DD145692A5 - AGROCHEMICAL AGENTS - Google Patents

Description

215 3Φ1 ~

New benzimidazole derivatives containing agrochemical agents

Field of application of the invention '.

The present invention relates to novel benzimidazole derivatives as active ingredient-containing agrochemical agents.

Characteristic of the known technical solutions

The use of various benzimidazole derivatives as fungicides is known (German Offenlegungsschrift No. 1 956 157, GB Patent Specification No. 1 238 977 and Hungarian Patent Specification No. 167 242). Among the known compounds, especially the carbamoylated

23816-77 / Fne 2)

Benzimidazole derivatives, e.g. the methyl-1- (butylcarbamoyl) -2-benzimidazole carbamate has an excellent effect.

Presentation of the nature of. Invention;

It has now been found that the new benzimidazole derivatives of the general formula

wherein

1 R is hydrogen or a group of the general formula

X = C - NH - R ² V

means, in which

X stands for oxygen or sulfur and

R is alkyl of 1-4 carbon atoms, phenyl or substituted phenyl and Y is an organic or inorganic anion has a better fungicidal activity than the known benzimidazole derivatives. The compounds are particularly effective against Fusarium graminearium, Penicillium expansum, Trichothecium roseum, Helminthospo-

rium carborum, Aspergillus flavus. -

The invention relates to an agrochemical composition, characterized by a content of one or more benzimidazole derivatives of general formula I mixed with the usual organic or inorganic carriers, diluents, extenders, dispersants, emulsifiers, or surface-active

'' Ζ .. '' '-' '..' '. '3)'. '.'

2 1 5 3 © f .- '3-

agents ·

The formulations according to the invention generally contain between 0.1-95% by weight of active ingredient

The active compounds according to the invention can be converted into the customary formulations, such as solutions, powders, suspensions, emulsions, oil dispersions, pastes, and dusting agents, and used in accordance with the intended use by spraying, scattering, dusting, pouring, spraying, and in any case the finest distribution is intended to be secured ·

For the preparation of ready-to-use spray solutions, emulsions, pastes and oil dispersions, the medium and high boiling point mineral oil fractions, e.g. Gas oil or petroleum, oils of vegetable or animal origin, aliphatic or aromatic hydrocarbons, and derivatives thereof,

e.g. Benzene, toluene, xylene, paraffin, methanol, ethanol, butanol, acetone, chloroform, carbon tetrachloride, etc. strongly polar solvents such as dimethylformamide, dimethyl sulfoxide, and water, etc.,

The aqueous application forms can be prepared from emulsion concentrates, pastes, or wettable powders, oil dispersions by addition of water. In the preparation of emulsions, pastes or oil dispersions, the active compounds are, if desired, dissolved in oil or in a solvent and preferably homogenized in the presence of dispersants, wetting agents, adhesives and / or emulsifiers in water.

As surfactants come essentially in

4)

15

Question: lignosulfonic acid; Naphthalic acid, phenolsulfonic acids, alkali metal, alkaline earth and ammonium salts thereof, glycol ether salts of fatty acid alcohol, condensed products of sulfonated naphthalene derivatives with formaldehyde, sulfite liquors, etc.

The powders, dusts and scattering agents are prepared by comminution and mixing of the compounds of general formula I and the solid carriers. Suitable solid carriers are silicic acid, silica gel, kaolin, talc, lime, chalk, dolomite, loess, clay, magnesium hydroxide, calcium sulfate, magnesium sulfate , Synthetic fertilizers, such as ammonium nitrate, ammonium sulfate, ureas, vegetable products such as, for example, drunkenmeats, furfurol bran and other carriers may be used. embodiments

The further details of the invention can be taken from the following examples.

Example 1 (Biological Example) The biological effect was carried out by means of the "poisoned agar plate" method at concentrations of 100, 250 and 500 ppm. 2 % potato dextrose agar was used for the studies. The test results are shown in the following tables.

I. Test organism Fisarium graminearum

Colony diameter 25

active substance 100 ppm 250 ppm 500 ppm A 0 0 0 B · · ^; '· -'' O 0 0 C O 0 0 Benomyl stood.Control O 0 0

untreated control 35 36 35

, , - ^i: - Λ. '' -V - - '/ ·''-.,-.''5)

