CS247090B2 - Synergicaly acting fungicide agent - Google Patents

Abstract

A synergistic fungicidal agent containing on its total weight by weight 5 to 85% of the active substance consisting of " 3,5-dinitro-4-chlorobenzoic acid derivative general formula ,.FROM"- wherein R is alkyl of 1 to 6 carbon atoms, and a 1,2,4-triazole derivative.

Description

The composition according to the invention is suitable for the treatment of various plant cultures against numerous fungi, for example for the sowing of seed seeds or for the treatment of various parts of plants.

One type of active ingredient of the synergistic fungicidal composition of the invention, methyl 3,5-dinitro-4-chlorobenzoate and isopropyl 3,5-dinltro-4-chlorobenzoate and their activity against fungi Alternaria cleraceae and Sclerotinia fructicola, are known from U.S. Pat. No. 2,841,522. Compounds of formula (IV) containing a heteroaromatic ring having several nitrogen atoms are also known.

The contacting action of 3,5-dinitro-4-chlorobenzoic acid esters at various locations in plants is not practiced at all, although they are known compounds. The main reason is probably the fact that although these compounds are very effective in field conditions, they damage the protected plant when used at optimal doses. Therefore, a considerable risk of phytotoxicity must be taken into account when using them. There are also problems with the use of systemic fungicides having specific sites of action.

Methyl (1H) benzimidazol-2-ylcarbamate metabolizing compounds of formula (IV) have excelled in their fungicidal action when introduced, but after 1960 there has been an increasing reference in the literature to developing fungal resistance to these compounds upon repeated use. .

The development of mutational resistance to the action of systemic fungicides having certain specific actions is known in the literature. For example, in G. G. Georpoules: Antifungal Compounds and in Sisler: Development of Fungal Resistance to Funglcldes, New York 1977, pp. 493-495, there are numerous references to this problem.

Taking into account, notwithstanding the possibility of some resistance, that the use of systemic fungicides has some advantages in combating fungi, it would not be wise to exclude them from plant protection practice. This is supported by the fact that the use of these fungicides now and in the future is under constant control by experts. The extraordinary advantages resulting from the system properties cannot be overlooked. Therefore, research into solving resistance problems against these fungicides is increasingly intensive.

These research efforts focus on the following tasks: to prevent genes with higher resistance; mitigating changes in the combination of strains with a pathogenic population and mitigating the increase in resistance of strains with a pathogenic population and mitigating the increase in resistance of strains of the current population. Of the possible routes, it seems promising to detect and adapt for plant growing technology with a mixture of fungicides based on fun247090 gicides with certain specific modes of action.

These efforts have resulted in combined fungicidal agents from manufacturers of plant protection products such as Epidor ^R from Rohm and Haas Co. (containing 10% benomyl and 62% mancozeb) or Trimidal ^R from Eli and Lilly Co. (containing by weight 8% nuarimol and 32% manebuj and other similar compositions.

Hungarian Patent No. 158,608 also relates to a composition comprising 2,3-dihydro-6-methyl-1,4-oxathiine-6-carboxanilide having a specific action in admixture with 8-hydroxy-quinoline with its metal salt; this composition has various specific actions.

In the course of the research in connection with the present invention, the efficacy of the compounds of the formula I was first examined and then the active compound mixtures. The aim of this research was to determine the usefulness of a compound of formula I together with known systemic fungicides.

The activity of the compounds of the formula I was investigated in a liquid medium with respect to seven fungal species at a concentration of 0.1 to 1000 ppm of active ingredient. The results obtained are shown in Table I.

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Further investigations were carried out to determine the optimal weight ratio of the active ingredients in the synergistic fungicidal composition of the invention and to determine a useful dose of the fungicidal composition. Surprisingly, it has been found that the synergistic action is manifested at a clearly defined weight ratio of the active ingredients.

Accordingly, the present invention provides a synergistic fungicidal composition comprising, in addition to a 3,5-dinitro-4-chlorobenzoic acid derivative of the formula I wherein R is a C 1 -C 6 alkyl group, a 1,2,4-triazole derivative of the formula IV wherein R 5 is hydrogen, phenyl, phenoxy optionally substituted with phenyl or halogen or is benzyl substituted with halogen atoms, R 6 is hydrogen or trifluoromethylphenyl and R 7 is phenyl or one of the groups of formula (c), {dj and (e) as described above, wherein R 6 is C 1 -C 4 alkyl, wherein the weight ratio of the active compound of the formula I to the active compound of the formula IV is 1: 2 to 14: 1.

