DE2130675C2 - 2,4-dichloro-6-anilino-1,3,5-benzotrinitriles and their use as biocides - Google Patents

Description

CN

in which R is hydrogen, chlorine, bromine, fluorine, an alkyl radical or alkoxy radical with 1 to 4 carbon atoms, -CF ₃ , - NH2 or the hydroxyl group and X is hydrogen, chlorine or fluorine, -CH ₃ or -OCH ₃
2.2,4-dichloro-6- (anilino) -trimesonitrile 3.2,4-dichloro-6- (o-chloroanilino) -trimesonitrile.

4.2,4-dichloro-6- (p-hydroxyanilino) trimesonitrile.

nitrile.

6.2,4-dichloro-6- (o-bromanilino) -trimesonitrile.

7.2,4-dichloro-6- (2,3-dichloroanilino) trimesonitrile.

8.2,4-dichloro-6- (o-hydroxyanilino) trimesonitrile.

9.2,4-dichloro-6- (m-chloroaniIino) -trimesonitrile.

10.2,4-dichloro-6- (3-chloro-2-methylanilino) -trimesonitrile.

11.2,4-dichloro-6- (3-fluoroanilino) trimesonitrile.

12.2,4-dichloro-6- (2,4-difluoroanilino) -trimesonitrile.

13.2,4-dichloro-6- (o-ethylanilino) -trimesonitrile.

14.2,4-dichloro-6- (3,4-dichloroanilino) trimesonitrile.

15. Use of 2,4-dichloro-6-anilino-1,3,5-benzotrinitrile according to claim 1 as biocides.

15th

20th

25th

jo

35

40 2,4-dichloro-6- (anilino) -trimesonitrile,
■ ^ -Dichlor-e- ^ o-chloranilinoJ-trimeso-

nitrile,
2,4-dichloro-6- (p-bromanilino) -trimeso-

nitrile,
2,4-dichloro-6- (p-hydroxyanilino) -trimeso-

nitrile,
2,4-dichloro-6- (p-aminoanilino) -trimeso-

nitrile, '
2,4-dichloro-6- (2,4-dimethylanilino) -

trimesonitrile,
2,4-dichloro-6- (3,4-dimethoxyaniiino) -

trimesonitrile,
2,4-dichloro-6- (o-bromanilino) -trimeso-

nitrile,
2,4-dichloro-6- (23-dimethylanilino) -

trimesonitrile,
2,4-dichloro-6- (2,3-dichloroanilino) -

trimesonitrile,
2,4-dichloro-6- (o-hydroxyanilino) -

trimesonitrile,
2,4-dichloro-6- (m-chloroanilino) -

trimesonitrile,
2,4-dichloro-6- (p-chloroanilino) -trimeso-

nitrile,
2,4-dichloro-6- (2,4-difluoroanilino) -

trimesonitrile,

2,4-dichloro-6- (o-ethylanilino) -trimesonitrii,
2,4-dichloro-6- (3-chloro-2-methylanilino) -

trimesonitrile,
2,4-dichloro-6- (3-fluoroanilino) -trimeso-

nitrile,
2,4-dichloro-6- (3-trifluoromethylanilino) -

trimesonitrile and
2,4-dichloro-6- (3,4, -dichloroanilino) -

trimesonitrile.

The present compounds are made by the usual reaction of 2,4,6-trichloro-1,3,5-benzotrinitrile with an aminobenzene of the general formula II

NH

45

Halogen-substituted benzonitriles and their biocidal properties are known; see German interpretative publications 11 99 756.14 43 731 and 19 15 799.

The invention relates to new 2,4-dichloro-6-anilino-1,3,5-benzotrinitrile of the general formula I.

55

CN

in which R is hydrogen, chlorine, bromine, fluorine, an alkyl radical or alkoxy radical with 1 to 4 carbon atoms, -CF ₃ , - NH2 or the hydroxyl group and X is hydrogen, chlorine or fluorine, -CH ₃ or -OCH ₃ .

