DD267902A1 - FUNGICIDES AND BACTERICIDES - Google Patents

Abstract

The invention relates to novel fungicidal and bactericidal compositions which contain, in addition to customary auxiliaries and tracer substances, alk (aryl) oxyacetanilides of the general formula in which R is hydrogen or CH 3, R 1 is C 1 -C 4 -alkyl, cyclohexyl, phenyl or in the p-position Chlorine substituted phenyl group mean.

Description

CH - ClI ₂ -

NC CiIpO - H ₁

Il

In the R - H or CH]

Rl - C ₁ -C ₄ -AlkVl ₁ cyclohexyl, phenyl or an in p-position by chlorine-substituted phenyl group, mean. The preparation of the novel compositions according to the invention is carried out by known methods by acylation of N- (2-nitro-1-aryl-eth-1-yl) -anllinen with alk (aryl) oxy-acethylchloriden in benzene in the presence of Pyridln as hydrogen chloride acceptor. The compounds are new and not yet described in the literature. Their structure was confirmed by elemental analyzes, IR spectra, mass spectra and 'H NMR spectra.

The new fungicidal and bactericidal agents have a broad spectrum of antimicrobial activity and are particularly suitable for controlling fungal and bacterial diseases on crop plants, especially potatoes. As an example of the compounds according to the invention, the active ingredients listed in Table 1 may be mentioned.

Table 1: Alkoxyacetanilides

CH-CH ₂ -

N-C-CHPO -

connection

F ( ⁰ C)

A H CH ₃ 77-78 ' B H ^ H ₅ 94-97 C CH ₃ CH ₃ 118-119 D CH ₃ C ₂ H ₆ 64-66 e H cyclohexyl 112-114 F CH ₃ cyclohexyl 128-131 G H 4-CI-C ₄ H ₄ 85-87 H CH ₃ 4-CI-CeH ₄ 113-115 I H C ₈ H ₆ 97-99 J H nC ₄ H, 65-67 K H 1-C ₄ H, 87-89 L CH ₃ IV-C ₄ H ₉ oil M H 1-C ₃ H, 85-88 O CH ₃ iC ₄ H, 55-57 P CH ₃ JC ₃ H, 47-50 embodiments

Example 1: Test on ascomycetes The agents according to the invention are introduced into nutrient agar, to which the test organisms have been inoculated. It came Active substance concentrations of 100 ppm and 1000 ppm are used. The evaluation took place on the 10th day according to the following rating scheme:

1 = no growth inhibition

2 = weak growth inhibition

3 = strong growth inhibition

4 = complete growth inhibition

The fungicidal activity of the agents according to the invention is shown in Table 2. As site fungicides Thiuram and Zineb were used for comparison.

Table 2: Effect of the agents according to the invention against Fusatium culmorum (F.c.) and Botrytis cinerea (B.c.)

connection BoniturenB.c. 100 ppm BoniturenF.c. 100ppm 1000 ppm 4 1000 ppm 4 A 4 4 4 4 B 4 4 4 1 C 4 4 4 4 D 4 4 4 1 L 4 4 4 4 M 4 4 4 4 N 4 4 4 4 O 4 4 4 4 P 4 4 4 4 Thiruram 4 1 4 1 Zineb 4 4

Table 2 shows the marked effect of the new agents according to the invention, especially against Zineb. Example 2; Action against Phytophthora infestans (P. i.) Tomato plants were treated with a spray mixture containing 0.1% and 0.01% of active ingredient of the inventive agent (by Formulation in a water emulsifiable or suspendable form) contained. After the drying of the Spray coating was infected with the test fungus P.I. The incubation was carried out at 18 ° C and a relative humidity of 96-100%. Foliar infestation caused by the harmful fungus was determined 5 days after infection according to the following rating scheme. At the same time the plant compatibility was recorded. rating scale:

1 = strong infestation by P.i. like untreated control

2 = average infestation

3 - = low infestation

4 = no infestation by P. i. Leaf healthy plant tolerant:

1 = sheet severely damaged

2 · * mean damage

3 = low damage

4 = sheet without damage

The results of this test are shown in Table 3. The credit score is the average of 3 repeats. The phytotoxicity is in brackets after the credit score for P. i. specified.

