Pyrazole amide compound and application thereof, and fungicide

Abstract

The present invention relates to the field of pesticides. Disclosed are a pyrazole amide compound and an application thereof, and a fungicide. The pyrazole amide compound has a structure as represented by Formula (1). The pyrazole amide compound provided by the present invention has significant control effects on soybean rust, corn rust, wheat powdery mildew, cucumber powdery mildew, and rice sheath blight even at low concentration.

Claims

1. A pyrazole amide compound having a structure represented by the following Formula (1): ##STR00008##

2. A method of preventing or treating at least one crop disease selected from the group consisting of soybean rust, wheat powdery mildew, cucumber powdery mildew, and rice sheath blight, the method comprising applying the compound of claim 1 to a plant in need thereof.

3. A fungicide comprising an active ingredient and auxiliary material, wherein the active ingredient comprises the pyrazole amide compound of claim 1.

4. The fungicide of claim 3, wherein the active ingredient is contained in an amount of 1 wt % to 99.9 wt %.

5. The fungicide of claim 3, wherein the dosage form of the fungicide is at least one selected from the group consisting of emulsifiable concentrate, suspension concentrate, water powder, dust powder, granule, aqueous solution, bait, mother liquor and mother powder.

6. The fungicide of claim 4, wherein the dosage form of the fungicide is at least one selected from the group consisting of emulsifiable concentrate, suspension concentrate, water powder, dust powder, granule, aqueous solution, bait, mother liquor and mother powder.

Description

DETAILED DESCRIPTION

(1) The terminals and any value of the ranges disclosed herein are not limited to the precise ranges or values, such ranges or values shall be comprehended as comprising the values adjacent to the ranges or values. As for numerical ranges, the endpoint values of the various ranges, the endpoint values and the individual point value of the various ranges, and the individual point values may be combined with one another to produce one or more new numerical ranges, which should be deemed have been specifically disclosed herein.

(2) The present disclosure does not impose specific restriction on the method for preparing the pyrazole amide compound represented by Formula (1), for example, the pyrazole amide compound represented by Formula (1) may be prepared by the following synthetic route:

(3) ##STR00005##

(4) When the pyrazole amide compound represented by Formula (1) is used for preventing and treating soybean rust, corn rust, wheat powdery mildew, cucumber powdery mildew or rice sheath blight, a pesticide composition may be prepared by using a substance containing the pyrazole amide compound with the structure shown in formula (1) as an active ingredient, and used in an effective amount for the prevention and treatment of crop diseases.

(5) The auxiliary materials in the fungicide of the present disclosure may be the adjuvants commonly used in the art for producing a variety of suitable dosage forms, including but not limited to surfactants and the other substances.

(6) The present disclosure will be described in detail as below with reference to examples. Unless otherwise specified, each of the reagents described in the following examples is commercially available.

(7) Each of the commercial controls in the following examples is the key pesticide currently sold on the market. For example, benzovindiflupyr is currently the commercial fungicide with highest activity against soybean rust and corn rust, prothioconazole and azoxystrobin are also staple products against soybean rust. Ethirimol, prothioconazole and fluxapyroxad are main products for preventing and treating powdery mildew on the market. Undoubtedly, the chemical structures of these commercial controls are significantly different from the compound of the present disclosure.

Example 1

(8) The pyrazole amide compound with the structure shown in Formula (1) was prepared by using the synthetic route described in the foregoing description of the present disclosure, the specific contents were as follows:

(9) (1) The synthesis of compound expressed by Formula 1-3

(10) Compound expressed by Formula 1-2 (3 mmol), compound expressed by Formula 1-1 (3.3 mmol) and potassium carbonate (3.6 mmol) were added into a 50 mL round bottomed flask, dimethyl formamide (DMF, 20 mL) was further added, the mixture was stirred and heated to 100° C., when thin-layer chromatography (TLC) show the raw materials were exhausted, the reaction was stopped, then ethyl acetate (50 mL) was added, the mixture was washed with brine (50 mL*2), the organic layer was dried over anhydrous Na.sub.2SO.sub.4 and concentrated under reduced pressure, the residue was purified by column chromatography on silica gel to give the compound expressed by Formula 1-3, the yield was 55%.

(11) Brown liquid, .sup.1H NMR (600 MHz, DMSO-d.sub.6) δ 8.02 (s, 1H), 7.96 (d, J=8.5 Hz, 1H), 7.04 (dd, J=11.0, 4.3 Hz, 1H), 6.90 (dd, J=10.1, 9.0 Hz, 3H), 6.65-6.58 (m, 1H), 4.99 (s, 2H). GC-MS: M/z 321.05[M].sup.+.

