FUNGICIDAL COMPOSITION COMPRISING A PYRIDYLETHYLBENZAMIDE DERIVATIVE AND A COMPOUND CAPABLE OF INHIBITING THE ERGOSTEROL BIOSYNTHESIS

Abstract

A composition comprising at least a pyridylethylbenzamide derivative of general formula (I) (a) and a triazole derivative (b) and a further compound (c) selected from the group consisting of spiroxamine, prothioconazole, and tebuconazole, wherein compound (c) is different from compound (b). A method for preventively or curatively combating the phytopathogenic fungi of crops by using this composition.

Claims

1. A composition comprising a) a pyridylethylbenzamide derivative of formula (I) ##STR00002## or 2-pyridine N-oxides thereof, in which p is an integer equal to 1, 2, 3 or 4; q is an integer equal to 1, 2, 3, 4 or 5; each substituent X, independently of the others, is halogen, alkyl or haloalkyl; each substituent Y, independently of the others, is halogen, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, amino, phenoxy, alkylthio, dialkylamino, acyl, cyano, ester, hydroxy, aminoalkyl, benzyl, haloalkoxy, halosulphonyl, halothioalkyl, alkoxyalkenyl, alkylsulphonamide, nitro, alkylsulphonyl, phenylsulphonyl or benzylsulphonyl; and b) a triazole derivative capable of inhibiting ergosterol biosynthesis in a (a)/(b) weight ratio of from 0.01 to 20, wherein the triazole derivative is azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, diclobutrazole, etaconazole, fluotrimazole, furconazole, furconazole-cis, triamiphos or triazbutil, and c) a further fungicidal compound (c) different from a) and b) selected from the group consisting of spiroxamine, prothioconazole, and tebuconazole.

2. The composition according to claim 1, wherein p is 2.

3. The composition according to claim 1, wherein q is 2.

4. The composition according to claim 1, wherein X, independently of the others, is halogen or haloalkyl.

5. The composition according to claim 1, wherein X, independently of the others, is a chloro atom or a trifluoromethyl group. 10

6. The composition according to claim 1, wherein Y, independently of the others, is halogen or haloalkyl.

7. The composition according to claim 1, wherein Y, independently of the others, is a chloro atom or a trifluoromethyl group.

8. The composition according to claim 1, wherein the compound of formula (I) is N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide; N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-iodobenzamide; or N-{2-[3,5-dichloro-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide.

9. The composition according to claim 8, wherein the compound of formula (I) is N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide.

9. The composition according to claim 1, wherein the fungicidal compound (c) is tebuconazole.

10. The composition according to claim 1, wherein the triazole derivative is prothioconazole.

11. The composition according to claim 1, further comprising an agriculturally acceptable support, carrier, filler and/or surfactant.

12. The composition according to claim 1, wherein (a) the pyridylethylbenzamide derivative of formula (I) is N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethyl-benzamide, (b) the triazole derivative capable of inhibiting the ergosterol biosynthesis is prothioconazole, and (c) the further fungicidal compound is tebuconazole.

13. A method for preventively or curatively controlling phytopathogenic fungi in a crop plant, comprising applying an effective and non-phytotoxic amount of the composition according to claim 1 to the plant, and/or to seed or fruit of the plant, and/or to the soil in which the plant is or will grow.

Description

EXAMPLE 1

Efficacy against Mycosphaerella Graminicola of a Mixture Containing N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethyl-benzamide (Compound 1) and Tebuconazole

[0081] The active ingredients tested are prepared by potter homogenisation in a mixture of acetone/tween/water . This suspension is then diluted with water to obtain the desired active material concentration.

[0082] Wheat plants (Scipion variety), sown on a 50/50 peat soil-pozzolana substrate in starter cups and grown at 12 C., are treated at the 1-leaf stage (10 cm tall) by spraying with the aqueous suspension described above. Plants, used as controls, are treated with an aqueous solution not containing the active material.

[0083] After 24 hours, the plants are contaminated by spraying them with an aqueous suspension of Mycosphaerella graminicola spores (500 000 spores per ml). The spores are collected from a 7-day-old culture. The contaminated wheat plants are incubated for 72 hours at 18 C. and at 100% relative humidity, and then for 21 to 28 days at 90% relative humidity.