215 301 -ε-

II. Penicillium expansum

Colony diameter

Active ingredient 100 ppm 250 ppm 500 ppm

A 0 O O

B OO O

C OO O

Benomyl stood. Control O O O

untreated control 30 32 31

III · Test organism Aspergillus flavus colony diameter

Active ingredient 100 ppm 250 ppm 500 ppm

A O OO

B 0 0 0

C 0 0 0

Benomyl stood. Control O O O

untreated control 39 40 39

IV. Helminthosporium carborum

Colony diameter

active substance 100 ppm 250 ppm 500 ppm A O O O B O O O C O O O Benomyl stood.Control O O O

untreated control 38 38 39 V _m Trichohecium roseum

colony diameter 500 ppm V / he active ingredient contained 100 ppm 250 ppm O A O Ό O B O O O C O O : O Benomyl stood.Control O O

untreated Kontrolla 30 31 32

215

A = i-butylcarbamoyl - ^ - aminobenzimidazole hydrochloride B = i-methylcarbamoyl - ^ - aminobenzimidazole hydrochloride C = i-butylcarbamoyl - ^ - aminobenzimidazole salicylate Benomyl = methyl 1- (butylcarbamoyl) -2-benzimidazole-carbamate ,

- Example / 2 _m (Biological Example) The fungicidal tests were carried out in laboratory (in vitro) and in a greenhouse (in vivo). In the laboratory experiments, the compounds were mixed in the soil so that the concentration of the chemicals in the soil is 100 ppm. The following mushrooms were used in the experiment:

Botrytis cinerea Fusarium oxysporum Stemphylium radicinum Helminthosporium turcicum Trichothecium roseum Rhizoctonia solani Alternaria tenuis

During the in vivo experiments, the plants were sprayed and infected with a 1000 ppm solution of the compounds. The experiments were carried out with the following species:

.Erysiphe graminis - wheat · Sphaerotheca fuliginea - cucumbers Phytophthora infestans - tomatoes Uromyces appendiculatus - beans.

The systemic action of the compounds was also tested against Erysiphe graminis.

The fungicidal action was shown in the table below.

215305

shown. The efficiency was rated as follows

0 = inhibition of 0-25 %

1 =? Inhibition of 26-50 %

2 = inhibition of 51-75 % .

3 = inhibition of 76-99 % 4 = inhibition of 100%.

Versuchserpebnis5e

A) Laboratory tests (in vivo)

• Links

AB CDEFGHI

Botrytis cinerea 0 0 2 2 22 2 1 3 Fusarium oxyspo-

around T12O11312

Helminthosporium turcicum 2111 01 20 2

Trichothecium

roseum - - - - - - -

Stemphylium

radicinum 2 2 2 2 2 1 3 2 1 Rhizoctonia

solani 0 022 1 2 32 2

Alternaria

tenuis 1 0 2 1 1 11 0 1

215 30 1

B) Greenhouse experiments (in vivo) a) Contact action

Compounds A B CD E FG HI

2 2 1 1 O 1 2 2 O O O O O O O O 2 2 2 3 3 2 2 3 O O 1 1 1 1 O 2

Erysiphe graminis 2

Sphaerotheca fulginea O

Phytophthora infestans 2

Uromyces appendiculatus O

b) systemic effect

links

A BC DEFG HI Erysiphe graminis 2 0 0 0 0 0 0 1 0

The connections:

A = 2-amino-benzimidazole hydrochloride

B a 2-amino-benzimidazole sulphate

C =? 2-amino-benzimidazole bisulfate

D = 2-aminobenzimidazole hemitertarate

E a '2-amino benzimidazole benzoate

F = 2-aminobenzimidazole salicylate

Gβ'-l-butylcarbamoyl-2-aminobenzimidazole hydrochloride

H = i-methylcarbamoyl-2-aminobenzimidazole hydrochloride

I = i-butylcarbamoyl-2-aminobenzimidazole salicylate

Example 3

Production of dusts

60% by weight of i-butylcarbamoyl-2-aminobenzimidazole-hydrochlo-

Reach 40% by weight of kaolin

Example 4

Preparation of Emulsifiable Concentrates 20% by weight of 1-butylcarbamoyl-2-aminobenzimidazole salicylate

  - '' .. · '·' '. '/ 9) ""

3 wt.% Rapeseed oil 30 wt.% Dimethylformamide

7 % by weight of naphthalenesulfonic acid 40% by weight of xylene

- Claims -

Claims (4)

12 449 Invention Claim 1. Agrochemical compositions, preferably fungicidal agents, characterized in that in addition to the usual auxiliaries and Irägerstoffen a content of at least one benzimidazole derivative salt of the formula in which R is hydrogen and a group of the formula X s C - NK - R ² - V - in which X oxygen, sulfur, means and 2
R is alkyl of 1 to 4 carbon atoms, phenyl or substituted phenyl and Y stands for an organic or inorganic anion. , o Method of controlling fungi, characterized in that benzimidazole derivative salts according to item 1 are allowed to act on fungi or their habitat. 3 · Use of benzimidazole derivative salts according to item for controlling fungi. 4. A process for the preparation of agrochemical agents, preferably of fungicidal agents, characterized in that mixing benzimidazole berivate salts according to point Λ with extenders and / or surface-active agents. , ··, · ·.