DE2133056C3 - Use of NJS-di-alkyl-N'aryl-substituted guanidines for combating powdery mildew and gray mold on plants - Google Patents

Description

R:

R ': CH ₃ , C ₂ H ₅₁ HC ₃ H ₇ , iC ₃ H ₇ or n-CiHgund

X ₁ Y

and Z: H, Cl ₁ Br or CF ₃

mean, or the general formula X

NHCN

ίο

15th

20th

25th

40

R 'NH ■ HB

where R, R ', X, Y and Z have the abovementioned meaning and B is one of the anions Cl', CH ₃ SO4 \ (CH ₃ ) ₂ - NCSS ', S ₄ O ₆ "or C ₆ H ₂ (NO ₂ J ₃ O 'means, if appropriate with a carrier for combating powdery mildew and gray mold on plants 2. Use of j5

Ν, Ν-dimethyl-N'-m-chlorophenylguanidine, Ν, Ν-Dimethyl-N'p-bromophenylguanidine, Ν, Ν-Dimethyl-N'-m-trifluoromethylphenyl-

guanidine,
N-methyl-N-ethyl-N'-m-chlorophenyl-

guanidine,
N-methyl-N-ethyl-N'-S ^ -dichlorophenyl-

guanidine,
N-methyl-N-propyl-N'-m-chlorophenyl-

guanidine,
N-methyl-N-butyl-N'-m-chlorophenyl-

guanidine,
N-methyl-N-propyl-N'-m-trifluoromethylphenylguanidine,

the dimethyl dithiocarbamate des Ν, Ν-dimethyl-N'-m-chlorophenylguanidines orN.N-dimethyl-N'-m-trifluoromethyl-

phenylguanidins or
Ν, Ν-dimethyl-N'-m-chlorophenylguanidine-

tetrathionate
according to claim 1.

but also negative properties. They can damage the plants if they are not effective enough an air temperature below 20 ° C and overall only have a weak fungicidal effect.

The "Karathan" (2,4-dinitro-6-sec-octylphenyl crotonate) has extensive use in the control of powdery mildew in agriculture found. When using »Karathan« in concentrations of 0.025 to 0.05% of the active ingredient however, burn marks were observed on the plant leaves

To combat powdery mildew, the »Morestan« (6-methylquinoxaline-23-dithiocyte carbonate) was also found the Bayer company as very effective (cf. F. Grewe / H. Kaspers, "Plant Protection Message Bayer", vol. 18, pp. 1-23, 1965). However, the »Morestan« has a low effectiveness against other pathogens Diseases and in particular against the gray mold on plants.

Furthermore, the use of the preparation »Euparen« (N.N-Dimethyl-N'-phenyl-fN'-fluorodichloromethylj-thiosulfamide) known for combating diseases caused by the fungi Botrytis sp. be evoked (Plant protection message Bayer, Vol. 21, p. 147, 257, 1968). M. Bonnet (J. Hortic. ScU Vol. 44, p. 81, 1969) reported about the inhibiting effect of the preparation »Euparen« on Sphaerotheca achemillae. That is also known Use of »captan« (N-trichloromethylmercapto-4-cyclohexane-1,2-dicarboximide) and of "Difolatan" (N-1,1 ^ -Tetrachloräthylmercapto ^ -cyclohexen-1,2-dicarboximid) to combat the plant-damaging fungi Botrytis sp. (F. Stellwaag-Kintler, Weinberg and Keller, Vol. 16, p. 109, 1969; G. Etter "Meded. Rijksfac. landbouwwetensch. Gent ", Vol. 31, pp. 837, 1966).

However, the preparations "Euparen", "Captan" and "Difolatan" have no or only weak activity towards powdery mildew fungi.

Finally, from FR-PS 15 41 647 fungicides based on N-arylguanidine derivatives are known which have high bactericidal, herbicidal, insecticidal and fungicidal activity; they own the general formula

ArNHCNR'R "

45

55

The present invention relates to the use of Ν, Ν-di-alkyl-N'-aryl-substituted guanidines for Combating powdery mildew (Erysiphaceae) and gray mold (Botrytis) on plants.