The alkyl and alkoxy radicals preferably contain 1 to 2 carbon atoms.

Specific examples of compounds of the general formula I are:

(Π)

in which R and X have the preceding meaning condensed.

From the German Auslegeschrift 11 99 756 it is known that the chlorine atoms of 2,4,6-trichloro-1,3,5-benzotrinitrile can be exchanged for fluorine atoms. For this purpose, the 2,4,6-trichloro-1,3,5-benzotrinitril by at 175-350 ⁰ C, preferably 200 to 33O ⁰ C, heated layer from potassium, cesium or rubidium sublimated.

According to the present process, it is possible, under surprisingly mild conditions, to selectively exchange the chlorine atom in the 6-position for an aniline residue. The present process is preferably carried out in a countercurrent to the reactants an inert organic solvent at temperatures of about 0 to 100 ⁰ C. The reaction can be carried out with equimolar amounts of 2,4,6-trichloro-1,3,5-benzotrinitrile and the aminobenzene. However, the aminobenzene is preferably used in excess.

The invention also relates to the use of the 2,4-dichloro-6-anilino-13,5-benzotrinitrile of the general type Formula I as a biocide. In particular, the compounds have fungicidal, viricidal and bactericidal properties. The compounds of the invention can be used in undiluted form on plants or otherwise apply protective material. However, they are often used together with solid or liquid inert ones Carriers and auxiliaries. For use as a Fungicides can be the compounds of the invention z. B. in the form of a dispersion in an aqueous or Spray organic solvent on the plants. To protect wood, the connections in The form of a solution or dispersion can be painted on or sprayed on. You can also put the wood in the Immerse solution or dispersion. The choice of the appropriate solvent depends on, among other things the desired concentration of the active ingredient, the required volatility of the solvent, the The cost of the solvent and the type of material treated. Examples of suitable organic Solvents that can be used as carriers for the compounds of the invention are hydrocarbons, such as benzene, toluene, xylene, kerosene, diesel oil, heating oil and petroleum naphtha, ketones such as acetone, Methyl ethyl ketone and cyclohexanone, chlorinated hydrocarbons such as carbon tetrachloride, chloroform, Trichlorethylene and perchlorethylene, carboxylic acid esters such as ethyl acetate, allyl acetate and butyl acetate, the Monoalkyl ethers of ethylene glycol and diethylene glycol z. B. the monomethyl or monoethyl ether, as well Alcohols such as ethanol, isopropanol and amyl alcohol.

The compounds of the invention can be used together with inert solid excipients or carriers, such as Talc, pyrophyllite, attapulgii, kieselguhr, chalk, diatomaceous earth, calcium oxide, calcium carbonate, bentonite, Fuller's earth, cottonseed husks, wheat flour, soybean flour, pumice stone, tripoli, sawdust, walnut shell flour or lignin, can be applied to plants and other materials.

It is often desirable to incorporate a wetting agent into the biocidal agents. These wetting agents are preferably both solid and liquid pesticidal agents are incorporated. The wetting agent can be a be anionic, cationic or nonionic wetting agent.

Typical wetting agents are alkyl phonates, alkyl aryl sulfonates, alkyl sulfates, alkyl amide sulfonates, alkyl aryl polyether alcohols, Fatty acid esters of polyhydric alcohols, ethylene oxide adducts of these esters, addition products of ethylene oxide with long-chain mercaptans, Sodium alkylbenzenesulfonates with 14 to 18 carbon atoms, addition products of ethylene oxide Alkylphenols, e.g. B. p-Isooctylphenol condensed with 10 ethylene oxide units, and pages such as sodium stearate and sodium oleate.

The solid and liquid pesticides can be prepared by conventional methods. So can use the active ingredients in finely divided solid form together with a finely divided solid carrier in be mixed in a tumble mixer. Solutions, dispersions, emulsions or suspensions of the Active ingredients can be mixed with a finely divided solid carrier in such amounts that the finished dusts have free-flowing properties.