(12) (2) The synthesis of the compound expressed by Formula 1

(13) Compound expressed by Formula 1-3 (2 mmol) was dissolved into dichloromethane (20 mL), triethylamine (3 mmol) was added, then the mixture was added dropwise with the compound represented by Formula 1-4 (in total of 2.4 mmol) under an ice bath condition. TLC showed the reaction was completed, dichloromethane (30 mL) was added, the mixture was washed with brine (50 mL*3), the organic layer was dried over anhydrous Na.sub.2SO.sub.4 and concentrated under reduced pressure, the residue was purified by column chromatography on silica gel to give the compound expressed by Formula 1, the yield was 79%.

(14) White powder, .sup.1H NMR (600 MHz, DMSO-d.sub.6) δ 9.68 (s, 1H), 8.04 (s, 1H), 8.00 (d, J=8.9 Hz, 1H), 7.96 (d, J=8.0 Hz, 1H), 7.34 (t, J=7.7 Hz, 1H), 7.29 (t, J=7.7 Hz, 1H), 7.15 (d, J=7.8 Hz, 2H), 7.09 (t, J=54 Hz, 1H), 7.07 (d, J=5.9 Hz, 1H), 3.85 (s, 3H). HRMS (MALDI) Calcd for C.sub.20H.sub.13F.sub.8N.sub.3O.sub.2 [M+Na].sup.+: 502.07722, found: 502.08035.

Test Example 1: Screening Results of Fungicidal Activity in Greenhouse Pot Tests

(15) Test method: each of the test compounds in Table 1 was dispensed to 5 wt % emulsifiable concentrate (hereinafter referred to as 5% EC). The greenhouse pot test was used in each experiment, and the effective concentrations of each compound were illustrated in Table 1.

(16) Soybean rust: two-leaf stage potted soybean seedling with uniform growth was selected and made foliar spray treatment with 5% EC, the blank control sprayed with clean water was additionally arranged, three replicates were carried out. After 24 h, the leaves of the host plants were inoculated with sporangial suspensions of the fungi soybean rust (Phakopsora pacchyrhizi Sydow), the plants were stored in humidity chamber (temperature 20-25° C., relative humidity>95%) and then transferred to greenhouse (25±1° C.) 8-16 h after infection. After 7 days, the screening results were investigated according to the disease incidence condition of blank control.

(17) Corn rust: two-three leaf stage potted corn seedling with uniform growth was selected and made foliar spray treatment with 5% EC, the blank control sprayed with clean water was additionally arranged, three replicates were carried out. After 24 h, the leaves of the host plants were inoculated with sporangial suspensions of the fungi corn rust (Puccinia sorghi), the plants were stored in humidity chamber (temperature: lighting 25° C., dark 20° C., relative humidity 95-100%) and then transferred to greenhouse (25±1° C.) 24 h after infection. After 7 days, the screening results were investigated according to the disease incidence condition of blank control.

(18) Wheat powdery mildew: two-leaf stage potted wheat seedling with uniform growth was selected and made foliar spray treatment with 5% EC, the blank control sprayed with clean water was additionally arranged, three replicates were carried out. After 24 h, the leaves of the host plants were inoculated by shake-down method with sporangial suspensions of the fungi wheat powdery mildew (Erysiphe graminis), the plants were stored in a greenhouse (25±1° C.). After 7 days, the screening results were investigated according to the disease incidence condition of blank control.

(19) Cucumber powdery mildew: cucumber seedling in a true leaf period with uniform growth was selected, and dried in the shade for 24 h after spray treatment. Fresh cucumber powdery mildew spores on the cucumber leaves were collected and washed, and filtered through a double gauze to prepare a spores suspension with concentration of about 100,000/mL, then spray inoculation was applied. The test materials inoculated were moved into a greenhouse (lighting 21-23° C.), after 8 days, the grading investigation was carried out according to the disease incidence condition of blank control, and the control effect in a unit of % was calculated according to disease index.

(20) The investigation method: “Guidelines for the field efficacy trials of pesticides” was adopted as the grading standard, and the control effect in a unit of % was calculated based on the disease index.
Disease index=Σ(number of diseased leaves at each grade×relative grade value)×100/(total number of leaves×9);
Control effect (%)=(disease index of control−disease index of treated)×100/disease index of control;

(21) The test results were illustrated in Table 1.