The 3,5-dinitro-4-chlorobenzoic acid derivatives of the formula I, one of the active compounds of the synergistic fungicidal agent according to the invention, are esters in which R represents an alkyl group having 1 to 6 carbon atoms, preferably having 1 to 4 atoms. carbon and in particular methyl or ethyl.

In the compounds of formula (IV), R5 is hydrogen, phenyl, phenoxy optionally substituted by phenyl or halogen or benzyl substituted by one or two halogen atoms, the halogen atom preferably being a chlorine atom. R6 represents a hydrogen atom or a thio / methylphenyl group and R7 represents a phenyl group or one of the groups of formula (c), (dj and (e). In the group of formula (d) the butyl group is preferably tertiary. of formula (e), R 5 represents an alkyl group having 1 to 4 carbon atoms, preferably 2 to 3 carbon atoms.

The weight ratio of the compound of formula I to the compound of formula IV is preferably 1: 2 to 14: 1.

The dosage form of the composition of the invention may be adapted to the substrate to which the fungicidal composition of the invention is applied and the requirements of use. It may be a mordant in the form of a powder or a suspension; a solid or liquid spray applied to the plant; emulsifiable concentrate, powder and the like. Liquid and / or solid carriers, adjuvants and other additives according to the formulation requirements and used generally in the manufacture of plant protection products may be used to prepare the fungicidal composition of the invention. The total active ingredient content of the composition may be from 5 to 85% by weight.

Table 2 shows the results obtained from the tests on the most advantageous mixtures of compounds against a given fungal species, the most advantageous synergistic ratios of the components of the effective, medium application rates with respect to the total active substance content and the characteristics of the compositions for the intended use.

Mushroom species Mixture Ratio Synergic Medium Dose Formulation of active ingredients of the active ingredients

Anti-methyl 3,5-dinitro-4-chlorobenzoate: 1,5: 1 to 3: 1 0,55 kg / t 30% pickling powder

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247993

A particular advantage of the composition according to the invention is that it enriches the range of pesticides with a new, highly effective composition protecting a broad spectrum of plants, polluting the biosphere less during production and use, since it can be used in smaller quantities due to the synergistic action of the ingredients. Another advantage is the fact that farmers do not have to give up the well-known systemic fungicides, which they would slowly have to leave because of the evolving resistance of fungi to the action of these agents.

The composition according to the invention and its fungicidal activity are illustrated by the following examples, which are not to be construed as limiting. The percentages are always mentioned by weight.

Example 1

For the dressing of autumn wheat seeds, a mordant containing a total of 30% active ingredients in suspension is prepared using methyl 3,5-dinitro-4-chlorobenzoate (DNCB-Me) together with methyl 1H-benzimidazol-2-ylcarbamate (CARBENDAZIM) or 1- (4-chlorophenoxy) -1- (1H-1,2,4-triazol-1-yl) -3,3-dimethyl-2-butanol (TRIADIMENOL) in the mixtures listed in Table 3. The active ingredient ratio is shown in Tables 4, 5 and 6.

Table 3

Active substance / mixture

DCNB-Me + CARBENDAZIM

DCNB-Me + TRIADIMENOL ethylene glycol cresol formaldehyde condensation product film-forming polymer Mowilit DM-21 antifoam Silicon SRE dye Rhodamin 2B4 demineralized water

The efficacy of mixtures A and B is studied under laboratory and field conditions with regard to the disease of autumn wheat shoots.

Part of the autumn wheat seed MV 8 is largely infected with Fusarium spp. and 0.2 wt. Tilletia sporules before pickling. Grains infected with Fusarium spp. or Fusarium spp. and Tilletia are pickled with doses of the studied mixtures as shown in Tables 4, 5 and 6.

