DE1079379B - Fungicides - Google Patents

Description

Fungicidal Agents The invention relates to new fungicidal agents that can be used in industry and agriculture.

These agents are based on ethylene derivatives of the general Formula Ar -C "H" n-X-CCl = CHCI I built up. In this formula, Ar means an aryl radical, preferably the phenyl radical, which can also carry one or more substituents, such as, in particular, halogen atoms or alkyl, alkoxy or nitro groups; za is 0 or 1, and X represents an S O or S 02 group. These new fungicidal compounds can e.g. B. obtained by oxidation of the corresponding sulfides, d. H. from Compounds which correspond to the general formula, but in which the group X is replaced by a sulfur atom.

The ethylene derivatives have the general formula given above a significant fungicidal effect; they are particularly active against the following organisms: Actinomyces Maroc 43, Rhizopus nigricans, Candida albicans, Aspergillus niger, Penicillium ansari mofidi, Botrytis cinerea, Alternaria tenuis, Fusarium culmorum, Pestalozzia palmarum.

The fungicidal activity of these compounds has been demonstrated in vivo the following tests confirmed, with the comparison substance [N-trichloromethylthio-tetrahydrophthalimide] (known in the trade as "Captan") was chosen.

Experiment on the anthracnose of the bean Young bean plants are after the full development of the seminal lobes by atomizing a solution, emulsion or suspension of the products to be examined (1 ml / stem). 24 hours After treatment, the plants are normalized by atomizing a suspension of spores of the selected parasite (Colletotrichum lindemuthianum; concentration 500,000 spores per ml; Age 21 days) artificially infected. After 5 days of incubation at 22 ° C, the development of the parasite is determined by looking at the leaves and necroses formed on the axes of the plant are counted. In the following The table shows the minimum concentration (in mg / 1) of product that has a 95- causes up to 100% inhibition of growth on C. hemuthianum. attempt against grain rot (method according to Gassner) cereal grains with the to be examined If the product is suitably encased, it will be abundant with compost spores (tilletia caries; 15 mg spores per g grain) infected. The grains so treated are allowed to germinate on moist soil at 10 ° C. After 12 to 15 days of incubation one notices the appearance of sporidia on the seed skin of the grains. In the The following table shows the minimum concentrations for this experiment (in mg / kg Cereals) indicated the formation of sporidia of T. caries on cereal grains impede.

Trial against powdery mildew Young leaves of the grapevine are on the underside by atomization (1 ml per leaf) of a solution, emulsion or suspension of the zu the product being examined. 24 hours after that will be on the bottom of the leaf 20 drops of a normalized suspension of powdery mildew pores (Plasmopara viticola; Concentration 100,000 spores per ml; Age $ days). After 5- Incubation for up to 7 days at 22 ° C in moisture-saturated the atmosphere - note: the appearance of the conidiophores of the parasite is noted. In the following The table shows the minimum concentrations (in mg / 1) of product for this experiment which prevent the formation of conidiophores on young leaves of the grapevine.

The results of the experiments described above are compiled in the following table. ... General formula: g anthracnose Corn rot powdery mildew C. 1. T. c. P. v. - Cl HH -SO- - 250 300 - Cl HH _S02- 500 250 250 - Br HH -so, - 750 275 300 - CH, HH _S02- 750 250 250 - O CH, HH _S02- 750 300 400 C H3 CH, H _S02- 500 300 - Cl C1 H _S02- 500 200 - Cl CH, H _S02- 500 300 - H Cl Cl _SO2- 300 - - CH, Cl H _SO2- 500 - - Cl NO, H _S02- 750 300 - Cl C H2 S 02 C Cl = CH Cl 750 250 - Control substance> »Captan«: # 'N - S - C C13 750 500 500 ## C 0f Results in the open field On the basis of the favorable results in the laboratory, one of the products according to the invention, namely 1,2-dichloro-lp-chlorophenylsulfonyl-ethylene, was selected for tests in the open field. The results obtained fully confirm the activity found in the laboratory. These tests were carried out on the following cases: corn rot, oidium of the spindle tree (Evonymus europaea), oidium of the cucumber, oidium of the grapevine (grape disease), septoriosis of the celery (celery rust), fire or rust of the mint, scab disease of the apple tree (leaves), Scab disease of the apple tree (fruits).

Excellent results have been obtained, particularly in the following Try: Grain rot: the grains are treated with a powder, which contains 20% active ingredient, with 200 g per hundredweight of grain. The grains are then infected with 0.4 g of putrefactive spores (Tilletia tritici) per kg of grain. at the harvest is found to be 0.79% infestation at the first attempt and at the second attempt 0.50% infestation, based on the total amount.

Oidium of the spindle tree: The product in the form of a powder with 70% active ingredient was used in an amount of 150 g of active ingredient per 100 liters of water for oidium of the spindle tree. The results are good and comparable to those obtained with a powder with 70% sulfur content used in a dose of 10% .

