NO151389B - REMOTE RECEIVER WITH AUTOMATIC TRIM SYSTEM - Google Patents

Description

Means for combating fungi, especially powdery mildew.

The invention relates to new agents that can be used to combat fungi, especially powdery mildew.

From the French patent no. 1 209 177 compounds with the formula are known, among other things

wherein R can be a short-chain unbranched halogen-substituted alkyl group. It is said that this compound has pesticide, especially acaricidal or insecticidal action. It has now been found that the compounds 2,4-dinitro-6-(2-octyl)-phenyl-α-chlorobutyrate and/or 2,4-dinitro-6-(2-octyl)-phenyl-γ-chloro -butyrate has a particularly strong fungicidal effect. This effect, which is not mentioned in the said patent for the compounds described there, is stronger than the fungicidal effect of the compounds described in the said patent. In addition, the agents according to the invention have a very low phytotoxicity.

The agents according to the invention are characterized in that they contain 2,4-dinitro-6-(2-octyl)-phenyl-α-chlorobutyrate and/or 2,4-dinitro-6-(2-octyl)-f enyl-γ-chlorobutyrate.

The active substances can be prepared in ways that are known or equivalent for such compounds, e.g. by reacting the corresponding phenols or phenolates with a chlorobutyric acid or chlorobutyric acid halide or a chlorobutyric acid ester.

The production preferably takes place with

that a suitable dinitroalkylphenol is allowed to react with a suitable chlorobutyric acid chloride in the presence of a hydrogen chloride binding agent. A tertiary nitrogen base is preferably used as a hydrogen chloride binder, e.g. pyridine, dimethylaniline, dimethylamine, lutidine and especially collidine.

Example 1.

To a solution of 11.50 g of sodium

148 g of 2,4-di-nitro-6-(2-octyl)-phenol was added to 250 g of methanol in 200 ems of methanol. After brief stirring, the methanol was distilled off, leaving behind an excess of the sodium compound of 2,4-dinitro-6-(2-octyl)-phenol.

This was dissolved in 300 ems of acetonitrile

and added to a solution of 75 g of α-chlorobutyryl chloride in 100 g of acetonitrile. After 45 min. with continuous stirring, the sodium chloride formed was filtered off and the acetonitrile was distilled off from the filtrate. The excess thus formed was dissolved in 700 cm:<1>' of benzene and the resulting solution washed successively with water, dilute hydrochloric acid (2n.), water, a 10 per cent sodium carbonate solution and finally with water, until a neutral reaction had been achieved.

After the benzolic solution drying over anhydrous sodium sulfate, the benzene was distilled off and a yellow oil consisting of technically pure 2,4-dinitro-6-(2-octyl)-phenyl-α-chlorobutyrate appeared as a residue.

The compounds used as active substances according to the invention, namely 2,4-dinitro-6-(2-octyl)-phenyl-α-chlorobutyrate and 2,4-dinitro-6-(2-octyl)-phenyl-Y- chlorine butyrate is distinguished by a good fungicidal effect and especially by a particularly good effect against powdery mildew, especially against apple powdery mildew. Thereby, these compounds are suitable for use in agents for combating mold and especially powdery mildew, especially on apples, among other things because these compounds do not or only to a small extent attack the plants, and they are not or hardly phytotoxic.

An agent according to the invention can be prepared according to a known or equivalent method for the production of such an agent and, e.g. according to the methods specified below.

The fight against mold on plants can be carried out in a known way, e.g. in that an agent according to the invention is applied to the objects to be treated by spraying or spraying.

The preparation of an agent according to the invention can take place by mixing an active substance with an inert solid or liquid carrier, if desired using a surfactant, dispersion or adhesive.

An atomizing powder can, e.g. is produced by grinding two parts by weight of active substance, 10 parts by weight of chalk and 88 parts by weight of dolomite together, e.g. to an average particle size of approx. 10 microns has been reached.

A spray powder can e.g. is produced by mixing and grinding 20 parts by weight of active substance, 75 parts by weight of kaolin, 2 parts by weight of oleylamido-methyl taurate and 3 parts by weight of sodium lignin sulphate, until an average particle size of approx. 10 microns.

A mixed oil can e.g. is prepared by mixing 7 parts by weight of active substance, 50 parts by weight of acetone, 15 parts by weight of methyl ethyl ketone, 23 parts by weight of xylol and 5 parts by weight of a polyoxyethylene sorbitan fatty acid ester. An emulsion is produced by mixing a miscible oil with water.

A seed disinfectant can e.g. is produced by mixing 5 parts by weight of active substance with 93 parts by weight of kaolin and 2 parts by weight of an adhesive, e.g. spin part oil.

