DD299034A5 - MEANS FOR CONTROLLING PHYTOPATHOGENOUS MUSHROOMS - Google Patents

Abstract

The invention relates to compositions for combating phytopathogenic fungi containing as active ingredient Salicylsaeureanilid copper complexes gemaesz formula I in addition to the usual Traegerstoffen, Verduennungsmitteln and / or surface-active substances. The compositions according to the invention have fungicidal activity against a broad spectrum of phytopathogenic fungi, such as e.g. Phytophthora infestans, Phytophthora cactorum, Botrytis cinerea, Aspergillus niger, Venturia inaequalis and are in good plant compatibility especially for the control of Phytophthora infestans on tomato and potato suitable {fungicidal agent; Salicylsaeureanilid-copper complexes; Phytophthora infestans; Tomato; Potato; Formulation auxiliaries; Kulturpflanzenvertraeglichkeit}

Description

in which R ^{1 is} hydrogen or halogen, R ^{2 is} hydrogen, halogen or a nitro group, R ³ and R ^{4 are} independently hydrogen, halogen, nitro, alkyl or halogen-substituted alkyl groups.

The active compounds according to the invention are technically readily available, have very good fungicidal activity against a broad spectrum of Dhytopathogenic fungi, such as. B. Phytophthora infestans, Phytophthora cactorum, Botrytis cinerea, Aspergillus niger and VentJria inaequalis and are surprisingly well plant tolerated in their use concentrations.

They thus represent a valuable enrichment of the prior art, in particular in the control of late blight on potato and brown rot tomato, as favored by the cell membrane-active ligand uptake of the applied copper by the plant and / or microorganisms and so Copper content of the fungicidal agent compared to the commonly used spray Cupral 45 (Kupf <rxidchlorid) is significantly reduced.

The preparation of the salicylic anilide-copper complexes can be carried out by known processes (J. prakt. Chem. 151, 145; Indian J. Chem., 13, 732-733), whereby microcrystalline powders which are insoluble in organic solvents are obtained, which are thermal until the melting range of the salicylic anilides used as ligands are stable.

The compounds according to formula I can be mixed with other known fungicides, so that a synergistic effect occur and in many cases, a broadening of the spectrum of activity against phytopathogenic fungi can be achieved.

The active compounds according to the invention are formulated with suitable carriers and / or diluents and optionally surface-active substances or other auxiliaries by known methods into dusts, wettable powders, pickling agents, granules, concentrates or pastes and applied by dusting, spraying, scattering or pouring.

The fungicidal compositions generally have an active ingredient content of 10-90% by weight, depending on the intended use. When applying the active compounds according to the invention to plants, parts of plants or on the ground by dusting, scattering, spraying or pouring, the application-technological preparations may contain 2 to 2,000 ppm of active ingredient. The following embodiments are intended to explain the invention.

example 1

Copper complex of 5-biomsalicyl-4'-chloroanilide (compound 11)

9.78 g (0.03 mol) of 5-bromosalicyl-4'-chloroanilide are suspended in 150 ml of water / methanol mixture and dissolved after addition of 2.24 g (0.04 mol) of potassium hydroxide with stirring. By adding a solution of 3 g (0.015 mol) of cupric acetate monohydrate in 150 ml of water, an olive precipitate is precipitated. After filtration with suction, washing with water and drying, 9.55 g (91% of theory) of compound 11, mp> 200X remain.

Analogously to Example 1 gives the compiled in Table 1 precursors of the general forms'. I.

Table 1 R ' R ² R ³ R ⁴ No. H H H H 1 H H H 4-CI 2 K H H 4-CH ₃ 3 H H H 4-OCH ₃ 4 H H 3-CF ₃ H 5 H H 3-NO ₂ H 6 H H 3-CI 4-CI 7 5-NO ₂ H H H 8th 5-Br H H H 9 5-Br 3-Br H H 10 5-Br H H 4-CI 11 5-Br 3-Br H 4-CI 12

Example 2

In vitro action against Botrytis cinerea

The dissolved compounds according to the invention were added to spore suspensions of the test fungus Botrytis cinerea in concentration gradations. After incubation for 20 hours in the incubation room, microscopic counting of germinated and non-germinated spores was performed. Using these results, the ED ₆₀ and ED ₉₅ values were determined.

