DE2133056B2 - Use of NJS-di-alkyl-N'aryl-substituted guanidines for combating powdery mildew and gray mold on plants - Google Patents

Description

X ₁ Y

and Z: H ₁ CI ₁ Br or CF ₃

mean, or the general formula X

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 SCV, (CH ₃ ) ₂ - NCSS ', S ₄ O ₆ "or C ₀ H ₂ (NOj) ₃ O 'means, if appropriate with a carrier for combating powdery mildew and gray mold on plants

N.N-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'-3,4-dichlorophenyI-

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

phenylguanidins or
N ₁ N- dimethyl- N '-m-chlorophenylguanidine-

tetrathionate
according to claim 1.

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

It is known that inorganic sulfur preparations are used to combat powdery mildew. The sulfur preparations, which have a high level of effectiveness against powdery mildew, also have negative properties. You can damage the plants, are not sufficiently effective in an air temperature below 2O ⁰ C and overall have only a weak fungicidal activity.

The »ICarathan« (2,4-dinitro-6-sec.-olaylphenylcrotonate) 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.

Next is the use of the preparation »Euparen« (N.N-Dimethyl-N'-phenyl-fN'-fluorodichloromethyij-thiosulfamid) 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. ScL, Vol. 44, p. 81, 1969) about the inhibiting effect of the preparation »Euparen« on Sphaerotheca achemillae. That is also known Use of "captan" (N-trichloromethylmercapto ^ -cyclohexane-l ^ -dicarboximide) and of "difolatane" (N-1,1,2,2-tetrachloroethylmercapto-4-cyclohexene-1,2-dicarboximide) 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

ArNHCNRR "

I!

NO

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.

Of 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 Insect fungicides and those in which R 'also denotes hydrogen, from patent quick report Part B 1967, Ref. B 47-209 as fungicides against anthracnose of cucumber, Alternaria kikuchiana of pear and various health diseases known.

It is therefore the object of the invention. Fungicides too determine which are easy to manufacture and, above all, at the same time are highly effective Have powdery mildew and Boirytis (gray mold) mushrooms.

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

R: CH ₃ , C ₂ H ^ n-CiH ₇ or! -C ₃ H ₇ ,

R ': CH ₃ , CiH ₅ , n-CjH ₇ , iC ₃ H ₇ or nC ₄ H ₉ and

X, Y

and Z: H, C), Br or CF ₃

mean, or the general formula X

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 ₄ ', (CH 3) 2-NCSS', S ₄ O ₆ "or C ₆ H ₂ (NO ₂ ) SO 'means, optionally 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 dimethyldithiccarbamates of

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

the tetrathionate of

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

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

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

guanidine or
N-methyl-Nn-butyl-N'-3,4-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:

N.N-Diiinuliji-N'-m -chlorophenylguanidine; the dimethyldithiocarbamate

N ₁ N-dimethyl-N'-m-chlorophenylguanidines; the methyl sulfate des

N, N-dimethyl-N'-pheny [guanidine; Ν, Ν-Dipropyl-N'-p-bromophenylguanidine and 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 Isoihiouronsalze, are obtained with aliphatic amines.

The compounds mentioned can also be obtained either a) by condensation of the Monoarylcyanamides with hydrochlorides of aliphatic 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 VH are 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 exhibited a high activity against powdery mildew fungi on cucumbers. The highest effectiveness was at

N, N-dimethyl-N '
N, N-dimethyl-N '
N, N-dimethyl-N '
N, N-dimethyl-N '
Ν, Ν-dimethyl-N '
guanidine

-m-chlorophenylguanidine,
p-chlorophenylguanicin,
-3,4-dichlorophenylguanidine,
-p-bromophenylguanidine and
m-trifluoromethylphenyl-

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 NN-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.

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

20th

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

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

N-methyl-N-ethyl-N'-m-chlorophenylguanidine,
N-methyI-N-ethyI-N'-3,4-dichlorophenyl-

guanidine,

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

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

equal or close to the effectiveness according to the Karathan.