For the production of the aforementioned pul-

it is also possible to use other inert carriers, e.g. lime and pipe clay, for the production of miscible oils other inert diluents can be used, e.g. toluene and cyclohexanone. It is also possible to use other surfactants than the ones mentioned.

In order to demonstrate the fungicidal effect of the compounds, the following experiments were carried out:

Example 2.

Ten small apple plants (4-6 leaves) were showered to runoff with an aqueous suspension (10-3.5 g/ml) of 2,4-dinitro-6-(2-octyl)phenyl-α-chlorobutyrate. After drying, the plants were infected with dry spores of Podosfera laucotrica harvested from heavily infested plants. A comparison group formed by ten apple seedlings was showered with water, dried and infected in the same way.

After treatment, the plants are grown further in a glass house at 18-20°C for 14 days. The third and fourth leaves of each plant were examined for powdery mildew infection on a scale from 0 = no infection to 5 = leaf completely covered by mycelium. The numbers obtained from ten plants were added and expressed as a percentage of the obtained sum of untreated plants. A reduction in the powdery mildew infection of 83 per cent was achieved.

In a similar experiment in which the plants are treated with a suspension of 10-4.5 g/ml, a reduction of 62 percent was achieved.

Example 3.

In an experiment corresponding to example 2, a reduction of 93 percent was achieved.

in powdery mildew attack with 2,4-dinitro-6-(2-octyl)phenyl-γ-chlorobutyrate.

Example 4.

Groups of small apple plants (6 plants) were showered with a 0.03 percent resp. 0.1% and 0.3% solution in acetone of 2,4-dinitro-6-(2-octyl)-α-chlorobutyrate. After the treatment, the plants were grown further in a greenhouse, 15 days after the treatment, the toxicity of the substance for the leaves was adjusted on a scale between 0-6.

0 = no damage 1 = very lightly attacked

2 = lightly attacked

3 = clearly attacked

4 = moderately strongly attacked

5 = heavily attacked 6 = plants dead.

In all three concentrations, no damage was observed.

In a similar experiment with 2,4-dinitro-6-(2-octyl)phenyl-γ-chlorobutyrate at 0.03% the assessment was 0. At 0.1% and 0.3% the assessment was 1, resp. . 1. With 2,4-dinitro-6-sec. butylphenyl)-α-chlorobutyrate at 0.03 percent was rated 0, and at 0.1 percent the rating was 2.

Example 5.

An experiment, similar to that described under example 4, was carried out with 1-week-old plants of Phaseolus vulgaris. The evaluation of the leaf toxicity was done in the same way as described in example 5. For 2,4-dinitro-6-(2-octyl)phenyl-a-chlorobutyrate sprayed with 0.03 percent resp. 0.1% acetone solution was rated 1, resp. 1. For 2,4-dinitro-6-(2-octyl)phenyl-γ-chlorobutyrate sprayed with a 0.03 percent resp. 0.1 percent acetone solution was rated 0, resp. 0.

Example 6.

In a greenhouse trial, three blocks of a total of 32 plants of the cucumber variety Sporu were sprayed to runoff (5 1 of the emulsion/32 plants) 2 times at intervals of 10 days with 0.03 percent emulsion in water of a 75 percent .emulsifiable oil of 2,4-dinitro-6-(2-octyl)phenyl-α-chlorobutyrate. At the time of treatment, the plants had reached a length of 1.5-2 m. The infection assessment with cucumber powdery mildew was carried out 10 days after other treatment in the following way: The number of heavily infected leaves was multiplied by 2, and the number of lightly infected leaves were taken as such. The sum of these numbers for treated cucumber plants was 15. For the same number of untreated plants, the number was 174.

Build mildew contact test.

Young barley plants (Hordeum vulgare cultivar Balder) were sprayed with a 0.01% solution or suspension of the compound to be investigated. After drying, the plate was infected with spores of Erysiphe graminis. The plants were stored for 6 days at a relative humidity of 90 per cent, 22°C and under constant lighting. The Muggan grip is expressed as a percentage of blank.

Apple powdery mildew test.

Young apple cuttings were similarly treated with Podosphaera leucotricha after spraying them with a 0.03% solution of the compound to be examined.

From the results, it appears that the agents according to the invention have a much greater protective effect against mold attack than the corresponding secondary butyl compounds, which are covered by the French patent no. 1 209 177.

Claims (1)

Means for combating fungi, especially powdery mildew, characterized in that it contains as active substance 2,4-dinitro-6-(2-octyl)-phenyl-a-chlorobutyrate and/or 2,4-dinitro-6-( 2-octyl)-phenyl-γ-chloro-butyrate.