DD246247A1 - AGENTS WITH FUNGICIDAL EFFECT - Google Patents

Abstract

The invention relates to fungicidal compositions for the control of fungal diseases in crop plants. According to the invention, in addition to the known auxiliaries and tracer substances, they also contain copper complexes of the general formula in which R 1 is hydrogen or CSNHR and R 2 is methyl or CH 2 OCSNHR where R denotes hydrogen, halogen, isomeric forms of alkyl or alkoxy with 1 to 4 carbon atoms each. Atoms stands represent.

Description

where R * is R-

III

with R to R = hydrogen, halogen, isomeric forms of alkyl or alkoxy each having 1 to 4 C atoms,

represent.

2. Means according to item 4, characterized in that they are used together with other agrochemicals and / or agrotechnical measures.

3. Means according to item 1 and 2, characterized in that they are applied at an application rate of 0.1 to 2 "kg of active ingredient / ha.

Field of application of the invention

The invention relates to new fungicidal agents for combating fungal diseases in cultivated plant stands, preferably of phytopathogenic fungi.

Characteristic of the known technical solutions

Fungal diseases on crops represent a significant cause of income reductions. These are harmful images

mainly due to increased yields and quality improvements in plant breeding

However, these benefits are often due to a certain loss of natural resistance of the plants

overshadowed by parasites. On the other hand, experience has shown that over the years harmful fungi

known fungicides have developed resistance to a greater extent.

For these reasons, there is an urgent need for appropriate active agents for crops

are tolerable and destroy their parasites.

Known materials that have already found their way into the practice are u.a. Metal salts (manganese, zinc, manganese / zinc) of ethylenebisdithiocarbamic acid or propylenebisdithiocarbamic acid such as Maneb, Zineb, Mancozeb or Antracol;

Tetramethyl thiuram disulfide (thiuram); Acylalanines such as N-2,6-dimethylphenyl-N-methoxyacetyl-2-amino

propionic acid methyl ester (Ridomil); substituted benzimidazoles, such as. Methyl benzimidazol-2-yl carbamate (carbendazim),

1- (phenylcarbamoyl-2- (methoxycarboxamido) -benzimidazole (DD-PS 142279) or methyl 1- (butylcarbamoyl) -benzimidazol-2-yl-carbamate (benomyl); 5,6-dihydro-2-methyl-1, 4-oxathiin-3-carboxanilide (Vitavax); 1,6-dimethyl-N-alkylmorpholine

(Falimorph); Copper oxychloride.

In addition, more recently, copper complexes lactams (SU 782350) have been proposed for controlling Phytophfhora in particular.

The economic disadvantages of the known prophylactic fungicides result from the z.T. required high

Application rates, frequent treatments, insufficient rainfastness and the resulting uncertainty

biological effect, which has a negative effect on the overall economy of the treatment.

Object of the invention

The aim of the invention is to find and use fungicidal compositions for combating fungal diseases in crop plants, which are improved in their economy and in their application safety compared to previously common preparations and thus do not have the mentioned disadvantages of already known substances.

Explanation of the essence of the invention

Surprisingly, it has been found that copper complexes of the general formula

Cu / 2

in the

R _{1 is} hydrogen or -CS-NH-R 'and

R _{2 is} methyl or -CH ₂ -O-CS-NH-R '

where R 'is for R

with R ¹ to R ^lv = hydrogen, halogen, isomeric forms of alkyl or alkoxy each having 1 to 4 C atoms,

have fungicidal properties, in particular for controlling Phytophthora have.

Table 1 gives an overview of some compounds covered by the general formula which fulfill these properties.

Table 1

Selection of some copper complexes of special amino acid derivatives of the agents according to the invention

Ri according to the invention. R ₂

Connection.

^{1 H} -CH ₀ Oa-HHC ^ Hf-

d. b ρ

: S

Ii -CSNHC ₆ H ₅ -CH ₂ OC-MHC ₆ H ₅ ,

III -CSNHC ₆ H ₅ -CH ₃

The application of the agents according to the invention is carried out in the preparation or application forms customary for fungicides, such as solutions, emulsions, suspensions and concentrates as sprays or dusts.

These formulations are prepared in the usual manner with the addition of formulation aids such as solvents, carriers, emulsifying and dispersing agents.

The inventive compositions according to the general formula may optionally together with other agrochemicals, such as. As crop protection and pest control or soil improvers, but also be applied in conjunction with other agrotechnical measures, with application rates of preferably 2kg to 0.1 kg / ha guarantee a fiction effect.

The novel active substances contained in the agents according to the invention are prepared by reacting the corresponding amino acids in alcoholic solution with copper (II) salts to form the copper complex and subsequently forming the thiocarbamoyl compound by adding isothiocyanates in alcoholic solution.

To prepare the serine-phenyl-copper complex (compound I, Table 1), 0.05 mol of serine are dissolved with 1 mol of sodium bicarbonate in 20 ml of water, then 0.0275 mol of copper (II) sulfate in 4 ml of water, and 30 stirred for a few minutes. To the resulting deep blue serine-copper complex is allowed at room temperature with stirring 7 ml

Phenylisothiocyanate in 270 ml of ethanol. After completion of the reaction, the gray-blue precipitate is filtered off with suction and washed with alcohol.

The other compounds which are part of the compositions according to the invention (Table 1) are likewise prepared from

The following example serves to illustrate the invention without limiting it.

Embodiment.

The application is carried out by spraying the plants with an aqueous test solution which contains the active compound according to the invention in concentrations of from 0.0025 to 0.1% by weight after the spray coating has dried on The treated, cut leaves are placed in moist chambers and infected with a zoospore suspension of Phytophthora infestans.

100 infections are set per examiner. The test material is stored for 4 days at 22 ° C to 25 ° C. On the 3rd and 4th day the infections which appear as necrotic areas (lesions) are counted.

The results are shown in Table 2. ''

Table 2

Test results after application of the agents according to the invention infestation in% compounds conc. In wt .-%

0.0025 0.005 0.01 0.05 0.1

Zineb 67 52 12 - I D shape 9 0 0 0 ii 40 12 4 2 1 III 25 1 1 0 0 I L shape 44 5 0 0 0

The results clearly reflect the fungicidal effect improved compared to the commercialized product Zineb, which is very good even at very low application rates.

Claims (1)

Invention claim: 1. Miticidal action, preferably for controlling phytopathogenic fungi, characterized in that it comprises, in addition to known excipients and carriers as the active ingredient at least one compound of the general formula included in the R _{1 is} hydrogen or -CS-NH-R 'and R _{2 is} methyl or -CH ₂ -O-CS-NH-R '