Table 3: Effect of the agents according to the invention against Phytophthora infestans on tomatoes

connection 0.1% AS monitorings 4.0 (4.0) 0.01% AS A 4.0 (4.0) 3.7 (4.0) L 4.0 (4.0) 3.7 (4.0) Zineb 4.0 (4.0) 1.7 (4.0) maneb 4.0 (4.0) 1.3 (4.0) Ridomil / Zineb 3.7 (4.0)

Table 3 shows the very good activity against Phytophthora infestans of the inventive compositions, especially at low concentrations.

Example 3: Action against Turolopsis yeast The activity against yeasts was determined in liquid cultures. The compositions according to the invention were used in concentrations of

100ppm and lOprr.i dissolved in the nutrient solution added. Subsequently, the percentage inhibition against the u '»treated control is determined.

Table 4 shows the results from this test. Table 4: Effect of the agents according to the invention against Turolopsis yeast

connection Inhibition (%) 10ppm 100 ppm 74 B 1C0 66 e 100 73 G 100 66 H 100 70 I 100 66 J 100 100 K 100 100 thiuram 100 71 Zineb 100 68 maneb 100 0 untreated 0

Table 4 shows the very good effect of Compound K especially against Zineb and Maneb. Example 4: Bactericidal action The bactericidal activity was developed against Erwinia carotovorum in liquid culture. The substances to be tested were in Added concentrations of 100 ppm and 10 ppm of the nutrient solution in a dissolved state. The percentage inhibition compared to the untreated control is then determined. Table 5 shows the results from this test. Table 5: Action against Erwinia carotovorum (E.c.)

Inhibition (%) Compound E.c.

100 ppm 10 ppm

A 100 87 B 100 76 C 100 70 D 100 61 e 100 85 F 100 90 H 100 85 I 100 79 K 100 85 L 100 80 O 100 82 P 100 69 thiuram 100 42 chloramphenicol 100 4

Table 5 shows the very good activity of the compounds A, E, F, H and K even against chloramphenicol.

Claims (2)

Fungicidal and bactericidal agents, characterized in that they contain, in addition to customary auxiliaries and carriers, as active substances, compounds of the general formula NC-CH ₉ -O-It,
Il * ^ in the R = H or CH ₃ R ₁ = C ₁ -C ₄ -AlkYl, cyclohexyl, phenyl or substituted in the p-position by chlorine substituted phenyf group. Field of application of the invention The invention relates to new fungicidal and bactericidal agents for controlling diseases on crop plants. Characteristic of the known state of the art To combat fungal diseases on crops are widely salts of E'hylen-bis-dithlocarbamidsäure, z. Maneb (U.S. Patent No. 2,504,404, U.S. Patent No. 2,710,822), Mancozeb (U.S. Patent No. 2,604,404, Belg. PS 996264) and Zineb (U.S. Patent No. 2,457,674). Of great importance as fungicides, in addition to the metal salts of dimethyldithiocarbamic acid, the thiuram derivatives, eg. As the Tetramethylthiuramdisulf id (US-PS 1972 961). The disadvantage of the metal salts of ethylene bisdithiocarbamates is that they only mediocre fight fungi such as Fusarium culmorum, Botrytis cinerea, Phytophthora infestans and yeasts. They are ineffective against bacteria and partly phytotoxic. Japanese Patent 7021297 and DD Patents 92602, 209716 and 209955 describe the fungicidal effects of α-halogenated acetophenones. The compounds listed therein are also phytotoxic and show only minor effects on Fusarium culmorum, Botrytis cinerea and yeasts. In DE-PS 2 823658 jn a-thiocyanato-acetophenono claimed as bactericides. The listed compounds show little action against Pike. Ridomile-type 2,6-disubstituted aniline derivatives (DE-PS 2212 268, BE-PS 1445 387, US Pat. No. 4,141,989) are claimed to be effective against Phytophthora infestans. These compounds are complex in the synthesis and therefore expensive. In addition, their effectiveness against other fungi is low, they are gege .- <bacteria ineffective and phytotoxic, and at low application rates does not satisfy their effect. Object of the invention The aim of the invention is to develop new agents which have a broad fungicidal spectrum of action with additionally good bactericidal activity with excellent KulhirpfianzenvertrSglichkeit. Presentation of the essence of the invention The object of the invention is to find new substance classes for fungicidal and bactericidal active substances, which are distinguished by their complex effectiveness, low synthetic effort and good application and environmental compatibility. This object is achieved according to the invention in that the novel fungicidal and bactericidal agents, in addition to customary auxiliaries and excipients, are active compounds of the formula x'xoxyacetanilides,