DE1145418B - Contact fungicide and acaricide pesticides - Google Patents

Description

GERMAN

PATENT OFFICE

F 30935 IVa / 451

REGISTRATION DATE: 6. A P R I L 1960

NOTICE THE REGISTRATION AND ISSUE OF THE EDITORIAL: MARCH 14, 1963

From the German Auslegeschrift 1 079 381 are compounds with systemic fungicidal action based on nitrogen-containing sugar derivatives known.

In the further processing of this area it has now been found that higher AlkyHST-glycosides of general formula

Z —N —Ri

I.
R ₂

in which Z means a reducing sugar residue from the series of mono- and disaccharides, Ri for a higher alkyl radical with 10 to 18 carbon atoms and R2 for hydrogen or a lower alkyl radical stands to have a real fungicidal and also acaricidal effect, while the systemic effect - probably due to the long alkyl residues - disappears.

The higher alkyl-N-glycosides are after known processes (Am. Soc., 73, p. 1976 [1951], and 77, p. 2839 [1955]) by condensation of Gaining sugar with higher fatty amines.

Suitable sugars are, for example, arabinose, xylose, glucose, glucosamine, fructose, galactose, Maltose and lactose.

The compounds can be used alone or together with other crop protection agents with the addition suitable auxiliary and inert materials are used.

US Pat. No. 2,808,402 describes the preparation of N-sorbityl carbamates by reaction of an alcohol with the cyclic urethane of an N-alkyl-N-sorbitylcarbamic acid described, this in turn by the reaction of an N-alkylglucamine with urea. The named process products should according to the information of cited U.S. patent specification have fungicidal properties.

When reworking Example 1, however, it was found that the values of the elemental analysis for the reaction product (allegedly an N-methyl-N-sorbityldodecylcarbamate) also matched the cyclic urethane of N-methyl-N-sorbitylcarbamic acid used as the starting material very well.

No analytical values for the reaction product allegedly obtainable according to Example 1 are listed in the aforementioned patent specification. The melting point of the latter is virtually identical to the starting material (146 to 149 ° C or 145 to 148 ⁰ C). In the other examples of US Pat. No. 2,808,402, there is no longer any information whatsoever which characterizes the contact fungicides and acaricidal pesticides

Applicant:

Paint factories Bayer Aktiengesellschaft, Leverkusen

Dr. Engelbert Kühle, Cologne-Stammheim,

Dr. Richard Wegler, Leverkusen,

Dr. Victor Flück, Basel (Switzerland),

Dr. Ferdinand Grewe, Cologne-Stammheim,

and Dr. Günter Unterstenhöfer, Opladen,

have been named as inventors

driving products could serve, so that an exact reworking is not possible.

For this reason, the above-mentioned cyclic urethane became N-methyl-N-sorbitylcarbamic acid in comparison to the N-alkylglucosides to be used according to the invention on its fungicidal and acaricidal effectiveness tested. The values obtained from the relevant comparative tests can be seen in the table below:

Comparative experiments

compared to the compounds known from US Pat. No. 2,808,402

a) Fungicidal effect when used against Phytophthora infestans on tomatoes

link

Cycl. N-methylsorbitylcarbamic acid urethane (USA patent

2 808 402)

N-dodecyl glucoside (according to the invention)

Control (untreated)

Degree of infestation in one

Active ingredient concentration of

0.0125%

100

24 100

0.0031%

100

71 100

309 539/407

b) acaricidal activity against the spider mite Tetranychus telarius (green form)

after 48 hours

link

Cycl. N-methylsorbitylcarbamic acid urethane (U.S. Patent / 2,808,402) j

N-dodecylgalactoside (fiction f according to) "j

0.2 0.05 0.2 0.5

Mortification

the

Pests i% decylglucoside) by an excellent effect against both fungi and mites.

example 1

Fungicidal effect of various N-dodecyl glycosides on Phytophthora infestans on tomatoes

100 100

link

From the test results reported above, it can be seen that the cyclic urethane of N-methyl-N-sorbitylcarbamic acid when used against Phytophthora infestans (fungicidal effect) as well as against Tetranychus telarius (acaricidal Effectiveness) proves to be completely ineffective. Compared to US Pat. No. 2,844,505 The pesticides according to the invention are distinguished as phenylosazone which is described as having fungicidal activity also characterized by a clear technical superiority. The results of the related Comparative tests are compiled in the following table:

Comparative experiments

compared to those from the LTSA. patent 2,844,505 known compounds

a) Fungicidal effect when used against Phytophthora infestans on tomatoes N-dodecyl glucoside ...

N-dodecyl galactoside.

N-dodecyl maltoside ..
N-dodecyl fructoside ..

Comparative agent (zinc ethylene bis dithiocarbamate)

control

Infestation level at a preparation concentration of

0.05%

0.2 0.4 0.2

100

0.0125%

14th

10

33

9 100

0.0031%

55 100

Example 2

Acaricidal effects of various N-dodecyl glycosides on the spider mite T. telarius

(green shape)

link

N-dodecyl galactoside
N-dodecyl maltoside.
N-dodecyl lactoside ..

Aqueous emulsion

in a concentration of

0.2 O / o O, O 50 / o

100 100 100

100

link

Glucose phenylosazone (USA.

Patent 2844505)

N-dodecyl glucoside (invention

according to)

Control (untreated)

Degree of infestation at an active ingredient concentration of 0.1%

The numbers represent the percent kill after 48 hours.

Example 3

Fungicidal effect of N-dodecyl glucoside when used against leaf-parasitic fungi

on various crops

100

0 100

Application against

b) acaricidal activity against the spider mite Tetranychus telarius (green form)

after 48 hours at one drug concentration

of 0.2%

Colletotrichum lind, on beans

Preparation concentration

in 0/0

0.05

0.025

0.0125

0.1

0.05

Infestation level

33 16 31

link

Glucose phenylosazone (US patent 2844505)

N-dodecyl glucoside (according to the invention)

Mortification

the pests

i%

0 100 Fus. Lycopersici on tomatoes ... Omphalia flavida on Coleus *). Omphalia flavida on coffee *).

*) Active ingredient formulation brushed onto the underside of the leaf.

Example 4

Fungicidal effects of various N-alkyl glycosides when used against Phytophthora infestans on tomatoes

link

As can be seen from the results of comparative tests compiled in the above table, is

the 65 known from the USA patent specification 2 844 505

Phenylosazon of glucose both fungicidal and N-tetradecylglucoside ...

acaricide ineffective. In contrast, the N-Tetradecylgalactosid ..

Compound to be used according to the invention (N-Do-N-dodecyl-xyloside

Infestation level at a preparation concentration of

0.1%

1 0 0.4

0.025%

25 8 5

0.00625%

45 27 26

link

N-methyl-N-stearyl glucoside

N-methyl-N-dodecyl glucoside

N-methyl-N-dodecyl galactoside

N-dodecyl arabinoside ...

Comparative agent (zinc ethylene bis dithiocarbamate)

Control (untreated)

Infestation level at a preparation concentration of

0.1 "/" I 0.025 "/" 0.00625 "/"

11
0.2

0.9
0.2

4th
100

11
100

45 100

Claims (1)

PATENT CLAIM: Contact fungicides and acaricidal pesticides containing higher alkyl-N-glycosides of the general formula Z —N —Ri R ₂ wherein Z is the remainder of a reducing sugar from the series of mono- and disaccharides, Ri is an alkyl radical with 10 to 18 carbon atoms and R2 denotes hydrogen or a lower alkyl radical. Considered publications:
U.S. Patent Nos. 2,808,402, 2844505.