(22) The structures of control compounds 2-8 in Table 1 are as follows:

(23) ##STR00006## ##STR00007##

(24) TABLE-US-00001 TABLE 1 Control effect (%) Wheat Cucumber Concentration Corn Soybean powdery powdery Number (mg/L) rust rust mildew mildew Compound 1 100 100 100 100 100 25 100 100 100 100 6.25 100 100 100 100 Compound 2 100 100 100 85 88 25 100 100 75 55 6.25 98 96 70 45 Compound 3 100 100 100 80 95 25 100 100 80 70 6.25 75 85 65 45 Compound 4 100 100 100 60 — 25 100 100 25 — 6.25 98 100 10 — Compound 5 100 85 100 50 — 25 75 98 40 — 6.25 70 95 10 — Compound 6 100 100 100 92 98 25 100 100 90 75 6.25 98 90 85 50 Compound 7 100 100 100 90 89 25 95 98 75 60 6.25 90 96 60 30 Compound 8 100 100 100 94 95 25 99 100 75 60 6.25 95 99 65 40 Benzovindiflupyr 100 — — — 100 25 — — — 100 6.25 — — — 80 Prothioconazole 100 — — — 100 25 — — — 98 6.25 — — — 85 Fluxapyroxad 100 — — — 100 25 — — — 100 6.25 — — — 95 Ethirimol 100 — — — 100 Difenoconazole 100 — — — 80 Azoxystrobin 400 — — — 30 100 — — — 0

(25) As shown in Table 1, the compound provided by the present disclosure exhibited desirable control effects on corn rust, soybean rust, wheat powdery mildew, cucumber powdery mildew and rice sheath blight at low concentration. Particularly, the control effect of the compound provided by the present disclosure on wheat powdery mildew and cucumber powdery mildew at low concentration better than those of the compounds provided by the prior art.

(26) Compared the structures of compound 2, compound 3 and compound provided by the present disclosure, we found that the ortho-position substituent on the free phenyl group of the diphenyl ether of the compound 2 and compound 3 is a halogen (the corresponding position of the compound provided by the present disclosure is trifluoromethyl group), and the 5-position at the pyrazole ring of the compound 2 and compound 3 contains a fluorine substituent. According to the results from Table 1, at concentration of 25 mg/L, the control effects of the compound 2 and compound 3 on corn rust and soybean rust are equivalent to those of the compound of the present disclosure, but at concentration of 6.25 mg/L, the compound 2 and compound 3 have the defect that their control effects are poorer than those of the compounds of the present disclosure. Furthermore, the control effects of the compound 2 and compound 3 on wheat powdery mildew and cucumber powdery mildew are obviously poorer than those of the compound of the present disclosure at the same concentration. Therefore, the number of trifluoromethyl substituent on free phenyl of diphenyl ether and the fluorine substituent at 5-position on pyrazole ring have important influence on the control effects and application range of the pyrazole amide compounds.

(27) Compared the structural formula of the compound 4 with the compound provided by the present disclosure, the structural difference is that the ortho-position substituent on the free phenyl group of the diphenyl ether of the compound 4 is a halogen (the corresponding position of the compound provided by the present disclosure is trifluoromethyl). According to the results in Table 1, the control effects of compound 4 on corn rust and soybean rust are equivalent to those of the compound of the present disclosure at concentration of 25 mg/L or above, but the control effect of compound 4 on corn rust is poorer than that of the compound of the present disclosure at concentration of 6.25 mg/L. Furthermore, the control effect of the compound 4 at the same concentration on the wheat powdery mildew is obviously poorer than that of the compound of the present disclosure. Therefore, the number of the trifluoromethyl substituent on the free phenyl of the diphenyl ether has important influence on the control effects and the application range of the pyrazole amide compound.

(28) Compared the structural formula of the compound 5 and the compound provided by the present disclosure, the difference is that the substituent at the 2, 5-position substituent on the free phenyl group of the diphenyl ether of the compound 5 is trifluoromethyl (the substitution position of the trifluoromethyl group of the compound provided by the present disclosure is the 2, 4-position pattern). According to the results in Table 1, the control effect of compound 5 on soybean rust is equivalent to that of the compound of the present disclosure at concentration of 100 mg/L or above, but the control effect of compound 5 on soybean rust is significantly poorer that of the compound of the present disclosure at concentration of 100 mg/L or below. Furthermore, the control effect of the compound 5 at the same concentration on wheat powdery mildew and soybean rust is obviously poorer than that of the compound of the present disclosure. Therefore, the position of the trifluoromethyl substituent on the free phenyl of the diphenyl ether and the fluorine substituent at the 5-position on the pyrazole ring have important influence on the control effects and the application range of the pyrazole amide compounds.