[0084] Grading (% of efficacy) is carried out 21 to 28 days after the contamination, in comparison with the control plants.

[0085] The following table summarises the results obtained when tested compound 1 and tebuconazole alone and in a 1/1 weight ratio mixture.

TABLE-US-00001 Dose % Synergism (g/ha) Efficacy (Colby) Compound 1 15 25 31 65 Tebuconazole 15 15 31 15 Compound 1 + tebuconazole 15 + 15 75 +39 (Ratio 1/1) 31 + 31 80 +10

[0086] According to the Colby method, a synergistic effect of the mixtures tested has been observed.

EXAMPLE 2

Efficacy Against Erysiphe Graminis f. sp. Graminis of a Mixture Containing N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide (Compound 1) and Prothioconazole

[0087] The active ingredients tested are prepared by potter homogenisation in a mixture of acetone/tween/water . This suspension is then diluted with water to obtain the desired active material concentration.

[0088] Wheat plants (Audace variety) in starter cups, sown on 50/50 peat soil-pozzolana substrate and grown at 12 C., are treated at the 1-leaf stage (10 cm tall) by spraying with the aqueous suspension described above.

[0089] Plants, used as controls, are treated with an aqueous solution not containing the active material.

[0090] After 24 hours, the plants are contaminated by dusting them with Erysiphe graminis f. sp. tritici spores, the dusting being carried out using diseased plants.

[0091] Grading is carried out 7 to 14 days after the contamination, in comparison with the control plants.

[0092] The following table summarises the results obtained when tested compound 1 and prothioconazole alone and in a 1/2 weight ratio mixture.

TABLE-US-00002 Dose % Synergism (g/ha) Efficacy (Colby) Compound 1 125 20 62.5 0 Prothioconazole 250 60 125 0 Compound 1 + prothioconazole 125 + 250 85 +17 (Ratio 1/2) 62 + 125 70 +70

[0093] According to the Colby method, a synergistic effect of the mixtures tested has been observed.

EXAMPLE 3

Efficacy Against Botrytis Cinerea of a Mixture Containing N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide (Compound 1) and Propiconazole

[0094] The active ingredients tested are prepared by potter homogenisation in a mixture of acetone/tween/water . This suspension is then diluted with water to obtain the desired active material concentration.

[0095] Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a 50/50 peat soil-pozzolana substrate and grown at 18-20 C., are treated at the cotyledon Z11 stage by spraying with the aqueous suspension described above. Plants, used as controls, are treated with an aqueous solution not containing the active material.

[0096] After 24 hours, the plants are contaminated by depositing drops of an aqueous suspension of Botrytis cinerea spores (150,000 spores per ml) on upper surface of the leaves. The spores are collected from a 15-day-old culture and are suspended in a nutrient solution composed of:

[0097] 20 g/L of gelatine

[0098] 50 g/L of cane sugar

[0099] 2 g/L of NH4NO3

[0100] 1 g/L of KH2PO4

[0101] The contaminated gherkin plants are settled for 5/7 days in a climatic room at 15-11 C. (day/night) and at 80% relative humidity. Grading (% of efficacy) is carried out 5 to 7 days after the contamination, in comparison with the control plants.

[0102] The following table summarises the results obtained when tested compound 1 and propiconazole alone and in different weight ratio mixtures.

TABLE-US-00003 Dose % Synergism (ppm) Efficacy (Colby) Compound 1 12 0 37 30 111 80 Propiconazole 37 30 111 50 333 70 Compound 1 + propiconazole 37 + 333 100 21 (Ratio 1/9) 12 + 111 100 50 Compound 1 + propiconazole 37 + 111 100 +35 (Ratio 1/3) Compound 1 + propiconazole 37 + 37 80 +29 (Ratio 1/1)

[0103] According to the Colby method, a synergistic effect of the mixtures tested has been observed.

