Fungicidal composition and method for controlling plant diseases

Abstract

To provide a fungicidal composition having stable and high fungicidal effects against cultivated crops infected with plant diseases resulting from plant diseases. A fungicidal composition containing, as active ingredients, (a) a benzoylpyridine derivative represented by the formula (I) or its salt: ##STR00001##
wherein when A is N, B is CX.sup.4; when A is CH, B is N; each of X.sup.1 and X.sup.2 which are independent of each other, is a halogen atom, an alkoxy group, a hydroxyl group, an alkyl group, a CF.sub.3 group or an alkylthio group; X.sup.3 is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF.sub.3 group or an alkylthio group; X.sup.4 is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF.sub.3 group or an alkylthio group; R.sup.1 is an alkyl group; R.sup.2 is an alkoxy group; p is 0, 1 or 2; and each of R.sup.2 and R.sup.2 is an alkoxy group, and (b) at least one additional fungicide.

Claims

1. A fungicidal composition comprising, as active ingredients: (a) a benzoylpyridine derivative represented by the formula (I) or a salt thereof: ##STR00007## wherein A is N or CH; when A is N, B is CX.sup.4; when A is CH, B is N; each of X.sup.1 and X.sup.2, which are independent of each other, is a halogen atom, an alkoxy group, a hydroxyl group, an alkyl group, a CF.sub.3 group or an alkylthio group; X.sup.3 is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF.sub.3 group or an alkylthio group; X.sup.4 is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF.sub.3 group or an alkylthio group; R.sup.1 is an alkyl group; R.sup.2 is an alkoxy group; p is 0, 1 or 2; and each of R.sup.2 and R.sup.2 is an alkoxy group, and (b) at least one fungicide selected from the group consisting of boscalid, penthiopyrad, meptyldinocap, sulfur, flutianil, 6-t-butyl-8-fluoro-2,3-dimethylquinolin-4-yl acetate and a compound represented by the formula (II): ##STR00008##

2. The fungicidal composition according to claim 1, wherein the fungicide (b) is at least one member selected from the group consisting of boscalid, penthiopyrad, meptyldinocap, sulfur and a compound represented by the formula (II): ##STR00009##

3. The fungicidal composition according to claim 1, wherein the fungicide (b) is at least one member selected from the group consisting of boscalid, penthiopyrad, meptyldinocap, sulfur and a compound represented by the formula (II): ##STR00010##

4. The fungicidal composition according to claim 1, wherein the benzoylpyridine derivative is a compound represented by the formula (I-1): ##STR00011## wherein each of X.sup.1 and X.sup.2, which are independent of each other, is a halogen atom, an alkoxy group, a hydroxyl group, an alkyl group, a CF.sub.3 group or an alkylthio group; X.sup.3 is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF.sub.3 group or an alkylthio group; R.sup.1 is an alkyl group; R.sup.2 is an alkoxy group; p is 0, 1 or 2; and each of R.sup.2 and R.sup.2 is an alkoxy group.

5. The fungicidal composition according to claim 4, wherein the benzoylpyricline derivative is at least one member selected from the group consisting of 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4-bromo-5-chloro-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-4-ethyl-2-methoxypyridine, 3-(4,5-dimethoxy-2-methylbenzoyl)-4,5-dichloro-2-methoxypyridine, 3-(5-ethoxy-4-methoxy-2-methylbenzoyl)-4,5-dichloro-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4-bromo-5-chloro-2-ethoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-2-ethoxy-4-methylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-bromo-4-chloro-2-ethoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4-chloro-5-iodo-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-iodo-2,4-dimethoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-2-methoxy-4-methylthiopyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-2,4-dimethoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4,5-dibromo-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4-bromo-2-methoxy-5-methylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-bromo-4-trifluoromethyl-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4,5-dichloro-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2,4-dichloro-5-methylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2,4-dichloro-5-iodopyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2-fluoro-4-iodo-5-methylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2-fluoro-4,5-dimethylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2-methoxy-4,5-dimethylpyridine, 3-(2-ethoxy-3,4-dimethoxy-6-methylbenzoyl)-2-ethoxy-4,5-dimethylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4,5-dimethyl-2-methylthiopyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-bromo-4-chloro-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4-chloromethoxy-5-methylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2-chloro-5-trifluoromethyl-4-methylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-trifluoromethyl-2-methoxy-4-methylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2,4-dichloro-5-trifluoromethylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4-chloro-5-trifluoromethyl-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-4-ethinyl-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-4-fluoromethyl-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-bromo-4-fluoromethyl-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4-fluoromethyl-2-methoxy-5-methylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-4-difluoromethyl-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-ethyl-4-trifluoromethyl-2-methoxypyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-2-methoxy-4-methylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-bromo-2-methoxy-4-methylpyridine, 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4-trifluoromethyl-2-methoxy-5-methylpyridine and 3-(4,5-dimethoxy-2-methylbenzoyl)-5-chloro-2-methoxy-4-methylpyridine.