It is known that to combat powdery mildew> 5 zen inorganic sulfur preparations can be used. The sulfur supplements that have a high Effectiveness against powdery mildew have NR

where Ar is a mono- or polycyclic aromatic radical which contains various substituents and R, R 'and R "are the same or different low molecular weight aliphatic radicals, one of which is a low molecular weight Can be alkoxy group. However, the mentioned connections become more complicated with the help and more expensive processes.

Such N-arylguanidines are those in which R in the above formula is hydrogen and Ar is an optionally halogen-substituted phenyl radical, from Chem. Abstr. 66 (1967), Ref. 75768 generally as insectofungicides and those in which R 'also denotes hydrogen, from Patent Quick Report Part B 1967, Ref. 3 47-209 as fungicides against anthracnosis of the cucumber, Alternaria kikuchiana of the pear and various ¹ known rice diseases.

The object of the invention is therefore to determine fungicides which can be easily produced and which are prior all at the same time a high effectiveness against powdery mildew and fungi of the Botrytis tribe (Gray mold) own.

The invention relates to the use of compounds of the general formula

NH-C -N

Il \

NH R '

CH ₃ , C ₂ H ₅₁ H-

CH ₃ , C ₂ H ₅ , n-QjH ?, iC ₃ H ₇ or nG, H ₉ and

R:
R ':
XY

and Z: H, Cl, Br or CF ₃

mean, or the general formula X

<f

nhcn

R 'NH-HB

where R, R ', X, Y and Z have the abovementioned meaning and B is one of the anions Cl', CH ₃ SO /, (CH ₃ J ₂ -NCSS ', S ₄ O ₆ "or C6H2 (NO ₂ ) ₃ O 'means, if appropriate with a carrier for combating powdery mildew and gray mold on plants.

Of the compounds mentioned, the most effective against powdery mildew fungi that attack cucumbers are the following:
the dimethyldithiocarbamates of

Ν, Ν-dimethyl-N'-m-chlorophenyl-guanidine or Ν, Ν-dimethyl-N'-m-trifluoromethylphenylguanidine;

the tetrathionate of

Ν, Ν-dimethyl-N'-m-chlorophenylguanidine; Ν, Ν-dimethyl-N'-m-chlorophenylguanidine; Ν, Ν-dimethyl-N'-p-bromophenylguanidine, Ν, Ν-dimethyl-N'-m-trifluoromethylphenylguanidine;

N-methyl-N-ethyl-N'-m-chlorophenylguanidine; N-methyl-N-ethyl-N'-β ^ -dichlorophenylguanidine;

N-methyl-N-propyl-N'-m -chlorophenylguanidine; N-methyl-N-n-butyl-N'-m-chlorophenyl-

guanidine or
N-methyl-Nn-butyl-N'-S ^ -dichlorophenylguanidine.

These substances were effective at a concentration of 0.025 to 0.1% and combated the development of the disease up to 80 to 100%.

With regard to gray mold, the following substances proved to be the most effective:

Ν, Ν-dimethyl-N'-m-chlorophenylguanidine; the dimethyldithiocarbamate des

Ν, Ν-dimethyl-N'-m-chlorophenylguanidines; the methyl sulfate des

N, N-dimethyl-N'-phenylguanidine; Ν, Ν-Dipropyl-N'-p-bromophenylguanidine as well as N-methyl-N-propyl-N'-m-trifluoromethylphenylguanidine.

The preparations fought the disease up to 75 to 96% in concentrations of 0.25% of the active ingredient.

The compounds used according to the invention can by treating appropriate arylthioureas, which are used in the form of isothiouronic salts are obtained with aliphatic amines.

The compounds mentioned can also be obtained either a) by condensation of the Monoarylcyanamides with hydrochlorides aliphatic

ι ο amines or b) by condensation of the dialkylcyanamides with hydrochlorides of aromatic amines. In this process, the step of producing the aromatic amine hydrochloride are combined with the stage of condensation.

The fungicides used according to the invention make it possible to attack both powdery mildew and gray mold To combat plants effectively; this allows the number of treatments as well as the effort involved To reduce preparations for combating the mentioned pathogens. A great asset of the The fungicides mentioned is also the fact that they can be easily obtained from an easily accessible raw material can be won.