When using solid preparations, these should be in as finely divided form as possible in order to be able to deal with a Minimum amount of the preparation to be able to treat as large an area as possible. The dust should usually have such a particle size that they have a sieve with an internal size of 0.83 mm happen. Dusts that pass through a sieve with a mesh size of 0.074 mm also result satisfactory results.

Dusts contain the active ingredient preferably in amounts of 5 to 10 percent by weight, based on the

In total weight concentrations outside this range are also suitable. There are pesticides Agents with an active ingredient content of 1 to 99 percent by weight are considered. The remainder can consist of Carriers and / or other additives or

is auxiliary materials exist. The wetting agent is preferably used in an amount of 3 to 1.0 percent by weight based on the total weight of the preparation
The active ingredient can be used for the production of sprays

2 »in a liquid carrier such as water or a other suitable liquid, dissolved or dispersed. The active ingredient can also be in the form of a solution, Suspension, dispersion or emulsion in an aqueous or non-aqueous medium.

The spray compositions preferably contain 0.5 to 1.0 percent by weight of a wetting agent.

The wetting agent can be used as an auxiliary in any desired form Amount used, e.g. B. up to 250 percent by weight, lied to the active ingredient. If that Wetting agent is only used to improve the wetting properties, e.g. B. in a spray, so 0.05 percent by weight or less are sufficient. The use of larger amounts of a wetting agent does not depend on the wetting properties, but is a function of the physiological behavior of the wetting agent. This plays a special role in the treatment of plants. With liquid In preparations, the active ingredient content is often not more than 30 percent by weight, it can be 10 percent by weight or even only 0.01 percent by weight.

The compounds of the invention can be used in biocidal agents containing other known biocides, particularly fungicides, insecticides or bactericides, e.g. B. phenothiazine, pyrethrum ingredients, Rotenone or l, l, l-trichloro-2,2-bis- (4-chlorophenyl) ethane.
The examples illustrate the invention.

example 1

Production of 2,4-dichloro-6- (2-chloroanilino) -trimesonitrile

A solution of 6.45 g (0.025 mol) of trichlorotrimesonitrile (= 2,4,6-trichloro-1,3,5-cyanobenzene) in dimethyl sulfoxide is mixed with a solution of 7.05 g (0.055 mol) of o-chloroaniline at room temperature added in dimethyl sulfoxide. After the addition has ended, the mixture is ^{heated to 70 °} C. for 3 hours and stirred. Analysis of the reaction mixture by thin layer chromatography showed that the reaction has ended. The mixture is diluted with about 3 parts by volume of water. The separated yellow crystals are filtered off and dried. Yield 5.3g. After recrystallization from benzene, 4.3 g of the specified compound with a melting point of 193.5 to 194.5 ° C. are obtained.

Table I shows further compounds which are obtained according to Example 1.

Table I.

Example starting compounds end product

F., ° C

2 trichlorotrimesonitrile and 2,4-dimethylaniline

3 trichlorotrimesonitrile and 2-bromoaniline

4 trichlorotrimesonitrile and 2,3-dimethylaniline

5 Trichlorotrimesonitrile and 2,3-DichloraniIin

6 trichlorotrimesonitrile and 2-hydroxyaniline

7 trichlorotrimesonitrile and 2,4-difluoroaniline

8 trichlorotrimesonitrile and 2-ethylaniline

9 trichlorotrimesonitrile and 3-chloro-2-raethylaniline 2,4-dichloro-6- (2,4-dimethylaniIino) -trimesonitnl

