DE2922292A1 - Fungicides esp. seed dressings - contg. a furan-3-carboxamide and allyloxy-di:chloro-phenethyl-imidazole and/or 2-thiazolyl-benzimidazole - Google Patents

Abstract

New fungicidal agents contain (a) a furan-3-carboxamide (I) and (b) 1-(beta-allyloxy-2,4-dichlorophenethyl) imidazole (II) and/or 2-(4-thiazolyl)-1H-benzimidazole (III). In the formula (I), R is H, alkyl, acyl, aroyl, or sulphenyl and R' is H, alkyl, alkenyl, cycloalkyl, naphthyl, benzyl, pyridyl, thiazolyl, ethylenebis, furylmethyl or opt. substd. phenyl or NRR' is a heterocyclic ring; and X, Y and Z are H, NH2, opt. substd. alkyl, halo, alkenyl, or opt. substd. phenyl, or Y and Z together are alkylene). The use of such cpds. as fungicides is known. Component (b) extends the spectrum of (I), so that the combinations have a wider spectrum of activity and greater fungicidal activity than mercurial fungicides usually used as need dressings, and their toxicity to warm-blooded animals is lower. Pref. cpds. (I) are 2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide and 2,4,5-trimethylfuran-3-carboxanilide.

Description

Fungicidal agent

The invention relates to fungicidal or fungicidal agents, which contain a furan-3-carboxamide.

For example, the use of ituran-3-carboxamides as fungicides is out U.S. Patents 3,939,481, 4,054,585, 3,903,293 and 3,862,966. Other Garboxamides are known from British patent specification 1,215,066. These compounds While effective for many uses, they are not against all forms of fungi that attack seeds effectively. To combat plant diseases causing fungi on seeds or seeds (e.g.

the mushroom species Calonectria nivalis, Pyrenophora graminea, Tilletia caries, Ustilago avenae, Septoria nodorum, Tilletia foetida, Ustilago hordei, Ustilago nigra, Urocystis occulata, Pyrenophora -avenae, Gochliobolus sativus) are mainly Mercury-containing materials are used. However, these materials have the disadvantage toxicity to warm-blooded animals. Other, less toxic materials are because of theirs narrow spectrum of activity unsatisfactory.

The object of the invention are therefore fungicides, in particular for treating seeds that are less toxic and have a broader spectrum of activity have known as fungicides.

The invention is a fungicidal agent in which a Furan-3-carboxamide (I) is included, characterized in that the agent also I-Cjj- (Allyl oxi) -2,4-dichlorophenethylI-imidazole (II) (11) and / or 2- (4-thiazolyl) -1-H-benzimidazole (III) contains.

The agent according to the invention can contain other ingredients, e.g. carriers, Diluents, solvents, dyes, insecticides and / or repellants or contain protective agents with a repellent effect.

According to the invention, the term “furan-3-carboxamide” includes compounds with the structural formula to understand where R is hydrogen, ethyl or another alkyl, acyl, aroyl (e.g. benzoyl) or sulfenyl (e.g. trichloromethylsulfenyl) and R 'is hydrogen, alkyl, alkenyl, cycloalkyl, naphthyl, benzyl, pyridyl, thiazolyl, ethylenebis-, furylmethyl , Is phenyl or substituted phenyl.

The phenyl substitution can be selected from alkyl, alkoxy, nitro, halogen, Carboxy or phenyl groups such as biphenyl exist. R and R can be formed linked by heterocyclic groups such as the morpholino and other ring structures be. X, Y and Z can, independently of one another, be selected from hydrogen, NH2-, alkyl, substituted Alkyl (e.g. hydroxyalkyl, chloroalkyl, nitroalkyl), halos, alkenyl (e.g. allyl), Phenyl and substituted phenyl (e.g. alkylphenyl, halophenyl, Alkoxyphenyl), and Y and Z can together be a «W-alkylenes (e.g. Tetramethylene).