Application example 1

The effectiveness of the preparations was tested in the greenhouse in combating powdery mildew that attack cucumbers (Erysiphe cichoracearum DC f-cucurbitacearum Pot. And Sphaerotheca fuliginea Poll. F. Cucurbitacearum Pot.). Plants with a few fully formed leaves were sprayed with suspensions of the preparations; After drying, the leaves were inoculated with the fungal conidia suspension at an infection rate of 200,000 conidia / cm ^3. Karathan served as a comparison standard. The experiment was repeated three times.

The test results of the compounds used in the form of 50% wettable powders are in the Tables I to VII given.

The concentrations given in the tables corresponded to the activity of the active ingredients.

As can be seen from Tables I and II, the N, N-dimethyl-N'-aryl-substituted guanidines have a high activity against powdery mildew fungi on cucumbers. The highest effectiveness was at

Ν, Ν-dimethyl-N'-m-chlorophenylguanidine,
Ν, Ν-dimethyl-N'-p-chlorophenylguanidine,
NN-dimethyl-NO ^ -dichlorophenylguanidine,
Ν, Ν-dimethyl-N'-p-bromophenylguanidine and
Ν, Ν-dimethyl-N'-m-trifluoromethylphenylguanidine

observed. The activity of these compounds was equal to or close to that of Karathan's.

The investigation of Ν, Ν-dimethyl-N'-aryl-substituted guanidine salts showed that they all have high activity against powdery mildew fungi on cucumbers (Table III). The dimethyldithiocarbamate and the picrate of Ν, Ν-dimethyl-N'-m-chlorophenylguanidine as well as the dimethyldithiocarbamate of N ₁ N-dimethyl-N'-m-trifluoromethylphenylguanidine showed an activity which was equal to or close to that of karathan.

never Ν, Ν-diethyl-N'-aryl-substituted guanidines showed a high effectiveness against powdery mildew fungi on cucumbers through concentrations of 0.05 to 0.2%, however, were weaker than Karathan (Table IV).

The N, N-dipropyl-N'-aryl-substituted guanidines

10

15th

showed high activity in the control of powdery mildew fungi on cucumbers. From the preparations of this Group came the Ν, Ν-Dipropyi-N'-m-trifluoromethylphenylguanidine close to Karathan effectiveness (Table V).

The N-methyl-N-alkyl-N'-aryl-substituted guanidines were highly active against powdery mildew on cucumber (Tables VI and VII). From them came

N-methyl-N-ethyl-N'-m-chlorophenylguanidine,
N-methyl-N-ethyl-N'-S ^ -dichlorophenyl-

guanidine,

N-methyl-N-propyl-N'-m-chlorophenylguanidine,
N-methyl-N-propyl-N'-m-trifluoromethyl-

phenylguanidine and
N-methyl-Nn-butyl-N'-m-chlorophenylguanidine

equal or close to the effectiveness according to the Karathan.
Application example 2

20th

One of the most active compounds - the N, N-dimethyl-N'-m-chlorophenylguanidine - was used in the fight against powdery mildew on apples (Jonathan variety) in the form of a 50% wettable powder examined. The preparation was in a concentration of 0.15% of the active ingredient compared to 90% Sulfur in a concentration of 0.45% of the active ingredient was tested as the standard. During one season six sprayings were carried out. The test results are given in Table VIII.

As can be seen from Table VIII, the Ν, Ν-dimethyl-N'-m-chlorophenylguanidine showed in the control of the powdery mildew fungus on apples is as effective as that of wettable sulfur, whereby the mentioned preparation was used in a concentration three times lower than that of sulfur.

Application example 3

The effectiveness of the preparations in combating gray mold (Botrytis fabae) in greenhouses was examined on beans of the »Russian Black« variety. Plants were used for the experiments, which had 7-8 pairs of well-developed leaves. the Preparations and captan as a comparison standard were tested in 0.25% concentration of the active ingredient Plants were initially sprayed with a suspension of the preparation. After the suspension had dried the plants were treated with a suspension of Botrytis fabae spores obtained from a pure, Fungal culture grown on oat agar, inoculated. The assessment of the disease that occurred was on Carried out the third day using the following method: The necroses on each leaf were on one Counted circular area with a diameter of 1.5 cm The percentage of disease control was then calculated using Abbott's formula. The test results are summarized in Tables IX to XIV

The examination of the N, N-dimethyl-N'-aryl-substituted Guanidines have shown that they are highly effective in combating Botrytis fabae in beans (Table IX). Of the preparations in this group, the Ν, Ν-dimethyl-N'-m-chlorophenylguanidine fought the disease as well as the captan.