6. The fungicidal composition according to claim 1, wherein the benzoylpyridine derivative is a compound represented by the formula (I-2): ##STR00012## wherein each of X.sup.1 and X.sup.2, which are independent of each other, is a halogen atom, an alkoxy group, a hydroxyl group, an alkyl group, a CF.sub.3 group or an alkylthio group; X.sup.3 is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF.sub.3 group or an alkylthio group; X.sup.4 is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF.sub.3 group or an alkylthio group; R.sup.1 is an alkyl group; R.sup.2 is an alkoxy group; p is 0, 1 or 2; and each of R.sup.2 and R.sup.2 is an alkoxy group.

7. The fungicidal composition according to claim 6, wherein the benzoylpyridine derivative is at least one compound selected from the group consisting of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2,5-dichloro-3-trifluoromethylpyridine, 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2-chloro-3-trifluoromethyl-5-methoxypyridine, 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2-bromo-3-trifluoromethyl-5-methoxypyridine, 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2,3,5-trichloropyridine, 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3,5-dichloropyridine, 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3-chloro-5-methoxypyridine, 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2-bromo-3-chloro-5-methoxypyridine and 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3-bromo-5-methylpyridine).

8. The fungicidal composition according to claim 1, wherein the benzoylpyridine derivative is at least one compound selected from the group consisting of 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-2-methoxy-4-methylpyridine, 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2,5-dichloro-3-trifluoromethylpyridine and 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2-chloro-3-trifluoromethyl-5-methoxypyridine.

9. The fungicidal composition according to claim 8, wherein the benzoylpyridine derivative is 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-2-methoxy-4-methylpyridine.

10. The fungicidal composition according to claim 8, wherein the benzoylpyridine derivative is at least one compound selected from the group consisting of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2,5-dichloro-3-trifluoromethylpyridine and 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2-chloro-3-trifluoromethyl-5-methoxypyridine.

11. The fungicidal composition according to claim 1, wherein the mixing weight ratio of the benzoylpyridine derivative or a salt thereof (a) to the fungicide (b) is from 1:200 to 200:1.

12. The fungicidal composition according to claim 1, wherein (b) is boscalid.

13. The fungicidal composition according to claim 1, wherein (b) is penthiopyrad.

14. The fungicidal composition according to claim 1, wherein (b) is meptyldinocap.

15. The fungicidal composition according to claim 1, wherein (b) is sulfur.

16. The fungicidal composition according to claim 1, wherein (b) is 6-t-butyl-8-fluoro-2,3-dimethylquinolin-4-yl acetate.

17. The fungicidal composition according to claim 1, wherein (b) is a compound represented by the formula (II).

18. A method for controlling plant diseases, which comprises applying the fungicidal composition as defined in claim 1 to plants.

Description

EXAMPLES

(1) Now, the present invention will be described in further detail with reference to Examples. However, it should be understood that the present invention is by no means restricted thereto.

Test Example 1: Test on Preventive Effect Against Wheat Powdery Mildew

(2) Wheat (cultivar: Norin-61-go) was cultivated in a plastic pot having a diameter of 7.5 cm, and when it reached 1.5-leaf stage, 10 ml of a chemical solution having each test compound adjusted to a prescribed concentration, was applied by a spray gun in an amount of 1000 L/ha. After the chemical solution dried, conidia of Erysiphe graminis were dusted and inoculated and maintained in a constant temperature chamber at 20 C. From 6 to 8 days after the inoculation, the area of sporulation was investigated, and the disease rate was determined in accordance with the following formula, and the results are shown in Tables 1 to 4. The average lesion area in the non-treated plot was determined in the same manner as for the treated plot except that water was applied by a spray gun instead of the chemical solution.
Disease rate=(a/b)100

(3) a: average lesion area in the treated plot

(4) b: average lesion area in the non-treated plot

(5) Theoretical values were calculated in accordance with the Colby's formula. The fungicidal composition of the present invention has a synergistic effect regarding the test on preventive effect against wheat powdery mildew, when the experimental value is lower than the theoretical value. Theoretical values by the Colby's formula in such cases are shown in brackets in Tables 1 to 4.