The preferred furan-3-carboxamides are the carboxanilides, in particular the carboxanilides in which X is methyl and Y and X, independently of one another, from H and methyl are selected, e.g., 2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide or 2,4,5-trimethylfuran-3-carboxanilide.

A composition according to the invention can be used as a fungicide and is of particular use when applied to seeds. By inventive A dressing agent for seeds is provided in this way, which is a broad spectrum of activity together with increased or synergistic activity against certain fungi.

A means according to the invention in the form of a dressing agent for seeds is less toxic than the mercury-based pickling agents, and it's whether in shape of a seed dressing agent with multiple uses (combination of compound I and II or of compounds I and III) or in the form of a universal pickling agent for seeds (combination of compounds I, II and III) for use in the Suitable for agriculture, horticulture and forestry.

An agent according to the invention can be used together with one or more additional pesticides such as insecticides (e.g. organochlorine compounds such as lindane, organophosphoric acid esters such as diazinon, isazofos and thiofanox and carbamates such as carbofuran, mercaptodimethur and bendiocarb) and repellants (e.g. anthraquinone, thioanthraquinone, benzanthrone, ziram and diphenylguanidine) are used to protect the seeds from pests such as insects and birds.

In comparison with known universal pickling agents containing mercury For seeds, the agents according to the invention have a further spectrum of activity (for example they are suitable for combating Ustilago nuda, Ustilago tritici, Typhula incarnata, Rhynchosporium secalis, Erysiphe graminis) and a higher degree of effectiveness against other seed-Afank pathogens (e.g. Pyrenophora avenae, Cochliobolus sativus).

The compounds I, II and III are known from US Pat. No. 3,959,481, DE-OS 20 63 857 or from Phytopath.

Z. 48, 29-72, 1965. The agent according to the invention can be one or more Carrier materials such as the minerals talc, kaolin, ecntonite and barite and adhesives such as spindle oil, ethylene glycol and polyvinyl acetate. The medium can contain pigments such as iron oxide and ruby red toners.

An agent according to the invention in the form of a powder can be formulated by including all dry materials, the carrier and the additives, mixed together until a homogeneous mixture is formed. Then will The adhesive is added, and the whole thing is mixed again until the mixture is mixed has become homogeneous.

In the case of a liquid formulation, organic solvents are used such as xylene, dimethylformamide, ethylene glycol and methanol and cyclohexane as diluents used and with surface-active agents (calcium dodecylbenzenesulfonate, polyglylçolether and aryl polyether alcohols) and a dye (e.g. rhodamine and methyl violet) are mixed together. The compounds I and III are mixed with the solvent and other additives mixed until all materials are dissolved and become a clear liquid will. Then the compound II, if used, is mixed in until a homogeneous Mixture has formed. Then more solvent is added until the desired one Total volume is reached. If necessary, the mixture obtained is filtered.

A preferred, inventive agent contains 0.3 to 30% of the Compound I, 0.5 to 10% of compound II and 0.3 to 15% of compound III. Particularly preferred is an agent that contains 2 to 15, 0 of the compound I, 2 to 5% of compound II and 2 to 10 ^ t. the compound III contains.

The agent according to the invention is preferably used in such an amount Applied to seeds that the active compounds in the following narrow in the per 100 kg of seed applied agent are present: Compound I: 1 to 60 g of active Ingredients Compound II: 1 to 20 g of active ingredients Compound III: 1 to 30 g of active ingredients.

The following amounts are particularly preferred: Compound I: 4 to 30 g active ingredient compound II: 3 to 15 g active ingredient compound III: 3 to 20 g of active ingredients.

Agents according to the invention can be used, for example, for the seeds of rye, Wheat, barley and oats can be used.

The Irfindung also refers to a procedure for the protection of Seed against fungi, which consists in that one according to the invention is applied to the seed Raises funds.