Seeds infected with Fusarium spp. and moA B% - - 30%% 7%% 6%% 16%% 1%% 2%% 38% are subjected to laboratory testing. For each treatment, 200 seeds are placed in Papaviza selective broth and incubated for 10 days at 20 to 22 ° C by diffusion illumination. The percentage of germination, then the percentage of infection by Fusarium spp. is evaluated under a microscope. 8 parallel tests are always performed and the results are shown in Table 4.

Table 4

Activity against Fusarium spp.

Dose kg / t DNCB-Me CARBENDAZIM Germination % Infection rate of Fusarium spp. % 0,10 0,80 102.5 12.0 0.30 + 0.60 107.7 3.5 0.45 + 0.45 106.6 3.0 0.60 + 0.30 107.7 2.5 0.80 + 0.10 105.6 22.1 0,60 - 101.7 36.0 0.90 - 103.9 25.2 - 0,60 102.4 18.2 - 0.90 104.1 15.5 untreated 100.0 62.0 0.10 + 0.30 101.5 3.5 0.30 + 0.20 105.2 1.5 0.45 + 0.15 107.2 1.0 0.60 + 0.10 108.8 2.2 0.80 + 0.05 107.5 18.1 0,60 - 101.7 36.0 0.90 - 103.9 25.2 - 0,30 103.3 10.5 - 0,40 103.8 100.0 8.5 untreated control 62.0

247099

Seeds, also infected with Tilletia, shall be tested in a field on 2 m ² plots in three randomly arranged parallels. Seeds are sown on November 28 in rows 12 cm at 80 g per plot; 157 seeds were sown in the third row of each plot to evaluate phytotoxicity. This evaluation was carried out on 10 April of the following year for Table 5 to determine the number and height of the emerging plants and to assess the general impression of the plants. Efficacy against Tilletia is evaluated at harvest time by testing each ear and determining the number of mature ears and ears infected with Tilletia. The mean values of the three plots are shown in Tables 5 and 6.

Phytotoxicity studies

Dose kg / t DNCB-Me + CARBENDAZIM Emergency (° / drawbar) Plant height (%) 0.1 + 0.8 97.6 101.5 0.3 -1- 0.6 139.0 103.7 0.45 + 0.45 140.2 106.2 0.6 + 0.3 105.1 102.2 0.8 + 0.1 98.3 96.6 0,6 - 107.5 98.8 0,9 - 98.3 95.2 - 0,6 100.2 105.2 - 0,9 109.4 102.2 untreated control 100.0 100.0 Dose kg / t Emergence (%) Plant height {%) DNCB-Me + TRIADIMENOL 0.1 + 0.3 105.0 100.5 0,3 4- 0,2 127.4 108.0 0.45 4- 0.15 145.5 108.6 0,6 4- 0,1 106.4 102.3 0.8 4 “0.05 99.4 99.5 0,6 - 107.5 98.8 0,9 - 98.3 95.2 - 0,3 100.2 105.2 - 0,4 111.5 104.5 untreated control 100.0 100.0 Table 6 Effectiveness against Tilletia Dose kg / t Healthy ears Infected ears DNCB-Me + CARBENDAZIM piece / land piece / land 0.1 + 0.8 912.7 3.7 0,3 4- 0,6 1 247.5 1.3 0.45 4- 0.45 1 311.2 1.7 0,6 4- 0,3 1147.8 0.0 0.8 4- 0.1 956.3 10.0 0,6 - 1 024,7 6.3 0,9 - 1 079.7 5.3 - 0,6 927.4 18.4 - 0,9 951.9 17.7 control infected with a fungus 804.7 151.7 Tilletia untreated control 933.0 14.0 0.1 + 0.3 957.7 10.0 0.3 + 0.2 1 346,5 4.2 0.45 4 “0.15 1 439,3 0.0 0,6 4- 0,1 986.1 3.0 0.8 4- 0.05 1012.8 9.6 0,6 - 1 024,7 6.3 0,9 - 1 079.7 5.3 - 0,3 901.5 12.0 - 0,4 924.7 12.7 control infected with Tilletia 804.7 151.7 untreated control 933.0 14.0

Based on these tests, the efficacy against Fusarium spp. synergistic at 0.3 + 0.6; 0.45 + 0.45 and 0.6 + 0.3 kg / t, i.e. when treated with active ingredients in a ratio of 1: 2 to 2: 1 compared to the efficacy of DNCB-Me or CARBENDAZIM used individually. However, pickling with DNCB-Me + TRIDIMENOL exhibits higher doses of 0.3 + -f- 0.2 and 0.45 + 0.15 kg / t, i.e. higher in the treatment with active substances in a ratio of 1.5: 1 to 3: 1 higher efficacy than would be expected with separate use of both formulations. In this treatment, the percentage of shoots is also improved. In field trials, treatment with the above-mentioned doses in the above active compound ratios results in both an improvement in the number of emerging plants and an improvement in plant height, number and rate of ear infection.