2,4-dichloro-6 - (2-bromoanino) trimesonitrile

2,4-dichloro-6- (2,3-dimethylanilino) trimesonitrile

2,4-dichloro-6- (2,3-dichloroanilino) trimesonitrile

2,4-dichloro-6- (2-hydroxyanilino) trimesonitrile

2,4-dichloro-6- (2,4-difluoroanilino) trimesonitrile

2,4-dichloro-6- (2-ethylanilino) trimesonitrile

2,4-dichloro-6- (3-chloro-2-methylanilino> 217-220 trimesonitrile

217-219

196.5-197.5

233-234

211-214

250-251.5

237-238

190-193

Example 10

Production of 2,4-dichloro-6- (4-hydroxyanilino) -trimesonitrile

A solution of 12.9 g (0.05 mol) of trichlorotrimesonitrile in acetone is at room temperature with a Solution of 11.9 g (0.11 mol) of 4-hydroxyaniline in acetone offset. After the addition has ended, the mixture is stirred for hours at room temperature. The analysis of the

Table II

Mixture by thin layer chromatography shows that the reaction has ended Parts by volume of water are diluted, the yellow crystals are filtered off and dried. Yield 16.0 g. jo After recrystallization from methanol, 12.0 g of the specified compound of mp 284 to 286 ° C obtained.

Table II shows further compounds which are prepared according to Example 10.

Example starting compounds end product

F., ⁰ C.

11 trichlorotrimesonitrile and aniline

12 Trichlorotrimesonitrile and 4-BromaniIin

13 trichlorotrimesonitrile and 4-phenylenediamine

14 Trichlorotrimesonitrile and 3,4-Dimethoxyaniline

15 trichlorotrimesonitrile and 3-chloroaniline

16 trichlorotrimesonitrile and 4-chloroaniline

17 trichlorotrimesonitrile and 3-fluoroaniline

18 trichlorotrimesonitrile and 3-trifluoromethylaniline

19 trichlorotrimesonitrile and 3,4-dichloroaniline

2,4-dichloro-6- (anilino) -
trimesonitrile 241-242 2,4-dichloro-6- (4-bromanilino) -
trimesonitrile 332-333 2,4-dichloro-6- (4-aminoanilino) -
trinesonitrile decomposition
at 450 2,4-dichloro-6- (3,4-dimethoxyanilino) -
irimesonitrile 238-239 2,4-dichloro-6- (3-chloroanilino) -
trimescnitrile 226-227 2,4-dichloro-6- (4-chloroanilino) -
trimesonitrile 310-311 2,4-dichloro-6- (3-fluoroanilino) -
trimesonitrile 244-245 2,4-dichloro-6- (3-trifluoromethylanilino) -
trimesonitrile 263-265 2.4-dichloro-6- (3.4-dichloroanilino) - 250-251

trimesonitrile

Example 20

After the tomato leaf disease test, the ability of the compound under study is determined Tomato leaves against the pathogen causing the spot disease Alternaria rolani (ElI. And Mart.) Jones and Grout and to protect the late blight pathogen Phytophtora infestans (Mont.) DeBary. at This process produces tomato plants that are 13 to 18 cm tall who are 4 to 6 weeks old are used. One row of the plants is to be examined for each Mushroom with different doses of the test preparation

tes sprayed at a pressure of 2.8 kg / cm ² , the plant being rotated on a turntable in a fume cupboard. The center of the turntable is 114 cm from the nozzle of the spray gun. The preparation to be examined, which contains the active ingredient, acetone, an emulsifier stock solution and distilled water, is used in concentrations of up to 1000 ppm. of the active ingredient used. Lower concentrations of the active ingredient are obtained by using less active ingredient and larger amounts of water. The concentration of acetone and emulsifier is kept constant. After spraying, the plants are allowed to dry and the treated plants as well as the control plants, which have been sprayed with a preparation without active ingredient, are sprayed on a turntable while rotating with a spore suspension containing about 20,000 A. solani conidia per ml or 150,000 sporangia

Table III

ι ο

of P. infestans per ml. The spray gun used injects within 30 seconds Volume of 20 ml. The plants are kept in a moisture-saturated atmosphere for 24 hours 21 ° C (plants infected with A. solani) and at 16 ° C (with P. infestans infected plants) for spore germination and infection before moving to a greenhouse be spent. 2 days after the start of the experiment with A. solani and 3 days after the start of the experiment with P. infestans, the injuries on the top three fully expanded leaves are counted. the Values are expressed in percent disease suppression based on the number of control peaks of injuries received, converted. The doses and percent suppression are in the below table U! compiled.