EXAMPLE 4

Efficacy against Erysiphe Graminis f. sp. Graminis of a Mixture Containing N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide (Compound 1) and Cyproconazole

[0104] The formulated (concentrated suspension) compounds are diluted with water to obtain the desired active material concentration Wheat plants (Audace variety) in starter cups, sown on 50/50 peat soil-pozzolana substrate and grown at 12 C., are treated at the 1-leaf stage (10 cm tall) by spraying with the aqueous suspension described above.

[0105] Plants, used as controls, are treated with an aqueous solution not containing the active material.

[0106] After 24 hours, the plants are contaminated by dusting them with Erysiphe graminis f. sp. tritici spores, the dusting being carried out using diseased plants.

[0107] Grading is carried out 7 to 14 days after the contamination, in comparison with the control plants.

[0108] The following table summarises the results obtained when tested compound 1 and cyproconazole alone and in a 2/1 weight ratio mixture.

TABLE-US-00004 Dose % Synergism (g/ha) Efficacy (Colby) Compound 1 62.5 10 Cyproconazole 31.2 15 Compound 1 + cyproconazole 62.5 + 31.2 60 +37 (Ratio 2/1)

[0109] According to the Colby method, a synergistic effect of the mixtures tested has been observed.

EXAMPLE 5

Efficacy Against Botrytis Cinerea of a Mixture Containing N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide Compound 1) and Difenconazole

[0110] The active ingredients tested are prepared by potter homogenisation in a mixture of acetone/tween/water . This suspension is then diluted with water to obtain the desired active material concentration.

[0111] Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a 50/50 peat soil-pozzolana substrate and grown at 18-20 C., are treated at the cotyledon Z11 stage by spraying with the aqueous suspension described above. Plants, used as controls, are treated with an aqueous solution not containing the active material.

[0112] After 24 hours, the plants are contaminated by depositing drops of an aqueous suspension of Botrytis cinerea spores (150,000 spores per ml) on upper surface of the leaves. The spores are collected from a 15-day-old culture and are suspended in a nutrient solution composed of:

[0113] 20 g/L of gelatine

[0114] 50 g/L of cane sugar

[0115] 2 g/L of NH4NO3

[0116] 1 g/L of KH2PO4

[0117] The contaminated gherkin plants are settled for 5/7 days in a climatic room at 15-11 C. (day/night) and at 80% relative humidity. Grading (% of efficacy) is carried out 5 to 7 days after the contamination, in comparison with the control plants.

[0118] The following table summarises the results obtained when tested compound 1 and difenconazole alone and in different weight ratio mixtures.

TABLE-US-00005 Dose % Synergism (ppm) Efficacy (Colby) Compound 1 37 0 111 80 Difenconazole 111 15 333 25 Compound 1 + difenconazole 37 + 111 80 +65 (Ratio 1/3) Compound 1 + difenconazole 111 + 111 100 +17 (Ratio 1/1) Compound 1 + difenconazole 111 + 333 80 +55 (Ratio 1/9)

[0119] According to the Colby method, a synergistic effect of the mixtures tested has been observed.

EXAMPLE 6

Efficacy Against Botrytis Cinerea of a Mixture Containing N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide (Compound 1) and Hexaconazole

[0120] The active ingredients tested are prepared by potter homogenisation in a mixture of acetone/tween/water . This suspension is then diluted with water to obtain the desired active material concentration.

[0121] Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a 50/50 peat soil-pozzolana substrate and grown at 18-20 C., are treated at the cotyledon Z11 stage by spraying with the aqueous suspension described above. Plants, used as controls, are treated with an aqueous solution not containing the active material.

[0122] After 24 hours, the plants are contaminated by depositing drops of an aqueous suspension of Botrytis cinerea spores (150,000 spores per ml) on upper surface of the leaves. The spores are collected from a 15-day-old culture and are suspended in a nutrient solution composed of:

[0123] 20 g/L of gelatine

[0124] 50 g/L of cane sugar

[0125] 2 g/L of NH4NO3

[0126] 1 g/L of KH2PO4

[0127] The contaminated gherkin plants are settled for 5/7 days in a climatic room at 15-11 C. (day/night) and at 80% relative humidity. Grading (% of efficacy) is carried out 5 to 7 days after the contamination, in comparison with the control plants.

