DD267419A1 - HERBICIDAL AGENTS FOR THE CONTROL OF UNCRAFT IN POTATO CULTURES - Google Patents

Abstract

The invention relates to novel selective herbicide combinations, preferably for weed control in postemergence potato crops. As active ingredients, in addition to customary auxiliaries and tracer substances, they contain, according to the invention, combinations of compounds of the general formula in which R 1 is an alkyl group having 1 to 2 C atoms or an alkoxy group having 1 to 2 C atoms and R 2 is an alkyl group having 1 to 4 C atoms. Atoms, with 3-methylthio-4-amino-6-tert-butyl-1,2,4-triazine-5 (4H) -one or 2-methyl-4-chloro-phenoxyacetic acid. formula

Description

Field of application of the invention

The invention relates to novel herbicidally active compositions for the selective control of monocotyledonous and dicotyledon weeds postemergence in cultivated plant stands, especially in potato crops.

Characteristic of the known prior art

It is already known that dicarbamates based on m-aminophenol can be used as selective herbicides in beet and vegetable crops, for example peas, carrots and onions (DE AS 1567151, DE-AS 1538621, DE-AS 1567163).

Also in cotton crops an application for this class of substances was later found as selective herbicides (DE-AS 23 06 848, DE-AS 2310649).

Furthermore, it is known that derivatives of m-aminophenol having a carboxylic acid amide / carbamate substituent pattern have herbicidal properties and these compounds can be used at high dosages as total herbicides, while at low application rates they have only a weak herbicidal activity and no sufficient selectivity over crop plant stocks ( US-PS 3S36570, US-PS 3876684, US-PS 3857693, DD-PS 89754).

From GB-PS 1237770 it is apparent that compounds of ni-aminophenol with a carboxamide / N-methylcarbamate have insecticidal properties.

Furthermore, it is known that starting from m-aminophenol synthesized derivatives with a complicated carboxylic acid amide / Carban-.at-StrukUirmuster as selective herbicides in Kulturpflanzenbeständon, especially in beets, cotton, soybeans. Rice and potatoes can be used (US-PS 4344790). However, these compounds have the disadvantage that they are compared to the potato crops weakly phytotoxic and sufficient weed control amounts between 3 and 5kg / ha AS required for adequate control of weeds, so that the application is associated with a high cost, which is among today's modern methods weed control in agriculture is no longer economically justifiable.

To combat Uno / Ääsem and weeds in potato cultures are mainly as active ingredients S-methylthio ^ -amino-ö-tert.

butyl-1,2,4-triazine-5 (4H) on (metribuzin) in the pre-emergence and postemergence process (DE-OS 1542873, DE-OS 1635596, DE-OS 2138031, DE-OS 2165554) and 2-methyl- 4-chloro-phenoxy-9-acetic acid (MCPA) used to destroy post-emergence dicotyledonous weeds.

A disadvantage of the use of Metribuzin in potato cultures, a phytotoxicity occurring due to the variety and the insufficient effect against Windenknöterich (Fallopia convolvulus),.

When using MCPA, dicotyledonous weeds are very well killed, while monocotyledonous weeds are not adequately controlled by this drug.

Object of the invention

The aim of the invention is to develop new herbicidal agents to expand the still existing small range of Nachauflaufherbiziden for use in potato crops. These new agents must effect improved weed control and crop tolerance at low application rates to meet today's growing economic demands of agricultural use.

Presentation of the essence, the invention

The object of the invention is. To find active substances, which can be used in combination selectively in postemergence potato cultures for weed control.

This object is achieved in accordance with the invention in that the novel herbicidal compositions are suitable for the selective control of monocotyledonous and dicotyledonous weeds in the postemergence process, in particular in potato crops, and as active ingredient comporers in addition to compounds of the general formula

in the

R 'is an alkyl group having 1 to 2 C atoms or an alkoxy group having 1 to 2 C atoms

R ^{2 is} an alkyl group having 1 to 4 carbon atoms,

as an additional component

3-methylthio-4-amino-6-tert-butyl-1,2,4-triazine-5 (4H) -one (II) or

2-methyl-4-chloro-phenoxyacetic acid (III)

and the usual auxiliary and Trägersto'fen included.

It has surprisingly been found that these new Wirkstoffkombinationon aufwe a special broader and selective herbicidal activity in crop stands of ^{Kartoffolkul'uren:} sen, although the compounds of the general formula I described in the prior art as little kulturpflanzenvert.cigüch and from a low selectivity were.

