DE1028828B - Fungicides - Google Patents

Description

GERMAN

It has been found that p-aminophenyl diazo compounds good fungicidal activity. Known for combating cereal diseases Oxydiazo compounds are superior to these substances in their action against emergence diseases. The Her- S The diazo compounds can be positioned and stabilized in a known manner. Changes to the Amino group or substitution in the phenyl nucleus are only of limited importance for effectiveness.

Examples of fungicidal compounds of this class are called:

-CONH-

-N = N- SO, K

Potassium p-acetylaminobenzene-diazosulfonate

Fungicides

Applicant:

Paint factories Bayer Aktiengesellschaft, Leverkusen-Bayerwerk

H ₃ C-CONH - / V- N = N- Cl + ZnCl ₂ p-acetylaminobenzene-diazonium chloride-zinc chloride

H ₃ C-CONH- <V- N = N- N.

p-acetylaminobenzene-diazopyrolidine

Dr. Ewald Urbschat, Cologne-Mülheim,

and Dr. Paul-Ernst Frohberger, Odenthal (Cologne district),

have been named as inventors

CH ₂ -CH ₂ H ₅ C ₂ CH ₂ -CH ₂

H ₈ C-CO-NH

-N = N-SO ₃ -V

p-acetylaminobenzene diazo-p-chlorophenyl sulfonate

H ₃ C

HX

.N-

V-N = N-S 0, Na

sodium p-dimethylaminobenzene-diazosulfonate

H ₉ N-

> —N = N-SOoNa

p-aminobenzene-diazosulfosauresodium

H ₃ C

N = N-SO ₃ H

p-Dimethylaminobenzene-diazosulfonic acid

-N.

SO, well

HbCo

p-diethylaminobenzene-diazosulfonate sodium

The application takes place in a known manner, for. B. as dry dressing or in dissolution and slurry as wet dressing (slurry dressing) etc. They can also be used in conjunction with other fungicides and / or insecticides and / or bird repellants.
40

example 1

Experiments with peas (Alderman)

These experiments were carried out in an unheated greenhouse that was lit only with daylight. Ordinary compost was used, which is rich in various phytopathogens Fungi was contaminated, so that there was a possibility of infection with emergent diseases from the ground and the experimental conditions must be viewed as severe. The preparations were used as dry dressings in stretched to the specified concentrations with talc and applied in the usual way. the The application rate was a uniform 2 g per kg of seed.

809 507/408

Preparation concentration in ° / o

Healthy plants, based on a hundred peas laid out

unheated phenyl-Hg-acetate (for comparison)

HX-CONH

HX-CONH

the same.

H ₃ C-CONH-

= N-n:

, CH ₂ - CH ₂

C Ho -

2 ^^ 2

the same.

HX- CO - NH-

= N-SOo

HX

the same.

unheated phenyl-Hg-acetate (for comparison)

N = N-SO ₃ Na

the same.

unheated phenyl-Hg-acetate (for comparison)

-N = N-SO ₃ Na

the same.

HX

N = N - SO, H

same as 2.2Hg
5

15th
50

15th
50

15th
50

9 39

51

60 67

25th

39 56

35

63 64

25th

15th 26th 50 51 _ 6th 2.2Hg 32 5 66 15th 77 50 66 _ 2 2.2Hg 15th 5 32 15th 56 50 22nd

65

64 30

5 preparation 6th Healthy plants,
out to a hundred
put peas related Serial
No. unheated
Phenyl mercury acetate (for comparison)
H ₅ C ₂
, N- / NN = N-SO ₃ Na
H ₅ C ₂
the same
the same Concentration
tion in ° / o 8th
46
51
60
74 d)
1
2
3
4th
5 2.2Hg
5
15th
50

Example 2

Wheat stone brandy spore germ test (Gassner method)

The wheat stone spore germ tests were carried out at an application rate of 1 g per kg of seed the Gassner method. The preparations were used as 25 prepared under Example 1 as a dry pickling agent and