The invention is illustrated in more detail by the following examples. In these examples, the particular seed was grown in accordance with the procedure treated as it is in the BRA guidelines 4-1.1 (March 1974): Ehle, H., Frohbeyer, P.-E., Reinhard, H. and Röder, K. (1974) s Preliminary Guidelines for the Test of Seed dressings against cereal diseases ", March 1974, published by BBA, Messeweg 11/12, 3300 Braunschweig.

In all examples, the compound I was 2,4,5-trimethylfuran-3-carboxanilide used.

Example 1 Effectiveness against snow mold on rye (Calonectria nivalis) Naturally infested rye seed was grown in the greenhouse with the in table 1 (200 g seed dressing / 100 kg seed) and in Garden soil planted in wooden boxes. The extent of the infection was determined using the Occurrence of the fungi found in the untreated comparison sample, and the Disinfectant effectiveness was evaluated repeatedly.

Table 1 Preparation Relative extent of infection (%) 1 a Powdery Seed dressing I (15%) + II (2.5%) + III (2.5) + carrier, additives and 10.7 Colorants (80%) 1b Liquid seed dressing I (15%) + II (2.5%) + III (2.5%) + Solvents, additives 16.3 and dyes (80 Có) Fuberidazole + Quintozen (3%) + (25, ¢ 9) + carriers, additives and dyes - 44.2 substances (72%) Untreated comparison sample 100.0 The results were confirmed under outdoor conditions.

Example 2 Efficacy against stink or smear brandy on wheat (Tilletia caries) Wheat seeds inoculated with spores were treated (200 g seed dressing / 100 kg of seeds) and planted outdoors. Before the harvest, those with stink or Smear attacked ears of corn were counted. The results are given in Table 2.

Table 2 Preparation Relative Degree of Infection (%) 1 a Powdered Seed dressing I (15%) + Ii (2.5%) + III (2.3%) + carrier, additives and 0.00 Colorants (80%) ib Liquid seed dressing 1 (15%) + II (2.5%) + III (2.5%) + Solvents, additives and dyes (80%,) 0.00 methoxyethylmercury silicate (4.3%) + carriers, additives and colorants (95.5%) 0.49 Untreated comparative sample 100.00 The preparations 1a and Ib led to a simultaneous control of Airborne or dust fire (Ustilago tritici) on the wheat.

Example 3 Efficacy against airborne scorch or dust scorch on oats (Ustilago avenae) oat seeds obtained by the Zade infiltration process (improved by Thiede 1963) was treated (200 g seed dressing / 100 kg of seeds) and planted outdoors. Before the harvest, the affected panicles were counted.

The results are given in Table 3.

Preparation Table 3 Relative extent of infection (%) 1 a powdery Seed dressing I (15%) + II (2.5%) + III (2s5%) + carrier, additives and coloring agent (80%) 0.00 1b Liquid seed dressing I (15%) + II (2.5%) + III (2.5%) + solvent, Additives and color (80%) 0.00 Untreated comparative sample 100.00 example 4 Effectiveness against airborne or dust fire on barley (Ustilago nuda) Naturally infected Barley seed was treated (200 g seed dressing / 100 kg seed) and outdoors planted out. Before the harvest, the infested currency was paid.

The results are given in Table 4.

Table 4 Preparation Relative extent of infection (%) 1 a powdery Seed dressing I (15%) + II (2.5%) + III (2.50 + carrier, additives and coloring agent (80%) 1.30 1b Liquid seed dressing I (15eo) + II (2.5%) + III (2.3%) + solvent, Additives and color (80%) 1.10 carboxin (48%) + nethoxyethyl mercury silicate (3.4M0) + carrier, additives and coloring agent (48.6 20) 2.30 methoxyethyl mercury silicate (4.5%) + Carrier, Additives and Colorant (95.5) 100.00 Example 5 Effectiveness against the streak disease on barley (Pyrenophora graminea) Naturally infested Barley seed was treated (200 g seed dressing / 100 kg seed) and outdoors planted out. The results are given in Table 5.