(6) TABLE-US-00001 TABLE 1 Concentration of Concentration of compound No. 35 Pyraclostrobin 1.6 ppm 0.8 ppm 0 ppm 400 ppm 7.5 (70) 30 (70) 100 200 ppm 10 (70) 50 (70) 100 100 ppm 30 (70) 50 (70) 100 0 ppm 70 70 100

(7) TABLE-US-00002 TABLE 2 Concentration of Concentration of compound No. 39 Pyraclostrobin 6.3 ppm 3.1 ppm 1.6 ppm 0 ppm 400 ppm 5 (60) 10 (75) 60 (85) 100 200 ppm 7.5 (60) 50 (75) 70 (85) 100 100 ppm 50 (60) 60 (75) 70 (85) 100 0 ppm 60 75 85 100

(8) TABLE-US-00003 TABLE 3 Concentration of Concentration of compound No. 40 Pyraclostrobin 0.8 ppm 0 ppm 400 ppm 10 (50) 100 200 ppm 30 (50) 100 0 ppm 50 100

(9) TABLE-US-00004 TABLE 4 Concentration of Concentration of compound No. 35 Difenoconazole 6.3 ppm 3.1 ppm 1.6 ppm 0.8 ppm 0 ppm 50 ppm 5 (24) 10 (40) 30 (40) 30 (40) 40 25 ppm 5 (42) 8 (70) 50 (70) 50 (70) 70 12.5 ppm 8 (51) 50 (85) 50 (85) 60 (85) 85 0 ppm 60 100 100 100 98

Test Example 2: Test on Preventive Effect Against Cucumber Powdery Mildew

(10) Cucumber (cultivar: Suyo) was cultivated in a plastic pot having a diameter of 7.5 cm, and when it reached 1.5-leaf stage, 10 ml of a chemical solution having the compound of the present invention adjusted to a prescribed concentration, was applied by a spray gun. After the chemical solution dried, a suspension of conidia of Sphaerotheca cucurbitae was sprayed and inoculated and maintained in a constant temperature chamber at 20 C. From 9 to 10 days after the inoculation, the area of sporulation was investigated, and the disease rate was determined in the same manner as in Test Example 1, and the results are shown in Tables 5 to 20. The average lesion area in the non-treated plot was determined in the same manner as for the treated plot except that water was applied by a spray gun instead of the chemical solution.

(11) Further, theoretical values by the Colby's formula are shown in brackets in Tables 5 to 20.

(12) TABLE-US-00005 TABLE 5 Concentration of Concentration of compound No. 35 Pyribencarb 6.3 ppm 0.8 ppm 0 ppm 50 ppm 5.4 (12.3) 43.8 (58.4) 63.2 25 ppm 4.9 (12.3) 48.7 (58.4) 63.2 12.5 ppm 2.9 (14.2) 43.8 (67.5) 73.0 0 ppm 19.5 92.4 97.3

(13) TABLE-US-00006 TABLE 6 Concentration of Concentration of compound No. 39 Pyribencarb 12.5 ppm 6.3 ppm 0 ppm 50 ppm 14.6 (36.9) 24.3 (55.4) 63.2 25 ppm 19.5 (36.9) 34.1 (55.4) 63.2 12.5 ppm 24.3 (42.6) 29.2 (63.9) 73.0 0 ppm 58.4 87.6 97.3

(14) TABLE-US-00007 TABLE 7 Concentration of Concentration of compound No. 40 Pyribencarb 3.1 ppm 0 ppm 25 ppm 14.6 (24.6) 63.2 12.5 ppm 19.5 (28.4) 73.0 0 ppm 38.9 97.3

(15) TABLE-US-00008 TABLE 8 Concentration of Concentration of compound No. 35 Boscalid 3.1 ppm 1.6 ppm 0 ppm 25 ppm 0.4 (2.2) 6.5 (12.2) 25.8 12.5 ppm 0.9 (3.7) 8.6 (20.3) 43.0 0 ppm 8.6 47.3 86.0

(16) TABLE-US-00009 TABLE 9 Concentration of Concentration of compound No. 39 Boscalid 12.5 ppm 6.3 ppm 0 ppm 25 ppm 4.3 (11.1) 0 (13.3) 25.8 12.5 ppm 8.6 (18.5) 21.5 (22.2) 43.0 0 ppm 43.0 51.6 86.0

(17) TABLE-US-00010 TABLE 10 Concentration of Concentration of compound No. 40 Boscalid 3.1 ppm 1.6 ppm 0 ppm 25 ppm 0.4 (2.2) 4.3 (11.1) 25.8 12.5 ppm 0 (3.7) 12.9 (18.5) 43.0 6.3 ppm 2.6 (3.7) 12.9 (18.5) 43.0 0 ppm 8.6 43.0 86.0

(18) TABLE-US-00011 TABLE 11 Concentration of Concentration of compound No. 35 Penthiopyrad 3.1 ppm 1.6 ppm 0 ppm 0.8 ppm 0.4 (4.4) 17.2 (24.4) 51.6 0.4 ppm 0.9 (6.7) 30.1 (36.6) 77.4 0 ppm 8.6 47.3 86.0

(19) TABLE-US-00012 TABLE 12 Concentration of compound Concentration of No. 39 Penthiopyrad 6.3 ppm 0 ppm 1.6 ppm 4.3 (8.9) 17.2 0.8 ppm 8.6 (26.6) 51.6 0.4 ppm 34.4 (39.9) 77.4 0 ppm 51.6 86.0

