DD296400A5 - HERBICIDE MEDIUM - Google Patents

Abstract

The invention relates to new herbicidal compositions and their use postemergence. The task is achieved according to the invention by the use of trichloroacetanilides of the formula I as active ingredients. Formula I {pesticides; Herbicide; Trichloracetanilide}

Description

Field of application of the invention

The present invention relates to trichloroacetanilides and their use in crop protection.

Characteristic of the known technical solutions

It is known that various trichloroacetanilides are suitable for controlling phytopathogenic fungi (DE 834152, DE 1806291, DD 237252). Also reported are herbicidally active substances from the group of trichloroacetanilides (K. Hoiley, Proc. Brit. Weed Control Conf., 3rd, Conf. Blackpool 1956, 235-45, GM Lubulska, VP Rudavsky and JG Haskin, Fizlol. Rest, 11, 171-4 [1964]). The efficiency of these compounds does not reach the magnitude of standard herbicides.

Object of the invention

The aim of the invention is the search for new active ingredients for herbicidal compositions with good performance properties.

Explanation of the essence of the invention

The object of the present invention is to provide trichloroacetanilides with improved herbicidal activity in comparison to the herbicidal compounds of this type known from the literature. It has now been found that trichloroacetanilides of the general formula I

Cl.X - CO - NM - (C ^ > - \ 0 "(I)

in which

X is hydrogen, chlorine or bromine and

Y is chlorine or bromine,

have very good selective herbicidal properties and thus are well suited as active ingredients of herbicidal agents. The compounds of the general formula I can be prepared in a manner known per se. Thus, trichloroacetanilides are obtained by condensation of the corresponding substituted anilines with trichloroacetic acid in the presence of phosphorus oxychloride (F.A. Berli and L. M. Ziti, Arch. Pharm.285,372-5). The new 2,6-dihalo-4-nitro-trichloroacetanilides can be advantageously prepared by adding trichloroacetyl chloride to a melt of trichloroacetic acid and the corresponding aniline. In the nitration of aromatically halogenated trichloroacetanilides with concentrated nitric acid (D = 1.48), another synthesis variant is considered.

The herbicidal compositions according to the invention have a strong phytotoxic activity and a broad activity for killing plants or parts of plants. For the practical application of the unforeseeable fact is of extreme importance that depending on the application dose in addition to the control of dicotyledonous weeds, especially Apera spica-venti, as the most important grass in cereals, can be safely controlled. The agents according to the invention can

Accordingly, they are advantageously used as herbicides in postemergence or during emergence of the crop plants, being particularly suitable for use in summer and winter cereals.

The rates vary depending on the nature of the desired effect, the nature of the weeds, the time of Application, climatic conditions and soil conditions. The amount to be applied is generally between 0.2 and 5 kg of active ingredient / ha, preferably between 0.5 and 2 kg Ai / ha. The agents according to the invention can be converted into the customary formulations, such as solutions, emulsion concentrates, Microemulsions, suspensions, wettable powders, granules, microcapsules, etc. are transferred. They are in known Way with common extenders, such as liquid solvents and / or solid carriers, optionally under Use of surface-active agents dissolved or dispersed or ground together or according to other known ones Formulated procedure. The active ingredient content of the agents according to the invention is 5-95 Ma .-%, depending on the intended use.

preferably 10-90 Ma .-%.

The application is carried out in a customary manner, for example by pouring, spraying, spraying, atomizing or scattering. The compositions according to the invention can be used to expand the range of application and plant care with other known herbicides, Fungicides, insecticides, acaricides, nematicides, growth regulators and fertilizers mixed and in common

be applied. The following examples illustrate the advantageous properties and the good herbicidal activity of the agents according to the invention.

embodiments example 1 Trichloroacetate-a-chloro-nitroanilide (Comp # 1)

1.84 g (12 mmol) of phosphorus oxychloride are added to 4.08 g (25 mmol) of trichloroacetic acid and, after dissolution of the trichloroacetic acid, 4.31 g (25 mmol) of 2-chloro-4-nitroaniline are added with cooling. After the reaction has subsided, hydrogen chloride evolution on the water bath is continued until the end of the reaction. The solid obtained is mixed with ice-water, filtered off with suction and the precipitate is washed several times with water. The recrystallization is carried out from aqueous ethanol. F 62-66 ° C. Yield: 7.23 g (91% of theory).

Example 2 Trichloroacetate e-dichloM-nitroanilide (Comp # 2)

10.35 g (0.05 mol) of 2,6-dichloro-4-nitroaniline and 24.51 g (0.15 mol) of trichloroacetic acid are heated to melt and then 13.64 g (0.075mot) of trichloroacetyl chloride are added dropwise. The melt is held for 4 h at 130X and the still-hot mass with vigorous stirring in 11 ice water. The precipitate is filtered off with suction, washed several times with water and crystallized from hexane / acetone. F 144-145 ^e C. Yield: 14.27 g (81% of theory).

In an analogous manner trichloroacetate ^ .e-dibromo-nitroanilide (Comp. No. 3) can be represented. F115-118 ° C. Example 3

Composition of a 20% spray powder 20Ma .-% trichloroacetate-2,6-dichloro-4-nitroanilide (Comp. No.2)

5mA .-% calcium lignosulfonate

5 Ma .-% Meta upon 20 Ma .-% Silica K60 50 Ma .-% Kaolin

Example 4

Herbicidal action

Five species of weeds were grown in plastic cups in a row in a climatic room at 20 ° C and 12 hours of light and dark change, using industrial compost with NPK fertilizer supplement containing 70% peat and 30% sea mud. was carried out by spraying using a brewing amount of 40 ml / m ² after emergence of the plants in the growth stage indicated below:

Stellaria media 6-8-leaf stage Chenopodium album 4-leaf stage Sinapisspez. 4-leaf stage Galiumaparine 3 whorled Aperaspica venti 3-4-leaf stage The rating of the harmful effect in% was made after 14 days of medium action.

expenditure Stellaria Chenopodium Injury (%) Galium -3- 296 400 Ver amount media album sinapis aparine am IcgAS / ha spec. Ap era dung 30 10 15 spica-venti No. 0.5 40 50 60 20 1 1.0 90 95 90 40 10 2.0 45 25 100 20 25 0.5 75 50 60 45 70 2 1.0 95 95 95 60 60 2.0 30 30 100 30 95 0.5 70 50 50 30 100 3 1.0 90 95 50 60 20 2.0 70 60 80

Claims (3)

1. Herbicidal agents, characterized in that they are trichloroacetanilides of general formula I as active ingredients, Cl "C - CO - NI! -'7 "" "Yi-NO ,, m in which X is hydrogen, chlorine or bromine and Y is chlorine or bromine, in addition to common excipients and carriers included. 2. Composition according to item 1, characterized in that it contains as active substance trichloroacetate ^^ - dichloro ^ * nitroanilide. 3. Use of funds according to item 1, characterized in that they are used for controlling postemergence weeds.