Table 7

Folder / Content A (%)

DNCB-Me + CARBENDAZIM 73.7 (technical, 95% pure)

DNCB-Me + TRIADIMEFON - (technical, 95% pure)

DNCB-Me + PROPICONAZOLE - (technical, 95% pure)

DNCB-Me + FLUTRIMEZOLE (technical, 95% pure)

Cab-O-Sil Synthetic Carrier 10.0

Dissipative agent

Atlox 4,862 3.0

Atlox Wetter 4 995 3.0

Polyphon O 4.0 dispersant

Kaolin carrier 6.3

Biological tests shall be carried out in the case of winter wheat of the species Jubilejnaja-50 on plots of 10 m ² , the tests being carried out on four plots. The fungicidal treatment is carried out at a volume of 600 l / ha at the end of the cob formation. Fusarium spp. ears are evaluated by examining 2 X 100 ears of each plot 10 days after spraying.

Yield from the plot is determined after harvest, Table-8 Batch kg / ha

DNCB-Me + CARBENDAZIM

Example 2

To investigate the efficacy against Fusarium fungus infection, attacking ears of autumn wheat, a formulation was prepared according to Table 7 using methyl 3,5-dinitro-4-chlorobenzoate (DNCB-Me) and methyl 1H-benzimidazol-2-yl-carbamate ( CARBENDAZIM), 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butanone (TRIADIMEFON), 1- (2- (2 (4-dichlorophenyl) -4-propyl-1,3-dioxolan-2-yl] methyl-1H-1,2,4-triazole (PROPICONAZOLE) and 1- [diphenyl- (3-trifluoromethyl) phenyl] methyl-1H -1,2,4-triazole (FLUOTRIMEZOLE) in the form of a wettable powder (WP) containing by weight 70%

substances. The active compound ratio is shown in Tables 8, 9, 10 and 11. B (%) C (%) D (%) - - - 73.7 - - —- 73.7 - - - 73.7 10.0 10.0 10.0 3.0 3.0 3.0 3.0 3.0 3.0 4.0 4.0 4.0 6.3 6.3 6.3

a sample of the harvested grain is sampled and the total grain infection rate of Fusarium spp. by examining 2 X 100 grains of the test culture microscopically after incubation in a Papaviza medium at 20 ° C for eight days. Preliminary surface disinfection is performed in conjunction with the assessment of the rate of internal infection. The results of these tests are shown in Tables 8, 9, 10 and 11.

Fusarium spp. (%) Mass

Crop Grain Harvest grain (total) (internal) kg / 10 m ²

0.85 + 0.15 0.80 + 2.25 0.75 + 0.25 - 0.25 - 0.50

0,9 -

1.8 Untreated control

0.20 6.50 4.25 6.55 0.50 8.20 6.50 6.42 1.00 9.50 7.00 6.44 7.30 18.20 15.25 6.11 6.50 16.00 11.75 6.01 5.00 13.25 11.50 6.10 4.25 11.50 11.50 3.13 11.50 38.75 31.25 5,52