[0128] The following table summarises the results obtained when tested compound 1 and hexaconazole alone and in a 1:27 weight ratio mixture.

TABLE-US-00006 Dose % Synergism (ppm) Efficacy (Colby) Compound 1 4 10 Hexaconazole 111 15 Compound 1 + hexaconazole 4 + 111 98 +19 (Ratio 1:27)

[0129] According to the Colby method, a synergistic effect of the mixtures tested has been observed.

EXAMPLE 7

Efficacy Against Erysiphe Graminis f. sp. Graminis of a Mixture Containing N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide (Compound 1) and Metconazole

[0130] The formulated compounds are diluted with water to obtain the desired active material concentration. Wheat plants (Audace variety) in starter cups, sown on 50/50 peat soil-pozzolana substrate and grown at 12 C., are treated at the 1-leaf stage (10 cm tall) by spraying with the aqueous suspension described above.

[0131] Plants, used as controls, are treated with an aqueous solution not containing the active material.

[0132] After 24 hours, the plants are contaminated by dusting them with Erysiphe graminis f. sp. tritici spores, the dusting being carried out using diseased plants.

[0133] Grading is carried out 7 to 14 days after the contamination, in comparison with the control plants.

[0134] The following table summarises the results obtained when tested compound 1 and metconazole alone and in a 8:1 weight ratio mixture.

TABLE-US-00007 Dose % Synergism (g/ha) Efficacy (Colby) Compound 1 250 40 Metconazole 31.2 50 Compound 1 + metconazole 250 + 31.2 80 +10 (Ratio 8:1)

[0135] According to the Colby method, a synergistic effect of the mixtures tested has been observed.

EXAMPLE 8

Efficacy Against Puccinia Recondita of a Mixture Containing N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide (Compound 1) and Epoxiconazole

[0136] The formulated compounds are diluted with water to obtain the desired active material concentration Wheat plants (Scipion variety) in starter cups, sown on 50/50 peat soil-pozzolana substrate and grown at 12 C., are treated at the 1-leaf stage (10 cm tall) by spraying with the aqueous suspension described above.

[0137] Plants, used as controls, are treated with an aqueous solution not containing the active material.

[0138] After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Puccinia recondita spores (100,000 spores per ml). The spores are collected from a 10-day-old contaminated wheat and are suspended in water containing 2.5 ml/l of tween 80 10%. The contaminated wheat plants are incubated for 24 hours at 20 C. and at 100% relative humidity, and then for 10 days at 20 C. and at 70% relative humidity. Grading is carried out 10 days after the contamination, in comparison with the control plants.

[0139] The following table summarises the results obtained when tested compound 1 and epoxiconazole alone and in different weight ratio mixtures.

TABLE-US-00008 Dose % Synergism (g/ha) Efficacy (Colby) Compound 1 62.5 0 250 0 Epoxiconazole 15.6 25 Compound 1 + epoxiconazole 250 + 15.6 80 +55 (Ratio 16:1) Compound 1 + epoxiconazole 62.5 + 15.6 85 +60 (Ratio 4:1)

[0140] According to the Colby method, a synergistic effect of the mixtures tested has been observed

EXAMPLE 9

Efficacy Against Botrytis Cinerea of a Mixture Containing N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide (Compound 1) and Myclobutanil

[0141] The formulated compounds are diluted with water to obtain the desired active material concentration.

[0142] Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a 50/50 peat soil-pozzolana substrate and grown at 18-20 C., are treated at the cotyledon Z11 stage by spraying with the aqueous suspension described above. Plants, used as controls, are treated with an aqueous solution not containing the active material.

[0143] After 24 hours, the plants are contaminated by depositing drops of an aqueous suspension of Botrytis cinerea spores (150,000 spores per ml) on upper surface of the leaves. The spores are collected from a 15-day-old culture and are suspended in a nutrient solution composed of:

[0144] 20 g/L of gelatine

[0145] 50 g/L of cane sugar

[0146] 2 g/L of NH4NO3

[0147] 1 g/L of KH2PO4

[0148] The contaminated gherkin plants are settled for 5/7 days in a climatic room at 15-11 C. (day/night) and at 80% relative humidity. Grading (% of efficacy) is carried out 5 to 7 days after the contamination, in comparison with the control plants.