(29) Compared the structural formula of the compound 6 and the compound provided by the present disclosure, the difference is that the 5-position of the pyrazole ring of the compound 6 contains a fluorine substituent (whereas the compound of the present disclosure does not have the substituent at the corresponding position). According to the results in Table 1, the control effect of compound 6 on corn rust and soybean rust is equivalent to those of the compound of the present disclosure at concentration of 25 mg/L or more, but the control effect of compound 6 on corn rust and soybean rust are inferior to that of the compound of the present disclosure at a concentration of 6.25 mg/L. Furthermore, the control effect of the compound 6 at the same concentration on wheat powdery mildew and cucumber powdery mildew are significantly lower than those of the compound of the present disclosure. Therefore, the fluorine atom at the 5-position of the pyrazole ring has important influence on the control effect and the application range of the pyrazole amide compound.

(30) Compared the structural formula of the compound 7 and the compound provided by the present disclosure, the difference is that the substituents at the 2, 4-position on the free phenyl group of the diphenyl ether of the compound 7 are both chlorines (the substituents at the 2, 4-positions of the compound provided by the present disclosure are both trifluoromethyl groups). According to the results in Table 1, the control effect of compound 7 on corn rust and soybean rust are equivalent to those of the compound of the present disclosure at concentration of 100 mg/L or above, but the control effect of compound 7 on soybean rust is poorer that of the compound of the present disclosure below the concentration of 100 mg/L. Furthermore, the control effect of the compound 7 at the same concentration on wheat powdery mildew and cucumber powdery mildew is obviously poorer than that of the compound of the present disclosure. Therefore, the substituent pattern at the 2, 4-position of the free phenyl of the diphenyl ether has important influence on the control effect and the application range of the pyrazole amide compounds.

(31) Compared the structural formula of the compound 8 and the compound provided by the present disclosure, the difference is that the substituent at 2-position on the free phenyl group of the diphenyl ether of the compound 8 is chlorine (the substituent at 2-position of the compound provided by the present disclosure is trifluoromethyl). According to the results in Table 1, the control effects of compound 8 on corn rust and soybean rust are equivalent to those of the compound of the present disclosure at the same concentration. However, the control effects of the compound 8 at the same concentration on wheat powdery mildew and cucumber powdery mildew are significantly lower than those of the compound of the present disclosure. Therefore, the substituent pattern at 2-position on the free phenyl of the diphenyl ether has important influence on the control effects and the application range of the pyrazole amide compounds.

(32) Particularly, the control effect of the compound in the present disclosure on cucumber powdery mildew at low concentration (6.25 mg/L) is remarkably better that of control compounds and the existing commercial pesticide.

Test Example 2: Fungicidal Activity Screening at Low Concentration

(33) The compounds provided by the present disclosure and some control compounds were tested by the same methods in the Test example 1, except that the effective concentrations of the compounds in this Test example are shown in Table 2.

(34) In addition, the test method for rice sheath blight as following steps:

(35) The potted rice seedling with uniform growth was selected, and dried in the shade for 24 h after spray treatment, then inoculated 3 blocks of 0.25 cm.sup.2 rice sheath blight fungi (Rhizoctonia solami) at the base of seedling by clamp inoculation bacterium block method. The test materials inoculated were moved into greenhouse (temperature: lighting 28° C., dark 25° C., relative humidity 95%), after 7 days, investigate 5 leaves of per block treatment, the grading investigation was carried out according to the disease incidence condition of sheaths and leaves of rice, “Guidelines for the field efficacy trials of pesticides” was adopted as the grading standard, the disease index was calculated according to the grading standard, and the control effect in a unit of % was calculated according to disease index.

(36) The test results of this test example are illustrated in Table 2.