Application example 2

One of the most active compounds - the N, N-dimethyl-N'-m-chlorophenylguanidine - was used in the control of powdery mildew on apples (variety Jonathan) 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 used in 0.25% concentration of the active ingredient tested. the 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, mushroom culture grown on oat agar, inoculated. The assessment of the occurring disease 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. After that was the percentage of disease control calculated according to Abbott's formula. The test results are summarized in Tables IX to XIV.

Examination of the N, N-dimethyl-N'-aryl-substituted guanidines showed that they were highly effective in the Control of Botrytis fabae of the beans own (Table IX). Of the preparations of this group fought the Ν, Ν-dimethyl-N'-m-chlorophenylguanidine the disease as well as the captan.

As can be seen from the results in Table X, dimethyldithiocarbamate was found to have high activity of N.N-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 Ν, Ν-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 XII! and XIV).

Table I.

Lrd. No. preparation
1 2

Concentration (%) Disease back-vaccination ('Ί.) 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

N, N-dimethyl-N'-pheny! Guanidine

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

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

N, N-I) imct hy l-N'-m-chlorophcny! Guanidine

! ■ 'place setting

I.I'd. No. Priiparal

I 2

N, N -dimethyl-N'-p-chlorophyny-guanidine

N.N-Dimethyl-N '^^ - dichlorophynylguanidine

! ^, N-dimethyl-NO ^ -dichlorophenylguanidine

N, N-dimethyl-N'-2,4,5-lrichlorophenyl-guanidine

N, N-dimethyl-N'-p-bromopheny! Guanidine

N.N-Dimethyl-N'-m-trifluoromethylphenylguanidine

11 Karathan (standard)

Disease development in sample 71 "

Table II

Con / cntralion (%) Sickness 93.0 fight (%) 97.0 .1 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

Lld. No. preparation 1 2

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

2 N.N-dimethyl-N'-p-methylphenylguanidine

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

Table II!

concentration ("· ..) 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

Serial No. preparation 1 2

Concentration (%) Disease 85.0 fight (%) 97.0 3 4th 98.0 0.025 100.0 0.05 0.1 0.2

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

Kortsot / ung

Lld. No. preparation

2

Dimethyldilhiokarbaniat des N.N-Dimethyl-N'-m-chloro-

phenylguanidines

N.N-Dimethyl-N'-m-chlorophynylguanidine tetruihionate N.N-dimethyl-N'-m-chlorophenylguanidine picnil Dimethyldithiocarbamate of N, N-Dimethy! -N'-m-trifluor-

methylphenylguanidine

Karathan (standard)

Disease development in the sample was 87%.

Concentration (%) Disease 89.0 hckiimpfuni! ("«) 96.0 } 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

Table IV

N, N-diethyl-N'-phenylguanidine N ^ -diethyl-N'-m -chlorophenylguanidine hydrochloride N ^ -Diethyl-N '^^ - dichlorophenylguanidine N ^ -Diethyl-N '^^ - dichlorophenylguanidine hydrochloride N, N-diethyl-N'-3,4-dichloφhenylguanidinhydΓochlorid N ^ -diethyl-N'-IAS-trichlorophenylguanidine N, N-diethyl-N'-p-bromophenylguanidine

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

T ^
; ■ '.; continuation 21 33 056
11th preparation
2 12th Disease
qualification (%)
4th | ^: LIiI. No.
'' ■ ' 1 N ₁ ND iuthyl-N'-m-trifiuomicthylphenylguanidine hydrochloride
Karathan (standard) Concentration (%)
i 76.0
88.0
94.0
99.0
92.0
97.0 : · 8th
\: \ 9 0.025
0.05
0.1
0.2
0.025
0.05

Disease development in the sample 75%.