Active ingredient Botrytis cinerea

ED ₆₀ -WeH ED _S 5 value

No. 10 2.0x1 (r ^e mol 3.6x10 ~ ⁶ mol

No. 11 1.3x1 (T ⁸ mol 2.5x1 (T ⁶ mol

Example 3

In vivo action against Botrytis cinerea on field bean egg

Full-grown leaflets cut off from plants of the field bean (Vicia faba) grown in the greenhouse were sprayed on the underside of leaves with compound no. 8 according to the invention, which had been formulated as a wettable powder. After the spray coating had dried, the leaves were inoculated with a conidia suspension of the pathogen. The leaves were incubated in humidity chambers for optimal disease development, with a control success of> 90% was achieved with only 500 ppm of the compound of the invention No. 8.

Example 4

In vivo action against Phytophthora infestans on tomato plants under glass The substances formulated as wettable powders with 20% active ingredient were sprayed onto approximately 10 cm large tomato plants. After the spray coating had dried on, the plants were inoculated with a zoospore suspension of the pathogen. The plants were incubated under favorable conditions for disease development. In the course of the disease symptom development, the control success shown in Table 2 was scored.

Table 2

Control of Phytophthora infestans on tomato plants under glass

active substance Application rate Ad for Cu content mind.95% action Deras (%) untreated 100% infestation _ Spray-Cupral45 500 ppm 55.25 number 1 150 ppm 13.02 No. 2 100 ppm 11.41 No. 7 100 ppm 10.15 No. 9 50 ppm 9.83 No. 11 50 ppm 8.89

From Table 2 it can be seen that the compositions of the invention have a better action against Phytophthora infestans and at the same time a saving of valuable copper is achieved.

Claims (1)

Claim: 1. A composition for controlling phytophatogenic fungi on agricultural and horticultural crops, characterized in that it contains as active ingredient Salicylsäureanilid copper complexes of the general formula I, (I) in which R ^{1 is} hydrogen or halogen, R ^{2 is} hydrogen, halogen or a nitro group, R ³ and R ⁴ independently of one another are hydrogen, halogen, nitro, alkyl or halogen-substituted alkyl groups, in addition to the customary auxiliaries and carriers. 2. Composition according to claim 1, characterized in that they are suitable for controlling Oomycetes, in particular of Phytophthora infestans on potato and tomato. Field of application of the invention The invention relates to novel fungicidal compositions for controlling phytophathogenic fungi, in particular üomyceten on agricultural and horticultural crops containing as active ingredient organic copper complexes. Characteristic of the known technical solutions Inorganic copper compounds are used in fruit, wine, potato and tomato growing on a large scale for controlling phytopathogenic fungi. Copper-lime broth, malachite, copper (I) oxide and copper oxide chloride are known as protective foliar fungicides. However, the copper content of these preparations is unacceptably high at 50-60%. Other disadvantages include inadequate plant compatibility at practical application rates. Organic copper compounds are also used for foliar spraying and as wood preservatives, in particular fatty acid salts and copper 8-hydroxyquinolate. Although these generally have a lower toxicity and usually better plant compatibility than the inorganic copper salts, they do not satisfy their application safety and residue behavior. It is also customary to use N-Arv'-carboxamides to combat Oomycetes on crops. These known highly effective preparations, such as. As metalaxyl, are only limited use because of the increasing η resistance phenomena. Also known is the antifungal, bactericidal and fungicidal action of numerous salicylic acid derivatives. Copper, nickel, cobalt and iron complexes of salicylic anilide are claimed as auxiliaries for waterproofing and decaying textiles (Ind. P. 66794 and 66795) and for the protection of wood, straw, bamboo and similar cellulosic materials (Ind. P. 83567 ). Their application to control phytopathogenic fungi on agricultural and horticultural crops, especially of Oomycetes, was countered by phytotoxic concerns. Object of the invention The aim of the invention is to provide new fungicidal agents for use in agricultural and horticultural crops, which are improved in their economy, application safety and their residue behavior compared to previously common preparations that do not have the disadvantages mentioned above and are characterized in particular by a reduced copper content. Explanation of the nature and feature *) of the invention The invention is based on the object by the choice of suitable ligands the Kupferkoni plex s d to gestaltan that the desired, improved performance characteristics can be achieved. The object is achieved according to the invention in that salicylic anilide complexes of the general formula I are used as active substances in fungicidal agents.