As can be seen from the results in Table X, dimethyldithiocarbamate was found to have high activity des Ν, Ν-dimethyl-N'-m-chlorophenylguanidine observed when protecting beans against Botrytis fabae. This preparation was the activity according to the Captan soon. The methyl sulfate of N, N-dimethyl-N'-phenylguanidine was weaker than the captan (Table XI).

It can be seen from the results in Table XII that N, N-dipropyl-N'-phenylguanidine, N, N-dipropyl-N'-p-chlorophenylguanidine and N, N-dipropyl-N'-pbromophenylguanidine have high activity against botrytis fabae on beans, but were less effective than the captan.

N-methyl-N-ethyl-N'-p-chlorophenylguanidine, N-methyl-N-ethyl-N'-p-bromophenylguanidine and N-methyl-N-propyl-N'-m-trifluoromethylphenylguanidine showed activity close to that of captan (Tables XIII and XIV).

Table I.

Serial No. preparation
1 2

Concentration (%) Disease fight (%) 3 4th 0.025 70.0 0.05 73.0 0.1 82.0 0.2 90.0 0.025 50.0 0.05 68.0 0.1 70.0 0.2 80.0 0.025 79.0 0.05 93.0 0.1 97.0 0.2 100.0 0.025 87.0

1 Ν, Ν-dimethyl-N'-phenylguanidine

Methyl sulfate of N, N-dimethyl-N'-phenylguanidine

Ν, Ν-dimethyl-N'-o-chlorophenylguanidine

Ν, Ν-dimethyl-N'-m-chlorophenylguanidine

Continuation No. preparation 1 2

Concentration (%) Disease 93.0 fight (%) 97.0 3 4th 100.0 0.025 100.0 0.05 59.0 0.1 74.0 0.2 83.0 0.025 100.0 0.05 88.0 0.1 94.0 0.2 100.0 0.025 100.0 0.05 55.0 0.1 77.0 0.2 97.0 0.025 100.0 0.05 79.0 0.1 93.0 0.2 99.0 0.025 100.0 0.05 88.0 0.1 97.0 0.2 100.0 0.025 100.0 0.05 97.0 0.1 100.0 0.2 0.025 0.05

Ν, Ν-dimethyl-N'-p-chlorophenylguanidine

N, N-dimethyl-N'-2,5-dichloropheny! Guanidine

N, N-dimethyl-N'-3,4-dichlorophenylguanidine

N, N-dimethyl-N'-2,4,5-trichlorophenylguanidine

Ν, Ν-dimethyl-N'-p-bromphenyIguanidine

N, N-dimethyl-N'-m-trifluoromethylphenylguanidine

11 Karathan (standard)

Disease development in the sample 71%.

Table II

Serial No. preparation

Concentration (Vn) Disease 66.0 fight (%) 85.0 3 4th 100.0 0.025 100.0 0.05 67.0 0.1 79.0 0.2 93.0 0.025 98.0 0.05 87.0 0.1 96.0 0.2 0.025 0.05

1 N, N-dimethyl-N'-m-methylphenylguanidine

2 N, N-dimethyl-N'-p-methylphenyl guanidine

3 Karathan (standard) disease development in the sample 75%.

Table III

Serial No. preparation 1 2

Concentration (%) 3

Disease Control (%)

Ν, Ν-dimethyl-N'-m-chlorophenyIguanidine 0.025
0.05
0.1
0.2

85.0

97.0

98.0

100.0

Continuation of Lid. No. preparation 2

Concentration (%) Disease 89.0 fight (%) 96.0 3 4th 98.0 0.025 100.0 0.05 83.0 0.1 94.0 0.2 98.0 0.025 100.0 0.05 58.0 0.1 72.0 0.2 89.0 0.025 99.0 0.05 94.0 0.1 98.0 0.2 100.0 0.025 100.0 0.05 95.0 0.1 98.0 0.2 0.025 0.05

Dimethyldithiocarbamate of Ν, Ν-dimethyl-N'-m-chloro-

phenylguanidines

N.N-Dimethyl-N'-m -chlorophenylguanidine tetralhionate Ν, Ν-dimethyl-N'-m-chlorophenylguanidine picrate Dimethyldithiocarbamate of Ν, Ν-dimethyl-N'-m-trifluoro-

methylphenylguanidine

Karathan (standard)

Disease development in the sample 87%.