Dose kg / ha Fusarium spp. (° / o) Weight

DNCB-Me + TRIAD1MEFON Klas Grain Harvest grain (total) (internal) kg / 10 m ^z

247099

Table 9

0.85 + 0.05 0.25 6.0 3.5 6.35 0.80 -) - 0.10 0.20 4,5 3.0 6.62 0.75 + 0.15 0.05 2,0 1.5 6.67 - 0,15 4.50 8.5 6.0 6.15 0.20 4.00 8.0 5.0 6.22 0,9 - 5.00 13.25 11.5 6.10 1,8 - 4.25 11.50 11.5 3.13 Untreated control 11.50 38.75 31.25 5,52 Table 10 Rate kg / ha Infection Rate Fusarium spp. (%) Mass DNCB-Me -j- PROPICONAZOLE Ear Grain (overall) Grain (internally) harvest kg / 10 m ² 0.85 + 0.15 5.0 9.0 5.0 6.45 0.80 + 0.20 3.5 4,5 3.5 6.42 0.75 + 0.25 1.0 15.5 3.25 6.15 - 0,25 7.0 14.5 18.5 5.75 0.30 6.5 12.5 15.5 5.90 0.9 5.0 13.25 11.5 6.10 1,8 - 4.25 11.50 11.5 3.13 Untreated control 11.50 38.75 31.25 5,52 Table 11 Rate kg / ha Fusarium spp. (° / o Mass DNCB ~ | - FLUOTRIMEZOLE Ear Grain (overall) Grain (internally) harvest kg / 10 m ² 0.85 + 0.15 3.5 9.5 8.0 5.95 0.80 + 0.20 2.5 6.0 7.0 6.05 0.75 0.25 1.5 6.5 7.5 6.15 - 0,25 6.5 15.5 12.5 5.85 0.50 9.0 19.0 16.0 5.62 0,9 - 5.0 13.25 11.5 6.10 1,8 - 4.25 11.50 11.50 3.13 Untreated control 11.50 38.75 31.25 5,52

Example 3

To investigate the activity against the fungus Venturia inaequalis (causing scab), a formulation was prepared using methyl 3,5-dinitro-4-chlorobenzoate (DNCB-Me and 1- (2- (2,4-dichlorophenyl) -4-ethyl) -1,3-dioxolan-2-yl] -methyl-1H-1,2,4-triazole (ETA-CONAZOLE), 1- (4-phenylphenoxy) -3,3-dimethyl-1- (1H- 1,2,4-triazol-1-yl-2-butanol (BITERTANOL) and alpha- (2-chlorophenyl) -alpha- (4-chlorophenyl) -5-pyrimidinylmethanol (PHEN ARIMOL) as an emulsifiable concentrate containing by weight total 20% of the active substances according to Table 12. The active ingredient ratio is indicated in the 'dose' column of Table 13.

Table 12 Folder / Contents

DNCB-Me + ETACONAZOLE

DNCB-Me + BITERTANOL

DNCB-Me + PHENARIMOL

Cyclohexanone as solvent

Xylene as solvent

Emulsifier Atlox 4,858 Emulsifier Atlox 8,916 Emulsifier Atlox 4,851 Isophorone as a solvent Emulsifier Tensiofix D-120 Emulsifier Tensiofix AS Tensiofix Emulsifier B-7 425 Solvent HAN

Emulsifying agent Arcopal N080 Emulsifying agent Emulsogen EL Emulsifying agent Sapogenate T-180

Biological tests shall be carried out in two rows in the case of a 20-year-old apple tree species Jonatan, grown on plots of 0.5 hectare at 7.5 X 4.5 m intervals. The fungicidal product is used 9 times during the vegetation period from 1 to 2 weeks using a water volume of 1000 liters per hectare using a Kartitox Na-10 syringe equipped with a

A (%) B%] C (%)

20 May 20 May 20 May 20 May - 40 50 38 - 3 - - 3.5 - - 3.5 - - - 30 - - 3.5 - - 3.5 - -. 5.0 - - - 30 - - 5.0 - - 1.5 - - 3.5

Tee-Jet. The leaf infection rate is assessed twice in ten trees at the end of the first and second stages of shoot growth. Always examine 100 liters of each tree. The rate of infection of the fruit and the degree of infestation are assessed on ten trees before harvest. Examine 50 fruits from each tree. Results See Table 13.

