DE1191629B - Fungicides - Google Patents

Description

FEDERAL REPUBLIC OF GERMANY

GERMAN

PATENT OFFICE

EDITORIAL

Int. Cl .:

AOIn

German KL: 451-9 / 20

Number: 1191629

File number: B 66386IV a / 451

Filing date: March 16, 1962

Opening day: April 22, 1965

It was found that N-tridecyl-α-amino acids the general formula

C ₁₃ H ₂₇ - N - CH - COOH

I I

R 'R

in which R is hydrogen or the methyl group and R 'is an alkyl, cycloalkyl or hydroxyalkyl group means having good fungicidal properties.

The active ingredients are easily accessible from a technical point of view. A simple synthesis consists in the implementation of secondary amines or hydroxyalkylamines with halogen fatty acids in the presence of acid-binding substances, z. B. tertiary amines. Another simple synthesis option consists in the addition of unsaturated ones Carboxylic acids, ζ. Β. Acrylic acid or methacrylic acid, to primary or secondary amines or Alkanolamines. Another possibility for synthesis consists in the reaction of amines with formaldehyde ao and hydrocyanic acid or glycolonitrile to the amino acid nitrile and to the amino acid. The active ingredients available in this way are largely pure after the reaction and generally do not require any further purification. Some of the active ingredients can be further purified by distillation if necessary. Hydroxyalkyl amino acids go into morpholones in some cases with dehydration during the distillation. The manufacture of the Active ingredients are explained by the following description:

N- (2-hydroxypropyl) -N-tridecyl - «- aminopropionic acid

81 parts by weight of α-chloropropionic acid are added dropwise at 100 to 110 ° C. to a mixture of 192 parts by weight of N-tridecyl monoisopropanolamine, 170 parts by weight of toluene and 76 parts by weight of triethylamine, the mixture is refluxed for 3 hours, the toluene solution is washed with water and the toluene is distilled off in vacuo . A yellowish oil from the n | remains as a residue ⁵ = 1.4705. Yield: 236 parts by weight. (96% of theory).

Fungicides

Applicant:

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

Named as inventor:

Dr. Karl-Heinz König,

Dr. Ernst-Heinrich Pommer,

Dr. Walter Sänne, Ludwigshafen / Rhine;

Dr. Herbert Stummeyer, Mannheim

In an analogous manner, for. B. manufactured. (0 = mixture of isomers):
N-Tridecyl®-N- (3-hydroxypropyl) -glycocoU,

N- (2-hydroxyisobutyl) -N-tridecyl0 - «- aminopropionic acid.

N-Tridecyl0-N-cyclooctyl-glycocoll, N- (sec-butyl) -N-tridecyl®-a-aminopropionic acid.

The fungicidally and / or fungistatically active agents according to the invention can be used in the customary manner by adding solid extenders to dust powders or with the addition of dispersants, wetting agents and / or Adhesives to solid or liquid preparations used for the production of spray mixtures will. Next is z. B. processing into solutions and emulsions is possible after the Aerosol processes can be sprayed if the solvents customary for this purpose are used. The addition of other fungicides and / or insecticides is possible. As far as the invention If compounds act systemically, they can also be used as seed dressings. The effect of the compounds to be used according to the invention extends in particular to powdery mildew fungi, however also on other harmful fungi, as can be seen from the following examples.

For example

Leaves of barley seedlings grown in pots are treated with aqueous emulsions of 80% Active ingredient and 20% emulsifier sprayed and after the spray coating has dried on with oidia (spores) powdery mildew of barley (Erysiphe graminis var. hordei). The trial plants are then placed in the greenhouse at temperatures between 20 and 22 ° C and 75 to 80% relative humidity. The extent of powdery mildew development is determined after 10 days.

509 540/392

O = no infestation, graded up to 5 = total infestation.

= Mixture of isomers. * = slight leaf damage.

Active ingredient Infestation of the leaves after spraying with *% active ingredient broth

* = 0.008 I 0.015

0.03

0.06

N- (2-Hydroxyisobutyl) -N-tridecyl0-glycocoll

N- (2-Hydroxyisobutyl) -N-tridecyl0-a-aminopropionic acid ...

N-Cyclooctyl-N-tridecyl-a-alanine

N-Cyclohexyl-N-tridecyl-A-alanine

N-sec-butyl-N-tridecyl glycocoll

N-Cyclooctyl-N-tridecyl-aminoacetic acid

N-tridecyl-N- (2-hydroxypropyl) aminoacetic acid

N- (2-Ethylhexyl) -N-tridecyl - «- aminopropionic acid

Comparative substance according to US Pat. No. 2293 034

N-Lauryl-a-aminoacetic acid ethyl ester

Ethyl N-cetylaminoacetate

Ethyl N-stearylaminoacetate

Ethyl N-cyclohexylaminoacetate

Comparative substance according to German Auslegeschrift 1 120 802

^ -Dodecylaminocrotonic acid anilide

^ -Dodecylaminocrotonic acid benzylamide

/ S-dodecylaminocrotonic acid cyclohexylamide

^ -Dodecylaminocrotonic acid-o-anisidide

/ J-dodecylaminocrotonic acid-o-chloroanilide

Comparative substance according to German Auslegeschrift 1 125 713

N-lauryl-a-aminoacetic acid

N-lauryl-phenyl-acetamide

N-lauryl (p-chlorophenyl) acetamide

N-lauryl (o-chlorophenyl) acetamide

Control (untreated)

0
0

1
2
3
1
2
3

0
0
0
1
2
1
1
2

0
0
0
0
1
1
0
0

5
5
5
5
5

Example 2

. The following table shows the inhibition values against the fungus Aspergillus niger in nutrient solution. The nutrient solutions were inoculated with fungal spores and ^{incubated at 36 °} C. for 120 hours. The extent of the fungal growth was then assessed:

Active ingredient

Amount of active ingredient in the nutrient solution in parts of active ingredient per million parts of nutrient solution

100

50

25th

10

N-cyclododecyl-N-tridecylaminoacetic acid,

K-Cyclododecyl-N-tridecyl-A-aminopropionic acid

Control (untreated),

2-benzylphenol

Sodium pentachlorophenolate

p-chloro-m-cresol

2-Dmydroxy-5,5- <Uc-morodiphenylmethane

0 0

0 0 0 0

0 = no fungal growth, graduated to 5 = uninhibited fungal growth.

0 0

3 3

0 0 3 5 0 1 2 3 1 3 5 5 0 1 3 5

Claims (1)

Claim: Fungicidal agents, characterized in that they contain an N-tridecyl-a-amino acid the general formula CmH "- N - GH - COOH R 'R in which R is hydrogen or the methyl group and R 'is a butyl, cycloalkyl or hydroxypropyl or -butyl group. Considered publications:
German Auslegeschriften Nos. 1 125 713, 1 120 802; U.S. Patent No. 2,293,034. 509 540/392 4.65 © Bundesdruckerei Berlin