Table iV

Serial No. preparation 2

Concentration (%) Disease 59.0 fight (%) 63.0 3 4th 75.0 0.025 84.0 0.05 66.0 0.1 89.0 0.2 97.0 0.025 99.0 0.05 72.0 0.1 78.0 0.2 88.0 0.025 97.0 0.05 68.0 0.1 80.0 0.2 91.0 0.025 96.0 0.05 69.0 0.1 86.0 0.2 95.0 0.025 100.0 0.05 57.0 0.1 69.0 0.2 97.0 0.025 100.0 0.05 57.0 0.1 80.0 0.2 88.0 0.025 98.0 0.05 0.1 0.2

N, N-diethyl-N'-phenylguanidine Ν, Ν-diethyl-N'-m-chlorophenylguanidine hydrochloride N, N-Diethyl-N'-2,5-dichlorophenylguanidine N, N-Diethyl-N'-2,5-dichlorophenylguanidine hydrochloride N ^ -Diethyl-N'-S ^ -dichlorophenylguanidine hydrochloride N, N-Diethyl-N'-2,4,5-trichlorophenylguanidine N, N-Diethyl-N'-p-bromophenylguanidine

continuation preparation preparation preparation 12th Disease
fight (%) 76.0
88.0
94.0
99.0 56.0
69.0
80.0
96.0 21 33 056
11th Serial No. 2 2 2 4th 92.0
97.0 63.0
80.0
85.0
87.0 1 Ν, Ν-diethyl-N'-m-trinuormetliylphenylguanidine hydrochloride N, N-dipropyl-N'-phenylguanidine N-methyl-N-ethyl-N'-m-chlorophenylguanidine Concentration (%) 63.0
82.0
88.0
90.0 8th Karathan (standard) Ν, Ν-dipropyl-N'-m-chlorophenylguanidine 3 66.0
83.0
96.9
97.5 9 Disease development in the sample 75%. Ν, Ν-dipropyl-N'-p -chlorophenylguanidine 0.025
0.05
0.1
0.2 Disease
fight (%) 59.0
63.0
85.0
91.0 Table V N ^ -dipropyl-NO ^ -dichlorophenylguanidine 0.025
0.05 4th 55.0
74.0
82.0
93.0 Serial No. N, N-Dipropyl-N'-2,5-dichlorophenylguanidine 87.0
93.0
100.0
100.0 1 Ν, Ν-dipropyl-N'-p-bromophenylguanidine 96.0
100.0 : 1 Ν, Ν-dipropyl-N'-m-trifluoromethylphenylguanidine Concentration (%) 2 ['; 8 Karathan (standard)
; Disease development in the sample 87%. 3 Disease
fight (%) 3 £ Table VI 0.025
0.05
0.1
0.2 4th 4th jl serial No. 0.025
0.05
0.1
0.2 86.0
97.0
100.0
100.0 : 5 ti ' 0.025
0.05
0.1
0.2 6th i; 0.025
0.05
0.1
0.2 ;;: 7 0.025
0.05
0.1
0.2 0.025
0.05
0.1
0.2 0.025
0.05
0.1
0.2 0.025
0.05 Concentration (%) 3 0.025
0.05
0.1
0.2