(20) TABLE-US-00013 TABLE 13 Concentration of compound Concentration of No. 35 Meptyldinocap 0.4 ppm 0 ppm 1.6 ppm 25 (36) 60 0.8 ppm 30 (45) 75 0 ppm 60 100

(21) TABLE-US-00014 TABLE 14 Concentration of compound Concentration of No. 39 Meptyldinocap 6.3 ppm 0 ppm 3.1 ppm 20 (27) 60 1.6 ppm 15 (27) 60 0 ppm 45 100

(22) TABLE-US-00015 TABLE 15 Concentration of Concentration of compound the compound of No. 35 the formula (II) 3.1 ppm 0 ppm 1.6 ppm 5.4 (17.3) 58.7 0.8 ppm 0.5 (25.9) 88.1 0 ppm 29.4 97.9

(23) TABLE-US-00016 TABLE 16 Concentration of Concentration of compound the compound of No. 39 the formula (II) 12.5 ppm 0 ppm 6.3 ppm 2.2 (3.7) 8.6 3.1 ppm 4.7 (7.4) 17.2 1.6 ppm 21.5 (25.9) 60.2 0 ppm 43 86

(24) TABLE-US-00017 TABLE 17 Concentration of Concentration of compound the compound of No. 40 the formula (II) 3.1 ppm 0 ppm 6.3 ppm 0 (0.74) 8.6 3.1 ppm 0 (1.5) 17.2 1.6 ppm 4.3 (5.2) 60.2 0 ppm 8.6 86

(25) TABLE-US-00018 TABLE 18 Concentration of Concentration of compound No. 35 sulfur 3.1 ppm 1.6 ppm 0.8 ppm 0 ppm 25 ppm 39.2 (60.5) 44.1 (67.2) 44.1 (67.2) 68.6 12.5 ppm 29.4 (77.8) 49.0 (86.4) 58.8 (86.4) 88.2 6.3 ppm 29.4 (86.4) 53.9 (96.0) 88.2 (96.0) 98.0 0 ppm 88.2 98.0 98.0 98.0

(26) TABLE-US-00019 TABLE 19 Concentration of Concentration of compound No. 35 flutianil 6.3 ppm 3.1 ppm 0 ppm 0.025 ppm 0 (4.9) 12.5 (52.0) 65 0.0125 ppm 3 (6.4) 40 (68.0) 85 0.0063 ppm 3 (7.1) 60 (76.0) 95 0 ppm 7.5 80 98.3

(27) TABLE-US-00020 TABLE 20 Concentration of 6- t-butyl-8-fluoro-2,3- dimethylquinolin-4- Concentration of compound No. 35 yl acetate 3.1 ppm 1.6 ppm 0.8 ppm 0.4 ppm 0 ppm 50 ppm 7.4 (20.3) 14.7 (33.8) 29.5 (33.8) 14.7 (33.8) 34.4 25 ppm 7.4 (34.8) 34.4 (58.0) 19.7 (58.0) 24.6 (58.0) 59.0 12.5 ppm 7.4 (37.7) 29.5 (62.8) 39.3 (62.8) 44.2 (62.8) 63.9 6.3 ppm 29.5 (49.3) 49.2 (82.1) 68.8 (82.1) 68.8 (82.1) 83.6 0 ppm 59.0 98.3 98.3 98.3 98.3

(28) Now, Formulation Examples of the present invention will be described below. However, the blend ratio, type of formulation or the like of the present invention is by no means restricted to the following Examples.

Formulation Example 1

(29) TABLE-US-00021 (a) Kaolin 78 parts by weight (b) Condensate of -naphthalenesulfonic acid 2 parts by weight sodium salt with formalin (c) Polyoxyethylene alkylaryl sulfate 5 parts by weight (d) Hydrated amorphous silicon dioxide 15 parts by weight

(30) A mixture of the above components, the compound of the formula (I) and Pyraclostrobin are mixed in a weight ratio of 8:1:1 to obtain a wettable powder.

Formulation Example 2

(31) TABLE-US-00022 (a) Compound of the formula (I) 0.5 part by weight.sup. (b) Pyraclostrobin 0.5 part by weight.sup. (c) Bentonite 20 parts by weight (d) Kaolin 74 parts by weight (e) Sodium lignin sulfonate 5 parts by weight

(32) An appropriate amount of water for granulation is added to the above components and mixed, and the mixture is granulated to obtain granules.

Formulation Example 3

(33) TABLE-US-00023 (a) Compound of the formula (I) 2 parts by weight (b) Pyraclostrobin 3 parts by weight (c) Talc 95 parts by weight
The above components are uniformly mixed to obtain a dust.