[0149] The following table summarises the results obtained when tested compound 1 and myclobutanil alone and in different weight ratio mixtures.

TABLE-US-00009 Dose % Synergism (ppm) Efficacy (Colby) Compound 1 12.3 0 37 50 Myclobutanil 333 0 Compound 1 + myclobutanil 12.3 + 333 53 +53 (Ratio 1:27) Compound 1 + myclobutanil 37 + 333 70 +20 (Ratio 1:9)

[0150] According to the Colby method, a synergistic effect of the mixtures tested has been observed.

EXAMPLE 10

Efficacy Against Puccinia Recondita of a Mixture Containing N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide (Compound 1) and Triadimenol

[0151] The active ingredients tested are prepared by potter homogenisation in a mixture of acetone/tween/water . This suspension is then diluted with water to obtain the desired active material concentration.

[0152] Wheat plants (Scipion variety) in starter cups, sown on 50/50 peat soil-pozzolana substrate and grown at 12 C., are treated at the 1-leaf stage (10 cm tall) by spraying with the aqueous suspension described above.

[0153] Plants, used as controls, are treated with an aqueous solution not containing the active material.

[0154] After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Puccinia recondita spores (100,000 spores per ml). The spores are collected from a 10-day-old contaminated wheat and are suspended in water containing 2.5 ml/l of tween 80 10%. The contaminated wheat plants are incubated for 24 hours at 20 C. and at 100% relative humidity, and then for 10 days at 20 C. and at 70% relative humidity. Grading is carried out 10 days after the contamination, in comparison with the control plants.

[0155] The following table summarises the results obtained when tested compound 1 and triadimenol alone and in a 1:1 weight ratio mixture.

TABLE-US-00010 Dose % Synergism (g/ha) Efficacy (Colby) Compound 1 250 0 Triadimenol 250 50 Compound 1 + triadimenol 250 + 250 70 +20 (Ratio 1:1)

[0156] According to the Colby method, a synergistic effect of the mixtures tested has been observed.

EXAMPLE 11

Efficacy against Sphaerotheca Fuliginea of a Composition Containing N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethyl-benzamide (Compound 1) and Fenhexamid

[0157] The formulated compounds are diluted with water to obtain the desired active material concentration

[0158] Gherkin plants (Vert petit de Paris variety) in starter cups, sown on a 50/50 peat soil-pozzolana substrate and grown at 20 C./23 C., are treated at the 2-leaves stage by spraying with the aqueous suspension described above. Plants, used as controls, are treated with an aqueous solution not containing the active material.

[0159] After 24 hours, the plants are contaminated by spraying them with an aqueous suspension of Sphaerotheca fuliginea spores (100 000 spores per ml). The spores are collected from a contaminated plants .The contaminated gerkhin plants are incubated at about 20 C./25 C. and at 60/70% relative humidity.

[0160] Grading (% of efficacy) is carried out 21 days after the contamination, in comparison with the control plants.

[0161] The following table summarises the results obtained when tested compound 1 and fenhexamid alone and in a 1:9 weight ratio mixture.

TABLE-US-00011 Dose % Synergism (ppm) Efficacy (Colby) Compound 1 4.1 28 Fenhexamid 37 35 Compound 1 + fenhexamid 4.1 + 37 74 +21 (Ratio 1:9)

[0162] According to the Colby method, a synergistic effect of the mixtures tested has been observed.

EXAMPLE 12

Efficacy Against Mycosphaerella Graminicola of a Mixture Containing N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide (Compound 1) and Prochloraz

[0163] The formulated compounds are diluted with water to obtain the desired active material concentration

[0164] Wheat plants (Scipion variety), sown on a 50/50 peat soil-pozzolana substrate in starter cups and grown at 12 C., are treated at the 1-leaf stage (10 cm tall) by spraying with the aqueous suspension described above. Plants, used as controls, are treated with an aqueous solution not containing the active material.