LITI. No. preparation 1 2

1 Ν, Ν-dipropyl-N'-phenylguanidine

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

3 Ν, Ν-DipropyI-N'-p -chlorophenylguanidine

4 N ^ -dipropyl-N'-S ^ -dichlorophenylguanidine

5 N ^ -dipropyl-N'-Z ^ -dichlorophenylguanidine

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

7 Ν, Ν-dipropyl-N'-m-trinuomethylphenylguanidine

8 Karathan ^ Standard) Disease development in the sample 87%.

Table VI

Concentration (%) 3

Disease Control (%)

0.025 56.0 0.05 69.0 0.1 80.0 0.2 96.0 0.025 63.0 0.05 80.0 0.1 85.0 0.2 87.0 0.025 63.0 0.05 82.0 0.1 88.0 0.2 90.0 0.025 66.0 0.05 83.0 0.1 96.9 0.2 97.5 0.025 59.0 0.05 63.0 0.1 85.0 0.2 91.0 0.025 55.0 0.05 74.0 0.1 82.0 0.2 93.0 0.025 87.0 0.05 93.0 0.1 100.0 0.2 100.0 0.025 96.0 0.05 100.0

Serial No. preparation 1 2

Concentration (%) 3

Disease Control (%)

N-methyl-N-ethyl-N'-m-chlorophenylguanidine

0.025 86.0 0.05 97.0 0.1 100.0 0.2 100.0

13th

IOltSCt / Ullil Ll'd. No. preparation

I 2

2 N-methyl-N-iithyl-N'-p -chlorophenylguanidine

3 N-methyl-N-ethyl-N '^ S-dichlorophenylguminidine

4 N-methyl-N-ethyl-N '^^ - dichlorophenylguanidine

5 N-methyl-N-a'thyl-N '^ AS-trichloropheny! Guanidine

6 N-methyl-N-ethyl-N'-p-bromophenylguanidine

7 N-methyl-N-ethyl-N'-m-trifluoromethylpheny! Guanidine

8 N-methyl-N-ethyl-N'-p-methylphynylguanidine

9 Karathan (standard) disease development in the sample 87%.

Table VII

Serial No. preparation

1 14

Concentration <". '..)
3

Disease control ("..)

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
0.1
0.2

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 ("»)

78.0

91.0

100.0

100.0

68.0

84.0

100.0

100.0

92.0

97.0

100.0

100.0

79.0 85.0 89.0 96.0 68.0 77.0 94.0 100.0

73.0 84.0 92.0 97.0

57.0

66.0

94.0

100.0

96.0 100.0

Disease control <\.)

1 N-methyl-N-propyl-N'-m -chlorophenylguanidine

2 N-methyl-N-propyl-N'-m-irifluoromethylphenylguanidine

3 N-methyl-N-isopropyl-N'-m -chlorophenylguanidine

4 N-methyl-N-n-butyl-N'-m -chlorophenylguanidine

5 Karathan (standard) disease development in the sample 87.0%.

0.025
0.05
0 ,!
0.2

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

86.0

92.0

98.0

100.0

82.0 91.0 98.0 100.0 57.0 70.0 87.0 92.0

85.0

93.0

98.0

100.0

93.0 98.0

15th

16

Table VIII

LIu. No. preparation

Concentration damage to the shoots

Disease development

Ν, Ν-dimethyl-N'-m-chloropheny! Guanidine 0.15
Wettable sulfur (standard) 0.45

Blank sample

8.0 4.0 10.0 5.0 16.0 13.0

Table IX

Ltd. No. preparation

concentration

Disease control

N.N-Dimethyl-N'-m -chlorophenylguanidine 0.25

N, N-dimethyl-N'-3,4-dichloropheny! Guanidine 0.25

N, N-diisopropyl-N'-phenylguanidine 0.25

Captan (standard) 0.25

Mean number of necroses in sample 37.

95.0 72.0 83.0 97.0

Table X

Lld. No. preparation

concentration

Disease control

1 Dimethyldithiocarbamate des N.N-Dimethyl-N'-m-0.25 chlorphenylguanidines

2 Captan (standard) 0.25

Number of necroses in the specimen 69.