Tesl connection

Dose, Percentage oppression TpM. A. solani P. infestans 256 100 100 128 98 100 64 83 98 32 63 97 16 40 98 8th 17th 87 128 100 100 64 90 99 32 83 99 16 47 96 8th 24 83 1000 - 98 1000 - 100 1000 - 100 128 99 100 64 95 98 32 85 97 16 77 95 8th 63 77 128 94 100 64 81 71 32 46 53 16 24 7th 8th 8th 0 128 95 92 64 72 90 32 67 84 16 62 79 8th 29 64 128 99 100 64 71 95 32 60 90 16 37 73 8th 13th 58

2,4-dichloro-6- (o-chloroanilino) trimesonitrile

2,4-dichloro-6- (p-hydroxyanilino) trimesonitrile

2,4-dichloro-6- (p-bromanilino) -trimesonitrile
2,4-dichloro-6- (anilino) -trimesonitrile
2,4-dichloro-6- (p-arninoanilino) trimesonitrile
2,4-dichloro-6- (ni-criloranilino) -trimesonitrile

2,4-dichloro-6- (p-chloroanilino) trimesonitrile

2,4-dichloro-6 ^ 3 ^ uro-2-methylanilino> trimesonitrile

2,4-dichloro-6- (2,4-difluoroanilino) trimesonitrile

continuation

Test connection

Dose. Percentage oppression TpM. A. solani 1'. inlcsliins 64 100 100 32 93 99 16 90 97 8th 81 98 4th 79 99 2 69 98 1 24 77 1000 100 100 256 80 87

2,4-dichloro-6- (2,3-dichloroanilino) trimesonitrile

2,4-dichloro-6 <3,4-dich! Orap.i! Ino) -tnineson! Tril

Example 21

Experimental preparations are used with regard to their inhibition of the growth of Erwinia amylovora (E. a.), Xanthomonas phaseoli (X. p.). Staphylococcus aureus (S.a.) and Escherichia coli (E.c.) in different Concentrations investigated. The starting preparation contains 0.125 g of the test compound (or 0.125 ml, if the test compound is a liquid), 4.0 ml of acetone, 2.0 ml of an emulsifier stock solution (0.5 percent of a Addition product of 8-30MoI alkylene oxide with a mixture of Cg-12-alkylphenols in water) and 94.0 ml of distilled water. The concentration of the test compound in this preparation is 1250 ppm. Lower concentrations of the test compound are obtained by diluting the starting preparation with Obtain distilled water.

2 ml of each preparation is placed in a test tube placed in a water bath set at 44 ° C. 8 ml of a 20 percent nutrient agar are added to the test tube from a stock preparation that has also been warmed to 44 ° C. A 1: 5 dilution and a final concentration of 250 ppm are obtained. of the active ingredient in the agar. The contents of the test tube are mixed thoroughly with a vortex mixer while it is still warm and then immediately poured into a sterile Petri dish (100 χ 15 ml) made of polystyrene. Once the agar has solidified, suspensions of each microorganism are simultaneously spread onto the surface of the agar. The plate is then incubated for 24 to 48 hours at 3O ⁰ C. The inhibition of growth of each organism is then determined visually. The percent growth inhibition is estimated in comparison to the growth of streak colonies on control plates obtained during separate experiments. The results are summarized in Table IV.

Table IV

Test connection

Concentration,
TpM.