[0165] After 24 hours, the plants are contaminated by spraying them with an aqueous suspension of Mycosphaerella graminicola spores (500 000 spores per ml). The spores are collected from a 7-day-old culture .The contaminated wheat plants are incubated for 72 hours at 18 C. and at 100% relative humidity, and then for 21 to 28 days at 90% relative humidity.

[0166] Grading (% of efficacy) is carried out 21 to 28 days after the contamination, in comparison with the control plants.

[0167] The following table summarises the results obtained when tested compound 1 and prochloraz alone and in a 1:4 weight ratio mixture.

TABLE-US-00012 Dose % Synergism (g/ha) Efficacy (Colby) Compound 1 62.5 77 Prochloraz 250 54 Compound 1 + Prochloraz 62.5 + 250 98 +9 (Ratio 1/4)

[0168] According to the Colby method, a synergistic effect of the mixtures tested has been observed.

EXAMPLE 13

Efficacy Against Botrytis Cinerea of a Mixture Containing N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide (Compound 1) and Fenpropimorph

[0169] The formulated compounds are diluted with water to obtain the desired active material concentration.

[0170] Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a 50/50 peat soil-pozzolana substrate and grown at 18-20 C., are treated at the cotyledon Z11 stage by spraying with the aqueous suspension described above. Plants, used as controls, are treated with an aqueous solution not containing the active material.

[0171] After 24 hours, the plants are contaminated by depositing drops of an aqueous suspension of Botrytis cinerea spores (150,000 spores per ml) on upper surface of the leaves. The spores are collected from a 15-day-old culture and are suspended in a nutrient solution composed of:

[0172] 20 g/L of gelatine

[0173] 50 g/L of cane sugar

[0174] 2 g/L of NH4NO3

[0175] 1 g/L of KH2PO4

[0176] The contaminated gherkin plants are settled for 5/7 days in a climatic room at 15-11 C. (day/night) and at 80% relative humidity. Grading (% of efficacy) is carried out 5 to 7 days after the contamination, in comparison with the control plants.

[0177] The following table summarises the results obtained when tested compound 1 and fenpropimorph alone and in 1:2 weight ratio mixture.

TABLE-US-00013 Dose % Synergism (g/ha) Efficacy (Colby) Compound 1 31.2 20 62.5 30 Fenpropimorph 62.5 10 125 30 Compound 1 + fenpropimorph 31.2 + 62.5 60 +32 (Ratio 1:2) 62.5 + 125 80 +29

[0178] According to the Colby method, a synergistic effect of the mixtures tested has been observed.

EXAMPLE 14

Efficacy Against Erysiphe Graminis f. sp. Graminis of a Mixture Containing N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide (Compound 1) and Spiroxamine

[0179] The formulated compounds are diluted with water to obtain the desired active material concentration Wheat plants (Audace variety) in starter cups, sown on 50/50 peat soil-pozzolana substrate and grown at 12 C., are treated at the 1-leaf stage (10 cm tall) by spraying with the aqueous suspension described above.

[0180] Plants, used as controls, are treated with an aqueous solution not containing the active material.

[0181] After 24 hours, the plants are contaminated by dusting them with Erysiphe graminis f. sp. tritici spores, the dusting being carried out using diseased plants.

[0182] Grading is carried out 7 to 14 days after the contamination, in comparison with the control plants.

[0183] The following table summarises the results obtained when tested compound 1 and spiroxamine alone and in a 4:1 weight ratio mixture.

TABLE-US-00014 Dose % Synergism (g/ha) Efficacy (Colby) Compound 1 500 44 Spiroxamine 125 0 Compound 1 + spiroxamine 500 +125 72 +28 (Ratio 4:1)

[0184] According to the Colby method, a synergistic effect of the mixtures tested has been observed.

EXAMPLE 15

Efficacy Against Botrytis Cinerea of a Mixture Containing N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide (Compound 1) and Triforine

[0185] The formulated compounds are diluted with water to obtain the desired active material concentration.

[0186] Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a 50/50 peat soil-pozzolana substrate and grown at 18-20 C., are treated at the cotyledon Z11 stage by spraying with the aqueous suspension described above. Plants, used as controls, are treated with an aqueous solution not containing the active material.