Scab disease of the apple tree on the leaves: The product was applied in the form of a powder with 70% active ingredient in an amount of 350 g of powder per hectolitre of water. The efficiency coefficient was found to be 98.9% . In the same experiment the coefficient of effectiveness on Sphaeropsis was found to be 96.6%.

Scab disease of the apple tree on the fruits: coefficient of effectiveness 97.20 /,).

Oidium of the cucumber: The product was in the form of a powder with 70 l) /, Active ingredient content in amounts of 350 g and 150 g of active ingredient per hl of water. In both proportions, the product showed a good preventive effect.

From the above test results it can be seen that the most effective products are those in which the radical SO " Ar in the above general formula IX is 4-chlorophenyl, 4-methylphenyl, 4-methoxyphenyl, 3,4-dimethylphenyl or 3, 4-dichlorophenyl radical and ya the number 0 (C "H" z then means a single bond). Such compounds are, for example, 1,2-dichloro-1-chlorophenylsulfonyl-ethylene and 1,2-dichloro-1 -methylphenylsulfonyl-ethylene, 1,2-dichloro-1-p-methoxyphenylsulfonyl-ethylene, 1,2-dichloro-1- (3 ', 4'-dimethyl-phenylsulfonyl) -ethylene and 1,2-dichloro-1 - (3 ', 4'-dichloro-phenylsulfonyl) -ethylene.

The active compounds according to the invention can be used in various forms be, with the finished preparation one or more active ingredients according to the specified Formula I may contain. The active ingredient can be used in conjunction with inert diluents be applied so that powders, dusts, aerosols, emulsions or solutions in organic or aqueous-organic medium can be obtained. In the case of the aqueous emulsions for use in industry or agriculture, it is particularly advantageous to add an ionic or nonionic wetting, dispersing or emulsifying agent; in particular, the nonionics are useful because they act against electrolytes are not sensitive. The emulsion is preferably in the form of a auto-emulsifiable concentrate containing the active ingredient dissolved in a dispersant or in a solvent compatible with the dispersant, prepared, the concentrate is then made ready for use by simply adding water will. The agents can also contain the active ingredient mixed with synergistic products contain.

For the production of powders, inert mineral carriers can be used or organic dispersants such as lime, kaolin, bentonite, talc, calcined Use magnesia, kieselguhr, tricalcium phosphate, cork flour, etc. The mixture can be prepared by grinding the active substance with the inert carrier. But you can also use a solution of the active ingredient in a volatile carrier Impregnate solvent that is subsequently evaporated.

When the active ingredients according to the invention are applied in the form of a solution solutions in aromatic hydrocarbons are preferably used, such as xylene or toluene, or mineral or vegetable oils or mixtures this solvent.

You can also use aqueous emulsions or suspensions that either directly or from powders or solutions in suitable solvents Dilute with water. In order to obtain stable emulsions preferably ionic or nonionic emulsifiers or dispersants, such as. B. Sulforicinate, alkyl sulfonates, quaternary ammonium derivatives or products on the Polymerized ethylene oxide base added.

The following examples are intended to explain the invention in more detail; as Active substance can in each case one or more compounds of the general ones given above Formula I can be used.

Example 1 A mixture of 200 g of active ingredient, 500 g is vigorously stirred cc xylene and 500 cc of an emulsifier based on polymerized ethylene oxide (»Tween 80u). The fine suspension obtained is mixed with water with vigorous stirring diluted to a final volume of 2001. It is used to treat beans for anthracnose used.

Example 2 150 g of active ingredient are mixed with 1 kg of talc and 100 g of »Tween Grind 80u finely. The resulting powder is sieved so that it can pass through a sieve No. 6 (German Pharmacopoeia, 6th edition (1926), p. XXIX) goes through the particle of 160 microns. The powder obtained in this way can be suspended in 100 liters of water and to protect certain plants, especially tomatoes and beans, against fungi be used.

Example 3 200 g of active ingredient become intimate with 600 ccm of "Tween 80t" mixed and this suspension diluted with 2001 water and stirred vigorously. the The solution obtained can protect beans against anthracnose and apple trees against Scab, mint against rust and grapevine against oidium. Example 4 40 g of active ingredient and 160 g of kieselguhr are intimately mixed. After seven 200 g of a powder containing 201) /, active ingredient to protect 100 kg of grain are obtained can be used against rot.

Example 5 20 parts of active ingredient are dissolved in 50 parts of acetone. With this The solution obtained in this way is impregnated with 80 parts of talc and the acetone in vacuo evaporates. The powder thus obtained can be used directly or suspended in water will.

Claims (2)

PATENT CLAIMS: 1. Fungicidal agents, characterized by a content of one or more compounds of the general formula Ar - CH, n - X - CCl = CH Cl where Ar is an aryl radical, preferably the phenyl radical, which also has one or more substituents, such as halogen atoms in particular , Can carry alkyl, alkoxy or nitro groups, and in which -a denotes the number 0 or 1 and X denotes an SO or SO group, as an active ingredient. 2. Fungicidal agents according to claim 1, characterized in that the active ingredient together with an inert Carrier is used.