Growth inhibition,%

E. a. X. p. S. a.

E. c.

2,4-dichloro-6- (o-chloroanilino) trimesonitrile

2,4-dichloro-6- {p-hydroxyanilino) trimesonitrile

2,4-dichloro-6- (annino) -trimesonitrile

2,4-dichloro-6- (p-aniinoanilmo> trimesonitrile

8th 100 50 100 100 4th 100 50 100 100 2 100 50 100 100 1 50 50 50 50 64 100 100 100 100 32 100 100 100 100 16 100 - 100 100 8th 100 50 100 100 32 100 - - 100 16 100 - - 100 8th 100 - - 100 4th 100 - - 100 250 50 - 50 100 128 100 - 50 100 64 50 - 50 100 32 50 _ 50 50

12th

Continue Tune

Test connection

Concentration.
TpM. E. a.

Growth inhibition,%

X. p. S. a.

2,4-dichloro-6- (m-chloroanilino) -trimesonitrile 2,4-dichloro-6- (o-hydroxyanilino) -trimesonitrile

2,4-dichloro-6- (o-bromanilino) -trimesonitrile 2,4-dichloro-6- (o-ethylanilino) -trimesonitrile 2,4-dichloro-6- (3-chloro-2-methylanilino) -trimesonitrile 2,4-dichloro-6- (3-fluoroanilino) -trimesonitrile 2,4-dichloro-6- (2,4-difluoroanilino) -trimesonitrile 2,4-dichloro-6- (2,3-dich! Oranilino) -trimesonitrile

2,4-dichloro-o- (3,4-dichloroanilino) -tiiinesonitri!

2,4-dichloro-6- (2,4-dimethylanilino) -trimesonitrile I

16 100 - - 8th 50 - 100 4th 50 - 50 250 100 100 100 128 100 100 100 64 100 50 100 32 50 - - 32 100 - 100 16 100 - 100 8th 50 - 50 32 100 - 100 16 100 - - 8th 50 - 100 16 100 - 100 8th 50 - 100 4th 50 - 100 250 100 - 50 128 100 - 100 64 100 - - 250 100 - 100 16 100 - 100 8th 50 - 50 250 100 100 100 32 100 100 100 16 100 100 100 8th 50 50 100 250 100 - 100 16 100 - 100 8th 50 - 100 4th 50 - 50 250 50 _ 50

In the same way, the known, in DE-AS 14 43 731undl9 15 799 described Verbin fertilize examined The results are summarized in the following Table IVa

Table IV a

Test connection

Conc Growth inhibition,% X-P. tration 100 (TpM) Li - 250 100 100 128 - 50 100 100 30th 50

S.a.

according to DE-OS 14 43 731
Tetrachloro-1 ^ -benzodinitrile

24-dichloro-4,6-difluoro-l 3-benzodinitrile 100

! • "ortsctzuim

Te> t \ r rhi nil u ng

according to DE-OS 14 43 731
2,4,5-trichloro-6-fluoro-1,3-benzodinitrile

according to DE-OS 19 15 799
Trifluorotrimesonitrile
Trichlortrimesonilri!

Kon / cn- growth inhibition, %
I lit ion

(IpM)

Xp.

64 100 100 32 50 50 16 - 50 250 100 100 300 100 100 100 100 100 30th 100 50

S.a.

A comparison with Table IV shows that the compounds according to the invention are significantly more active.

Example 22

Test preparations were tested with regard to their systemic action against Uromyces phaseoli bean rust investigated on Phaseolus vulgaris var. Pinto. The plants are in flower pots with a diameter pulled by 10 cm. The test preparation is in a dose of 45 ml, corresponding to 65 mg of the Test compound, or 29 kg per 0.4 ha, added to each flower pot. The trial preparation contains 0.1 g of the test compound (or 0.1 ml) if the active ingredient is a liquid, 4.0 ml of acetone, 2.0 ml of one Emulsifier stock solution (0.5 percent Triton X-155 in water) and 94.0 ml of distilled water. The concentration the test compound in this preparation is 1000 ppm. Lower concentrations of the active ingredient are obtained by diluting the starting preparation with distilled water.