Table 13

Rate kg / ha DNCB-Me + ETCONAZOLE Leaf infection rate 1. 2nd evaluation% Fetal infection rate (%) Damage fruits (%) 1 + 0.15 0 7.2 2.2 0 1.25 + 0.1 0 8.2 2.3 0 1.50 + 0.075 1.4 9.8 2.7 10.5 1,50 + - 14.6 32.3 12.5 10.7 2 - 9.5 9.5 10.2 20.4 - 0,15 10.4 28.5 5.0 0 - 0,2 9.3 26.4 4.7 10.0 Untreated control 27.4 62.6 41.5 0 Rate kg / ha Rate infe leaf curl Infection rate Damage DNCB-Me + BITERTANOL 1. 2. fruits fruits rating% (%) (%) 1 + 0.15 0 5.3 1.9 0 1.25 0.10 0 8.0 2.2 0 1.50 + 0.075 5.1 11.2 2.7 10.0 1,50 + - 14.6 32.3 12.5 10.7 2 - 9.5 9.5 10.2 20.4 - 0,15 5.3 21.5 3.8 0 - 0.20 5.9 19.9 2.8 11.1 Untreated control 27.4 62.6 41.5 0

Rate kg / ha

DNCB-Me + PHENARIMOL

Leaf infection rate Infection rate Evaluation 1. 2. fruits fruits rating% (%) (%)

1.00 + 0.150 0 5.5 2.1 0 1.25 + 0.100 0 6.3 3.2 0 1.50 + 0,075 2.3 9.5 2.3 10.3 1.50 - 14.6 32.3 12.5 10.7 2.00 - 9.5 9.5 10.2 20.4 - 0.150 6.8 22.4 4.6 0 - 0.200 7.2 18.6 3.1 11.3 Untreated control 27.4 62.6 41.5 0

It is apparent from Table 13 that a dose of 1.15 to 1.35 kg / ha of a formulation containing a mixture of investigational active substances, i.e. DNCB-Me together with either ETACONAZOLE or BITERTANOL or PHENARINOL, exhibits a syntergic action with respect to Venturia Inaequalis weight ratio of active ingredients 6.6: 1 to 12.5: 1.

Example 4

To investigate activity against the fungus Peronospora manshurica (fungus attacking soybean), a fungicidal composition was prepared using methyl 3,5-dinitro-4 chlorobenzoate (DNCB-Me) and 1- (2,4-dichlorobenzyl) -3,3-dimethyl- 1- (1H-1,2,4-triazol-1-yl) -2-butanol (DICLOBENTRAZOLE) in the form of a wettable powder (WP) containing 70% by weight of the active substances according to Table 14. The weight ratio of the active substances is given in Table 15 .

Table 14

Folder / Contents

DNCB-Me + DICHLOBENTRAZOLE 70%

Synthetic carrier -Cab-0-Sil 15%

Wetting agent Netzer IS 3%

Dispersing agent "Dlspergiermittel SI" 6%

Polyphon O 6% Dispersant

Bioassays are performed on Ewans soybeans. The fungicidal treatment with the test composition is carried out three times (at a height of 40 cm soy, at the beginning of flowering and at full bloom). Spraying is performed with a water volume of 400 l / ha using a RAH-14-K-10 field sprayer. 10 X 10 plants were scored on day 16 after the last treatment. Calculate the results using the following scale:

Scale used to assess infection rate:

simple infection infection less than 5% infection 6 to 10% infection 11 to 25% infection 26 to 50% infection 51 to 75% infection 76 to 100%

For evaluation, the number of infected plants is calculated as a percentage (F%) of the total number of plants examined and the infection rate index is determined according to this equation "3l X fj where

F _t index of infection rate as well as individual values of the assessment scale

L number of plants subjected to individual assessment by scale (frequency) n total number of plants examined.

The lower the Fj value, the more effective the fungicidal composition. The test results are shown in Table 15 as well as the degree of leaf damage.

For a dose of 2.1 kg / ha of the total amount of active substances, the biological activity, as shown in the table, is most favorable at a weight ratio of DNCB-Me to DICLOBENTRAZOL of 1: 2 to 1.1: 1. The efficacy of the synergistic mixture exceeds that of the same doses of active ingredients, but used alone.

