradient liquid solution, and the host crop was subjected to foliar spray treatment, and then naturally dried, and the pathogen was inoculated 24 hours later. Soybean rust spore suspension (5-8×10 ⁶ /mL) was sprayed on the host crop with an inoculator, then transferred to an artificial climate chamber (24±2°C, RH>90, no light), after 16 hours Moved into the greenhouse for normal management. The test material was cultured for 7-15 days to investigate the bactericidal activity of the compound.

Survey method: The results of the survey refer to the "A Manual of Assessment Keys for Plant Diseases" prepared by the American Academy of Plant Diseases. According to the incidence of the control, the visual test method is used to investigate the bactericidal activity of the test sample, which is expressed by 100-0. "Grade represents disease-free and "0" level represents the most serious degree of disease.

The DPS evaluation system was used for analysis and evaluation, and the linear regression equation, the EC ₅₀ value, and the correlation coefficient (r) were calculated.

The specific results are shown in Table 3.

table 3

As can be seen from the results in Table 3, the compounds of the present invention provides a soybean rust prevention EC ₅₀ values were significantly lower than values of compounds 10 and ₅₀ Compound EC 11 control soybean rust. Therefore, the compound provided by the present invention has an excellent effect of controlling soybean rust.

Test Example 4

Test method: host plant culture

The greenhouse cultures the corn to a true leaf stage for use.

Test operation steps:

A sample of each compound was dissolved in dimethyl sulfoxide to prepare a mother liquor for use. During the test, the compound sample and the control medicinal 0.5% by weight Tween 80 water were formulated into a series concentration gradient liquid solution, and the host crop was subjected to foliar spray treatment, and then naturally dried, and the pathogen was inoculated 24 hours later. The corn rust spore suspension (5-8×10 ⁶ /mL) was sprayed on the host crop with an inoculator, and then transferred to an artificial climate chamber (24±2°C, RH>90, no light), 16 hours later. Moved into the greenhouse for normal management. The test material was cultured for 7-15 days to investigate the bactericidal activity of the compound.

The DPS evaluation system was used for analysis and evaluation, and the linear regression equation, EC ₉₀ value, and correlation coefficient (r) were calculated.

The specific results are shown in Table 4.

Table 4

As can be seen from the results of Table 4, EC ₉₀ values for the compounds of the present invention to provide corn rust prevention significantly lower than the EC ₉₀ value of Compound 10 and Compound 11 in corn rust prevention. Therefore, the compound provided by the present invention has an excellent effect of controlling corn rust.

Test Example 5: Field trial

I, cucumber powdery mildew test method:

Application method: stem and leaf spray (application equipment: Xin Kangda lithium battery electric spray).

Test crop: cucumber (variety: Tianjiao 7)

The test was carried out in Shenyang. The test site was loam, the organic matter content was rich, the fertilizer and water management was normal, and other fungicides were not used in the test field.

The arrangement of the test plots is random group arrangement; the area of the plot: 15 square meters; the number of repetitions: 3 times; the time and frequency of application: September 28, 2018 - October 11, 2018, a total of drugs 2 times. The amount of the drug solution applied was 3 repetitions per treatment, and 8 L of shared water was repeated 3 times. No other pesticides were applied during the test. The test was applied in sunny weather, and there was no rain 1 day after the drug. The effect was investigated 15-20 days after the second application.

Each plot was randomly selected for 4 points, and 2 strains were inspected at each point. All the leaves were investigated for each plant, and the area of the lesions on each leaf accounted for the percentage of the total leaf area.

Grading method (in blades):

Level 0: no lesions;

Level 1: The area of the lesion is less than 5% of the entire leaf area;

Level 3: The area of the lesions accounts for 6%-10% of the total leaf area;

Level 5: The area of the lesions accounts for 11%-20% of the total leaf area;

Level 7: The area of the lesions accounts for 21%-40% of the total leaf area;

Grade 9: The area of the lesions accounts for more than 40% of the total leaf area.

According to the "People's Republic of China National Standard Pesticide Field Test Guidelines", the disease index was calculated according to the grade, and the control effect was calculated according to the disease index. The DPS evaluation system (Duncan's new complex range method) was used to analyze the test data.

The results are shown in Table 5.

table 5

It can be seen from the results in Table 5 that the compound of the present invention has good control effect against cucumber powdery mildew from the control effect of the field test, and the compound of the present invention shows 50.27% against cucumber powdery mildew at a dose of 150 g/ha. The control effect is higher than the control effect of the important commercial agent, fluconazole, for controlling cucumber powdery mildew in agricultural production under the same dosage. At a dose of 225 g/ha, the compound of the present invention has a control effect against cucumber powdery mildew of more than 60%, which is a practical application value in agricultural production. It should be pointed out that the disease index of this test is as high as 82.74, which is a case of extremely serious disease, which fully demonstrates that the compound of the present invention has excellent control effect against cucumber powdery mildew and has obvious practical value.