[0187] After 24 hours, the plants are contaminated by depositing drops of an aqueous suspension of Botrytis cinerea spores (150,000 spores per ml) on upper surface of the leaves. The spores are collected from a 15-day-old culture and are suspended in a nutrient solution composed of:

[0188] 20 g/L of gelatine

[0189] 50 g/L of cane sugar

[0190] 2 g/L of NH4NO3

[0191] 1 g/L of KH2PO4

[0192] The contaminated gherkin plants are settled for 5/7 days in a climatic room at 15-11 C. (day/night) and at 80% relative humidity. Grading (% of efficacy) is carried out 5 to 7 days after the contamination, in comparison with the control plants.

[0193] The following table summarises the results obtained when tested compound 1 and triforine alone and in different weight ratio mixtures.

TABLE-US-00015 Dose % Synergism (ppm) Efficacy (Colby) Compound 1 37 50 Triforine 37 0 111 15 Compound 1 + triforine 37 + 37 65 +15 (Ratio 1:1) Compound 1 + triforine 37 + 111 70 +13 (Ratio 1:3)

[0194] According to the Colby method, a synergistic effect of the mixtures tested has been observed.

EXAMPLE 16

Efficacy Against Botrytis Cinerea of a Mixture Containing N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide (Compound 1) and Bitertanol

[0195] The formulated compounds are diluted with water to obtain the desired active material concentration.

[0196] Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a 50/50 peat soil-pozzolana substrate and grown at 18-20 C., are treated at the cotyledon Z11 stage by spraying with the aqueous suspension described above. Plants, used as controls, are treated with an aqueous solution not containing the active material.

[0197] After 24 hours, the plants are contaminated by depositing drops of an aqueous suspension of Botrytis cinerea spores (150,000 spores per ml) on upper surface of the leaves. The spores are collected from a 15-day-old culture and are suspended in a nutrient solution composed of:

[0198] 20 g/L of gelatine

[0199] 50 g/L of cane sugar

[0200] 2 g/L of NH4NO3

[0201] 1 g/L of KH2PO4

[0202] The contaminated gherkin plants are settled for 5/7 days in a climatic room at 15-11 C. (day/night) and at 80% relative humidity. Grading (% of efficacy) is carried out 5 to 7 days after the contamination, in comparison with the control plants.

[0203] The following table summarises the results obtained when tested compound 1 and bitertanol alone and in a 1:9 weight ratio mixture.

TABLE-US-00016 Dose % Synergism (ppm) Efficacy (Colby) Compound 1 12.3 5 Bitertanol 333 0 Compound 1 + bitertanol 12.3 + 333 95 +90 (Ratio 1:9)

[0204] According to the Colby method, a synergistic effect of the mixture tested has been observed.

EXAMPLE 17

Efficacy Against Erysiphe Graminis f. sp. Graminis of a Mixture Containing N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide (Compound 1), Spiroxamine and Prothioconazole

[0205] The formulated compounds (Compound 1 and a mix of spiroxamine (300 g/l) and prothioconazole (160 g/l) are diluted with water to obtain the desired active material concentration Wheat plants (Audace variety) in starter cups, sown on 50/50 peat soil-pozzolana substrate and grown at 12 C., are treated at the 1-leaf stage (10 cm tall) by spraying with the aqueous suspension described above.

[0206] Plants, used as controls, are treated with an aqueous solution not containing the active material.

[0207] After 24 hours, the plants are contaminated by dusting them with Erysiphe graminis f. sp. tritici spores, the dusting being carried out using diseased plants.

[0208] Grading is carried out 7 to 14 days after the contamination, in comparison with the control plants.

[0209] The following table summarises the results obtained when tested compound 1 and the mix of spiroxamine and prothioconazole alone and in a 8:1 weight ratio mixture.

TABLE-US-00017 Dose % Synergism (g/ha) Efficacy (Colby) Compound 1 125 0 Spiroxamine + 15.6 45 prothioconazole Compound 1 + spiroxamine + 125 + 15.6 95 +50 prothioconazole (Ratio 8:1)
According to the Colby method, a synergistic effect of the mixtures tested has been observed.