Furthermore, it was found that the combinations according to the invention show significantly better herbicidal potencies than could be expected on account of the addition of the individual effects of the components. This is reflected both in the almost complete complement of the action spectra and in the increase in activity against hard-to-control weeds, which is due to a true synergistic effect proven by the method of COLBY.

This synergistic effect of the combinations according to the invention is particularly pronounced in certain combination ratios. However, the proportions of the components may vary in relatively large areas depending on the prevailing weed environment as well as the environmental and site conditions. The weight ratio of one active ingredient of the general form! I to the active ingredient I! or active ingredient III is between 2: 1 and 15: 1 or 2: 1 and 6: 1, preferably between 3: 1 and 7: 1 or 3: 1 and 5: 1. A good control success is achieved with the inventive compositions at application rates of 1 to 2 kg / ha of the active ingredient mixture.

The compounds of the general formula I are known and can be prepared by the methods given in the literature. Some of the active ingredients are listed in Tabt Me 1:

Table 1: Compounds of the general formula I

Drug-No. R ¹ R ^J Fp ( ⁰ C)

1.1 CH ₃ CHj 155-157 I / 2 CH ₃ CH ₂ - CH ₃ 153-154 I / 3 CH ₃ CH ₂ CH ₃ - (CH ₂ I ₂ -CH ₂ 136-138 I / 4 OCH ₃ CH ₃ 125-127 I / 5 OC ₂ H ₀ CH ₃ 132-134

The application of these new herbicidal compositions is expediently carried out in the preparation and application forms customary for herbicides, such as solutions, emulsions, suspensions, powders, pastes and granules, which usually comprises the addition of liquid and / or solid carriers or diluents Surfactant and other formulation aids may be prepared and diluted with water for use. The formulations prepared generally contain between 0.1 and 95% by weight, preferably between 0.5 and 90% by weight of active ingredient. The application forms depend on the intended use. In any case, they have to ensure a fine distribution of the active substances. The preparation of the preparations is carried out in a conventional manner by mixing or milling

 The examples below are intended to illustrate the invention without limiting it.

Ausführungsbeispicle

To demonstrate the herbicidal activity and the crop tolerance of the combinations according to the invention, experiments were carried out on arable land in arable crops. In potato crops the treatment is postemergence, that is to say after emergence of the crops and after emergence of the weeds. The assessment of the control success and the compatibility was made according to the following rating scheme:

Boniturnote Damage in% 1 100-96 2 95-80 3 85-71 4 70-56 5 55-46 6 45-31 7 30-16 8th 15-6 9 5-0

The following crops, weeds and grass weeds have been used to improve tolerability and the success of confinement and are characterized in the following Table 2 as follows:

A potatoes (Solanum tuberosum) variety: Adretta

B potatoes (Solanum tuberosum) Variety: Sola

C potatoes (Solanum tuberosum) Variety: Karpina

D Potatoes (Solanum tuberosum) Variety: Dragonfly

E Barnyardgrass (Echinocloa crus-galli)

F Annual bluegrass (Poa annua)

G White Goosefoot (Chenopodium album)

H field hellebore (Thlaspi arvense)

I Stengfilumfassende dead Nettle (Lamiumamplexicaule)

K Real Fumitory (Fumaria officinalis)

L Chickweed (Steüaiia media)

M Real chamomile (Matricaria chamomilla)

N willowweed (Fallopia convolvulus)

O Krummer Foxtail (Amaranthus retroflexus)

P Common shepherd's purse (Capsella bursa-pastoris)

The results of the herbicidal action of the combinations according to the invention from the numerous experiments are summarized in Table 2.

This also means:

! / 2-I / 4 active compounds of the general formula I.