89.0 91.0

Table XI

Serial No.

preparation

1 N, N-dimethyl-N 'methyl sulfate
phcnylguanidins

2 Captan (standard)
Number of necroses in the specimen 153.

concentration

Illness reporting

64.0 77.0

Table XII

Serial No.

preparation

concentration Disease control 030 110/78 0.25 75.0 0.25 75.0 0.25 82.0 0.25 92.0

N, N-Dipropyl-N'-pheny! Guanidine

N, N-dipropyl-N'-p -chloropheny! Guanidine

Ν, Ν-DipropyI-N'-p-bromophenylguanidine

Captan (standard)

Number of necroses in the sample KK)

Table XlU

Serial No.

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 the sample 40.

83.0 81.0 97.0

Table XIV

Serial No.

preparation

concentration

Disease control

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

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

0.25
0.25

65.0 75.0

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

works. In addition, they are much more active as can be seen from the following Table XV, in which the fungicidal effect of the N.N-dimethyl-N'-m-chlorophenylguanidines used according to the invention of the effect of the N, N-dimethyl-N'-mchlorphenyl-N "-mcthylguanidins known from FR-PS in combating of powdery mildew is juxtaposed with cucumber:

Active ingredient

Effective concentration (%) Control of the meal louse of the cucumber

Disease regression after n days (%) 10 15 20

N, N-dimethyl-N'-m-chloropheny! Guanidine

Ν, Ν-dimethyl-N'-m-chloro-phcnyl-N "-methylguanidine

(TI ΙΊ f ^ IfIl I "1 I 0.05 100 99 98 gUdlllUM I 1 0.025 98 95 87 -N "- I 0.05 65 30th 0.0 1 0.025 54 15th 0.0

The superior effectiveness of the substances used according to the invention compared to the known ones Preparations Karathan and colloidal sulfur have an effect especially on the harvest results the following Tables XVI and XVII can be seen in which the named, known used Preparations of three substances used according to the invention with regard to their action against powdery mildew at the cucumber are juxtaposed.

Table XVI

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

Potato Attempt 3. Sept attempt K). Oct HmIe in cent in% of Active ingredient focus % HcIaII % Ill ;, BeIaII % Ill- in ner / ha Comparison trution continuity hcitslbrl- g / plant / .c value v. (%) step step 100% 0.025 212.2 121.65 N, N-Di me thy I-N'-m- 0.050 29.60 8.46 30.00 10.50 332.6 245.5 141.41 chlorphenylguanidine 0.025 25.25 8.00 26.25 11.50 386.6 209.4 120.62 N, N-dimethyl-N'-p- ö, 05 31.39 10.02 33.53 13.32 329.8 1JV, ZJ c hiorpheny! guanidine 26.9 i 8.58 28.67 IZ, Hö JfSU, /

19th attempt 21 33 056 attempt 10. OkL 20th in cent in% of % Infestation % Infestation % Ill- ner / ha Comparative continuation continuity harvest value v. Active ingredient 3rd Sept screams in 100% Effective focus % Ill g / plant 212.7 122.52 traiion 28.17 continuity 29.14 10.05 246.5 141.99 (%) 23.84 shrill 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 21.67 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 35.88 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 concentration harvest in
g / plant

Ν, Ν-dimethyl-N'-m-chlorophenyl- I 0.05

guadinine 1 0.025

Karathan 0.02

Colloidal sulfur 0.1

From the experiments shown in Tables XVI and XVII 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

Number of fruits Middle fruit per plant weight (G) 19.4 95.9 16.8 107.5 16.5 95.7 17.05 96.95

1850.4
1782.0
1544.8
1639.4

the fungus, against which the from the beginning mentioned reference "Patent Schnellbericht", 1967,

4ii Ref. B 47-209 known, structurally entirely similar substances are effective, have no or only moderate effectiveness.

In the following Tables XVIII to XX information about the effect of various inventive > proportion of the compounds used against the microorganisms listed in the cited literature listed.

The following Table XVIII shows the effectiveness of Ν, Ν-dimethyl-N'-m-chlorophenylguanidine (C)

^r ) 0 stated compared to Alternaria of the tomato and compared to Erysiphe of the pumpkin.