(37) TABLE-US-00002 TABLE 2 Control effect (%) Wheat Cucumber Rice Concentration Corn Soybean powdery powdery sheath Number (mg/L) rust rust mildew mildew blight Compound 1 10 100 100 100  100  100  3.1250 100 100 100  100  100  2.5 100 100 100  98 90 1.5625 100 100 85 95 85 1 — 100 — 90 80 0.625 — — — — 75 0.5 — 100 — — — Compound 4 3.1250 90 100 70 — — 1.5625 50 98 30 — — Compound 7 3.1250 60 100 50 — — 1.5625 50 90  0 — — Compound 8 3.1250 98 100 90 — — 1.5625 85 98 70 — — Benzovindiflupyr 3.1250 98 100 70 — 65 1.5625 95 100 50 20 55 1 — 98 — — 40 0.5 — 95 — — 30 Prothioconazole 4 — 100 70 90 — 2 — 100 50 80 — 1 — 100 30 75 — 0.5 — 95 — — — Fluxapyroxad 1.5625 — — — 55 — Epoxiconazole 10 — — — — 100  2.5 — — — — 70 0.625 — — — — 30

(38) According to the results in Table 2, at concentration of 3.125 mg/L, the control effects of compound 4, compound 7 and compound 8 on corn rust and soybean rust are equivalent to those of the compound of the present disclosure, but compound 4, compound 7 and compound 8 have poorer control effects on corn rust and soybean rust than those of the compound of the present disclosure below the concentration of 3.125 mg/L. Furthermore, the control effects of the compound 4, the compound 7 and the compound 8 on wheat powdery mildew is significantly poorer than that of the compound of the present disclosure at the same concentration.

(39) Moreover, according to the results in Table 2, the control effects of the compound of the present disclosure at low concentration on cucumber powdery mildew and rice sheath blight are superior to or equivalent to those of the control compounds and the existing commercial pesticide.

Test Example 3: Field Trails

(40) I. Cucumber Powdery Mildew Test Method:

(41) Spray method: Stein and leaf spray (Applicator: Xinkangda lithium battery electric sprayer).

(42) Test crop: cucumber (cultivars: Tianjiao7)

(43) The test was carried out in Shenyang, the test field was loam with rich organic matters and normal management of fertilizer and water, and no other pesticide was applied during the test.

(44) The arrangement of the test plot was random block permutation; the area of the test plot: 15 m.sup.2; repeat times: 3 times; spray time and frequency: period between Sep. 28, 2018 and Oct. 11, 2018, twice. Spray dosage: each treatment was repeated 3 times, the total water consumption was 8 L. No other pesticide was applied during the test. The spray in the test was carried out in sunny days, and it did not rain next day. 15-20 days after the second treatment, the incidence of disease spots in each plot was investigated.

(45) The incidence of disease spots in each plot was investigated by randomly selecting 4 samples/plot and 2 plants/samples, all leaves/plant, the incidence of the whole plant was recorded by counting the number of disease leaves and determining the incidence grade.

(46) Grading standard (in units of leaves):

(47) Grade 0: no leaf-spot area;

(48) Grade 1: the ratio of leaf-spot area to leaf area is less than 5%;

(49) Grade 3: the ratio of leaf-spot area to leaf area is between 6-10%;

(50) Grade 5: the ratio of leaf-spot area to leaf area is between 11-20%;

(51) Grade 7: the ratio of leaf-spot area to leaf area is between 21-40%;

(52) Grade 9: the ratio of leaf-spot area to leaf area is more than 40%;

(53) According to the relevant content of the “Guidelines for the field efficacy trials of pesticides of the People's Republic of China (PRC)”, the disease index was calculated according to the grading standard, and the control effect in a unit of % was calculated based on the disease index, and the test data of significance analysis was performed by using DPS evaluation system (DMRT).

(54) The results are shown in Table 3.

(55) TABLE-US-00003 TABLE 3 Concentration Control effect (%) Number (mg/L) Cucumber powdery mildew Compound 1 200 96.5 100 90.0 Pydiflumetofen 100 86.0 25% Ethirimol 200 90.0 suspension concentrate

(56) According to the results in Table 3, in terms of the control effect of field trials, the control effect on cucumber powdery mildew of the compound of the present disclosure is desirable and obviously better than mainstream pesticide pydiflumetofen and ethirimol suspension concentrate.

(57) II. The Wheat Powdery Mildew Test Method:

(58) Spray method: Stein and leaf spraying (Applicator: Xinkangda lithium battery electric sprayer).

(59) Test crops: wheat (cultivars: Liaochun 10)

(60) The test was carried out in Shenyang, the test field was loam with rich organic matters and normal management of fertilizer and water, and no other pesticide was applied during the test.

(61) The arrangement of the test plot was random block permutation; the area of the test plot: 15 m.sup.2; repeat times: 3 times; spray time and frequency: Sep. 17, 2018, once. Spray dosage: each treatment was repeated 3 times, the total water consumption was 8 L. No other pesticide was applied during the test. The spray in the test was carried out in sunny days, and it did not rain next day.

