DE1148409B - Fungicides - Google Patents

Description

GERMAN

PATENT OFFICE

B 59916 IVa / 451

REGISTRATION DATE: OCTOBER 29, 1960

NOTICE
THE REGISTRATION
AND ISSUE OF THE
EDITORIAL: MAY 9, 1963

It has been found that carbamic acid esters of the formula

Fungicides

O
NH-CO-CH ₂ -C =

L-CHY-

CHY-CH ₃ applicant:

Badische Anilin- & Soda-Fabrik ίο Aktiengesellschaft, Ludwigshafen / Rhein

in which X is hydrogen or one or more identical or different optionally substituted alkyl, Cycloalkyl, alkoxy or alkoxyalkyl radicals or halogen, cyano or nitro radicals and «= 1, 2 or 3 and Y signifies chlorine or bromine, have excellent fungicidal properties.

Highly effective aliphatic substituents X are z. B. methyl, ethyl, isopropyl, benzyl, butyl, Cyclohexyl, cyanomethyl, chloromethyl or methoxymethyl groups. These groups and also the Cyano and nitro groups, as well as chlorine and bromine atoms, can each be in the different Positions to the amino group on the aromatic radical. Alkyl groups with up to 6 carbon atoms are preferred.

The active ingredients are produced analogously to known methods, e.g. B. by implementing the Chloroformic acid halides or esters with the corresponding amines or by reacting the corresponding isocyanates with z. B. 4-chloropentine- (2) -ol- (l) or the corresponding ureas with z. B. 4-chloropentine- (2) -ol- (l).

The compounds mentioned have a broad spectrum of fungicidal activity and can be used for control the most diverse mushrooms are used, in particular because the compounds are through are characterized by good leaf tolerance, also for combating those fungi that grow on above-ground parts of plants Cause diseases, e.g. B. Plasmopara viticola (downy powdery mildew), red burner, Phytophthora in potatoes and tomatoes, or Fusicladium.

The active ingredients can be added in the usual way by adding extender, solvent, emulsifier or other aids, e.g. B. wetting agents or adhesives, to suspensions, solutions, emulsifiable concentrates, Litter or dust powders or dressings are worked up and used in these forms will. You can also contact Dr. Gustav Steinbrunn, Schwegenheim, Dr. Erich Flickinger, Ludwigshafen / Rhine, Dr. Herbert Stummeyer, Mannheim, and

Dr. Ernst-Heinrich Pommer, Ludwigshafen / Rhine,

have been named as inventors

.2

be used with other plant protection products.

The following example shows the excellent fungicidal effectiveness of the new compounds emerged.

example 1

Leaves of potted vines of the Müller-Thurgau variety are sprayed with aqueous dispersions containing 80% active ingredient and 20% sodium lignosulfonate in the dry matter. 0.015, 0.03, 0.06 and 0.125% strength spray liquors (based on the dry substance) are used. After the spray coating has dried on, the leaves are infected with a zoospore suspension of Plasmopara viticola. The plants are then first for 16 hours in a water vapor saturated (wet) chamber at 20 ° C and then eight days are placed in a greenhouse at temperatures of 20-30 ⁰ C. After this time, the plants for the acceleration and strengthening of the sporangium-outbreak again placed in the humid chamber for 16 hours. Then the spore beds on the underside of the leaves are counted. Untreated, infected control plants serve as a comparison.

309 579/274

Active ingredient
R-COO-CH ₂ -C = C-CHCI-Ch ₃ % infected E
* = 0.015 leaves after spray
0.031 ■ with *% iger
0.063 Active ingredient broth
0.125 Control (untreated) 100 100 100 100 _R <> HH 77.4 27.3 0 0 *) R === <(~~ \ - NH 25.0 10.0 0 *) 0 *) Cl R = Cl ^ ^) - NH 1.1 0 0 *) 0 *) 1.2 0 0 0 Cl 10.7 1.2 0 0 CH ₃ R = H ₃ C ^ ^ NH 2.3 0 0 0 Cl 1.0 1.2 0 0 NO ₂ CH ₃
I. K = HC ^] j ^ NH 0 ■ '■ ='; 0 0 0 CH ₃

*) Minor leaf damage. _. . , _

Example 2

The following experiments were carried out in the manner described in the previous example.

Effect against vine perenospora

Active ingredient ° / o infected leaves after spraying with *% iger ^ 0.031 0.063 active ingredient broth * = 0.015 100 100 0.125 Control (untreated) 100 86 83 100 <^ ~ NN-COO-CH ₂ -G = CH 100 31 I.
H (German interpretation document 1017 407)

Active ingredient % infected leaves after spraying with *% A 0.031 0.063 Active broth * = 0.015 33 33 0.125 <^ _ _N _coo-ca-ccH 74 10 Cl ^H (German interpretation document 1 017 407) 12th 1.5 <(^> - N-COO-CH ₂ -C = C-CHCl-CH ₃ 27 0 / ^ w
Cl ^Ά 19th 4th / ^ \ N-COO-CH ₂ -C ^ C-CHC 1-CH ₃
\ / ι 66 0 I.
H

*) Minor leaf damage.

Severe leaf damage was observed with the use of propargylestem, while with the

Application of the chloropentinyl ester showed only minor leaf damage.

Claims (1)

PATENT CLAIM: Fungicidal agents, characterized in that they contain a carbamic acid ester of the formula NH-COO-CH ₂ -C ^ C Xn I — riJY - denotes identical or different optionally substituted alkyl, cycloalkyl, alkoxy or alkoxyalkyl radicals or halogen, cyano or nitro radicals and η = 1, 2 or 3 and Y denotes chlorine or bromine. CHY-CH ₃ Considered publications: in the X hydrogen or one or more German Auslegeschrift No. 1017 407.