Table 5 Preparation Relative extent of infection (%) 1 a Powdery Seed dressing I (15%) + II (2.5%) + III (2.5%) + carrier, additives and coloring agent (80%) 0.00 1b Liquid seed dressing 1 (15%) + II (2.5%) + III (2.5) + solvent, Additives and coloring (80%) 0.90 methoxyethyl mercury silicate (4.5%) + carrier, Additives and colorants (95.5 cÓ) 3.60 Untreated comparative sample 100.00 Example 6 Synergistic effect against snow mold on rye (Calonectria nivalis) Of course Infested rye seeds were grown in the greenhouse using the values given in the table below Preparations treated and planted in garden soil in wooden boxes. The extent the infection in the untreated comparison sample was determined, and the disinfecting effect has been repeatedly stated. The results are given in Table 6.

Table 6 Preparation Number of uses Relative extent of Infection (O I 30 23.1 III 5 10> 2 (I + III) (30 + 5) 0.1 Untreated comparison sample 100.00 Example 7 Effectiveness against airborne or dust burn on barley (Ustilago nuda) Naturally Infested barley seed was treated (200 g seed dressing / 100 kg seed) and planted out in the open. Before the harvest, the infected days were counted.

The results are given in Table 7.

Table 7 Preparation Relative extent of infection (%) 1 a Powdery Seed dressing I (15%) + II (2.5%) + carrier, additives and colorants (82.3 "-) 0.00 ib Liquid seed dressing I (13%) + TI (2.5%) + solvents, additives and dyes (82.3%) 0.00 methoxyethyl mercury silicate (4.5%) + carriers, additives and dye (93.3%) 100.00 Untreated comparative 100.00 Example 8 Efficacy against the streak disease on barley (Helminthosporium graminium) naturally infected Barley seed was treated (200 g seed dressing / 100 kg seed) and outdoors planted out. The results are given in Table 8.

Table 8 Preparation Relative extent of infection (%) 1 a Powdery Seed dressing I (15%) + Ii (2.5%) + carrier, additives and coloring agent (82.5%) 0.3 1b Liquid seed dressing I (15%) + II (2.3%.) + Solvents, additives and dye (82.5%) 0.4 methoxyethyl mercury silicate, (4.5%) + carrier, additives and dye (95.5, có) 3.60. Untreated comparison sample 100.00

Claims (10)

Claims 1. Fungal agent in which a furan-3-carboxamide (I) is contained, characterized in that the agent also 1- [ß- (allyloxy) -2,4-dichlorophenethyl] imidazole (II) and / or 2- (4-thiazolyl) -l-H-benzimidazole (III) contains. 2. Means according to claim 1, characterized in that the furan-3-carboxamide is a furan-3-carboxanilide. 3. Composition according to claim 2, characterized in that the carboxanilide 2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide or 2,4,5-trimethylfuran-3-carboxanilide. is. 4. Means according to one of the preceding claims, characterized in that that it is dissolved in a solvent. 5. Agent according to one of the preceding claims, characterized in that that it is mixed with a carrier. 6. Means according to claim 5, characterized in that the carrier mineral talc, kaolin or bentonite is. 7. smock according to one of the preceding claims, characterized in that that it is 0.5 to 30% furan-3-carboxamide (I), 0.5 to 10% of the compound (II) and / or Contains 0.5 to 15% of the compound (III). 8. Means according to claim 7, characterized in that there are 2 to 10 , «Of the compound (III) contains. 9. Method for the protection of seeds against fungal diseases, thereby characterized in that one is effective in terms of fungus kill on the seed Applies amount of a fungicidal agent according to one of the preceding claims. 10. The method according to claim 9, characterized in that the fungicidal Means that are applied to the seed, the active compounds in the following Amounts per 100 kg of the seed contains: 4 to 30 g of furan-3-carboxamide (I), 3 to 15 g of the compound (II) and 3 to 20 g of the compound (III).