(62) The incidence of disease spots in each plot was investigated by diagonal selecting 4 samples/plot and 20 plants/samples, and the first leaf below the flag leaf of each plant was investigated.

(63) The grading standard of crop disease was as follows:

(64) Grade 0: no leaf-spot area;

(65) Grade 1: the ratio of leaf-spot area to leaf area is less than 5%;

(66) Grade 3: the ratio of leaf-spot area to leaf area is between 6-25%;

(67) Grade 5: the ratio of leaf-spot area to leaf area is between 26-50%;

(68) Grade 7: the ratio of leaf-spot area to leaf area is between 51-75%;

(69) Grade 9: the ratio of leaf-spot area to leaf area is between 76-100%;

(70) According to the relevant content of the “Guidelines for the field efficacy trials of pesticides of the People's Republic of China (PRC)”, the disease index was calculated according to the grading standard, and the control effect in a unit of % was calculated based on the disease index, and the test data of significance analysis was performed by using DPS evaluation system (DMRT).

(71) The results are shown in Table 4.

(72) TABLE-US-00004 TABLE 4 Concentration Control effect (%) Number (mg/L) Wheat powdery mildew Compound 1 200 100 100 98 Benzovindiflupyr 100 95 Pydiflumetofen 100 91.0 Prothioconazole 100 93

(73) The results are shown in Table 4, in terms of the control effect of field experiments, the control effect on wheat powdery mildew of the compound of the present disclosure is desirable and better than benzovindiflupyr, pydiflumetofen and prothioconazole.

(74) III. The Soybean Rust Test Method:

(75) Spray method: Stein and leaf spraying (Applicator: Xinkangda lithium battery electric sprayer).

(76) Test crops: soybean (cultivars: Glycine max(L) Merr)

(77) The test was carried out in Shenyang, the test field was loam with rich organic matters and normal management of fertilizer and water, and no other pesticide was applied during the test.

(78) The arrangement of the test plot was random block permutation; the area of the test plot: 25 m.sup.2; repeat times: 3 times; spray time and frequency: 2 times on Aug. 11, 2018 and Aug. 21, 2018 respectively. Spray dosage: each treatment was repeated 3 times, the total water consumption was 8 L. No other pesticide was applied during the test. The spray in the test was carried out in sunny days, and it did not rain next day. 15-20 days after the second spray treatment, the control effect was investigated.

(79) The incidence of disease spots in each plot was investigated by diagonal selecting 5 samples/plot and 20 plants/samples, 10 leaves/plant was surveyed.

(80) The grading standard of crop disease was as follows:

(81) Grade 0: no leaf-spot area;

(82) Grade 1: the ratio of leaf-spot area to leaf area is less than 5%;

(83) Grade 3: the ratio of leaf-spot area to leaf area is between 6-25%;

(84) Grade 5: the ratio of leaf-spot area to leaf area is between 26-50%;

(85) Grade 7: the ratio of leaf-spot area to leaf area is between 51-75%;

(86) Grade 9: the ratio of leaf-spot area to leaf area is between 76-100%;

(87) According to the relevant content of the “Guidelines for the field efficacy trials of pesticides of the People's Republic of China (PRC)”, the disease index was calculated according to the grading standard, and the control effect in a unit of % was calculated based on the disease index, and the test data of significance analysis was performed by using DPS evaluation system (DMRT).

(88) The results are shown in Table 5.

(89) TABLE-US-00005 TABLE 5 Dosage Control effect Number (mg/L) (%) Compound 1 50 92.67 75 94.56 100 97.69 Compound 4 50 80.14 75 85.62 100 93.11 Benzovindiflupyr 50 91.46 75 94.51 100 97.15 Prothioconazole 50 91.15 FOX 75 90.24 Azoxystrobin 50 84.62 CK 0.00

(90) The result indicates that the compounds of the present disclosure have desirable control effect on soybean rust, its control effect is equivalent to benzovindiflupyr, and is obviously better than prothioconazole, FOX and azoxystrobin.

(91) The above content describes in detail the preferred embodiments of the present disclosure, but the present disclosure is not limited thereto. A variety of simple modifications can be made in regard to the technical solutions of the present disclosure within the scope of the technical concept of the present disclosure, including a combination of individual technical features in any other suitable manner, such simple modifications and combinations thereof shall also be regarded as the content disclosed by the present disclosure, each of them falls into the protection scope of the present disclosure.