21 33 056 13th preparation preparation 14th Disease 78.0 86.0 fight (%) 91.0 92.0 continuation 2 2 Concentration (%) 4th 100.0 98.0 Lld. No. N-methyl-N-ethyl-N'-p -chlorophenylguanidine N-methyl-N-propyl-N'-m -chlorophenylguanidine 100.0 100.0 3 68.0 82.0 1 0.025 84.0 91.0 2 0.05 100.0 98.0 N-M ethyl-N-ethyl-N'-2,5-dichloropheny! Guanidine N-methyl-N-propyl-N'-m-trifluoromethylphenylguanidine 0.1 100.0 100.0 0.2 92.0 57.0 0.025 97.0 70.0 3 0.05 100.0 87.0 N-methyl-N-ethyl-N '^^ - dichlorophenylguanidine N-methyl-N-isopropyl-N'-m -chlorophenylguanidine 0.1 100.0 92.0 0.2 79.0 85.0 0.025 85.0 93.0 4th 0.05 89.0 98.0 N-methyl-N-ethyl-N '^ AS-trichlorophenylguanidine N-methyl-N-n-butyl-N'-m -chlorophenylguanidine 0.1 96.0 100.0 0.2 68.0 93.0 0.025 77.0 98.0 5 0.05 94.0 N-methyl-N-ethyl-N'-p-bromophenylguanidine Karathan (standard) 0.1 100.0 0.2 73.0 Disease development in the sample 87.0%. 0.025 84.0 6th 0.05 92.0 N-methyl-N-ethyl-N'-m-trinuomethylphenylguanidine 0.1 97.0 0.2 57.0 0.025 66.0 7th 0.05 94.0 N-methyl-N-ethyl-N'-p-methylphenylguanidine 0.1 100.0 0.2 96.0 0.025 100.0 8th 0.05 Karathan (standard) 0.1 0.2 Disease Disease development in the sample 87%. 0.025 fight (%) 9 Table VII 0.05 4th Serial No. 1 Concentration (%) 1 3 0.025 0.05 2 0.1 0.2 0.025 0.05 3 0.1 0.2 0.025 0.05 4th 0.1 0.2 0.025 0.05 5 0.1 0.2 0.025 0.05

15th 16

Table VIII

Serial No preparation concentration

Damage to the shoots

Disease development

1 Ν, Ν-dimethyl-N'-m-chlorophenylguanidine

2 wettable sulfur (standard)

3 blank sample

0.15 8.0 4.0 0.45 10.0 5.0 - 16.0 13.0

Table IX

Serial No. preparation

concentration

Disease control

1 Ν, Ν-dimethyl-N'-m-chlorophenyIguanidine 0.25

2! ^, N-dimethyl-N '^ - dichlorophenylguanidine 0.25

3 Ν, Ν-diisopropyl-N'-phenylguanidine 0.25

4 Captan (standard) 0.25

Mean number of necroses in the sample 95.0 72.0 83.0 97.0

Table X

Serial No.

Preparation concentration

(K

Disease control

1 Dimethyldithiocarbamate des N, N-dimethyl-N'-nv 0.25 chlorphenylguanidines

2 Captan (standard) 0.25 Number of necroses in the sample 69.

89.0 91.0

Table Xl

Serial No.

Preparation concentration

Disease control

1 methyl sulfate of Ν, Ν-üimethyl-N'-phenylguanidine

2 Captan (standard)

Number of necroses in the sample 153.

0.25
0.25

64.0 77.0

Table XII

Serial No. preparation

concentration Disease prevention 030 243/63 0.25 75.0 0.25 75.0 0.25 82.0 0.25 92.0

1 Ν, Ν-dipropyl-N'-phenylguanidine

2 Ν, Ν-dipropyl-N'-p -chlorophenylguanidine

3 Ν, Ν-dipropyl-N'-p-bromophenylguanidine

4 Captan (standard)

Number of necroses in the sample 100.

18th

Table XIII

Serial Wr.

preparation

concentration

Disease control

1 N-methyl-N-ethyl-N'-p-chlorophenylguanidine 0.25

2 N-methyl-N-ethyl-N'-p-bromophenylguanidine 0.25

3 Captan (standard) 0.25

Number of necroses in sample 4C.

83.0
81.0
97.0

Table XIV

Serial No.

preparation

concentration

Disease control

1 N-methyl-N-propyl-N'-m-trifluoromethylphenylguanidine

2 Captan (standard)
Number of necroses in the specimen 72.

Compared to the known from FR-PS 15 41 647, substituted on all three nitrogen atoms guanidines The guanidines used according to the invention and unsubstituted on the imino group have a broader one Spectrum of activity, as they are not just as opposed to the products known from the aforementioned FR-PS Mildew, but also against gray mold

Table XV

0.25
0.25

65.0
75.0

30 work. In addition, they are much more active, as can be seen from the following Table XV , in which the fungicidal effect of the Ν, Ν-dimethyl-N'-m-chlorophenylguanidine used according to the invention compared to the effect of the N, N-dimethyl-N 'known from the French patent -mchlorphenyl-N "-methylguanidins in the fight against powdery mildew of the cucumber is contrasted:

Active ingredient

Active ingredient concentration (%) Combating powdery mildew in cucumber Disease control after n days (%) 15 20

Ν, Ν-dimethyl-N'-m-chlorophenylguanidine

Ν, Ν-dimethyl-N'-m-chlorophenyl-N "-methylguanidine

I 0.05 1 0.025

/ 0.05 I 0.025 100
98

65
54

99
95

30th
15th

98 87

0.0 0.0

The superior effectiveness of the substances used according to the invention compared to the known preparations karathan and colloidal sulfur has an effect in particular on the harvest results, as can be seen from the following Tables XVI and XVII , in which the above-mentioned, known preparations compared with three substances used according to the invention with regard to the effect Powdery mildew infestation are contrasted with the cucumber.

Table XVI

Combating powdery mildew of cucumbers (»Sputnik I« variety)

Effective attempt 3rd Sept attempt Oct 10 harvest in cent in% of Active ingredient focus % Infestation % Ill- % Infestation % Ill- in ner / ha Comparison tration continuity continuity g / plant value V. (%) schritl schritl 100% 0.025 212.2 121.65 N, N-dimethyl-N'-m- 0.050 29.60 8.46 30.00 10.50 332.6 245.5 i41.41 chlorphenylguanidine 0.025 25.25 8.00 26.25 11.50 386.6 209.4 120.62 N, N-dimethyl-N'-p- 0.05 31.39 10.02 33.53 13.32 329.8 241.7 139.23 chlorphenylguanidine 26.91 8.58 28.67 12.48 380.7

19th attempt 21 33 056 attempt 10. OkL 20th in cent in% of % Infestation % Infestation % Ill ner / ha Comparison continuation continuity harvest value V. Active ingredient 3rd Sept step in 100% Active ingredient focus % Ill g / plant 212.7 122.52 tration 28.17 continuity 29.14 10.05 246.5 141.99 (%) 23.84 step 24.75 8.89 0.025 334.9 203.8 117.41 N, N-dimethyl-N'-m- 0.05 26.09 8.35 32.50 15.25 388.2 76.6 44.11 trifluoromethyl 23.94 7.02 27.50 11.50 65.9 37.97 phenylguanidine 0.0125 2.1.67 6.25 2.25 321.0 202.8 116.83 Karathan 0.025 36.25 11.23 42.50 21.25 · 120.6 198.2 114.19 0.05 35.38 9.36 37.25 16.00 103.8 173.6 100.0 0.10 *) 79.68 2.00 98.75 45.75 319.4 Colloidal sulfur 0.15 *) 17.14 312.2 - 15.03 243.4 None 31.24 (Comparison values)

*) Concentration of the preparation.
Table XVII
Cucumber harvest when treated with various fungicides

Active ingredient Active ingredient Harvest in Number of fruits Medium fruit concentration g / plant per plant weight (%) (G)

Ν, Ν-dimethyl-N'-m-chlorophenyl- ί 0.05 1850.4

guadinin I 0.025 1782.0

Karathan 0.02 1544.8

Colloidal sulfur 0.1 1639.4

19.4
16.8

16.5
17.05

95.9 107.5

95.7 96.95

From the experiments shown in Tables XVI and XVH it can be seen that the harvest results obtained in the treatment of the plants with the agents used according to the invention are obtained considerably are higher than the plants treated with karathan or colloidal sulfur. In which Karathan preparation also makes itself even with the use of higher concentrations (0.025 and 0.05%) in an extremely drastic way the phytotoxicity in the form of a growth inhibition as well as the induction noticeable of leaf damage. The sulfur preparation also inhibits the applied effective ones Concentrations the growth of the plants.

This effect of the substances used according to the invention is all the more surprising as compared to it the fungal diseases against which the "Patent Schnellbericht", 1967, from the literature mentioned at the beginning, Ref. B 47-209 known, structurally quite similar substances are effective, no or only have moderate effectiveness.

In the following Tables XVIII to XX information on the effect of various substances according to the invention are given of the compounds used against the microorganisms listed in the cited literature reference listed.

The following Table XVIIl shows the effectiveness of Ν, Ν-dimethyl-N'-m-chlorophenylguanidine (C) against Alternaria of the tomato as well as against Erysiphe of the pumpkin indicated.