I! Active ingredient S-methylthio ^ -amino-e-tert-butyl-i, 2,4-triazine-5 (4H) -one (metribuzin)

III active ingredient 2-methyl-4-chloro-phenoxyacetic acid (MCPA)

Table 2: Herbicidal action of the erfindiingsgemäßen combinations against the specified weeds and Ui.gräser in Kartoffelkulturnn in post-emergence treatment

drug expenditure Potatoes grass weeds B C D R F weeds H I K L M N O P No. amount 9 9 9 8th 7 7 6 7 8th 7 8th f) 6 kg / ha A 9 9 9 8th 6 G 6 5 6 7 6 8th 6 5 Il 0.1 9 9 9 8th 6 5 7 6 4 5 6 5 7 5 4 (known) 0.2 9 9 8th S 5 4 5 5 3 4 4 5 7 4 3 0.3 9 8th 8th 8th 3 3 ö 4 3 2 3 3 6 3 2 0.4 8th 9 S 9 9 9 4 7 8th 8th 9 8th 8th 8th 7 0.5 8th 9 9 9 9 9 2 6 7 8th 8th 6 8th 7 6 III 0.24 9 9 9 9 9 8th 5 4 6 6 7 5 7 6 5 (known) 0.32 9 9 9 9 7 6 3 6 6 5 6 4 5 5 5 0.40 9 9 9 9 7 5 2 4 4 3 4 4 3 3 4 I / 2 1.0 9 9 9 9 5 4 5 3 2 3 3 2 2 3 3 (known) 1.5 9 9 9 - 6 6 4 - 5 5 4 - 3 - - 2.0 9 9 9 - 5 5 3 - 4 3 4 - 2 - - I / 3 1.0 9 9 8th - 5 5 5 - 3 3 3 - 2 - - (known) 1.5 9 9 9 8th 7 3 6 - - - 4 - 5 6 2.0 8th 9 - 9 7 5 2 5 - - - 3 - 4 5 I / 4 1.0 9 9 - 9 6 5 5 4 - - - 2 - 3 3 (known) 1.5 9 9 9 9 6 5 4 4 4 3 4 3 4 4 3 2.0 9 9 9 9 5 4 4 2 2 2 3 3 2 2 2 Il + 1/2 0.1 + 1.0 9 9 9 9 4 3 3 2 2 2 3 2 3 1 2 (Invention). 0.1 + 1.5 9 9 9 9 3 3 2 2 2 1 3 ? 2 1 2 0.2 + 1.0 9 9 9 9 2 2 2 2 1 1 2 1 2 1 2 0.2 + 1.5 9 9 9 9 2 2 1 2 1 1 2 1 2 1 1 0.3 + 1.0 9 9 9 - 6 5 1 - 3 3 2 - 2 - - 0.3 + 1.5 9 9 9 - 4 4 1 - 2 2 2 - 1 - - Il + 1/3 0.1 + 1.0 9 9 9 - 5 4 3 - 2 2 1 - 2 - - (Invention). 0.1 + 1.5 9 9 9 - 4 3 2 - 2 1 1 - 1 - - 0.2 + 1.0 9 9 9 - 3 3 2 - 2 1 1 - 1 - - 0.2 + 1.5 9 9 9 -. 3 2 1 - 1 1 1 - 1 - - 0.3 + 1.0 9 9 - 9 6 6 1 4 - - - 3 - 4 3 0.3 + 1.5 9 9 - 9 5 4 1 3 - - - 2 - 2 3 Ii +1/4 0.1 + 1.0 9 9 - 9 5 4 3 3 - - - 2 - 2 2 (Invention). 0.1 +1.5 9 9 - 9 4 3 2 3 - - - 1 - 1 2 0.2 + 1.0 9 9 - 9 4 2 2 3 - - - 1 - 1 2 0.2 + 1, C 9 9 - 9 4 2 2 2 - - - 1 - 1 2 0.3 + 1.0 9 9 9 9 7 6 2 4 4 3 4 4 3 4 3 0.3 + 1.5 9 9 9 9 6 5 1 3 3 1 2 3 2 2 3 Ill + 1/2 0.24 + 1.0 9 9 9 9 6 4 2 3 3 2 3 2 2 3 2 (Invention). 0.24 + 1.5 9 9 9 9 5 3 2 2 2 1 2 2 2 2 2 0.32 + 1.0 9 9 9 9 4 3 1 2 2 1 2 1 1 1 2 0.32 + 1.5 9 9 9 - 6 6 1 - 3 3 3 - 2 - - 0.40 + 1.0 9 9 9 - 5 4 1 - 2 2 3 - 1 - - Ill + 1/3 0.24 + 1.0 9 9 9 - 5 4 2 - 2 2 2 - 2 - - (Invention). 0.24 + 1.5 9 9 9 - 4 3 1 - 2 1 2 - 1 - - 0.32 + 1.0 9 9 9 - 4 3 1 - 2 1 2 - 1 - - 0.32 + 1.5 9 9 - 9 8th 7 1 3 - - - 4 - 3 4 0.40 + 1.0 9 3 9 b 5 I 2 - - - 3 - 2 3 ! Il + 1/4 0.24 + 1.0 9 9 - 9 7 5 4 2 - - - 3 - 2 3 [Invention.) 0.24 + 1.5 9 9 - 9 6 4 3 1 - - - 2 - 2 2 0.32 + 1.0 9 9 - 9 5 4 3 1 - - - 2 - 1 2 0.32 + 1.5 9 2 0.40 + 1.0 9 2