Rate kg / ha Number of plants according to the rating scale Damage (% 1

DNCB-Me + 0 1 2 3 4 5 6 F% F _t

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Example 5

To investigate the efficacy against Ustilago sp. prepare the preparation using methyl 3,5-dinltro-4-chlorobenzoate (DNCB-Me) and alpha- (2-chlorophenyl) -alpha- (4-fluorophenyl) -5-pyrimidinylmethanol (NUARIMOL) or 1Table 1Θ

Folders / Content

DNCB-Me + NUARIMOL

DNCB-Me + TRIADIMENOL Wetting agent Tinovetin B Dispersing agent Dispergator HG Polyvinyl alcohol Nowinol 30/88 Color "Upper Reines Milori Blau" Kaolin

Ultrasil VN3 Synthetic Carrier Netzer IS Wetting Agent Dispersant Ultrazine Polyvinyl Alcohol Rhodoviol 14/120 Dextrin

Rhodamin BSA dye

Barley seed of GK-59 species infected with Ustilago sp. Is pickled by the test means, then sown on plots of 50 m ² with a row spacing of 12 cm and a depth of 5 cm; four plots are always sown in the same way. Exactly 150 seeds are sown in the eighth row of each plot at a length of 2 m. Phytotoxicity is evaluated at the developmental stage of two to four barley leaves by counting plants resulting from 150 seeds sown in the eighth row of 2 m and measuring the height of the increase.

- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butanol (TRIADIMENOL) in the form of mordant powder containing 40% by weight of the active substances according to Table 16 The weight ratio of the active substances is given in Table 17.

A (%) B (° / o)

40.00 - - 40.00

2,00 -

5,00 -

4,00 -

1.50 -

47,5 40,25 - 5,00 - 2,50 - 6,00 - 2,50 - 2,50 - 1,25 plants. Mold infestation is evaluated at flowering time by counting the ears affected by cereal gangrene on the plots, while also spore germination is evaluated. The results are shown in Table 17.

Table 17 shows that at a dose of 1.5 kg of active ingredient mixture per ton of seed, fungal ear infection is completely suppressed at a DBCN-Me to NUARIMOL or TRIADIMENOL ratio of 2: 1 to 14: 1 by weight.

Dose kg / t DNCB-Me + NUARIMOL Number of Raised (Piece) Medium height (cm) Number of infected ears (head) 1.00 + 0.5 117.8 8.6 0 1.25 + 0.25 113.3 8.6 0 1.40 + 0.10 114.0 . 8.5 0 1.40 - 110.3 8.2 44 1,80 - 97.5 8.0 15.3 - 0,5 114.8 8.5 3.0 - 0,7 114.5 8.5 1,8 untreated control 109.0 8.6 97.5 DNCB-Me + TRIADIMENOL 1.00 + 0.5 118.5 8.3 0 1.25 + 0.25 119.3 8.7 0 1.40 + 0.1 118.1 8.4 0 1.40 - 110.3 8.2 44 1,80 - 97.5 8.0 15.3 - 0,5 115.4 8.3 4.3 - 0,7 115.0 8.1 0.5 untreated control 109.0 8.6 97.5

Claims (5)

SUBJECT Synergistic fungicidal composition, characterized in that it contains, by weight, from 5 to 85% by weight of active substance consisting of a 3,5-dinitro-4-chlorobenzoic acid derivative of the formula I OF THE INVENTION - C — C4H9 OH (d) where is R is an alkyl group having 1 to 6 carbon atoms, and from a 1,2,4-triazole derivative represented by the general formula (IV) wherein is R 5 is a hydrogen atom, a phenyl group, a phenoxy group, an optionally substituted phenyl group or a halogen atom, or a halogen atom substituted with a benzyl group, Re is hydrogen or trifluoromethylphenyl, R 7 is a phenyl group or a group selected from the group consisting of formula (c), (dj and (e) —C — C4H9 where R is (C 1 -C 4) -alkyl, in a weight ratio of 1: 2 to 14: 1. 2. A synergistic fungicidal composition according to claim 1 comprising a compound of formula (I) wherein R is C1-C4alkyl, especially methyl or ethyl. 3. A synergistic fungicidal composition according to claim 1, wherein the compound of formula (IV) wherein R5 is hydrogen, phenyl or phenoxy optionally substituted by phenyl or chlorine or benzyl is substituted by one or two chlorine atoms. 4. A synergistic fungicidal composition according to claim 1 comprising a compound of formula (IV) wherein R7 is a group of formula (e) wherein R6 is ethyl or propyl. 5. A synergistic fungicidal composition according to claim 1 comprising a compound of formula I wherein R is as defined in point 1 and a compound of formula IV wherein the individual symbols are as defined in point 1 in a weight ratio of 1: 3 to 14: 1.