Table XVIII

Pathogcnc
Organisms

Target country concentration

(g active substance per 100 l)

Alternaria the
tomato

Switzerland

75 50 25

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

(Conc. In g of active substance per 1001)

Phytotoxicity

C <Some (240)
C <Mancozeb (240)

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

no

continuation

Palhogcne
Organisms

Target country concentration

(g active substance per 100 l)

Powdery mildew (Erysiphe)
of the pumpkin

Switzerland

75
50

25th

Effectiveness of the unlersuchlen
Compound (C) in comparison / u Ucr
from standard lungi / idcn

(Conc. In g active subslan / per K) OIi

l'hvKitoxi / iiiit

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 tested was effective for Alternaria the tomato is less effective than conventional pesticides, while it is extremely effective against pumpkin powdery mildew.

In the following Table XIX are experiments summarized that with some compounds used according to the invention against Piricuiaria oryzae, a further species of fungus listed in the above reference.

Table XlX

link

"/., Active ingredient- '/,' pressure suppression
concentrated growth

tration of Piricuiaria

orvzac

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

N-methyl-N-ethyl-N'-

3,4-dichlorophenyl

guadinin

N-methyl-N-propyl-N'-

m-trifluoromethyl-

phenylguanidine

Ediphenphos
(Default)

(O-ethyl-S ^ -diphenyldithiophosphate)

100

100

80

To carry out the experiments, rice plants in pots in the two-leaf state of growth were with Treated 100 ml of a 0.1% suspension of the active substance. After the preparation has dried out an infection with a spore suspension was carried out. The results were at 27 ° C and a relative humidity of 98 to 100% brought about, with the attack on the leaves assessed and then an average valuation result

was formed.

In the following Table XX there are also several known compounds used according to the invention for their effectiveness against various Phytopathogenic fungi have been investigated, including the causative agent of the anthracnose Cucumber (Colletotrichum lagenarium). For comparison is the effectiveness against gray mold also listed.

Table XX Effectori- oppression of mycelial growth Vent. from Colleto Xanlhomonas link conc. Botrytis l ^r us. inaeq. Asper. trich. malvac cincrea mon. Niger lay. (Gray (%) Mould) 11.6 3.2 18.6 0.01 86.5 12.5 13.8 Ν, Ν-dimethyl-N'-p-bromo- 14.8 0.0 9.2 phcnylguanidine 0.01 100.0 7.3 10.3 N, N-dimethyl-N'-m-chloro- 7.0 5.4 6.3 phcnylguanidine 0.01 88.8 22.5 12.5 N-methyl-N-ethyl-N'-3,4-di-

chloropheny! guanidine

Fortsctziini!

link Effective oppression of the mycelial growth \ 'cnl. from Collcto- Xanthomone; kon /. Uotrvtis Into the. inacq. Asper. irich. ma I vac cinerea mon. Niger lay. (Cirau- ("■ ·) sky) 12.5 8.1 0.0 N.N-diethyl-N '^ AS-trichlor- 0.01 80.4 8.2 9.7 phenylguanidine 6.2 0.0 7.2 Ν, Ν-diisopropyl-N'-phenyl- 0.01 87.4 0.0 11.6 guanidine 95.0 84.6 l'hygon (standard) 0.01 100.0 100.0 100.0 Zineb (standard) 0.01

To carry out the agar dishes with the fungi together in Table XX by injection

In all experiments, the preparations were dissolved in acetone. After five days of incubation in the thermostat be

and in liquefied glucose / potato agar -> o 24 ⁰ C the diameter of the mushroom colonies

brings, after which the whole is determined poured out in Petri dishes and the percentage of suppression de:

became. One day later, the inoculation of the mycelial growth was calculated using Abbot's formula.

Claims (1)

Patent claims: 1. Use of compounds of the general formula wherein R:
R ': CH ₃ , C ₂ Hk nC ₃ H ₇ or iC ₃ H ₇ , CH ₃ , C ₂ H ₅ , nC ₃ H ₇ , iC ₃ H ₇ or