Table XVIII

Pathogens
Organisms

Trial Land Concentration

(g active substance per 100 1) effectiveness of the investigated
Compound (C) compared to that of standard fungicides

(Conc. In g of active substance per 1001)

Phytotoxicity

Alternaria the
tomato

Switzerland

75
50
25 C <Maneb (240)
C <Mancozeb (240)
C < Maneb (240)
( t Mancozeb (240)

C < Maneb (240)
C < Mancozeb (240)

no

continuation

Pathogens
Organisms

Trial country concentration

(g active substance per 100 l)

Effectiveness of the examined
Compound (C) compared to that
of standard fungicides

(Conc. In g of active substance per 1001)

Phytotoxicylate

Powdery mildew (Erysiphe)
of the pumpkin

Switzerland

75
50

25th

C > Benomyl (30)

C > Benomyl (30)
C> Dinocap (30)

C = benomyl (30)

no

From the values in Table XVIII it can be seen that the compound studied in terms of tomato alternaria versus conventional pesticides has a lower effectiveness, while it is extremely against the powdery mildew of the pumpkin is effective.

The following Table XIX summarizes experiments that were carried out with some according to the invention compounds used against Piricularia oryzae, another one in the above reference specified mushroom species.

20th

Table XIX

link % Active ingredient % Suppression focus of growth tration of Piricularia oryzae N, N-dimethyl-N'- 0.05 0 m-chlorophenylguanidine N-methyl-N-ethyl-N'- 0.05 0 3,4-dichlorophenyl guadinin N-methyl-N-propyl-N'- 0.05 0 m-trifluoromethyl- phenylguanidine Ediphenphos ι 0.05 100 (Standard) I.
(O-ethyl-SS-diphenyl-1
dithiophosphate) J 0.025
0.005 100
80

To carry out the experiments, rice plants in pots in the two-leaf state of growth were treated with 100 ml of an 0.1% suspension of the active substance. After the preparation had dried out, it was infected with a spore suspension. The results were ^{brought about at 27 °} C. and a relative humidity of 98 to 100%, the infestation of the leaves being assessed and then an average assessment result shown in Table XX

was formed.

Also in the following Table XX are various known and used according to the invention Compounds have been examined for their effectiveness against various phytopathogenic fungi, which also included the anthracnose pathogen of the cucumber (Colletotrichum lagenarium). For comparison the effectiveness against gray mold is also listed.

link

Ν, Ν-dimethyl-N'-p-bromophenylguanidine
Ν, Ν-dimethyl-N'-m-chlorophenylguanidine

N-methyl-N-ethyl-N'-3,4-di-0.01
chlorophenylguanidine

Active ingredient oppression of mycelial growth Vent,
inaeq. from Colletu-
trich.
lay. Xanthomonas
malvac conc.
(%) Botrytis
cinerea
(Gray
Mould) Foot
mon. 11.6 Asper,
Niger 3.2 18.6 0.01 86.5 12.5 14.8 13.8 0.0 9.2 0.01 100.0 7.3 7.0 10.3 5.4 6.3 ■ 0.01 88.8 22.5 12.5

continuation WirkstolT- 21 33 056 Foot Vent. 24 from CoIIcIo- Xiinthomonas 23 link conc. mon. inaeq. Asper. irich. ma I \ ac nigcr lay. <%) 8.2 12.5 8.1 0.0 0.01 9.7 N.N-diethyl-N '^ AS-lrichlor- Mycelium growth suppression 0.0 6.2 0.0 7.2 phenylguanidine 0.01 Bolrytis 11.6 Ν, Ν-DiisopropyI-N'-phenyl- cincrca 100 0 QS η 84.6 guanidine 0.0! (Gray 100 π 100.0 Phygon (standard) 0.01 Mould) Zineb (standard) 80.4 87.4

To carry out the experiments summarized in Table XX, the preparations were dissolved in acetone and placed in liquefied glucose / potato agar, after which the whole thing was poured out into petri dishes. A day later the inoculation of the

Agar dishes with the mushrooms by injection leads. After five days of incubation in a thermostat at 24 ° C, the diameter of the fungal colonists became determined and the percentage of oppression de; Mycelium growth calculated using Abbot's formula.

Claims (1)

Claims: 1. Use of compounds of the general a formula ^> - NH- C— n ' NH R ' wherein