24 hours after application of the test compound, the plants are washed with an aqueous suspension infected, which contains the uredospore species. Afterward the plants are 16 to 18 hours at 15 ° C and 100 Percent relative humidity. The pustules are counted 7 to 10 days after infection and the percentage of disease suppression, based on the pustule development in untreated control plants, calculated. Table V summarizes the results.

Table V

Test connection

Dose percentage

Disease kg / 0.4 ha suppression

2,4-dichloro-6- (3-trifluoro-29,100

methylanilino) -trimeso-

nitrile

2,4-dichloro-6- (2,3-di-29,100

methylanilino) -

trimesonitrile

Example 23

For determining the viricidal effect on the maize warping and dwarfing mosaic virus experimental preparations with 0.1 g of test compound (or 0.1 ml, if the compound is liquid), 4.0 ml Acetone, 2.0 ml of an emulsifier stock solution (0.5 percent Triton X-155 in water), and 94.0 ml of distilled Water produced The test preparations water the earth as well as the leaves The maize mosaic virus on Zea mays var. Golden X Bantam is sprayed in flower pots with a Drawn diameter of 10 cm. Before treatment, the leaves are infected with the virus, whereby the Sheets are rubbed with emery paper.

To spray the leaves, 33 ml of the test preparation (1000 ppm. Active ingredient) are sprayed onto the plants at a pressure of 21 kg / cm ² , which are rotated in a fume cupboard on a turntable. 24 hours after spraying, the test preparation is poured onto the soil in each flower pot in an amount of 45 ml, corresponding to a dose of 29 kg / 0.4 ha. Ten days after infection, the percent disease suppression is determined visually. In Table V! the results are compiled

Table VI Test connection

dose kg / 0.4 ha

TpM.

percentage disease suppression

2,4-dichloro-6- (anilino) -trimesonitrile

2,4-dichloro-6- (2,3 "dichloroanilino) trimesonitrile

2,4-dichloro-6- (3,4-dichloroanilino) -tr: mesonitrile

Example 24

Experimental preparations are being investigated with regard to their inhibition of Pseudomonas phaseolicola Experimental preparation containing 0.24 g of the test compound (or 0.24 ml if the test compound is liquid), 4.0 ml Acetone, 2.0 ml of an emulsifier stock solution (0.5 test compound Percent of the emulsifier mentioned in Example 21 in water) and 94.0 ml of distilled water are both

for soaking the soil as well as for spray treatment

of the leaves produced Individual tomato plants of the Rutgers variety are grown in flower pots from about 10 cm in diameter to a size of 8 to 13 cm. 1 or 2 hours before watering the soil and spraying the leaves, the trunk is infected at the cotylodon node with a cell suspension of Pseudomonas phaseolicola. To soak the soil, the test preparation is applied to the soil surface of each pot in an amount of 17.5 ml. This corresponds to a dose of 1000
1000
1000

100 100 100

Test compound of 29 kg / 0.4 ha. 10 to 14 days after After treatment, the tumor formation is observed visually. Table VII summarizes the results.

Table VII Dose percentage

Tumor under kg / 0.4 ha pressure

2,4-dichloro-6- (o-bromo-64 100

anilino) -trimesoni? -il

2,4-dichloro-6- (o-ethyl- 64 100

anilino) trimesonitrile

2,4-pichloro-6- (2,4-difluoro-64 100

anilino) trimesonitrile

2,4-dichloro-6- (3,4-di- 64,100

methoxyanilino) -

trimesonitrile

230 233/32

Claims (1)

Patent claims: 1. 2,4-dichloro-6-anilino-13,5-benzotrinitrile der general formula Cl ¥ YY_ χ NC— \ / ^