II. Test methods for wheat powdery mildew:

Test crop: wheat (variety: Liaochun 10)

The arrangement of the test plots is random group arrangement; the area of the plot: 15 square meters; the number of repetitions: 3 times; the time and frequency of application: September 17, 2018, a total of 1 application. The amount of the drug solution applied was 3 repetitions per treatment, and 8 L of shared water was repeated 3 times. No other pesticides were applied during the test. The test was applied in sunny weather, and there was no rain 1 day after the drug.

Each plot was sampled at 5 points diagonally, and 20 strains were surveyed at each point. The first leaf under the flag leaf of each plant was investigated.

The disease grading standards are as follows:

Level 0: no disease;

Level 1: The area of the lesion is less than 5% of the total area of the blade;

Level 3: The area of the lesions accounts for 6%-25% of the total area of the leaves;

Level 5: The area of the lesions accounts for 26%-50% of the total area of the leaves;

Level 7: The area of the lesions accounts for 51%-75% of the total area of the leaves;

Grade 9: The area of the lesions accounts for 76%-100% of the total area of the leaves.

The results are shown in Table 6.

Table 6

It can be seen from the results in Table 6 that the compound of the present invention has excellent control effect against wheat powdery mildew from the control effect of the field test, and even at a low usage amount of 50 g/ha, the control effect of the compound of the present invention is still 92.34% was achieved, and the important commercial chemicals of the drug for the control of wheat powdery mildew in the agricultural production were significantly less effective than the compounds of the present invention at the same dosage. It should be noted that the disease index of this test exceeds 60, which is a very serious condition, which also fully demonstrates the excellent control effect of the compound of the present invention, indicating that the compound of the present invention has practical value.

III. Test method for soybean rust:

Test crop: soybean (variety: Liaodou 15)

The arrangement of the test plots is random group arrangement; the area of the plot: 25 square meters; the number of repetitions: 3 times; the time and frequency of application: August 11, 2018, August 21, a total of 2 times. The amount of the drug solution applied was 3 repetitions per treatment, and 8 L of shared water was repeated 3 times. No other pesticides were applied during the test. The test was applied in sunny weather, and there was no rain 1 day after the drug. The effect was investigated 15-20 days after the second application.

20 plots of five points were sampled by diagonal method in each plot, and 10 leaves were investigated per plant. Record the total number of leaves and the number of diseased leaves at each level.

The disease grading standards are as follows:

Level 0: no disease;

Level 1: The area of the lesion is less than 5% of the total area of the blade;

The results are shown in Table 7.

Table 7

The results show that the compound of the present invention has excellent control effect on soybean rust, and even at a low use amount of 50 g/ha, the control effect of the compound of the present invention is still more than 90%, and it is important for controlling soybean rust in agricultural production. The commercial agents, fluconazole and azoxystrobin, were significantly less effective than the compounds of the invention even at doses of 100 g/ha. It should be pointed out that the disease index of this test is as high as 85.48, which is a case of extremely serious disease, which fully demonstrates that the compound of the present invention has excellent control effect on soybean rust and has obvious practical value.

The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited thereto. Within the scope of the technical idea of the present invention, various simple modifications can be made to the technical solutions of the present invention, including various technical features combined in any other suitable manner, and these simple variations and combinations should also be regarded as the disclosure of the present invention. All fall within the scope of protection of the present invention.

Claims

A pyrazole amide compound having a structure represented by the following formula (1):
Use of the compound of claim 1 for controlling soybean rust.
Use of the compound of claim 1 for controlling corn rust.
Use of the compound of claim 1 for controlling wheat powdery mildew.
Use of the compound of claim 1 for controlling cucumber powdery mildew.
Use of the compound of claim 1 for the preparation of a pesticide for controlling at least two diseases of soybean rust, corn rust, wheat powdery mildew and cucumber powdery mildew.
A bactericide comprising an active ingredient and an adjuvant, the active ingredient comprising the pyrazole amide compound of claim 1.
The bactericide according to claim 7, wherein the active ingredient is contained in an amount of from 1 to 99.9% by weight.
The bactericide according to claim 7 or 8, wherein the bactericidal agent is in a form selected from the group consisting of at least one of an emulsifiable concentrate, a suspending agent, a wettable powder, a powder, a granule, a liquid, a bait, a mother liquor, and a mother powder.