The combinations according to the invention, consisting of the active compounds II + I / 2, N - '. I / 3 and II + I / 4, are better tolerated by crop plants than the sole application of the known active compound II and also have a very good herbicidal activity against monocots and dicotyledonous weeds. Particularly noteworthy here is the very good control of Fallopia convolvulus. Also in comparison to the individual applications of the active ingredients I / 2 - I / 4 is achieved with the combinations according to the invention a much better destruction of the specified unggräsc-r and weeds. Mild active ingredient combinations of the invention III + I / 2, III + I / 3 and III + I / 4 are very well controlled at high selectivity'dikotyle weeds. Compared to the Einzolanwendungen of the active ingredients I / 2 - l / 4urvllll also grass weeds with the combinations are better controlled.

Table 3: Influence of the combinations according to the invention on the yield in potato crops kept uncrowded during postemergence application (relative values, reference base control)

Wirkstöff- Il +1/3 Expenditure- Income in% the potato crops C D No. [Invention.) amount 100 100 kg / ha A B 102 100 control - 100 100 103 98 Il 1 + 1/4 0.1 98 10C 94 94 (known) [Invention.) 0.3 100 102 101 103 0.5 95 100 III Il +1/2 0.4 100 98 98 102 (known) ! Invention.) 103 98 I / 2 '1 + 1/3 1.0 100 102 100 100 (known) invention.) 1.5 102 100 102 98 I / 3 Il + 1/4 1.0 102 98 103 100 (known) erfindungsgeiv.) 15 103 98 100 102 IN THE 1.0 98 97 103 98 [known) ', 5 98 100 101 100 Il + 1/2 0.1 + 1.0 100 102 102 102 [Invention.) 0.1 + 1.5 100 100 102 93 0.3 + 1.0 102 100 102 102 • 0.3 + 1.5 100 102 98 100 0.1 + 1.0 102 100 103 103 0.1 + 1.5 103 100 100 100 0.3 + 1.0 100 102 100 98 0.3 + 1.5 100 100 103 103 0.1 + 1.0 98 100 102 102 0.1 + 1.5 98 98 98 102 0.3 + 1.5 100 102 102 100 0.4 + 1.0 100 100 103 100 0.4 + 1.5 102 98 100 103 0.4 + 1.0 102 98 102 100 OA + 1.5 102 98 98 102 0.4 + 1.0 98 100 0.4 + 1.5 100 102

The combinations according to the invention have a fluctuation range of ± 3% compared to (Jer control no negative influence on the crop "while compared to the single application dos known drug Il at} Iner application rate of 0.5 kg / ha AS \ n dependence on the type of yield reductions of 5-6% occur.

In order to assess the synergistic effect, the expected effect for a given combination of zv.'ei herbicides according to SR Colby "Calculating synergistic and antagonistic responses of herbicidal combinations" in Weeds 15 (1), p.20-22, ( 1967) as follows: if:

X = damage caused by herbicide at pkg / ha application rate

Y -% damage by herbicide B at q kg / ha application rate and Er = mean the expected damage from the herbicides A and B at ρ and q kg / ha application rate, then

E _R =

Y-

XY

100

If the damage E found is greater than the calculated En, then the combination is over-additive in its effect, ie there is a true synergistic effect (Ei> Er).

If E, = E _n , then the effect is additive.

If E, <Eh, then there is an antagonistic effect.