Serial
No. HgC preparation Concentration
tion in ° / o Spore germination 1 unheated about 75% H ₃ C ⁷ 2 - / VN = N-SO ₃ Na 30th 0.000% H ₃ C 3 the same 15th 0.01% H ₃ C ^X 4th - / NN = N-SO ₃ H 30th 0.000% H ₆ C ₂ . 5 the same 15th 0.003% H ₆ C ₂ 6th - / V- N = N-SO ₃ Na 30th 0.000% 7th the same 15th 0.003% 8th the same 10 0.005% 9 the same 5 0.005%

Example 3

p-Dimethylaminobenzenediazosulfonic acid was in 0.3% strength aqueous solution as a fungicidal spray successfully against the brown rust of wheat (Puccinia triticina) applied. It was shown that the rust pustules on the wheat leaves after artificial infection almost could be prevented completely.

Example 4

The table below shows the effectiveness of the compounds as fungicidal soil treatment agents

Exposure. The tests were carried out in the usual way. Naturally contaminated compost soil became treated with the specified preparations in such a way that the preparations, stretched with talc, with the soil have been thoroughly mixed. Mark peas were then sown at a depth of 3 cm and in a cool greenhouse left to germinate at temperatures around 12 ° C. The number of healthy plants that consist of one hundred each Peas have emerged, provides information about the effectiveness of the preparations when you compare them with the percentage Comparing emergence of healthy plants in untreated compost soil.

Soil treatment trial with garden peas Onward

Serial
No. H ₃ C-CONH- H ₃ C preparation = N-SO ₃ K expenditure
amount in g
per kg of soil Healthy plants after.
4 weeks to a hundred
laid out peas sourced 1 untreated - 1 2 H ₃ C _x H ₃ (T 5 24 3 ) n- H ₅ C ₂ . - / V-N = N-SO ₃ Na 25th 55 4th H ₃ C ⁷ H ₆ C ₂ \ / 100 66 5 5 42 6th H ₂ N- - / V-N = N-SO ₃ Na 25th 82 7th \ / 100 93 8th 5 32 9 - / V- N = N-SO ₃ H 25th 49 10 100 90 11 = N-SO ₃ Na 5 50 12th / V- ⁿ 25th 83 13th \ / 100 94 14th
15th / \
/ V-N 5
25th 18th
30th 16 \ / 100 73

For comparison with the one used to combat cereal diseases Known oxydiazo compounds are various experiments in the table below Peas put together. The tests were carried out in the usual manner.

The seeds were jekg at an application rate of 2 g Seeds with a dry dressing agent containing the specified compounds in the specified concentrations contained, pickled and placed 3 cm deep in naturally contaminated compost soil (predominantly Pythium ultimum).

The experiment was held at temperatures around 12 ° C, so that by delaying the identifier and by Prolongation of the susceptible stage of the seedlings, particularly severe test conditions came about.

The effectiveness of the dressing agents is characterized by the number of healthy plants that arise from every hundred seeds.

Serial
No. preparation H ₅ C ₂ Concentration of
Preparation in
Dry mordant Healthy plants,
out to a hundred
put peas related 1 unheated _ 7th 2 Sodium l-oxy-S-chlorophenyl ^ -diazosulfosaures
HO- / V- N = N- SO ₃ Na 5%
15% 11
26th Cl 3 sodium p-dimethylaminobenzene-diazosulfonate
H ₃ C. 5%
15% 66
77 / N- /> -N = N-SO ₃ Na 4th p-Dimethylaminobenzene-diazosulfonic acid 5%
15% 65
64 . ^ N- / VN = N-SO ₃ H H ₃ C ^X 5 p-diethylaminobenzene-diazosulfonate sodium
H ₅ C ₂ V 5%
15% 51
60 N- / ^ VN = N-SO ₃ Na

Claims (1)

10 Claim ·. _{0 (s} j aryl radicals, while R ³ represents the radicals anFungizide agent containing p-aminophenyl-diazo-organic or organic acids or salts thereof compounds of the general formula or for an optionally substituted amino rest stands. ^R1 \ \ __ N = NR ³ f Publications considered: German Patent No. 696 766;
in which R ¹ and R ^{2 represent} hydrogen, alkyl, Aryl Chemisches Zentralblatt, 1943, I, p. 80.