As an example, in parallel to the calculations in experiments, the actual damage to the chicken millet and the curvature in the case of post-harvest application was determined (Table 4):

Table 4: Determination of the synergistic effect in the control of chicken millet and curling in postemergence in potatoes.

application rate potatoes dragon-fly Injury in % " -6- 267 419 active substance kg / ha Adretta gef. ²¹ ber. ³¹ winch No. knöte- 0 rich 0.1 0 0 10 gef. calc. Il 0.2 0 6 10 10 (known'· 0.3 0 8th 40 10 0.4 8th 12 50 20 0, b 10 0 80 20 0.24 0 0 0 40 IiI 0.32 0 0 0 10 (known) 0.40 0 0 0 10 1.0 0 0 20 20 1.2 1.5 0 0 20 50 (known) 1.0 0 0 40 80 3.1 1.5 0 0 BO 80 (known) 1.0 0 0 10 90 1.4 1.5 0 0 20 40 (known) 0.1 + 1.0 0 0 40 28 50 Il + 1/2 0.1 + 1.5 0 0 50 28 60 55 (Erfinckingsgem.) 0.2 + 1.0 0 0 6C 28 90 82 0.2 + 1.5 0 0 80 28 80 55 0.3 + 1.0 0 0 90 52 90 82 0.3 + 1.5 0 0 90 52 90 60 0.1 + 1.0 0 0 40 46 90 84 Il +1/3 0.1 + 1.5 0 0 60 55 90 82 (CrfintUingsgcnt.) 0.2 + 1.0 0 0 50 46 100 91 0.2 + 1.5 0 0 60 55 90 82 0.3 + 1.0 0 0 80 64 100 91 0.3 + 1.5 0 0 80 70 100 64 0.1 + 1.0 0 0 40 19 100 92 Il +1/4 0.1 + 1.5 0 0 50 28 80 46 (Invention). 0.2 + 1.0 0 0 50 19 80 55 0.2 + 1.5 0 0 60 28 90 46 0.3 + 1.0 0 0 60 46 90 55 0.3 + 1.5 0 0 60 52 90 52 0.24 + 1.0 0 0 20 20 90 60 Ill + 1/2 0.24 + 1.5 0 0 40 20 80 55 (Erfinduncjsgem.) 0.32 + 1.0 0 0 40 20 90 82 0.32 + 1.5 0 0 50 20 90 55 0.40 + 1.0 0 0 60 20 90 82 0.24 + 1.0 0 0 40 40 100 84 Ill + 1/3 0.24 + 1.5 0 0 50 50 90 82 (Erfindungsgeni.) 0.32 + 1.0 0 0 50 40 100 91 0.32 + 1.5 0 0 60 50 90 82 0.40 + 1.0 0 0 60 10 100 91 0.24 + 1.0 0 0 10 10 100 84 Ill + 1/4 0.24 + 1.5 0 0 40 20 60 46 (Erfindungsgeni.) 0.32 + 1.0 0 20 10 80 55 0.32 + 1.5 0 0 40 20 80 46 00:40 + 1.0 0 50 10 90 F 5 90 60

1) - the damage was scored with values from 1 to 9 and expressed in%. 2) = damage found

3) = the damage calculated on the basis of the value indicated by Colby

From Table 4 can be seen. dn din tnteärhlirhe ":." κϊγ "~ μ ^ g E, gri.icr -z: el; JIc Ui Kombinattonen show in the herbicidal effect a true synergistic effect.

En, ii. ii. ti ie Eriinciungsgemaisen

Claims (4)

claims: 1. Herbicidal agents for controlling weeds in potato cultures based on compounds of the general formula in the R ^{1 is} an alkyl group having 1 to 2 C atoms or an alkoxy group having 1 to 2 C atoms and R ^{2 is} an alkyl group having 1 to 4 C atoms, characterized in that they in addition to conventional excipients and carriers as an additional active ingredient Methylthio-4-arnino-6-tert-butyl-1,2,4-triazine-5 (4H) -one or 2-methyl-4-chloro-phenoxyacetic acid. 2. A herbicidal composition according to claim 1, characterized in that the weight ratio of an active ingredient of the given general formula to the additional component 3-methylthio-4-amino-6-tert-butyl-1,2,4-triazine-5 (4H ) -one between 2: 1 and 15: 1, preferably between 3: 1 and 7: 1. 3. A herbicidal composition according to claim 1, characterized in that the weight ratio of an active ingredient of the given general formula to the additional component 2-methyl-4-chlorophenoxyacetic acid between 2: 1 and 6: 1, preferably between 3Ί and 5: 1. 4. Application of the ^r bicidal agent for controlling weeds in potato crops, characterized in that the active ingredient combinations with the application rates of 1 to 2 kg / ha come postemergence in the application.